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Working with Trista Ch. 01

By: amberbmaid



Day 1:

I had just started my new job; only a month in and so far it was ok. I was laid off months earlier and forced to start working in a temp firm. The hours were all right, the pay was reasonable, and I couldn't complain about the commute. I was told this position could potentially turn into a full-time role if all went well during the 3 month "probationary period." The marketing department I was temping in was made up of all women so that was a nice little perk. This story is about one of those people and my first business trip.

I had met Trista on my first day, while she wasn't my boss on the official org-chart, I did take all my work direction from her. She was definitely one of those people you notice from across the room, at least I sure had. She was probably in her early 40's, but you couldn't tell by looking at her. She had a very intimidating personality though, and I wasn't sure what to make of her at first. But I did enjoy admiring her from a distance. 

I thought I hit the jackpot when my boss told me I would be flying to Las Vegas with Trista for a convention our company was participating in. As it was explained to me that my main duties out there would be helping her set up our display, taking down our display and checking in daily to see if our sales staff needed anything, but for the most part there was a lot of downtime. I couldn't wait. I had been out there once before, and loved it. This time, not only was the company paying for it, I was going with the gal I somewhat had the hots for in the office. I figured worse case, I could see her in a bikini by the pool one day, best case she might let her guard down a little, one thing would lead to another and we'd have one fun night or two together. I mean after all, as the saying goes, "What happens in Vegas stays in Vegas" right? 

The day before we were to fly out, her and I went over what we needed to bring, she told me to bring a couple of dressier outfits for going out to dinner, she told me to bring some clothes I could get dirty while we were setting up the displays, and she reminded me not to forget to bring something to wear at the pool. She specifically made mention that her bikini was already packed. I felt a sudden twinge in my pants as she told me that. I must have been blushing a little because she said, "well it is May in Las Vegas, and I'm going to lay out by the pool at some point."

Finally the day had arrived. We met at the airport and flew out that morning, arriving in Vegas just after noon. We checked into the hotel and Trista told me to get settled, change into some clothes to work in, and she'd pick me up in a half an hour or so. We'd get something to eat before going to the convention center to set up the display. 

The half hour went quickly; I changed into my work clothes, some gym shorts and a tee shirt along with some Nike Pro spandex compression shorts and shirt underneath, and was halfway through unpacking my suitcase when Trista knocked on my door. I let her in and she checked the view outside of my window, noticing that it over-looked the pool. I was grabbing my stuff to go as she noticed some of the clothing I had sticking out of my suitcase; she pulled out a pair of spandex running tights.

"What are these for?" she asked. I stammered that sometimes I wear them when I work out, if it's cold out or just want to work up a better sweat. "Do you wear these tights all by themselves?" she asked.

I told her no and when she asked why not, I blushed and explained to her that they don't leave much to the imagination. She just laughed and said good to know. So we headed out. 

Setting up the display was tougher work than I imagined. There was a booth we had to set up, various products we had to unpack and a lot of heavy lifting; not to mention that the convention center doesn't turn on the A/C until the start of the conference! I actually managed to work up a sweat. Trista noticed I had, and she started poking fun, saying that "maybe you should have worn your spandex tights if this is such a workout." Trying to make a witty comeback, I told her that I had compression shorts and a shirt on underneath. That piqued her interest. She said, "Well, let's see them." I lifted up the leg of my shorts to show her the navy spandex I had on underneath. 

"No, not like that, let's see the whole thing," said as she stopped working and stared at me. I started to make the excuse that it wouldn't be exactly proper attire, and others might see. She said "Nonsense, I'll make you a deal." She said she had on something similar under her shorts and tee shirt. She'd go down to what amounted to volleyball shorts and a sports bra if I were to remove my clothing and go in just the spandex I had on underneath. 

This is one of those decisions where taking the time to think things through would have helped. She already had told me she planned to lie out at the pool; my window overlooked the pool, so I would see basically the same outfit the next afternoon. However, sometimes patience is hard to come by. 

I took off my tee shirt, leaving the navy spandex shirt I had on underneath and looked at Trista. "Keep going," she instructed as she waved her hand indicating her impatience. I felt my cock growing harder in the spandex shorts, knowing that it would be fully on display. I slipped my loose basketball shorts down, revealing only the compression shorts underneath, my hardness pushing against the Lycra material. Standing before her in only the spandex attire, I looked up at Trista who was smiling. 

"Seems like you really enjoy being in just that tight little outfit," she smirked. I started to stammer a response or an excuse and mumbled something about being seen by others, but she just laughed and said, "Don't worry about being seen by others; unless they're up close, they won't be able to tell. It's just not all that noticeable." Talk about a low-blow.

Trista went back to work and I asked her about her taking off part of her clothing. "Oh we took that break so I sort of cooled off. Plus it looks like you have enough trouble controlling that little thing without me in skimpy attire." I couldn't understand it but I was harder than ever being out in the open like this in just spandex, everything on display and being picked on about my size by my co-worker. 

We finished the setup, Trista continually laughing at me hiding behind boxes or some part of the display booth anytime someone would come near as I tried to hide my attire and my hardness within it. When we were finished, I looked around for my tee shirt and shorts and saw Trista, holding them in her hand. I asked for them back and she said sternly, "No, you can have these when we get out to the car." I was about to protest, but her tone made it seem that it wasn't up for debate. She told me to lead the way; I hesitated for a bit but finally started walking. 

On the way out, I felt fully on display and my face was beet red as I must have passed about 20 people walking out to the car, Trista following behind me. I could feel her eyes on my ass, and the people I passed all noticed my rock hard cock being constricted by the spandex. When we got to the car, she tossed me my clothing saying, "Cover that little thing up already." I quickly got dressed and into the car. 

When we returned to the hotel, Trista told me that we had reservations at a pretty nice steakhouse so get dressed up and be ready to go in a couple of hours. She said to meet her downstairs at the sports book at around 8:00 and not spend my time relieving myself starting down at the girls around the pool. I just blushed and said ok, as that was exactly what I had planned on doing. 

A couple of hours later, I had cleaned up pretty well. I had showered, shaved and had on a nice suit. My hair was looking as good as it was going to, I had on my best cologne, and yet I was as nervous as could be. I felt like it was a first date. Granted we were going out to eat, but I had just spent the afternoon being humiliated by this woman who I found a bit brash and sometimes downright bossy, yet very s3xy still. For some reason, I had this overwhelming desire to please her. 

I was in the sports book bar watching the Minnesota Twins take on the Chicago White Sox, waiting for Trista to meet me. While I had found her s3xy before and was excited to see her all dressed up, this was beyond my expectations. 

She was wearing a very low-cut black mini dress. It accented her in all the right ways and I couldn't take my eyes off of her. She must have sensed that I was a bit overwhelmed and she smiled and said, "Well how do I look?" I told her she looked great and she thanked me. Trista sat down at the bar and ordered a merlot as the bartender gave me a second vodka/tonic; my first one had gone down pretty easily with how nervous I was. We talked about the game and baseball in general. I tried to impress her with the fact that I pitched in high school and I was impressed with her baseball knowledge as well. That didn't alleviate my nervousness however, as I was soon on my third drink as I continued to try to steal glances at her. 

I was definitely tipsy, the vodka/tonics doing the trick, as we headed off to dinner. Trista was turning quite a few heads and I was very pleased to be dining with her. Over dinner, we got to know each other better, her controlling the conversation for the most part, asking all the usual questions. I was still trying to steal glances at her low cut dress, probably not doing a very good job due to the whiskey sours, having a couple of more over dinner too. 

As we finished our dinner, Trista asked me if I wanted to join her to do some gambling. I suggested we go back to her room. She laughed and asked why we should do that. I told her that she looked very good and I would love to see her without that dress on. I suggested we make a bet and if she lost I'd get to see her without that dress. After some deliberation, we ended up deciding we were going to go to across the street to the casino and place one bet on roulette. The loser would have to do what the winner wanted for the remainder of the trip. I readily agreed. 

By the time we got across the street to the casino, my mind was racing with all the things I was going to have her do. The main thing was first remove that dress and after that, it was going to be repeated acts of debauchery. We went to the roulette wheel and she handed me a $5 chip. She said, "Black or red, your choice. If you lose, you have to do whatever I say the rest of the trip. Agreed?" I smiled and told her she was on. I figured there was so much s3xual tension in the air that even if I lost this bet, I'd end up a winner anyway as the end result would be the same. So I threw the $5 chip on black. When the ball finally stopped, it was on red 28 and I had lost. 

Trista just smiled at me and said, "Well you win some, you lose some right?" I agreed but I was pretty deflated because even though I assumed that the end result would be us having s3x no matter who won, I was no longer in control of when that was going to happen. After staring at Trista's chest all night, my cock wanted it to happen immediately. 

We stayed at the casino a little while longer, Trista telling me she wanted me to cheer her on as she played blackjack. She told me that was her first demand. She ended up winning $50 and we headed back to the hotel. At this point, my balls were aching from watching her work the room all night and her boobs almost spill out of her dress. 

Back at the hotel, in the elevator, Trista said to me, "so did you get enough glances of my chest tonight? I swear every time I looked at you, you were staring at my boobs." I started to apologize immediately but she doubted that I was truly sorry. When the elevator door opened I sheepishly asked if she was going to go to bed. She looked at me and said, "Would you rather I go to bed or go back to your room and suck your cock?" My eyes were wide as I couldn't believe my ears and I told her definitely back to my room.

I couldn't get the door to my room open fast enough. Once in the room, I threw my jacket on the bed, turned around and Trista grabbed my crotch. "Let's take this out," she said and she slipped down to her knees. I stood there; still a little tipsy from the drinks I had as she unzipped my pants and took my cock out.  "What a site" I thought to myself. Staring down at Trista hold my hard cock in her hands, being able to look down her dress as her boobs almost spilled out of her shirt. 

I watched as she took her lips and placed them around my cock and watched as my cock slowly disappeared into her mouth. She held my balls in one hand and stroked me with the other as she gave me a mind-numbing blowjob. I stood there for a 2 to 3 minutes, her squeezing my balls occasionally as her lips worked their magic. Occasionally she would squeeze my balls which caused me to moan out but I was not going to complain. 

"Does that feel good on your little cock?" she asked. I didn't even mind her demeaning comment at this point and just said yes.

All of a sudden she stood up, still holding my balls in her hand. "That's all for tonight," she told me, "remember our bet, you do what I say, and I am telling you, no cumming tonight. If these balls aren't as full tomorrow as they are now, that little blowjob will be all you get the entire time we're here. Do you understand?"

I nodded and she squeezed even harder, almost bringing me to my knees. "Good, I'll see you in the morning. I'll be stopping by at 9 am so we can go work, out so be ready. And remember, no cumming."

With that she let go of my now aching balls and retired to her room. I thought about relieving the ache in my balls but remembered her threat. Eventually I was able to fall asleep, my balls, full of cum, aching all night long. 

Day 2:

At 9 am sharp, Trista knocked on my door. I was ready to go work out like she told me and I had even listened to her and not masturbated. She came in wearing a pair of spandex tights and a zip-up sweatshirt. I had put on the tights she had seen yesterday with wind-pants over them, along with a similar spandex shirt I had on and a tee shirt over that. 

When we got down to the fitness center at the hotel, there were a few people but it wasn't exactly bustling. She immediately went to a row of elliptical machines, turned on her I-pod and began her workout. I went to a stationary bike a couple rows behind her and a few feet over. From there I had a great view of her ass in her tightly clad spandex tights as she swayed from side to side. I was definitely lost in thought as I couldn't wait to get my hands on that ass and finish what we started last night. Before long I felt my cock straining against the spandex I was wearing myself. Without realizing it, a half hour had past, and I was drenched in sweat. Snapping me out of my trance, Trista turned around and caught me staring at her backside and was walking towards me. 

"Enjoy the view?" she asked me. I nodded and was about to make an excuse when she said, "Ok good, time to give me a view now, off with the wind-pants." I started to stammer remembering what happened when I was on display yesterday and this time with more people nearby. "No sense in stalling, we're not leaving until you're in just spandex for a half hour on a treadmill, besides, I won the bet remember." 

I knew it was useless to protest, she would wait here until I did it and I really wanted to finish what we started the night before. I slipped off the wind-pants leaving only the skin tight spandex on. "Mmmmm very nice," she said, "are your balls still full?" I looked around to see if anyone else had heard her. I told her they were and that I had followed her instructions. "I knew you would," she said and she went back to her machine. 

Trista standing in front of me didn't help to tone done my hardness at all. I felt that everyone was looking at me, and everyone was noticing my hard cock. Realistically I knew that half the people there didn't care either way, most probably didn't even notice, but that didn't help at all as I felt fully on display. 

Mercifully, the half hour ended. Trista giggled as she looked at me in just the tights and said we were done and had to get going. Thankfully, she had allowed me to put the wind-pants back on for the trip back up to the room. Trista told me that she had made an appointment at the salon for both of us which started in a half hour. 

I showered and was ready to go to the salon when she picked me up. First was a massage, which we got side by side. We were lying next to each other, only a sheet over each of us and were waiting for the masseuses to enter the room when Trista made sure to tell me, "This massage does not have a 'happy ending'."

For the next 45 minutes, the masseuse did a masterful job. I was in heaven as she worked my muscles and was totally relaxed. For a brief while, I was even able to forget that lying on the table next to me was Trista totally naked underneath her sheet. Of course, every once in a while I had to take a look over at her table to see if there was any skin showing. 

Once the massage was over, Trista told me that she was going to get a manicure and pedicure. She asked what color she should get her nails done in. I suggested red. "A little slutty, don't you think?" she asked. I shrugged and said yes but she asked. She said fair enough. She told me she had set me up for some waxing, saying that I had way too much hair on me last night. 

I must have looked at her skeptically because she reminded me that I had lost the bet and that it'd be growing back by the time we went home anyway, so just go with whatever the esthetician says. She also explained to me how much more she likes smooth skin on a guy. No sooner had I said ok than the esthetician came in and introduced herself, showing me to a different room. Once there, she explained the process and what was going to be done. When she said complete hair removal I asked what she meant by that. She told me that Trista had set up a complete hair removal from the neck down. 

"Shaven legs?" I thought to myself. I wasn't too sure about this. 

The esthetician sensed my skepticism and assured me that the procedure was not uncommon for men, and was increasing in popularity. She asked me if I liked feeling smooth legs on a woman and when I said yes, she asked how this would be any different. She also reminded me that Trista must like it since that is what she set up. 

I decided in for a penny in for a pound and as Trista said, it will be growing back by the time we were done with the trip anyway. 

The esthetician started with my back and then my chest. It wasn't too bad. It hurt some but nothing like in that movie the 40 year old virgin. When she was working on my groin I found myself growing aroused yet again and was embarrassed, but she assured me that it actually helped to get all the hair off. Anytime I started to go a little soft, she seemed to accidentally brush against my cock, making it spring back to life. I'm not sure if that was truly an accident but she apologized each time. 

To finish, she explained to me that I had to get on my hands and knees so she could do my ass. I felt very exposed in this position and while it didn't take all that long, by the time I was done, there was a little pool of cum on the table beneath me that leaked out of my cum-filled cock. She noticed it and giggled a little, but was a professional about it all. 

The whole procedure took a little over an hour and I met Trista and her new bright red nails out in the lobby of the salon. She was reading a magazine and asked as soon as she saw me, "How does it feel to be totally hairless?" More than a few people looked up and the girl at the reception desk couldn't stifle her laugh. My face turned red, but I answered that I was surprised that it felt really good and I liked it. 


Working with Trista Ch. 02



This is the second chapter of an on-going story of working with Trista. All feedback is welcomed. 

Day 3: 

That morning I was awakened as my phone rang; Trista was calling me telling me it was time to get up. She said that she would be over shortly. I hoped it was to let me out of the chastity device. That moment couldn't come soon enough, and neither could I! 

A few minutes later Trista knocked on my door. I opened it, and she was dressed in a pair of spandex shorts and a zip up workout vest. My cock tried to stiffen at the sight of her outfit. It didn't happen. She smiled and reached for my boxers. She fondled me, feeling the device, "I see you still have it on. Is it still working do you think?" she said will a bit of sarcasm in her voice. 

It definitely was still working especially as I watched her in the skin tight outfit. She told me, "Well I have good news, because it's important to keep up your exercise routine I'm going to take off this device for your workout. But don't you dare think of cumming. Also, after the workout it goes back on each day. Sound good?" 

At this point, I figured I'd best take this offer as I just wanted to get out of this thing, no matter how brief, and there was always the chance she'd change her mind. She kneeled down to unlock the device and immediately my cock sprang to life. It was fully hard in a matter of seconds just from being released. 

"Ok go put on your tights," Trista said, "we're going to go work out."

I couldn't go like this I tried to explain to her, but she was insistent that we were going in just the tights and nothing more. Finally she said, "Ok, I've heard enough, today is the last day you're wearing black tights. I'm going to go shopping today and get you different colors, so your little hard cock will be even more noticeable." At that point I quit protesting, figuring I could only dig myself deeper into a hole. 

The workout went as expected. I was hard almost the entire time, from my room, the elevator trip downstairs, throughout the workout, back up the elevator and back into my room. Watching Trista in her skin tight clothing certainly played a large part. By this time, my balls were aching and it wasn't even 10 am yet. I felt this could be a long day. 

"Time to put your device back on," Trista said as we returned to my room. She went to the bathroom, and told me to come in with her. She then lowered my tights and touched my rock hard cock ever so lightly. I moaned instantly, wanting so badly to cum. She then got her hands ice cold under the water before returning to my cock. Immediately it softened and she locked the device back on me before I knew it. Oh the frustration. She then pulled up my tights and patted my ass. 

Trista then stood up and unzipped her workout vest, revealing a very thin sports-bra that barely held her breasts. She took my hands and put them on her chest, my cock now straining against the device again. 

She led me to the bed and said, "I wasn't planning on doing this until later but I did tell you I was going to make use of your tongue again. Just watching you struggle and knowing I control your little cock gets me so wet." With that she slipped off her spandex shorts, pushed me back on the bed, and climbed up me, straddling my face with her wet pussy inches from my mouth. 

"Lick me slut," she said as she grinded her pussy into my face. I brought her to quite a few orgasms over the next hour. My face was covered in her juices and my tongue was sore by the end of it. Trista finally crawled off of me and said that it was great. She then patted my still sensitive and aching balls and told me she wanted to go down to the pool and that I should get my thong on. 

She stood there watching me as I put on the thong. She said it'd be ok if I put on the board shorts today, which I thanked her for. We then went to her room and she went into the bathroom to change while I waited on the bed. She came out of the bathroom in a white bikini with some sequins on them. She looked magnificent. It was probably a good thing she kept the chastity device on me at this point as I would be rock hard at the pool the entire time looking at her. 

We went down to the pool, and once again I was made to remove the board shorts immediately. I applied the lotion while having to half stand up again. When Trista was to put some on me, I was made to stand up and she slapped my ass quite hard which drew snickers from some of the people sitting near us. 

After an hour or so, Trista told me that she wanted to go shopping. The pool was getting rather busy with people, so it was time to go. Back in our own rooms we had each showered and changed and Trista stopped by my room to pick me up. She was dressed in a tight top and jeans. She looked very good in such a simple outfit. 

When I asked her where we were headed, she said she wanted to make a few stops. Our first stop was an athletic store. We went in and she told me that I could feel free to browse around for a while. About 15 minutes later, Trista came and got me and told me she had some stuff for me to try on. The first was a pair of running tights similar to the ones that I had worn the past two days while working out. However, instead of black, this pair was a very bright royal blue; something that would sure to be noticed. Also in the pile she handed me was a red spandex short sleeved top. The final item was a sports-bra. I handed this back to her saying I think you messed up the piles. 

She just smiled and said, "No I want you to try that on too. Don't worry no harm in just trying it on. But I want to be able to see for sure so don't take it off before you show me." 

I slipped the sports-bra on in the changing room, shaking my head at the absurdity of it all. I also put on the spandex tights and the spandex top. My cock was definitely pushing against the device wanting to be free at this point. 

When everything was on, I opened the door to the dressing room, there were three dressing rooms in a little area and I saw Trista looking at some shirts, standing away from the dressing rooms. I got her attention and told her to come take a look. 

She told me to come out to where she was, away from the "safety" of the dressing rooms. I shook my head no but she made a face that seemed to suggest that this wasn't up for any sort of debate. 

Much like crossing the street I peered both ways before exiting the dressing room. "Oh hurry up," Trista said exasperated. I took a deep breath and went out, the sports-bra clearly visible underneath the skin tight shirt. 

"Oh I like these. Very nice and shiny," she said as she ran her hands over my shoulders and down my back. She grabbed my chest and said, "How do you like this sports-bra?" I told her it felt funny and she just laughed and told me it looked good. Her hands continued down my back over my ass. She told me to turn around and there she slapped my ass. It was loud enough for others to hear because as I looked up I noticed others had too in my direction. 

"That is for making me wait. You have 9 more of those coming as punishment. I doubt you want it administered here so I will cut you a break, ok?" I readily agreed to that, no way did I want her spanking me in the store where others could see. She told me to get changed and to just leave the clothes in the dressing room and meet her up front in 5 minutes. 

I changed out of the clothes, my ass stung a little bit from her slap. She had some good power behind that one. I met her at the register; she was checking out and had 2 or 3 bags. I asked her what she got and said, "Don't worry about that, none of your concern."

As we pulled up to our next stop, I recognized it immediately as it was the adult store where the device was put on my cock the day before. Bolt was behind the counter once again, he laughed at his own joke when he asked me "how's it hanging."

When asked what brought us in today, Trista explained that she was looking for something to "keep me in line."

Bolt laughed a little and said, "Well the chastity device should be doing just that, but we have a few other things that might work."

We walked through the restraint section; Bolt showed us cuffs, some rope and a variety of things in the bondage section. Trista found a couple of Velcro cuffs that had a piece of rope attached so it could be tied to just about anything or to each other. It was pretty slick actually. 

Next, Bolt took us through an array of whips, paddles, crops and floggers, showing Trista how each one works and how to properly use them to get the most out of them. And when I say that he took "us" though, I mean Trista, I wasn't much more than an afterthought and my opinion on things wasn't being asked at all. Trista couldn't decide between a crop and a paddle so she picked up both. 

Bolt, being the salesman he is, started showing us the gags. It is amazing how many different kinds there are. He said that if Trista was going to use the crop or the paddle correctly, she may want one of these. She eventually chose a traditional ball-gag over a penis gag thankfully. Like I said; a good salesman. 

Another couple, about in their late 30's came into the store and Bolt said hello to them before turning his attention back to Trista and explaining all the benefits of collars and their many uses. I didn't know how useful this was, but Trista picked one out regardless. It was black leather, had multiple D-rings on it, and could be locked on with a small lock. As far as my limited knowledge of collars went, it looked like a good selection. 

Bolt asked if we needed anything else and Trista said she thought this should be enough for today, though we may be back tomorrow for something else. Bolt just laughed and said that'd be just fine. He rang us up and then said to Trista, "As you know, some of this stuff once used you can't exchange, but some, like the crop or paddle, that isn't a problem, same with cuffs. So if you want to try them out before you go, you can certainly feel free to do so." 

Trista asked for more information and Bolt pointed her to where they had applied the device earlier by the dressing rooms or an open spot in the middle of the store. "We're sort of open-minded here if you hadn't noticed," he laughed. 

Smiling Trista turned to me and said, "Yes we will try these out here, that's a great idea. He already earned a punishment earlier this afternoon so this will be a good time to administer it." To say I was against this would be an understatement, but Trista whispered in my ear, "Any whining about this will only make it worse, trust me."

I knew she wasn't kidding and so I followed her and Bolt to the area in the middle of the store, because of course, Trista couldn't pick the more private spot of the two. Once there, she asked Bolt his opinion and they whispered back and forth for a bit. Finally Trista turned to me with a grin. 

She told me to take off my shirt and as soon as I complied she put the cuffs on my wrists as well. Bolt stood on a stool and tied the attached rope for the cuffs to a bar running overhead so my arms were above my head and I wasn't going anywhere. 

Bolt standing on the stool got the attention of the other couple in the store and they came over to see what the commotion was all about. Trista introduced herself to them, explaining that she was going to test out her new purchases. She invited them to watch, though it looked like that was what they had planned on doing anyway. 

The couple introduced themselves as Jake and Alana. Jake was a tall guy and was pretty well dressed while Alana was short, very pale with long brown hair, but had curves in all the right places. She had on black high heeled boots too which always catch my eye. When Bolt was finished tying me to the overhead bar, he stepped back and said to Trista, "he's all set." Trista walked up to me, and I pleaded with her not to do this in front of these strangers. She just smiled and told me to open my mouth as she forced the ball gag in. She strapped the gag in place and then began to go to work on my zipper. 

In a matter of moments I was stepping out of my jeans and boxers with assistance from Trista, leaving me fully nude now in front of all of them. Alana commented on the chastity device, and Trista gave Bolt the credit for recommending it. I was utterly embarrassed obviously and just wanted this to be over with as soon as possible. But I could feel my cock wanting to get hard as it strained against the device, being on display in front of everyone. 

"Well," Trista said, "let's get this show on the road." With that she brought the paddle down hard against my ass. I wasn't expecting it at all and let out a yelp into the gag. I immediately felt my ass cheek redden exactly where the paddle had hit. 

Trista let me have 4 more on the same check, each one hurting more than the last. She switched sides and gave me 5 on the other side. By this time I had had enough as my ass felt very warm. She rubbed her hand over my backside telling me she liked the way my ass felt all hot and looked when it was all red. She said, "I was only going to try this out, but I think now we're going to do a lot more."

Turning to Alana, she offered her the paddle asking her if she wanted to try. Alana, smiled, shrugged and said, "Why not."

She stood behind me and laughed at her line of "This is going to hurt you much more than it will hurt me." With that, she proceeded to give me 10 smacks on each cheek. I gritted my teeth into the gag, as each blow rang down. I could feel my backside growing warmer. 

Then I heard exactly what I didn't want to hear. Trista said, "Do you want to try Jake?" I was not at all excited by this prospect. Well let me rephrase that, while my cock was straining against its cage, I knew what was coming was going to hurt like hell. Jake of course accepted Trista's offer and Trista thought that another 10 total would be just right. After the first one I screamed into the gag, my ass hurting immediately as he must have put all he had into it. I opened my eyes, and saw Trista smiling deviously back at me. Five more and I had some tears welling up in my eyes. After what seemed like forever he finished up the 10 swings and sort of laughed as he said, "Wow, that's pretty red," in reference to my ass. 

Trista walked around me and inspected the damage done behind me, "Oh my," she said, "that looks like it hurts. Well luckily for you, we only have to try the crop out yet and then we'll be done. I heard Alana laugh and Jake say to himself something like, "oh man."

Trista grabbed the crop and walked around me, she asked if I was enjoying myself and when I shook my head no, she tapped the crop against the steel cage holding my cock and said, "It seems this little guy wants to straighten out though. That tells me you're enjoying this quite a bit." And it was true, for some reason my cock was trying to get hard. Not sure if it was the actual beating my ass had taken, being tied up, or the humiliation of this happening in front of other people but it was true, my cock ached to be free, and my balls definitely were full. 

Trista stopped tapping the cage, and tapped my exposed balls. She didn't do this very hard, really nothing more than a light tap, but I had been turned on for so long now and with no relief, the slightest touch was excruciating. My knees nearly buckled as she tapped my swollen testicles. "Oh my, looks like I will have to revisit that location soon," Trista said as she smiled at me. She went behind me and then said, "Ok my little slut spread those legs, and you have only 10 from me using the crop." 

I spread my legs, still delirious from the perfectly placed tap she had given me moments ago. I soon snapped out of it as the crop cut through the air and landed perfectly on my backside. I yelped into the crop. While Jake definitely swung the paddle harder, Trista was at least able to match that with this device. With the paddle, everyone had taken their time and made sure that I was cowering in anticipation of the next blow. Not this time, Trista quickly administered all 10. It was quick but very painful. She put her hands on my ass and said, "Oh I love this warm feeling, we're going to have to try to keep it like this."

Trista and Bolt un-cuffed me and I was told to get dressed. Alana & Jake thanked Trista for the show and they made small-talk until I was dressed. When I was ready to go, Trista said her goodbyes to Alana & Jake, thanked Bolt and we headed to the car. I sat down in the car, very gingerly. 

We got back to our hotel right around dinner time. I was still moving gingerly and in my room Trista ordered me to remove my pants so that she could see how red my ass still was. She smiled when she saw how it still looked. She showed me in the mirror and was very pleased with the handiwork.

She told me to relax and get ready for dinner; she wanted to go shower and get ready. I was exhausted, as this had been a pretty full day for me and I used the downtime to take a little nap. 

I was ready to go when Trista knocked on my door for dinner. I opened the door and as usual I wasn't disappointed. In what is commonly referred to as a "little black dress" Trista looked wonderful, and as seemed to be the theme of her outfits, her breasts seemed almost destined to have some sort of wardrobe malfunction. 

Once again, Trista wanted to see my backside and ordered me to remove my pants and boxers. She was a disappointed that a lot of the redness had faded, even though I tried to explain to her that the tenderness lingered. She told me as much as she'd like to make sure it was red for dinner she had a better idea. She took my hand and walked me over by the window, sat on the desk and pushed me to my knees. She leaned back, spread her legs, and said "you know what to do." I was pleasantly surprised to see she was not wearing underwear, and was anxious to get to work. She grabbed my hair and shoved my head between her legs. I started with my tongue, and added a finger to her wet pussy. For the next half hour, I brought her to multiple orgasms, my cock straining against my restraints. She pushed me back onto the bed, and removed her underwear and climbed up on my face. She said I knew what to do and for the next half hour I did exactly that bringing her to multiple orgasms. 

When she had had enough she pushed me away and tossed me some underwear saying, "Here, since I'm not wearing these, you should tonight." I asked her why as obviously I wasn't all that interested in wearing women's underwear. She said that I had a choice, I could either wear her red thong, or she would redden my ass with the paddle until it was the same shade. It was an easy decision as I slipped the thong on. 

Once it was on, I looked up right as Trista was taking a picture with her camera phone. "Very nice," she proclaimed, "now finish getting dressed and let's go." 

I dressed and we went out to dinner to a nice restaurant. The thong of course didn't feel natural but I was making the best of it. As you can expect, every time I managed to forget about it for a few minutes Trista would remind me about it. Either asking how it felt, or if I liked the look or even saying that she wondered what the other people in the restaurant would think if they knew. All of this talk started to get my cock going again, or at least as much as it could while being stuck in the restraint. 

Trista made a point to flirt with the waiter, Chaz, in front of me all throughout dinner. She kept saying she was thinking of asking for his phone number and bringing him back to the room. Since my cock was all locked up she said I wouldn't mind. She added insult to injury when she said that he probably had a bigger cock to satisfy her anyway. 

When the check came, Trista actually did ask if she could have Chaz's phone number who gladly gave it to her. He smirked at me as he wrote it down. 




Working with Trista Ch. 02



After dinner, we headed back to the hotel, Trista said the entire dinner got her riled up and she needed some relief. Back in my hotel room, she ordered me to strip down to just the red thong. She eyed me over and said that she really loved that look but that it seemed to be missing something. She slipped off her dress and then removed her bra, leaving her totally naked, and leaving me with my tongue hanging out as usual. She then told me, "This is a set, the bra goes with the thong," as she put the bra on me. 

She stepped back and smiled as she looked at me in her bra and thong. "That looks so nice. Though red is a little whorish. But no matter, you're dressed for the occasion. Now my little whore, let's get down to business." She had me lay on the bed, and she grinded on my face for the next 30-45 minutes. She came multiple times. She paid a lot of attention to my nipples too, squeezing and pulling at them through the thin bra. My cock was trying like mad to escape from its imprisonment. Being dressed up and treated as a whore was really having an effect on me. 

When Trista finally let me up, she was covered in sweat and looked so sexy. My nipples were aching as were my balls. I was very excited when Trista said, "Now it's your turn for some attention." I thought the torment of the past two days was finally going to pay off. 

She wanted me to kneel on the bed, with my ass facing the door. I got into position. The red thong and bra the only things I had on. She lightly ran her hand over my exposed ass, and said, "Now my dear slut, hold this exact position. I have to run to my room to grab some things, but I will be right back down before you know it. Don't move if someone comes by and looks in here. I want them to get a clear view of exactly the type of gal you are." 

I watched over my shoulder as she got dressed and then propped the door open with the doorstop and then went to her room. It seemed like an eternity she was gone. Every time I heard a voice, I started to look over my shoulder but I didn't want to actually make eye contact with anyone so I would quickly put my head back down. It ended up being about 15 minutes that she was gone. I heard two giggles and a whistle at different times. Each time my face turned about as red as the bra and thong set I had on. 

Trista entered the room and was pleased to see I was still in the same position she left me. After asking me the details about the time she was gone, she was quite pleased with how it had worked out. She then looked me over and said, "You know you look so good in that outfit, we're going to have to get you some of your own tomorrow as I can't have you wearing mine all the time."

She asked if I would like that and when I stammered, she got me to admit that I was turned on when others saw me in the lingerie. "Well that seals it, if you were turned on, then we definitely need to get you your own outfits. That's tomorrow though. Tonight, I want to use the toys we got again, your ass looks so good in red; I want to see if I can get it to match. Get on your hands and knees again."

This wasn't exactly what I was hoping for when she said that I was going to get some attention, but I obediently turned around. I heard a couple of clicks and I turned and saw Trista was taking a couple of pictures of me in this position. I just hung my head in shame, hoping she would never show those to anyone. She came up behind me and said, "Ok slut, how many do you think you deserve?" When I told her that I had been very well behaved and did everything she asked she said, "That's true you did, but part of this is to make sure that you continue to behave as well. How about we give you a good 20 and then we can move onto more fun things?"

That seemed fair and a lot better than I was anticipating, and what I had gone through earlier in the afternoon, so I readily agreed. She started on the right side and brought the crop down on one side and then on the other side, alternating back and forth. It seemed that my backside wasn't as healed up as it appeared from just looking at it, as these hurt a lot more than they had earlier in the day. Trista finished all 20 and my ass was very warm. She giggled and said it was a very deep red and actually did match the red thong quite nicely. 

She ran her hands over my ass, feeling the heat it was giving off, and then reached between my legs, and started fondling my aching balls. Occasionally she would run her hand over the chastity device too, just to emphasize the control she had over my cock. "Would you like to see me masturbate," she asked, "maybe use a toy as well? Sort of get me in the mood for more to come?"

I couldn't say yes fast enough. Trista smiled and went to the bag she had brought to my room. She pulled out a purple dildo and brought it over to the bed and she began to undress once again in front of me. I was still on my hands and knees as told me to hold that pose as I watched her strip once more. When she was fully disrobed she sat in front of me and spread her legs, one on each side of me. She took the dildo in her hand and said to me, "Get it wet," as she brought the dildo up to my mouth.  

I just stared at it, frozen, a million things running through my mind. First and foremost the thought of "Um no," called out to me but quickly my mind raced to other things such as I was already dressed in a bra and thong it seemed a natural progression. And if I did this, maybe I would get some relief for my aching balls. If I did this, I would get to watch Trista masturbate with it. As all these things were running through my mind I once again felt my cock straining against the chastity device it was encased in. 

I bent my head down and slowly took the tip of the dildo into my mouth. It was a good 8 inches long and about an inch wide. After I had the tip in my mouth Trista whispered, "That's it, you're doing great." She pushed a little more into my mouth and she whispered again, "You're doing great, pretend it's a real cock: suck on it like you would a real one."

Well speaking of real cocks, mine couldn't have tried to escape its cage any more than it was right now. My balls were aching and I couldn't have been more turned on than I was at this moment. 

Trista continued inching more of the dildo into my mouth, encouraging me with each inch. Of course her encouragement consisted of calling me a cock sucking whore and mentioning that this dildo was much bigger than I was. But in the moment, it did the trick and turned me on. Occasionally she would take a picture of me with the dildo in my mouth as well.

Finally, she pushed the remainder of the dildo into my throat causing me to gag on it. She giggled and said, "You have to watch out for that, a real cock, with a man on the other end, won't go as slowly. You have to be ready." I absent mindedly nodded as she began to withdraw the dildo from my mouth. 

"Now that you got this cock nice and hard, do you want to see me take it?" Trista asked. She knew the answer but I nodded immediately that I did. With that, she laid back, her glistening pussy on display and she slowly slipped the wet dildo into her. She let out moans as she adjusted to its size, and soon after began to slowly slide the fake cock in and out of her. It was quite a site to see her naked on the bed, her legs spread, her gorgeous tits moving with each stroke of the dildo pumping in and out of her. Finally, she reached the point of cumming and let out a loud moan and her entire body shuddered. After bringing her to multiple orgasms with my tongue the past couple of days you would think that it wouldn't have been as intriguing to see, but it was a real thing of beauty; this being the first time I was not preoccupied and could just watch and admire her. 

Once she regained her composure, she sat up, a big smile on her face. "That felt great," she told me. Withdrawing the plastic cock from her pussy she brought it up to my lips again and said, "Now you get to clean it off," as she pushed it between my lips.

She was much less gentle this time around; forcing the dildo into my mouth and making me gag a few times before she deemed that the toy was clean enough. "I'm sure you wish it were a real cock you were cleaning my juices off of, but not bad for your first time. I think you should sleep in this bra and thong, it looks so sexy." I groaned as at that point I knew I wouldn't be getting any relief once again. 

Trista retired to her room, leaving me in her bra and thong, exhausted, humiliated, aching and honestly somewhat questioning my sexuality after what just happened. There was a lot going through my mind and it took a while for me to finally fall asleep.



Working with Trista Ch. 03



This is the next day in my experience of working with Trista. If you haven't read the prior chapters, please do so. Don't hesitate to contact me with feedback. 

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Day 4: 

I awoke to the sound of my phone ringing; Trista of course was on the other end. She told me to have my stuff packed up, that I'd be switching rooms. She explained that instead of us having two separate rooms we may as well upgrade and get one nicer room since she was spending a large majority of her time in mine. I wasn't going to argue with that, these Vegas hotels have some very nice rooms. 

I also thought that maybe if we were sharing a room, I might have a better chance of getting some relief. 

Each morning my balls were still sore and throbbing from being so full, but it was so much better than at night. It was like they got some rest themselves as I was sleeping. Trista had told me that I had 20 minutes to pack before she got to my room. She told me to pack up everything but the clothes I had on. When I reminded her that I still had on her bra and thong from the night before, she said that's fine, to pack everything up but what I was wearing. 

I didn't like the sound of that but I wasn't in much position to argue, nor did I have time to put much thought into arguing. I had a lot of packing to do. 

I finished just in time, as I heard a knock on the door. I confirmed via the peephole that it was indeed Trista and let her in. She came in carrying a plastic bag and immediately looked me over. She had on black spandex tights and a red zip up vest. (Naturally I looked her over too in that outfit.) 

"Well how did you like sleeping in my lingerie," she asked. I admitted that the outfit was and is a turn-on, but also said I had a fitful night of sleep and mentioned the reasons why. She seemed sympathetic as she listened although she made no promise of any sort of relief coming my way anytime soon. 

She asked if I had packed everything and I told her that I had. She dug out my tennis shoes and a pair of socks from my bags as there was another knock on the door. Trista told me to sit on the bed and not to move. It was a bellhop from the hotel staff who was there to move my bags. Unfortunately for me, Trista let him in the room as I was sitting on the bed. He saw me and tried to stifle a mocking smile but couldn't totally suppress it as he saw me sitting there in Trista's undergarments. Trista noticed his laugh and said, "I suppose you see something like this a lot." Ramon (whose name I learned via his nametag) sort of laughed and said that not as often as people think. Trista then introduced herself and said that since it doesn't happen often he should have a story to tell so she made me stand up and turn around so the bellhop could fully see me. When Trista asked what he thought, Ramon said, "he looks pretty good in it actually, but not really my type." That made Trista laugh and she thanked Ramon and asked him to bring the bags up to our new room telling him we would return the keys to the front desk soon. 

My face was now as red as the lingerie I had on, and I was growing concerned about what it was that I exactly was supposed to wear now that all my clothing had been removed by Ramon, except for what I had on and the shoes and socks Trista had dug out of my bag. It would certainly make a strange ensemble I thought. 

My question was answered immediately as Trista pulled out of the bag a pair of royal blue spandex tights and a long sleeved red spandex shirt similar to what I had tried on the day before. 

I started to protest that I couldn't wear this outfit, but Trista cut me off. "Look, you're going to take off the lingerie, we're going to take off the chastity device, you're going to put on nothing but spandex, we're going to go work out, you're going to be hard the entire time, everyone will see your hard cock in the spandex, then we're going to go our new room and we're going to put that little cock of yours back in the cage where it belongs. Is that understood?" 

I answered, "Yes Ma'am." At the present time, I didn't have many bargaining chips. All of my luggage had been moved, the only clothes I had were the ones I was wearing and Trista didn't seem to be open to any type of discussion on the subject. 

I followed her instructions. Immediately my cock sprang to full attention as soon as it was released and remained that way for basically the entire workout. That includes the trip down the hall and the elevator and past the 30 or so people we passed on the way to the workout room. It also includes the 6 or 7 people in the fitness center. You know how they have those Viagra commercials that if you have an erection that lasts four or more hours to contact a doctor? That's what I felt like. 

When the workout finally ended, which was about an hour later, we headed back up to what I thought was going to be our room. Instead we headed to the front desk. It turned out that "conveniently" we had to return our keys from our previous rooms. So I stood there as Trista conversed with a cute young gal at the front desk named Kristin. I stood there nervously. On full display, I didn't know if I should leave my back to the rest of the lobby allowing everyone to see my ass in the royal blue spandex or to turn around and cover my cock with my hands crossed in front of me. Neither seemed like good options as I tried to avert the humiliation of being in that outfit in the lobby. I wasn't paying much attention to Trista's conversation when I suddenly saw Ramon coming up to the front desk. "Ah, Ramon was so helpful this morning," Trista told Kristin. I felt my face become totally flushed as Ramon received Trista's praise. I knew he was going to tell others what he had seen earlier if he hadn't already done so.

Finally Trista wrapped up her conversation and we got directions to our new room. I was very happy to finally get out of there. As we walked down the hall to the elevators, Trista kept the pressure on me, telling me things like people were probably staring at my ass or that the people we just passed looked down at my cock or that Ramon was telling Kristin about what he had seen earlier. I have to admit, the mental games she was playing certainly had an effect. While they were frustrating, it was such a turn-on at the same time. My cock had been hard for about 2 hours now and it wasn't going down until she wanted it to. 

We finally arrived back at our new room and before I was able to look around and admire the upgraded suite, Trista led me immediately to the kitchenette. There she had a bucket of half ice, half cold water on the counter. She had me lower my tights and she grabbed my cock in her hand. She stroked me up and down very sensually and whispered to be sure not to cum no matter how much I wanted to or I would be sorry. But boy did I want to. 

Her hand then moved to my balls and she took them in her hand and squeezed, gradually increasing the pressure. I moaned. She smiled and then slowly she dunked my cock into the frigid water. Trista then knelt down in front of me and put me back into the chastity device as soon as I was flaccid enough to do so. "Now you can look around the room," she told me as she went to shower.

I did look around the room, and it was a much nicer upgrade that the one I'd had before. Instead of my window overlooking the pool, there was now a little balcony off a patio window. We were 6 stories up, but below us was the strip. It was a pretty sweet view. The entire room was wide open, similar to what I remember seeing in a few movies with the floor to ceiling windows and the balcony that overlooked the strip. The only part that was separate was the bathroom. Also, we had a kitchenette, a couple of couches and a huge king sized bed. I liked that, I figured worst case, with only one bed; I could at least fondle Trista as we slept. Always the optimist I am. 

Trista came out of the shower stark naked and into the room. She told me that we had a big day planned and that we had to get going, but first I had something I had to do. She had me kneel before her and she grabbed my head and pulled it into her pussy. I knew what to do from here and my tongue went to work. She ran her fingers through my hair as I ran my hands up and down her legs as my tongue darted all around her pussy. When Trista caught her breath after cumming she said, "You lick pussy almost as well as you sucked that fake cock last night. I am beginning to wonder which one you like best." With that she told me to shower quickly so that we could get going. 

In the shower, I watched as the water cascaded down my waxed legs, looking at my cock in its chastity device, and my mind kept wondering why in the hell I kept getting so turned on. I never before had any interest in any of this stuff, why was it turning me on so much now? And of course, as I kept wondering and replaying the past few days in my head, my cock tried to stiffen and my balls began to ache even more. I quickly flipped the shower to cold and decided to give the old cold shower remedy a chance. At this point, I was so frustrated with not being allowed to cum that I would try anything. 

The cold shower didn't hurt at all but it didn't help as much as I would have liked. Trista told me to quickly get dressed. Getting to choose my own outfit this time, I went with jeans and a tee shirt. 

In the car, I asked Trista where we were going and she told me we were heading out shopping. We pulled up to a little strip mall and went into a boutique that upon walking in seemed to specialize in lingerie. 

As we walked in and were greeted by a very cute clerk who introduced herself as Kim. Naturally, when Kim asked what she could help us with, Trista said that she we were there looking for lingerie, however I think I was more surprised than Kim was when Trista told her we were there for things for me to wear. 

I looked at Trista, and she said in an even tone, right in front of Kim, "Well we can't have you always wearing mine like you did last night." My face turned as red as could be as Kim giggled at that comment. Trista then added, "He really seemed to like it" with a wink.

From that point on, it didn't seem that I had much need of being there, as Trista discussed with Kim exactly what I should get and didn't include me in the conversation at all. Occasionally, they would hold something up in front of me but by and large I was forgotten for much of the next hour. That was just fine as I was embarrassed as could be and my balls were continually aching as I kept picturing myself in the outfits they were looking at. 

Finally, all the outfits were picked out and Trista called me over and held up three outfits: a black teddy, a red chemise with matching thong and a black with white pinstripe baby-doll with a matching thong. Trista asked, which outfit I liked best of these three. I looked them over and selected the pinstriped one. 

Trista then handed me the outfit, and said, "Ok, here you go, try it on." When I started to stammer she also handed me a package of black thigh high stockings that she said would complete the look. I looked at Kim who just had a smile on her face as Trista pushed me into the dressing room. 

As I stripped down, my heart was racing, my balls were aching and my cock was testing its bonds. I put on the thong first, and then I began to put on the stockings. I have to admit, that was quite the sensual experience, and the feel of the stockings against my smooth legs was definitely pleasurable as I was testing the cage once again. I finally slipped on the baby-doll top as Trista was telling me to hurry it up. 

When I was ready, I opened the door, and peeked out seeing Trista still talking to Kim. I got their attention and even though there was no one else in the store, I didn't think they wanted me to go over to them. I was wrong. 

"Come over here," Trista demanded. I walked over, feeling very much on display as they had me turn around a few times. My cheeks were burning with humiliation. They both said I looked very nice and to which I thanked them. Kim mentioned that it seemed I filled up the thong quite a bit. Trista laughed and explained that that was definitely not the case. She told me to pull down the thong to show Kim the chastity device I had on. 

Both Trista and Kim knelt down in front me as Kim inspected it and Trista took her through the highlights of the device, namely that she held the key and I couldn't get hard at all. Trista then explained how she basically owned my cock and could do with it what she pleased. With that she wrapped her hand around my still exposed balls and squeezed, gradually tightening her grip until my knees began to go weak. "Isn't that right slut?" she asked me. 

I couldn't form any words as she crushed my balls in her hand but managed to get out a nod and she then released them from her grip. She told me to change back into my regular clothes but to leave the thong and the stockings on which I did. Trista then had me thank Kim for all her help and we headed to our next stop. 

Our next stop was at a shoe store. This wasn't your typical Payless place, this specialized in very high heeled shoes, that I believe this store could be best be described as a place where strippers would shop for their shoes. Upon entering, once again we were greeted by a clerk; she was a short brunette who introduced herself as Heather. When she asked us what we were looking for Trista told her that we were in the market for some "eye-popping fuck me shoes, something that leaves no doubt." Heather giggled a bit and said she had plenty of options as she led us across the store. 

We arrived at a large wall of high heeled shoes, almost all at least 5 inches. Trista eyed the wall before selecting a black strappy pair, with a 5 inch stiletto heel. Heather complimented her taste and asked what size she was. Trista smiled and said, "oh no dear, these aren't for me, these are for him." As was becoming standard for me, I could feel my face blush as I could also feel myself strain against the cage once again. When I told her my shoe size she got out a pair for me. Trista told me to take off my shoes and socks to try them on. That was when I was reminded that I had left the thigh high stockings on and now my nylon covered feet would be seen. Trista must have noticed my hesitancy and decided to explain, in full detail to Heather exactly why I had nylon covering my feet. "We just came from a lingerie store, last night he was wearing mine and while he looked quite nice in them, I felt it would be better if he had his own and he wanted to keep the stockings on." Heather had a sly smile on her face as I was putting the shoes on. My jaw dropped when I heard Trista ask Heather if she wanted to see some pictures. 

Trista then took Heather through picture by picture of the previous night and all the pictures she had taken of me in her lingerie complete with the pictures of me sucking on the dildo. I was mortified. 

Finally I had the heels on and I tried my best to stand up. Trista told me to walk down the aisle so they could see how they looked. I went slowly, making sure that I would not topple over and putting one foot in front of the other. Trista laughed as Heather mentioned to her that I appeared to be a natural in heels and said I was "workin' it." Trista loved them on me, and thought they looked great. So great in fact, she told Heather that I would just be wearing them out to the car. When I started to protest, Trista said we parked right in front of the store, at worst people who I would never see again would see me, what would be the big deal. I relented and after we paid, I did a little walk of shame out to the car in my new high heels. Trista however wouldn't let me in the car right away, she made me stand outside the door, pleading with her to let me in until an older couple walked by and saw me standing five inches taller than I normally would be in my new heels. 

In the car, Trista told me that she had a couple stops left. We had an uneventful (surprisingly) stop for a wig for me. Luckily Trista had allowed me to switch back into my normal shoes before we went in. For our final stop we pulled up once again to the sex toy store we had visited the previous day. Trista told me to just wait in the car, she was picking something up. She was inside for no more than 5 minutes before coming out with a large plastic bag that seemed very full. When I asked what she had all gotten, my fears were confirmed when she told me to be patient and that I would find out soon enough. 

We arrived back at the hotel and went back to the room and she told me how much fun she had had with me today. She wanted to see how I would look in my new outfit. She told me to go into the bathroom and to remove my clothing and to come out in the black bra and thong set, complete with the wig, stockings and heels. 

I went into the bathroom and stripped off my normal clothing. I put on the outfit as directed. When everything was on, I looked at myself in the mirror. I had to admit, that I thought I looked pretty good. Not a supermodel by any means but from across a room I could certainly be mistaken for a woman. I turned around and admired my ass in the mirror. I was amazed at how different it looked with the heels on. Once again, I thought I looked pretty good all things considered. The more I admired myself the more my cock tried to strain against the cage it was still locked in and the more my balls started to ache once again. I didn't know where this was going but I had to admit that it did seem I was being turned on by it all.

I opened the door to the bathroom and walked out, looking for Trista. She was sitting at a table across the room with a robe on sipping on a glass of wine. "Come over here and let me see you," she told me. Once again, I slowly walked across the room, trying to keep my balance. I was watching where I was walking and I heard the click of her cell phone taking a picture of me in this outfit. I looked up and she just smiled. "You looked so cute I had to have a picture," she said. 

Once in front of her she was glowing, telling me she definitely liked what she saw. She ran her hands across my smooth body, up and down my legs and my ass. She cupped my balls through the thong and asked how these were doing I told her that they hurt and ached, even to the touch. She said, "Oh no, that's not good. At least not for you, I happen to like you having that feeling."

Trista then told me to kneel down in front of her and opened her legs. She had nothing on under her robe and her pussy was once again in my face. "Now, you know you that you weren't fully cooperative today. You'll have to be punished for that, but if you do a good job on your knees I might take go a little easy on you. Now get to work."

With that she pulled me into her pussy and I did indeed go to work. She was so incredibly wet, which she told me, was from watching me walk in my new outfit. That stirred my cock even more and made me work all that much harder to try to get her off. After 10 minutes and 2 orgasms she stood up in front of me, her robe still open, her large breasts and shaven pussy still visible to me, which didn't help my aching balls at all. 

Trista walked across the room and came back with the paddle in her hand. She told me to bend over the table and to accept my punishment. I did as was told and she took a lot of time running her hands over my ass. She asked me, "Do you like being in this position? Knowing what's coming, so open and exposed and me being behind you like this?" When I admitted that I was turned on by it she cupped my balls and said that was what she wanted to hear. She had me lower my thong and she proceeded to give me 20 smacks with the paddle alternating from side to side. When she was done he told me to hold still that she wanted to get some lotion to rub on my ass as it appeared to be pretty red. 




Working with Trista Ch. 03



She grabbed some lotion from the nightstand and began to rub it against my battered backside. It felt soothing and she was doing it very sensually. Soon I felt her finger pressing against my asshole and I felt myself hold my breath. Trista told me to relax as her finger started to enter me. I had never experienced anything like this before; I gasped as I felt it enter me as. She moved her finger in and out of me a few times, and before I knew it, I was pushing back against her finger. Trista laughed when I did that and called me a whore. She withdrew her finger and told me to hold still that she had a little surprise for me. 

She opened the bag up that she had gotten at Bolt's store. Trista showed me one of her purchases, it was a plug. I started to protest at first, it wasn't very big but it was definitely something I wasn't used to. "Now now," Trista said, "it won't be any different than my finger, it's only slightly bigger and you will barely even know it is in there. It's actually probably smaller than your little dick if I recall correctly. Now just hold still and relax." 

With that I felt her press the small plug against my ass and once I reminded myself to relax the plug slid right in. She asked how that felt and I told her it wasn't too bad, it felt different but it didn't seem to be all that big. Still leaning over the table, Trista leaned forward, her breasts now resting on my back, and told me, "that's how it would feel if a little cock like yours was fucking you; it would feel ok but doesn't really fill you up does it. But don't worry; we will work up to something bigger for you. You looked like such a little whore with your ass sticking out and bending over the table, I bet you could take a real good sized cock up that ass of yours couldn't you." 

She was running her hands over my chest, as she whispered all this in my ear I was totally in the moment when I whispered back to her, "yes." I shuddered just a bit when I heard her answer which was, "yes you will."

With that she smacked my ass and stood up, told me to get dressed that we had a dinner to get to. I had had such a busy day that I didn't even realize it was almost seven by this point. I asked her where we were going to go to eat and she told me that we had a company function to get to. She reminded me that while it may not seem like it to me, that we were here for work. She then told me that since it was a work function, I didn't have to wear the heels, but everything else I should keep on. When I started to protest, she said, "Any protesting and we can switch back to heels if you want?" After that I was didn't argue. 

About a half hour later, we were dressed to go. Trista wore a slinky black dress and heels, and I was looking presentable in suit and tie. Of course underneath that suit and tie were thigh highs, a bra and thong, not to mention a plug still in my ass. 

At the dinner, Trista took me around and introduced all of the sales people. I had heard some of their names before and talked to a few on the phone but this was the first time I met with most of them, as almost all were on the road all the time and rarely in the office. It was nice to finally meet a lot of them in person; however, I was on edge the entire time. I didn't dare take off my jacket for fear that someone would notice the bra I had on underneath. 

After dinner, there was a social hour with open bar. I didn't know anyone so I stayed at the bar, nursing my drink as I kept an eye on the ball game that was going on behind the bar. On occasion I would watch Trista work the room, she just exuded sexiness as she went from person to person. 

As I was admiring Trista, one of the salesmen I met earlier noticed me watching her and approached me. "A real piece of work isn't she," he said to me. I pretended to not know what he was talking about but he said, "Hey man, don't worry about it. She's a real fine piece of ass. I saw you admiring her, and I don't blame you. My name is Bill by the way, in case you forgot." 

I talked to Bill for a while, most of our conversation consisted of him talking about Trista's body. At one point he told me, "She must give you a real case of blue balls, she must be such a cock tease to work with." I told him that he had no idea. He proceeded to tell me about a friend of his that used to work for the company that dated Trista briefly. He told me that he heard she had "peculiar tastes," and to be careful. I just laughed and said I would keep it in mind. In my head I wondered where this good advice was a few days ago.

As I talked with Bill, Trista made her way over. Bill used his charm immediately asking Trista how she managed to slip into a dress that tight. I have to admit, she deflected his advances expertly as Bill put on a clinic of what would be terrible lines out of sexual harassment videos. 

Eventually Bill left us alone but not before making a few more unsuccessful advances. Trista told me that a bunch of the guys were going to go out, most likely to a strip club and that I could go if I wanted to. I asked her what she wanted. She just smiled at me and said, "I think it would be best if we went back to the hotel room."

At the door to our hotel room, Trista told me to wait in the hallway. She went into the room and came back out a couple of minutes later holding the high heels and wig that I had worn earlier. Trista explained to me that she only wanted me in proper attire in the room going forward. Fortunately for me she said, I had the proper attire on underneath my clothing. I asked her to clarify, and she told me she wanted me to strip down to the bra, thong and stockings in the hallway and put the heels on before entering the room. I looked up and down the hallway, and asked her if I had to do it right in front of our door. She said yes and was clear that when I knocked on the door to get in, I was to have folded my suit on the floor and be wearing nothing but the lingerie and heels. With that I saw the door close in my face. 

I stood there stunned for a moment, before quickly stripping down, folding my clothes and putting the wig and high heels on. I then knocked softly on the door. When it wasn't answered right away I knocked a little harder. There was no one in the hall but I knew that could change at any moment. I knocked again, and called Trista's name, pleading with her to let me in. A few moments later, Trista finally opened the door a little bit and told me to turn around. She wanted to see my ass in the thong. 

I quickly turned around, showing her my ass. She then told me to bend forward, sticking my ass out. Even though I was still in the middle of the hallway, I was anxious to do anything to be let back in the room. As I bent over, Trista stepped out into the hall and ran her hands over my ass. "Mmmmmm, this feels so nice," she said. Her hand ran between my legs and I felt her hand cup my aching balls. "Oh these feel so nice and full," she told me as she squeezed them slightly. 

She gave my balls one final long squeeze and said to me, "Ok girlie, come on in, we're going to put your tongue to good use again."

I followed Trista into the room. She directed me to the large patio doors that opened up to the balcony that overlooked the strip. She told me to stand up against the doors. I did as told and soon I felt her hand on my back and she pressed me firmly against the doors. My body could feel how cold the doors were in comparison to my skin. 

"First, we're going to redden that ass, this time with the paddle," Trista told me. She proceeded to paddle each side of my ass 15 times. With each swing, I could feel my ass heat up. With my face pressed up against the patio doors, I was able to look out and see people across the street. I knew with these windows there was no way they could see me but it still felt as if I was on display. 

When Trista was done with the paddle, she asked me about the plug in my ass. I told her that at first it had felt weird but now I was growing accustomed to it and it hadn't bothered me for most of the evening. She told me that was what she wanted to hear and that it was time to up the size. 

I started to stammer that that wasn't necessary but she wanted none of it. She went to her goodie bag of toys she had bought and removed a larger size plug. She told me this was a medium sized plug and I should be able to take it pretty easily. I resigned myself to my fate, and just nodded my head. Trista then slid open the sliding glass door to the balcony and told me to step outside. I hesitated naturally and she told me, "Listen, either you're going to go out on this balcony and do as you're told out there or a few things are going to happen. First, that chastity cage is going to have to be cut off by a locksmith and second, everyone that you know will see the various pictures of you that I have. Remember you lost the bet."

That threat didn't leave me much choice. In high heels, a wig, stockings, a thong and bra I slowly made my way out to the balcony. The night air was cool, but it was comfortable. Trista followed behind me, the plug and a bottle of lube in her hands. I actually hadn't walked out onto the balcony since we had changed rooms. There was a lot of room out there, though it wasn't totally private, we could see the rooms across the strip. Trista noticed me looking around and across the street. "Yup, if anyone is looking out their windows, they are going to see you take this plug up your ass my little whore. Just imagine you're putting on a show."

Trista told me to bend over one of the chairs that were on the balcony with my back towards the hotel across the strip. My ass was still plenty sore from the paddling I received only minutes ago and so when she slapped my ass with her bare hand I let out a yelp. She then lowered my thong, and removed the small plug I had in me. 

"Grab your ass and open it up for me, and then ask me to put this bigger plug into you. "You know you want it, beg me for it" Trista whispered into my ear. I wasn't sure that I actually wanted it but I knew that it was going to go in either way. I asked her, "Please put the bigger plug into my ass."

Trista laughed, "Oh I'll put it in there, have no doubt about that, but I want you hear you beg for it. Hell, why not scream for it, let everyone know how badly you want your ass filled."

"Please put the plug in my ass, fill me up," I said much louder. 

"Louder bitch," Trista said to me. "Let me know what a whore you are."

"PLEASE PUSH THE PLUG DEEP INTO MY ASS!" I yelled, loud enough it seemed for all of Vegas to hear me. 

"Ah much better," Trista giggled, "you are going to have your wish." 

She lubed the plug and slowly pushed it into my ass, it was much bigger than the other one and did not go in as easy. She made me keep holding my ass as she pressed it inside of me, all the while whispering in my ear how much she liked seeing it go in there and how much of a slut I appeared to be. 

Finally the plug slipped into place, and I felt VERY full. Trista complimented me on taking it like a good little girl and she told me to stand back up so she could sit down in the chair. When I stood up my legs were a little wobbly, as I tried to get my balance on my heels. 

Trista then stood in front of me, and she let her robe open wide. She smiled at me and told me, "Now it's time for you to thank me for filling your ass. On your knees bitch."

I knelt down in front of her as she sat in the chair and spread her legs. She pulled my head into her pussy and she was almost suffocating me as she ground her pussy into my face. As I licked her she kept talking about all the things that she had done to me. Using the crop and paddle on my ass, dressing me up, making me suck the dildo, have me in a speedo at the pool, in nothing but spandex in the gym, being paddled in the store by both Jake and Alana. Gradually building up with each thing she mentioned, she finally climaxed all over my tongue which I happily licked up. 

Her orgasm was so powerful I almost felt certain that she wouldn't deny me an orgasm of my own tonight. I looked up at her hopefully, and Trista must have sensed what I was hoping for. (Though let's face it, she knew exactly what I was hoping for and would know for as long as she held that key.)

She then asked me if I wanted to cum, and I told her more than anything. Trista told me to be careful of what I wished for, and I told her again that I wanted to cum more than she could imagine. 

She said that she would make a deal with me. If she could use the crop on me 10 times and I wouldn't make a sound, she would allow me out of the cage to cum. Now my ass was still quite sore from the paddle but I felt that I could make it. I had always had a high pain tolerance and I thought that my chances were pretty good all in all. 

Trista told me to go back into the hotel room and grab the crop and bring it out to her. I did as told as quickly as I could in heels and with swollen balls. She told me to turn around and peer over the balcony with my ass towards her. 10 swings she reminded me, without a sound. Just to be safe I only nodded my acknowledgment. 

The first swing through the air landed squarely on my ass and I gasped, but I did not make a sound. The same with the second and third swings. They hurt like hell and I was biting my lip but I had not made a sound. The fourth swing was in the same spot as the first and it caused me to jump a bit as she was now swinging as hard as she could but yet again I hadn't made a sound. 

The fifth swing was hardest of them yet and was in the same spot as the first and the fourth. The sixth quickly followed and I was not ready for but again I hadn't made a sound. 

"Impressive," Trista said, "I thought you would have made a sound by now for sure. And actually you're going to wish you had. Spread your legs wide. These next four are going to go on your exposed, swollen full balls and it is going to hurt. I will offer you a reprieve though. You are going to get four swats with this crop on your balls either way. However, whenever you make a sound, the remaining ones will be lighter, they'll still hurt I'm sure in your condition but they will hurt far less." 

My mind was racing, I hadn't prepared for this. Hell, I didn't even know it was an option! She reached between my legs and actually grabbed my balls in her hands and gave them a little squeeze, "This is going to hurt you much more than it could possibly hurt me." 

She let go and the crop landed squarely on my balls and I nearly went down to my knees in pain. I was trying to catch my breath when the next one hit my swollen sore balls. Try as I might, the yelp simply escaped my lips and Trista said, "Oh dear, you made a sound." The next two with the crop were as soft as could be but the damage was done. 

Yet another night in the cage with no relief and now my balls weren't only sore from being full and not being able to cum but from literal pain as well. 

Trista giggled as I slowly made my way back inside on the heels and my wobbly legs. "Don't worry my little slut, we can try again tomorrow, maybe in a different manner though. I have a ton of good ideas, don't you worry. Why don't you sleep in that outfit tonight, it looks so good on you."

I slipped off the wig and heels and climbed into bed, still with the stockings, thong and bra still on, and my ass still filled. A lot went through my mind that night, as I started to fall asleep. I had been through a lot thus far on this trip. 

For the first time ever, things were going into my ass, I was dressing in women's lingerie and high heels. I hadn't cum in days and my balls were never this full. My ass and balls both hurt, and it didn't seem like this situation was going to change anytime soon. I had 2 more days before our trip was over and I wasn't sure if I was going to be able to make it. The more I thought about it, the more my cock strained against its cage and the more my cock leaked pre-cum. I was confused with why I kept getting turned on by the things that I was being forced to do, yet at the same time, I couldn't help it. 

I'm not sure exactly when I fell asleep but I knew that I drifted off to sleep wondering what the future might hold for the next two days as my cock continually tried to get hard at the thought. 

To be continued...........



Working with Trista Ch. 04



This is the continued story of working with Trista. If you haven't read the prior chapters please do so, to see how exactly the story got to this point. As always, feedback is appreciated, and comments welcome. Thanks for reading. 

Day 5

I woke up in much the same state that I had fallen asleep. My balls were full and aching and my cock was once again unable to attain an erection. My balls and ass were not nearly as sore as they had been the night before though due to the crop that Trista had used. 

I looked around the room and didn't see or hear any sign of Trista. At first, I was relieved, but then I started to panic. If I lose track of her I would really be in a tough spot with her still having the key. I sprang up out of bed and walked towards the kitchenette. There on the counter was a handwritten note.

..................................................

Good morning slut, 

I had to run out to do a few errands, after all, remember we are here for a work-related reason. I should be back in a few hours. In the meantime, I left what you should wear in the bathroom. Be sure to put on each item after your shower. I'll be back to lay at the pool this afternoon if it's nice. 

Xoxo, 

Trista

..................................................

Naturally I was both interested and a little worried to see what she had laid out for me. My cock began to strain as I imagined the possibilities. I walked across the room to the bathroom and saw sitting on the sink what she had left for me. 

Folded neatly on the sink were a red bra and thong. On top of those items was a bottle of red nail polish, similar to the color that I had suggested she paint her nails earlier in our trip. Finally, in the middle of everything was a bottle of lube, and another plug. This one even bigger than the one I had in me currently. There also was another note. 

..................................................

Hi again slut, 

I hope you like the outfit I have put out for you. Use the facilities as necessary and then shower and shave. Insert the plug up your ass, I would love to do that myself, but I want that ass filled as soon as possible. After you are filled up, paint your toe nails and your finger nails. When they are dry put on the attire I have left out for you. When you're done, go downstairs and eat some lunch, it's going to be a long day. In the top drawer of the dresser I put out what you should wear while you eat. 

Xoxo, 

Trista

..................................................

Well needless to say, my cock was leaking non-stop with pre-cum and was straining to get hard. 

I followed the instructions that Trista had left me. When I removed my plug, it was certainly an odd sensation. Nothing like removing the smaller one the day before, this one was much different and I felt my ass stretching as I removed it. I looked over at the large one sitting on the bathroom counter and I couldn't imagine how that was going to feel. I knew however that I best have it in me by the time Trista returned. 

After I got out of the shower, I stared at the plug sitting in front of me on the counter. I felt very over-whelmed but my caged cock was also straining at the thought of the plug being inside of me. It didn't go in all that easy, I had to continually remind myself to just relax and not tense up, but eventually the plug slipped inside of me. 

When it finally slipped into place, I found out that I had been holding my breath, gritting my teeth and was tense all over. I let out a deep breath and felt myself relax. With each movement I made though I could feel the plug inside of me. I had a feeling this would be a constant reminder as I couldn't imagine ever becoming used to this feeling. 

I then started to paint my nails, both my toes and then my hands. The red was certainly eye catching. I wondered if it would be as noticeable to others as it was to me. But then I thought that whenever a woman had on this shade of red I always noticed without fail. 

When my nails were dry I walked over to the dresser that Trista's note had directed me to. I was relieved when I opened the drawer and on top was a white tee shirt and a pair of shorts. 

..................................................

Hiya, 

Yes, I want you to wear the red bra, underneath your white tee shirt. Yes, I know that others will see you. And yes, I know that right now your tiny little cock is straining against that cage just thinking about all of this. Call me when you've sat down, I'll head back then as I want to see you with your new bra on. I can't wait!

Xoxoxo

Trista

..................................................

She was right; my cock was straining to get hard but to no avail in this cage. I got dressed and as I walked down the hall to the elevator, my balls were already aching. I knew it was going to be a long day when it was still not even noon yet and my balls were already hurting this much. Normally they do not ache as much in the morning, but when I get as riled up as this as soon as I get up, they immediately start hurting again. And that was exactly the way Trista wanted them. 

I sat down and ordered my lunch from the waitress who gave me a funny look. At that time, I also called Trista as she had asked. 

Trista: Hey little whore, glad you called. I'm just on my way back.

Me: I just ordered.

Trista: Oh yeah? Are some people looking at you funny?

Me: Yeah the waitress gave me a few weird looks. 

Trista: Why was that?

Me: Because of the outfit you had me wear.

Trista: Oh the bra? 

Me: That and the bright nail polish. 

Trista: (Laughing) Hey, you picked out that color.

Me: For you not for me. 

Trista: How's your little dick doing?

Me: It's frustrated. 

Trista: Oh, poor you. How's the plug doing? 

Me: It is quite a feeling; it's much bigger than the last one. 

Trista: It's the next size up. Plus a slut like you I'm sure likes having something up your ass. Ok, I have to go; I'll be there before you're done eating. I'll call you when I'm coming in. 

I was just finishing lunch when Trista came in and sat down. She was laughing as she looked across the table at me. I asked her what was so funny. "You can REALLY see that bra through that tee shirt. I saw it as soon as I walked in." 

When she saw I wasn't laughing about it as much, she said, "I would apologize as I didn't think it would show that much, however, I'm not really sorry to be honest. Plus I think you need to get used to wearing one anyway."

I must have given her a puzzled look and she said, "Oh sweetie, a bra is going to be a full-time thing for you the rest of this trip. We only have a few more days here and we have to make the most of it. I did think however, that we deserved a little pampering. I booked couples massage this afternoon. The weather doesn't look that great anyway; I thought we might enjoy this." 

We then went upstairs, I simply watched television and Trista showered and got ready for our massage. I had assumed it was in our hotel at one of the spas but she explained to me she got a better deal at some other place we had to drive to and soon we were off. 

On the way over, Trista had asked me if I was nervous. I actually wasn't, and told her so. She simply smiled at my response and the rest of the 10 minute car ride had left my mind wandering. My legs, chest, everything else was hairless that was true, but I have to imagine that the people giving the massage had seen all that before. My nails were painted but I could just remain on my back and they wouldn't notice. Yes I had a bra and thong on underneath my clothing but I was pretty sure they let you undress privately. I had a large plug in that I was reminded of every single time I sat down but I couldn't think of a scenario where that would be an issue. Finally, my cock was still in its cage. While maddening, I couldn't envision how that would be an issue either. I decided I would just try to enjoy myself, after all, this trip was nowhere close to what I had been expecting and I could use a relaxing massage. 

We arrived, and it was just one of those massage places in a strip mall. It was off the strip and it didn't quite seem like the stereotypical massage place you see on the movies, you know the ones where they ask you in some foreign language if you want a "happy ending." This seemed like a respectable establishment. 

I followed Trista inside and she talked with the receptionist, a cute young girl named Mandy. I tried to hide behind Trista as I didn't need the gal seeing the bra through my shirt. I was shocked when I heard someone say, "Trista! So good to see you."

I turned to where that voice was coming from, and I then knew this wouldn't be the massage I had been hoping for. It was Alana, the woman who had "helped" Trista try some things out in Bolt's store on our third day in Vegas. 

They exchanged pleasantries and Alana told us that we would be in room 4, straight down the hall. She told us to go in, relax, put a sheet on and lay down on the tables; she would be in, in a few minutes. We walked down the hall, and I thought to myself that maybe this massage wouldn't be too bad. I was as nervous as could be as Trista and I disrobed. She kept smiling at me and that made me more nervous than anything else. 

I watched as Trista disrobed. She was quite a site. Her large full breasts were incredibly intoxicating and her legs were incredibly sexy. As I watched her strip off one piece of clothing after another, my cage continued to prevent my cock from getting hard. Trista eventually noticed me staring at her and she crossed the room and took my swollen balls in her hand and gave me a squeeze, "It's not nice to stare," she said. 

I gasped as she squeezed my balls. "My these feel full, do they hurt?" Trista asked. I could only nod as her grip held firm. Finally she released them, and I struggled to catch my breath. 

Trista slid onto the massage table and covered herself up with her sheet. I followed suit, of course laying on my stomach was an issue with the cage. Trista just looked at me and smiled. 

Soon after, there was a knock on the door and Alana came into the room. She spoke directly to Trista and ignored me. She said that she would get started and that Jake was finishing up with some other customer and would be in soon. (Being the bright mind that I am I assumed that Jake was her husband who I had also met at Bolt's store.) Alana told Trista that they could start with the massage without Jake and that I would just have to be patient. 

As if I wasn't riled up enough and wanting to cum already, watching one hot girl give a massage to another one wasn't helping matters at all. I watched as Alana moved her hands up and down Trista's legs. This was for about 10 minutes before another knock came on the door and Jake stuck his head in. My earlier suspicions were correct and it was Alana's husband. He said he would be about 10 more minutes. He smiled at Trista and looked quickly at me but his look was dismissive. 

For the next 10 minutes, I watched as Alana massaged Trista's back, the sheet exposing more and more flesh, all the while my cock straining to get hard but to no avail.

Jake came back into the room and had said that he sent Mandy home. I must have looked nervous as Alana said, "you guys are our last appointments of the day." Jake apologized for running a little late and he switched spots with Alana and continued Trista's massage as Alana began my massage. 

It felt really good, she commented a few times how stressed I felt, jokingly adding that I must be spending too much time in certain specialty stores. 

I heard Jake instruct Trista to flip over onto her back and Alana suggested that I do the same. Shortly after, Trista said to Alana, "be sure to give him the full treatment, just like we talked about." With a couple of minutes, Alana's hands were very high on my thighs and my cock was straining to get hard once again as I felt her hands go up my thigh. Before I knew it, this great feeling was gone as I felt her hands wrap around my swollen and full balls. I felt her squeeze and I let out a whimper.

I heard Trista laugh as Alana continued squeezing my balls. Trista then said, "Keep up his massage as long as you want, but whenever you're ready, his tongue is magnificent." I looked over at Trista and saw that her sheet was up around her waist and at that point Jake seemed to be fingering her, playing with her pussy. 

Alana kept up my "massage" for the next couple of minutes, finally she let up her pressure and she said told me to lay still. Within moments, she was on top of the table, straddling my face. Her pubic hair had been shaven into just a bare strip. She brought her pussy in front of my face and then leaned in and told me, "Now lick me slut."

I was happy to do so, for one thing my balls were no longer being tormented, but Alana was a beautiful woman and I was happy to let my tongue dive into her wet pussy. I was busying myself in my work with Alana and I could hear Trista moaning. I couldn't tell from what exactly, but I had my suspicions. Either it was from Jake's tongue or he was fucking her. Doing what I had initially hoped to do on my trip out here. 

It was 10 minutes later and Alana had cum a couple of times as she kept grinding her pussy into my face. I hadn't heard Trista moaning for a couple minutes but I could tell that she had also cum a couple of times as well. Alana slid back onto my chest, she remained sitting there but she continued to play with her pussy in front of my face. I turned my face to the side and I saw Trista standing there naked, and in her hand was Jake's cock. 

"Do you see this cock?" she asked me. "This is a real cock. This is one that can please me. Not that little thing you have. If you have been wondering why your little dick is locked up, it's because your cock could never please me." 

I stared at the cock in her hands, and I have to admit, I wasn't much of a comparison to Jake. His cock didn't seem fully hard and it still appeared to be about 8 inches long and very thick. Trista continued to slowly stroke his cock near my face as Alana continued to play with herself in front of me. 

"Jake's cock is bigger than that dildo you had in your mouth a couple of days ago, you little whore. I bet you wish you had had Jake's cock in your mouth don't you," Trista continued. "Your little cock deserves to be locked up and not near our pussies." 

As Trista continued to stroke Jake's cock, Alana reached back and started to play with my balls again, cupping and squeezing them. My cock was straining against the cage and this was by far the closest I had ever been to another man's cock in my life. My head was spinning. I didn't know if Trista was going to push Jake's cock into my mouth and make me suck him or what was going to happen but I couldn't take my eyes off of Trista stroking that large cock next to me. 

Finally I heard Alana say, "Make him cum on me." Trista replied what a good idea it was and before long Jake's cock was spurting out his cum onto Alana's chest, stomach and dripping down to her pussy and my chest. 

I watched as his cum dripped down Alana's body, it was hot no doubt about it, but at the same time, I didn't think I could have felt more submissive. Here I was, watching this large cock cum inches from my face onto his hot wife who I had been made to pleasure with only my tongue and my cock was locked up and hadn't been allowed to cum all week. The fact that there was constant reference to his much larger size than mine also didn't help at all either. 

Remember though I said I didn't think I could feel more submissive. I was wrong. 

Trista let go of Jake's cock and ran her fingers through the cum that was accumulating on my chest as it ran down Alana's body. She took two fingers and rubbed through the cum off of Alana's chest, coating her fingers in Jake's cum. 

"Open up," I don't know why I didn't put up a fight, but I didn't as I opened my mouth as soon as she told me. She put her fingers onto my tongue and then ran them along my lips. I could taste the cum and Trista said, "I knew he was a natural cum-eater."

After that, everyone got up and was getting dressed. I just hung my head in shame and didn't even try to look anyone in the eyes. Trista thanked them for the massage, and I was told to thank Alana for allowing me to eat her pussy and to thank Jake for letting me have a taste of his cum. 

On the way back to the hotel, I was pretty quiet. I admit that while I had done a lot of things this past week that I hadn't planned on experiencing, I can honestly say that tasting another man's cum, no matter how small an amount was definitely not on that list. I hadn't said anything when Trista asked if I was all right. When I mumbled that I was fine, she asked if tasting the cum was all that bad. I had to admit that it wasn't, there really wasn't much to the cum, it was more of a mental thing. It was the feeling of submission.

She giggled and said, "Well you have tonight and tomorrow yet, and trust me, you're going to be feeling a lot of submission." For some reason, I felt nervous, fearful and worried from that statement, all the while my cock was once again straining hard against the cage as I thought about the possibilities. We arrived back at the hotel and Trista told me to go shower and get all of the massage oil (and Alana) off of me. I was showering and once again I looked down at my caged cock. Jake had been noticeably bigger than I was. He wasn't a monster by any means, not like you see on some websites, but his cock was something I definitely couldn't measure up to. Trista's words kept ringing in my head saying that Jake had a real cock that could please her. Oh how this trip had not turned out as planned. 

When my shower was finished, Trista took a shower as well. Most likely to wash Jake off of her. When she was finished, she told me we were going out to dinner. Once again, she put me into a bra and thong, complete with thigh high stockings. A pair of pants and a shirt went over but I was still self-conscious about going out with these on again. Especially after what happened earlier today. 

Our dinner was surprisingly uneventful. It was similar to our first night. Drinks were flowing and I admit I may have had a bit too much. However, I felt that if anyone had earned the right to have one drink too many, it was me after my day. Trista didn't scold me for it either; she kept making sure my glass was full. 

We arrived back to our hotel, a few hours and many drinks later. Trista told me that she wanted me to remove my clothing except for the lingerie underneath and to add the wig and heels. I did as I was told, though I must admit that while I had been a little wobbly on the heels before, the drinks I had were doing me no favors. I stumbled up and out to the kitchenette where Trista was waiting. 

"My don't you make a sexy little slut. You wouldn't mind if I took advantage of you would you?" she asked coyly. 

While the other tasks earlier in the day I may not have been a totally willing participant to, at this point with the drinks I had, I was fully up for any sort of fun. I proceeded to tell her as much. She smiled when she heard that. 

Trista told me to wait patiently and she would return in a minute. I watched her walk sexily into the bathroom after grabbing another one of those bags she had purchase from Bolt's store. About 5 minutes later she walked out, in black stiletto high heels that were similar to mine though hers seemed more "powerful." 

Her legs were covered in nylons, and she had on a black silk robe. She smiled as she walked over to me, and she told me, "Get on your knees whore." 

I knelt down immediately following her commands. Trista then opened up her robe and in front of me was a black dildo sticking out in front of her. "Now suck my strap-on you little slut" she told me. 




Working with Trista Ch. 04



She grabbed me by the back of the head and pushed the rubber dildo into my mouth. I had my eyes opened; she had on thigh high stockings a black teddy and the black strap-on. As I sucked on her cock Trista kept berating me, "That's right bitch, suck my cock. You little cock sucking whore." 

My own cock throbbed against the cage it was in. Trista continued holding the back of my head, forcing the entire thing into my mouth as I slightly gagged on it. 

"This pathetic thing is roughly the size of your own little cock; you should have no trouble deep-throating it."

When Trista had watched me suck her cock long enough she ordered me to the bed. "On your hands and knees slut, you know what's coming next. " 

Trista came up behind me, and removed the plug from my ass. "Ask me to fuck your ass now."

I hesitated slightly and she slapped my ass as hard as she could. It stung immediately and she once again told me, "Ask me to fuck your ass you fucking whore." 

I whispered the words she wanted to hear. She slapped my ass hard once again, "ask me so I can hear you bitch. You know you want my cock up your ass, ask me for it. Ask me to fuck you hard."

"Please fuck my ass Trista, please fuck my ass hard," I moaned. 

"Oh I plan to. I'm going to fuck that ass very hard," she told me. She lubed up her cock and I felt it up behind me. She told me to relax and I tried as best I could. With a few moments, the tip of her cock was inside my ass and she continued to push. She started to slide the phallus in and out and before long she had buried it all the way inside of me.

When she felt that I had adjusted, she told me, "Now the fun begins."

With that, she slowly slid the cock out of me until only the tip was in. Trista then grabbed my hips and forcefully she thrusted the fake cock into me. I let out a moan and she repeated her thrust. Once again I moaned. 

"Oh let me hear you moan bitch," Trista moaned, "let me hear you as I fuck your ass." 

With each thrust, I moaned out not because of following commands but because I could not help it. It hurt and felt good all at the same time. I was now sweating as Trista continued pumping her dildo in and out of my ass. My cock was dripping of pre-cum, my balls throbbing from being filled with cum all week and I was breathing heavily. 

Trista started slapping my ass with each thrust. "Oh I love this, I was going to wait until tomorrow to do this, but I'm glad I chose tonight. Tomorrow is now going to be even better."

I wanted to ask what she had all planned but I was so out of breath I couldn't form the words. Trista continued to slam the dildo in and out of my ass for another 10 minutes. By the end, we were both exhausted. 

When she slipped out of me, I simply collapsed on the bed. My ass was on fire from all her slapping and I was covered with sweat, not to mention the fact that my ass was sore from the 20 minutes she had spent plunging a dildo into me roughly. 

The last thing I heard as I was falling asleep from a combination of the exhaustion and alcohol was "Rest up, we're doing so much more tomorrow." 

To be continued...



Working with Trista Ch. 05



This is the final two days of my trip working with Trista.  If you haven't read the other portions of this story, I would suggest it.  
Feedback is welcome, especially of the message variety as I would love to discuss these adventures.  Otherwise if leaving public comments, please make them constructive.  
Thanks.

-------------------------------------------------


Day 6

When Trista woke me up the next morning it took me a while to get my bearings.  I had a slight headache and was sore all over.   After getting my bearings, I realized that it was an alcohol type of stiffness I felt throughout my body.  I had crashed hard.  As I stretched out, I was reminded of what exactly happened the night before.   My cock immediately pressed against the cage it was in as I thought of Trista thrusting the dildo in and out my ass the evening before.   

My concentration was broken when Trista said to me, "Get in the shower, we have to get going."  It was 8 am but it felt so much earlier.  

In the shower, I thought back to everything that had happened to me on this trip.  Having all my hair removed professionally, wearing only a thong at the pool, being allowed to wear only spandex when working out, wearing lingerie almost exclusively the past couple of days, being spanked repeatedly, being forced to try on and purchase high stiletto heels, watching as Trista had sex with Jake, tasting a drop of cum, taking a dildo up my ass, and maybe most importantly of all, having my cock locked in a cage to which only Trista had a key.  She had warned me that a lot more was to come today, though I didn't think I could imagine it.  So much had happened already that I didn't ask for nor was prepared for.  I had made a little bet and it seemed to just spiral out of control.  

The worst part of it all was that I was turned on more and more by everything that Trista did to me.  Every time she spanked me, my cock tried to get hard.  When sucking on her dildo, my cock leaked pre-cum.  When she dressed me as a woman and treated me like a slut, my balls ached.   I had to laugh as I remembered it was only 6 days ago that I thought I was going to get to fuck her and it was what I had been most looking forward to.  That hadn't happened, and instead it was I who was taking it up the ass from her strap-on dildo.   If someone had told me of the predicament I would be in now I would not have believed it. 

Once again, Trista snapped me out of my trance as she knocked on the door and told me to pick up the pace.    I got out of the shower and dried off.  I walked out of the bathroom in just a towel and Trista told me she had put out clothes for me to wear. 

I looked at the bed and there was a pair of black spandex tights and a matching black spandex long sleeved shirt.   I asked her if we were going down to the gym in the hotel. She said no but that I would get a workout.  She explained to me that being that yesterday was the last day of the convention; we had some cleanup work to do. 

I already knew the answer but I asked Trista if I could wear something over this outfit instead of just spandex.  She laughed and said, "Nonsense, our first day here, we were there in nothing but spandex, there's no reason why we shouldn't end the trip the way we started it.  Don't worry; I'll be in similar attire so that you do not feel on display."

On the walk through the hotel I once again felt that all eyes were on me though as strange as this sounds I felt like I was getting used to it.  I thought to myself that maybe this cleanup thing wouldn't be too bad.   Trista had worn a pair of black spandex tights herself and an over-sized gray sweatshirt. 

Once we arrived, Trista asked me if I was ready.   I felt that I was as ready as I would be and told her as much.   She just smiled and said, "I've decided that since you were so good last night that I am going to let you out of the cage for the cleanup."  

At first, I was so excited to hear the news but then I realized what she was doing.  With my cock out of the cage, I would immediately get hard; if not from being turned on and unable to cum for the past 6 days, but I would be hard from seeing Trista in her skin-tight pants.  Also it seemed that my cock always would try to get hard whenever I was on display, as if the humiliation turned me on.  

I knew better than to protest being let out of the cage, but at the same time this was the worst possible scenario of freedom.   

As soon as Trista produced the key and unlocked the cage that had been stifling any sort of erection my cock immediately proceeded to become hard.   Trista took it in her hand and began to stroke me.  "Awwww look that little cock is all hard now.  It's bigger but it still could never satisfy me.  But I bet you do want to cum don't you.  Those balls look so full; I bet you'd cum harder than you ever had before.   Are you excited to cum?" she asked as she continued to fondle my cock. 

I told her that I was excited to cum and I begged her to let me do so.    She just giggled and said, "But if I let you cum now, then others won't see your cock hard.  And let's be honest, its better they see it hard, otherwise they might laugh at how small it is.  At least when it's hard it's somewhat respectable."

She took her finger and ran it over my cock head, getting it wet with the pre-cum that had formed.  She brought it to my mouth and told me to open up.  I did and she put the pre-cum on my tongue.  "I bet you love that taste, don't you?"

I didn't even get a chance to respond before she pulled my waistband back up over my hard cock and patted it through my tights, telling me it was time to head in.  When we opened the door, I was not ready for what I saw.  When we had set up and I was in only spandex, there were others around but no one was close to us.  What I saw when we walked in was tons of people.  It seemed like a mix of people there, some to do what we were doing and others more the blue-collar type, taking down exhibit booths and displays.  It was safe to say though that I was the only guy there in skin-tight clothing. 

The next three hours were a workout.  We were busy boxing up items all the while I was on display with a hard cock.  Trista was not a help at all, for about a half hour in, she removed her sweatshirt revealing a bright red zip up the front spandex top.  Not only that but the shirt was short enough to fully show off her ass and her top was zipped down enough to give a very healthy shot of her cleavage.   While this display of hers naturally had an effect on me, it also got the attention of just about everyone else there, especially the blue collar guys.  There was an endless parade past where we were working.  A few stopped to talk to Trista to see if she needed help, others to hit on her, a couple made a few comments about me.  
The worst was when one guy asked her if I was going to rob the place, apparently as a joke on my all black attire.  Trista called me over and introduced me to the guy.  She then directed me to apologize for my erection I had.

As I did so the guy laughed and said, "So long as it's not directed at me."   Trista then said that it always seemed to be directed to her but that, "it wasn't nearly enough to satisfy her."   The guy was a little stunned at her bluntness to say the least.  

Those three hours were embarrassing but my cock was erect the entire time.  Trista commented as much in the car on the way back to the hotel, occasionally reaching over to my lap and stroking my cock through the spandex tights.  

When we arrived back at our hotel room, Trista once again used the bucket of ice to soften my cock and place me back into the cage.  She then proceeded to have me kneel in front of her once she had removed her clothing and told me to use my tongue to bring her to orgasm.  

I knelt down in front of her once again, a place I had become familiar with on this trip.  I let my tongue dance around her soaking wet pussy, flicking it in and out of her.  She ran her fingers through my hair and pulled my face deeper into her.  A few short minutes later she was once again cumming all over my tongue.   "Lick it all up you little whore," Trista moaned as she clamped her legs around my head.  

When she had finished cumming and regained her breath Trista told me she was going down to the pool for a little while, that I was free to join her or I could just hang out in the room and watch tv or take a nap.  She did tell me that I was in for a big night so that resting up would definitely be a good idea.  

I watched as she changed into her bikini, a white number with a few sparkles on it, and I was so tempted to go down to the pool with her but I was exhausted and felt that it would be best to lay down for a nap for a while after Trista's warning that I was in for a long night. 

Trista went down to the pool and I went to lay in bed, my cock still straining occasionally against the cage as I thought back to all that had happened on the trip.  Before long I drifted off to sleep. 

I was awakened by Trista when she returned from the pool.  She hopped in the shower quickly and emerged totally naked.  I looked at her in her naked form and as usual my cock tried to get hard.  I wish my cock would know better; it didn't really hurt but was incredibly frustrating to be constantly reminded that I was unable to achieve an erection unless Trista allowed it. 

Trista came over to me and suggested that I get into the shower as we had a hot date tonight and had to get ready.   She told me to be sure to shave my face, even though I had done so that morning. 

When I emerged from the shower, Trista was dressed simply in a maroon bra and matching thong.  She looked spectacular as usual. She rubbed her hands across my face, and felt how smooth it was, she smiled, "very nice."

"Now come over to the table and sit down, we have to get you ready for going out tonight," Trista told me. 

Walking over to the table, I saw her makeup bag contents all spread out.  Immediately, I knew that this was for me.  I started to protest, but Trista cut me off, "One more night is all and this has been what you've been working towards right; now sit down."

The tone of her voice, told me that this was not up for debate.  Granted she had plenty on me at this point being that she had been taking photos of me in various compromising positions for the previous 5 days.  As she started to apply the makeup, I thought of how she didn't even bother to threaten me this time, instead she just raised her voice and she knew I would obey.  What did that say about me?

I sat down, wearing only my towel and of course the ever present cock cage and Trista immediately started to apply the makeup.  She started first with concealer, and then followed with foundation.  Next she went to work on my eyebrows running a pencil through them.   She explained exactly what she was doing to me and why she was doing it though I have to admit, her words were sort of lost on me.  I did feel like I was being pampered though.  

Next she went to work on my eyes.  Applying first eye shadow, then eye liner and finally mascara.  When she finished with my eyes, she applied blush and finally lipstick and lip gloss.   Honestly, the only thing I would have known how to apply myself without looking ridiculous would have been the lipstick. 

When she was done she held up a mirror and I was amazed at what I saw.  Looking back at me in the mirror was a look that I had never seen before.   I looked like a female.  Now if someone were to look close enough, they would see I was a male but from a quick look or even without having some suspicion, I thought I was pretty passable.   Trista had done a marvelous job.  She had used smoky eye-shadow and black eye liner and mascara.  She also had used ruby colored blush and lipstick.  All I could say as I stared at myself in the mirror was "wow."

Trista laughed and said, "Well I will take that as a compliment." 

I told her that she should; that I didn't think such a transformation was possible.   

Trista then told me to get dressed with the clothing she had left on the bed, and that we had to get going shortly.  I wanted to ask where exactly it was we were going, but I just kept staring at myself in the mirror. 

When I finally made my way over to the bed I found exactly what Trista had laid out for me.  It was a short, black dress, some fishnet stockings and red stiletto heels.   Trista came behind me and said, "How do you like your outfit?"

I told her it didn't look like much and she responded, "Well that sort is the point. See, you're sort of the slut in this relationship, you're sort of the one who will be on display, and you're going to be the one getting the attention tonight so yeah, it's a tad bit short. But first, we have to give you some cleavage."

She showed me the tape she had purchased for this reason and proceeded to give me cleavage by using the tape to push my chest up and together.   She also used a few pieces of tape to hold the cage down between my legs.   

"That may be a bit uncomfortable for you between your legs like that but we can't have you giving away your secret can we?" she laughed. 

I thought it looked a bit ridiculous as I looked in the mirror but when Trista helped me slip the dress on, it did look like I had a bit of cleavage and I had no sign of a bulge in the front.   Trista smiled at her handiwork.  "Now put on the stockings and the heels and you'll be all set."

Trista had changed into a dress similar to mine though, hers was noticeably longer and red.  She had put on nude stockings and her heels didn't have quite the same "fuck me" look that mine did.  All around she looked quite a bit classier than I; however while classy, she still looked quite sexy.  

As the last touch, Trista put the wig on me and we looked at each other in the full length mirror in the room. 

Trista asked me what I thought and I said, "I can't believe it."

She laughed and responded, "Yeah we clean up pretty good. You look a little like a whore but still good.  But we better get going, we have dinner reservations."

I started to protest that I couldn't go sit at a restaurant but Trista told me nonsense.  Just be sure to use a female voice when I speak or simply nod, don't look people right in the eye and no one will know for sure.  Some people might suspect but no one will know for sure.

We walked through the hotel, I was trembling with excitement but Trista kept walking and I was struggling to keep up to her.  I felt that everyone was looking at me, but yet at the same time I refused to make eye contact with people as Trista had advised me.

Soon enough we were out front and hopping in a cab.  As we got in, Trista told the cab driver where we wanted to go to as she laughed hysterically.  When I asked her what was so funny she said, "I'm pretty sure that everyone in front of the hotel saw all your business up your skirt you stupid slut.  You can't even keep your legs closed getting into a cab."

My face turned beet red.  We arrived at the restaurant and I concentrated on getting out of the cab in a half respectable manner.   Trista giggled at my concentration of simply leaving the cab. 

We walked into the restaurant and Trista talked to the hostess.  My knees were literally shaking as I assumed that every eye in the place was on me.   In a way it was true, everyone seemed to be checking out my outfit, but no one was really gasping that I was a guy who had been made to cross-dress. 

Trista came over and said that our table was ready.  I followed her as she followed the hostess through the restaurant.   This time all eyes were on my short skirt and high heels.   I wondered if they thought I was a hooker.  We had a table in the corner of the restaurant fortunately.  When we sat down I mentioned to Trista that this seemed like a table for 4 people not just two.   Trista smiled and said, "Of course it's for 4 people, we couldn't let your big coming out party be just between the two of us, I know you would've wanted some company."

I swallowed hard and while I knew that Trista had planned for a big night, I didn't imagine that we'd be dining in a public place like this with me fully dressed as a woman.  

Our waitress came by and took our drink orders.  Trista was nice enough to order a couple of shots for us on top of a drink.   She later said it would help calm my nerves.   She took the time to introduce us to the waitress.  Trista introduced me as her friend Amber.  The waitress's name was Renee, and she was pretty hot.  She smiled at me and said, "Nice to meet you Amber, I really like your shoes."   I blushed beyond belief; it felt my face was on fire. I couldn't quite get the nerve to say thank you so I just smiled instead. 

As soon as our drinks arrived, we downed our shot and I started to work immediately on my drink.  Within a few minutes, Jake and Alana arrived and Trista explained that they would be joining us for dinner.   The dinner went well, all things considered.   Trista kept making sure that my drink was filled and I did my part by continuing to try to empty it.  

When Renee brought our check, she once again thanked everyone and said what a pleasure it was to meet all of us.  Once again, I was a bit too embarrassed to say much of anything in response to her, but I will admit the attention she paid to me did make my still full balls ache even more. 

Trista said to me, "Look at this, Renee put her number on the check.  And a little note, "Call me if you need some help with Amber, if I'm correct, she requires much discipline. Would love to help xoxo."

I blushed again, and Trista said, "It's too bad we're leaving tomorrow otherwise Renee certainly would get a chance to help out.   Would you like that Amber?"

I had to admit that I would.

As we walked outside, Jake and Alana said that they would see me soon.  I must have had a puzzled look on my face as Jake slapped my ass and said, "The night is young yet."

Trista and I hopped back into a cab and I started to question her as to what Jake meant.  She told me that she had invited them over for a night cap.  I didn't really respond but she said, "I told you that this last night was going to be a big night."

Back at our hotel, we exited the cab and I heard someone yelling Trista's name.   I turned and it was our sales guy Bill stumbling towards us.  Trista said, "Just don't say anything, don't look at him and let me handle him." I just nodded.  I'll admit it, I was worried. 

Trista turned to Bill as he approached and said hello.   He was obviously pretty drunk and as a result pretty "hands-on" it seemed as he talked to Trista.  They spoke for a couple of minutes and Trista then said, "Bill, let me introduce you to my friend Amber." 

Bill looked at me and in a voice too loud said, "Oh I like her outfit, much shorter than yours Trista."  

Trista laughed and said to Bill, "Yeah well she's much sluttier than I am."  That got Bill's interest.  Trista then said, "Yeah, I bet she'd let you feel her ass if you wanted to."

"Really?" Bill asked wide-eyed.

"Oh yeah, lift up her skirt, she won't even object.  Run your hands over her ass, even give it a slap or two, but do it quick, we don't want to get arrested out here," Trista told him. 

Bill came over towards me and reached his hand under my skirt, I felt his cold hand on my ass.  He rubbed his hand all over it, squeezing it roughly and then gave it a few slaps for good measure.  Trista had an evil smile on her face as she watched Bill roughly fondle me.  I was as nervous as I could be but I could feel my cock trying to get hard again as Bill ran his hands all over my ass.  Finally she came over and told Bill that was enough and that we'd catch up with him later.  Bill being under the influence of alcohol didn't bother to ask where or when fortunately for me.  




Working with Trista Ch. 05



I was obviously mortified as Trista and I went into our hotel. Some sales guy that I was going to have to work with saw me dressed as a woman and not only felt my ass up gave it a couple of slaps as well.   In the elevator, I mentioned that to Trista and she told me, "Oh, pffttt, that's nothing.  He didn't recognize you and most likely won't remember it.  You will though, every time you talk to him now."  She had an evil grin on her face. 

Back in the room, Trista had me remove my skirt and blouse along with the tape she had put on me to make me appear more womanly.  "Don't worry, you'll be feeling plenty like a woman before this night is over," she warned me. 

I was in heels, thigh-high stockings, a thong, bra, wig and complete makeup.  Oh and of course the ever present cage that prevented my cock from ever getting hard.  There was a knock on the door and Trista went to let in our dinner friends.  (It was amazing how relieved I was to see Jake and Alana as opposed to Bill or anyone else.  Jake and Alana I figured I didn't have much to hide from at this point.)

Trista had me serve everyone drinks in my risqué attire.  Once everyone was comfortable, it was finally Alana who said, "Well let's get this show started shall we?"  While I had figured there was going to be more to my night than just serving drinks, I had been holding out hope that running into Bill would be enough.  

Trista stood up and said, "Ok well Alana, why don't you start, everything you'll need is in that bag on the floor, help yourself."  

Alana immediately went to the bag and brought out the black paddle that I had become quite familiar with over the past week.  Alana asked Jake how many he thought that she should give me, he settled quickly on 30 swats.  Alana forcefully bent me over the back of the couch, my even higher in the air than it normally would have been because of the heels.  30 swats later I was nearly in tears and my ass felt like it was on fire.

Trista shortly followed after, she gave me 5 swats on each side of my ass with the crop she had dug out of the bag.  I thought that the paddle had hurt, but with my ass already quite sore the localized sting of the crop was even worse.  

They then asked Jake if he wanted to take a turn.  He laughed and said that if he were to swing something that I'd be in tears in no time.  I couldn't agree more and was happy to hear him say that.  Alana then suggested, "Then just use your bare hand."  

Trista giggled, "That's a great idea; this little slut has already had one man's hands all over her ass tonight, why not another." 

They didn't want me to simply standing behind the couch though for the spanking I was going to get from Jake.  Instead as he was sitting on the couch, I had to straddle him, reverse cowgirl style and lean forward with my hands on the floor.  That way, my ass was right in front of him and he could strike it without moving.  Trista took this opportunity to take many more photos of me in this compromising position.  For his part Jake's blows didn't hurt as much physically as the ones from Alana and Trista, though emotionally they were much worse.  

They made me count out 20 spankings before Alana told me come over to her.  She had lifted up her skirt, her bare pussy on display.  "Come over here and get to work."    I got between her legs and quickly began to lick her pussy.  She was quite wet and she pulled my head closer to her to get my tongue even deeper.   "That's right you little bitch, lick my pussy," she moaned. "I'd never let your little cock inside me but I'm going to cum all over your tongue."

I soon felt Alana's legs clench around my head and soon enough she was cumming on my tongue.  My cock as usual was struggling to get hard and my balls were starting to ache once again from being so heavy with cum.  

I heard Trista ask Alana, "Do you want him again or should we move on?"  Alana responded, "Oh I want another one but make him work for it will you?"  I didn't know what that meant but unfortunately I soon found out. 

As I tried to bring Alana to a second orgasm, Trista was behind me.  I found that "making me work for it" meant Trista running the crop lightly along my ass and between my legs while I licked Alana.   Occasionally, Trista would bring the crop down on my ass, making me yelp into Alana's pussy.  Before Alana came again, Trista would also bring the crop up against my balls three times.  It wasn't as hard as it could have been because of the angle, but it did the trick.  My balls now ached with every movement I made. 

After Alana came again I was literally gasping for air; she had had her legs wrapped around me so tight.  As she allowed me to lift my head up, Trista was standing right next to me.  In front of her was a fake cock kept in place with her strap on harness.  This cock wasn't the one from the night before, however.   Instead this one was much bigger.  I had about 2 seconds to process all of this before she said, "Open up slut" and she forced the large rubber black cock into my mouth.  She then began to thrust the cock in and out of my mouth.  

As she was fucking my mouth Trista said, "I hope you'll notice that this particular dildo is a bit bigger than the one you had before.  The one before was about the size of your cock.  This one however, as you can tell is much bigger.  It's the size of a real man.  The way a real cock should be.  While you'll never know what it's like to have a real cock hang between your legs, you now know what it's like to have one this size in your mouth.  And you better do a good job because soon you're going to know what it's like to have a cock this size up your ass.  Pretty soon you'll know why you never had a chance to put your pathetic little dick in my pussy.  It would never fulfill me."

"He appears to be a natural," Jake chuckled.  While the commentary on my lack of any chance with Trista was demoralizing, my cock strained to get hard as they continued to humiliate and insult me. I couldn't understand why my body was betraying me once again, but I knew that without a doubt being treated like this was turning me on. 

Trista continued fucking my mouth for about 10 minutes.   Finally she said to Alana, "well you think he's ready?"

Alana laughed and responded, "No I don't think he's ready for this but I don't see him becoming ready anytime soon."  That got a giggle from Trista and a laugh from Jake. 

Trista told me to stand and to remove the thong I had on.  When my balls were exposed, Trista knelt down in front of them.  She squeezed them in her hands and asked how bad I wanted to cum.  The pressure she applied kept increasing until the point it was hard for me to stand.  I begged for her to let me cum.  

"'Wrong question, my little whore.  You can beg me to fuck your ass though, then at that point I may consider letting you cum."

"Oh please, please fuck my ass, please fuck me if you will allow me to cum," I begged Trista.  
Trista smiled, "Since you asked so nicely, I will.  Now turn around and bend over the side of the couch, offer your ass to me." 

Embarrassed beyond belief, but yet unbelievably turned on, I turned around and bent over the side of the couch.  My ass up in the air, presenting myself for her.   I felt her begin placing lube around my ass and I felt her slide a finger inside of me. 

"Now slut, if you're good, you may be allowed to cum.  The key word is 'may.'  Keep in mind that you asked for this and so I'm going to grant your request.  I'm going to fuck you up the ass.  I'm going to treat you like a real whore.  We're doing it here because no one would actually take you to the bed to fuck you.  Whores like you get fucked on couches, or tables or the hoods of cars.  I'm going to take your ass hard, and it is going to hurt.  I actually want it to hurt.  I want you to be walking awkwardly tomorrow in the airport; I want you to be sore.  I'm going to stick this long thick cock up your ass.  You're going to moan, you may even cry, but it's going to fill you up like you've never felt before.  You see, you thought you had a chance with me but I'm going to show you what a real cock feels like.    As a matter of fact, you may think of begging me to stop.  But the only thing I want you to beg for is for me to fuck you harder and deeper. Now ask me again to fuck your ass with my big cock because yours is so small and pathetic that you shouldn't be allowed to use it.  That instead of using your own cock, you should be fucked with one."

My balls were about to burst.  If I was ever going to break the steel cage that entrapped my cock it was going to be now as I couldn't possibly strain against it any more than I presently was.  

"Please Mistress, put your big cock in my ass and fuck me.  My own cock is small and worthless and I should only be fucked with cocks instead of being able to use my own," I cried. 
With that, I felt her begin to push the large head of her cock against my ass.  She continued applying pressure, telling me to relax as her thick cock slipped slowly into me more and more.  

As she kept slowly pushing she kept whispering to me, "just relax bitch, take all 9 inches.."
After what seemed like an eternity, the dildo was fully inside of me as I felt Trista's hips resting against my ass. I moaned out as she slowly withdrew from me and pushed back in.  Soon enough she began a rhythm of sliding the cock in and out of my ass.  I was already breathing heavy and she was right, it did hurt quite a bit, but was also starting to feel good I hated to admit. 

Trista was soon fucking me hard, and my balls I felt swinging between my legs.  Each time they would come in contact with anything it was enough to almost make me scream. They were so filled with cum that so desperately wanted to escape.    Trista began to slap my ass on occasion, it was still red and tender from the earlier abuse it had endured.  

"How does that feel slut, do you like having a cock in your ass like this?  Do you like being treated like a whore with a little useless dick?"   

A million things were running through my mind at this point.  To my surprise, one of them was that I actually was to some extent enjoying it.  I wasn't sure if I liked the humiliation, the pain, the lack of control, not being able to cum or what, but something was making my cock try to get hard as it strained against the cage.  

As Trista continued to fuck my ass as hard as she could, she once again asked me if I wanted to cum.  And I did, I answered her more than anything.   She then asked, if I'd swallow my own cum.  I answered without thinking that I would, at this point I was pretty agreeable.  Alana asked if I had ever tasted a full load of cum before.  I managed to respond that I hadn't.  
Trista then said, "Well it's high time you start."  With that, Alana lifted my head up and in front of me was Jake's hard cock.  I had seen it before of course, but it was much closer this time around.  "Suck his cock," Alana whispered.  

As Trista continued to pound my ass from behind Alana held my chin up as Jake's cock moved slowly towards my mouth.  I noticed drops of pre-cum on the head of his cock.  As his cock passed between my lips, I tasted the pre-cum on my tongue.  I heard Alana again as she said softly, "good girl, now make him cum."

Jake's cock filled my mouth just as well as the one behind me filled my ass.  It was as if I was being pushed in two directions.  Trista would slam her plastic cock into my ass pushing me forward, making me gag slightly as Jake's cock would inevitably slide to the back of my throat.  He would thrust his hips forward pushing my ass into Trista.  I felt like a piston between the two of them.  They double-teamed me for a good 5 minutes.  Trista kept slapping my ass and calling me names as Jake would hold onto the back of my head and push his stiff cock deeper into my mouth.   Had you told me a week ago that I would be in the position; I could not have imagined it. Nor would I have imagined how turned I was.  My cock was once again straining against the cage and my balls felt like they might explode.  
Finally, I felt Jake stiffen and I heard Alana in my ear again.  She whispered, "Swallow his cum, be a good little whore."  At that moment, Jake's cock erupted and he filled my mouth with his thick cum.  It was a huge load that I had no choice but to try to swallow.  

After Jake came Trista removed her large plastic dildo from my ass.  I immediately collapsed on the couch and in a matter of moments I was asleep.  The last thing I thought before I fell asleep was that I was exhausted, sore, humiliated, and felt cheap and used.   And that I had loved it for some reason. 

Day 7

The next morning I awoke on the couch.  My ass was sore, my balls ached and my chin felt all crusty which I knew wasn't from drool.  Any chance I had to pretend that last night didn't happen wasn't an option as I was still wearing the stockings and heels along with the wig.  Trista was packing our stuff up as our flight left in a couple of hours.  She was already dressed and had showered.  

"Oh hey sleepyhead.  I was just going to wake you up," Trista said to me as she smiled.  "You best get in the shower we have to head to the airport soon."

I stumbled up off the couch.  I was about to take off the heels and Trista said, "Oh no sweetie.  It is best you learn to do the old 'walk of shame.'  A slut like you will do it often I'm sure."  So on wobbly legs I stumbled to the bathroom.   

Once in the bathroom, I looked in the mirror as my jaw hurt in a way I had never experienced before.   I saw that I still had a ton of makeup from the night before though it was all smeared.  The lipstick was smudged and I had a trace of Jake's cum down my chin. 

I began to think of how I had gotten to this point and immediately I was met with an ugly reality.  I still had this cage on.  My cock was still off limits to me and the only person with the key was the temptress in the other room.  She had to let me out though.  It was made of metal and I had to go through security in the airport.  There was no way I would be able to wear it through.  

It was funny how perspectives change.  A week ago when I arrived in Vegas, my only thought had been trying to get my cock inside of Trista.  A few days later it had been wanting to cum.  And now I wanted to simply have the freedom to touch it myself for fear of being pulled aside in the airport. 

Had she forgotten?  Was she going to let me out after my shower?  Did I have some other task to perform yet?  

No way could she forget, I walked right by her in thigh highs stockings and heels with nothing covering up the cage this morning.  So she clearly saw it was still on.  She hadn't forgotten.    What other task could there be that I had to perform?  She fucked me in front of strangers and made me suck another man's cock in front of his wife last night.   Plus there wasn't time for anything else was there?   Needless to say, my shower wasn't enjoyable as I tried to piece together the puzzle. 

I emerged from the shower and Trista had out a butt plug and a pair of panties and another pair of thigh high stockings and garter belt. 

"Since we're still in Vegas and the bet is still on, you can still wear this.  Once we're in the air though, you can feel free to go to the bathroom on the plane and remove whatever you wish.  Though keep in mind that those spaces are a bit cramped," Trista said as she smiled at me. 

Without complaint I began to get dressed and included those items that she laid out for me.  Putting the plug in was a terribly painful ordeal from the abuse my ass had taken the night before.  

When I was fully dressed Trista said we had better finish packing and head to the airport.  I was about to ask her about the cage but she stopped me.  "I know what you're going to ask, and don't worry, it will be taken care of.  I haven't forgotten, you've been very good and I will keep my promise to let you out of the cage."

The next hour was spent finishing packing, checking out of the hotel and driving to the airport.   In the car, Trista told me to lower my jeans as she drove.  I followed her instructions and lowered my pants exposing the panties and garter belt I had on.  

At a stoplight she removed the key from around her neck and said, "Ok take it off, but I ask that you wait for an hour before you cum yet. You waited a week, and I promise that I will not do anymore teasing but I would like to discuss this past week with you before you are allowed to cum.  That sound ok?"

While I wanted to masturbate right there, I had to admit that it wasn't an unreasonable request and so I obliged.   When I unlocked my cock, it immediately sprang to life.  Trista looked over, seeing my cock as hard as it could be, she giggled, "Oh look at that, it's cute."

She told me to pull my pants back up and to put the cage in her purse.  

We made it through security; Trista simply left the cage in her purse, and it went through the x-ray machine without incident.  I asked her what she would have said if they had asked her about it. She said, "I've found it best to tell the truth to TSA."  She then added that she wouldn't have had anything to be embarrassed about anyway.  That it would have been my face that would have been red as she explained it to them.   It was a fair point.  

We made it through security and as the case in today's world we had some time to kill.   Trista asked if I wanted to get a drink (it was already 10 am after all haha.)  I didn't really need one but then I didn't have anything else to do.  Plus it had been a while since I tried the "hair of the dog" remedy for the hangover I had. 

We sat down and ordered our drinks.  I had to admit this was strangely ironic as this was how our week had started out.  Over a drink when I made what turned out to be an unwise wager.  Trista then told me she wanted to talk about what had all happened. 

She asked me what thoughts I had on the week.  What I liked, what I didn't.  I went on for quite a while but I admitted that all in all the week had turned out to be a huge turn on and that I did have a lot of fun.   Fun that I didn't think I would have ever tried to have on my own had I not been forced.   She laughed and she said she preferred the phrase "strongly encouraged" instead of "forced." 

As we talked, Trista noticed me adjusting myself.  She laughed, "I see you're getting used to not having the cage on again.  I know I said I wouldn't tease you, so you know, that's not my intention here." I told her I knew that but that talking about it was almost as big of a turn on as actually doing the actions. 

She then asked me if I knew how it would have all turned out, if I would do it all over again.  I thought about this for a minute.  My response was, "In all honesty, most likely not.  But it's not because I didn't enjoy it. It's because I would chicken out.  That's why I used the word forced.  I felt like I had no choice.  I know I did, I mean I could have run away and had a locksmith help me.  It would have been a heck of a story but I could have done so.  But I wouldn't choose to do it again.  However, I would want you to make me do it again.  That's the key part.  I really enjoyed not being in control and not having a say in the matter.  Did I enjoy everything we did?  No not really.  But I did enjoy the not having a say in the matter.  The lack of control is what was enjoyable, especially as you proceeded to humiliating me at every opportunity.  But it was undeniably the greatest sexual week of my life, and I didn't even orgasm."

Trista smiled and said, "That's a good answer.  I can appreciate that.  I know you said you liked having no choice in the matter. But here's where you have to make a decision.  You said you enjoyed it.  When we get back home, we can do one of two things.  First, we can go back to the way things were before we came out here.  You can have your freedom and leer at me and go home at night and probably masturbate to thoughts of me and others."




Working with Trista Ch. 05



With that she reached into her purse and produced the cage and set it on the table.

"The second option," she began, "is that we continue what we started here."

She let that hang there in the air.   I think she was seeing if I would flat out refuse.  She smiled when I asked her what that would all entail.

"Well, the first thing it would entail is for you to go put on the cage, lock it and return the key to me."

"What else does it entail?"

"Those specifics would be revealed once you have the cage back on.  I'd like to tell you some stuff but I don't want to ruin any surprises.  You yourself said that one of the things you liked best was that you didn't know what was coming."

That was true I had said that. 

When I asked for at least a hint she said, "I will tell you what. If you return with the cage on and locked, and return the key to me.  I will have ready for you a list of 5 rules.  There may be more added, they may be amended in the future or they may be removed entirely.  However, these will be the rules we will have from the start.  You will have to follow them or there will be consequences."

I asked her what type of consequences.   She laughed and said, "You should have a pretty good idea by now.  But it will be most likely one of three things.  1) Your next orgasm will be pushed back. 2) You will be disciplined and it won't be pleasant.  3) You will be forced to do something you may not entirely enjoy.  Of course, keep in mind it could be all three things too, depending on what I decide."

I then asked how long she was thinking this arrangement would be for.  She replied, "Obviously, it will have to be for some length of time otherwise the threat of your next orgasm wouldn't mean much.  I mean if we only do it for a week, what's the big deal.  You've already done a week.  I would propose that we would revisit at one year, or put another way, after one year, you could choose to opt out.  I can terminate the arrangement at any time."

I thought for a moment.  A year seemed like such a long time, but the more I thought about being locked up in the cage again the harder my cock got. The more I thought about Trista having complete control over my cock the more my cock leaked pre-cum. The more I thought about her having the power to humiliate, use me and abuse me as she saw fit the more my balls ached.  And the more I thought about not having control and handing it over to her the more I knew what my decision would be.

"So what do I have to do?" I asked.  

"Simply go to the restroom and put the cage back on.  I would prefer you not cum before you do, though I did promise you that you would be able to.  So if you choose to masturbate in the stall before you put it on I cannot control that and it is your choice. Though I have to say that I would prefer it if you did not.  So put it on, return to me and hand me the key."

I started to stand up and she said, "Wait one more thing.  Be sure you realize what you're handing over.  You're handing over the power to cum.  When you do it will be the way I choose.  This was in a town full of people you do not know.  When we get back home, you will be surrounded by people you know and who know you.  Some of which may be collateral damage, in that they may see a 'different side' of you.  That may be intentional on my part or not.  But over the next year, undoubtedly, no matter how careful, someone may stumble onto something." 

The thought of that caused me to have to adjust myself once again.    I told her I would be right back.  I went into the restroom and I was tempted beyond belief to quickly masturbate and cum, but instead I waited for my erection to die down on its own and finally placed the cage on and locked it.  

As I was walking back, I would be lying if I didn't think about reconsidering.  After all if seemed like Trista had tried to warn me.  I was about to walk away and she called me back.  However, I continued on and handed her the key.   She told me to sit down and she had an evil grin on her face.  

"Did you cum?" she asked.

When I told her I didn't, her grin turned into a full-fledged smile.

She slid me a piece of paper and said, "Here are your rules/tasks for the next year for right now.  Remember I can choose to revise them as I see fit."

I opened the piece of paper and immediately my cock began to do its all too familiar strain against the cage as it tried to become hard. 

1. No body hair at all.  Remain shaven at all times. 
2. 6 orgasms in the next year to be decided by Trista 
3. All cum I produce I must eat.  
4. A minimum once per week, Trista will use the strap-on.
5. A minimum once per week, Trista will punish me. 
6. No more male underwear.
7. Only spandex allowed at the gym. 
8. Only lingerie outfits allowed to be worn at home. 
9. I will need to clean Trista's house in a maid outfit or lingerie, at least once per month. 
10. I will need to start an online blog which I will need to update at least once a week.  Complete with pictures, though they need not show my face. 

After I had read these rules I looked up at Trista.   I'm not quite sure what my reaction said exactly but she said, "These of course are just the start.  I also want you to think of a few things on the flight home.  Of your Facebook friends, I want you to do the following:  make a list and pick one male and one female friend that will see you in complete lingerie.  Furthermore, pick one male and female friend that will see you take it up the ass, keep in mind they may want to join in.  Finally, pick one male from your Facebook friends whose cock you will suck.  They may not be the same person either.  It has to be five different people.   The male and female can be a couple though.   While in the air, you can think it over.  You can tell me their names and show me their profiles when we land.   If you don't pick, I will pick for you.  Now let's go catch our flight."

It's going to be a fun and frustrating year.



Working with Trista Ch. 01



We ate lunch at one of the little cafes in the casino and Trista asked if I wanted to go with her to the pool. Boy did I ever, I had been looking forward to seeing her in a bikini since I first heard about the trip. She asked me what sort of swimming attire I had brought. I told her it was a standard pair of board shorts. That wouldn't do. She explained that as winner of the bet, she'd have to pick something else out. We went to the casino store where they had what seemed like an endless array of swimming attire. On the far wall, I noticed a few skimpy bikinis I wouldn't have minded seeing Trista in. 

My daydreaming was interrupted when Trista called me over to a section she was looking at. When I got there she held up this bright royal blue men's thong. "This will look perfect on you I think," she exclaimed. "What? No way," I immediately said, "there's nothing to it! There's no way I'm going out to the pool in that."

Trista just smiled at me and said, "Do you want to rub lotion on me so I don't burn? Up my legs and on my back? My inner thighs and even my chest? If you wear this for me, I'll let you run your hands all over me with lotion."

Well naturally, that somewhat sweetened the pot but I still wasn't sure. She then said I could wear my board shorts out to the pool but when we sat down I could take them off, so I'd not have to walk to the pool like that, I could somewhat get my bearings first. Between that and the prospect of getting to rub lotion all over her, I agreed. 

She took the thong up to the front where the gal at the register looked at the thong, at Trista, then at me and then back to Trista before ringing it up. Trista said to her, "The hope is that it won't look quite as small if he's wearing this." The girl giggled and said, "Of course," as I stood there my face as red as can be. 

From there we went upstairs to our respective rooms to get changed. I slipped on the thong and if it was possible, it looked even smaller once in it was on than it did in the store. I stared at my now hairless body in the mirror. I looked very different. The fact that this suit was royal blue sure seemed to call out "look at me" as well. I put on a tee shirt and my board shorts over the thong and waited for Trista to come get me. 

Once she was changed, we headed down to the pool, found two chairs next to each other, and Trista took off the tee shirt she wore. As I tried to keep my eyes from popping out of their sockets, she wore a very skimpy top that showed more of her boobs than it seemed to cover. She looked at me and said, "Ok let's see your new suit." I realized that my eyes weren't the only thing bulging out after seeing her bikini clad chest. I tried to explain to her that if I were to remove my other clothes, my hard-on would be visible but she didn't care, telling me that if I wanted to rub lotion on her now was the time. Slowly, I slipped down my shorts and removed my tee shirt, leaving me only in the royal blue thong. 

"Oh my," she said as she looked me over. "Stay standing up, I'll put some lotion on you so that you don't burn." She had me turn around so that my ass was facing the majority of the pool patrons as she put lotion on my back. I once again felt all eyes were on me. She paid special attention to apply a lot of lotion to my now exposed ass, rubbing in a lot of lotion, squeezing it at various times. When she was done she gave my ass a little slap and said all done and allowed me to finally sit down. She slipped off her shorts to reveal the high cut bikini bottoms she had on. Her bikini matched her new red nails perfectly and she looked great. 

She asked me to put lotion on her back as she laid down on her stomach. I was gladly up to the task; I sat down on the edge of her chair and began to rub lotion onto her back. "No no no," she told me, "stand up and bend over when you put lotion on me, I want people to be able to see your little swim suit." I wasn't exactly enthused about this development but at this point I'd have done just about anything so I stood up and bent over, giving those around us a very good view of my backside as I applied the lotion to her. 

While lying out there, we had a few drinks, so when it was time for me to apply lotion to her front, I was a lot more relaxed this time when I had to stand. However, as I was massaging the lotion into the top of her chest, my cock grew very hard, to which Trista said, "See I told you that little suit would make it look bigger." 

When our time at the pool was done, Trista had me gather up our stuff, and she mercifully allowed me to put on my board shorts. She did point out that she might not be so generous next time. 

She told me to get dressed, we were going shopping, I could wear whatever I wanted, and jeans would be fine. A little over a half hour later, we were pulling up to what could be best described as an "adult store." Needless to say, I was very excited to go in here, hoping that this would translate well into whatever was to happen tonight. My balls were very achy at this point, from the partial blowjob last night, to this morning's workout and waxing, to the pool. I was being kept on edge for quite a while at least by my standards. 

When we went in, we were greeted by a guy behind the counter dressed in tight jeans, a black leather vest, boots with 2 inch heels and tattoos up each arm, who introduced himself as Bolt. Nice name I thought to myself. Trista introduced herself saying that she was the person who had called earlier. Bolt remembered her and gave us the quick layout of the store. He pointed out the dressing room, encouraged us to try stuff on, and if we had any questions or needed any opinions to not hesitate to ask as the store was very slow that day. I must say for being a bit on the goofy looking side, he seemed very helpful. 

Trista immediately took my hand and went for the clothing. At first I thought "oh here we go again" but I was surprised when we went to the women's section and she started asking if I thought she'd look good in some of the outfits. She pulled out a school girl skirt, a black vinyl cat-suit and a white corset. Of course I thought she'd look great in any of them and didn't hesitate to tell her so. When she said she'd try them on, I thought I had hit the jackpot. 

The first thing she tried on was the corset. It looked great. Bolt actually had to help her lace up and tighten it in the back but when she came out of the dressing room her boobs looked like they were about to spill out of it. My cock instantly sprang to attention. She asked what I thought and I stammered she looked amazing. Bolt and Trista both chuckled when Trista pointed out they could notice my enthusiasm through my jeans. "Keep that little thing under control," she warned me. 

The second outfit didn't do anything to help my erection as she came out dressed as a school girl. The too short checkered skirt certainly did the trick as I felt my jeans grow even tighter. Bolt loved that outfit. Trista turned around and bent over, showing off her tight ass. Once again, she pointed out my hard cock and said I needed to keep it under control. 

The final outfit was too much as I almost came in my pants. She came out in this skin tight black vinyl cat suit. It was absolutely jaw dropping the way the vinyl clung to her breasts, her hips and her ass. She asked if I liked this one and I said I certainly did. She asked if I'd submit to her in this outfit and I said I surely would. She then said that that sounded like a good idea and she whispered something to Bolt, who then disappeared. 

"So you'd submit to me in this outfit, is that right?" Trista asked as she pressed up against me. When I told her I would, she asked, "So I could tie you up? Take control of you?" Oh was she ever turning me on now, I would have agreed to anything at this point. 

She reached down and grabbed my cock through my jeans, "can I be in control of this too?" I nodded yes as fast as I could as I noticed Bolt handed her a pair of handcuffs. She told me to hold out my hands, which I did. She put a cuff on one wrist and lifted my arms up, cuffing me around the metal bar holding the dressing room curtain. 

"I guess you were right, you would let me tie you up," Trista beamed. "Now let's see what we can do about what else you agreed to." She reached down and unzipped my pants and slid them down leaving me in only my boxers. Within moments those too were off, leaving me in only my tee shirt and my hard cock sticking straight out, both Trista and Bolt looking at me. 

"Um, this is a little more than I was thinking, anyone could walk in here," I stammered. Trista laughed and said that Bolt had locked the door to make sure that it wouldn't be an issue. "Plus we have to figure out a way I can control that cock of yours," she said as she took my cock in her hands and began stroking it. She turned to Bolt asking him if they had anything in the store that might be useful in this instance. He said he had just the thing and left the room as Trista continued to stroke my rock hard cock. 

Bolt returned with a metal device, explaining to Trista that it was a chastity device and would prevent me from getting hard at all, let alone cumming but would allow me to go to the bathroom so it never had to come off. It was an impressive looking device, stainless steel that would allow me to partially get hard but not fully as it curved down. Bolt said the official name was the bird cage. It came with a small padlock that had a key, and Bolt explained that unless I took it to a locksmith or something like that to cut it off, the only way it was coming off was with the key. I started to voice my displeasure but Trista hushed me, quickly reminding me that I had just told her I was up for this and to not forget she won the bet in the first place. 

Trista squeezed my balls, forcing me to cry out as she said, "Now you want this device on don't you?" With her squeezing me like that I quickly said I agreed. She turned to Bolt and asked how they could get the device on since my cock was so hard. 

He had an idea and quickly returned with a cup of ice water. Trista dunked my cock and balls in the ice water which caused me to gasp and quickly returned my cock to its normal state. Trista then asked me, "Do you really not want me to put this on you?" 

I took her at her word and said, "No I really don't." When she said that she understood I felt so relieved. But that lasted only a few seconds when she then said, "That's fine, Bolt will you please put this device on him?"

With that Bolt bent over, and began to man-handle (literally) my cock and balls, forcing them into this chastity device. I must say that while I was not at all enjoying my predicament, if not for the device, Bolt's handling of me would have caused my erection to return. As Bolt was holding my cock in one hand and putting the device on, I saw Trista take a picture with her phone. "Smile," she said as I heard the camera snap.

When Bolt clasped the lock and handed the key to Trista, he said, "All locked up, I like the no hair too, very nice on him." 

Trista just smiled and asked me, "How does that device feel now slut?" I said it felt ok and wasn't uncomfortable. Trista then thanked Bolt for helping her and said she may be back before our trip was over. After that she un-cuffed me and allowed me to put my jeans back on. She made a production of slipping the tiny key between her breasts for as she called it "safe-keeping."

I watched as the tiny key disappeared and began to think that maybe this trip wasn't going to go exactly as I had hoped. 

We ate dinner back at the hotel, the chastity device always on my mind. Not just from the fact that my cock could no longer get hard, but because of the extra weight I felt. While not heavy, the extra weight was a tiny reminder that I was definitely not in control at this point. 

After dinner, Trista told me she was going to take me out and that I should get a little dressed up. Back in the room as I was changing, I stared at myself in the mirror, this contraption hanging from my cock, not allowing me to even touch myself. As I stood there and thought about it, the thought of Trista having control over me must have been quite a turn-on as my cock tried it's best to get hard, but to no avail as it struggled against the device. I resigned myself to the fact that I wasn't going to get out of this until Trista allowed me to, but even that was a turn-on for me. 

I was dressed when Trista knocked on my door, I opened it and she was in a very shiny tight red dress. Immediately I was reminded that I was wearing the device upon seeing her in that outfit. If that wasn't enough, she immediately reached out and unzipped my pants. Taking my locked up cock in her hands, she started fondling my exposed balls and asked me if I was enjoying my newfound confinement. I told her that I wouldn't mind being let out. She laughed and said, "All in good time as long as you behave" as she zipped my pants back up.

The cab dropped us off at a Gentlemen's club. Trista explained to me on the way over, she wanted to test the device to ensure it would work. Over the next couple of hours, half naked and fully naked women danced all over me. Each one of them looked at me funny as they would grind on me and feel the metal device encasing my cock. Trista took the time to explain to each one of them what it was and why it was on me. One of the dancers even asked to see it, at which point Trista had me lower my pants and show them the device. Trista smiled as each dancer tried their hardest to get me erect. While each had me aroused, none could make my cock erect to Trista's delight. My balls were filled with cum and just begging for release by the end of the night. Finally, Trista said it was time to head back to the hotel. 

I was very happy with this news, holding out hope that I'd be released from this metal prison and be allowed to cum. When we arrived back at the hotel, Trista followed me up to my room, and once I had the door open, she was already fumbling at the zipper on my pants once again. 

She had my metal enclosed cock out in no time and she roughly fondled my now aching balls. She kept asking if I enjoyed the dancers and if I wanted to cum, everything she was saying was making me ache more. 

Trista pushed me back onto the bed, and she stared down at me. "Look at that little cock," she said, "it wants so much to get hard but it just can't. It makes me so wet."

At that point she lifted her dress, and lowered the thong she was wearing to reveal she was totally shaven and very aroused. She crawled up onto the bed as my eyes were transfixed on her glistening pussy. 

"You're going to make me cum right now aren't you my little slut," she smiled as she positioned herself above my mouth. "Now let that tongue go to work." 

Over the next half hour or so, she grinded her pussy on my face, cumming multiple times as my tongue darted in and out of her. Occasionally she would reach back and squeeze my extremely full balls or pinch my nipples but she never removed her pussy from my tongue. Finally, she rolled off of me and I thought that finally it was going to be my turn. Naturally, I had been testing the limits of my bonds this entire time and I thought for sure she would be reciprocating soon. 

"Well, I'm going to call it a night," she said, "but I definitely plan to use that tongue again soon."

She must have seen the disappointment on my face because she then said, "Oh you thought that I'd let you out of your little device? That's so cute. It hasn't even been 24 hours yet. I didn't bring the key with me anyway. But I promise you, if you're good, I'll consider letting you out. In the meantime, don't cum. Though I suppose I don't have to tell you that, it's not like you can anyway, right?"

She giggled as she wished me a good night and went to her own room. I would like to be able to say I fell asleep right away but that wouldn't be true. Each movement caused my heavy balls to ache and my mind raced as I layed in bed that night. Eventually after a couple of hours I did finally manage to drift off to sleep.