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Pool Boy Gets Dressed Up Ch. 01

By: tonyl65



I loved my job as a part-time pool maintenance man, or pool boy as everyone loves to call it. I just finished high school and enrolled in night classes at the local junior college, that don't start until September. Having night classes will allow me to work my part time job during the day. I loved going from beautiful house to beautiful house, cleaning and testing pools, wearing only shorts, a tank top, and flip flops as my uniform. Florida is so nice in the early summer. Most of my customers are at work which leaves me time to clean the pools and sometimes take a nice dip to cool off. I am really shy so I prefer to be by myself all day and not have to interact with people, while I am still going through the awkward teens. 

My name is Brandon; I am 5 foot 6, 120 pounds, dark brown hair which I keep real short so that when I swim I just have to shake the water off without worrying about weird hair. Thanks to my Italian genes, I have green eyes and a smooth almost hairless body. I am really self-conscious about my body. I just turned 18 and I don't think I have finished puberty. The hair on my legs only grows on my front shins. I only have a couple hairs in my arm pits and not much more grows around my cock. I have small budding breasts with large puffy areolas. My nipples are large and stick out over 1/4 inch. I shave my cock, balls, legs, and even my arm pit hair, just because I prefer the more even look over that intermittent sparse hair growth I have going. My biggest embarrassment is my cock; it is still the size of a little boy's. My cock is about 4 and a half inches hard and really skinny, a real pencil dick. I am hoping this will all develop one day soon. 

One particular day it was hotter than normal and the pool I was working on was enclosed in an atrium room off the home's living room. There were huge picture windows and sliding doors that allowed anyone in the home to see the beautiful patio, bar, spa, pool, and waterfall. It is my job to make sure that all the rocks and tiles are kept algae free and the pool balances are perfect so that the water is crystal clear. I was only wearing a white small speedo and tank top, since nobody is ever home during the day. 

I only met the owners once when I had to come on a Saturday. The wife is a gorgeous blonde woman that is at least 6 foot tall, nice set of boobs, slender build, and legs that go on forever. Her husband was about 6 foot 4 inches and looked like a Greek God, shiny black hair, steel blue eyes, and thick dark black hair on his olive tone arms and legs. They introduced themselves as Debra and Don, and they both looked to be in their early 50's, very wealthy, and in very good shape for their age. 

I had introduced myself and told them that I usually come to their home on Fridays but I had finals and my school schedule changed for this week only. They said that they were pleased with my work, and even though I was out of school they hoped that I would continue on as their maintenance person. Then Don made a point to let me know that if I had to leave the company for any reason that he was to see him first and that he would at least offer to keep me on as a side job and would work around any schedule I may have. 

Debra showed me around the pool area and bar, she told me to always help myself to anything they had in the bar as long as I didn't drink and drive. As she said that last part she put her arm around my shoulder and pulled me in for a quick hug pressing my face to the side of her exposed breast, then laughed at how red I had gotten. I thanked them and went about my business cleaning the pool while they drank and talked to each other. 

That was in May at the end of my semester and now here it was mid-July and I had never run into either Debra or Don, so I felt safe wearing only my speedos. I was bent over the waterfall rocks, scrubbing them down, when I heard the sliding glass door open up. I looked up to see Debra as she was walking out of the house. She was wearing a hot bright orange bikini, that was really just small patches covering her nipples, a little triangle covering her pussy lips, and held up by a little string around her waist and ran down the crack of her hard as rocks ass cheeks. She was caring a towel and a book. 

'Oh shit, I'm only wearing my speedos,' I thought to myself as I jumped up, grabbed my shorts, and quickly bent over to put them on. 

Debra called out to me from across the pool "Hi Brandon, how are you doing sweetie?" 

I stumbled something stupid, "Um, fine Mrs, ur um Deb..Debra ma'am." 

Debra shot me a quick look before she started to scold me, "Brandon don't you ever call me Ma'am, I'm not that old. My name is Debra or Miss Debra if you wish, and for gosh sakes stop fumbling with those shorts, it's hot and you look just fine in your cute little speedo there, now put those shorts back down and go about doing your business." 

Though it came out kind of rough and loud, I'm sure she didn't mean it like that. I dropped my shorts right down as I was told and quickly began to apologize for calling her ma'am, "Yes ma'am, I mean Debra, ur..uh.. Miss Debra." 

'Stupid, stupid, stupid' I thought to myself, this is why I don't have girlfriends I get all tongue tied and stupid around beautiful women, and I could feel myself turn ten shades of red. 

Debra put her towel and book down on one of the lounge chairs and then walked over to the bar. "Hey, Brandon do you want something cool to drink?" Debra called out to me. 

"Uh ya sure that would be great thank you Ma...um Deb..Miss Debra." Crap, idiot strikes again. 

Debra laughed at me "Hey, Brandon how about I just get you drink and you walk over to that chair and sit down, that way you don't have to stumble on your words every time you open your pretty little mouth?" 

Rather than make a bigger ass of myself, I put the scrub brush down and walked over to the lounge chair and sat down. Debra walked over to me and handed me a drink. As I took the drink from her hand it was clear that I was nervous as the drink was shaking in my hand making the ice jingle in the glass. 

"Calm down there little guy nobody is going to hurt you." To add insult to injury she said that and patted me on the head like a little kid. 

I was eye level, almost, with her crotch and I could see the bright orange patch covering her clit which was not covering it at all. Her pussy lips were sticking out from the sides of the material, which was attempting to be a bathing suit. I almost lost it then and there; thank god she pulled away and sat down with her drink. 

Debra attempted to get me to open up, "So Brandon what do you do when you're not in school or cleaning pools?" 

I took a quick drink thinking it was just a cola but it had a lot of rum in it and I choked. Debra laughed at me, and in a patronizing tone said, "You ok there honey? Did I make it too strong for you?" 

"No, um, I just wasn't expecting it to have booze in it. I'm good, thank you." I tried to pull off coolness by taking a large drink of the rum and coke, but already having choked my voice sounded like a little boy trying to act like a grown-up. 

Debra reiterated her question "Ok there stud. So what do you do when you're not here in my backyard running around in a little skimpy bikini bottom?" This made me blush again so I took a long swig of my drink, and choked a little again. 

It was getting really hot now and I was getting light headed and loosening up a bit as I answered her question, "Nothing really, just play video games and surf the web mostly." 

Debra reached over and grabbed my thigh, "What? No girlfriend to keep you busy Brandon? I'm shocked, good looking boy like you I would think girls would be all over you." 

She ran her hand down my thigh to my knee, "My, your leg is as smooth as mine." At that last comment I jerked my leg a bit and her hand came off my knee, I was again embarrassed. 

She shot me a firm look again, "Oh don't be like that Brandon, it's no big deal that you shave. In fact, I find it a nice change from Don's big manly hairy legs." 

I confessed that I shaved the little hair I did have because I thought it looked stupid growing in sparse patches on my legs, after the words left my mouth I wanted to crawl in a hole and die. 

Instead Debra just went with it like it was no big deal, "That's very sensible, and I suppose you shave your cock and balls so you can wear that little bikini bottom? That's why I shave my pussy too, seems we have some things in common don't we honey?" 

I agreed with her as I took another gulp of my drink, "Yes Miss Debra I guess we do, thank you for not thinking I'm weird for shaving. I've never told anybody that before." 

Debra smiled at me and placed her hand back on my thigh, "Oh sweetie you can tell Miss Debra anything you want, this is totally safe zone for you. Just relax. So why don't you date girls, afraid they will find out your little secret?" Debra began to lightly caress my leg. 

I nervously downed the rest of my drink. Debra was quick to get up and make me another. As she returned with our freshened drinks, instead of returning to her lounge chair she sat next to me, forcing me to move over a bit to let her sit. Before I could pull my knees up toward my chest, and hide my hardening cock, Debra had already put her left hand across my legs and laid her upper body across me pinning my legs down. 

I took another long swig of the rum and coke to settle my nerves. I tried a quick tug of my shirt to try and hide my crotch; no luck the shirt was too damn short. Debra lay across my legs facing me, her right hand softly stroked my thigh, "So you say you surf the web, I bet you surf a lot of porn don't you Brandon? Remember anything you say here stays here." 

Debra was talking in the softest and most sultry voice I have ever heard. Her voice had me mesmerized. My mouth just opened up and I could hear myself talking and I couldn't stop myself, "I surf porn, I like watching videos of people having sex while I jackoff." 

""People" what an interesting word to use. Do you like watching women and men fuck each other, or maybe two women getting it on? Is that what does it for you, lesbian porn?" Debra was prodding me and I must have had a blank and shocked expression on my face.

"No? Then bi porn, a woman getting fucked in her pussy while her man takes it up his ass?" My cock twitched at that and I could see a smile cross her face.

Debra continued to torment me, "Maybe a little curious and you peaked at gay porn, two guys fucking each other and sucking on each other's cocks, have you looked at gay porn Brandon?" Again, my cock twitched and I could feel a drop of cum seep out through my suit.

"Oh everyone is curious Brandon don't feel bad. Boy's like to look at men's cocks to see what they might grow up to be like. I'm sure you've checked out the boys in the shower after gym class haven't you? Your dad while he was changing maybe?" Debra just kept looking into my eyes and leaned her body closer to me. 

Her body shifted and I could feel her waist pressing up against my little cock and balls. Then she took her hand and ran a finger down my face, it felt so good. I heard her voice again "Have you ever watched Tranny porn Brandy baby? Do you like seeing boys dressed in silky nylons and a pretty lacy bra pressing against their poky little nipples? Feel a real man put his big hairy body on top of them as he feeds his big man cock in their waiting mouth?" 

I lost it, I threw my head back, my legs started to shake, and I squeezed my cock as hard as I could to hold back the cum. When my little orgasm stopped, I released the tension on my cock. I could feel a big glob of cum seep out of my cock head. Looking down at my lap I could see that my cock was pressed tight against my speedo and my cum came out through the nylon forming a big glob right there on my cock head. I was so embarrassed; I needed a hole to crawl into.

I looked up at Debra and she was staring at me with a big wicked smile on her face. Debra leaned back away from me and followed my eyes down to my lap. I watched as her hand came down to my cock and her finger scooped up the blob of cum off my speedos. Her hand came up to my face as I heard her say in that sultry voice, "Good little sluts always clean their messes up Brandy sweetie, now open your mouth baby." 

Without even thinking, or having any sense of control, my mouth opened a bit, her finger entered my mouth, and then she fed me my cum. "Now be a good dear and clean Miss Debra's finger off." I just closed my mouth around her finger and closed my eyes. My tongue took on a mind of its own as I slowly searched out the cum off her finger. 

"That's it baby suck on it, feel that nice thick juice in your mouth. Play with it, get to know its feel and taste." Her finger slowly pulled out of my mouth and I was left with my cum on my tongue. I moved it around feeling the thick slippery feeling, it was heavenly. 

I never tasted cum before, let alone my own. As often as I jack off I never thought to try it. It tasted really good. Then I realized that I was eating my own cum in front of a woman and she all but made me confess my deepest desires. I turned my head away from her and I tried to twist out from under her but she had me pinned down, her hand was stroking my leg and moving up to my speedos. My cock was hard as a rock and straining to pop out the top of my speedos. I was dripping so much that the wet spot was growing bigger and bigger.

I felt a firm grip take hold of my shoulder, "BRANDON STOP" Debra yelled at me. 

I froze at the sound of her voice. "Brandon, stop it now, relax. There is nothing to be ashamed or embarrassed about. I am sorry I brought up the subject; I didn't mean to make you feel so bad. Sometimes I see a sexy young man and I just have to know what he desires. When I saw that you shaved your legs I had a hunch you might want those legs covered in silky nylons. By the little orgasm you had, I think I was right wasn't I sweetie?" 

My eyes went wide open and my voice was gone. I could feel the tears well up in my eyes and my chest started to feel heavy as I fought back the emotion. Debra looked at me, "It's perfectly fine with me baby, I said this was your safe haven. I would never tell another sole what goes on here. I think it is extremely sexy to see a man in girly things. In fact if you want to, I would be more than happy to let you dress up here as you want, it will be our little secret?" 

I didn't know what to think. Sure I surfed porn on the web, who doesn't? Like most people I "accidentally" would come across bi porn and it made me wonder what it would be like to be with a man and a woman. I was still a virgin so I have nothing to compare anything to, except my right hand. I didn't know what I wanted, men or women. I was confused. Gay porn was cool but it always seemed that the guys just jump on each other and go for it, no playing or seduction in those movies. 

The tranny porn was hot. I loved watching the story lines where the guy doesn't know he is making out with a guy until he finally drops his panties. I love to watch the tranny films where the boys have nice real tits and not just stuffed bras. But now I am sitting in front of an almost naked goddess and she wants me to play dress up with her. I was so confused, and what if Don found out? I would lose my job and probably get the shit kicked out of me. 

I shyly told Debra, "Thanks, but I couldn't. I have never done anything like that. I would feel funny undressing in front of a beautiful woman let alone wear girls clothes. What about your husband, what if he came home and caught me? He scares me." 

Debra looked at me and smiled, "Oh Don is out of town more often than not, don't worry about him. I just want to help you find what makes you happy, just try a few things and we will find your true sexual calling, trust me. It will be like having my own little play friend. Besides Don is gone for a week, it's Friday, and I have no plans all weekend." 

With that she leaned over and gave me a quick peck on the lips, and then she put her hand on my still hard cock and said, "Looks like someone wants to play." as she rubbed my cock. 

Debra sat up, hooked her fingers on either side of my speedos, and pulled them down and off my legs. My cock slapped back against my tshirt as my hands quickly tried to cover myself. Debra easily slapped away my hands before I could cover up, "Come on baby now is not the time to be shy, let Miss Debra see what we have to work with."

Debra grabbed my tshirt and pulled it up and over my head with such force that I couldn't even stop my arms as they went straight up in the air with my shirt. Debra threw my shirt off to the side and I crossed my arms to cover my budding nipples. 

Debra would have none of that, "Hands down Mr." Debra commanded, and my arms went straight to my side. I felt my face turning bright red as I tried to turn my head in shame.

Debra grabbed my chin and turned my face back to her so we could look into each other's eyes, "Stop being so embarrassed, you have a lovely body." 

Debra looked me over, "OH MY, those budding titties are lovely." as she said that her hand left my chin and softly touched my left nipple. I let out a soft moan of pleasure. Nobody has ever touched my nipples before. It was like electric shocks went through my body and right down to my balls. My cock flinched and my nipples started to get hard and poke out. 

"You like that don't you baby, see it's all about feeling good. You have the biggest areolas I have seen on a man, and bigger than a few women I know, simply lovely." 

She was staring at my nipples, massaging them, rubbing them, lightly pinching, and pulling the nipples making them really hard. Almost to herself she said, "Oh yes this is going to be the best transformation ever." I didn't know what she meant and I really didn't care, I was just enjoying the feeling of someone touching me.

Just as fast as she pulled my speedo off, she crawled in between my legs. I felt her hair fall on my stomach as she put her head in my lap and I felt a warm wet sensation around my cock. It was so hot and her tongue was all over my cock. I was so small she actually took my entire cock and balls into her mouth. Her tongue darted out behind my balls, then back in her mouth swirling her tongue around my balls. I couldn't hold back, "Oh god no, I'm cumming, stop please stop I can't hold it back." with that I felt my cock tighten up and spurt three or four powerful bursts of cum into Debra's mouth.

Debra pulled up a little and sucked out some more cum. My head was spinning, my first blow job. Debra lifted her head off my deflating cock, reached her hand behind my head, and pulled me in for a kiss. Without thinking I just let her guide me to her lips. Her tongue forced itself into my mouth. The grip on the back of my head became tighter as she held our kiss. She parted her lips and my mouth was filled with her tongue. I felt a warm liquid flood into my mouth. We continued to let our tongues dance until she pulled off my mouth. She held me so close that our noses stayed touching, "All good sluts clean up after themselves, now swallow your load honey." 

The first time she fed me just little bit of cum I didn't think it was bad at all. This time I have a mouth full of my own cum, fresh my cock. I was too turned on not to have swallowed. It felt so good going down, and I actually liked the taste. I looked back at Debra with a proud smile on my face.

Debra stood up and held out her hand for me to take. I took her hand and she pulled me up next to her. She towered over me like a beautiful amazon woman, at least in my mind, "Come on, let's take a swim in the pool." with that she pulled me towards the pool. 

When we got to the edge of the pool she pushed me in the water. When I came up laughing, she was untying her strings on her bikini. She released her breast first, tossing her top onto the chair. Her breast were the most beautiful I have ever seen. Her 36b's were held nice and high and firm on her chest. They each had large pink areolas with large protruding nipples, and her right one was pierced with a gold ring. 


Pool Boy Gets Dressed Up Ch. 01



Then she pulled off her bottoms and tossed them onto the chair as well. Her pussy was cleanly shaven. I have seen many pussies watching porn, but Debra's pussy was perfect. Her pussy lips were slightly swollen and at the top it almost looked like a little cock sticking out, that must be her Clitoris, just perfect. 

Debra dove into the water and came up next to me. She kissed me again, and then she pushed away and started to do laps. When she reached the end of the pool she called out to me, "Come on do some laps with me." 

I swam over to her and got ready to push off for some laps, "Don likes his women toned, and swimming is the perfect low impact exercise. I do 50 laps a day, are you ready?" 

I was a swimmer, 50 laps? No problem. Debra never stopped and never slowed her speed until all 50 laps were completed. It was a good workout. Debra lifted herself out of the pool and dropped into the spa which was attached to the pool. I followed as I sunk into the nice warm, bubbly water. Now I was getting really relaxed and Debra made it all seem so natural.

We sat soaking for about 15 minutes when Debra lifted herself up onto the edge of the spa, leaving her legs dangling in the water. I thought that that was the signal that spa time was over, so I started to get up and get out. 

Debra grabbed my shoulder, "Oh no you don't sweetie. You're not done yet. Come over here to me, we have a couple more issues to discuss." 

Gliding in the water, I moved towards her. I was only able to focus on her pussy staring me in the face. I got close enough that she grabbed my head and pulled my face to her pussy, "Pussy eating lesson time, I sucked your little pecker, now it's your turn to make me feel good." 

As she said this she pulled my mouth right to her pussy, and then she pulled and pushed my head side to side grinding my face all over her pussy. It was so soft and warm. Her pussy lips dragged across my lips and face. I took a deep breath so that I could smell my first pussy, it was intoxicating. "You like that do you? Now stick your tongue out and lick my pussy. Then suck on those pussy lips." 

I took her instruction and pushed my tongue into her warm pussy. It felt so good, so warm and soft. I sucked in her pussy lips and used my tongue to explore the feel and taste. I must have been doing something right by the sounds of Debra's moans "Mmmm, yes that's my baby, suck those lips, get to know them. Lick up and down my snatch, push your tongue way in and move it around. That's so nice, taste my pussy juice baby." 

Her hands were massaging my head, but firmly holding me in place eating her pussy. I was in heaven. I licked and sucked up and down her pussy. I felt a hard nub at the top of her pussy and really worked my tongue on that. Debra started to move around on the edge of the spa, then she started to moan louder, "Oh yes that's it keep going, I'm going to cum mmmmmm." 

Debra pushed my face hard against her pussy, and held it in place as her body shook and convulsed. My nose and mouth were enveloped by her pussy lips. My tongue was darting around in the soft hot folds of her pussy. I could feel her thighs clamp down against my cheeks and start to shake. A warm flood of liquid filled my mouth. She was cumming in my mouth. It tasted nothing like my cum, but it was sweet and warm, thinner than mine. I drank it in like sweet nectar. 

Debra finally released her grip and pulled me up to her and kissed me hard. She licked my face all over cleaning her juices. "Don likes his girls to clean up their messes. That was so fucking great." 

I felt so proud I was able to eat my first pussy and make her cum doing it, a natural. Debra slinked back in the water and pulled me to her. "That was amazing, I needed that. Did you like eating pussy baby?" 

I was elated "Oh god yes, it was the best thing I have ever done. I hope I did it right?" 

Debra looked at me, "You did it just right." as she said that I felt her hand move to my hard cock, "You know you have the cutest little cocklet I've ever seen." 

Then her hand went up to my nipples and started to caress them. My nipples are so sensitive, as soon as she touched them my cock jerked and my head went back to enjoy the sensation, "You love your titties played with like that don't you baby?" she cooed in my ear. 

Just when I thought the subject was dropped, Debra began her questioning again, "Now tell Miss Debra what else excites you hummm? You like watching the tranny porn? I bet you picture yourself all dressed up waiting for a big hairy man to lie on top of his little pussy boy? I bet you have a nice tight pussy that is dying to have a nice cock pop that cherry? Hmmm baby, tell Miss Debra." 

She kept whispering in my ear and massaging my nipples, I was about to explode. I didn't want to admit anything, but she had me so horny with visions of me dressed in a bra and pretty panties, and a man's body, no I wanted Don's body pressing against me. Oh my god what was I thinking, no, no, stop, "Yes, yes, I want to dress like a little sissy slut, oh god." I turned my head away in shame, again. 

Debra kissed my ear, "There that wasn't so bad to admit now was it sweetie. Miss Debra is here; she can make all your wishes come true here in our own little world here." 

Debra pulled away, leaving me panting and almost in tears. I just confessed something out loud that I barely admitted to myself. Debra got out of the spa and told me to follow her. Like a puppy dog I did as she commanded. We went over to our chairs and Debra handed me a towel so that we could dry off. Then she grabbed my hand, both still naked, and then walked in the house. We went through the glass doors into a huge, nicely decorated, living room with plush carpet that felt wonderful on my feet. We went through a foyer to a wide open staircase leading upstairs. 

She pulled me along to a set of double doors that lead into the master bedroom. Debra opened the doors to a room the size of my parent's house. Large four poster bed, couch and chairs set for conversation that faced a raised marble fireplace with glass doors that looked through into the bathroom. Debra continued to guide me through into the bathroom. The bathroom was all white marble floors with a huge Jacuzzi tub next to the fireplace. There was a large walk in shower that looked like there were at least twenty shower head nozzles attached to the walls and some attached to hand held wands, all set in beautiful stone and glass. As if you couldn't take it all in with one sweep of your eyes, one wall was mirrored so no matter where you looked you could see yourself and the entire bathroom. 

Debra led me into the shower and turned it on. Debra flipped a switch on the wall and steam began to form. Debra turned to face me, "Well are you ready to play Brandy?" 

I was still trying to soak it all in and answered in a stunned fashion, "I guess so Miss Debra." 

"You 'guess so'? Either you're in or you're out, I don't have time to play games. I want a friend that I can truly trust, one that we can share the upmost intimate things with and I know it will stay between us. I thought I could see that in you Brandon, I thought you confessing some of your desires to me were a sign that you could trust me? Maybe I was misreading you?" Debra was firm and she hurt my feelings.

Oh my god no, I felt really bad. As usual, I was stupid in the choice of words, "Please Miss Debra, I mean, yes I am ready to play. Please trust me, I trust you with anything. I've never done anything like this before today. You make me feel like a man." 

Debra looked at me shocked, "Like a man? Oh sweet baby you're nothing like a man, you have a little pecker the size of a five year old, your tits are budding like a pubescent teenage girl, and you dream of sucking a guy's cock and getting fucked. No sweetie you're more of my little girlfriend here in this house. I want to dress you all up like a little tranny slut and we can watch gay and bi porn together and suck each other's tits, won't that be fun?" 

I felt slapped in the face, I thought I was going to be her male lover, and now my cock was shrinking back down to a little nub and I was starting to cry. Debra came up to me and hugged me, "Shhh, shhh, it's ok Brandy you go and cry your little eyes out. See Miss Debra loves your tongue on my clit, you make me feel wonderful, but that pathetic baby cock will never satisfy my pussy. But that's ok. There are so many other ways to make each other cum, it will blow your mind. Now come here and suck my titties like a good girl." 

I wasn't even comprehending anything, I just heard her ask to have her titties sucked, so I let her push my face to her breast and she used her hand to hold her tit while I moved over to it and started to suck on her nipple like a little baby. "There, there, that's better isn't it? Yes suck Miss Debra's nipple, relax baby." 

The steam and the hot water were relaxing. Our high school gym showers weren't this big and there was a large drain on the floor. Debra grabbed a bottle off one of the shelves and squirted some pink liquid soap in her hand, then she pulled me off her tit and started to rub it all over my body, it smelled like Rose petals. Then she grabbed one of the shower wands off the wall, but this had a long tube with holes on it and a valve to turn the water on and off. 

Debra instructed me to get on the floor, on my hands and knees. I asked her why? "Trust me Brandy baby, when we shower we have to clean everywhere or playing sexy games is not as much fun. You'll see what I mean." 

As I lowered myself down to the floor, Debra squirted more gel on my back and started to rub it in. It felt so good to get a massage. Then the gel dripped down the crack of my ass and Debra's fingers stopped it right at my hole. She rubbed the gel all up and down my crack, then she pushed a finger in my hole. When I felt the intrusion my head dropped down and instead of pulling away I pushed back against her finger. "MMM, nice baby, you like that do you? This is just a little bit of pleasure, wait until you see what you will be getting later." 

She continued to run her finger in and out of my ass for a few more strokes then I felt something bigger, blunt, and more rounded, pushing against my slippery hole. "Take a deep breath sweetie, then release it and push back like you want to take a shit." 

I took a breath in and when I blew out through my teeth I bared down like I was taking a shit and the shower wand pushed in my ass. The soap made it really slippery and her fingering must have prepped me because there was just a slight twinge of pain before I felt my ass envelope around the device as it entered me. I bowed me head a little and groaned "Oh, mmmmmm." 

I could hear Debra giggle a little, "Oh baby you haven't felt anything yet. Your little boy pussy is hot and ready for pleasure, I can tell. I think we are going unleash that sexy little slut in you." She laughed some more and gave my ass a nice comforting swat.

Now the uncomfortable part as I felt the warm water rush into my bowels. The pressure of the water as it filled me up made me groan in discomfort "UGH, I think I'm full, oh god I'm full." 

Debra laughed, "We just started, we not only have to clean you out, but we have to stretch you out as well. Now hold back as long as you can, then I will pull the nozzle out and you sit on that drain hole and let it flow out." 

'Really?' I thought to myself, "Miss Debra I can't go in the shower, I can make it to the toilet." 

Debra swatted my ass again, but harder this time, "The hell you will, you will get one step out of the shower and make a mess all over my bathroom, besides you have to do this at least two more times so get used to it. I do this every day, it feels so good to be clean, you just wait and see." 

Debra stopped the water flow, but kept the wand imbedded in my ass. I could feel the pressure build and the water leaking out around the wand and down my legs. I yelled, "I can't hold it anymore, pull it out, pull it out." 

Debra placed her hand on my chest and held the wand in my ass, "Now sit up a little and scoot over to the drain. When I pull the wand out clinch your ass tight and then sit right on the hole and let loose. It's fine, don't worry any mess you make we can hose down, that is what this shower was built for." 

I felt the wand pull out and I barely held the water back, as soon as my cheeks landed on the floor my bowels opened up and it felt like 10 gallons of water released out of me. Debra took another hose off the wall and sprayed me down with warm water. She lifted me up a little and washed my ass down, "Looking good, now let's do it again to finish the cleansing, then one last time to freshen up." 

I didn't know what all that meant but I couldn't wait to find out. Debra repeated the first process, and this time it felt like only water came out. Then she screwed on this jar of liquid to the wand and shoved it back up my ass, "This is the freshener, a solution of herbs and perfumes to make you smell pretty and make you feel relaxed." 

The liquid being sent through the wand this time felt thicker than water, like oil. It turned out to be perfumes and a little drug of some kind to relax me. Going through the rectum you don't need much to get into your blood stream and work its relaxing magic.

After our shower we dried off and moved toward a door in the bathroom. It turned out to be Debra's wardrobe room which was the size of an apartment. Debra grabbed my hand and looked at me, "Let's make your darkest dreams come true, anything you want to try on we will do it, ok?" With that she opened up a wardrobe to the most sexy bras, panties, slips, nylons, and garter belts of every possible material and color of the rainbow. 

Debra grabbed my hand and guided it to touch the soft silky slips, "Feels nice doesn't it? Let's see what you would look good in?" 

Debra pulled out a sexy pair of red lace panties, matching red bra, garter belt, and thigh high red nylons. She pushed me back further into the closet where there was a three sided mirror and a big, round, red, cushioned bench to sit on while getting dressed. She threw the clothes onto the bench and had me stand in the middle of the mirrors. I looked at all the mirrors and I could see my naked body, all smooth and clean. My nipples were sticking out like pert little breasts, and my pencil dick was trying to stick up like a man. 

Debra held out the bra so I could put my arms through, then she turned me around and fastened the back. She spun me around again to face her and was down on her knees lifting my foot into the garter belt, then the other foot, and up it went to my waist leaving the straps dangling at my hips waiting to be attached to the nylons. Then the lacy panties, first one foot, then the other, and up my smooth legs they went. When she pulled the panties up and over my cock I felt the lace on the cheeks of my ass. I was delirious with the erotic sensations pulsing over my body. 

Debra leaned forward and kissed my cock through the lace, "You are looking so pretty Brandy." I thought she was using 'Brandy' as being short for Brandon, like calling Robert, Bobby or John, Johnny, but now I knew she was calling me Brandy as in a girl's name, and I liked it.

Debra pushed me back to the bench and sat me down. She scrunched up one of the nylons in her hand and told me to point my toes down. She then pulled up the nylon over my foot, up my calf, and all the way to my thigh. She pulled the clasps down from the garter belt and attached them to the tops of the nylons. She did the same thing to my other leg. 

She quickly grabbed me by my hands and pulled me into her arms and kissed me. As she kissed me, her tongue went wild in my mouth. Her hands were feeling my ass through the lace, and then she would run a hand up and down my nylon covered thigh. She reached in between us and massaged my nipples through the lacy bra. My legs went weak and I almost lost my balance. 

Debra held onto me "Go with it baby, let yourself feel the new you. You are so hot and sexy." Her naked warm body pressed against me was making me light headed; part by the drug she slipped up my ass, and part was the heightened feeling of silk and lace on my body. I was Debra's new live Barbie doll. 

Debra then whisked me around the corner of the closet to a make-up table, with lights all around and a wall covered in wigs, each having its own hair style and color. Debra grabbed a brown short haired wig and pulled it over my head, with my hair so short nothing had to be hidden. She then sat me down on the make-up chair and sat right on my lap facing me. I could feel her hot pussy pressing against my cock, my lacy panties being the only thing between us. 

She kissed me again, "This is making me so fucking hot. Now let's apply a little lipstick and eye shadow." She was so quick with her strokes that in less than two minutes she was spinning the chair around and hopping off of me. I looked into the mirror and I saw a, if I do say so myself, hot babe. I couldn't believe my eyes, I was totally passable.

Debra was putting on a black corset that pushed her boobs up high and her nipples were sticking out the top. She grabbed a long, black silk robe and as she slipped it on she pointed me back into the bedroom while she finished getting dressed up. I walked into the bathroom and twirled around in front of the mirror, rubbing my hands over my bra covered titties. My little budding breast seemed to fill up the little training type bra. If I had just a little more budding it would have looked like I have real breasts. 

I bent over and ran my hands up and down my legs enjoying the soft nylons. Debra called out from the wardrobe, "We are going to have so much fun Brandy. Go lay on my bed sweetie, I'll be right there." 

I thought to myself 'This is it. I'm going to lose my virginity. I'll finally get to put my cock in a pussy.' I know she said I couldn't please her with my little boy cock, but I want to try. I want to feel what it's like to put my cock in a nice, hot, wet pussy. I walked into the bedroom, purposely wiggling my little ass in my red panties. I was really getting into the feel of my sissy outfit.

I crawled onto the king size bed which was covered in the softest silkiest white material I have ever felt. I lay down and sank deep into the comforter. I was lying on my back looking up at a, big cliché here, mirrored ceiling. My body stood out, all dressed in red, against the white bedding. I couldn't resist as I started to play with myself. Slowly I started circling my nipples with my fingertips, gently rubbing the lacy bra against my nipples. My nipples responded to my touch by growing out and hard. The scratchy lace against my nipples made them ten times more sensitive. 

I could feel a wet spot starting to form in my little red panties. I was getting into myself, starting to moan in pleasure when Debra spoke up, startling me out of my self-pleasure trance, "You keep playing with your titties like that and you're going to make a big mess in your panties." My hands darted back to my sides, and I could feel myself turn as red as my outfit, embarrassed at being caught.

Debra stood next to the bed in her black silky robe, so sexy. Debra moved onto the bed and lay next to me, "I see you like your new look, can't keep your hands off yourself you dirty little slut." as she said that she tweaked one of my nipples and made me moan and squirm under her control. 

Debra smirked at me and started to rub my nipples through my bra, "MMMM, my new little sissy slut likes her titties played with doesn't she? Listen to you purr like a little kitten." 

I was moaning and feeling so good. My body was on fire with lust, "Yes, yes please don't stop Miss Debra." 




Pool Boy Gets Dressed Up Ch. 01



"Oh baby we are going to play all day long. I am going to show you new ways to make you scream out in pleasure. Do you trust me baby? You know I won't do anything you don't want or that will hurt you don't you baby?" 

My back was arching up as waves of pleasure shot through my nipples down to my aching little cock, "God yes Miss Debra, I trust you. I want to be your little sissy slut please, oh god yes please." 

Debra was talking softly in my ear, lightly kissing me all over my neck and face, always playing with my nipples "Call me Mistress, baby that makes me so hot." 

I wanted to cry out in ecstasy, my body was writhing from side to side, "Yes Mistress."

Debra told me to put my arms over my head and to trust her. She then got on her knees and walked up to the side of my head and grabbed my left hand and pulled it towards the top of the bed, as she did this she looked at me "You trust me don't you baby? Are you ready to feel the most intense pleasure you've ever experienced?" 

"Yes Mistress I trust you, I want to make you happy." I pleaded back at her in response.

Debra reached over me and I felt the padded handcuffs tighten around my wrist. She quickly grabbed my right wrist and secured it the same way. I could move my arms a little so I wasn't being stretched out, and if I scooted up a bit more I could bend my elbows and put my hands behind my head. I knew I wasn't going anywhere, nor did I want to. 

Debra then swung her right leg over my face so that she was facing the foot of the bed. Her robe swung around me like a cape that softly landed around my head allowing a quick peak up into her pussy before I was plunged into darkness by the robe. The robe parted open a bit as Debra brought her hand to her pussy, and with the little bit of light I could see her pussy lips open up with her fingers. 

Debra lowered herself onto my face, "Eat me slut. Make your Mistress happy and lick her pussy. Show your Mistress how much you like being her sissy slut." 

My tongue darted out and searched out her warm pussy. MMMM, it was so good, she smelled so sweet, and her pussy was so wet and hot. She must have had on a G string, or something, because I kept feeling the strap rub against my face as I ate her pussy. Debra rocked up and down on my face and I eagerly ate, licked, and sucked her pussy until finally I was rewarded by her orgasm as it flooded into my mouth. I loved eating her pussy and drinking her pussy juices.

Debra lifted off of me, spun back around, and started to clean my face of any juice that I missed, "Mmmm, that was so fucking awesome. You eat my pussy better than any man or woman I've been with." 

I felt a huge sense of pride and was really turned on to the fact that she has been with men and women, "Thank you Mistress, I love eating your pussy and drinking your sweet pussy juice." 

Debra placed her hand on my cheek, "You make such a pretty sissy slut. My turn to make one of your dreams come true baby, tell your Mistress what makes you happy, hmmm?"

To be continued.....



Pool Boy Gets Dressed Up Ch. 02



I would like to thank the readers for the great feedback. I hope to continue this storyline to your liking. Feel free to offer suggestions. The feedback helps. 

*

Yesterday I was a shy, young, teenage pool boy minding his own business. Today I am dressed as a sissy slut and just finished eating my Mistress' pussy. My arms are handcuffed over my head and attached to a four poster bed.

Debra knows how to get me to spill my guts. She gets me to confess my deepest desires, even before I could figure out what they are. Debra has such a sexy and sultry voice that, just by listening to her, she can make you cum.

Debra placed her hand on my cheek, "You make such a pretty sissy slut. My turn to make one of your dreams come true baby, tell your Mistress what makes you happy, hmmm?"

I was squirming under her touch, what did she want me to confess? I blurted out one of my desires, "I'm a virgin, I want to fuck you. I want to feel my cock inside you, please Mistress?" I begged.

Debra placed her finger across my lips, "Shhhh, I said your DEEPEST desires. Besides that little cock isn't long enough to get inside my pussy, baby. No, you want your Mistress to make you really feel like the little slut you want to be, I can feel it." 

As she said this she put her finger in my mouth and swirled it around on my tongue, getting it really wet. Debra bent down and started to suck my nipple through the lacy bra. At the same time I felt her wet finger probing my virgin hole. I didn't resist the penetration as I pushed back against her finger. Yes, she did know my deepest desires. I let out a deep moan as the tip of her finger entered my dark hole. "Ugh, mmmmm. Oh god YES!"

Debra released her hold on my tit, "I knew you wanted this. You need to be the fuckie, not the fucker. I know the feeling baby, let me in. I will make you feel so good. I will give you an orgasm like no other. Tell me Brandy, tell me you want this; tell me you want to be fucked." Debra's finger was slowly massaging the inside of my ass. I couldn't believe how sensitive and intense the pleasure was. 

I did want more. I know I want more, and she knows it as well. "Yes! Oh Yes! Mistress please, please, fuck me. I want to be fucked. Make me cum hard Mistress."

Debra gave a low guttural laugh as she pulled her finger out of my ass. She sat up over me again and pulled off her black robe, exposing her beautiful tits, which were sticking out the top of her corset. Springing up from her crotch was a life like strapon cock. Debra grabbed hold of her cock and stroked it like the real thing. "Mistress Debra is going to fuck you Brandy. I am going to take my cock and fuck your tight little pussy. I know you will enjoy this. I will make you have the most intense orgasm of your life. You want this don't you baby? Tell me to fuck you with my cock."

My hands were cuffed over my head. I was staring up into a beautiful woman stroking a big cock, waiting for my permission to stick that big cock up my tight little virgin hole. A million things were going through my head all at once, could something that big fit? Will it hurt? What if I tell her no, will she stop and release me? Trust her, focus on trusting her I thought to myself, "Mistress Debra I want your cock in me. Fuck me with your big cock please. I want to be your sissy slut, I want to be fucked."

It was over; all my inhibitions have been released. I was dressed up like a sissy slut and begging to be fucked. I felt relieved, it was my true desire. I wanted to be taken, controlled. My body spoke volumes when my cock never really matured to a man's size. My breasts formed more as a girls would, budding and puffy, rather than a firm chest of a boy. I couldn't even grow hair on my body like a man. I now know that I want to be taken by a cock.

Debra moved forward along my torso, dragging her wet pussy up my stomach until the tip of her cock touched my lips. "Good girl, let it all out and Mistress Debra will make it all come true. Now you need to learn to suck a cock and get it nice and hard before you can get fucked by it. Take your tongue and run it over the smooth head of my cock."

I looked up, in between Debra's tits, into her lustful eyes as my tongue stretched out of my mouth searching for my first cock. I ran my tongue over the plastic phallus. It looked like a real cock, nice flaring head, long veiny shaft that was about six or seven inches long, and resting against a black studded leather harness that Debra had securely fastened around her waist.

"Ya. That's it, run your tongue all over my head, get it nice and wet. Open your mouth baby and feel and taste my cock." I opened my mouth and Debra pushed about three inches into my mouth. She pulled it out, and then pushed it back in several times, mouth fucking me.

"That's a good slut, get it wet. Let's see how much you can take." With that she started pushing her cock farther down my throat. Each stroke went down a bit more each time. I could feel my eyes begin to water as I started choking for air.

"Breathe baby. When I pull my cock out of your mouth take a breath. Relax your throat, let my cock slide down. We will work on your gag reflex. That's better. You are taking six inches of cock in your mouth. You're such a cock slut. Your little pussy is probably hot and ready to be fucked." I looked up and over the cock in my mouth as nodded to her. I was quite proud of being such a good cocksucker my first time.

I couldn't believe I was sucking a cock, though a plastic one. The size of Debra's cock was so different compared to my little pecker. I now understand how pathetic my cock really is, it couldn't possibly satisfy anyone. You need a real man sized cock, like the one filling my mouth.

Debra pulled out her cock, "That was a good first cock sucking lesson. You need to make your man happy so he fucks you really good. And you are going to do just fine." 

Debra slipped her cock out of my mouth and moved back down over my body, dragging her cock down my torso. I felt the heat of her pussy when she reached my cock. She started to grind her pussy against my cock. I lifted my hips up in attempt to feel the heat of her pussy and stroke my little cock. 

Debra looked at me, "I know that little thing is somewhere in your panties." She laughed as she ground back against my pelvis. 

Debra moved down my legs, grabbed hold of my panties, just like she did with my speedo earlier, and then she pulled them down and off in one quick motion. She then grabbed my legs, lifted them over her shoulders, and dove into my hot little hole. I felt her tongue penetrate me. It was so hot and wet I wanted to scream out in pleasure. She kept at it, tongue fucking me, getting me really wet. My puny little cock was staring down at me with a big drop of cum ready to fall. 

Debra rocked my ass forward, forcing my cock to be just inches from my mouth. The drop of cum dripped off the tip of my cock and I opened my mouth just in time for it to land on my tongue. Fresh from the tap always tastes the best. Debra then pushed two fingers in my ass. "Oh, yes, yes, that feels so good Mistress." I whined.

"That's it baby take it, open that tight little hole for your Mistress. You're getting nice and loose, almost ready." Debra poured some liquid on my ass and her fingers continued to slip in and out of my ass with no pain at all.

Debra lowered my legs as she moved up to lay her body on top of mine. Our cocks pressed into each other. Her cock was so much bigger than mine. Debra kissed me on the lips as she moved to my right ear. Debra lightly bit my earlobe and darted her tongue around the edge, "Are you ready baby; ready to get the best fucking of your life? Let me hear you say it? Tell me how much you want my cock inside you. Tell me your all mine; you are my fucking little cock sucking slut!" Debra continued to grind our cocks together as she taunted me into confession.

I raised my legs up and wrapped them around Debra's waist. Her cock slid down and pressed against my virgin hole. I looked at Debra, and with a panted breath, "Yes Mistress, I am yours. Fuck your little cock sucking slut. Show me how to take a real cock." 

I felt the head of Debra's cock push gently into my ass. This was so much bigger than her fingers. It felt like a baseball bat was trying to push its way in. "Remember baby; push out when I push in. Let me fuck you with my cock baby." Just as she instructed me I felt the firm pressure of her cock slipping into me. I pushed out against the intrusion. The pain shot through me and Debra bit down on my ear sending another sensation through my body.

"Take it slut, feel my cock enter you. Relax, and enjoy being fucked by a cock. You want this, you watched movies of boys taking a cock, and you know you want it." Debra urged me on as she pushed more and more of her cock deep inside me.

I felt Debra's weight resting on my legs and knew she was all the way in. I felt so full and so stretched. The pain was subsiding. I wiggled my ass a bit to allow my pussy lips to wrap around her cock. "Ya, that's it slut wiggle that hot little ass of yours. You control the feeling. Grind that slutty pussy of yours against my cock. Tell me when you're ready to be fucked."

I pushed back against Debra's cock. I moved my hips back and forth, feeling the big head press against my insides. My ass was on fire, not in pain, but in sheer pleasure. This is what I was built for, to be fucked by a big cock. The feelings were over whelming, I wanted to be fucked so badly. "Yes Mistress, please fuck me. Fuck me hard. Please fuck me I need your cock."

"That's the little slut I knew was in there waiting to come out." With that Debra pulled her cock out, just until the head held my ass open, then she slowly pushed every inch of her cock back into my ass. Slowly she fucked me letting me feel her cock glide in and out; breaking my pussy in slowly so that I could take and want more.

"I can't take it anymore, please Mistress fuck me harder. I want to be fucked hard." Debra pulled her cock all the way and then slammed her cock all the way back in until her pelvis slammed hard against my thighs. "Yes, that's it, yes, fuck your little slut Mistress, fuck her good."

Debra started to slam her cock in me harder and harder. She was relentless. The sweat began to drip off of her forehead as she continued to plunge into my hole. "Take it bitch. You want a cock in you; well here is what it feels like. You like cock don't you baby? You want a real man to fuck you now, huh slut? You need more cock. I bet you want to suck a real cock now, don't you?" 

My head slapped back and forth against the pillows. I bucked up to meet every thrust Debra gave me. My little cock was soft and flopping all around, spewing strings of pre cum all over my stomach. "Look at you leaking cum all over. I bet you're thinking of sucking cock aren't you slut? Dreaming of having a big man take you and treat you like his little slut? Ya, you want a man to shoot his hot cum in your mouth and fill your little pussy with his juices."

We both couldn't hold back any longer. Debra screamed out first, "Oh god, yes I'm cumming. AAHHH!!" When Debra started her orgasm by ass actually had an orgasm. Not my cock, but I felt my ass actually spasm. Cum seeped out of my cock and onto my chest and stomach. My cock was soft and not giving me the pleasure that I was feeling deep in my bowels.

"I'm having an orgasm in my pussy. AHHHH!! YES! I want a real cock Mistress. I want to feel a man cumming inside. I want to suck his juice from his cock. OHHHH! My...god.." My body shook uncontrollably until Debra finally fell on top of me in a pile of sweat and cum. She grabbed my face and we kissed until our bodies calmed down.

"Holy shit that was wild and hot." Debra stated as she gently pulled her cock out of my ass. She then jumped off the bed, stepped over to the nightstand, and pulled out a bottle of cream.

As she spread the cool cream on my gaping hole she said, "This will help get you back to normal and keep you from burning. Was that the best orgasm ever?"

"Oh yes Mistress, you are so right, I am a cock slut. Thank you for opening me up and making me confess my desires." Debra came around to the top of the bed and kissed me on the lips as she unlocked the hand cuffs.

We went back into the shower and cleaned up. When we were done I asked Debra, "I hope I could still be your pool boy?"

Debra embraced me, "Of course silly. You think that this changes anything? No sweetheart I want you around for a long time. Don is gone, again, for the rest of the week. Finish your job as fast as you can and come over so we can play some more. I have a lot more to teach you." With that she kissed me on the head and walked back to the pool where I left my stupid boy clothes.

I finished my six hour a day job in half the time. I was at Debra's house by noon each day. Debra taught me how to deep throat her seven inch dildo without gagging. I was accustomed to being fucked, and wanted more each time. My oral skills on Debra's pussy seemed to be pretty good by the sounds of her orgasm. But the week came to an end and Don would be back from his business trip. 

Debra sensed my melancholy mood on our last day together. We lay in bed spooning, with Debra behind me firmly embedded in my ass. I was slowly grinding my ass back against her cock trying to enjoy every last second I could. "What's that matter baby?" Debra whispered in my ear.

"Our week is over, Don will be back tomorrow and I won't be able to come and play. I don't want to think about not getting fucked, eating your pussy, or being able to dress up." I was almost in tears.

"Is that all that's bothering you. No worries my little slut." As she said this she tweaked my nipples and shoved her cock deeper in my ass, causing me to just about have another orgasm.

"Don comes and goes all the time. He will be here for a couple of days, and then off he goes again for days at a time. You just give me a call on the days you aren't cleaning our pool and I will let you know if you can come over. I want you just as much as you want me. I love fucking my little tranny slut."

The following week I stopped by Debra and Don's place to do my routine pool check. Debra was home walking around in absolutely nothing. "I was expecting you today Brandy. Don is not here so I thought you can hurry with the pool chores and scurry your tight little ass up to my bathroom and get ready for some play time."

I was elated, "Yes Mistress. Thank you. I will be done here in no time." I quickly cleaned the pool and tested the chemical balance. Within the hour I was scurrying up the stairs, pulling my shirt and shorts off as I fumbled my way to the bathroom. Debra was on the phone, talking, and walking around the bedroom when I cleared the door. She was wearing a see through negligée that in no-way was designed to conceal anything. Debra waved me through to the bathroom, and held her hand over the receiver as she told me to go ahead and get started in the shower without her.

I knew the routine as I gave myself an enema and ran the shaver over my body to remove any possible stubble. I finished my shower and was rinsing the last of the perfumed soap off my body when Debra popped her head in the shower, "Almost done sweetie? I'm dying to show you a couple of new tricks, and I bought a new toy." Debra gave me a wicked wink as she left the shower.

I was so excited that my limp little dick started to drip cum already. I quickly got out of the shower and dried off. I met up with Debra in the wardrobe ready for my transformation to Brandy. I liked being Brandy more than Brandon. Brandy wore sexy clothes that felt great on my body and gave me confidence. Brandy was more submissive but a sexual slut at the same time. Brandon was an insecure introvert that had no sex or friends.

Today I donned a sexy red wig that flowed down past my shoulders. Even the hair cascading over my shoulders was turning me on. I was getting pretty good at applying my own makeup by now, but Debra still left the final touches for her to do. Debra handed me a white corset to put on. I stepped into the corset and Debra cinched it up in the back. It was so tight I could barely breathe, but turning around to the mirror, by breasts actually looked full and stood out like real tits. I lifted my hands to my breasts and gave them a squeeze. I couldn't believe how good they looked.

Debra hugged me from behind and put her hands over mine as she whispered in my ear, "You look absolutely beautiful. Except for that little thing hanging between your legs, these tits make you totally passable as a sexy, hot, pretty little girl." Debra squeezed my breasts and kissed me on the cheek.

I thought 'A pretty little girl' yes, that is what makes me feel good. I looked at myself in the mirror, my hair and makeup were perfect; soft face with no stubble what so ever; even my Adams apple was barely noticeable. The corset showed off my perky little breasts and curvy body, and my swimmers legs showed smooth and tone. I was pretty hot, except for that puny little cock sticking out between my legs. At least it is so small that it hides well in the sheerest of panties. My boy pussy is as sensitive as any real pussy, at least for me. I love the orgasms that come from being fucked by Mistress Debra; they are intense and earth shaking.

Debra pushed me out of the wardrobe, "That's all we are wearing today, now go on and wait for me on the bed, I will be right along." With that she gave my bare ass a nice slap as I shimmied out the door.

I lay on the bed looking up at the mirrors, admiring myself, when Debra walked into the room wearing a new strapon, and nothing else. This cock was at least nine inches long and three inches wide. It looked so real, right down to the balls that seemed to actually have movement. Debra grabbed her cock and pointed it at me, "Do you like my new cock? It finally arrived yesterday and I have been dying to have you over ever since. Don left this morning for a trip and the only thing I could think about was fucking you with this baby. It has a soft latex coating that feels so real, my balls are actually soft and they hang just the like real thing." As she said this she cradled her balls in her hand as if weighing them.

Debra walked over to the bed and stood at the end, "Come here slut, suck my cock and get me ready to fuck your pussy." My mouth was watering and my ass was twitching with excitement. I wanted this cock real bad. I crawled on all fours, towards Debra, like a lioness to its prey. My mouth was, watering, anticipating the feel of that cock sliding down my throat.

I took a hold of her cock, feeling the weight and girth of this monster. My eyes were transfixed on it as I felt it up and down the shaft. It actually had pliable skin that moved when I jacked it up and down. In a daze I spoke more to myself than to Debra, "It's so life like, it feels just like a real cock." 

I moved my hand down to the balls, and rolled them around my hand. This was the closest thing to a real cock I could have ever imagined. It was a thousand times better than my little nub. I could see why Debra, or any woman, could never be pleased by my pathetic dick, when there are cocks like this out there. It felt so natural to be holding a cock in my hand.

I leaned over and rubbed the soft head over my face. I slowly ran my tongue over the head and shaft. I wasn't even thinking about Debra, I was just making love to this cock. I was in another world, just me and this cock. I had been practicing cock sucking on a smaller dildo, but this was different. I opened my mouth and moved my head over the cock. I swallowed about four inches as I felt the head pushing at the back of my throat. I moved my tongue along the shaft as I felt the skin move back and forth. It wasn't solid and stiff like the other dildos.




Pool Boy Gets Dressed Up Ch. 02



Debra was rubbing my head, watching me; coaxing me to make love to her cock, "OOHH Ya, that's it enjoy the feel of my cock. That's it take it in slowly. Run your tongue over every inch of my cock. You look so hot sucking my cock. You really do love cock don't you baby? You are my sweet little tranny pussy slut aren't you baby? This cock was made special; it is a replica of Don's cock." 

Debra's voice can always make me drip. I was so into sucking this cock, Don's cock, that when she started to call me names it sent me over the top. "OH god I'm going to cum." Debra grabbed me by the arms and lifted me into her, hugging me tight. My little cock pressed into her big massive man cock as I shot my load all over her cock and between our stomachs.

Debra gently guided me back to the bed, joining me at the same time. We lay on our backs staring up into the mirrors. Debra turned to me, "You made such a mess. Look at my cock dripping with cum. All good sluts clean their mess, now get down there and suck my cock clean."

I didn't have to be told twice, I didn't even have to be told once, I couldn't wait to lick my cum off her cock. Now it really was like sucking a man's cock. Would Don's cock feel just as good? I wonder what Don's cum tasted like? I was sucking a cock covered in cum. I was such a slut, and I was never happier. "Ya baby, lick that cum up, clean my cock you slut. Get me nice and ready to fuck you good and hard. You like having a cock in your tight little pussy? Well, today I am going to really break that pussy in. I am going to fuck you so hard and deep you'll be cumming until next week." 

I was humming on her cock with anticipation. My ass was up in the air wiggling, waiting to be fucked. "Look at you, you slut. You can't wait to get fucked can you? You want my cock deep inside?" Debra pushed me off her cock and flipped me over onto my stomach. Debra crawled between my legs, grabbed hold of my hips, and pulled my ass up into the air as my head fell down onto the bed. I felt the cool lube being applied to my tight hole. I pushed back against her finger. I needed to feel something in me now I was so fucking horny.

"Slow down you horny little cunt. Look at you; you can't wait to get fucked. I have created an insatiable little whore." With that Debra pressed the head of her cock to my entrance. I let loose a big sigh of pleasure waiting for my big cock, for Don's cock, "MMMMM, oh yes fuck me Mistress."

Debra held my hips tight as she guided her cock to my hole. The head was much bigger than anything I have had, but I was determined to have that cock in me. I took a deep breath and then let it out bearing down on that cock head as it pushed into me. The cockhead slipped into my ass sending a sharp pain throughout my body. It was the best pain I have ever felt. I couldn't wait for Debra to feed me more cock, so I pushed back hard swallowing half its length with my pussy. "OOOHHHH!!! MMMMM, that is so big. Fuck me Mistress. Fuck me good and hard. Fuck me with Don's cock."

Debra took me for my word and slammed all nine inches deep inside. The latex balls literally slapped against my little peas hanging between my legs. The feeling was exquisite. I didn't think having your balls slapped could be such an added turn on. Debra pulled out eight of the nine inches from my ass. I thought my insides were being sucked out of me, then all at once everything was forced back in as Debra rammed all nine inches back into me. "Yes. Oh my god, yes. Fuck me hard, it feels so good, don't stop." I was in tears, the feeling was wonderful.

Debra started fucking me with long steady strokes that never let up. All of those laps in the pool were paying off with her endurance. "Is this what my slut likes? You like the feel of Don's cock fucking you? I bet you want Don to fuck you don't you slut? You want to feel a man fucking you now don't you? Ya, you're ready to fuck real men, suck their cocks, and drink their cum?"

Debra sent us both over the edge as she grabbed my hips and held me tight to her, fully impaled on Don's cock as her body convulsed in a massive orgasm. The pressure from inside set my orgasm off as well as the insides of my pussy was filled to the brim with Don's cock. By cock started to spew wads of cum all over the bed linens. I wished Don's cock was in my pussy filling me with his hot cum.

Debra pulled her cock out of my ass and gave me a hard slap. "You made such a mess, lick that cum off my bed. Then we need to strip the bedding off and send it out before your cum stains it." I quickly lapped up my cum, but I could see that it was already absorbing into the linen.

We gathered the linens and brought them down to the laundry room. "I will have those sent out for cleaning before Don comes home. I have a new set I wanted to bring out anyway, the change will be good." 

We went back upstairs, made the bed with the new bedroom set, and cleaned up. Rather than go back and put my boy clothes back on, Debra escorted me back to the wardrobe room. "We have all day, let's get dressed up and go out."

"Out? Dressed up?" I felt the blood drain from my face. Debra looked at me and laughed at what must have been the most shocked look she had ever seen.

"You are so funny. Brandy, when you are dressed up I guarantee you are one hundred percent passable. I bet Don could walk in the door and would not figure out who you are." Hearing Don's name made my face flush. Only moment ago I was begging to be fucked by Don, Debra's husband.

Debra could see me flush red as I looked down with embarrassment. She consoled me out of my funk, "Oh Brandy you are so cute when you blush. Don is one good looking man; I can't blame you wanting him. His cock does feel good buried deep inside doesn't it sweetie?" Debra lifted my chin so that I could look her in the eye. "Don't you worry; Don and I have a very strong relationship. It is so strong that if he wanted to fuck you I would let him in a heartbeat. Of course I would have to be there as well. I wouldn't want to let those oral skills go to waste while you are getting fucked."

My eyes opened wide; did she just offer her husband to fuck me? Can I really make love to a man? Don and Debra are the perfect couple. I think I was falling in love with Debra and in lust, at least for now, with Don. "Let's get dressed Brandy and go have an early dinner. I will take us to a place out of the area where no one will know you." 

I nodded to her, still in shock about going out in public and dreaming of Don's naked body.

I was still skeptic, but allowed Debra to prepare me for my first outing.

To Be Continued... 



Pool Boy Gets Dressed Up Ch. 03



Debra and I just finished some of the best sex ever. Debra had a lifelike replica of her husband's nine inch cock made, strapped it on, and fucked me silly with it. But now Debra wanted me to go out in public dressed up as Brandy. I wasn't sure about this, but looking in the mirror I did seem passable.

We reapplied my makeup and Debra picked out a nice soft brown wig that fell past my shoulders. Debra handed me a wrapped box, "Open it. It's just a little something for our special day." I opened the box and began to cry. It was a complete outfit just for me.

I pulled out the pieces one by one and held them up to me as I spun around in the three way mirror. Debra bought me a pretty light pink flowered print top, a short white straight line skirt, a white pair of tights, and a pair of black flats. "Now don't go smearing your makeup on your new clothes. I also bought you a bra with forms to give you those titties you so want and a nice pair of silky tight panties to hold back the pee wee cock of yours." I looked at Debra with more love than I have ever shown anyone in my life.

"Ok, now let's get dressed and go have a bite to eat." Debra turned and put on a similar outfit, with a red low cut blouse, a jean skirt, no bra, no panties, and a pair of "fuck me" pumps, she was hot.

"I bought you flats; didn't think you were quite ready for heels your first time out." Let's go sweetie I'm starving after that workout. I quickly slipped on my flats and jumped up to catch up with Debra.

We drove for forty-five minutes before we came to a nice mall. This mall had only high-end stores. I never have been here before but it was obvious that Debra knew her way around. She parked her Mercedes SL in a nice shaded spot and hopped out of the car. I hesitated, still not sure if I was ready. "Come on Brandy I'm starving."

I opened the car door and swung my legs out of the car, here goes nothing, "I'm coming Miss Debra."

"Out in public, Brandy, you need to just call me Debra. Remember, we are just a couple of hot chicks going out for a bite to eat, and do some shopping of course." Debra grabbed my hand and we walked through the parking lot and into the doors of the mall.

People were all over the place, and not one person stared at me. I felt my confidence building up as we strolled through the mall. We finally arrived at our destination, a sushi restaurant, my favorite. Debra ordered our meal. We ate as we watched people walk by the window. We finished our meal, Debra paid our waiter, and we left with no scene made. I now felt I was walking with me head held high.

Instead of going back to the car, Debra pulled my hand guiding me into the mall, "We have some shopping to do." Our first stop was Bloomingdales. Debra went to the young miss section and started pulling things off the rack and placing them in my arms. "Go try those on." She instructed.

I put my face close to her ear, "Debra, I can't afford this, and what if I get caught in the ladies dressing room?"

Debra looked at me with that stern look, "When Debra takes you shopping, Don pays, remember that. Besides nobody can see you in the dressing room, that's why they have doors. Now get your tight little slutty ass in there and try these on. I want you to model each one. I will be over here on the couch waiting."

I tried on, what seemed like a hundred outfits. When I was finished Debra grabbed several of them and threw her charge card at the lady, "Be a dear and have those wrapped up and sent to my house."

The total came to almost three thousand dollars. The sales lady smiled at us as she told Debra, "I will have them sent over in the morning if that is alright with you?"

Debra responded, "That will work out just fine, thank you." 

Debra turned to me, "Come on Brandy, time for some bras to hold those little titties up." Debra poked my left tit and laughed as we headed to our next store.

We went to a lingerie store and bought panties, bras, and nylons. Then Debra threw in a few naughty outfits as well. Then off we went to a shoe store, where we purchased my first pair of heels. Being that I am so short any heel height would be fine. Debra picked out a four inch, open toe, sling back, with a stiletto heel. It took some doing standing up, but the salesman was very helpful and flirted with me as I fell into him trying to stand up. "Watch out there miss, you can really twist an ankle." He was very good looking and I swear his hand was on my ass longer than necessary as he righted me back up. I blushed at his remark.

Debra again threw the salesman her card and had everything sent to her home. I was exhausted, we shopped for four hours. Debra drove us home and had me call my parents to let them know I was spending the night at a friend's house and would be back the next day. No problem there, it was Saturday and my parents usually are off doing something anyway.

Debra and I kicked off our shoes as we walked into the house. We were walking arm in arm laughing about the salesman making a pass at me when we entered Debra's living room to find Don standing there holding a drink in his hand. Debra and I both stopped in our tracks. Without skipping a beat Debra changed the flow of the conversation, "Darling, you're home early, what a pleasant surprise." She went up to him and gave him a long tonsil washing kiss.

"I'll come home more often if two lovely ladies such as your selves were here to greet me like that. Honey, who's your pretty little friend?" Don was so suave and good looking. He had on a nice yellow polo shirt with perfectly creased black slacks. What was really attractive was the fact that he had no shoes or socks on and his feet were absolutely stunning. He had large feet, with perfectly manicured long slender toes. His feet had the same even olive complexion as the rest of his body. I stood there fantasizing about sucking on his toes.

"Brandy Sweetheart!" Debra was all but shouting at me, breaking me out of my trance. "Brandy come here and let me introduce you to my husband Don." I shyly took a step towards them.

Don reached out his hand, I thought to shake my hand, but as I extended my hand he grabbed it softly into his, turned it palm down and kissed the back of my hand. My knees went weak and I almost passed out. I could feel Don grasp my hand hard to hold my balance. "Are you ok dear? You feel like you were going to pass out."

"Oh I am sure she is fine. Brandy is Cheryl's niece from next door. Brandy came to visit but Cheryl had to leave and meet Tom to sign some papers. You know Tom, when he wants something he has to have it now. Cheryl will be back on Sunday and I told her I would be glad to entertain Brandy while she was gone. We have had a great time so far don't you think Brandy?" 

I looked up at Debra, we never worked with my voice but I managed to say, "The best time ever." and ended that with a smile.

Don released my hand, but not before giving it a tender squeeze, then walked across the carpeted floor towards the bar, "I'm fixing drinks to toast our guest for the evening, that is if Brandy is old enough to drink."

Debra fell onto the couch, "I'll have a martini darling, and Brandy is old enough to have a rum and coke, if you don't call the police on her." Debra laughed off the inside joke, knowing the last time I drank rum and coke with her we ended up fucking each other.

Don, being the ever delightful and handsome bartender responded, "One Martini for My lady, and one Rum and Coke for the young lady. We are in for the night so no need for the cops." We all laughed. 

I was still worried how this was going to play off. I was stuck here now since Debra told Don I was the next door neighbors visiting niece and had to now spend the night. I guess staying in such a nice house wouldn't be all bad, but in the morning Brandon is going to make an appearance unless Debra can sneak away and bring me a different set of clothes.

Don brought us our drinks and placed them on coasters on the table in front of us. Debra was lounging on the couch and I was still awkwardly standing. I guess Debra wanted to see how Don and I would interact before she finally saved me from pure embarrassment. "Come sit by me dear. Don loves his big overstuffed chair when he comes home to relax. Don, my love, what brought you home on this beautiful night?"

Don walked around his chair, with his refreshed drink, and sat down. As Don sat down he crossed his left foot over his right knee and was lightly massaging his toes with one hand as he took a sip of his drink. "I finished business early and rather than spend another night away I grabbed a flight and here I am. I thought coming home to a nice drink and a relaxing night in the spa would do me wonders." 

My eyes were glued to his hand running up and down the soles of his feet. I never gave feet any thought before, but somehow, Don rubbing his feet was turning me on. I wanted to sit in front of him, massage his feet, and suck his toes. What was I thinking?

I looked up at Don's face as he smiled at me. He was watching me stare at his foot, as my face blushed a deep shade of red. Don put his foot back down on the floor, placed his drink on the table next to his chair, reached his arms over his head, and stretched his body out. As he stretched, he pointed both of his feet, clearly displaying them for my pleasure. Don's shirt lifted out of the top of his pants exposing his soft olive skinned stomach. Don then got up and announced, "I'm going to change and take that nice soak in the spa. Anybody care to join me?"

I figured this would be a good time for me and Debra to work a plan. I was mistaken as Debra chimed in, "That sounds like a wonderful idea. Brandy and I shopped for hours. My feet are killing me; they could use a good soak and a good massage. You go ahead dear while I find Brandy something to wear so she could join us as well."

Don started up the stairs that led to his bed. I wanted to race after him and watch him change, but I knew I had to keep my feelings in check. Debra touched my should, "Brandy are you ok? Your mind seems to keep wondering and you're tuning us out. Now let's go see if we can find you a suit." 

I looked at Debra, "How are we going to do that? The water might wash my makeup off, or what if my wig falls off, or worse, what if I get a hardon and Don notices?"

Debra laughed again at me, "You worry too much. Your makeup will be fine. We will apply a little adhesive to your short hair so that the wig stays on, it's not like you're going under the water and sucking his cock you know. And as far as that little thing you call a cock gets hard, well the Hubble Telescope couldn't see that." Debra laughed as she spanked my ass all the way up the stairs.

Instead of heading to her bedroom, which I was disappointed thinking I might catch a glimpse of Don naked, we turned down the hall the other way and headed towards one of the spare bedrooms. As soon as we entered the bedroom and Debra closed the door she spun me around and into her arms. Debra took me by the waist and pulled me in for a long kiss, "That was so hot. Don didn't know it was you. We can really pull this off. I will have the lights really low for a relaxing ambiance. We will put you in a nice little one piece suit. I have all sizes here for guests, I'm sure we can find you something. We will tuck that little pecker under your balls and shove it up your ass if we have to."

Debra was talking a mile a minute and all the while her hands were rummaging through the dresser drawers searching out a suit for me to wear. Debra finally came across a nice dark blue one piece bathing suit that she tossed in my direction, "Try this one on, I think we can show off that figure without exposing too much. We will enjoy the warm water and soak our feet. I am sure Don will have a couple more drinks to relax him; mixed in with the hot water and him being so tired he will be back upstairs passed out on the bed. You can sleep in this room. I will come down here and fuck while Don is down the hall. What a turn on." Debra gave me a nice kiss on the lips.

I could not figure out how I was going to get out of this without just running out the door and going home never to look back. My heart just could not fathom that. As it was, since I saw Don, my heart hadn't stopped running a mile a minute. I pulled off my clothes and let Debra apply the adhesive to my head while I pulled up the suit. It was form fitting, and after tucking my cock down and under you couldn't even see it. The suit was cut high on the waist showing off my nice legs. The sides were open, but the front was covering my muscled stomach. My nipples poked out against the material and with my wig and makeup I was sure Don couldn't tell that I was Brandon.

Debra left the room to change and told me to wait for her to come get me. It seemed like only a couple of minutes before the door flung open and Debra was running in, grabbing me by the hand, and leading me down the stairs, "Quick, Don is shaving before he comes down, that will give us enough time to jump in the water and hide under the bubbles." I thought to myself, finally, a break in this big mess.

Debra and I scurried down the stairs and out to the backyard. The spa was next to the outside bar and was already bubbling and steaming. Debra handed me some candles and a lighter, "Here light these and place them around the spa." She instructed as she ran around turning off the lights. The candles illuminated just enough to see as the twilight ours receded and darkness took over.

I slipped into the warm water as I waited for Debra and Don to join me. I was nervous as hell, that goodness I could hide my shaking hands under the water. I lay my head back against one of the pillows when I looked up to see the Greek god heading my way. 

Don came down the stairs and headed for the door, leading out to the backyard. His tall body was a vision. His black hair was pulled back away from his face. His green eyes sparkled as his long dark eyelashes fluttered at me. When we locked eyes he flashed me the most perfect set of white teeth. His long bronze torso was lightly covered in a thick black coat of fur. His nipples were flat with the smallest nub in the center. His legs were long and sleek, with his flexing thighs and gams clearly outlined as he took each step. His red speedo was unable to hide the defined monster serpent that lay dormant and coiled ready to spring out and strike.

And those feet, just a small tuft of hair on the top of each foot, yet each long luscious toe was void of any hair. I stared at his foot as Don dipped it into the water to test the temperature. I watched as Don's toe flicked up at me spraying my face with a couple of drops of water. I looked up at Don, who was now looking down at me and laughing. Don turned and, to my disappointment, walked over to the edge of the pool and dove right in.

Debra came over with a picture and glasses of margaritas on a tray. She placed the tray on the edge of the spa and slid under the warm blanket of water next to me. "MMMMM, that feels so good. My feet were dying to get out of those shoes and this is the perfect end to a perfect day." Debra looked over at me and smiled, "Well, almost the end," as she reached over and tweaked my nipple and shot me a wink.

Don pulled himself out of the water and walked towards us. His now dripping wet red suit clung to his cock outlining the shaft and head perfectly. His balls were separated on either side of his shaft. Don slipped into the water across from me and Debra. "Oh that feels so good after a long week." 

Don stretched his right foot out towards Debra, who in turned took a hold of it and began to grind her thumbs into the soles of his feet, "There, darling, does that feel good?"

Don responded with a deep moan as his left foot drifted gently across my foot, "MMMMM, that is so nice baby."

Then out of the blue Debra jerked Don's foot back causing Don to slip off the edge of his seat sending him under the water. As Don's face submerged under the bubbling water, his left foot flew out of the water and right for my face. My reflexes kicked in and I managed to dodge the flight of his foot as my hands flew up, grabbing his foot with my left hand and using my right hand to grab him by the calf. I was able to stop his momentum from continuing and began to push back against the bottom of his foot.

Debra was laughing hard and also pushing against the bottom of his other foot allowing Don's head to rise back out of the water. This all happened within seconds, but it still had the surprise effect on Don. When Don's head reappeared out of the water it was followed by a stream of squirting water from his mouth, directed at Debra and soaking her face.

Debra stopped laughing as she ran her hand over her face clearing the stream of water. I sat staring at the two of them laughing before I felt comfortable with joining in. We all continued to laugh, yet neither Debra nor I let go of Don's feet. Don looked at the two of us, "I am glad you both got a good laugh at my expense. As punishment you both have to massage my feet."

I was elated with Don's command, and started to knead the bottom of his foot. I was touching his foot; it felt so strong and manly to my touch. I didn't even notice that my other hand was bracing his calf and gently squeezing it making him think I was massaging that as well. His leg was bobbing just at the top of the water and every once in a while his torso would lift up to the water exposing his hardening cock as it floated at the surface.

Don must have been balancing on his hands in order to keep his head above water. He kept his eyes closed as I continued my massage. Debra was watching how entranced I was becoming with Don's foot before she stopped the action. "Oh Brandy he didn't mean for you to have to rub his feet, he was just joking. Now you stop it Don. Brandy is our guest and YOU should be the host and rubbing her feet."

Don gently pulled his foot from me as he sat upright. Don then dipped his hands under the water and I felt him grab my foot and pull it up into his lap. Don began to massage the top of my foot along the toes causing me to take in a deep sigh and let out a low moan, "mmmm."

My little pecker was straining in my suit. If we had to get up out of the water now my cover would for sure be blown. Don lightly stroked my leg as he pressed his thumb into the bottom of my foot. My little cock leaped against the lining of my suit as Don continued the pressure on my foot. I was about to cum from his touch and tried to pull my foot from his hands. Debra quickly calmed me down, "Relax Brandy, Don knows all the pressure points on your foot. He can make all the pain leave your body. He truly has magical fingers." Then she turned to Don, "Now stop trying to give the poor girl an orgasm. I am on to your tricks."

Don released the pressure on my foot just enough to stop my pending orgasm, but not enough to stop the erotic pulsing going on throughout my body. Like a scolded child Don played it off, "Whatever do you mean darling? I'm just being the good Host you so painfully pointed out to our guest." Don turned to me, "Brandy do you want me to stop being the gracious Host and let your foot go?"

I all but screamed at him, "NO, please don't stop."

Don looked at Debra, "See, our guest does not want me to stop massaging her foot."

Debra sat back against the wall and let her head fall back, "You're insatiable. Remember Brandy, if you cum in the water you're going to be the one having to clean the pool." Debra laughed at her inside joke. Don continued his massage and I sat back and enjoyed his touch.

Don pulled my foot closer to his crotch. He rested the heel of my foot on his lap. He gently moved my foot from side to side rubbing my heel up and down the length of his hard cock. Don continued his foot massage before asking me for my other foot, "Brandy, bring up your other foot so I can massage that one too."




Pool Boy Gets Dressed Up Ch. 03



I quickly complied, but had to use my hands to keep my balance in the water and to hold myself under the water. Don released my right foot, but left it in his lap resting on his hard cock. He grabbed up my other foot and began to massage my left foot. I was in heaven, being massaged by one of the best looking men I have ever seen. As Don kneaded my foot he pulled me off balance in the water and my right foot slipped down. Now my foot that was just resting on its heel was not resting between his crotch and the entire bottom of my foot lay along Don's cock.

I was afraid to move it away too fast, but at the same time I liked feeling his cock. I embarrassingly began to pull it away until Don brought his legs together, locking my foot against his cock. Don gave me a wink, "It's ok, just enjoy the massage Brandy," Don patted my foot between his legs. I looked to Debra for her disapproval, but she continued to sit back sipping her margarita and enjoying the warm water.

My leg was now clamped between Don's legs. The water made the hair on Don's legs lightly touch mine. The feeling was exquisite. Don continued to use his acupressure skills to relax my body and keep it in a state of arousal. My head lay back, just over the edge of the spa. Don's hairy legs continue to caress mine, and his massage was bringing me to the edge of an orgasm. 

I was so caught up in the feeling that I didn't realize how close I was to cumming until Don increased the pressure on my foot just a bit too much. My eyes squeezed shut and my back arched up out of the water exposing my hard cock as it pressed skyward causing my suit to tent. As the intense feeling rushed through my body was sent into an intense orgasm. "Oh my god, NO! Oh shit, NO!" I screamed as I felt the cum surge out of my cock as it pushed its way through my suit like a bubbling fountain. I felt the hot fluid fill my suit and coat my cock before it dissipated into the water.

My body finally relaxed as I sunk back into the water. My head cleared and I opened my eyes, embarrassed. Don was still holding my foot. He had the biggest grin on his face, "Now you can really relax Brandy."

I looked over at Debra, who was grinning from ear to ear, "I told you he had magical hands. Isn't that the greatest orgasm you can have without being stuffed with a nice cock?"

I lowered my head in shame. I wanted to flee from the spa, from the house, from my life. I started to cry, "I'm so embarrassed. What you both must think of me. I think I better go."

Debra reached her arm around me and drew me into her bosom, "Now don't you worry your pretty little head. Besides it was Don's fault. He's like a child never knowing when enough is enough. No need to be embarrassed in front of us. Like I told you before, this is your safe place. You can truly be yourself with us." Debra turned to Don, "Now you made Brandy feel bad and she wants to leave. What do you have to say for yourself?"

Don glided across the spa and put his arms around Debra and myself and gave us both a hug, "I'm sorry Brandy. I felt the tension in your foot and knew that there was more there than just muscle tension. I thought an orgasm is the best body release. Debra and I are so open about sex that sometimes I forget that others may not be. I guess I got caught up with how attractive you are."

Don's words were so comforting to me. Was I that attractive as a girl? Don pulled me away from Debra and into his arms. My face rested into his neck. My arms went naturally around his waist drawing me closer to him. Don's hands lightly caressed my back and hair. I was still weeping into his neck, but was beginning to calm down. Debra pressed her body against my back, sandwiching me in a warm reassuring hug. 

Debra leaned close to my ear, "It's ok baby, Don and I want you. Please don't go. Stay with us. Be with us." As Debra said this I felt the straps on my suit slip off of my shoulders. Debra forced my suit down my arms as she reached around to my chest and started to lightly pull on my hardening nipples. I moaned into Don's neck, "Mmmm."

Don's hand continued to caress my back as Debra worked my nipples. Debra lifted me lightly up in the water as she pulled my suit completely off. She guided me down onto Don's lap. Debra pushed her body against my back again, but this time I could feel her naked breast against my skin. Don's hand moved down to cup my ass. 

I moved my hand up to Don's chest and raked it through is hair. Don moaned in appreciation, "That feels so nice Brandy. You are the perfect girl for me and Debra." For the first time I felt Don's hand on my little cock as he gently rubbed it.

I pushed my face into Don's neck and started to kiss and lick his skin. His skin tasted so good. He smelled so good, so manly. I real man, holding me. Debra started to kiss my ear, "Do you want Don to make love to you Brandy? Are you ready to feel a real cock fill you up? Just ask him. Tell Don what you want."

I gently pulled my head away from Don's neck and looked into his beautiful green eyes, "Please make love to me Don. I want to feel you inside me. I NEED to feel you inside me." 

With that Don gently grabbed the back of my head and held me as he guided his lips to mine, "Of course baby I will make love to you." Don kissed me. His lips were so soft against mine. His tongue gently parted my lips and slipped into my mouth, it took my breath away. There was nothing forceful about Don's kiss; it felt more like his tongue melted into my mouth.

Debra lifted herself out of the water and grabbed the towels. Don and I followed, each taking a towel as we stepped out of the spa. Don dried himself off then hooked a thumb on each side of his suit in order to pull them off, when Debra stopped him, "Stop! Don, let Brandy unwrap her prize."

I stepped toward Don, standing so close I could feel his heart beating from his chest. Don took his finger, placed it under my chin, and tipped my face up to his. I melted back into his arms as he again gave me the most emotional kiss I have ever felt. Don towered over me as I felt his hard cock pressing into my stomach. I slowly kissed, and tasted, my way down Don's torso. I tasted his right nipple first, feeling it harden under my tongue. His skin tasted so nice. I softly nibbled as his tit. Don held me tight, "Oh, yes. That's it Brandy suck my nipples, bite them."

Don continued to encourage me as I licked and kissed my way across his chest to his left nipple, "Mmmmm, so nice. Your lips are so soft. You tongue is so hot against my skin. Ya, that's it, lick that tit, get it nice and hard. MMMM. Bite it baby, show me how much you want it." 

I was intoxicated by his taste and smell. Just like Debra, Don's voice coaxed me through my first time making love to a man. I rubbed my face across his washboard abs and furry stomach, following his treasure trail down to my reward. I reached around Don's ass and sunk my hands into the cheeks of his hard flesh. I pulled Don's cock to my face and kissed the length of his cock through his suit.

I loosened my grip on his cheeks, slid my hands to his sides, and slowly pulled his suit down. I wanted to savor the feeling and site as my first cock came into view, Don's cock. I pulled the suit away from his cock to allow the head to be free. It was more than I could imagine. Debra may have had a replica made of Don's cock, but it was nothing to the beauty of the real thing. 

My hands moved along the inside of Don's suit, moving back to his tight ass cheeks. I moved forward to just taste and lick his head. I squeezed his ass and pulled him to me. My forehead pressed against Don's stomach as I looked down at his cock. My mouth was watering, and dry, at the same time. I slowly stuck out my tongue and pressed it into the clit at the center of his perfectly shaped pink head. I felt a slippery drop of precum ooze out as my tongue probed his cockhead. My heart was beating so fast I thought it would burst from my chest.

Don held my head and softly stroked my hair as he sucked air through his clenched teeth, "Phwww, that feels so damn good baby. That feels so nice. Run that tongue on my cockhead. Taste it baby. Lick all around the head. MMMM. What a good little cocksucker you are."

I tugged down on Don's suit a bit more, allowing half of his cock to be free from its confines. I licked his head some more, and then I slowly ran my lips and tongue up and down the length of his shaft. Each vein pulsed under my tongue. I continued to pull down Don's suite until finally his balls were freed. 

I moved my head back just enough to take in the site of his well-groomed cock. The hair above his cock was well manicured to a small squire patch that was closely trimmed just above where his shaft emerges from his body. His low hanging balls were the size of golf balls, soft, and smoothly shaven. His skin was that same light olive tone and it was obvious that he sunbathed nude by how there were no tan lines. Simply flawless in my eyes.

I pushed my face into his body, right under his shaft. His balls pressed into my cheeks. I took a deep breath as I kissed his ball sack. I gently kissed and lick every inch of his balls and cock. There was a drop of cum dangling from his cock head. I used my tongue to just touch the tip of the falling drop and, following the stream up to his cock head with my tongue, I engulfed his head and five inches of his cock. 

I used every skill Debra showed me in the last week to make Don happy. His cock seemed much thicker than its replica, but more pliable. His precum tasted sweet and felt so good swirling around my mouth. I gently pulled on Don's balls forcing his cock to tighten and go further down my throat. I was very pleased with myself that I was able to take about seven inches down my throat. My goal was to press my nose into his little patch of hair above his cock. I hope that I will other opportunities to make that happen.

Don pulled his cock out of my mouth. Don grabbed his shaft and lightly caressed my face with his cock. Looking down at me, "You're very good. Let's go upstairs where we can all have a good time, shall we?"

Debra helped me up off my knees, "Come on you little cock sucker, let's get you the fucking you need. I need your tongue to take care of my pussy. You have me dripping and horny you hot little minx."

To be continued....



Pool Boy Gets Dressed Up Ch. 04



I used every skill Debra showed me in the last week to make Don happy. His cock was thicker than its replica, but more pliable. His precum tasted sweet and felt so good swirling around my mouth. I gently pulled on Don's balls forcing his cock to tighten and go further down my throat. I was very pleased with myself that I was able to take about seven inches down my throat. My goal was to press my nose into the closely trimmed little patch of hair above his cock.

Don pulled his cock out of my mouth, grabbed his cock by the shaft, and lightly caressed my face with his cock. Looking down at me, "You're very good. Let's go upstairs where we can all have a good time, shall we?"

Debra helped me up off my knees, "Come on you little cock sucker, let's get you the fucking you need. I need your tongue to take care of my pussy, you have me dripping and horny, you hot little minx."

Don hooked my arm around his and escorted me up the stairs, I felt like a girl at the prom. The three of us climbed the stairs naked and horny. Don opened the door to their bedroom and led me to the bed. As we got next to the bed Don scooped me up into his arms and walked on his hands and knees to the middle of the bed where he lay me down. I sank into the soft bedding as Don leaned in for another of his body trembling kisses.

Debra joined us on the bed, coming in from the other side of me. Soon we were all taking turns kissing one another. My hands were all over the two of them; lightly stroking Don's huge member, fingering the little nub above Debra's pussy which I know drives her wild, and alternating sucking on Don's nipples then Debra's. The entire time I felt a finger probing my soon to be fucked pussy.

Debra first pushed in her slender finger into my pussy. She continued to slowly finger fuck me, to loosen me up which was soon replaced by a much bigger finger pressing its way into my hot tunnel that I knew must be Don's. Then to my surprise, Don pulled out his finger and grabbed Debra's hand, together they put their forefingers together to form one and gently and slowly pushed it into my hot hole. "AAHHHH!!! Don't stop, please don't stop, fuck me please." I screamed as my hole stretched to accommodate their probing.

They continued to hold hands and fuck me as they both stared into my eyes. Debra spoke first, "Are you ready Brandy? You are about to cross over to another world, are you ready for a man to take your virgin pussy? Once Don fucks you the three of us will unite as one. Do you want to be our lover Brandy? Are you ready to commit to us?"

I look up into both of their faces, "Please, oh yes please. I have never been happier in my life. I want you both as lovers. Please make love to me. I know I love the both of you with all my heart."

Don kissed me on the lips and moved in between my legs. He lifted my legs up to his shoulders and placed the head of his cock at my entrance. Debra squirted lube on Don's cock and jerked it a couple of times to fully coat it with the lube. Then she inserted the bottle of lube into my hole and squeezed, I felt the rush of the liquid shooting into by pussy. Debra held on to Don's cock and guided it to my hole. This really was the three of us making love.

Debra swirled Don's cockhead around my hole before lining it up. Debra looked down at me, "Are you ready Brandy?"

I looked back at Debra, "More than you will ever know."

Don pressed forward and pushed the head of his cock into my ass. With all my training that Debra gave me, nothing prepared me for the warm sensation of a real cock penetrating me for the first time. I did remember to push out as Don pushed the first couple of inches of his cock into my waiting virgin pussy. Debra continued to hold Don's cock as he slowly fed me his cock, inch by inch. When I felt Don's full weight press against my pelvis I knew I was no longer a virgin.

I could feel the tears of happiness flow down my cheeks as I watched my lovers work together, sharing my first penetration by a real cock. Don leaned forward and started to kiss away my tears. Then I felt Debra start to kiss away my tears on the other side of my face. Debra consoled me, "There, there, it's all right now. He's all the way in. Was it everything you expected? Does Don's cock feel good inside of you?"

I lifted my head and kissed her, "Thank you. It is everything I could have imagined and so much more."

Don lifted back up and slowly pulled his cock out of my pussy, then slowly sawed his way back in, then out again. He was so slow and methodical about his movements. Making sure that his cockhead puts just the right amount of pressure in all the right places deep in my bowels. "Yes, yes, fuck me Don. Fuck me harder. Take my virgin pussy. Stretch my pussy. Fill me with your cum."

Don grinned down at me and pulled his cock nearly all the way out and slammed it back as hard as he could. "YES, that's it, harder, please fuck me harder." I screamed out in ecstasy. 

Debra swung her leg over my head, facing Don. I looked up into her wet, puffy lipped, hot pussy. "I need my pussy eaten and we need to quiet her screams before someone calls the cops."

I looked up to see Don and Debra sharing a deep kiss before Debra lowered her pussy onto my mouth. I dove into that pussy like it was my last meal. I pushed my tongue into her pussy as deep as it would go. Her pussy was hot. Her pussy lips were swollen as I sucked on one and then the other. I then opened my mouth wide and sucked them both in. I ran my tongue up and down her clit. I could her Debra scream out, "OH YA I'M CUMMING. FUCK THIS IS SO HOT."

Debra sent a long stream of her hot sweet nectar down my throat. Bringing Debra to an orgasm always gets me off, as I felt my pussy squeeze around Don's cock harder than I thought possible as I felt my hot cum shoot onto my chest and stomach. The pressure must have been too much for Don as he cried out, "OH ya I can't believe the pressure. I'm cumming. I am going to fill your virgin little hole full of cum."

I felt Don's cock tense and swell just before his hot cum started to fill me up. The pressure of his hot cum was so intense that his cum shot out my ass and onto Don's thighs. Don slowly pulled his cock out of my ass and rolled to his back. Debra swung her leg back over my head allowing me to gaze upon the cock that just fucked me. Don's cum was dripping down the shaft of his cock.

I quickly rolled over onto my hands and knees and crawled in between Don's legs. I wanted to taste his cum. I placed a hand on his thighs and moved my face forward. I first licked up the droplets of cum dripping down his inner thighs. It was pure nectar of the gods. I savored the feeling of his thick hot cum on my tongue before it registered how good it tasted. I then moved to the head of his cock, where a big white glob was spewing out. I opened my mouth wide, as not to touch the sensitive head with my teeth, and gently enveloped my lips around his head. My tongue gently flicked the white cream into my mouth. "MMMMMMM"

I could hear Don and Debra laughing at me. I was like a child trying ice cream for the first time. Don was still hard. He showed no signs of losing his erection. Don pulled my cock from his mouth, "There is more where that came from. You will be drinking a lot of cum sweetheart, don't you worry."

Debra was now on all fours waiting for Don's cock. Don walked on his knees, lined his cock up with her pussy, and plunged it balls deep into her wet pussy. As Don's balls slapped against Debra's ass, she voiced her acceptance "OH FUCK, YES. Brandy, get under me and eat my pussy and lick Don's cock while he fucks me."

I hungrily dived under Debra, from the side. I lay beneath her on my back looking up at one of the most intimate and beautiful sites I have ever seen. Debra's pussy was glistening with her pussy juices. Her pussy was spread wide by Don's big cock. Don's balls were hanging down, almost lying on my forehead. With little effort I could lift my head and taste any and every treat that lay before me. 

Don's cock slowly retreated from Debra's pussy, his shaft dripping with pussy juice, before he began his steady rhythm of fucking Debra. Don's balls waived back and forth before my eyes. Debra's juices became a frothy flow in no time. I reached out with my tongue and began to lick Debra's pussy. As Don lunged forward, bearing his cock in Debra's pussy, his balls slapped the right side of my face. I stuck out my tongue, and licked Don's shaft as it moved in and out of Debra's pussy. Debra's juices collected on my tongue as I slurped it up, relishing in the taste.

I moved my head down and caught Don's balls with my mouth. Don stopped as soon as his cock was fully embedded inside Debra's pussy. This allowed my time to enjoy cleaning Debra's juices off of Don's balls. "Oh ya Brandy suck my balls. Grab them with your teeth baby and pull on them. God, yes! That's it." I held onto Don's balls with my teeth, careful not to clamp down too tight, but tight enough to stretch his sac down as my head came back to rest on top of the bed.

I knew by stretching Don's nut sac that his cock would be pulled tight within Debra's pussy making him more sensitive. Debra must have had an equally gratifying sensation as they both rang out in unison, "Oh shit that feels so damn good. Don't stop Brandy."

I knew that they were both on the verge of cumming and I wanted to be the reason they went over the top. I wanted to make them as happy as they made me. I secured my hold on Don's sac before I moved my head towards Debra's chest, pulling Don's nut sac as far as possible. Don slammed his cock as deep as possible planting his cock inside Debra. I could see that Debra pushed back hard against Don, as her leg muscles flexed, gripping her pussy as tight around Don's cock as possible. 

Debra came first as her head shot up in the air and her torso came slamming down by my head, "I'm cumming, shit, shit, shit, my god..mmmmmmmm!" 

The pressure was too much for Don, as his fingers, that were gripping Debra's waist, turned white. I watched the underside of his balls pulse as I knew he was shooting a load deep inside Debra. Don blurted out incoherent grunts as he came, "Oh Fuck! I'm cumming.nnngggg! Ahh! MMMM!"

As I watched their bodies relax I released the hold I had on Don's nut sac, hoping that I didn't puncture him. Don's cock slowly slipped out of Debra's pussy. I quickly scooted back down under them just in time to be rewarded by a gush of Don's cream flooding from Debra's pussy. I opened my mouth, not wanting to lose a drop, and planted it at the opening of Debra's pussy. I lapped up the cum before letting my head fall back and pulling Don's cock into my mouth.

Don's cock was still dripping with his thick cream, and his cock was just soft enough to allow me to engulf its entire girth. Don's balls were resting on my forehead and I was able to look up to see, for the first time, Don's pink rosebud. What a site. So many things to explore, I thought to myself.

I licked every bit of fresh cum from Don's cock head and all of Debra's pussy juice off of his shaft and balls before Don pulled his cock out of my mouth, becoming too sensitive. Debra took my vacant mouth as an invitation as she lowered her dripping pussy onto my face, "All good cum sluts clean their messes. Eat me Brandy. Lick all of Don's cum out of my pussy. Make me cum baby, use that tongue like you know how."

I wrapped my arms around Debra's torso to hold on for I knew I was going to do my best to send this woman into an orgasm orbit. I ran my tongue up the entire length of her pussy before I sucked on her pussy lips. I know how much Debra loves her pussy lips sucked on as I rim the insides of her pussy. "Yes! That's it baby use that tongue. God suck my pussy harder baby. Eat Don's cum. Suck it out of me. I'm going to cum hard. Brandy, oh, yes, fuuucckkk!"

Debra's back arched up, trying to pull away, but my arms locked on tight holding her back so that I could continue to eat her through her orgasm. Floods of Don's juices mixed with Debra's sweet nectar rushed out of Debra's hot pussy. I could feel their cum dripping down the sides of my face. I shook my head back and forth while flicking my tongue deep inside her pussy. I could feel Debra's body flex and tighten as she shoved her face into a pillow to muffle her screams of pleasure.

Debra rolled off of me, not being able to take it anymore. Don sat back against the headboard as Debra snuggled under his left shoulder. I felt that the climax was over and my services were no longer needed. How do I get out of this awkward moment? Then Debra reached out her left hand, and Don raised his right, both beckoning me to join them. 

"Come here baby, come cuddle with us." Don's voice was so soothing to my ears. I crawled under his arm as he wrapped it around me and pulled me to his chest. The smell of sex was intoxicating. I lightly caressed Don's cock as he rubbed my back. Debra reached over and cupped her hand on my face. I looked up at her as she leaned down and kissed me on the lips.

I fell into a deep sleep, as we all must have, because when I awoke I could see that a couple of hours had past and Don and Debra were still asleep. We all started to stir; it was dark outside and looked to be the middle of the night. Nobody was expecting me tonight anyway so I just cuddled in with my lovers and enjoyed the body heat. We all drifted off to sleep until the morning light woke us.

Don pulled me and Debra into him and kissed the tops of our heads, "Morning ladies. I hope you both had as good a night sleep as I did? I can't remember the last time I had such a well fucked night sleep."

Debra stretched her body out, kissed me on the cheek and Don on his lips, "Morning loves. I think we all could use a shower. Why don't you two go ahead and get started while I run down and put on a pot of coffee?"

I was delighted to spend more time with Don's naked body. Don gave my ass a nice little love slap, "Come on sleepy head, let's get that pretty little bottom of yours into the shower?" I lifted myself up off of Don's chest and moved off of the bed. By the looks of the bedding, I would say that it would have to go out to the cleaners as well.

Don and I slumbered to the shower while Debra left the bedroom to make the coffee. I wondered if this was a one-time fling. Was the spontaneity over? Was Don going to be upset with what happened? Again, I was overthinking everything, but the happiness I felt I wanted to hang on to it for as long as I could.

Don entered the enormous shower and turned on the water and steam. Don reached out his hands and helped me pull off my wig. The glue stuck a bit to my hair but seemed to have pulled off without much of a battle. Don threw the wig out of the shower and onto one of the sink counters. Don reached over and grabbed a bottle of perfumed bath soap and poured some in his hand, "Come here sweetheart, let me bathe you." 

I rinsed my body under the warm water before stepping over to Don. My knees went weak as Don's soapy hands explored every inch and crevice of my body. His hands were like a million little electric needles touching my body. I was getting a hardon, what little there is of it. Don pulled me to his chest as he ran his hands up and down my back, "Feel good baby. Do you like when I touch you all over?"

I pushed my face into Don's chest, "Oh yes. You and Debra have made me so happy."

"The first time Debra and I saw you cleaning our pool we both knew you were the one to complete our little family. Debra and I both have a very specific appetite for sex. You not only fulfill our dreams of sex, but we have both become very fond of you, if you know what I mean?"

I was afraid to presume the wrong thing and look like a fool, when I felt Debra's body sandwich me in between the two of them. "What Don is saying Brandy, is we both do love you. You have turned out to be a great girlfriend and companion for me. We would like to make a proposition for you. Let's get cleaned up and go out to the pool, have a cup of coffee, and talk."

I couldn't imagine what they wanted to talk to me about, but right now I didn't care I was naked with my two favorite naked people. We lathered each other up and rinsed the soap off. Don gave me my enemas and cleaned me out. He was always gentle and never forced anything on me. We dried off and went straight downstairs. No clothes were worn.

Debra brought in a tray with our coffee and some Danish as we all sat at the table by the pool. Debra was first to begin. Placing a soft hand on my knee, "Brandy dear, I know how much you prefer being Brandy over Brandon. I can see how your eyes light up when you slip into a pretty outfit and get your face all made up." I agreed, but still bowed my head in embarrassment. 

"Don and I would like to make you an offer to come live with us as Brandy. Don't get me wrong, it's not that we want you just to be a sex toy, we want you to come live here as part of our family. We both love you like our own and we want you to be who you really are. Of course that would mean you would learn about our businesses, how they operate, and how we operate in business. We would travel the world. While here at home, you would have your own room filled with beautiful clothes."

I sat stunned as Don picked up where Debra left off, "Last night was fantastic. I felt a true emotional connection with you Brandy. Not like I feel with Debra, but our love goes beyond that. We know we can have you in our hearts and bed. Having you and Debra as part of my life would make me the happiest man on earth." 

I gave Don a funny look and giggled, "Here I thought I was the happiest man on earth." We all started to laugh. "When do you want my answer?" 

Don and Debra looked at each other with almost hurt feelings, "Well, anytime you feel comfortable. And if you don't want to be with us we would understand." Debra actually had tears in her eyes worried about how I would answer.

I stood up, walked over to Don, swung my leg over his lap, and sat down on his soft cock, "Good, because I couldn't wait another second to tell you that I would love to be part of your family." With that I gave Don a big kiss as I ground my little ass against his now hardening cock. Debra came up next to me and added her mouth to our kiss as we all hugged and kissed each other. 

Debra broke the kiss first, "We are so delighted. We have so much to prepare for. First we have to explain to your parents that you want to be Brandy and move in here."

"NO!" I screamed out, "They would never understand. Can't we think of something else?"

Debra patted my back, "Calm down baby. I prefer honesty, but we can start off with telling them that you have obtained an internship with Don's company and that you would be staying here in between flying around the world as our intern. You don't start school until September anyway, so that will buy us a couple of months to ease into this. We can call it a trial run for all of us. How does that sound?"

At the same time Don and I both said, "Perfect."

The doorbell rang and Debra looked at the two of us, "Stay here, I'll go get the door." Debra grabbed a terrycloth wrap and put it on as she headed for the front door. I stayed on Don's lap, started to kiss his neck, and grind my ass against his raging hardon.

The sound of Debra's voice broke us up from making out. "Is this how it's going to be every time I leave you two alone? Brandy you are such a little cock slut," she said with a wicked little grin on her face. Debra also had an arm fool of boxes and a couple of bags dangling from her fingers. "Guess what arrived? Part of Brandy's new wardrobe."

I jumped off of Don's lap, kissed him on the lips, and ran to Debra like a child on Christmas morning. Debra turned and headed back towards the stairs, "Come on Brandy, we have a lot of work to do." Debra and I went upstairs to one of the spare bedrooms, which is just as beautifully furnished as the rest of the house. Debra emptied her arms and hands onto the bed.




Pool Boy Gets Dressed Up Ch. 04



I opened the boxes and handed each new item to Debra. Debra began filling the empty closet and dresser with all of my new clothes. We finished putting away all of the clothes and cleaned up the bags and boxes. Debra pulled me into her arms, "We are going to have so much fun filling this closet and dresser drawers. I can't wait to take you shopping in Paris and Italy. Oh my god I just realized something, we have to get you a passport as soon as possible. Don is traveling to England in a couple of weeks and you and I are going with him." My head was spinning, things were moving so fast, and in directions I never dreamed about.

Debra ran back into the closet and tossed out an outfit for me to put on. "Say good-bye to Brandon sweetie, Brandy is here to stay." We both giggled as I slipped on my white panties with a pink bow on each side. I pulled on some knee high white stockings and slipped on a nice pair of black flats. Debra held up my jean skirt so that I could step into it. I so relished the feeling of pointing my toe down as I stepped into the skirt. As Debra pulled up my skirt she licked each of my nipples causing us both to giggle again.

I went to put on a simple peasant blouse when Debra stopped me, "Wait, you forgot your bra." 

I looked at Debra, "Really, why bother? Bras feel uncomfortable just hanging on my chest. I just don't have enough to even start training."

Debra held out her hands displaying two nice little B-cup booby forms, with life like pert little nipples, "Well if you put these in your bra I am sure it won't be hanging on you."

I looked at Debra's beautiful loving smile, "They're so real looking." I quickly pulled on the bra and took one of the forms from Debra. Debra inserted one of the forms into my bra as I did the other.

"There that looks perfect. We just have one more quick touch." Debra said as she pulled one of the forms away from my chest, peeled off the adhesive strips on the backside, and pressed it back against my chest. Debra repeated the process on the other side. "There, now they won't be falling out. You can even swim with those babies on."

I turned around towards the mirror, the transformation was fabulous. I slowly reached up and cupped each breast in my hands. I gently squeezed them, and then lightly rubbed my finger over the hard little nipples poking out through the bra. I watched myself in the mirror as I continued to feel myself up. I so wished they were real.

Debra wrapped her arms around me, hugging me tight, "You are so beautiful Brandy. Do you like your tits?"

I was choked up as I barely screeched out, "They're lovely. I wish they were real so I could feel myself playing with my nipples."

Debra kissed me on the lips and pulled away, "Maybe for Christmas. Now let's get your hair, makeup, and nails done. Don is taking us out for Dinner, and then shopping. Let's see how much we can spend before Don has a coronary." Debra pushed me towards her room and we both laughed as we glided down the hall.

Debra placed a nice blonde wig on my head and combed it into a nice short bob. She did my makeup like a professional and then painted my nails with a nice light pink coral polish.

While I sat and waited for my nails to dry, Debra put on a nice red silky blouse, jean skirt, and red three inch heels. She is still the most gorgeous woman I have ever seen. I noted to myself to practice walking in heels so that I could wear them going out without falling on my face.

Debra and I walked down the stairs as Don was just finishing his phone call. Don looked up at us coming down the stairs and we can hear the ending of his conversation, "I'll call you later. I have to go now; my vision has just been impaired by two beautiful women."

"WOW. WOW. WOW. Just give me a minute to grab a baseball bat so that I can keep the onlookers from getting too close. I am going take you beauties out on the town. Let's go celebrate our new union. And just to warn you two, when we get home I will expect one hell of night of earth shaking, ball draining, cum drenching S-E-X." The last word he spelled out slowly.

Don hooked both his arms out to us as we slid our arms through his loops and continued to walk out the door, in one fluid motion. We were already acting as one.

To be continued....



Pool Boy Gets Dressed Up Ch. 05



"WOW. WOW. WOW. Just give me a minute to grab a baseball bat so that I can keep the onlookers from getting too close. I am going take you beauties out on the town. Let's go celebrate our new union. And just to warn you two, when we get home I will expect one hell of night of earth shaking, ball draining, cum drenching S-E-X." The last word he spelled out slowly.

Don hooked both his arms out to us as we slid our arms through his loops and continued to walk out the door, in one fluid motion. We were already acting as one.

We strolled out to Don's car, the two of them towering next to me. I felt like a child going out with her parents, and probably looked like it too. Don opened the car door and held my hand as I stepped into the backseat. Don then opened the front door for Debra. Don was such the gentlemen. We drove out to the same mall that Debra and I had gone the day before. I was totally comfortable there since we spent the day there without incident. 

Don escorted us to a very nice restaurant where we dined on food I couldn't even pronounce, but it was very good. After dinner Debra took control and led the way through various stores. As she was loading my arms full of outfits to try on she mentioned to Don, "We have to get Brandy a whole new wardrobe for England, don't you think?" 

Don laughed and clapped his hands together, "My darling I couldn't agree more. And with that I am going to the smoke shop and buy a couple of cigars while you girls flatten out my credit card." We all laughed as Don scurried out of the female clothing store.

Debra called out at him, "Just for that I am buying me some things as well." Debra looked back at me with her beautiful smile and winked. "Let's teach him a lesson and buy out the store." We both laughed.

We had a truck load of boxes being sent back to Don and Debra's house, and Debra didn't seem to be slowing down. Debra literally grabbed me by the hand and pulled me from one store to the next. We finally ended up at the same shoe store that had the gorgeous flirty salesman. As luck would have it he was on duty again.

"Good evening ladies, how may I assist you?" My mouth dropped open as I stared into Sam's (as his name tag stated) beautiful sea blue eyes and the longest black eyelashes I have ever seen. 

Debra taking charge as usual, jumped right in, "Good evening Sam. My husband ditched us so we are going to punish him by earning you a great big commission." Debra turned to me with a grin, "Close your mouth and wipe your drool Brandy we have shoes to try on." Debra laughed as she pushed me towards the chairs so we can be fitted for shoes.

Sam laughed along with Debra, and I just blushed. I sat down on one of the chairs as Debra walked up and down the wall filled with shoes on display. Debra was grabbing an armful of shoes. Sam pulled up a low bench with an angled foot rest readying to measure my foot, again.

Debra called out to Sam, "Get her foot measurements and then I want to see her try on all of these."

Sam smiled, showing the whitest teeth, "Anything you want Debra. Will we be sending these to your home as well?"

"Sam you know me so well." Debra chimed back as she had at least a dozen shoes for me to try on. 

I kept telling myself to stop staring at Sam but I just couldn't take my eyes off of his slicked back black hair, blue eyes, perfectly sculpted jaw, and those blue eyes again. As he spoke I watched his Adam's apple jiggle up and down his lightly bronzed neck. I watched his hand as it moved down and grabbed my foot. Even his hands were perfect. Long tanned fingers, perfectly manicured nails, and a dark black tuft of hair protruding out the cuff on his shirt.

I shook my head back to reality as Sam lifted my foot onto the measuring device. Sam slipped off my black flat then looked up into my eyes, "Would you mind if I slipped off your stocking and put on a nylon stocking so you can try on the shoes?"

I nodded to Sam and just about came in my panties as his hand ran up my calf. He slipped his fingers in the top of my stocking and slowly guided it down to my ankle. I lifted my foot and he slipped of my stocking. His hands were touching my skin the entire time. I could feel myself leak precum and my cock strained against my panties. 

Sam scrunched up a nylon in his hand and slipped it over my toes. The palm of his hand glided against the sole of my foot and then continued up my calf. I bit my lip to keep from moaning out loud.

Debra broke my pending orgasm as she dangled a pair of shoes in Sam's face, "Can we see her in this pair first Sam?"

Sam was still holding my calf, and actually I felt him squeezing it just slightly, "Of course, let me go grab some shoes out of the back. I will be right back."

As Sam disappeared through the door to the backroom, Debra sat next to me, "Oh he wants you almost as bad as you want him." Debra emphasized her point by grabbing ahold of my cock through my skirt.

"My god girl calm down or your cum will be dripping right down your leg. He is gorgeous isn't he? I think we all come here just to have him look up our skirts. He is such a flirt, but I have yet to hear of anyone that has been able to take him home. I think he may like what you have for him." I felt my cheeks flush read again as Debra squeezed my cock.

It just occurred to me what Debra was saying, "Oh my god, did he just look up my skirt and figure out I wasn't a girl? Can we go now Debra, please?"

"Honey, he saw your cock the last time we were here. I am telling you he likes cock. I bet Sam will fuck you good and hard. He is a dreamy Persian god that anybody would love to have. But sweetie, I can tell he wants your pussy over any cougar that comes in here." Debra reached under my skirt and tugged my panties down and off. 

I never thought of stopping Debra from doing anything, even stripping me of my panties in a public place, so I just lifted my ass and let her pull them off. "Now let's see if his reaction changes. Brandy we are here until I am satisfied that you have enough shoes for all your new outfits. And that Sam wants to fuck you. You know you would suck his cock if given the chance, maybe I just gave you the chance." Debra winked again at me as she patted my hard cock.

Debra grabbed up my panties and noticed how wet they were, "Look how wet you got these? Oh you want him bad, you're such a little cock slut." Debra laughed at me and I just smiled back.

Sam came out the door balancing about six boxes of shoes. He sat back down and opened the top box. Sam pulled out a silver pair of ankle strap shoes with a single strap. He bent down and pulled up my foot to slip the first shoe on. One hand firmly held my calf, as the heel of my foot rested in the palm of his other hand. I watched his expression as he raised my foot, parting my legs, and exposing my hairless cock. I was not disappointed, and it appeared that neither was Sam, as his eyes locked onto my cock and I could feel the palm of his hand begin to sweat against my heel.

Sam released his grip on my calf reached down grabbed the shoe and slowly slipped it over my foot. The shoe slipped onto my foot like butter. Sam carefully wrapped the strap around my ankle and fastened it. As he guided my foot back to the floor his body leaned forward towards my crotch. He held his face in place as he pulled my other foot up to fit the other shoe. His eyes never left my cock. Sam put on my other shoe and placed my foot back on the ground.

Sam stood up and both Debra and I noticed his thick cock pressing down his leg. Sam held out his hand for me so that he could help me stand. I took Sam's hand and lifted myself up to a standing position. My small cock was hard enough to poke my skirt out just enough so that you could tell I was a guy. Thank goodness it was nearly closing time and the area we were in was void of customers.

Sam continued to hold my hand as I took a few wobbly steps around on the four inch heels. Though I was not used to heels, I was able to hold my own without looking too ridiculous. Sam spun me around in a pirouette before I sat back down on the chair. We all giggled as my skirt lifted just enough to air out my cock, but not high enough to show the world. As I sat back down my skirt was riding a little higher than before so Sam had a really good eye shot under my skirt.

We repeated the routine through various colors of peep toes, platform, pumps, slides, stacked heels, and my favorite, stiletto's. Debra excused herself to check out some jewelry and handbags while Sam and I finished our shoe show. Sam looked at me, "I have one more pair for you to try on, would you mind giving me a hand, the box is kind of high and nobody is left in my department to hold the ladder?"

"Why Sam, if I wasn't so shy I could swear you were trying to get me in the backroom alone. Of course I will come and give you a hand." I twirled my hair and batted my eyelashes is the most flirty pose I could muster.

Sam extended his hand and I graciously accepted it as he just about lifted me into his arms. All of those looks, and muscle too, this guy made my head spin. We walked through the back door and it no sooner shut before Sam spun me into his arms, bent over, and gently pushed his lips to mine. I wrapped one arm around his waist and the other moved up and combed my fingers through his thick hair. My lips parted and his tongue swirled its way into my mouth.

I could feel his monster cock pressing against my stomach. We separated and Sam looked at me, "I have always dreamed of a beautiful girl like you coming into my life. What is your relationship with Debra and her husband?"

I was a little caught off guard with the question, everything was moving fast with Debra and Don, but Debra was encouraging me to play with Sam. "I love Debra and Don. I don't think they would mind if I had a relationship with you."

Sam kissed me again, "I would like the opportunity to date you Brandy. You seem to be everything I have ever wanted, everything I have needed." 

With that Sam knelt in front of me and lifted my skirt and pushed his face into my hard cock. He rubbed his face all over my cock and balls before he engulfed my little dick all the way into his mouth. I reached down and grabbed his head with both hands and ran my fingers through his thick black hair. Sam reached both hands around me and grabbed my ass cheeks. He kneaded my cheeks before he spread them and placed the tip of his finger against my pussy. "Oh yes Sam do it, finger my pussy. You are so hot baby. Is this what you need baby, a nice cock in your mouth and a tight boy pussy to fuck?"

Sam answered me by shoving his finger deep into my pussy and deep throating my cock. My little cock barely reached the back of Sam's throat, which allowed Sam to tongue my balls at the same time. I was in heaven and about to shoot my load. I wasn't sure if Sam was ready for that but it felt so damn good. "Oh Sam you are such a good cock sucker. Oh tongue my little ball sack baby. MMMMM. Oh Sam you're going to make me cum."

Sam held me tighter and used his finger that was fucking my pussy to hold me against his face. Sam wanted my cum and I think he likes dirty talk too. I looked down into Sam's eyes as he sucked my cock, "You may be a ladies man on the outside, but baby I know you're a lady wanting a man on the inside. My little boy needs my cum. That's it cock sucker drain my balls. Suck my juice out. Here it comes baby. Ready to feel my hot cum shoot in your cock sucking mouth?"

Sam starting sucking me for all he was worth. He started to moan into my cock and he now had two fingers fucking my pussy with lightning speed. My balls tightened up, my pussy clinched tight around Sam's fingers. I could feel the head of my cock swell. I grabbed onto Sam's head and started to slam fuck his mouth hard, "That's it baby fuck my pussy hard. This is what you want isn't it my little bitch? You like being face fucked by a cock don't you? Well here it comes baby, drink my load. AAAGGGHHH!!!" I screamed out and shot my load down Sam's throat.

Sam did not want to let my cock go, but it was becoming too sensitive as I pulled away from him. I know the feeling of just exposing your deepest desires with someone, so I grabbed Sam's head and pulled him to me for a cum sharing kiss. I pushed my tongue into Sam's mouth and searched my cum out. I felt Sam relax and give into my kiss as he pulled me closer to him.

I reached down to Sam's cock and found that he had cum. As Sam and I kissed I could feel tears dripping against my cheek. I pulled away and looked into Sam's watery eyes, "Oh baby don't worry your secret is safe with me. If I can't keep a secret nobody can." With that I kissed Sam lightly on his lips.

"Brandy, I never...I mean I dreamt about this, but never thought it possible. This was my first time, please don't tell anybody. I just couldn't stop myself. You were all woman and man at the same time. What do we do now?" Sam pleaded with me.

"Sammy don't you worry I will figure out a way to play with you." I handed Sammy my pool boy business card with my cell number on it. "Call me so that I can get your cell number and we can chat some more. Don't worry baby, I think I know what you need. I will see about getting your deepest desires taken care of and I can guarantee that nobody will ever find out."

Sam lifted me into his arms and kissed me with such passion that he took my breath away. I straightened my outfit out, walked out the door, and back into the store. 

Debra was sitting waiting for me. "Well, well, well, you look like the cat that swallowed the cock. What have you been up to slut? And where is Sam, sleeping in the back?" Debra's smirk on her face told me that she wasn't mad.

As I got closer to Debra and told her, "Let's just say that Sam has to sneak over to Men's wear and grab a new pair of pants, his are kind of wet. I told him to put everything on your tab and send it to your house. But not before he applies his employee discount." I winked at Debra as I said this.

Debra put her arm around me and started to laugh as we went to find Don, "You are such the little whore. I love that about you. And listen to you, 'put it on the tab and send it home'. Brandy we are going to have a marvelous friendship."

We walked through the mall looking for Don. I was still free balling with all the people around and so unaware that it made me stay partially erect. I loved it. We found Don sitting in a real man's chair smoking a big sweet smelling cigar. Debra and I took a seat on each of the arms of Don's chair. Don put his cigar in his mouth and placed a hand on both of our thighs. "Hello my beauties are we maxed out on my credit card or do we have enough for some dessert?" 

Debra and I leaned over and kissed Don on each cheek as we all laughed. We left the mall and got back into Don's car. The car doors no sooner closed before Debra whirled around in her seat, "Ok Brandy, spill the beans what happened in the backroom?" Debra was like a school girl awaiting the latest gossip.

Don had a surprised look, "What did I miss while I was smoking my cigar?"

Debra laughed, "That is what I am trying to find out. Seems Brandy was smoking on a cigar too."

I laughed, "I did not as a matter of fact. And a lady doesn't kiss and tell."

"Bullshit, a woman always kisses and tells. What happened?" Debra giggled out.

I was having a blast with this, "You're right they do. Well you're not going to believe this but it turns out that Sam is not the womanizer he portrays himself to be. In fact, Sam prefers to be Sammy and likes the illusion of a woman but the cock of a man."

Debra and Don both laughed out, "NO. You're kidding right?" Debra wanted more detail, "That good looking Persian god likes dick? I don't believe you? I thought flashing your dick was a joke, I didn't think he would take the bait. I guess I am better than I thought with my gadar."

I filled them in with the details, "Oh ya, he took one look up my dress and he wanted it bad. We went in the backroom and he couldn't kiss me fast enough. Then he went down on me faster than, well, faster than I went down on Don." We were all laughing hysterically now. 

I continued with my story, "It gets better. Once Sammy nestled his face into my crotch he started to finger my pussy. I thought he would fuck me but as I prodded him I had a hunch and went with it. I started calling him a cocksucker and dominated him a bit. The guy ate it up and my cock too."

Debra was breathing heavy, "No, really. He not only likes cock but he is a sub like you?"

"You bet he is. I told him he is a girl on the inside and wants a big cock to fuck him. I hit the mark, because as soon as I discovered his true desires the guy shot his load in his pants. I never even touched him. He came with my cock in his mouth and me talking dirty to him."

I could see Debra's mind turning as she turned to Don, "I think we may have a toy to play with and, if I'm not mistaken, I think Brandy wants to be in charge of this one?"

I jumped on this, "Can I? I like being submissive with you two and you both can fuck me tell the end of time, but something about turning Sammy into a sissy cock sucking tramp that really turns me on. I want to get him to the point of begging for Don's cock and then have Don come in and fuck Sammy right into the cock sucking whore he wants to be."

We drove home and we all tore off our clothes as we ran up to the master shower to prepare for bed. Debra and Don showered up as I douched, not wanting to waste a second of time. We dried off and Don and Debra headed to bed. I had a little makeup to reapply. A girl's gotta look her best for her lovers. I slipped on a nice pink baby doll with matching panties and walked into the bedroom.

As I walked into the bedroom I could see there was going to be no foreplay tonight. Don was lying on his back naked, hardon sticking straight up in the air. Debra was sitting on Don's face facing the headboard. Debra was holding onto the top of the headboard and grinding her pussy into Don's face, "Come on eat me baby. I am so fucking horny. That's it move that tongue. OHHHH! YES! Bite my pussy lips. Stretch them with your teeth baby."

I crawled on the bed between Don's legs. He must have sensed my on the bed because his legs spread giving me access to his cock. I ran my tongue up his shaft and licked his dripping precum. I moved back down to his balls and started washing his balls with my tongue. His balls smelled so good and I could tell that Debra had her pussy on his pole. "You like my little treat I left for your Brandy? I came fast when I sat on Don's cock, make sure you clean all my juices up."

"Yes mistress. I am licking his balls now. I think you may have dripped down to his ass crack too." I said as I ran my tongue over his hairy hole.

Don moaned into Debra's pussy. I pulled my panties off and moved over Don's dripping cock. I was facing Debra's back and held her hips for support. I squatted down grabbing Don's cock and pointing it to my waiting pussy. I wiggled my ass to accommodate his head and to allow its entrance. Once Don's head broke through my pussy, I plunged myself all the way down his shaft. Don's cock filled me all the way up.

I grabbed ahold of Debra's hips and pulled her ass to my face, "Yes, Brandy, eat my ass while Don eats my pussy." I pushed my tongue deep into Debra's dark hole. Debra moved back down to rest her pussy on Don's face, then leaned forward opening her ass up for me to devour. 

Don and I worked Debra over orally. Don continued to gyrate his hips, grinding his cock into my pussy. I lifted up off of Don's cock and slammed back down in between eating Debra's ass out. Debra was ready to cum and so was Don.

Don began to pump his cock into me faster and faster. Debra was pushing back against both of our tongues, "Oh yes that's it. OH YES! FUCK!" Debra screamed out and went stiff as she filled Don's mouth with her cum juice. 




Pool Boy Gets Dressed Up Ch. 05



At the same time Don pushed his cock up as hard and as deep as his cock would go and froze. Don's cock swelled in my pussy before I felt the hot flood of cum release into my bowels. Don screamed out into Debra's pussy causing Debra to go right into another orgasm. "MMMMMMM!!!!!"

I rolled off of Don's cock and Debra swung her leg around and shockingly planted herself on my little cock. She was so hot and wet. My cock was lost in her pussy. Debra threw my baby doll over my head exposing my little tits. "Is this how you want Sammy? You want her to sit on your cock and ride you? You going to show her who is the dom one?" Debra kept grinding her pussy against my cock. Her juices were dripping down my balls.

Debra was teaching me to be dominant with Sammy, "You have to show her who's the boss Brandy. You need to take your cock and fuck her pussy. Get her ready for Don's big daddy cock. It is going to be so hot to see you two fuck Sammy." Debra was thinking out loud getting herself off. 

Debra started pinching and twisting my nipples causing me to moan in pleasure, "You like that bitch? You like your tits played with hard and rough don't you? Don come and stuff your cock in this cunts mouth to shut her up. I am going to work her over good." 

I turned my head in time for Don to shove his half hard cock in my mouth. I moaned with pleasure as Debra twisted my nipples hard. 

Don's deep voice guided me to my climax, "That's it Brandy hum on daddy's cock. MMMMM! Feels so good. Your moans are vibrating my balls. Twist her titties harder Debra, make the bitch scream on my cock."

With that Debra pulled both my nipples as far as they could stretch. The skin on my chest tightens as my nipples were stretched and pulled away from my chest. Debra held on to the tips of my nipples then twisted them with what felt like a vice grip. The pain and pleasure of my nipples felt so good. I screamed into Don's now hard cock.

The pain was too much and I shot my load into Debra's pussy. As my orgasm hit, Don shoved his cock all the way down my throat. Don's cock swelled and he shot his cum straight into my stomach. Don pulled his cock back and out of my mouth shooting three more gobs of cum on my face. Debra's sloshy pussy tightened up and she had another orgasm.

Debra leaned forward and licked Don's cum from my face before she planted a cum sharing kiss with me. Debra pulled back from our kiss, turned her body around, and planted her pussy on my face, "Clean your mess up cunt. I want every drop of your sissy spunk out of my pussy." 

I greedily lapped up all my cum, and her pussy juices, off of her thighs before I pushed my face into her pussy as deep as her pussy would let me go. I sucked all of my thick cum out of her pussy before Debra's pussy was too sensitive to take any more.

We all curled up together and went to sleep.

To be continued...