1 comments/ 89888 views/ 22 favorites Losing The Bet By: Storm62 I had lost the bet and now Jenny was going to collect. She had a really naughty smirk on her face as she let me in. "I was beginning to wonder if you were coming over." "I don't welch on a bet, even though I don't know what you're up to." "Just a bit of revenge, you might get to like it too." "So, what do you want me to do?" "Strip, then I can prepare you." "Prepare...?" "Just do it Steve." Shrugging, I took off all my clothes. "Boxers too." With a sigh I complied, revealing a cock that was already hard. "My, my, looking forward to this are we?" "I don't know yet do I?" "The first thing we have to do is remove all your body hair." "All?" "Except your head, we just need to cut that short." It took her over an hour. An hour that was quite painful at times. She didn't just use a razor, but waxing strips too, mainly on my balls and legs. In the end she was satisfied that the only hair left on my body was on my head. She went into the bedroom and came back with some clothes. "Put these on." I looked at them. "This is a maids uniform." "I know, put it on." A little unsure I began to put the clothes on. Bra first. Jenny gave me two gel falsies to pad me out a bit. Next was the dress. It was very short, barely covering my ass. She handed me the black stockings, hold-ups they were. As I slid them up my now smooth legs they felt really good. I pulled up the silky white knickers next. Another good feeling as the shiny material cupped my shorn balls. Finally came the shoes, black, with a three inch squared heel. Jenny bade me stand. The heels made my legs look quite feminine. Next she handed me the lacy wristlets and apron. The final touch was a blonde wig with maid cap on top. Jenny looked me up and down. "You look good as a woman. I'll get some make-up to complete the job." After she disappeared into the bedroom again I caught a glimpse of myself in a mirror. Shockingly she was right, I did look good. Jenny came back and began putting the make-up on. Lipstick, blusher, eye-liner, eye shadow, the works. I looked in the mirror again and didn't recognise myself. I did however quite fancy the woman I had become. "Very cute." Jenny said. "But you need a new name. Not Stephanie, too obvious." She snapped her fingers. "Got it! You can be Emma." "Okay, I'm Emma. Now what? I don't suppose you went to all this trouble just to make me hot for myself." "Hot for yourself huh? Maybe you'll be more into this than I hoped." She smiled. "I'm going to train you to be spit-roasted like a woman." I gulped. "You mean..." "Yes. Follow me Emma." She led me into the bedroom. "If I agree to this, will you do something for me?" Jenny paused. "Maybe. I like a challenge. What exactly are you proposing?" "If I go through with this, which I admit is turning me on; I want to see you..." "What!? Spit it out Emma." "I'd like to watch you fucked in the ass too." I blurted out. Jenny smiled thoughtfully. "Okay, you're on. Now get in here and kneel down." Stunned by her acceptance I did as I was bid. "First of all, I'll need to widen your asshole, so put this in." She handed me a tapered butt-plug with a harness attached. I eased my panties down and attempted to push the plug in. "Not like that. Let me." Jenny took the plug from me and applied some lube. She bent me forward and slid it in. "Do the straps up, it will hold it in for you." Again I complied. It was a strange feeling, but not entirely unpleasant. "The next thing is to teach you to suck cock." I looked up hopefully. "No, I'm not sucking you off; I'm going to use this on your mouth." She took out a strap-on and stepped into it. I was still kneeling in front of her and the plastic prick was inches from my face. "Lick it. Lick it like you would like to be licked." Tentatively I stuck my tongue out and ran it around the head of the dildo. "Good. Now take it into your mouth." I opened my mouth and took the strap-on between my lips. I had about half of it in when I began to gag and started to pull back. Jenny grabbed the back of my head and pulled me forward, sinking the dildo to the hilt. After the initial shock I found myself not disliking the feeling. "You will make a great cock-sucking slut. Are you ready to try the real thing?" Now lost in sexual desire, I nodded yes. "Good." She pulled out of my mouth. "Follow me then." I pulled up my panties and followed her to the door where she handed me a coat. -------------------------------------- I don't know where Jenny took me, it was a seedy looking place from the outside, completely non-descript. Inside though, it was obviously some sort of sex club. "See anyone you fancy to take your anal cherry?" I shook my head, nervous again now. "I'll pick then. You get on all fours on that bed." She pointed to a bed on a stage. I looked at her. "If you back out now, you'll never get to see me with a doggie will you?" Dumbly I nodded and took up my position. She came over with two guys who placed themselves one in front and one behind. The guy behind flicked up my skirt and pulled down my knickers. The butt-plug was still in place. He unstrapped it and pulled it out. I moaned slightly and then felt his hands on my ass cheeks, easing them apart. His knob was suddenly touching my asshole. "Relax." I heard Jenny say. With a sudden thrust I had a dick up my butt. I opened my mouth in surprise and that was filled by a cock too. The warm pulsing feeling from both pricks was strangely good. They both sank deep into me. I had pubic hair in my face and could feel balls on my ass cheeks. "Well done Emma. They're both all the way in. Now go for it." I began to rock backwards and forwards as the two guys took it in turn to thrust into me. My own cock felt as if it had grown huge. I wanted to touch it, to relieve the pressure, but instead I felt a moist mouth enveloping it, Jenny's mouth. The guy in my ass came at the same time as I did, my cum going into Jenny's mouth, his spraying into my back passage. Moments later the guy in my mouth began to twitch and then he shot his load into my throat. The hot sticky liquid tasted like nothing I'd ever tasted before. I suddenly knew that I wanted more. "Jenny, get some more. I want more." "I thought you wanted to see me fucked in the ass?" "I do, but now I want more cock. Please?" She sighed and nodded. At once I was surrounded by cocks. I was rolled over onto my side and my legs were pushed up towards my chest. A dick entered my ass again, easier this time, and another was pushed into my mouth. One was placed in either hand too. Those I began to jerk off. Then I felt another cock between my thighs. The knob end thrust through and brushed my own again raging hard-on. I was in a sexual haze like never before and just let them pummel my body while still wanking off the two in my hands. The prick up my butt spurted off and was replaced by another. The one in my mouth followed, the hot spunk coating my throat and then covering my face. I jerked off the two in my hands, their come splashing my face as well. The last anal intruder came at the same time as the one using my closely pressed together thighs. As their come spurted out, covering my ass and my cock, my dick exploded unassisted, splashing onto my stomach. Jenny knelt beside me, licking some of the come from my face. "Happy now?" She asked raising her eyebrows. "Thank you for showing me something so new." I gasped. "I never knew that being fucked was like this." "My turn now then. Move over so I can get ready." "You don't have to do anything Jenny, this feeling is enough compensation." "I said I would, so I will. Sit up and watch." I pushed myself up on my elbows, oblivious to the come drying on my face, ass and stomach. Jenny was on all fours next to me. A huge guy appeared behind her, a monstrous erection jutting out from between his legs. She gasped as he mounted her, sinking his swollen member into her welcoming ass. "Oh!" She gasped. "That's filling me up so much." I watched transfixed as the huge dick thrust in and out of the slim blonde. "Steve! Emma I mean, slide over here, I want your cock too." Obligingly I did so. She took my burgeoning erection into her soft mouth once more. "I can taste two lots of come on it." She muttered. I looked up at the guy still stoically pounding her from behind. "Oh god, his knob is all the way in me. I'm so full." She grunted. "He's coming, he's coming!" She shouted out, leaving my dick waving in the air. "He's filling me up with come." With that she passed out, leaving me frustrated and with a raging stiffy. -------------------------------------- "Let me take care of that." A vaguely familiar redhead said, dropping her mouth to my cock. She was good and I came quickly. She swallowed the whole load, not spilling a drop. "Nice. Are you busy at the moment?" I shook my head. "Want to come with me for a while?" I nodded. "Come on then." The redhead, who I now recognised as Karen, the girl from my local shop, led me into a side room. She closed the door behind me. "I thought you might be a repressed bi-sexual, but I didn't think you were a cross dressing masochist." "I...I'm not. I think." "Looks like it to me." She smirked. "Kneel." I dropped to my knees. "Good. Now lie on your back." I obeyed again, smoothing down my skirt over my stiffening cock. "Leave it out. In fact pull your dress up, let me see your shameful dick." I complied. "Lie still." She picked up a big candle and lit it. I watched her apprehensively as she stood over me, the lit candle in her hand. She tilted it and dropped melting wax on my cock. I winced and my dick twitched. "Thought so." She put the candle down and slipped off her knickers. Picking the candle up again she knelt over my face. "Lick." I stuck out my tongue apprehensively and lapped at the folds of her pussy as she dropped more wax onto my dick and shaved balls. "That's good. Keep going." She panted. I plunged my tongue into her slit, causing a slight gasp. Still she dribbled wax onto my groin. Despite the pinpricks of pain my cock was getting hard, and not just with the wax solidifying around it. Karen shifted my position. She pulled my legs up either side of her so I was balancing on my shoulders, my tongue still exploring her pussy, my waxed dick and cum-seeping ass in front of her face. She pushed the unlit end of the candle into my butt. It slid in easily. For a while I felt nothing and then the wax made its way down the candle and onto my ass-hole. The pain was only momentary but intense. It also felt good. Karen stood reluctantly, taking her sweet tasting cunt away from my questing tongue. "Stay there. I need to get some things." I waited in my strange posture, candle wax running into my ass-crack, wondering why I felt the need to be dominated. I heard Karen return. "Good girl." "I'm not..." "But you want to be. Sorry, but I can't help you there." With that she cuffed my hands beneath me and then secured them to the floor. She did the same with each ankle, pinning me into this awkward contortion, my waxed cock pointing at my own face. "Now I'm going to stuff this into that slutty ass." She said, holding a long double-ended dildo in front of my face. "No! It'll never fit!!" "Don't be so negative, of course it will." With that she pulled the candle from my butt and thrust almost half of the dildo in instead. I moaned in pleasure, what a sensation! My cock was expanded so much that the wax was starting to crack and fall away into my face. Karen leant down and swept it away before easing the monster dildo part of the way out of my ass and then thrusting down again. Now I was impaled on almost half of it. She smiled, raised her skirt and stood over me. She rested the other end of the dildo at the entrance to her snatch and slowly sank herself onto it. She began to ride it, slowly at first and then building up speed. The faster she went, the farther the dildo was pushed into my butt. "Soon, soon." She panted. "Coming soon." "Make me come too, I need to come." My pre-cum was dribbling onto my face. "Oh, but you will come. You'll come by yourself slut." She panted just before a juddering orgasm shook her. Weakly she raised herself from her end of the dildo. "Make me come." I begged again. Karen quickly recovered and she put her hands around the phallus, still glistening with the juice from her pussy. Her eyes shone as she began to work the fake cock further and further into my ass. All at once my dick began to twitch and my spunk shot into my face. I opened my mouth to receive it. "Such a slut. Coming just from having your ass fucked. And then swallowing your own spunk." Karen laughed. "Well, time I was going." She got up and began to walk away. "You can't leave me like this." I called out. "Of course I can. It's someone else's turn to play now." -------------------------------------------------------------- I was left for twenty minutes in that contorted position, my dick dripping cum onto my face and the huge dildo stuck in my ass. And then I heard someone enter the room. I hoped it was Jenny come to take me away, but I was disappointed. There was a click of heels as the newcomer walked around me out of my vision. "I'm glad Jenny was wrong about you." "Who ..?" "I'm your new mistress." She came into view. It was Sharon! "I won you in a bet with Jenny. She didn't think you'd cum from having your ass fucked by a dildo, but she was wrong and now you're mine." She ran her hand over my stockinged leg. "What... what are you going to do?" "Well first, I'm going to have two cocks stuck into your butt. At the same time!" "NO! I'm not big enough down there." "But you are now; your nearly virgin ass has stretched out already." She clicked her fingers. At once there were two men stood over me. I could see their naked dicks quivering above me. They stood back to back, astride a leg each, pointing their dicks at my still filled asshole. Sharon reached forward and eased the monster phallus from me. Before the hole could shrink both cocks plunged in. My ass was suddenly full of throbbing hot meat. My own dick began to stiffen again, I couldn't believe it. What sort of slut was I? The two intruders began to move. One pulled part way out and then thrust back in; the second one did the same. They took it in turns pistoning in and out of my butt, gradually increasing in speed until it felt like they were both permanently deep inside me. Sharon crouched over my face still caressing both my stocking-clad legs. She leant forward between the two legs of those above me, still pile-driving me, and licked at the pre-cum now oozing from my raging hard-on. I could feel my orgasm building. Before I came both dicks in my ass suddenly shot their load, filling me with more cum than ever. They both stayed in me until they had stopped coming, before withdrawing and vanishing. Sharon held my engorged dick, preventing me from letting loose. "MMmm. There's so much cum in you it's seeping out." She laughed. She was right, I could feel spunk running between my buttocks and down towards my balls. Still holding onto my dick she lent forward again and began to lap up the escaping jizz. "Tasty." She cooed. My dick felt like it was going to explode now, so much so that I was whimpering. Finally Sharon relented. She dropped her mouth around my aching cock and released her grip. Mere seconds after her tongue had begun to tease me I shot my wad into her throat. She pulled away and the rest of my load went into my face again. Sharon seemed amused by this. "I wonder what you'd look like covered in cum?" She mused. "Still, that can wait. I have to get you ready for your next game." I wasn't sure I liked the sound of that. Sharon untied me and helped me to my feet, waiting until I got the feeling back into my limbs before leading me to a bathroom. "Clean yourself thoroughly." Sharon commanded. "That includes inside your ass." I did as I was bid, giving myself an enema and washing the cum and sweat from my body. Then, freshly laundered, I stood before my new mistress. Sharon looked me up and down. "Not much to work with, although the legs look good." She smiled to herself. "You'll make a fine toy for me to dress up and play with." I wasn't sure I liked the sound of that. I knew Jenny would never go too far, but Sharon? Sharon had a mean streak. "Put those on." She commanded, handing me what looked like a pair of black latex panties. Except they weren't panties. In the back was something like a large dildo. In the front was a pocket that was obviously where my cock was to go. Obviously because in front of that was a fake cunt. Any cock entering that would be rubbing against my own dick, held in the pocket. Gingerly I pulled the strange garment up my legs. "Your cock first." Sharon said helpfully. I slipped my dick into its latex prison. This left the dildo poking against my butt hole. "That too." Sharon was grinning evilly at my discomfort. "Can I have some lube please?" Sharon raised an eyebrow. "Mistress?" I hazarded. She nodded. "Better." She squeezed some lube into her hand and then worked it around the dildo head, sticking a finger into my ass to lube that too. She positioned the thing at the entrance and pushed. It went deep into me. Despite my predicament I couldn't help but enjoy the feeling of something in my ass again. Sharon crouched behind me as I smoothed the latex briefs down. Suddenly the thing in my butt wasn't solid anymore. I looked around puzzled. "The sheath in you can expand to take anything up to ten inches long. Won't that be nice?" I gulped at the thought. "Now here's the rest of your outfit." She said pointing to a pile of clothing. "You have half an hour to get it on, then I'll be back to finish up." Sharon left. I looked at the neatly folded pile. It was some kind of latex nurses uniform. The first thing was a pre-filled bra. I pulled it on. It gave me a bosom somewhere in the region of 36D. The rest of the uniform was donned quickly. The latex stockings were a bit tricky to get on smoothly and when I put on the six-inch heeled shoes I wondered how I was going to be able to walk. I left off the hat because I had an idea that Sharon was going to bring me another wig. As I was ready before her return I decided to practice walking in the tall heels. It wasn't as hard as I'd thought. I was feeling unaccountably pleased with the way I moved when Sharon came back wearing a similar outfit to the one I now wore. She looked at me appraisingly. "You don't make a bad looking girl you know. Maybe the waist could be cinched in a little. And those heels bring out the best in your legs. Where is the hat?" "I'm sorry mistress; I thought you would be requiring me to wear a wig again." "Not this time. But you do need make-up, so it's a good thing you left the hat off for now." She sat me down and began to work at putting make-up on my face. After twenty minutes she stood back and handed me the hat. I looked into the mirror to help me put it on straight. Once more the face that looked back at me didn't look like me, but again it gave my incarcerated dick a twitch. "Come on nurse, there are patients waiting for us." Sharon said. I took a last look at my reflection and then followed her out. "Us, Mistress Sharon?" "You don't think you're the only one who's going to have some fun do you?" We entered the main room and went to the main stage, around which were twenty or so naked men. Sharon stood with her hands on her hips. "Come on then guys, form an orderly queue. The nurses will see you now." She knelt in front of the first 'patient' and took his knob into her mouth. I followed suit, the guy's cockhead rubbing against the roof of my mouth and into my throat. I was surprised at how easy it had become for me to take a cock in my throat. Part of me was still disgusted at my enjoyment of this new-found talent, but mainly I revelled in my cocksucking ability; I loved to give head now. Losing the Bet "They stink at free throws!" That was the start of this adventure. Kind of unexpected to tell the truth. When our group gets together we often make silly bets with weird payouts. We're all generally too poor and cheap to make bets about cash, so we like to come up with dares or actions or sometimes even chores the loser has to do. One time I had to wash a buddy's car. Mike had to prank call his boss (yes, we were smart enough to use a pay phone, which you can actually still find sometimes). Timmy had the worst one so far. He was so sure he was right about Kerry beating Bush in 2004 that he had to do a 5k running race wearing nothing but a Speedo, a cape, and his shoes. He did end up writing in marker on his chest "yes, I lost a bet" so that people would stop asking about it. He actually made the paper with his outfit, which is when he realized he should have worn a batman mask as well. Copies of the newspaper picture kept showing up in his office for years. Normally, it is just the guys of the group that are dumb enough to put in for the bets. Sometimes though, one of the girls gets adventurous or drunk or confident enough to lay one down. Mike's wife, Katie, had to take over carpool service for Julie's week. Whenever a girl was crazy enough to bet with a guy there was always some type of sexual subtext. Or at least an attempt at it. Usually, they wouldn't agree to the bet and the few times they did they ended up winning and the guy had to do something stupid, like sing his undying love to her at a karaoke bar. But, as all stories here demonstrate, things often take strange and unexpected turns. My wife, Sharon, went to Kentucky which, if you recall, had a spectacular basketball team in the 2009-2010 season and they were expected to breeze easily through the tournament and play Kansas in the final. Jason, however, went to West Virginia. During a night out, with plenty of drinking, Sharon was shooting her mouth off about how Kentucky was the winningest hoops program ever and all that stuff. All of us were getting sick of it but Jason was really having none of it. He kept saying how Huggins would coach WV over Kentucky even though WV had far less talent and clearly less history but she would get in his face about John Wall carrying everything. Finally, he had had enough and told her to put her money where her mouth is. The room actually got pretty quiet at that point. Most of us were pretty lit and we all knew what a male-female bet would be like. Sharon didn't even hesitate about the bet. She said that Jason would have to clean our house when Kentucky won. I'm not sure why, but she thought the bet would be even. Actually, I don't believe she thought there was a chance she would lose the bet. So, she nodded when Jason said she would have to clean his apartment. But then he dropped the bomb everyone else was expecting. If Kentucky and Sharon lost, he said, she would have to clean his apartment while wearing a French Maid outfit he would pick out from the costume shop. As a little back story, our group is mostly made up of players from our coed softball team, with a few spouses and other hangers on. Most of us are in our late 20s or early 30s, with a few older guys who lend stability to the softball team. About half of us are married. Sharon and I had both turned 30 in the last year and neither of us was happy that our youths were slipping away. Both of us were working harder than ever, and needing to blow off steam every once in a while. For years I had been trying to get Sharon to dress a little sexier but she had resisted most of my efforts. Until we turned 30 that is. I think she realized she might not ever be able to dress sexy if she didn't do it now. Either that or she realized that she enjoyed the attention she got from me and others when we went out and she wore a low-cut shirt, or short-shorts. Every once in a while she would agree to wear a tight shirt that allowed for her pert nipples to poke through. For the past few months she had been flirting much more often than normal. I used to think that I would be jealous about a girlfriend or wife that flirted with other guys. But once it started to happen I had to admit that I was really turned on. She had been particularly flirtatious with Jason over the past few months. During a party at his house she had some bread crumbs on her shirt and managed to talk him into plucking them off. The tight shirt with no bra left little to the imagination that night and her nipples were showing off. Jason did his best to pluck off the crumbs and made little or no contact, but it was a great sight. At the time, I was extremely conflicted. On the one hand, I was hurt and jealous that my wife was encouraging another guy to touch her breasts. On the other hand, my cock would get hard every time I thought about the event. The more I thought about it the more I came to terms with how I felt and how I actually wanted things to go further. What would it be like if one of the guys saw her tits? What would be like if they saw her naked? What would it be like if things went further? The more I thought about it the more I got worked up. Finally, I had no choice but to let her know how I felt. I was scared to think what she would say. I'm not sure if I was more scared that she would call me a pervert or that she would jump at the chance to mess around with other guys. At first, I just kind of joked around about how it would be funny if she lost her top when we went to the beach and some of the guys saw her tits. She kind of chuckled at that. But she got kind of thoughtful. And we had amazing sex that night. Back to the bet -- Well, if you're a college hoops fan you already know that WV upset Kentucky in the tournament. Like any good fan, Sharon was beside herself. She puts so much into her support for the team that she sometimes gets depressed when they lose in a situation like that. With this loss though, she didn't have time to be depressed, because Jason was on her as soon as the buzzer sounded. "Oooooohhhhhh! This is going to be so great! My apartment is a mess and it needs a really good cleaning." "I, I, I. well shit." Sharon's face was scrunched up pretty seriously at this point. I couldn't tell if she was more peeved about the game, losing the bet, or having to clean someone else's place. "Saturday for the final four would be a great time to clean the place. Let's all party at my apartment! Sharon is going to do the cleaning! And she'll be in a French maid outfit kids." Sharon flushed in embarrassment, but, because I know her, I could tell she was a bit excited about the whole thing. She put her hand on my thigh under the table and gave me a squeeze. Lately, she would quickly move her hand away, but now she was leaving it there, slowing moving her fingers in slow circles. Kind of like we used to do back when we were dating. "Look Jason. You've seen our house. I'm not very good at cleaning," she mumbled. "Don't expect miracles." "Oh honey," Jason replied. "It is only a little about the cleaning," he said with a glint in his eye. Sharon's hand moved further up my thigh, getting dangerously close to intimate contact. Already, it wouldn't be appropriate for me to stand. During the drive home that night Sharon kept wringing her hands. I could tell she was fretting about the bet, but actually afraid that if I talked to her about it she would come up with some reason not to follow through. Which would be a huge disappointment. Finally, after long enough, I asked her what she was thinking about. "I'm pissed!" That's not really what I thought her response would be, and my first inclination was that she was mad at me for doing or not doing something, or saying or not saying something. "I can't believe my Cats lost. I feel like there is an empty spot in my heart. Several of those guys are seniors and will never get to play another game." To be honest, I had almost forgotten about the game, immersing myself in the bet. But I patted her leg and consoled her as best I could. I love college basketball, but my alma mater hasn't been in the Final Four since before I was born and have only made the tourney a few times since. It is just tough to get emotionally involved in a team like that. But when your team is always in contention, and expected to win, losing in an upset like that is heartbreaking. "You don't think Jason will make me watch the Final Four do you? I don't think I can stomach watching another game so soon." "Well, maybe you won't have to watch the game since you'll be busy cleaning." Good God, that was probably the worst thing to say. Not supportive, and a reminder of the bet. She hates cleaning. Before I even finished the sentence her head whipped around so fast her hair flew up. I'm going to spare you the argument, but I think it is clear that nothing sexy happened the rest of that night. As the week rolled on, a strong weather system started building. That's important, because almost all of us are in some sort of emergency management job. The big party for Final Four night steadily got smaller and smaller as everyone got called into some sort of duty. By Thursday, we were down to Jason, Sharon, myself, and Jason's roommate Pete. And then I got the call. I had to head to Charlotte, about three hours away for a day or so. With the games on Saturday, it wasn't clear if I would be released to come back. But the bet wasn't with me, it was between Jason and Sharon and neither of them had any relation to the emergency roles. I actually started getting nervous about the conversation Jason and I had when Sharon wasn't around. He asked how risqué he could get with the outfit Sharon would have to wear. After thinking about it a bit, I told him to get something as risqué as he could find. Sharon and I had joked about costumes like this before, and I had pointed out things like this when we were looking for Halloween costumes. She never really jumped at the idea and the department store costumes were sexy, but not any more outlandish than you would see on a network TV show. Either way, when Sharon learned I might not be there for the game she was beside herself and we had to have a chat. "I'm not sure I'm comfortable with this," she told me. "I'm not sure about it either. But a bet is a bet. I'm going to try to get back for the game. Just be cool. Heck, you don't even have to be in the same room with the guys if you don't want to." I was as much talking myself into it as I was Sharon. In the end, we agreed that she had to go through with paying off the bet. And I would do everything I could to get back for the game. When Saturday rolled around I really was stuck in Charlotte, hoping for a reprieve from the weather and potential crisis. If I could get out by six I could make it for the start of the game, but it was clear I wouldn't be there for any pre-game activity. Sharon's agreement required her to arrive at 8 and put in an hour of cleaning before the late game. Fortunately, the weather cooperated and I was released from duty at 6. With some luck, I could get back in time for tip-off. I wouldn't be there for the cleaning, but Sharon was supposed to wear the costume through the game and get people chips and beer when they needed. I also had another plan. "I'm just getting out of here now. I should be there in time for the second half," I told her over the phone. I had actually gotten out an hour earlier and pulled over to the side of the road to call. "Second half? Are you serious? I have to be there by myself for 2 hours before you get there? I don't know if I can do this." "Look. We've been through this before. You have to do this. And we can trust Jason and Pete. We've known them for years. You'll be fine. It will be fun. And I'll be there soon. I can't wait to see you in that outfit anyway." A pause on the other end of the line was long enough I looked at my phone to see if the call dropped. "You still there?" I asked. "Yeah. But I think I have something to tell you." She may, at this point, have actually heard my eyebrows rising at this. "Go ahead." "Well, I don't know how to say this." "Just say it Sharon. What's wrong?" "It's just that, well. This whole thing. Um. I am really horny right now." Wow! "I'll be there as quickly as I can. Might have to break a few speeding laws. But I'll get there. What are you going to do?" Her voice got really low, and I think she was touching herself. "I'm going to go over there, change into the costume he bought me, and clean the apartment. I'm going to strut a little. When they want some food, I'll get it for them. When they want a drink, I'll get it for them. I've got some high heels, so my legs and ass are going to be on display. I'm going to bend over to get the beer out of the fridge and show off the bottoms of the outfit he got for me. When I bring the beer over, I'm going to bend over and show off my tits." "Wow." It's a good thing I was smart enough to pull over earlier, as I don't think I could drive. "That is so hot. How fast should I drive?" "Don't you really want to know what I'm going to do if they want more?" My heart started racing at about the same speed my mind was. I mean, I've always wanted her to wear sexy things and be more provocative, but this was even more than I had thought through. "Ahem. Well. Ok. What if they want more? "Mmm," she moaned, clearly pleasuring herself. "Maybe I'll let them." My cock jumped painfully in my pants, demonstrating what I had wondered about. Yes, this was turning me on more than I had been turned on since high school. "I better get going. See you in a couple of hours. Be careful." I fired up the car and squealed out of the rest area, hitting speed in seconds. Was my plan good or bad? This is the type of thing that could change a marriage and a life. To say I broke the law on speed would be to put it mildly. But even at speed there was no way I could get there even 45 minutes after Sharon was to start cleaning. The miles went by fast, but not fast enough. Even better, I never got pulled over, which could have been bad due to my job. About 8:15, about a half our away, my phone buzzed. I don't generally like to talk while driving, especially at the speed I was going, but this seemed important. "This is crazy," she said before I could even say hello. "Did you see the costume he got for me?" "No, why? What's wrong? Does it not fit?" "I'm in the bathroom and just changed into the outfit. It's a lot more, um, revealing than the ones we've looked at before." "What do you mean; they're supposed to be sexy. And I thought you had gotten into this." "No, this is much more. Well, much less than I thought. There's really not much there -- there, if you know what I mean." "I'm going as fast as I can. What do you mean about not much being there? That's the point isn't it?" "Well, the skirt is much shorter than I expected. The whole skirt is maybe 3 or 4 inches long. And it is sheer." Again, my cock jumped and I seriously got concerned about too much blood flowing from my brain so quickly that I would pass out. "But you've got the skivvies that come with the costume. Those cover more than most bikini bottoms." "Not on this outfit. It's just a g-string. And the front of that is sheer too." The nerves in her voice were no match for the emotions going through my head as I thought about her in a tiny sheer skirt with only a sheer g-string underneath. And that she would be spending time in front of my friends like that. "Um. Ok." Really supportive, eh. But it was all I could manage to get out. "And the top. It's um. It's pretty much just a black bikini. And it is sheer too." Oh God. I almost ran off the road. "Are you going to be able to do this?" I asked. Hoping she would back out but also turned on that she would go forward. "No. But I think I have to. Are you ok with this?" I think this was the first time she asked me if I was ok. "I think so, but just be careful ok." Man, just the thought of her in that outfit was making me crazy. "Are you going to do all that bending over you mentioned earlier?" "I don't know if I can do that. We'll see." The tension in her voice could be cut with a knife, but it seemed like she was also pretty excited too. "I think I've been in here long enough that the guys are getting worried. I should probably go out there." "Ok. I love you. Be careful Sharon. I'll be there as soon as I can, probably just before the end of the first half." "Love you," she replied and then the line went dead. I screeched into Jason's apartment lot at about 8:45. My initial "plan" was to be able to surprise them a little early since they didn't think I would get there until 10. But as I arrived I thought of another plan. Jason's apartment is garden level and with it being dark out, I realized they wouldn't be able to see me if I took a look in the windows. Yeah, a bit illegal, and I might freak out the neighbors, but I wanted to see what was happening. Plus, it was warm enough to hang out outside. I walked (ok, I snuck) around the side of the building. Fortunately, the back side had a courtyard with a bunch of trees, but I had to push through some bushes to get to the back of Jason's apartment. As I finally got through it was a relief to see that all of their lights were on, meaning it would be very difficult for them to see outside. Plus, several of the windows were open to let in the fresh air. What would I see? Heck, with the windows open, what would I hear? As I approached I could hear some type of machinery going and once I got to the window I could see Sharon vacuuming a bedroom. And she was right when we talked on the phone. The French Maid outfit was indeed a lot more revealing than the ones we had looked at before. With her high heels and the short skirt, half of her ass hung below the end of the skirt. And the g-string didn't hide much. At 5'7" and 125 pounds, she was still pretty damn tight. No cellulite. I had never watched her like this and I had to arrange my cock. When she bent over to pick up the power cord I just about shot a load right there. Her pussy lips were completely on display in the sheer outfit and it was clear that she was pretty excited. I couldn't believe there was nobody in the room with her, watching her work. But then she turned around and I thought I was busted until I noticed she was looking just to my right, in the corner just next to the window I was looking in. There was Jason, holding a beer and watching Sharon work. With her turn in my (our) direction I finally got the full view. Her top was so completely sheer that every bit of her was visible, and clearly turned on. Her nipples were extended as much as I've ever seen them. She clicked off the vacuum and I heard her ask what was next on the list. "It's five minutes to tipoff, let's go into the living room. You can start putting out." "The food. Right?" she finished for him. "yeah, put out the food. That's what I meant." They walked out of the room, Sharon in her very little clothing with her high heels, showing off just about everything. As they left the room I slid over about 10 feet so I could look into the living room where Pete was watching the pre-game show. The living room had a small couch, a recliner, and a decent sized coffee table, covered with the normal crap guys in their 20's own. Some sports magazines, a trinket from a trip to Cancun, and a bunch of remote controls. Jason and Sharon entered the room as Pete was tipping up the last of his beer. "Oh Sharon! This one is empty. I need another." Sharon sneered at Pete. He has never been one of her favorites. "So?" "Aren't you the maid today? Get me another beer." Sharon stared at Pete with more than a bit of anger. Did I mention that she doesn't like to be ordered around? Then she looked over at Jason and he nodded, indicating that she should indeed be delivering fresh drinks. I could see the resolve set in her face, and then she walked over to Pete to get the empty. He had put it on the coffee table so she walked over to it, turned her back to him and bent over to pick up the can. From my angle I couldn't really see what he saw, but it is pretty clear that he got an amazing view of her ass and pussy from about 12 inches away. Losing the Bet As she stood back up Pete suddenly reached forward and grabbed Sharon by the waist and pulled her so that she ended up sitting on his lap. Very quickly his hands were roving over Sharon's tits and she was doing nothing to stop him. Her eyes closed and her head tilted up as she leaned back against his chest. The empty beer can dropped from her fingers as she raised her arms over her head to give him better access to her breasts. With no reluctance to his advances, Pete's right hand drifted down to Sharon's pussy and started rubbing. This time she moaned and started to wiggle a little. After a few moments her eyes fluttered open and she jumped up and off his lap. "This isn't that kind of party" Sharon mumbled. At least that's what I thought I heard. She was pretty quiet as she stood there. Pete's groping had completely exposed her breasts and her nipples were poking strong. Her panties had been partially pulled to the side, and half her cunt was exposed as well. Jason, having watched all this, stepped behind Sharon and took his turn grabbing her waist. With her back to Jason and facing Pete she moaned again. Jason untied the skirt and it dropped to the floor. It wasn't doing much anyway since it had risen up to her hips. But now all she had on was a sheer bikini style top that was pulled down to expose her nipples, along with the sheer and very small g-string partially pulled to the side. She leaned back into Jason as with one hand he began caressing her left tit and with the other untying the top. Within seconds the top was loose and then it joined her skirt on the floor. Unable to just watch, Pete leaned forward and began messing with Sharon's g-string. I hadn't realized this before but there was some kind of quick release hook so rather than pulling them down they merely became unhooked and dropped to the floor. Honestly, I couldn't believe what I was seeing. There was my Sharon standing there stark naked, her back pressed against Jason as he ran his hands all over her; and Pete on his knees in front of her, his face inches from her pussy and his hands moving up her leg to the promised land. Soon, Pete had his fingers in her pussy as she spread her legs as much as she could while still standing. Sharon reached behind her and I watched as she began stroking Jason's cock through his pants. Within seconds, she had unzipped his pants and had her hand inside. His pants, freed from the support, dropped to the floor and he stepped out of them as Sharon tugged down on his boxers, freeing his cock. Sharon turned around to face Jason, his cock pressing against her mound as she rubbed and yanked at it. Pete stood up behind her and started taking his clothes off. Within seconds Sharon was standing naked with two naked guys. Rubbing one cock with her right hand and another cock with her left hand, Sharon looked completely lost in the moment. Jason took some control and pushed Sharon down to her knees where she became face to 2 cocks, one in each hand. I thought she was going to start sucking on them but Jason pushed her further down onto her back on the floor. She didn't let go of either cock, so both guys had to go down to their knees. Jason spread Sharon's legs and positioned himself between them. Sharon arched her back in preparation and yanked on his cock. I heard her scream clearly as Jason entered her and her body shook in an orgasm like no other. As I mentioned before, this wasn't really the plan but it was clear Sharon was out of her mind in lust. She was naked with two guys; one was pumping her as she continued an orgasm. She had the other's cock in her hand, yanking and pulling. I don't think I can adequately explain the conflict I felt. On the one hand, it was unsettling watching my wife getting fucked by not just one but two guys, especially since she didn't know I was around. This is cheating. On the other hand, this was the most amazing thing I had ever seen. I mean, I enjoy watching Sharon in the throes of passion when we are making love, but I've never seen her like that. Bucking and screaming while being lost in the moment. I can't think of any other term but amazing. Sharon's orgasm had to last for at least two minutes as I watched her going and going, her tits bouncing violently as Jason pumped her faster and faster. Finally, Jason roared as he blew his load and I heard Sharon scream one more time as it all crashed down. Her body went limp, and her hands dropped to the floor, ironically leaving Pete hanging in dismay. He must have been pretty close, because his face was all mashed up. Either that or Sharon had been yanking so hard that he was in real pain, which wouldn't bother me too much. Jason pulled his cock from Sharon as she gasped one last time and I saw that it was just drenched in her juices. Sharon worked her way into a seated position, her face flushed, and her chest even more flushed. "I can't move my legs" she said with a smile, looking at Jason's cock rather than his face. I'm not sure if she was more afraid of looking into his eyes or still enamored with his cock. I'm leaning toward the cock. With the activity seemingly over I thought it best to back away from the window and head back for the car. Once there I called her number and let her know I was about 5 minutes away and to have a beer ready for me. What happened next is the next chapter. Losing the Bet, Being the Wager For Leanne's birthday, my wife Debra wanted to do a dinner party at our house for Leanne, Sheri, and Jeni. The three women were all my wife's former college roommates from two years ago when they had rented an off campus apartment together for their senior year. Perhaps I should describe these women for you so you know how lucky I was every time I visited my then fiancé at her apartment. Starting with my wife Debra... Debra is 5'7 long legs, very nicely curved ass, she has long dark hair all the way to her sweet ass, and firm B sized breast that fit ever so perfectly in my palms, blue eyes and thick luscious lips that were truly 'cock sucking lips' if ever there were any. Leanne was 5'5 very lean, tight little ass, curly brown hair about shoulder length, pert little A sized breasts, chocolate brown eyes, and small lips that curled into a mischievous grin easily. Sheri was 5'3 but very athletic, muscular legs, abdomen, and ass. Her hair was red, straight and cut short; she had bright green eyes, B sized breasts that somehow always seemed larger, and a beautiful smile when she chose to, which had never been too often as she was more of the tough no nonsense type. Jeni was the tallest at 5'9, long blond hair nearly as long as my wife's, she had C sized breasts that she always showed off in cleavage revealing outfits, shapely legs, bright blue eyes, round ass, and a ready smile always on her full lips. My wife admitted back in school that if ever there was girl she wanted it was Jeni. Safe to say between the four of them you had nearly every type you could want if your interests were female. Also safe to say they were all out of my league, I am only 5'8 myself, medium brown hair that I wore long when they were in college, but I've had to cut short for my life as an 'adult'. I have a medium build and a goofy looking face and smile. Usually I was referred to as nice, or cute, never good-looking. But my wife seemed to find me attractive and who was I to complain. The girls all showed up together with bottles of wine each and after talking we sat to dinner. After dinner we sat and drank and talked and drank some more. Leanne said she needed to use the bathroom so she went to the downstairs one, and then Sheri asked to go so we told her to go to the one connected to my wife's and my bedroom. Sheri noticeably stumbled going up the stairs but she finally made it up. After Leanne had been back for several minutes I was beginning to wonder what was taking Sheri so long, I was worried she may have passed out or something. Then she came out of the bathroom and stood at the top of the stairs wearing next to nothing. " Hey check out my dick!" She yelled. She was wearing a strap-on I'd given my wife as a gag gift a year before. My wife always would get upset and say, 'suck my dick' and I'd say, 'you don't have one', so I had gotten her one. That was supposed to be in a locked box of toys in our bedroom. " Sheri! Go get you clothes on and put that back!" I yelled up the stairs a little upset that such a private thing was on display. " Why don't you make me?!" Sheri said lewdly stoking the purple cock that was the only thing she was wearing. Figuring I'd had less to drink then her I thought I could probably catch her and get her back into her clothes, so I charged up the stairs. Sheri ran ahead of me giggling as she ran into the master bedroom. I got to the doorway to see her jumping on the bed with her boobs and purple cock bouncing in front of her. I ran from the door towards the bed and dove to grab her. In a show of athletic ability that stunned me she bound out of the way and as I landed face first on the bed she landed on top of me. Faster than I could believe possible she handcuffed me to the bed with cuffs she had attached to the headboard, she then reached under me unbuckled my belt, unbuttoned my pants and yanked them and my boxers down and off my body, yanking my shoes and socks with them. Then I felt and heard my shirt being cut and then torn from my body. Here I was naked handcuffed to my bed by one of my wife's best friends. I tried to squirm free but she grabbed my left foot and cuffed it to the footboard, and then despite my struggles she did the same to my right. " Damn it David!" I heard my wife's voice from the doorway. " I didn't do this! She did it! Get me out of these!" I said frantically. " I can't do that because you just lost our bet." My wife said bringing herself into my view. " What bet?" I asked without comprehension. " I was saying I could get any guy in bed and naked." Sheri starts. " But then thinking of what a great guy you are, I bet she couldn't get you to." " And I bet against her." " I'm not willing to this." I said indignantly. " I would never cheat on my wife." " Well to be fair nothing in our bet said you had to be willing. She got you in bed and naked and that means she wins." Debra says. " Well what did you bet?" I ask, wondering how much money we would be out for this little bet. " You." Leanne says with a smile. " What do you mean?" " That I get to have you however I want you." Sheri says with a smile. " What?!" I ask in disbelief. " That was the deal." My wife agreed. " Try not to break him, oh and be good to Leanne to, it is her birthday." Leanne slowly started to strip out of her clothes and I could feel my cock get hard against the sheets. " What are you going to do to me?" I ask. " Something I've always wanted to try with a guy." Sheri said cryptically. " For now why don't you use the tongue Debra has told us so much about on Leanne, after all she is the birthday girl." Leanne climbed on the bed in front of me and lowered her pussy down in front of my face. I take one last glance at my wife to see Jeni's hand on one breast, and one hand lifting up my wife's skirt. I tentatively reach my tongue out and caress Leanne's outer lips. As I begin to let my tongue slide around another woman besides my wife's pussy for the first time since we had first begun dating I feel Sheri's lips kissing my ass cheeks. I slide my tongue along Leanne's inner folds as I feel Sheri's tongue trace the crack of my ass. Sheri's tongue inches close to my anus and then back up as my tongue circle's Leanne's hole. Then as I feel Sheri's tongue slide right over my anus I shiver and let out a surprised gasp. " I think he liked that!" Leanne says excitedly. " Then he'll love this." Sheri says. Suddenly I feel her tongue push against by anus and force its way into me. I buck back into her with a need I had never felt before. " Don't forget about me." Leanne says with a smile, and a gentle hand drawing my mouth back to her pussy. Needing no further urging I delve my tongue back within her folds as I enjoy this new sensation of having my ass tongued. In time with Sheri's tongue fucking my ass I begin to flick my tongue across Leanne's clit. Before long my moaning into her pussy is out done by her screams of orgasm as she pulls my head hard against her and she bucks her hips in to my face. " God he sounds good, I am going to have to try that later, but now..." Sheri says. Sheri moves around behind me a bit before I feel something cool pour down my ass crack. Then I feel Sheri's hand massaging the oil down my ass and then her finger teasing my anus. I continue lapping lightly at Leanne's sweet pussy as Sheri pushes her finger into my ass. I slowly lower my tongue so that I am tracing the path between Leanne's pussy and her anus. Leanne lifts her hips up to allow my tongue further access to her rear, and when Sheri adds a second finger to my ass I push my tongue into Leanne's. Leanne starts grinding herself against my nose as my tongue works her ass, and Sheri's two fingers work my ass as I buck back into them. Suddenly Sheri pulls her fingers out and Leanne lifts way from my face for a moment. Then Leanne slides beneath me and places the head of my cock at the entrance to her pussy. I glance again over at my wife and my cock seems to harden more as I see her in a sixty-nine position with Jeni. My attention is re-drawn to my position as I feel something larger than a finger press against my anus. It suddenly dawned on me what was going to happen. " Please don't." I whisper, " I'm a virgin back there." " Well you've taken pretty well to it so far." Sheri says whispering in my ear. " I'll be gentle, you just relax and enjoy." Suddenly I feel her pushing forward and I try to force myself to relax. Then without warning the head pops into my ass, and this forces my cock to bury itself halfway into Leanne's pussy. Leanne and Sheri both moan in unison, as I am half caught between the pain in my ass and the pleasure in my cock. After a moment's pause Sheri begins pushing forward, which at first only succeeds in pushing my cock deeper into Leanne's pussy. " God you are fucking huge!" Leanne exclaims with a gasp. When I finally bottom out Leanne lets out another low moan. Now with nowhere further for me to go, Sheri begins to continue the penetration of my ass. The pain had subsided and I just relaxed allowing myself to just take it for Sheri's pleasure until just as I feel her pressing against me I feel a twinge in my ass that sends a pure pulse of pleasure right through my cock. " Your hot ass just ate my entire cock in one try." Sheri says in a low sensual voice right at my ear as I feel her breasts pushed against my back. " How does it feel?" For moment I nod my head, " Feels good." I admit quietly. Sheri slowly pulls out and I just stay buried in Leanne unable to move. Then as Sheri pushes back forward I push back to meet her. " You fucking love it don't you?" Sheri asks. " I do." I admit. " I want to do this to you until we both cum." Sheri says quietly. As Sheri pulls back again I push forward into Leanne's pussy and she gasps deeply as I penetrate her. " God, you two are so fucking hot!" Leanne says excitedly. I could feel her pussy convulsing around my cock. I begin to pull out and Sheri pushes back into me causing both of us to moan together. Then I push forward and Leanne moans a little louder. Her tight pussy was squeezing my cock tighter than I could believe, it was like she was on a continuous orgasm. I slowly push back into Sheri and we both moan again forcing my cock to twitch in Leanne's pussy. " Tell me what you want ass slut." Sheri whispers in my ear. " Please fuck my ass." I beg knowing how she wanted me to respond. " Louder bitch, I want your wife to hear." " Please fuck my ass!" I say louder. Suddenly I hear Debra screaming her orgasm into Jeni's mouth and pussy. Slowly Leanne, Sheri, and I begin increasing our pace with me rocking between them. One moment I am filled with Sheri's rubber cock, the next I am filling Leanne with my fleshy one. I rock back and forth between them, each of them meeting me thrust for thrust and all of us rushing towards orgasm. Suddenly Leanne lets out an ear shattering scream and starts thrashing about on the bed beneath me. Her spasming pussy walls clench my cock tightly so that my cum boils from my balls, and travels up my cock. I bury myself deep into Leanne's pussy and yell my orgasm as my seed bursts out of me deep into Leanne. As my cock is shooting its first spurt Sheri forces herself down deep inside me and lets out a scream of orgasm as she rocks her body up and down against my ass with the rubber cock buried deep inside me. Almost unnoticed I hear two more excited moans as both Jeni and my wife cum into each others mouths spurred on by the three of us on the bed. For several minutes we lay there spent, with my cock buried in Leanne, and the strap-on buried in me. Then my wife and Jeni crawl on the bed with the three of us and Sheri slowly pulls out of my ass. Jeni, Debra, and Sheri uncuff me and I pull out of Leanne. The five of us crash together on the bed in exhausted sleep. Good thing my wife and I got the king size bed instead of the queen we had been thinking of at the store. I only hoped we wouldn't wake-up with hangovers and regrets, but hey, that was one hell of night we would never forget. Of that I was sure as I drifted off to happy sleep with four naked beautiful women surrounding me. Losing The Bet I had started on my third dick when someone behind me lifted me to my feet. Still bent over with a cock deep in my throat I felt a cock enter the fake pussy from behind, rubbing against my own stiff and imprisoned member through the latex. I came pretty soon with the strangeness of this new perverted feeling, shooting my load into the confining pocket. My knees buckled but I was held up by the two guys fucking me. I glanced across at Sharon. She was being taken from behind as well. The cock in her mouth pulled out after firing a wad down her throat. "Hey fella's we both have another hole you know?" She said to the queue. They took the hint. My pussy pummeller lay back, pulling me onto all fours. As yet another cock took its turn in my mouth I felt one entering the sheath in my ass. Now I was truly full. I took another look at Sharon. She had adopted a different position. She was lying on the guy in her butt and was being pounded in her cunt from above. As well as a dick in her mouth she had one in either hand too. The fellows waiting for me noticed that and I soon had a hot meat stick in both hands, keeping my balance with the shaft down my gullet. The two of us were screwed like that for over an hour, as each cock came it was replaced by another. We were both covered in cum and it dripped from our orifices. My own dick was almost continuously pumping out spunk as I enjoyed the feeling of being taken in the same way as my mistress. Eventually Sharon stood on wobbly legs and came over to me. She motioned for me to open my mouth. When I had, she dribbled the last cumload she had taken orally into my waiting maw. I came again. "Now for that ten inch dick up the ass I promised you." She smirked. My eyes widened as I saw this cock approaching; it was as long as my forearm and nearly as thick! "Get ready sweetie, here he comes!" The monster member eased into the slippery wet sheath in my ass. Further and further it sank into me until I thought I was going to break, and then it went in deeper until I felt his body against mine. It was all the way in! I had taken the whole ten inches up my anal passage. I grunted as he pulled back some, and then again as he thrust back in. "Oh god, that's good!" I breathed. "Fuck me! Fuck me hard! Shove that big boy into me." I cried. Sharon stood in front of me. "You're making too much noise. Lick me out." She grabbed my ears and pulled my mouth to her dripping pussy. I began to lick spunk from her as the huge dick in my ass began to really ream me. I made Sharon climax twice before the gigantic dong shot off, some of it going into my ass sheath, but most of it splashing the backs of my legs. I came one last time and collapsed to the floor. ------------------------------------------ I looked up panting and saw Jenny giving me a hard stare. "I want him back Sharon." She said. "What are you prepared to bet?" "Myself. If I can make you and him cum, I get him back. If I can't then I'll be yours as well." "Okay." Sharon smiled. "But you might have trouble getting him off. He's been cumming almost non-stop for an hour." "I want him back." Jenny stated flatly. "Okay then." Sharon shrugged. "Where do you want me?" "On all fours there." Jenny pointed and then looked at me. "Take that latex thing off." She commanded as she began to pull on a strap-on that was nearly the size of the cock I had just had in my butt. Sharon smiled in satisfaction as she saw the monster phallus. I eased the latex panties off, pulling the cum-filled sheath from my ass and releasing my softening cock from its prison. It was all wet and sticky from the cum I had been shooting into the pocket. "Stand over Susan." Jenny said. I obeyed. Jenny knelt behind Sharon and pushed the strap-on into her cunt. As she sank in, she pulled me towards her and enveloped my dick with her soft lips. Jenny began to rock her hips, fucking Sharon with the strap-on. At the same time she teased my now hardening prick with her tongue. Jenny's talented mouth always did this to me. Soon I was thrusting down her throat, determined to do my part. I came quickly, loosing my load over Sharon's butt cheeks. Jenny redoubled her efforts, half the bet complete. I knelt beside Sharon and started to massage her tits through the latex uniform. "Cum for me Sharon." I whispered. "You can always try and win me back next week." She smiled and then arched her back as her orgasm took her. Jenny stopped pumping, sitting back on her calves. I helped her to her feet. "Come along Mistress. I'm yours for the week. Maybe it'll be my turn to be slave master next week?" Jenny smiled tiredly. "Only if you stop fixing it so that you end up as a slave." She stopped and thought for a moment. "Maybe we should get Mena involved. I know you'd like to dominate her." My dick twitched at the thought. "See, he's interested. Sharon and I are running out of ways to humiliate you now. We need something new." "Get Mena and we'll see." I smiled.