The Bet - A Sissy Story by Jen Anders

The Bet - A Sissy Story by Jen AndersThis is a work of fiction. Any similarity to real persons, places or events is strictly incidental.My name is Dave and until recently I was a normal college student. That means broke, trying to date (unsuccessfully), and loved to party. My roommate, John, was just like me except that he had a girlfriend, Amy. One day we were in my room and discussing grades. ?Dude,? John said, ?you?re not gonna get any better than a C in economics if you don?t start studying more.? ?Please, that class is so easy I can?t get any worse than a B even if I don?t study.? I replied. ?Prove it.? he said. ?Ooh, I think we may have a bet. I want in. What are the stakes?? I thought it over, ?$100. Who ever gets the best grade in Econ wins and he other two have to pay up to the winner.? ?Dude, I don?t have any money for betting.? John complained. Amy?s the one that came up with the solution. ?Whoever wins makes the other two do something outrageous, like run across campus naked or something.? Now this was interesting! ?OK, John, what do you want?? ?Hmm, I want you two to be my personal servants for a week. Laundry, cooking, everything.? Amy and I agreed. My turn. ?I am so going to enjoy this. You two have to wear each others clothes to class for a day.? Amy agreed instantly. John was hesitant but figured it was a safe bet and relented. ?No dresses, just normal clothes. Right?? ?Sure, no problem.? Amy is the one who really got outrageous. ?WHEN I win, you two will enter the drag show at Lucky?s (a local gay bar). And if you win, I get half of any money you make.? John and I immediately refused, but we gave in when Amy said, ?What, afraid of losing to me? What wimps!?That semester I studied harder in Econ than any other class and was well on my way to getting an A. Until the final that is. I don?t know what happened but I blew it. I ended up missing an A by 1%. John got an A. 91%. I could live with that. What really got to me though was Amy?s grade. 97%. John and I had lost! Amy came trotting up with a smile on her face. ?Time to pay up boys!? John and I tried to get out of it but Amy wouldn?t hear of it. ?A bet?s a bet, assholes. I would?ve paid up, so you have to.? She was right. ?This Saturday night guys. Be ready to get dressed up.Saturday came and Amy showed up with bags full of clothes and her makeup. She instructed up to go to the bathroom and handed us each a bottle of hair remover. ?No hairy legs tonight. And no chest hair or back hair. In fact, lose it all below the neck.? John and I took turns in the shower. I went first. The hair remover kinda burned a little, but soon I was completely hairless from the neck down. To be honest, it felt really neat. When we were done we wrapped towels around ourselves and went to the living room. Amy then sat us down and laid out the rest of the stuff we would need. Makeup, press-on nails, and 2 wigs. A blonde, for me and a brunette for John. ?You first Dave. She took me to the bedroom and after an hour and a half Amy proclaimed me ready. She had even plucked my eyebrows. ?Your clothes are on the bed. Put all of it on and wait here. I?ll call you when John?s ready.I opened the bag and pulled out a slinky black mini-dress, black 4? patent leather heels, seamed stockings, and a corset with garters ad matching thong panties. The panties were just tight enough to pull my cock in and keep any telltale bulges hidden. I couldn?t get the corset fastened so I called Amy in to help. She cinched me up tight and kinda smiled a little as she eyed me, but said nothing. I slid the stockings up my smooth legs and I started getting a little thrill from the way the silk hugged them. I fastened them to the garters, making sure the seams were straight. I noticed there were some pads for the bra and stuffed them in the cups. I stepped into the dress and only managed to get it zipped partway up. I didn?t want to interrupt Amy again so I put the shoes on and was surprised they fit perfectly. Amy must have special ordered them just for me. I practiced walking around in them and wished I had a mirror so I could see myself.An hour later Amy called me in to the other room. I told her I needed her to zip me up. She came in and paused when she saw me and gave me a funny look. After I was zipped I was led into the living room and stopped dead in my tracks. ?John?? He turned and my jaw dropped. Holy shit! He was HOT! ?I can?t believe it?s you.? He was dressed in the same outfit as I was only in red. ?No shit! You look? great! If I didn?t know you were the only one in there I would?ve sworn Amy pulled a fast one on me and brought out another girl.? ?Well boys, I mean ?girls?, Care to see yourselves?? She led us into John?s bedroom and to the mirrored closet doors. John was right! I did look like a girl. And I WAS hot! Hell, if I saw myself at a party I?d even hit on me. OK girls, tonight you are ?Devine? and ?Joanna? And you?ll be lip syncing to ?Girls Just Wanna Have Fun? by Cindi Lauper. We have some work to do on your performance. Let?s get cracking. We practiced for the next hour until Amy pronounced us ready. ?Let?s go girls.? That?s he it hit me. I had to go out in public like this. I was scared shitless. What if my neighbors saw me? Luckily, we made it to the car without being seen.Once at Lucky?s Amy entered us in the Amateur division, which had a $200 Grand prize. We sat around nervously waiting our turn and sipping on rum and cokes to build up our courage. Luckily we were near the end of the show and were feeling a pretty good buzz. Our names were called and we were a hit. The crowd went nuts. We didn?t win, but we got second place, for $100. Not bad. Amy ran up and gave us both a huge hug. ?You two were great!? We spent the rest of the night drinking some of our winnings and I even danced with a couple of guys. To be honest, I didn?t want the evening to end. The club eventually had last call so we left and went home. On the way I noticed that Amy and John were whispering and giggling a lot and glancing at me occasionally.Once we got home John excused himself to the bathroom. Amy got me a beer and sat next to me. ?You were really good tonight. A lot of the guys were checking you out. And so were a lot of the girls. I know I was.? That?s when she put her hand on my leg. ?Uhh? what?? Then she kissed me. I pulled back at first, but soon melted into her and kissed her back. She slid her hand up my skirt and rubbed my cock through my panties. That?s when John came back in. ?I see you started already.? Amy smiled and whispered to me ?John and I want you to join us in bed tonight. What do you say?? All I could do is nod. She took my hand and led me back to John?s bedroom. She unzipped me and told me to keep my corset, stockings, and shoes on. John also stripped and took my hand. ?Lie down and let Amy get started.? John instructed. Amy pulled my cock out of my panties and crawled on top of me into a 69. She sucked my raging hard on into her mouth and I pulled her panties aside and rove my tongue into her dripping snatch. I was really getting into it when John knelt over my head and pushed his cock into her cunt. I kept licking her and occasionally licked johns cock. I was really getting into this. At one point John?s prick fell out of Amy?s pussy and I seized the chance to suck her juices off it. God, it was fantastic! The hard throbbing of his cock and the taste of Amy?s pussy made my head spin. Amy chose that point to climb off and let John suck on me. Somehow I had ended up sucking my roommate in a 69! What a night.I was beginning to wonder where Amy had gone when the bed shook and she climbed up between John?s legs. She was wearing a huge strap-on! What the fuck. She lubed John up and slid right in. Apparently they had done this before because John just sighed around my cock and sucked a little harder. That was it. I came so hard John couldn?t swallow fast enough and it ran down his chin. Amy pulled out of his ass and John moved back to kiss me. I pulled him to me and tasted my come on his lips and tongue. Amy wiped of the strap on and asked if I was ready. I knew what she meant and was willing to try. I got on my knees and felt the cool lube on my ass as she worked a couple fingers in. After a minute she put her tool there and I felt the pressure as she tried to force it in. I didn?t think it would go, but the head popped in. I gasped as my ass relaxed. She slowly worked it in using short, slow strokes. Soon she was all the way in and she began fully fucking me. John sat in front of me and I eagerly swallowed his cock. Amy was fucking me harder and harder and I sucked John like I would die if I didn?t. Soon Amy was ramming me so hard the strap-on was banging her clit and making her come. My cock was hard as a rock again and then John began to buck. I swallowed all I could and kept sucking until he was completely spent. I had a problem now. I was hard as stone and needed relief. I pulled John to me and slid my cock into his ass. I had his knees over my shoulders and was fucking him like crazy. He was yelling, ?Fuck my ass, baby. Fuck it! Come in me. Make me your lezzy slut!? I came then, filling his ass with come and kissing him deeply. Amy sat on the edge of the bed and said, ?That was fucking beautiful.? I collapsed in John?s arms and kissed his neck. ?Too bad we don?t have anything to remember this night by.? I mumbled. ?But we do!? Amy exclaimed. Lucky?s taped your performance and John set up a video camera in the closet while we were in the living room.? That night we fucked in all the positions imaginable. I even got to fuck Amy in the ass and her sweet little cunt.John, Amy and I still live together and we have made many more videos since. John and I have a huge wardrobe and still do the show at Lucky?s on Saturdays. In fact I have helped pay for college with my winnings. All because of a silly bet.