Adam Loses a Bet Ch. 07

"I did lose... guess you owe me a date," Amy flirted. Oooo that was exciting. After a few more minutes waiting on the floor, David returned. "Close your eyes," he instructed. We both obeyed as he began moving us around, positioning us for something. My feet brushed against Amy's nees while we maintained missionary position.

I heard him open the bottle of lube he had used yesterday and a small part of me got excited. He pulled down my panties and inserted a sloppy finger into me briefly, I still had cum dripping out of me, so very little lube was actually needed. Then I heard him slap some on Amy.

I felt a thick piece of silicon land on top of my butt, and confusion hit me. He had a perfectly functioning monster, why did he need a dildo. I heard Amy squeal as the cock was slowly pulled off me. "Lean back sissy," David calmly directed. His hand guided me back onto the fake penis until it slid into me, it was definitely big. "Open up," David demanded.

I opened my eyes and looked behind me at Amy. Her eyes were wide. Between me and her was a black, double sided dildo sitting snugly between each of our assholes. I realized what he wanted and looked up at him patiently. After a few tense moments, David gave us a nod of approval which gave us permission to start.

We were both hesitant, so it was a slow build-up. I fell onto the toy slowly, feeling it slowly push further into me. About 5 inches down I leaned forward, letting most of the insert fall out of me and consequently pulling it out of Amy. I immediately pushed back, trying to push it deeper into my partner in crime. She mimicked my movement and let out a muffled moan. "MMmmmm, it's so big." I cried.

"Push harder," Amy urged. Not about to let her down, I pulled back and plunged the insert as far back as I could. "Ooohhh," I heard her gasp. We both pulled out and plunged back down, easily taking 7 inches each. We picked up our pace, simultaneously getting fucked and fucking each other on every downstroke. "Oh.. ah.. Mmmm," I breathed, matching her passion with high pitched gasps.

I closed my eyes and focused on the feeling of bouncing and being filled up. I bit my lip and tried to go as deep as I could. Having taken David just yesterday, I was feeling confident in my ability. Speaking of which, he had removed his shorts and was now walking toward me silently.

Amy pushed the dildo deep into me and I couldn't help but let out a gasp. I then pulled out and we both buried silicon deep inside of us, consequently causing different feminine noises to escape our lips. We rinsed and repeated this cycle; pulling back only to squeal back onto the cock. I glanced backwards and saw Amy's butt jiggle with every repetition, responding to my own butt that bounced around like jello. We were both breathing hard. When I turned my head back around I ran into David's dick. It was right in front of me, he was kneeling at my head's level.

"UUGHh," I gasped. David saw my open mouth and took the opportunity to thrust into me. Nearly on instinct I started sucking him off, bobbing my head in tempo with Amy's assault from behind. My tongue swirled around the detail of his cock while I bucked and fell onto the dildo behind me. I couldn't scream, but I could moan hard into David's meat.

"Freak! This is so good," Amy cheered between squeaks. Amazingly, we started clapping cheeks, taking the full length of the toy. It hit deep, we screwed each other fast, and man were we in heat. David had put his hands on the back of my head and was ramming his dick into me, causing me to deep throat him as Amy plunged into me.

"UUUUuugGGHhH... Ooooohh... MMmmmmmmm... Aahh... ah. Ah. AH! Ah ah. MMMMMM!!" I couldn't tell which were mine and which were Amy's. Each gasp was separated by a different kind of slap. My ass would crash against Amy's and my chin would touch David's balls, filling my nostrils with his unique musk. "Fuck! Uh, AAh, AAAAAAAaaaaahhhh!!" I heard Amy climax. This sent me over the edge, I plunged onto a cock, inhaled, tasted, felt cock, and let myself explode from the sensation of being skewered from both sides.

Amy and I went limp. David held my head up while he face fucked me at lighting speed. Shortly, He climaxed into my mouth and I fell to the floor. I fell out of reality and dazed into nowhere. The taste of cum filled my mouth and over 9 inches of dildo stuffed me like a turkey. I was simply satisfied.

What would this mean tomorrow, when the bet was over. Would I return to being a normal guy? Would I ever get fucked again or was more tradition sex in my future? ... ...

Who knew. By the time I had woken up from afterglow David was dressed and making out with pantsless Amy. I slowly stood up and noticed I had made a mess on the floor. David must've noticed too, because he stopped kissing Amy to tell me to lick it all up.

I nodded and immediately fell to the ground to lap up my own cum. To my surprise, Amy joined me and licked up my seed with me. I guess we were both used to the flavor.

Once we finished we stood up straight and looked at David, waiting for his orders. I couldn't help but let out a foolishly big grin. David looked down at both of us and broke our hearts: "Get dressed, that's all for today."

I couldn't help but feel disappointed, but I was in too good of a mood to argue. "Hey, sis," Amy whispered.

"Hey what," I responded.

"You can take... you know... you can take IT out." Oh, I had completely forgotten I still had a double sided cock buried inside of me. I reached down and pulled out the silicon penis causing an audible 'Pop'. I then reached down to my feet and pulled up my panties, I still reveled in the feeling.

After we changed, Amy drove me home (picking up my baggy hoodie I had left, so I could sneak into my house). We made plans to meet up for dinner later and exchanged a tender goodbye kiss.

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Believe it or not, we did end up dating. Crazy right! The rest of the year was just as wild as that odd week. Every other weekend Amy and I would have a threesom... I mean have dinner with David. Dinner often took a few days and sometimes involved a random guest. However, once we graduated, David moved away and only visited for the next few Halloweens and Valentines. Amy and I made sure to make those days special😉.

Bryan did ask for a few more favors, which were very sexual, but he stopped soon and moved on. I guess I did too. I only really crossdressed for a few halloweens and for roleplay with Amy. We decided that my new female name would be Kayla, to avoid confusion, but after a few years we rarely used it.

I did enjoy being a reluctant sissy for a while, but in the end I found it time consuming and purely physical. I much preferred spending quality time with my girlfriend then dressing up to be something I'm not. Developing an intimate and emotional connection became my foremost priority and quickly overshadowed my early relationship lust. We grew close.

After a few years we were an unstoppable couple. I understood her and she understood me; we fell in love over and over. I guess that's why we ended up working so well together. I guess that's why I'm gonna marry her.

Her only requirement is that we wear matching underwear to the wedding.