This happened to me a little while ago. It was my first cuckolding experience. My friend Shaun and I both consider ourselves straight but have had a quiet “bi-bro” sexual relationship for years. We’re pretty laid back when it comes to sex. We talk about it, share pictures/videos of our girlfriends fucking us. Shaun’s never been shy about sex or his manhood; he’s 8 inches and loves showing it off. I’ve probably seen Shaun’s cock just as much as my own. When we didn’t have girlfriends we’d “bro out” and use each other to get off.
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Shaun and I were hanging at his apartment. We were both kind of bored and scrolling on social media. The conversation got sexual, as it usually does with us. He asked me when the last time I jerked off was, and I said Jenn (my gf) blew me a few days prior, but I don’t remember the last time I jerked off. That was a lie, I had actually jerked off that morning, but I wanted to see where he was going w it. So I asked him how long it had been since he got off. He, too, said a few days ago, which I’m sure was a lie.
He pulled up some porn on his TV and we went back and forth looking at different categories of mostly straight porn. We really couldn’t agree on anything, but I suggested we try bi or gay porn.
We eventually found a gay porn w a BBC fucking a cute twink. We both took our underwear off and got settled onto the couch. Before he started the video he turned to me w a sinister grin and asked me if I wanted to make things interesting. I asked him what he had in mind and that’s when he said, “whichever one of us cums first has to give up their girlfriend to the winner.”
I chuckled, and asked what he meant by “giving up” Jenn. He said, if he won, he got to fuck Jen , and if I won, I got to fuck his girlfriend, Nicole (21). Not thinking for a moment he was serious I agreed, we shook on it, and started watching the porn. We both got hard together. I tried to dirty talk him and told him how hot it was to jerk off to a big black cock destroying a tight hole. We both put ourselves in the twink’s point of view and really fantasized about getting pounded by a BBC. This is when I knew I was in trouble. In my attempt of getting Shaun to cum first by dirty talking about the video, I was getting more aroused and could feel myself getting closer to blowing. I slowed down a bit, but eventually the slightest touch made me want to cum. I gave myself a final stroke and shot my load on my chest and stomach in shame. Shaun lasted about 30 more seconds and blew his load on him and me (he’s a big cummer).
We both laid naked w the video still playing coming down from our orgasms. He leaned forward to find his boxer briefs. As he put his underwear back on he said “a bet is a bet.” I honestly wasn’t sure if he was serious or just messing with me, but he assured me that this was a real bet. I was shocked because although we’ve jerked off over pictures and videos of each other’s girlfriends together, this was the first time he ever told me he wanted to fuck my girlfriend.
That evening I got back to my apartment, the dried cum of Shaun and I still on my chest as a reminder of what I was obligated to do. Jenn was in the living room and we chatted for a bit. She asked how being w Shaun was, I told her jokingly at first that I lost a bet and needed a favor. Naturally, she asked what bet. I filled her in to us jerking off, she knew we had done that in the past and wasn’t upset, but told her we made a bet that the loser has to give up their girlfriend to the winner if they cum first. I saw her eyebrow raise in a mix of bemusement, frustration, intrigue, and arousal. Although Jenn knows Shaun, she certainly never knew Shaun in that way. I explained the conditions, that Shaun got to do basically whatever he wanted and I have to accept it.
Shaun is very attractive, beautiful body and tight abs, nice tan skin, and a thick 8 inch cock that every girl used to fawn over in high school, so Jenn didn’t say no at first, but wanted to process everything. As we got ready for bed, we didn’t say much. Without any lead in Jenn just turned to me and said, “tell Shaun I’m in and I’m his.” I was honestly shocked, although Jenn and I are adventurous, sexually, I never thought she’d agree to be used like this. I was jealous and frustrated at her willingness, I felt betrayed, but also extremely aroused at the idea. After a little discussion w Jenn, I sent Shaun a text message that sealed our fates. I told Shaun “she’s yours.”
We set up that Friday evening to be the night it was going to happen. All afternoon was surreal to me, I watched as my girlfriend prepared her body for the inevitability of what was to come. She showered and shaved her legs and pubic hair in anticipation of getting my friend’s cock in her. She picked out a tight red dress and slutty panties, and all I could think about was that thong was going to be either around her ankle or tossed casually on the floor somewhere. Had I known this* is all what I agreed to, I probably would have thought about it more. Admittedly I was turned on, but also nervous. Jenn was my girlfriend and I love her, but watching her try on different underwear to be fucked in made me question the foundation of our relationship.
The time came, I drove Jenn to Shaun’s place; as we were driving, it was silent in the car but I did manage to thank her for doing this. She just said that next time make sure I won the bet. I tried to laugh and agree w her. I pulled into his driveway, we got out and walked to the door.
He opened it up and at first it was like nothing was wrong or different, he greeted me like he always did, and he was wearing jeans and a nice T-shirt. he invited us in and offered us drinks. Again, I thought this was so surreal, I expected him to be in a bathrob or more like a 70s porn star. For the first 5 minutes, nothing seemed out of the ordinary, I thought he might have chickened out or wanted to pretend the whole thing was forgiven…I was wrong.
Eventually he talked to me less and less and started talking to Jenn, and that’s when he asked if she knew why she was there. She said she knew. He expressed his appreciation to her, and then turned to me and said there’s something in the bathroom I would need, and he motioned his head as if to say, “check it out.” When I got into the bathroom, my heart sank, as I knew in an instant that how this night was going to go. Casually placed on the sink counter was a lock and a chastity cage waiting for me. I was no stranger to it. I accepted my fate, and took my pants and underwear off, I slowly put the cage around my cock and connected the lock to the cage. However the night was going to go, my cock was no longer part of the plan.
I slowly walked out back to the living room where Shaun was sitting next to Jenn getting more familiar w her. Jenn was the first to notice my “accessory,” and gave me those “I’m sorry for you” eyes, as if to say, ‘sorry, my cuck, but I can’t help you anymore.” Shaun turned to look back and had a big smile on his face, and simply said I looked good and that now we can have some fun. He took Jenn by the hand and walked her to the bedroom. I scanned the room and saw the evidence of his planning. On the night stand were dildos and vibrators, some of which he and I had used before, a couple of jeweled butt plugs of different sizes, and couple of sex towels, and just for me, my very own cuck chair at the side of the bed for me to watch.
He didn’t waste much time, he directed me to remove my shirt and become fully naked. I complied, he then said for the next hour or so, Jenn was not my girlfriend and he can do whatever he wants to her. Here was the kid I grew up with, played baseball and football with, got girls with, but it was as if I didn’t recognize him anymore, we had a different dynamic now. He told me my role was to sit quietly and watch as he made good on our bet. I sat on my chair and awaited what was next.
I’ll post Part 2 soon.
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