Straight Male / 29
Interesting Cuckold Story
Just want to share my (on-going) cuckold story, also my first ever experience.
So I've had this friend since college who a few years ago started transition (female to male). Early last year he got engaged to his long-time girlfriend (who I've always thought was hot as hell) and for some reason all three of us started hanging out a lot more once COVID started to settle down a bit here. There had been a few times in the past where my friend and I had hung out, gotten fucked up, and had discussed some of our kinks and what not. He had mentioned multiple times that he had this kink of watching his (now fiancé) girlfriend get fucked by a cis man and take a real dick. He told me his fiancé had never been with a cis-man before (she was always a lesbian before he started transitioning). anyway, he wasn't sure she'd be down to do something like that.
So back in October, they both approached me one night when we were hanging out and asked if I would potentially be down to do something like that. I was taken aback at first because A. I didn't think his fiancé would want to and B. I didn't realize they would ask me lol. Anyway, we planned to do something but I ended up getting COVID and our plans got pushed back two months. So in early December we finally linked up. The first cuckold experience was obviously kind of awkward since none of us had done anything like it before. His fiancé was very cautious of me and it took us a long time to finally get into it. But once we did... damn it was hot as hell. His fiancé was definitely enjoying taking my dick, and my buddy was sitting on the side of the bed watching the whole time. I thought maybe he would end up being uncomfortable seeing his fiancé enjoy it, but he seemed chill. She also made it a point to talk to him frequently, making sure he was okay with it. After she sucked my dick and I ate her out, we did missionary and then gentle buckshots, which we both came from. After we were done, they both said they'd be down to do it again.
The next two times were even better, as she was more comfortable with me and we got more positions in. She even took initiative to get on top and ride me, and let me take full control of her after that. We even got way more intimate with kissing and touching, and she wasn't even talking to my buddy at this point, not even making eye contact or checking in with him like she had before.
This last time was craaaazy though. When I got there, she asked both me and her fiancé if we'd be okay if I were to fuck her raw without a condom, and just pull out to cum. I should've known at that moment what was going to happen. Anyway, I was okay with it because she is on birth control, but my buddy seemed really cautious and uncomfortable at first. But he finally agreed and we got to it as normal. But this time was even more intense, and I could definitely feel the energy in the room shift with my buddy. I'm gonna be honest, we both kind of forgot he was in the room, as we were getting so into it and just fucking the shit out of each other. The last position, she was on top of me. As I felt myself about to bust, I told her. She kept going and said it was fine. I tried to hold back, and told her again that I needed to pull out to cum. I saw my buddy stand up from and shoot bullets at me with his eyes. But she kept going even harder, verbally begging me to cum inside of her. I couldn't resist when she said that, and I shot my load in her, and watch as it dripped out when she got off of me.
Needless to say my buddy was PISSED and started cussing both of us out. I apologized a few times and ended up leaving because I felt bad. Obviously it wasn't my intention to cause a riff between him and his fiancé, but there was a definitely chemistry between her and I that we couldn't resist in the moment.
I haven't heard from my friend since, but have texted with his fiancé a few times. And she's mentioned now questioning her sexuality and wanting to continue a sexual relationship with me. What did I get myself into?! lol not sure where to go from here...
So I've had this friend since college who a few years ago started transition (female to male). Early last year he got engaged to his long-time girlfriend (who I've always thought was hot as hell) and for some reason all three of us started hanging out a lot more once COVID started to settle down a bit here. There had been a few times in the past where my friend and I had hung out, gotten fucked up, and had discussed some of our kinks and what not. He had mentioned multiple times that he had this kink of watching his (now fiancé) girlfriend get fucked by a cis man and take a real dick. He told me his fiancé had never been with a cis-man before (she was always a lesbian before he started transitioning). anyway, he wasn't sure she'd be down to do something like that.
So back in October, they both approached me one night when we were hanging out and asked if I would potentially be down to do something like that. I was taken aback at first because A. I didn't think his fiancé would want to and B. I didn't realize they would ask me lol. Anyway, we planned to do something but I ended up getting COVID and our plans got pushed back two months. So in early December we finally linked up. The first cuckold experience was obviously kind of awkward since none of us had done anything like it before. His fiancé was very cautious of me and it took us a long time to finally get into it. But once we did... damn it was hot as hell. His fiancé was definitely enjoying taking my dick, and my buddy was sitting on the side of the bed watching the whole time. I thought maybe he would end up being uncomfortable seeing his fiancé enjoy it, but he seemed chill. She also made it a point to talk to him frequently, making sure he was okay with it. After she sucked my dick and I ate her out, we did missionary and then gentle buckshots, which we both came from. After we were done, they both said they'd be down to do it again.
The next two times were even better, as she was more comfortable with me and we got more positions in. She even took initiative to get on top and ride me, and let me take full control of her after that. We even got way more intimate with kissing and touching, and she wasn't even talking to my buddy at this point, not even making eye contact or checking in with him like she had before.
This last time was craaaazy though. When I got there, she asked both me and her fiancé if we'd be okay if I were to fuck her raw without a condom, and just pull out to cum. I should've known at that moment what was going to happen. Anyway, I was okay with it because she is on birth control, but my buddy seemed really cautious and uncomfortable at first. But he finally agreed and we got to it as normal. But this time was even more intense, and I could definitely feel the energy in the room shift with my buddy. I'm gonna be honest, we both kind of forgot he was in the room, as we were getting so into it and just fucking the shit out of each other. The last position, she was on top of me. As I felt myself about to bust, I told her. She kept going and said it was fine. I tried to hold back, and told her again that I needed to pull out to cum. I saw my buddy stand up from and shoot bullets at me with his eyes. But she kept going even harder, verbally begging me to cum inside of her. I couldn't resist when she said that, and I shot my load in her, and watch as it dripped out when she got off of me.
Needless to say my buddy was PISSED and started cussing both of us out. I apologized a few times and ended up leaving because I felt bad. Obviously it wasn't my intention to cause a riff between him and his fiancé, but there was a definitely chemistry between her and I that we couldn't resist in the moment.
I haven't heard from my friend since, but have texted with his fiancé a few times. And she's mentioned now questioning her sexuality and wanting to continue a sexual relationship with me. What did I get myself into?! lol not sure where to go from here...
- That's Juicy! 24
- Remove It! 4
