My ex GF (Jenn) and I dated for 4 years. She was a freshman and I was a sophomore when we met. A mutual friend introduced us when I was on a break with my GF at the time. We hooked up for about 2 months, but I decided to get back with my GF. Jenn was crushed when I told her I was getting back with my GF, and was very angry at me. Jenn and I really liked each other, but I still had real feelings for my GF at the time and thought I needed to give it another shot with her.
After getting back with my GF, Jenn and I stopped talking, but I would often see her when I went out. Many times when I would run into her at a bar, she would intentionally try to make me jealous. She would purposely flirt and hookup with guys in front of me. She would often make eye contact with me from across the bar, and made sure that I was watching as she approached another guy or left the bar with him. This drove me wild and turned me on so much.
My GF and I broke up at the start of my senior year. During the middle of my senior year, Jenn and I reconnected and started dating. During the first couple of months of dating, Jenn apologized for purposely trying to make me jealous by flirting and hooking up with guys in front of me. She said that she had really liked me, and that I really hurt her because all she really wanted was to be with me. She said she was being really immature, and wanted to get back at me. I had always had cuckold and humiliation fantasies, and wanted to tell her how much this turned me on, but I was scared about what she would say or think.
After I had graduated, I would go back to see Jenn 1-2x a month. One time I was there, I was pretty drunk and confessed how much it turned me thinking about her with other guys and how much it turned me on when she used to hook up with guys in front of me. When I told her this, she was embarrassed, and felt bad that she did that. She said she didn’t ever really want any of those guys, and did it just to make me upset. She said all she ever wanted was me. I tried to explain it to her and that it actually turned me on and wasn’t trying to trick her or test her. She would say I don’t want anyone else, I only want you. I kept bringing it up and teasing her anytime she went out about how many guys were flirting with her and stuff like that. Over time I kept pushing it, and opening up more to her about my fantasies and desires. She said that while it doesn’t really turn her on, if it made me happy, she would be open to roleplaying it occasionally.
It started off by her telling me stories about her and the guys she used to hook up with in front of me. When she graduated, and moved to the same city as me, our roleplay escalated pretty quickly. I started to really open up to her about my submissive side, and go deeper into my desires. Over the next couple of years, she became more open to them, and even started bringing them up herself. The cuckolding and humiliation roleplaying quickly started to dominate our sex life. When we first started roleplaying, it felt like she was faking it or just making up stories to get me off. However, now things were different, and I could tell that she wasn’t holding back and was being serious about everything she said. Even when she said she just wanted to have vanilla sex, she would often tease me and lightly humiliate me. Outside the bedroom, she started to become more dominant, and treat me differently.
About a year and a half ago, I told Jenn how badly I wanted to be her cuckold in real life. I told her that I know that I am unable to satisfy her, and that she deserves to be with a man who can give her the sexual satisfaction she needs. I asked if she wanted to take the cuckolding from fantasy to reality. Jenn didn’t think I was being serious, and said that she doesn’t believe I would actually want it in real life. I tried to tell her that I really do want it and that it would be great for both of us, but she didn’t believe it. She said she didn’t even really like the fantasy, and that she was mainly doing it for me and only wanted to be with me. She said it’s weird that I even have the fantasy. I was so confused because it was clear that she did enjoy the idea of me being a cuckold, and I know how much she missed being dominated. We stopped roleplaying it for about about 3 months, and went back to just having vanilla sex. However, our sex life wasn’t the same, and went from having sex 3-4x a week to 1x a week.
Right around the same time I asked to make it a reality, Jenn started a new job, and became very close with one of her co-workers. They started hanging out 1-2x a week, and Jenn became part of her co-workers college friend group. I didn’t really like this girl as she seemed very fake, and was very much about being “seen” and concerned with her image. I was invited to do stuff with them in the beginning, but would turn them down. So over time, I stopped being invited, but Jenn enjoyed hanging out with her and I was happy that she had made friends at her new job.
As she hung out with her more, Jenn started to become friends with this girls best guy friend. Let’s call him Matt. Matt is a very attractive guy, and your typical alpha male. When I realized how close Jenn and Matt had become, my cuckold fantasies started to take over. After not roleplaying cuckolding for about 4 months, I started to bring it up in the bedroom again, and slowly started to introduce him into the roleplay until he was the center of our sex life. She absolutely loved it. She had never been as into my cuckolding and humiliation fantasies as she was now.
I started to move the cuckolding from fantasy to reality by encouraging her explore her attraction to him and flirting with him whenever they were together. At first she was hesitant, but was unable to resist. She would come back and tell me about their night and the sexual tension between them. After about 2 months of him being the center of our sex life, I suggested making our fantasy a reality with him. This time she was much more open to the idea. However, she was worried about how it would affect her relationship with her co-worker, and what people would say if they found out. She just didn’t think it would be possible, and was also still worried that I wouldn’t be able to handle it in real life.
Over the next 6 months, Jenn grew very close with Matt, and our relationship started to go down hill. They started hanging out alone, and doing things together. Jenn would often choose hanging out with her friends and him over me. Our sex life now completely revolved around him and her. She stopped letting me have sex with her, and insisted on me fucking her with a strap on. She started treating me a like the beta cuckold I had always wanted to be both in and out of the bedroom. It was awesome, but I started to realize I was losing her. I love her so much and thought I was going to marry her. In Feb, I said to her that I felt we had grown apart and that our relationship has become all about cuckolding. I said I felt like everything revolved around her and Matt, and that maybe we should take a step back and focus on us. She agreed and apologized. She stopped hanging out with him alone, and hung out with those friends less. We tried really had to work on us, but things never got back to how they were. I could tell she was unhappy.
In May, she said she thought it was best if we broke up. She said that she loves me, but isn’t 100% sure about us and she needs to see what else is out there. I was devastated, and begged her to not give up and to work it out. She said that she’s really sorry, but that she’s just trying to do what she thinks is best for her. I was devastated and knew that this was all my fault. In September, I found out Matt and Jenn started dating. I was so hurt, but so turned on. I can’t stop thinking about them together and how she made me the biggest cuckold. Would love to discuss and share more of how she cucked me.
Source: reddit.com/r/gonewildstories/comments/qmsdfn/mf_how_i_lost_my_gf_to_cuckolding