**Background:** This will be the first of **many** stories (if people enjoy them) involving me and my ex-girlfriend. She is *the* reason I developed a cuckold fetish and it only dawned on me recently as I’ve started to think about these stories.
I’ve always been on the shy side when it comes to dating. I met Nicole in 2nd grade and we were always close friends growing up. Of course I had a crush on her during this time and only got the nerve to ask her out during my senior year of highschool (over 10 years later). She said yes, which still shocks me to this day, and we dated for a little over a year.
Nicole is a total bombshell, petite blonde with boobs on the smaller side (~34B) but with a gorgeous butt. I’m about average height, but very skinny and have always struggled to put on muscle. She took my virginity and basically taught me everything I know about sex, which I admit is still not a lot. She wasn’t a virgin when we started dating and was very open sexually, willing to try almost anything. Our sex life was pretty vanilla for the entirety of our relationship. Although she was very sexual, she always had trouble cumming with me. I could get her to orgasm with a lot of effort by eating her out and using my fingers but always failed to get her to orgasm during sex. My penis is ~7 inches long but I always struggled to last a long time, even with a condom, which we used almost every time.
Anyways, being the dumbass that I am, I broke up with her before we went our separate ways to college because I “didn’t want to do long-distance”. I suggested that we stay friends and made an effort to keep our life-long friendship alive, even though we weren’t dating any more.
**First Cuckold-inspiring Experience:** As we rekindled our friendship, it was “natural” for us to have conversations involving sex. We never really went into too much detail at first but would mostly talk about whom we were dating and stuff of that nature. That is until she started telling me about her coworker, John. She was interning at some finance firm over the summer and working with a guy that she described as a former model.
We would catch up over the phone at least once a week and there was always an update on John during our calls. I didn’t mind talking to Nicole about him as I convinced myself that I was “over her”. John had broken up with his girlfriend earlier in the summer and was progressively becoming more flirty with Nicole while at work. This continued for several weeks.
**Juicy Parts**: I was at my apartment when I saw Nicole’s number popup on my phone, right on time for our weekly catch up calls. Before I even had the chance to say hello, she was yelling into the phone, “ahhhhhhhhh I did it!!”. The conversation went like this:
Me: You did what?
N: I hooked up with *him*!
Me: No way! Really?
N: Holy shit yes, I’m driving back home now but I’m still seeing stars. Ahhhhhh.
Me: Oh so you had sex with him? Already?
N: He invited me over and said that we could watch football together. He started making out with me and I couldn’t help myself. One thing led to another and then our clothes were off and we were having sex. And guess what?
Me: What?
*At this point, I had so many thoughts running through my head but I couldn’t help but get hard from hearing her talk about the experience. I’m somewhat ashamed to say that I sat down on the chair and pulled my penis out while she continued her story.*
N: He made me orgasm during sex for the first time!
Me: No way! You did?
N: Yeah he was fucking me from behind and I could feel this pressure building. He kept hitting the same spot over and over, and before I knew it I felt him pushing me over the edge. I lost my breath and honestly felt like I was going to pass out from how good it felt. He kept going and going though at the same pace before I felt myself cumming again. I’m legit still out of breath and red in the face and it’s been 15 minutes since I left.
Me: Holy shit that’s so intense, I’m so happy for you!
N: I still can’t believe it happened. We just connected and it just felt so good. He fucked me for over 30 minutes before he came. I need to go home and clean up haha.
Me: Clean up? Didn’t you make him wear a condom?
N: Well at first I did, but then he had trouble staying hard because of the condom. I told him he didn’t have to wear one so now his cum is leaking out of me as I drive home haha. Sorry if that’s TMI.
Me: Not at all… are you going to see him again?
*When she told me that his cum was still leaking out of her pussy as she drove home, I had trouble holding back and ended up cumming in my hand.*
N: Of course, that was legit the best sex I’ve ever had…
I don’t remember talking about much else on the call as I sat there with my cum dripping down my penis while talking to Nicole. I felt a strong sense of shame but also an even stronger sense of horniness after we hung up. I spent the rest of the day jerking off replaying that scenario in my head over and over while looking at a nude I had saved from when we dated. Thinking about how she came in doggy for the first time with this dude is easily one of the hottest moments I jerk to.
I have quite a few more stories that came after this if there’s interest in hearing more.
Source: reddit.com/r/gonewildstories/comments/oiazfl/how_i_developed_a_cuckold_fetish_with_my_ex_mf
Damn good story
Definitely interested in hearing more!