Hello,
Last summer, I met a girl (we'll call her Ash) on a dating site for a hookup, and both of us were looking for FWB. The thing is: she was 23, just about to go to college as she didn't have the money before, and I was 31. She seemed to think it was kind of novel to hook up with an older guy though, so it worked out. And she was so damn cute, a little thing with a fiery personality.
We hooked up a few times toward the end of summer, and it was just an awesome, fun relationship. We had great banter back and forth, and I loved spending time with her. The only thing is: I never actually got to have full-on sex with her, just oral. I have pretty severe performance anxiety, so I can barely get my cock up as it is sometimes. She definitely wanted me to wear a condom, and that would just further deflate any half-erection I had going on. Once I've been seeing a girl for a while, it usually works out, and we probably would've ended up having sex if she had stayed.
Unfortunately Ash ended up going to college, which was only about an hour away, but it was still enough that we wouldn't really get to see each other much. Before she left, we had gone on things that were pretty close to actual dates. I wanted to try to ask her out for real, but I knew I was probably way too old for her, even though she was definitely into me at the time. And now I'm still kicking myself for it.
So Ash moves to her college, and she starts to share stuff about how she's experimenting with hooking up with other guys. We were super open with each other about our sexual encounters, although I had just one or two while she was having a typical crazy college experience. Even so, I wasn't particularly jealous, even though I had feelings for her. I mean, it was just sex with random guys, right?
The two of us were pretty close by that point even if a lot of our interaction was from phone calls. It was definitely more than FWB, and I got to visit her every once and a while on her campus, but she was really busy with her classes and all the extra activities she was involved in.
Then she starts to tell me about this frat guy she had met. Her first story about him involved her saying how hard it was to give him a blowjob because his cock was so thick. She said she had to practice on him more because it was really difficult, especially since he lasted so long. She sent me a funny gif of some porn where the guy came too early as a complete joke, but it got to me a little bit.
Ash and I kept talking, but she would share more about this frat guy (we'll call him Don). She said it was hard to get used to having sex with him because his cock was pretty big. I would check her Snapchat story every once and a while, and it would be her making a joke about how much she loved cock and how she was going to get railed for hours that night (she was very open about sex in general haha). She told me one night that Don and her had stopped using condoms and how exciting it was to her, even if she was on the pill.
Pretty soon after this, she would always be "too busy" for me to come see her. Class and her schedule would be too packed, although we would still talk on the phone fairly regularly about stuff that was happening. However, she had started to see Don pretty much every single night. She would stay up until 2-3 in the morning if he wanted to come over then. He would often come over drunk after a party, and he would fuck her for hours. But she was still too busy to see me.
I had started to develop feelings for her, but she had the same happen for Don. Even though he had repeatedly told her he didn't want anything serious, she was super into him. She would always say how she needed her daily fix of Don. And since she always had to tell me her latest sexual encounters, she let me know when she let Don come inside her for the first time, confiding in me that she was a little scared she might get pregnant because she had forgotten the pill.
Nowadays, we pretty much only text each other every once and a while. I know this isn't exactly cuckolding since we weren't in a relationship, but I fell for her, and she ended up with some asshole frat guy.
I guess that's pretty close. I still have a few pictures of her that I'll always keep. Here are a couple. Maybe I'll post again if something changes.
Jamie
