I’ve been with my girlfriend since 2021 and things have been great. The usual ups and downs but nothing significant. I would say the only outstanding real big problem is that I want to cheat on her with an old friend with benefits that I had on and off again. Let’s call her Sasha.

I’ve known Sasha for over 10 years. We actually first met because I was hooking up with her sister. When that stopped, we kept talking and casually hanging out here and there. Nothing crazy, we lived near each other so we would just go on walks or hangout at the park.

The summer before I went to college, a few years after high school, we started getting closer and hanging out a lot more. Earlier in the summer, she had broken up with her first serious boyfriend after being together for about a year or so. Now when we hung out, the topic of conversation started to be about relationships and sex. As a horny twenty something year old, I welcomed it. She would talk about the stuff her and her ex would do and the stuff she wanted to do but that he didn’t.

Up until this point, I was never really attracted to Sasha like that. But something switched. Hearing her talk like that and seeing that side of her made me really attracted to her. Eventually, she ended up confessing that she had always had a crush on me. Right from the start I told her I didn’t feel that way about her, plus I was going to college soon and wouldn’t be able to see her anyway. I told her that, while I thought she was hot, I wasn’t interested in dating her. After a bit of bargaining, we ended up deciding that being friends with benefits could work.

Now when we hung out it was purely sexual. My parents owned a cottage and would spend a majority of their summer living there, while I had the house to myself. Sasha would come over, we’d hop in bed and make out, go down on each other, dry hump, everything but sex. I wasn’t too concerned because the other stuff was a lot of fun and I figured it was because she had only been with one other guy before, so I didn’t push it.

One night she was over, we had been naked and making out for what felt like an hour. I was ready to tell I had to cum when just before I could mention it, she told me she wanted to fuck. I asked her if she was sure and before I could finish asking she got on top of me and slipped it in. I had never seen a girl actually dripping fine shiny strands of fluid like she was. After her riding me for a bit, I stopped her and put on a condom and continued fucking her. I flipped her on her back and after a couple more deep thrusts I ended up finishing. She was moaning and squirming even after I pulled out.

Once we got all cleaned up and were laying in bed, she confessed to me that she had never actually had sex before and that I was first. As surprised as I was, it also made sense in the back of my head as I had a feeling. Just based on the amount of naked dry humping we did the first few weeks to her talking about sex more and then it finally happening. She told me that she had just said all the stuff she did before because she wanted me to think she was experienced, in case we ever hooked up.

Being a horny early twenty something year old I didn’t even complain. For the rest of the summer, we would just hang out and have sex. She would spend days over at my place, we would usually be naked and touching each other in some way. I should probably mention that Sasha is about 5’7, long brown hair, long tanned legs, and a toned stomach with amazing perky B or C cups. So I had a hard time keeping my hands off of her.

When the summer ended, we broke things off and went our separate ways. We kept in contact for a bit but I mostly got busy with meeting new people at school and classes. Throughout the time we would randomly message each other but nothing much beyond some casual walks down memory lane.

One of my last years of college, I secured an internship back in my hometown, where Sasha lived. By now I had been dating a girl I met in college and we were set to move in together in the fall. We were only a few hours away from each other for the summer, so nothing too unmanageable but still quite different when you’re used to hanging out almost every day and having sex multiple times a day.

One weekend during that summer, I had been in my living room when I saw Sasha walk by. This wasn’t too uncommon since she did live a few streets over, still, it was the first time I’d seen her in a few years. She looked incredible. She was sporting her usual summer look, denim short shorts and a white spaghetti strap tank top. All of it fitting her tanned toned body perfectly. I opened my front door and yelled her name. She came up to my house and we chatted before she said she was on her way to a friend’s house but that she would be walking back this way early in the evening and that she would stop in.