I slept with my best friend’s lesbian step sister at his wedding [MF]

I was 27 when this happened (so, 10 years ago). I flew out to San Diego for my high school best friend’s wedding. We’re from NY, but he went to grad school out there, met his now wife, and stayed. I’m pretty sure I was the only one from our high school friend group who went, there were a few other college/grad school friends, but it was mostly family other than that. Oh, also my high school principal, who happened to also be best friends with my friend’s father, but that’s not important, just funny.

The only other person from my high school who was there was Lizzie (name changed). She was 2 years younger than us in school, and she happened to ride the same bus as me. I think my friend introduced us when she was starting her freshman year because their parents were dating, and eventually got married. Lizzie and I would talk a lot on the bus, especially since we were both very active with after school activities (she was a cheerleader… yes, really, I’m not making that up haha), so we’d both end up on the late bus together a lot. We never really hung out outside of school, other than the few times I went to my friend’s dad’s house to hang out. Even then, we’d usually just say hi, and then we’d kind of go do our own things. But on the bus rides, we were actually pretty close and would talk about a lot of different things.

I’m not even sure if I really thought about the fact that she would be at the wedding, but when I saw her at the welcome party, it was wonderful! I don’t think I had seen her since I graduated, so we were very excited to catch up. Fast forward to the day of the wedding. We were all staying in the hotel where the reception was being held for a few days. So, we all went to the hotel bar for an after party. I had bought my friend a special craft beer that was east coast based, so not super available on the west coast at the time, but I managed to find a pack. We were going to try it together to celebrate his wedding, but he understandable got very busy, then very drunk, and called it a night early. So I just settled in with everyone at the bar.

Lizzie and I were hanging out at the hotel bar. We’re still talking and catching up a lot, and she asks me if I want to take a walk with her around the hotel. I never had a crush on her necessarily, but she was definitely cute. Bright blonde hair, piercing blue eyes, freckles, medium height, beautiful and friendly smile. She was shy and fairly quiet, normally, but very easy to talk to. I didn’t really think much of it when she asked me to go for a walk. I think she said she wanted to see where the indoor pool or the gym was or something. So we went to find it. After we are a good distance away from the party, she turns to me and says she has something she wants to tell me. Now I’m starting to wonder, what is going on here? Is she flirting with me or going to admit feelings or something? That would be very unexpected. She says “I’m a lesbian.” I laugh and I think I said something like “oh wow, good for you!” meaning, good for her for coming out. She was relieved that I was so supportive. She goes on to tell me she had only just recently come out to her immediate family, and so not a lot of people knew. But she felt comfortable telling me and wanted me to know. That felt really nice to know that she trusted me like that.

We make our way back to the bar. We keep drinking, and get a little more wild. At some point, I tell Lizzie about the special beer I had gotten for my friend, but now he’s in bed and is leaving early in the morning so we missed our chance. And I can’t bring them back with me on the plane, so they’re going to go to waste. This was my concern, haha. All of a sudden, her face shifts. She looks at me, very serious. There’s something else in her eyes that I’ve never seen in her before, but I can’t quite recognize it, I think because of our previous conversation. And she says “I’ll drink it with you!” I excitedly agree, and we go back to my room.

We get there, and I pull out the two bottles from my mini fridge and she sits near me on the bed. Then I look at the bottles and realize they are not twist offs. She asks what’s wrong and I tell her I don’t have a bottle opener, I totally forgot about that part. Stupid on my part. Or so I thought. She says to me “well, now what are we going to do…?” I responded that I didn’t know, in all seriousness, and still totally flustered and embarrassed that I couldn’t get the beers opened. When all of a sudden, she jumps up and kisses me. Just starts going at it, some of the most passionate kisses ever. I was completely shocked. This girl who just came out to me as a lesbian, is now making out with me as if we were long lost lovers.

We collapse on to the bed and she starts unbuttoning my shirt furiously and ripping my clothes off. I asked her if she was sure about this, and she looks me dead in the eye and goes “oh yes, I’m absolutely sure.” I had never ever seen her like this before. She was always the quiet, meek, well-mannered type, and all of a sudden I saw this animalistic, sex-crazed look on her. She was in a totally different state, and it was incredible. She took total control. After getting all of our clothes off, she jumped on top of me and slid my cock right into her. We fucked uncontrollably for a while, her riding on top of me the whole time. I’m sure someone had to have heard us in the hallway, but I really hope they didn’t haha. I wasn’t thinking about that at the time, though. I was only thinking about this amazing experience with my quiet, beautiful high school friend. It was absolutely one of the best nights of sex I’ve ever had.

After we finished (luckily I had brought condoms with me for the trip… you certainly never know who you might meet at a wedding! Lol), she laid down next to me and we just stayed there for a few minutes. I think this along with a few minutes of a short nap sobered her up a lot, because suddenly she seemed back to herself, and she was a bit flustered and embarrassed, and she quickly got dressed and left my room very suddenly. It was a very sudden change and I was kind of confused. Because of this, I didn’t know what to say to her the next day, so we spent a somewhat awkward day with the rest of the friends we had been hanging out with all weekend, before flying back home the day after. I always wish we had talked about it, because we only lived about an hour away from each other, and I wanted to go visit her in her city when we got back home. I had her number, but I never called. But at least I’ll always have that memory.

Source: reddit.com/r/gonewildstories/comments/x9zk7d/i_slept_with_my_best_friends_lesbian_step_sister