I took the girl in white to junior prom. She was a soph. She was my first kiss, my first of pretty much everything but sex (and obviously she didn’t have tits like that at the time - those joined much later). We ended on good terms when I moved schools.
Five years later we caught up via Tinder (I don’t have Facebook). I saw her and she looked familiar, except a whole lot more done up. Luckily she matched with me and I caught up with her on the app for a little while.
I only had sex with 2 women at the time that we were chatting, so I was excited that she was happy to write to me. We agreed to meet up. But I was nervous. She was much dorkier back then and I’m still pretty dorky now.
When we met up she wasn’t dressed quite like this, but not that far off - skintight dress that showed off a lot of leg and boob, plus high heels. We sat down at a restaurant and I felt like an imposter. And our conversation was awkward and forced.
Eventually we talked about sex, and she asked me how many girls I had been with - I told her 3 to sound a bit more experienced; but she laughed when she told me she had been with a LOT more than that….I was worried. And she probably would expect a lot more. We had nothing in common to talk about, and I knew I was fucking this up. But luckily she didn’t seem to care. She said she liked me when we were teenagers because I was so kind and nice. And she had mostly been with jerks for the last little while.
So I went home with her and even though I had had sex before, it was with girls who were equally inexperienced. She knew what she was doing. Foreplay was incredible, and the sex was like a whole different world. I was worried she wasn’t enjoying it, but she seemed to moan a lot, so I thought I was doing okay.
When I came it felt like I had never truly orgasmed before. She smiled, pulled off my condom, and lay beside me. She said something like “you’re not very good, but I always liked you in high school. I can teach you if you want but you’re buying me breakfast tomorrow.” So I slept over and we fucked again in the morning (with more guidance), went for breakfast, went back to her place to fuck again, and then she told me to go. I thought that was it but she called me a couple days later and came over to my place. She said I was improving, and was enjoying her time with me. I was surprised because she was sort of dull to talk to, and we didn’t have much to say to each other. But we basically kept up like that for a few weeks. She told me I was getting way better, and started having me go down on her for very long periods of time.
And then she asked me to meet her parents at a family wedding. I was flabbergasted, but I said okay. And so we went to this wedding and she told everyone I was her boyfriend, and I was so flattered. And then I realized why I was there. Her last boyfriend was hated by everyone - a big dumb meathead who treated her terribly. And when she brought him to the family, her dad threatened to cut her off from all her money. I talked to her about this and asked if it was true. She said “if it was, would you care?” And then I realized that no, I didn’t. The night of that wedding we had anal sex for the first time.
After that, she told me that we should still see each other for a bit, but that she might go back to an ex of hers, but if I could be a boyfriend when needed for family events, we would sleep together a bunch. I couldn’t complain. We only ended it three months ago when she got pregnant and begged me to be the pretend father and I just had to say no to that. We’ve still had sex a couple times since - she keeps trying to convince me. And to be honest, it is pretty tempting…