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This guy copped my virginity, but it was uneventful. I was a “late bloomer” and lost it to him when I was 19. Honestly, I don’t really count it because it lasted for all of three or four minutes once and we never tried it again. He was really sweet, but there was no chemistry and it hurt when he put it in me. This is where the phrase “just the tip” comes from, even though I still think it’s bullshit.
He came within like five thrusts inside of me the first time we had sex. He was a guy who went to my university, came over late one night and had sex with me on my couch. We became each other’s booty calls, even though he was terrible at foreplay (seriously, cut your fingernails.) I broke things off before I left for the holidays because he decided to randomly start choking me in the middle of sex. I also might have ruined his self esteem by asking him, “Is it in yet?”
We were both new to the city, and he was really cute and kinda goofy. I ended up going home with him and basically did everything but have sex. (We tried, but I was still inexperienced, and we didn’t have lube.) This was a great learning experience for me as I learned about his foot fetish on the first date. I also learned I was allergic to cats when I woke up to his cat on my now red, swollen half-face.
I didn’t really understand what “making love” was until I had sex with Alex. I wasn’t even in love with him, but the majority of my sexual encounters before him were super casual and I didn’t like any of them. While he wasn’t my first, he sure felt like it. I knew I liked him because I made him wait for a month to have sex. (And we also had to have that awkward “what is this” talk.) For the first couple of months, we had sex all the time, non-stop. We couldn’t keep our hands off each other once we had sex. I opened myself up sexually with him. I learned how to give great head, squirted for the first time, and had anal (which previously, was a dealbreaker.) Unfortunately, it didn’t end well. At the end of the day, sex was the only thing that kept us together (because we fucking hated each other.)
After I broke up with my ex, I went on an online dating binge and met this very sweet, very cute Cornell graduate. He was very traditional in the way that he didn’t kiss me until the second date, and then asked me if he could kiss me. He was not a very good kisser. He also had a kind of small and skinny dick, which didn’t bode well for either of us. We had sex once, and I asked him if it was in yet. ( I should probably stop asking men that.) He was very vanilla in bed, and it was over in ten minutes. The best part of this very short fling was when I gave him a blowjob on my birthday and made him come in under five minutes. He deemed me the “best blowjob he’s ever had.” Life got in the way, and he broke things off via Facebook, but we weren’t serious anyway.
Oh, fuck this dude and his gigantic dick. They’re both going to haunt me for the rest of my life. Brendan is the second best sex I’ve had in my life, but first if we subtract all the “casual encounters.” We met online, weren’t able to meet in person due to his clinical rotation schedule, but talked nonstop for about a month until we actually met up. You know that stupid Taylor Swift song “I Knew You Were Trouble?” That’s exactly how I felt about this dude, and I didn’t hide it.
Right before I moved, I ended up meeting this guy online and we hit it off. We didn’t have too much in common, but shared sexual chemistry. Naturally, we had sex and a lot of it. A lot of guys previously didn’t like eating me out — but he relished it and went at it with full force. I think at some point it could have teetered towards more, but I was going off on an extended trip and foreseeably moving out of the city, so we decided it would be a “Friends with Benefits” situation. He was just as kinky as I was, and he actually introduced me to the wonders of safe BDSM practices. It got a little iffy at the end when I mentioned I might end up staying in the city “if I didn’t get into any other programs,” and he offhandedly said that “maybe we could pick this up where we left off when I get back.” It sort of freaked me out, and I think it freaked him out too. We tried meeting up a lot after that, but the timing never really worked out too well. Bummer though, he was really cool.
Met him online, and by far the best sex I’ve ever had in my life. He was the first in a string of European encounters. I think I was so emboldened by the experience that in the process, I forgot to tell him my name. He gave me shit for it when he saw it on my laptop, and we had a pretty good rapport. We ended up having intense, athletic, mind-shattering sex that left us both drenched in each other’s sweat. He ended up telling me I was the “77th girl he had sex with,” and proceeded to tell me about his little black book. He was pretty interesting, and I think under any other circumstances, we would have hit it off well.
He invited me to his tiny flat in a pretty nice neighbourhood of Paris. He was tall, charming, and kind of a stoner. He was good in bed, but pretty selfish as he stopped after he came. He made me pizza, and we smoked a little. I sucked his dick, because he was “too tired to go again,” and then I left his place.
A little bit of me fell in love with this guy. I think it’s because he agreed to have period sex with me. I had just started, but he was down to come around and have sex with me anyway. Unfortunately, it wasn’t too great because he had a dick that curved downwards, and we couldn’t really get it to fit inside of me comfortably. After having sex, maybe three or four times, we just spent the rest of the night talking, cuddling, laughing, and making out a lot. I actually went back to Paris to hang out with him much later in my trip, but by that time, he had actually started dating a girl he really liked (that he met before he hooked up with me.) We kept in touch and were friends until I found out he was a sizeist pig. Cool.
We met up while on my very short, spontaneous trip to his city. He didn’t really strike me as a one-night stand kind of guy as he wined and dined me without making a move (even though I could tell he wanted to.) At eleven years my senior, he is the oldest guy I’ve been with. The sex was gentle and tender, which is sort of weird, because I’m pretty kinky. After our encounter, we kept in touch and became close friends — honestly, one of the weirdest ways I’ve made a friend, but one of the greater friendships I’ve had over the years.
Met him at a jazz jam session in Berlin on my last night and scrambled all over the city (near the hostel I was staying at) for a private room to retire to. We had sex in a private room at another hostel/hotel nearby. It was a waste of time, and we weren’t really that into each other, but he did provide some great conversation.
All I can say about this is: ew. I regret the night we shared, though it made me realize that I probably should stop with the one-night stands.