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Allie
I had just turned 17 when I lost my virginity to Allie. We had dated earlier in my junior year, and this was one of those horribly awkward relationships where she had hooked up with half of our social circle. The kind of thing that could only work in high school. She was a year older and “experienced.” The deed was done in my parents’ basement and the experience turned out to be more ostensible than actual. We fucked again a year later and she still seemed to think that sex consisted of lying prone and little else. At the time I remember telling a friend that I didn’t get what the big deal about sex was. My attitude: at least it was out of the way.
Susie 1.0
Susie and I met my first night of college and ended up dating for two years. We were in an orientation group together, hung out for the day and ended up going out just the two of us and getting sloshed that evening. This was Canada and we could drink at 18 — neither of us had a clue about proper bar etiquette. I think I tipped the bartender 25 cents on a pitcher. Somehow this didn’t dissuade her (or she didn’t notice) — we made out the first night, and sex followed a month or so later. She forever spoiled me with a love of swallowing. Despite significant turbulence in the time we dated, sex was never the problem.
Elizabeth
Elizabeth was a close friend from high school who I had always harbored something of a crush on. She was also Amy’s erstwhile roommate and best friend. While I was still with Susie, we got drunk at my parents’ house and I declared that I thought I’d be happier with her. She initially objected then jumped all in. Her double D’s on a tiny Asian frame constituted my most exciting sexual experience to date. I felt guilty and stopped halfway through, but not before I left fingerprint bruises on her breasts. I overcame my guilt and fucked her properly a few weeks later, though I came far more quickly than normal and she was left rather disappointed.
Susie 2.0
While on another break with Susie 1.0, I found Susie 2.0. I had a class with her roommates, and they ended up at my house for a party. She had supposedly had sex before, but bled all over my sheets. My roommates saw everything when I washed my sheets in the morning. In hindsight, a gentleman (or non-19 year old) would have been a bit more discrete on this front. The sex was never very good, though she tried. I broke it off once Susie 1.0 took me back. I think I used AIM.
Tracy
Tracy was close friends with Susie 2.0, though we got to know each other through class. She was 4 foot 10 with some extremely perky C-cups and a slightly lazy eye that I was able to look past. We hooked up for a few days before she graduated, and she finally agreed to fuck me on her last night. She wanted to see my face while I fucked her, which I was fine with given how ridiculously perky her tits were. There was an unfortunate fascination with leopard print, but we did long distance pretty happily for six months or so.
Kelly
Kelly and I had a lot of friends in common and she was crushing hard for months. I had an informal thing going with Tracy and wasn’t really interested, but one night we ended up smoking pot at my apartment with some friends and everyone else left. I didn’t really have sex on the menu, especially when she told me she was on her period, but she took my “That’s okay” to mean “Okay, I’ll have sex with you” rather than the “No big deal” that I meant it to be. It didn’t happen again, perhaps because of the blood.
Kay
I’m shocked that I remember Kay’s name. I was backpacking through Laos at 22 and testing out a new technique some ridiculously sleazy womanizers had told me in Bali: “just stare at her until she goes for it.” She was Australian and happened to be sitting at the same table of some backpacker bar as I was. We started making out and I asked if she wanted to get out of there, at which point she said, “Let me just tell my uncle.” Things went downhill from there, as I’d been drinking for about six hours and the sex was sloppy at best. Afterwards I asked what her deal was and if she went to university, she responded, “I’m only 17. What is it that you Yanks call it, jail bait?” We didn’t stay in touch.
Laura
Laura was probably the only time I’ve ever felt raped. We were at my high school reunion and she had apparently been harboring a crush for years. Dumpy looking and a bit chubby, I had no interest. She tackled me repeatedly as I tried to walk back to my room and after losing my sunglasses I eventually gave in. We both agreed never to mention it to anyone, and I certainly haven’t.
Grace
I went to Korea to teach kindergarten after graduating college, and Grace was my first manager. Ten years my senior, she asked me to go out to dinner with her and her friends with some trumped up reason about apologizing for something that happened months before. Dinner with friends was actually dinner with friends, but after a few drinks she let it out that she wanted to fuck. She hadn’t slept with a non-Korean before, and jumped to the other side of the love motel bed upon seeing my decidedly average sized dick. We slept together a few more times, but it petered out due to cultural and age difference (and likely because the novelty wore off for her). I don’t think she was married, but she might have been.
So-Young
I’ve dated crazy girls, but So-Young was the craziest. Still in Korea, we met at a club with my opening line being, “Do you speak English?” Our first date was on Valentine’s Day and I said we should kiss and she responded by saying we should have sex (which we promptly did). She was not a fan of protection, and told me to take the condom off the first time we fucked. She was down for anything, and to date constitutes my only anal experience, drunken and lubeless, one that she understandably regretted. Eventually her craziness overwhelmed my 23-year-old libido and I broke it off. She kept showing up at my house drunk to give me head until I moved and she couldn’t find me.
Sun-Sil
Sun-Sil was a coworker and we initially flirted over kindergartners’ coloring books. She had killer curves, something her countrymen generally don’t appreciate, and wasn’t used to attention. I drunkenly kissed her when out with some coworkers one night, immediately realizing that she had almost no experience. It turned out that she had never had a boyfriend and had only had sex once. Painfully shy, to this day she is the only girl who has tried to hide her tits while I fucked her, a habit she thankfully got over. We dated for two years and broke up when I eventually decided to move back to the States. I still regret not figuring out a way to stay with her.
Gretchen
This one I’m not proud of. Gretchen was a Korean American coworker at my kindergarten while I was still with Sun-Sil. Her attraction to me was immediate. We lived in the same building and she showed up at my door after having a few and asked to look at my eyes. Being sober and committed, the better angels of my judgment didn’t let her in the apartment. Unfortunately, I drank those better angels into a stupor a few nights later and we fucked like crazy the night before a field trip. Our physical attraction was unstoppable and our attraction was like a drug, addictive to the point that we couldn’t stop no matter how many times we talked about doing so. She was the opposite of Sun-Sil in terms of experience, and enjoyed giving head more than anyone else I’ve been with. We were finally able to get our shit together and stop hooking up, mostly because she threatened to tell Sun-Sil if we didn’t. We still talk regularly.
Gretchen 2.0
Once again repeating names: now back in the States, Gretchen was a couch surfer who stayed with me in Charlotte along with her two little brothers and a few friends. They were all super religious and I really didn’t expect anything to happen, but she made her interest quite clear and I made a move. She seemed inexperienced in the one night stand but quite experienced in the act itself. She was sad the next morning. We haven’t seen each other since.
Alice
Alice was 18 to my 27, half-Korean and half-Pakistani with D-cups, a college girl working part-time at my company. Technically my subordinate, I was in a very long dry spell and she flirted with me for months. We got drunk at a party at my house and she ended up cheating on her teenage boyfriend with me. She was down for anything, experienced enough to be fun but inexperienced enough that I could still play the experienced mentor. Our hangout sessions mostly involved smoking weed and fucking. I realized I had to break it off when she threw up in my bed after a night of moderate drinking. Work was awkward at first, but we still get along.
