"As the evening wound down, she looked me in the eye and told me that I was going home…"
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In the span of twelve hours, I managed to have my first kiss and my first sex. Erin and I had met online a few months prior, through a mutual teenage interest in poetry. Soon, emailing turned into daily phone calls and declarations of love. We finally met in person under the guise of going to visit colleges, but instead of spending the night in the dorms with my hosts, I stayed in Erin's bed. The first time we had sex, which was the first for both of us, was awkward but not terrible. No one cried, no one freaked out, and we went back for more. Erin and I carried on for a year and half until I finally moved to her town. She promptly dumped me for a girl.
I was extremely intimidated by Justine when we met. She was the cool girl who I couldn't believe would in turn find me cool. Our first date involved taking the train into the city and going out to the beach, except since we were in Northern California, nothing about the beach screamed warmth and sunshine. I was too scared to kiss her on the train, but despite my lily-livered tendencies, we made it work. She was extremely inexperienced in bed, and part of the reason she was attracted to me was that she thought I could teach her. But at my age, I didn't have much to teach. I loved her pale skin and her Wayne Gretzky nose.
I cheated on Justine with Erin. From the onset, they both pretended to like each other but actually hated each other, probably because each of them sensed that I liked the other. I was too young (and not open enough) for a polyamorous relationship, so I just tried to suppress my feelings and desires for the other person. Eventually, Erin and I went out for a fancy lunch to celebrate the anniversary of our friendship. We ended up fucking in my concrete dorm room post-lunch. She helped me move months later and we fucked as the U.S. soccer team hammered South Africa on the television in the background.
I cheated on Erin with Justine. By this point, Erin and I were together again in an official capacity. In addition, Justine had moved to my town and didn't really know anyone, so we hung out a lot. The first sign of things going wrong was when Erin and I hosted a dinner party and she caught Justine and me kissing in the bathroom. She chalked it up to drunkenness, but sadly, that wasn't the end of it. I would walk over to Justine's apartment under the guise of hanging out and we'd end up sleeping together. The most vivid memory I have of the sex during this period is the time that I jerked off onto her beautiful feet.
Eventually, Erin snooped through my emails while I was out of town, greeted me at the gate at the airport and told me that she knew everything. We actually had our hottest sex that afternoon, both of us a complete mess of contradictory feelings: anger, lust, sadness, hate, desire and disgust.
Things got good again between me and Erin, for a while. Being naive and in our early twenties, we kept saying that we would end up getting married. But I doubt that either of us truly believed it.
I met Amy at a party where I showed up alone, knowing only two or three people there. I was nervous, so I ended up drinking a ton. While I was in line for the bathroom (for about the sixth time in the evening), Amy was waiting behind me in line and told me she'd kiss me if I let her go in front of her. I duly obliged and we ended up drunkenly making out in front of the house. I vomited at the bus stop, went home and stupidly posted about it online, only to have Erin read what I wrote. Erin and I broke up the next day during my lunch break at my mall retail job. Amy and I kept seeing other, taking walks around the block when she was on a break at work. I liked her because she went out and knew cool people and listened to '60s soul records. It all seemed very glamourous and exciting. I remember masturbating in front of her in an attempt to get her to have sex with me and we eventually did. We dated for a while, and I foolishly professed my love for her. Things ended badly, with me dumping her over the phone and telling her that I could never love her as much as I loved Erin.
The one and only time I was ever truly picked up. Fiona was a beautiful, tall modern dancer with dark hair. We met for the first (and last) time at a mutual friend's birthday party, which eventually devolved into a semi-ironic game of spin-the-bottle. Our in-game kisses were on the long side, and as the evening wound down, she looked me in the eye and told me that I was going home. We walked back to her place, a converted church, and had sex utilizing the pull-out method, but only after I waited naked in her bed as she smoked a bowl. She left me with tons of hickeys, and I rode the bus home the next morning wearing the birthday girl's paper crown. I was too young to appreciate her and the whole situation. I incorrectly assumed that my adult life would be like this from that point on out.
Suzanne was a friend from the East Coast who I visited while on winter break from college. The whole weekend was a dumb game of will-we-or-won't-we, which eventually culminated in fucking in a guest bedroom with all the lights off. This is the only time I've slept with someone and never actually seen their sexual parts. She's now happily married and we're Facebook friends but never interact with each other.
I intrigued her because we knew a lot of the same people. For a while, my friends all had an inside joke about my penis, which got her wondering exactly who I was. This, of course, lead her to… well, my penis.
Caroline was a sweet, quiet girl who went to an all-girls' college, but was also the most assertive and naturally kinky girl I've slept with. She claimed to watch porn constantly and had a thing for two men being together. If we'd been together longer, I might have indulged her in that, but the closest we got was some anal play. We broke up when I got bored and decided I needed someone a little louder and less mousy. I've never heard from or about her since.
Sarah was the end of an insanely long dry spell. She was with some mutual friends at the bar one night and I joined them for a drink or two. I thought she was cute and then thought she was awesome when she revealed that she also loved Guided By Voices. I promptly went home and asked her out online, and we had our first date the next week. The night ended with us making out at the bar (drunkenly, of course) and then returning to my place to fuck three times in the span of eight hours. It prompted my new roommate (who heard everything) to ask another roommate, "Is this guy always like this?" Sadly, the answer to that question was "no." Sarah and I met up one more time, but only after she called me up to let me know she didn't want to date. We watched City of God in my bed, seated apart and not touching.
I first became aware of Rachel's existence when I walked into my roommate's room one night, looked at a photograph on her bookshelf, and asked "Who's your cute friend?" We eventually met when Rachel came to town for a weekend. I spent the whole night teasing her about how much her city sucked, but it was obvious to us and everyone else around that we had a very natural chemistry. After hopping bars for a while, we found ourselves on my bed listening to Jin's "Learn Chinese" as she said, "If we do this, you have to promise it won't be awkward the next time we see each other." I agreed, and we slept together twice that night. My heart broke a little when she asked me if her breasts were big enough — her ex thought they weren't.
I wish things had been simple with Rachel, but they weren't. We carried on sleeping with each other over the next few months whenever we found ourselves in the same city. But eventually I liked her more than she could handle having come out of a long relationship prior to meeting me. The end was bad: I went home early from work because I couldn't stop crying, and for a while, I hated her guts.
We never slept together again, but until her recent marriage, the sexual tension between us was off the charts whenever we saw each other. Sadly, one of us was always in a relationship, so we were never able to revisit the past, even though I'm convinced that it would be very good as a one-off. I'm pleased to say that we are close friends now.
I was a disaster post-Rachel and was flattered when Casey, a hip ex-model, showed interest in me. She told me she was flattered that someone like me would spend the length of a party chatting her up. I gave her a ride home and then texted her to say that we should be in the same room at that moment and not in separate homes. We had what I deemed a three-night stand, although she really put me off when our photobooth pictures became her new profile picture. She's also the only woman who's ever sexted me; she told me to "come over and fuck me," but I politely declined. Ultimately, she liked me a bit too much, which was good comeuppance coming out of my situation with Rachel.
Audrey was an acquaintance's ex-girlfriend who I met at his birthday party. We hit it off immediately, and I liked her big blue eyes and curly brown hair. I gave her my number and left the party feeling great, only to feel dumber and dumber as the days and weeks passed without a peep from her. I had forgotten her when she left me a voicemail months later, saying that she was sorry for not getting in touch as her father had passed away shortly after we met.
We went out for drinks and made out heavily in my car afterwards. Our second date consisted of spending most of the afternoon and evening fucking in her insanely messy and disorganised apartment. I eventually realized that she had severe mental issues that I couldn't deal with, and the last time we slept together was an unmitigated disaster where we would fuck for a little bit and then she'd tell me we needed to stop… only to then request that we carry on five minutes later. This repeated itself for the whole night in my tiny twin bed.
We met online and even before we met in person, we had a great rapport going via messages and email. Our first date went spectacularly and within a week, she was my girlfriend. We held out on fucking for about an additional week and by the time we finally did, I told her I loved her during the act.
We were together for three years and the sex was quite good, although I could not keep up with her libido. She used to cry when I would turn her down after a long day at work but eventually that stopped. She moved to Asia to teach English and our sex life picked up due to the distance and time apart, but eventually it fell off again. She ended up dumping me via email, telling me that we didn't "quiver to the same music."
Oh God. By far the worst sex of my life. If I could strike one name off this list, it would be her. Thankfully, she lives overseas.