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The first girl I ever slept with, and my last relationship of any real substance. We were “in love” as only a high school couple can be, and she was a virgin too, which was a relief to me. Nine months after we started dating, we Did It. After I graduated, I moved in with her. Living together was surreal, and more than a little stressful. The sex was awkward, infrequent, and boring. We ended up making it to a year and a half before I broke it off. It was a clean break, and I’m happy to say we’re still friends.
Sarah could have been my first, and every time I realize that, I nearly weep with joy she wasn’t. She was an emotionally damaged, manipulative, drug-addled hot mess I had been friends with for years. There are not many girls I would “take back” if I could, but Sarah is on the very top of that list.
Vanessa was my first time having good sex, and mind-blowing, eyes-roll-back-good blowjobs. She was orally fixated, and she always swallowed. The one time we didn’t use a condom, she hopped off my dick to swallow my load when I told her I was going to blow. So far, that’s the only time that’s ever happened. We tried dating after we had been hooking up for awhile, but it didn’t work. I liked big words and she didn’t.
Sally was my next girlfriend, who I dated for maybe six months. She was Pentecostal, drug-free, and a little crazy. I met her while picking up a buddy from work. She later went through the employee phone list for my buddy’s number to bug him for my information. She was the first girl to cook me breakfast in the morning.
My sister’s longtime friend. We had known each other for a few years, and had taken Chemistry together in high school, where I flirted with her for a year. She was over at my place hanging out with my sister, and they had decided stay the night. I was courteous enough to let Molly sleep in my room, and it turns out we both had the same thing on our minds. It was explosive in the way that only sex backed by years of unspoken sexual tension can be.
I met Jenny at the student union. If I recall correctly, I saw her a few tables away and said, “Hey you, come over here so I can flirt with you a bit.” Later, we both got incredibly drunk at a party, and proceeded to make out in front of (and on top of) everybody. Rather than doing her in the bathroom, I decided to drive home near-black-out drunk to fuck her in my apartment with a condom (like a responsible adult). En route, her mother called, and she was drunk enough to give her mom my address. Soon after we got home and got into it, her mother arrived. After a lot of angry words and her mother slapping me, naked, in my own bed, they were gone. Her mother called me the next day to invite me over for dinner. I declined.
Gabby was the first girl to masturbate while I was inside her (which, to be honest, threw me off my already-tenuous rhythm). We would later go to a rave on Halloween, snort Ecstasy, smoke a joint, listen to Death Cab, and rediscover ourselves. We ended up fizzling out, though. She was dating another guy at the time, who she later ended up marrying. I think she made a pretty smart decision.
My first experience with an older woman. Jessica was twenty-five, I was nineteen or twenty at the time. She was a Jehovah’s Witness who thoroughly enjoyed strawberry daiquiris, stand-up comedy, and the word “thoroughly.” After we had sex for the first time, Jessica told her group of friends that I had a dick that “looked like a redwood getting pulled by two smart cars.”
Sadie was was a smoking-hot punk rock chick who was way cooler than I was. We went out for drinks a few times, and during our first night together, I got my first case of whiskey dick. I remember being embarrassed, and more than that, confused. She was ridiculously good-looking, she was sucking my dick like she owed me money, but nothing was happening. It made no sense. The next few days I went full creeper and sent her a relationship request on Facebook. I never heard back from her again, and I honestly cannot blame her in the least.
The lowest of my sexual lows. I was at a party when Nancy latched onto my side and just sort of hung out there for the rest of the night. I was drunker than I should have been, and when our friends jokingly shoved us inside the only bathroom in the apartment, I just sort of took that opportunity to see how far I could go. (All the way, as it turns out.) Nancy was the first girl I kept around just for sex, which made me feel like a bad person and even worse when I found out I was only her second. The only other girl on the “take back” list.
Gabby’s younger sister. The first time I had sex with her was also my first threesome. The third party was her boyfriend, who was going through a bi-curious phase. I was just going through a Sasha-curious phase, so I was a little surprised when I felt her boyfriend’s hand grab my cock and start stroking it. I played along, but I didn’t get much out of that part of the experience. Eventually, Nancy and another mutual guy friend found their way into the bedroom and the three-way turned into an awkward orgy. Sasha and I fooled around a few more times, and I eventually did ask her out, but nothing ever came of it.
My first true one-night-stand. She was possibly the most vocal girl I ever brought home, and I believe at one point I actually told her to just shut up. The morning after, I made up some story about work or my parents coming by to get her out of the house, and deliberately “forgot” to give her my number.
My first co-worker hookup. We worked at a gourmet taco joint, and got along pretty well. She invited me to a party she was throwing, along with a few other people from work. After the party wound down, we were both in her room. We must have had sex four or five times that night and the following morning. At one point, I pulled a “Simba” on her. (You come on their belly, dip your thumb in it, and wipe it on their forehead, a-la Rafiki and Simba in The Lion King.) I’m lucky she had a sense of humor, because looking back, that could have ended badly.
I showed up single to a Valentine’s Day party, as did she. We awkwardly made out, she passed out for a bit and I kept on partying. Eventually, she woke up and drove me back to her place where we had forgettable sex. She slept in her room and told me that I could sleep on the couch in the living room.
Tara had pink hair, an obsession with hula-hooping, and an ass you could bounce a quarter off. By this point in time, I was getting a little tired of casual sex and I was looking for a relationship. Tara and I got along well enough, and the sexual chemistry was there, so I decided to see if I could start dating her. Unfortunately, I really had no idea what I was doing and I ended up scaring her off. The entire affair lasted a month, maybe.
Spring break, South Padre Island, 2012. Out at a club, I caught eyes with a cute Asian chick dancing by herself. I made my way over, smiled, and started dancing with her. Maybe ten minutes later, we made our way to the bar, did two shots of cheap vodka, and left for the condo I was staying at. She might have been the easiest pickup I’ve ever had, but the flip-side of that coin is that I was more than likely her easiest, too.
The quintessential party girl. I knew Ariel through mutual friends. The hookups were always memorable; once, it was in a million-dollar mansion she was house-sitting. Another time, it was when we were alone in my apartment, decompressing after wandering around in the woods on ‘shrooms all day. She was definitely one of the more stable female relations I’ve had in my life.
The first part of a one-two punch that made me reconsider how I was living my sex life. Kathy and I had been friends for a little over a year. After a night of drinking, I passed out at her house. When I woke up in the morning, we started cuddling and then making out. A day or two later, we hooked up, and I told her I was more interested in a relationship than just fooling around. A few days after that, she was avoiding me like the plague. It hurt, and even though she told me that she was still interested in being friends, I cut her out of my life.
The girl that got me to reconsider what I was doing with the women in my life. Marsha was my neighbor. I was riding my bike home when I noticed her struggling with her bike in the parking lot. I stopped to help her, and that was that. We started riding, going to bars, and hooking up with each other on a regular basis. The last night we had sex, the condom broke and I went out to go get her some Plan B and Whataburger. The next morning, she texted me that she liked me as more than just a hookup, and I ran for the hills. I realized later that I had done to Marsha what Kathy did to me, and decided to take a break from having sex.
By far the most convoluted, dramatic, and short-lived relationship I’ve had romantically. Over the course of two months, we went from seeing each other almost every day, hand-holding, and having explosive sex, to backpedaling into a platonic friendship and having Serious Conversations every week. I did my best to be a friend, but ultimately I felt like I was just being pushed away. It left me feeling like a cheap emotional crutch, and by the time it ended I was relieved that it had. I miss her smile, and I wish it had worked on some level.