Sasha/Sasha's Boyfriend
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.

Jamie?
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.

Velma
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.

Hattie
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
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.

Sung
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.

Ariel
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.

Kathy
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.

Marsha
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.

Kim
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.