Sex Lives chronicles the evolution of one person's sex life. This week: Aaron, 31, Boulder, CO.
I tried to lose my virginity as a junior in high school to a friend of mine from band who was like, “Oh, yeah, you know you’ve never had sex; we can have sex this weekend.” My parents found out and were not happy. They had checked my Myspace messages where we were planning it and I got grounded for like five months or something like that. My parents—my dad in particular—were very strict. He was raised Catholic and went to the seminary and has had one girlfriend his whole life. I had a real issue separating sex from feelings for a long time, because I was raised to believe that sex was a thing women did for guys when they got married and not thing that both people like to do. To this day, I have issues integrating the relationship side and the sexual side of things into the same person.
The first time I hooked up with a girl was the first week of freshman year of college when everyone's like 18 and horny and they're away from their parents. I was like, “I'm not gonna lie to you, I’m a virgin,” and she was like, “Cool. I’m not going to take your virginity,” and that happened like two or three times throughout freshman year.
February of freshman year I went to a party and drank a bit and smoked a bit of weed and hung out with this girl Kelly and we went back to her dorm room and I didn’t tell her I was a virgin. I lasted for about 12 seconds and pretended that I hadn’t come because I thought that if I lasted for only 12 seconds, she would know I was a virgin. So I just kind of humped around ineffectually until my dick went soft. And then she told me that she was used to guys with bigger dicks than that.
In college, I got back together with an ex-girlfriend from high school during the summer between sophomore and junior year. That was the first time I was having fairly consistent sex, the first time not having sex at like 2am in a twin XL bed, first time having sex that didn’t involve alcohol, probably. She was Miss Teen Washington at the time or something so I was like her delinquent friend. We would hang out and smoke Swisher Sweets in the park because she usually had to be the model of restraint because she was a pageant girl. The two of us hung out with her best friend the whole summer. We would go to her best friend’s lake house and her friend would go to bed and we’d go to the guest room and hook up, or we’d leave her best friend at the fire and we’d go have sex. One of our last weekends, we toasted with shitty blueberry vodka and Lindsey, her friend looked me in the eye and was like, “To wherever the night takes us.”
Later, my girlfriend was outside and I asked Lindsey, like, “Am I being a moron or were you saying ‘Let’s have a threesome?’” And she was like, “Yeah, I was saying let’s have a threesome.” I was like, you can convince her of that; I’m not going to ask to hook up with her best friend. So Lindsey went outside to have a conversation with her and came back in and was like, “She’s down,” and immediately started making out with me. And then my girlfriend opened the door and was like, “What the fuck you asshole?!” and threw her cigar at me. But I get it, like of course she blames me instead of her best friend since she was two. I’ve never talked to either of them since.
The second time I failed at a threesome, I didn’t really realize. I was with a girl named Christine, the second girl I ever slept with, and it was at a party and she was a friend of my friend Caitlin, who—looking back—had a crush on me. We went to this party and Caitlin was just feeding me rum and Cokes. And I was in the guest bedroom making out with Christine—like my hand is up her skirt—and Caitlin is just sitting on the bed talking to us. No one else is in there. Caitlin is sitting talking to us and at one point she reached behind her and started playing with Christine’s hair and I was like, in my head, “Caitlin, can you please leave I’m trying to have sex?” It took me years to realize, “Oh my god, you absolute dumbass.”
The worst sexual experience I’ve ever had was on a first date. Several years ago, I went out with this girl to a speakeasy, we were being very flirty, we went to a beer hall afterwards, we were making out, making a lot of suggestive comments and I had taken the bus down to Denver so I was like, “Hey: The last bus is heading out so either I need to leave or I’m crashing at your place.” So we went back to her house and started hooking up and I was inside of her when she looked me in the eyes and said, “I love you.” On the first date. And then about four strokes later she called me Mike, who I learned the next morning was her ex-boyfriend who she’d broken up with five months earlier.
There was also a time in grad school when I went out with a girl and we went back to my place and I’d had way too much wine. We were making out and I went to the bathroom and I threw up like a fountain. It was terrible. For like twenty minutes. And I came back into my bedroom and she was still there and she was naked and was like, “Let’s do this!” I was like … “You heard me for the last twenty minutes?”
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And then, for whatever reason, and it probably had something to do with the fact that I wasn’t really doing my side of things in bed, but she was not well-lubricated. And it hurt. Like I woke up the next day with rug burn on my dick. She was on top and she was just violently throwing herself around and she had breast implants that were really hard and she kept hitting me in the face with them and it hurt. The combo of not enough— or no—foreplay plus the drinking was very bad.
Some of the hottest sex I’ve ever had happened this year, actually. I went on a first date and we were driving home and kind of making out on the way back to her place. I said something like, “How are you feeling?” or something, or “What do you want to do?” and she looked me right in the eyes and said, “I want to suck your cock right now.” I was like, “Yes.” So we parked on a side street in Denver and she went down on me and kept stopping. I was very much into the teasing. She just had a very, very good technique. Very sloppy and very, very good. I came and kind of zipped my pants up and we were making out again, and she asked me, “Are you one of those guys who comes once and then can’t come again?” I immediately got hard and I was like, “I can go again.” And she went down on me again. That was like a solid hour of blowjobs, which is an insanely long time.
I have a huge amount of anxiety about that because I worry that I'm taking too long or that they’re getting a jaw cramp or something. So the fact that she kept being like, “Don’t try to come, I’m going to tease you forever because this is really enjoyable,” I think will forever stick in my mind.
I dated a woman for five years and before things got awkward, we were pretty adventurous. I had gone home to visit family for winter break when we were first dating and when I came back she picked me up at the airport in lingerie and a trench coat and high heels. And then we drove home and I put on a suit and we went to a bar and she was still wearing nothing and a trenchcoat. And then we went back to her place and we used a blindfold and very light handcuffs and I learned I’m into that. Like light, light, light bondage. I’m not really into hardcore bondage or anyting. I just like the sense of someone being in control or me being in control.
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