Love & Sex

My First Time: Female, 18, South Carolina

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Female, 18, South Carolina

There was a time in my life when being a virgin made me more anxious than I could handle. Being socially behind from my classmates in school gave me palpable anxiety. There were so many things I hadn’t done — drank, smoked, had a boyfriend. In social situations, I felt like I was missing some essential piece of being normal, as if I was the only one in the room without a shirt. This changed when I made it out of my small southern town, and into the Ivy League. Once I was around people that “got” me, my social life exploded. I was on cloud nine, and I still am.

He was another freshman on the debate team. He was an experienced debater, and had competed on the national level. I had never debated in my life. He was tall, thin, sharply dressed, and in the business school. I remember the first time we really noticed each other: we showed up to a practice one night, both wearing black boots. His were stylish but fairly plain. My black cowboy boots are the pride of my life, with a pointed toe and beautiful white embroidery up the calves. If I go out wearing those boots, I’m going to get at least one compliment per hour. That night, someone pointed out our similar footwear, and I saw something distinctly both jealous and impressed in his expression. 

We became friends after that. On the bus ride back from our first debate competition, we sat in the back with the freshman, getting drunk off of rum in a Gatorade bottle. We agreed to go hit up some frat parties after we got back, however, the party scene wasn’t great that night. We ended up eating pizza and going back to his room to watch Game of Thrones.

I wasn’t thinking about hooking up at all, but the make out started shortly after Game of Thrones ended. His roommate was out for the night. I was on bottom, running my hands over his sweaty lower back, when he asked, “Do you want to have sex?”

I had hooked up with a guy for the first time two weeks before, and that was it. Despite my lack of experience, I agreed to have sex with no hesitation. He assured me that it was okay if we didn’t. He told me about how, during his first time, he got so nervous that it “didn’t happen,” and asked me not to tell anyone that. He’d been with two other girls since. 

I insisted that I was ready, so we started off with me giving him the worst blow job ever given. I had a small mouth and terrible gag reflex, and it was a nightmare of teeth and choking. We stopped trying quickly, and laughed it off. Despite our lack of success, he held my hand the entire time. 

When it came time for the actual penetration, I asked if he had a condom. All he had was Trojan Fire and Ice, which I had heard burned really badly. I was already going to have a dick inside me, and it wasn’t going to be a fiery hell-dick under any circumstances. Luckily, I had a plain condom stashed in my wallet. He put it on with surprising speed.

The actual penetration was when the whole thing started to go downhill. I was so tight that it would only go in about two inches max. It didn’t hurt, but it just wasn’t working, even after trying a number of different positions. He started to get subtly agitated, and it got worse when he lost his erection. He managed to get it back up with a few strokes, and we tried over and over again to penetrate further. I started to ask a question when — “Shhhhh!”

He lost his erection a few more times before we finally gave up. Before we went to sleep, I asked, “Have you had that problem before? With the other girls you’ve been with?”

“They were a lot more experienced than you.” 

When I woke up in the morning, he brought me coffee in bed, and we chatted about our studying plans for the day. After a while I went back to my room. 

We didn’t talk after that. He stopped coming to debate meetings as much, and I wondered how it was possible that I was repulsive enough that he would barely make eye contact. For the first few months afterward, I felt nauseous every time I saw him.

He started dating a senior in a fraternity that November. After they broke up, he started sleeping around with a lot of guys on campus, and got something of a reputation in the gay community. I knew fully well before we had sex that he didn’t love me, and I didn’t care. But the thought that I gave it up to someone who maybe wasn’t even attracted to me physically — I don’t like to think about it. It didn’t help that, a few months later, one of my gay friends informed me that he had had a bet going with his roommate to see who could get a blow job first. He won. I didn’t. 

I’m learning to handle being around him again a little bit at a time. Sometimes I try to feel sympathy for him — the stress of hiding your identity can bring up a lot of nasty emotions. I know he was probably felt scared and isolated. I still haven’t been able to feel authentic sympathy, but I feel it in theory. It doesn’t stop me from wearing my cowboy boots to every debate party, partly because they’re great, and partly because I see him eyeing them every single time, clearly jealous. 

Image via Flickr.