We’re looking for stories about the first time you had sex. Email with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
I didn’t date in high school due to a strict upbringing so it took the whole 4 years of college to learn the rules of sex and then learn about how the rules don’t actually exist and that they’re all in our heads. To clarify, all this learning didn’t mean I was having sex, which is the biggest problem with a lot of universities; filling students’ heads with knowledge but neglecting to teach them how to apply those skills in real life.
So I graduated college, having gone no further than fingering a girl, expecting nothing different as I entered grad school. I was never a fan of the sex-baseball analogy but I think it’s fitting that I describe myself as “stuck on 3rd,” since the night I finally slept with someone was the last game of the 2004 American League Championship Series. The Yankees/Red Sox series had the entire town in a frenzy. Yes, I wasn’t in either city but at the time but no one cared where we were; sports history was being made.
My friends and I went to a local college bar with no intentions of picking up women. We order pitchers of whatever was cheap — loan payments after all — and found the last empty table in the entire place with a view of a TV. The seats were easy to find because most of the patrons were on their feet the entire game; but regardless of the reason, we were grateful to be comfortable and settled and looking forward to becoming drunk spectators.
That’s when Bridget came out of left field — god I hate baseball metaphors. She sat right down at our table, introduced herself, and helped herself to our beer. In hindsight, my friends and I only let her get away with it because she was a girl but we were definitely annoyed. I couldn’t tell if Bridget was drunk or whimsical but either way she was not there to watch the game and after a few minutes became a bother. I completely sympathize when a friend or family member, in her case a cousin, drags you to an event you have no interest in but she refused to acknowledge anyone else’s excitement and focus. She talked about several loosely related topics during crucial plays, requiring no conversational feedback. During a pivotal point in the game, none of us were even making eye contact, yet she kept talking.
During the 7th inning stretch, as the game started looking one-sided, Bridget left to go to the bathroom. We all leaned in and my friend spoke up with the intensity of a locker room pep talk, “She wants to go home with one of us and I don’t think she cares who. Which one of you wants to flirt back?” I feigned selflessness, like I was taking one for the team, and cooly stated “I’ll take this.” The guys may or may not have known I was a virgin but they could probably sense I pined for it the most. With that, my friends got up and walked over to stand in front of the main TV, leaving me alone to await Bridget’s return. She never asked where everyone went, she just sat right next to me, close.
Eventually the game ended with half the room celebrating and half the room pretending not to be upset; I was doing neither. With Boston breaking the Curse of the Bambino, I was working on breaking the curse of my 22 year dry spell. I gave Bridget my undivided attention. This seemed to be what she was waiting for because she immediately put her hand on my inner thigh, and with no resistance from me, proceeded to rub my crotch. I was shocked. A lifetime of sexlessness made me unaccustomed to PDAs but common decency made me feel ashamed of the public, over-the-pants, handjob I was receiving. I pulled her hand away but interlocked our fingers, my way of saying, “Don’t do that… but I’m still interested.” As the overwhelming mix of embarrassment and desire toned down to a manageable level, I gave her a deep look, “Wanna get out of her?” She responded, “Yes.”
When got back to my place, the tide of her sexual aggression towards me ebbed a bit. She needed me to say that I wanted her before she took her clothes off. With her naked in my bed, the worry about whether we were having sex was gone, now replaced with the worry that I was going to completely mess up. I kept the lights on because I figure if I did it wrong at least I could see what happened, learn from it like an airplane blackbox that survives the accident.
Aside from a strange moment when she moaned a girl’s name, the journey fared well. There were no technical mishaps to speak of, although I came so quickly I had to fall back on my experiences on 3rd base to return the favor. I didn’t ask her to stay over so she took a cab home, which was for the best because I was still in the haze of a first timer.
We never saw each other again after that night. Maybe because I’m not a good person, maybe because I still didn’t know what being good entailed. But I’ve gotten older and I’ve gotten better and now, I actually like it when a girl spends the night.
Oh, and currently the Yankees and Red Sox aren’t doing well but honestly, I don’t really care, I’m more of a hockey guy.
