My First Time

My First Time: “Damn, I should have undressed.”

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I’m sitting in his bed wondering if I should take off my clothes, or just wait until he comes back in the room. Is it sexy for guys to watch a girl undress herself? I’ve done it countless times in the mirror, but I’m pretty sure the effect could be off-putting without my usual background theme music. If I’m still dressed when he comes back then he might want to undress me himself, and that could easily be really good or really bad.

Even though I’m a virgin, I’ve always known about sex. I had a 10 year old brother who secretly showed me porn when I was 5, I went through puberty at age 8, and my grandmother was a retired sex therapist who kept all of her books in the room reserved for the grandkids when they sleep over. Sex was never a mystery to me, so I was never in a hurry to do it.

The funny thing is that all of my friends assumed I had already done it since I knew basically everything there was to know about it. By senior year, age 18, I had kissed boys, sure, but I had never been naked with one, or even been alone with one in a bedroom. I actually broke up with a boyfriend I really cared about because I knew I wasn’t interested in satisfying him in that way, and I didn’t want to be cheated on. I would also like to throw out there that I was not, by any means, a socially challenged nerd like from the movies that desperately craves male attention. I had been propositioned more times than I could count, but I had never felt the internal pressure to embark on that particular adventure.

Looking back on my past, my actual personality was never really reflected in other people’s opinions of me. People thought that I was this sexually adventurous, mysterious, know-it-all badass, when, in actuality, I was just a kid whose parents would take away her books as punishment instead of grounding her since they knew she never did anything inappropriate… and I was totally okay with that. Eventually, watching all of my friends actually go through this experience I was pretending to have already done began to take its toll on me. I wanted to physically experience this phenomenon that I could imagine so vividly in my head.

“Oh. You tryna have sex?”

It suddenly dawned on me that I hadn’t actually confirmed with him that I would be getting deflowered, despite being in his bed at two o’clock in the morning, and, if previous encounters were any indication of how tonight would go, I was not in the clear. The question is, how exactly does one request sexual intercourse? This was not one of the useful things taught in health class, and the difficulty I had experienced getting to this point made me understand that this was something that needed to be handled delicately. As I listened to him bid his party guests goodbye in the dorm living room, I considered my choices. I could just come right out with it (Hey, we should, like, totally have sex!), or I could simply straddle him (is that rape?), or I could just start suggestively rubbing his arm until he got the message.

Option 1 was out, since nothing that ever comes out of my mouth is ever sexy and would probably diffuse any sexual tension. Option 2 was out, because straddling him would put me on top, a position which would immediately reveal me as the prude virgin that I was, a fact that I intended to keep hidden. I had a feeling that any boy faced with the prospect of deflowering a collegiate virgin wouldn’t actually go through with it based on the fear that she would inevitably become attached to him.

That suspicion is probably why losing my virginity ended up becoming such an ordeal for me. As a new freshman on campus, the veritable mass of upperclassman males coming at me from every direction both annoyed and vaguely disgusted me. I was of the opinion that thirsty boys were not going to be adequate in bed.

So, there I am, sitting in his bed, fully clothed and waiting for him. After what seems like an eternity, he comes in the room, turns off the light, gets in the bed next to me, and lies down with his back to me. I’m still sitting up, looking down at him, confused. Damn, I should have undressed. I suppress a frustrated growl.

I met Duke literally the first day of college. I saw him and I knew that I wanted him. He was tall, light-skinned, curly haired, on the football team, and only a couple of years older than me. He was on the quiet side and didn’t seem to have a swarm of foolish-looking girls panting after him like the other student athletes did, but he was too good-looking to not be experienced. I hadn’t even spoken to him yet and I thought I had it in the bag: cherry popped within the week, we’d fist bump, and I’d be on my way. My foray into the world of college sexuality consisted of me leaving my dorm and being accosted by the majority of the single, minority male population without actually doing anything, and I expected that the extent of my push to get Duke wouldn’t have to go beyond a lingering look in his direction and a beguiling smile or two.

I get annoyed and clear my throat aggressively. I continue to do so until he rolls around and looks at me. Immediately, my voice gets caught in my throat, so instead of speaking, I settle for a raised eyebrow, a signature move of mine used for a wide range of emotions including, but not limited to, annoyance, mirth, anger, confusion, and pensiveness. He blinks at me slowly for a second and then says, “Oh. You tryna have sex?”

Absolutely terrible. I had only been in a situation this close to intercourse once before. I needed to lose my virginity, but it couldn’t be to someone that I could risk getting attached to. Unfortunately, I wasn’t sexually interested in any of the other guys at my high school and, in case you haven’t visited Connecticut, the state doesn’t really boast a great supply of attractive males ages 18-21.

But then I went to college and met this gem of a guy, Duke. If I had been more mature, I would have gotten up and walked out, but, oh no, not me. I keep my eyebrow raised and muster up my most indifferent tone of voice. “Yes.”

In retrospect, I went about this all wrong. Nobody has ever had hot sex because they asked for it outright. Hot sex comes from pretending that it isn’t going to happen, that it shouldn’t happen, that it won’t happen- but both parties know full well that it will happen. He didn’t get the memo and I probably should have waited until he did before I pounced.

“You wouldn’t happen to have a condom, would you?” he asks sheepishly, hovering at the door. I blink. Is the girl supposed to provide the condom? My mind races and then I decide firmly that no, this is actually his fault, and raise my eyebrow again.

“Of course not.” “Lemme go ask Jon if he’s got one.” I let out the breath I had been holding, my heart thudding in my chest. I’m about to have sex. I’m still grinning to myself when he comes back in, but my grin abruptly vanishes when he drops his pants and asks me to put the condom on. I get the feeling that I shouldn’t be fixated on his groin, but it was staring at me, blushing at me almost. He clears his throat and I realize he is still waiting for me to take the gold-foiled condom out of his hand. My mind races again. I’ve never touched a condom before, what if I put it on inside out, or break it, or drop it?

“What, you don’t know how to do it?” I ask in a tone that would suggest I was making fun of him. He is standing up next to the bed, dick out, condom in hand, with the most bewildered expression on his face. Finally, he shrugs and clumsily applies the condom. Later experience taught me that putting on a condom should never take as long as he took, but I wasn’t about to say anything.

I highly doubt that we fist-bumped after I got dressed, but the sentiment exchanged between us was probably the same.

He climbs on top of me and I try to relax, but I’m wondering if we should be kissing. I think he has nice lips, but I can’t imagine being able to concentrate on anything going on down there while I’m doing something up here. That probably comes with practice; so I decide it’s better not push it. Speaking of pushing, I can definitely feel him down there, but I can also tell that nothing is actually happening. He’s trying, but it just isn’t going in. I suppose this could be chalked up to my being virginally tight, or his reluctance to be a bit more aggressive with the thrust.

After a couple minutes of nothing, I decide it will be best if I am the first one to say something, and go, “What’s wrong with you?” As soon as the words escape my lips, I wince. Too harsh. He looks down at me, again with the bewildered expression, saying he has no idea, and then adding that trying it from behind would probably have more success. Behind? I hold back the question threatening to burst from my lips and destroy my whole charade and raise my eyebrow again. After asserting that “from behind” was merely the direction I would be facing, and not the location I would be losing my virginity from, I cooperatively turn around.

Something about that position really loosened lady land up, because there was no difficulty entering, and I proceeded to lose my virginity. I think it’s only fair to mention here that it is inappropriate to say that I lost my virginity, when in reality, I did absolutely nothing the entire time. I guess I enjoyed it. I know I didn’t bleed and I didn’t have that “sharp, stinging pain” most virgins experience, but I did feel rather sore down there for a bit after. I liked the feel of sex, the idea of sex, and the sensation of sex, but he didn’t make me orgasm. I waited until lady land had had enough banging and then proceeded to emit all of the orgasm noises the women in the pornos make so that Duke would be satisfied.

Understandably, I chose not to sleep over, but the actual act of me leaving after it was done is kind of a blur. I highly doubt that we fist-bumped after I got dressed, but the sentiment exchanged between us was probably the same, and I felt no compulsion to see him the next day. During the short walk back to my dorm, I skipped I was so excited… you know, finally a woman, the world is my oyster, etc.

Female, 18, United States


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