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. The potential awkwardness is making my underarms sweat. My heart feels like it’s going to burst out of my chest as I weigh my options. First time is kind of a big deal, but I really didn’t think it was going to be this hard… pun intended.Even though I’m a virgin, I’ve always known about sex. I had a 15 year old cousin who secretly showed me porn when I was 7, I went through puberty at age 9, and my grandmother was a retired sex therapist who specifically kept all of her books in the room reserved for the grandkids when they sleep over.   She probably didn’t see any harm in it, not anticipating that a precocious 10 year old wouldn’t be able to sleep one night and would curiously drag a chair over to the book case to investigate what The Joy of Sex was all about. Point is, 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 enough to talk knowledgeably and confidently about it. I went to two different high schools, and everyone at each assumed I had lost it to someone at the other school. I chose to go along with their assumptions because it made me seem more credible, plus I like giving people advice and if they knew I was a virgin they would probably have stopped asking me about coitus.

As high school came to a close, all of my friends began losing their virginities. Without fail, every single one of them came to me beforehand to find out what it would be like and I would grin and launch into an explicit account of my experience, taking into account all of the things I had read, from the sharp pain of the breaking of the hymen, to the inevitable soreness, and even throwing in a joke or two about “his” strange pubic hair situation. Man, I was good. Despite never having experienced the actual event, I knew I was right when it came to describing it. I always thought this was strange because, to be honest, not only had I never done the deed, I had also never even come close.

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 was not, by any means, one of those socially challenged nerds that are exaggeratedly characterized in the movies. I had been propositioned more times than I could count, but I had never felt the internal pressure to embark on that particular adventure.

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, plus I wanted to actually be good at it when it was time to get married. I was concerned that with the way I was headed I was going to end up as one of those virginal brides and I just wasn’t about that life.

So, there I was, palms sweating, chest thumping, waiting for 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. If previous encounters with him 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 undoubtedly 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. If they were, indeed, good in bed, then they wouldn’t need to chase girls. It’s common knowledge that if you’re putting it down, word gets around. Some couples enjoy the awkwardness of their first time, giggling as they attempt to navigate each others’ bodies and getting over the inevitable embarassments that occur, but, to be honest, that should only be for couples.

Why would you want to be awkward with someone you’re not in love with if you don’t have to be? If I could be spared that, I was definitely going to try. I was already going to be working from a disadvantage since I had never had sex, so I needed someone who could pick up the slack. Someone who was experienced, who wouldn’t know I was a virgin, but also wouldn’t notice my awkwardness and hopefully wouldn’t go around discussing my inability to perform during the actual act. Virgins can be bad in bed, sure, but virgins pretending to already be, well, popped, should not be.

I was banking on my years of basketball, fighting with my older cousins, and various other contact sports to keep the actual event fairly painless. I didn’t have the mental capacity to deal with both pain and fibbing in a naked situation. To make matters worse, my lack of interest in masturbation put me at another disadvantage, as I had never had anything even resembling that particular organ anywhere near lady land. I was going in blind, but still determined.

I decide to remain fully clothed. A naked girl waiting for a guy in his bed is a little more alluring and sexually overt than I could handle. I’m not trying to fake an A-game, here, just a solid C+. After what seems like an eternity, he comes in the room, turns off the light, gets in the bed next to me, and lays down with his back to me. I’m still sitting up, looking down at him, confused. Damn, I should have undressed. It appears as though his invitation to sleep over had been, in fact, an invitation to sleep.

No. Cuddle sleep-overs are a total no-go for me. Those beds are tiny, he’s a big boy, I am by no means a small girl, and I’ve always been a thrasher. If I’m sleeping, I’ll sleep in my own bed, thanks. But now, I’m faced with a slightly more awkward situation. How to proposition a boy who wants to go to sleep?

I suppress a frustrated growl. At this point I should just throw in the towel, planting a flag on the mountain be damned, but I had just spent the last month climbing this mountain, and I am not about to let someone else yodel on it. I stretch out my fingers to touch his well-muscled shoulder and then chicken out. I can tell by his uneven breathing that he hasn’t fallen asleep yet, and I wonder if he thinks I’m weird for not laying down. I shake those thoughts from my mind. Of course I’m not the weird one; I’m actually trying to have sex here. He’s the weird one.

I met Smith* literally the first day of college. I saw him and I knew that I wanted him. He was tall, light-skinned, curly hair, 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 having to do anything, and I expected that the extent of my push to get Smith wouldn’t have to go beyond a lingering look in his direction and a beguiling smile or two.

First of all, it took me almost two weeks to get him to even notice me, a feat which I accomplished by barreling into him outside of the Curry Student Center and almost knocking him over. After that, it took almost another week to get his contact information so I could “woo him” outside of my perfectly planned run-ins. By the way, when I say contact information, I do not mean I got his phone number. He gave me his screen name. I should have given up then and there, as it was perfectly clear he was not interested in me, but I had decided on him and I’ve never been one to admit defeat. Not to mention, I do love the chase. So, I took his screen name and within another week had gotten his phone number. #Swag.

Granted, it did not need to be this difficult, but I refused to cut my losses and select someone else randomly from the masses panting after me. While I was more than eager to cut the cord, I didn’t want to do it with just anyone, and I believed that his disinterest in my aggressive, albeit clumsy, advances were actually a sign on his part that he respected me too much to just screw me on sight, like everyone else seemed to want to do.

So, I relentlessly pursued Smith with my own, patented blend of flirtation, disinterst, and bro-ship. Bro-ship, in case you didn’t know, is defined as the act of pretending to be “boys” with an attractive male so he thinks you’re just chums and lets his guard down around you.   In doing so, he accidentally allows you to seduce him with your feminine wiles. A favorite of homewreckers, I believe, but also useful when dealing with guys who are innappropriately sexually uninterested in you.

I shake myself out of my mini reverie and look back down at his back. 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?”

Oh, God. How absolutely terrible. I had only been in a situation this close to intercourse once before, in the summer before college, and it wasn’t anything like this. That had seemed perfect. We were on a beach, we were alone, we were a little tipsy, and we were attracted to each other. It should have been perfect…

…But I couldn’t do it. I knew right then and there, even through my semi-drunken haze, that this was not the time and place. Trust me, it wasn’t that I imagined this situation with Smith as my ideal time and place, but I knew that I liked Dan too much to give him that part of me and make a big deal out of it, especially since we were parting ways in less than a month.

For females, losing our virginity carries a stigma that we will become attached to whomever the lucky guy is, and I had an epiphany while rolling around naked with Dan in a Foxwoods Casino hotel room: If I lost it to him, I would become attached to him. Sex would only build on the feelings I already possessed for him. Yes, I was done being a virgin, but not done enough to risk losing my heart and self to this boy who, while I did care for immensely then, would probably not be in my life within the next four years.

After I politely rolled him off me, stating that I had no intention of sleeping with him, we went to sleep. In the morning, he wanted to talk about it, but I knew that my new, unconventional perspective would probably not go over too well with him (plus I still wanted to maintain my non-virginal status), so I lied and told him that I just didn’t feel that way about him.

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, Smith: The one boy in college I could have grabbed who wasn’t interested in sex, or more specifically, sex with me. Tryna have sex? The words rang in my head and I winced internally. 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. ” Should’ve said no. Dummy.

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. The problem was, I felt like my virginity was holding me back from true intimacy, and that as soon as it was over and done with, I would finally be able to comfortably and securely be with someone, mind and body.

So, for those weeks leading up to this not-so-sexy encounter, I commenced my campaign to win the body of my chosen deflowerer, not matter how difficult it turned out to be. It was probably fairly obvious to him that I was entirely uninterested in his heart, or his mind, for that matter, which was most likely the key component in what made this conquest so difficult. Nobody likes to feel like they’re being used, even boys who just use girls for sex. Most of them probably thrive on the knowledge that they hold someone’s heart in their hand; it makes the eventual conquest that much sweeter, I would imagine. Just as much as we females enjoy the chase, so do males. Even an attractive girl can become uninteresting if she’s too available or if it’s too obvious that she wants you.

This might have worked against me for the long haul, except for the undeniable fact that Smith had yet to actually have me, which kept my desirability in the air, no matter how annoying I was being. To my credit, my perseverance eventually paid off. Roughly a month after first spotting him walking across the quad, I had successfully navigated my way into Smith’s bed at the end of a night. And no, I did not sneak in there; that would have been weird. I was invited. I had spent the majority of the party not-so-subtly hogging him and dancing with him, so that when the after party arrived, he would be primed for my clumsy seduction.

Regardless, as the party was winding down (I was not-so-casually perched halfway on his lap), Smith turns to me and says,

“Tryna stay over?” 

That should have been a red flag right there, but the whole process had already gone on far longer than anticipated, and I was just ready to do the damn thing. At this point, I was prepared to bulldoze over any ignorant comment or foolish question that might come out of his mouth.

Smith gets up and starts fumbling in his drawers while I wait in his bed, posed in the position I feel makes me appear the most alluring and grownup, although I really wanted to start gnawing on my fingernails.

“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? Shit. My mind races and I decide firmly that no, this is actually his fault, and then 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. Sex. Me. Doing it. I’m still grinning to myself when he comes back in, but my grin abruptly vanishes when he drops his pants. 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 realized he was brandishing a gold-foiled condom at me, waiting for me to put it on. 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 happened to the days of putting condoms on bananas in Sex Ed? I never got to do that! Not to mention, I didn’t feel any compulsion to wrap my hand around his penis, which quivered at me every time he breathed.

“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. I would have laughed, but my situation is too precarious to break character. Finally, he shrugs and clumsily applies the condom. Experience later in life taught me that putting on a condom should never take as long as he took, but I didn’t know that. I graciously choose to remove the bottom half of my clothing instead of watching him struggle with the rubber and mentally congratulate myself on taking the extra 10 minutes in the shower to shave everything. Smooth as a baby’s bottom, if I do say so myself.

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; 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, but I have my own personal theory.

You see, I think that there are three penetrable walls within lady land. The first is on the outside, quite obviously seen, the lips? The second is the muscular wall which can clamp down and allow only the tip inside, and the third rests midway down the shaft. Well, apparently, I am clamping down walls 2 and 3, and I honestly have no idea how to relax them. At my GYN appointments, my mother would tell me to use my stomach muscles to mime taking a dump, since tightening the opposite muscles to lady land forces her muscles to loosen, but there is no way I am doing that here. Accidental farting (or worse) would probably only add to the awkwardness of the situation.

After a couple minutes of nothing, I decide it will be best if I am the first one to say something, and say,

“What’s wrong with you?”  As soon as the words escape my lips, I wince. Too harsh. I’m overcompensating. He looks up 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, then 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.

Well, 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. More accurately, he took my virginity, in an especially clumsy way. I guess I enjoyed it? I don’t know. 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 movies make so that Smith 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.  The next morning, I promptly called my grandmother to announce that I had done the damn thing while simultaneously revolutionizing feminism because I totally wasn’t in love with Smith. I could almost hear her smirking at me over the phone, but she calmly congratulated me instead of mentioning that everything I was saying was complete crap. That realization didn’t come until a couple weeks later, after the initial high had worn off and I realized that I totally did have a crush on Smith… a crush that lasted for several months.

I guess, in retrospect, it doesn’t really matter how you do it. Giving a private part of yourself to another person is always going to have an emotional attachment; what you do with that is up to you. Some of us ignore the feeling and attempt to make the private part as public as possible to avoid future angst, and some of us hold onto the feeling and relish the emotional attachment that comes with sharing something that wholly belongs to you with another. I’m definitely the second here. I don’t regret my choice, but I do know now that it could have been so much better than it was…

Meh, it’s all good though because, you know what? I still did it.

Oh, I should probably mention that Smith and I reconnected a couple of years later, and guess what? Turns out he lost his virginity to me. *face palm*

Short Story – Becca Davis – 2013 

*Name has been changed.