What to do when he’s a virgin
It’s bound to happen sometime. Things are getting heated, panties are flying overhead, and neither of you knows quite where this is headed. There may or may not have been alcohol consumption earlier, and you may or may not have met this guy before. Whatever the situation, here you both are. Nekkid.
Being the wild thing that you are, you automatically assume sex is on the menu. You hint at what you want, expecting him to reach over and pull a condom out from the stash.
But wait. A strange look crosses his face. Is that uncertainty? Maybe even terror?
“Oh my God, you’re a virgin.”
He didn’t even have to tell you. You just know. And suddenly it gets reeeeally awkwardly quiet as mortification sets in. We’ve all heard of situations where the guy is more experienced than the girl. But there seems to be little advice for the sex-savvy gals who find themselves with clueless boys.
Not to worry! There are numerous ways to handle someone who’s more familiar with anatomical drawings of the vag than a real one.
According to a random poll of my man-friends, most guys would lie about their virginity if given the chance to give up their V-card — even if they had no idea what they were doing. One guy boasted, “I never stop to ask for directions,” and cited the porn movies he’s watched as grounds for his expertise. Because everybody knows that real life sex is just like Pirates, right? Right.
So for all my bros reading out there, a word of warning: If you find yourself in this situation, DO NOT, I repeat, DO NOT feign confidence or professionalism. You’ll just embarrass yourself and your partner by polishing up (read: lying about) your resume. She’s not an idiot, and she will see through your bullshit — especially if she’s been through this before. Sex is a skill that takes time and practice to fine-tune; just because you’ve been a diehard Jenna fan since you were nine does not mean you could be her co-star. Just be honest! Honestly!
And ladies, contrary to what your guy will have you believe, not all male college freshmen are sexual virtuosos with incredible masses of experience. Especially on this campus, finding that rare, unpolished gem is not as rare as one might think. And even if he’s not a virgin, don’t assume that he knows what he’s doing.
Now let me channel my mommy voice for a minute and scold you for not exchanging histories or establishing a battle plan before letting it get this far. But I’ll cut you some slack because you are in college, this is a hookup, and how the hell were you supposed to know Mr. Macho has never rolled a taco in his life?
Yeah, it would be easy to throw your head back, laugh and point. This would be an easy way to get rid of him: Nothing knocks the tent over quite like the winds of laughter. However, his ego may never recover, and you were a virgin once, too. Remember?
There’s definitely a more mature way to handle the situation, and in this case, you’re the experienced one — act like it.
So when your women’s intuition tells you what he won’t, don’t freak out! There are numerous ways to handle this situation, any of which may work for you. Every case is different, too — there’s no blanket answer that will cover all the intricacies and details of your situation — so the best thing (and really the only thing) to do is put on a straight face and have a mature and responsible talk.
Ask him if he is honestly ready: Is he going to regret this in the morning? Ask yourself if you are honestly ready to be his first: Are you going to regret this in the morning?
No one likes to have this talk, but there’s no way around it now. What are the terms and conditions of your future relationship? Do you plan on seeing each other again, or is what’s-his-name from the frat party a one-time deal? If he says he wants to lose it, make sure you’re okay with being the de-flowerer. If you’re both perfectly fine with you being his first gal, then gear up me hearties, yo ho! Just remember to give him some guidance. His cluelessness will help neither of you.
Of course, to avoid the awkwardness of it all, you can always find a fun alternative to sex for the time being. After all, you can always do the deed tomorrow night, or next weekend. Your body has lots of happy buttons — it doesn’t take a Northwestern engineer to figure this one out. Don’t be afraid to try them all.
And so, my attentive pupils, both courageous and weak-of-heart, just remember that lying never did anyone good. Be honest, think this through and remember to wrap up before venturing in!
Sex Position of the Week: Aphrodite’s Delight
If you’re going to be playing teacher and student, might as well teach him something worthwhile. Face each other with him on top. Bring your thighs as close to your chest as you can, and bring your feet together, so that your legs form a rough circle. Have him enter you slowly and make sure you’re both comfy before racing towards the finish line. General kissing and fondling will make this a lot more exciting. If all goes well, it will feel good for both of you –- what better way to end lesson one of Intro to Sex?
Didn't we all want to deflower the Hanson boys? Or you can return home.

be my first?
urdumb
April 15, 2008 at 8:14 pm
i lost my virginity junior year of high school to a good friend who had a (pretty much ex-)boyfriend in the town she had moved from earlier that year (read: I was a virgin and she wasn’t). She may have been lying to make me feel good (I doubt it, because I think I still have the scars from her fingernails on my back), but she said it was among the best experiences she had ever had. Basically, it was a perfect, no pressure situation to lose your virginity: I was with a friend and we were the perfect kind of tipsy, in one of our friend’s parents’ king-sized bed. At the time I hadn’t done much more than receive oral sex from and manually stimulate other girls, and I was honest about it (actually, it was a small school, and we were probably the only people from our social circle who were having sex outside of a 1-year-long+ relationship, so it was pretty much implied.) It’s definitely better to be honest; besides, sex is always better when you let the woman take control
Frankly, I don’t think there is much danger in terms of emotional fallout from taking a guy’s virginity. Unless he has been brainwashed by some fundamentalist teachings, he probably won’t attach much ceremonial value to it… it’s much more likely to be a monkey he’s been trying to throw off his back for quite some time
my story
April 16, 2008 at 3:52 am
Thanks so much for sharing! Sounds like you are one of the lucky few with a good first experience.
I applaud you on you honesty. It’s true that guys don’t attach much ‘ceremonial value’ to it – but all the same, this would have been a lot more complicated if either party lied about their experience.
Tania Karas
April 16, 2008 at 10:29 am
BAYTA!
Dragon
April 16, 2008 at 3:19 pm
I mistakenly stole a guys v-card. He didn’t mention that he WAS a virgin before we did the deed and as soon as we were done, he was like “That was my first time.” I almost fell of the bed. The lesson there for me was to always explicitly ask. I didn’t realize that the response “I know all about it” is code for, “No, but I’ve just watched a lot of porn.” You live, you learn, I guess. Good article!
S
April 16, 2008 at 6:13 pm
LEAVE J.K. ALONEEEEEE!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
Matt Eliason
April 16, 2008 at 11:49 pm
In response to “my story said,”
So in order to attach powerful emotions to sex, a guy has to have been brainwashed by fundamentalist teachings? Sorry to break it to ya, but we guys aren’t all man-whores like you.
A.S.
April 17, 2008 at 12:55 am
Outstanding column Tania…. I know so many guys who are embarrassed, and, really, sex is always awkward the first time… Thanks for a great topic :)
Trisha
April 17, 2008 at 11:38 am
A.S.,
I’m not saying powerful emotions can’t be attached. You’re reading things into my comment that just aren’t there, probably because of an (admittedly ill-advised) reference to religious fundamentalism that angered you for another reason entirely.
What I meant was that the first time for a guy isn’t necessarily going to be emotionally unique just because it is the first time. I was trying to draw a distinction between the genders here, because for most girls the first time is pretty distinguishable from all the others for reasons related to the physical act and to all of the weird ways our culture reveres female virginity.
my story
April 21, 2008 at 3:54 am