Dear Em & Lo: How Do I Deflower a Nice Young Man?

Hey Em & Lo!

I’m in a tricky situation and don’t know where to look.  I’ve been dating this guy for about a month and found out that he’s a virgin. I’m not. By far. I’m looking for tips and tricks on how to train him and introduce him to this in a good way that will make him a better person for some lucky woman down the road. Any tips or places I can look to get ideas? Thanks!

— Cherry Popper

Dear CP,

We totally admire your sisterly attitude! If only every woman thought this way — and we’re not just talking about the cherry poppers here — then this world would contain far fewer men who think they’re awesome kissers despite the Saturn-like rings of saliva they leave around every girlfriend’s mouth. (For the record, we don’t mean to imply that poor kissing etiquette, not to mention underdeveloped bedroom skills, are purely a male phenomenon. It’s just that the average female sexual response tends to be a little more fickle than its male counterpart, and thus a poor bedside manner in a man is generally more noticeable and has more potentially catastrophic effects).

But while it’s uber-nice to want to train someone for all their future partners, you don’t want to make this feel like obedience camp. Instead, you need to focus on teaching by example. If you think he might be a bit of a slow learner, then tell him in advance, “If I do something to you, it usually means I’d like you to do it to me at some point. Follow my lead, and 5-6-7-8!”

The trickiest thing is finding the right balance between vanilla and not-so-vanilla. You don’t want to freak him out (or make him pull a muscle) by getting into all 768 positions of the Kama Sutra early on. But you also don’t want his Very First Time (VFT) — not to mention his second and third and forth times (assuming this is going to be more than a one-night stand) — to be so stereotypically “normal” that he gets it into his head that that’s the way sex is “supposed” to be. For example, if his first time is five minutes of quick thrusting in the missionary position (oh, high school!), then he might be inclined to think, “Huh. So that’s how it goes.” Thus, you need to show him a broad range of what sex can mean so that (a) he can figure out what he likes and what he doesn’t, and (b) so that he won’t develop any iron-clad assumptions about what should and shouldn’t be part of sex.

Some specific things you can do about doing it:

1. Next time he’s over, have him stumble across a fun sex manual that “just happens” to be out in plain sight.  Have fun flipping through it with him. Let him borrow it before you do the deed. The book isn’t meant to oust you as head coach; rather, it’ll just give him a little more confidence going in. The more ignorant he feels, the more his terror is going to paralyze him, and the harder it will be for him to concentrate on your lesson plan. Not that we’re ones to brag (oh, who are we kidding), but a very gentlemanly young virgin once told us that he couldn’t have gone through his VFT without first reading The Big Bang.

2. If he hasn’t yet asked you about your sexual health, ask him, “Don’t you want to ask me about my health record?” to show him this is just a matter-of-fact part of the hooking up process. And be up front about your own experience: when were you last tested and for what, how regularly you use condoms and dental dams, if you’ve ever tested positive for an infection that may still be contagious, etc.

3. Be sure to teach protection as an integral part of the process. During the VFT, put the condom on him so it feels rilly good: Don’t treat this as something unfortunate and clunky that has to be gotten out of the way. And show him some condom tips: blow in the reservoir tip to make sure it’s set up properly, pinch said tip to prevent a big air bubble from forming at the end, keep pinching it as you roll the condom down to make sure you reserve enough space for his ejaculate, and roll it all the way down as far as it will go, making sure to smooth out any air bubbles, etc. Next time you do it, have him roll one on; if he gets it wrong, correct him — gently and sensually.

4.  Set the pace. An occasional quickie is fine, but he should know that the majority of women appreciate a fairly slow build up, which means no boob-grabbing 2.3 seconds after the first kiss (unless, of course, it’s a quickie). Show him how the pace of sex can change, how you can go back and forth between oral and intercourse. Let him watch you masturbate and then have him take over. The point is to show him that there’s no preordained beginning, middle, and end to sex.

5. When it comes to the actual deflowering, it’s okay to let him lie back and enjoy the ride. He’ll have enough to think about just trying not to climax in under five seconds (or stressing out that he won’t climax at all), so it’s just plain nice to do the lion’s share of the work this time around. That said, during any pre-deflowering hook-up sessions, and during all other seshes that follow (whether or not they culminate in intercourse), make sure he attends to your pleasure, either by giving you an orgasm or assisting you in giving yourself one. In other words, teach him that every time he gets off, so should his partner (unless she says otherwise). Most importantly, he needs to know that the female orgasm is rarely achieved through stamina alone: It might mean switching to oral, or using a hand, or grabbing a toy, etc.

6. Oh yeah: toys. You don’t need a strap-on and medium-sized dildo with a vat of lube to introduce him to the wild world of sex. In fact, we’d steer clear of any props (except lube and barrier protection) during his VFT. But fairly soon after that, you should have him make friends with your toybox so that he understands from the very beginning that they are not a threat to his manhood.

7. Never laugh at him or make him feel stupid for an unskilled move or a naive question.

10. Be clear about what you like, but don’t simply bark directions and instructions. Where possible, lead him with your hands or your body. That said, don’t be afraid to tell him you’d love it if he’d do X, how hot it would make you if he did Y, and how Y — that thing he’s doing right now — is the best. But in order to avoid misleading him into thinking that everything that works on you will work on all girls, you might throw him a few subtle hints here and there, like saying “I know a lot of girls like X, but it just doesn’t do anything for me” or “A lot of my girflfriends don’t like Y but I love it.” (You might want to save the latter commentary for outside the bedroom, just so he’s not overwhelmed with information in the moment.)

9. Don’t ever fake orgasm, even if he deserves an A-plus for effort. He needs to know that somethings work and somethings don’t (depending on the gal) and that sometimes nothing’s going to work at all. While faking may improve his mood and confidence rather drastically in the short term, you’re only setting up him (and his future special friends) for disappointment in the long run.

10. Every time you go down on him, he should return the favor — if not in the same sesh, then before you offer up that favor again. He needs to learn reciprocity.

11. Teach him that what probably feels best to him during intercourse (deep in-and-out porny thrusting) probably doesn’t feel best to you. Most porn is made for guys, so the subtler moves that many women enjoy don’t often get a lot of air time. Show him the moves that got left on the cutting room floor, e.g. shallow slow penetration, and positions like the coital alignment technique which are designed to provide near constant clitoral stimulation, etc.

12. Show him exactly where your clitoris is in relation to your vaginal opening (how you like to have it touched), where your g-spot is (whether or not you like to have it touched), and any other specific places where his attention might be welcome.

13. Sometime in the first few weeks, take a shower with him and show him a little anal attention. Don’t go in like gang busters, just introduce him to the idea that he’s got lots of nerve endings back there and that straight people enjoy having them stimulated too.

14. For the sake of women everywhere, try to make his first post-coital cuddling experience a good one: Don’t force him to cuddle all night (unless he loves it) so that he never wants to cuddle again, and try not to smother him or let his arm get numb. Show him a few spooning positions that are actually possible to sleep in (assuming he doesn’t have personal space issues) and strongly suggest to him that a minimum of 15 minutes’ snuggling is just a decent thing to do.

Happy boinking!

— Em & Lo

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32 Comments on "Dear Em & Lo: How Do I Deflower a Nice Young Man?"

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3 years 9 months ago

I don’t wish to be rude to the author of this article but it seems very patronising. There is some good advice but just because someone is a virgin it doesn’t mean they are an idiot too. You would have had to live in a cave for the last 10 years to not know anything about sex. Information about sex is everywhere and not all men are dim enough to believe that porn is representative of real women. However, as probably every man has watched at least some porn there will be no way he will be under the impression that sex involves 5 mins of missionary position thrusting. My boyfriend was a virgin when we met and our first time was wonderful, in fact, on our third time I had my very first orgasm during sex. A man is going to be nervous enough about his first time without some woman patronisingly showing him a sex manual and telling him where things are. It is only going to make a man feel as though his partner feels he has to be the greatest lover of all time on his first try and that isn’t fair at all. My boyfriend is a fantastic lover and I didn’t have to ‘train’ him. Be sensitive to your man and just talk to him he will thank you for it.

3 years 10 months ago

I have to say that this is the only article that I could find online that was of any actual use to me. My partner and I have been together for a month or so, and have known eachother longer, he is a virgin, I am not. We want to make love, but I was desperate to ensure that his first time was a lot better than mine was, so I have taken the pains and the lack of sleep to find this page. So, to all those who think that this page is wrong, need to back off and look at it from this point of view as well as CP’s before making a judgement.

4 years 11 months ago

That is most likely the perfect article that ever cross my reference. I don’t see why anybody should disagree. It could be too simple #for them# to comprehend…anyway good work i’m coming back here for Extra Great Stuff!!

5 years 9 months ago

Fantastic article, I loved it. I don’t want to get involved in the comment war, though I happily would – but suffice it to say I definitely side with the likes of Mademoiselle L and Slartibartfast.

I read this because I’m looking forward to my boyfriend’s first time. I love him very, very much. And it’s because I love him that I want his first time to be a success, so to speak. I wouldn’t dream of badmouthing Cherry Popper or her man (on the contrary, kudos to her for her generosity of spirit!), but some of these commenters could stand to consider that this kind of information can foster successful relationships, far from fueling short-term ones.

Anyway. The point is, thanks for the great ideas, Em & Lo, certainly gives me something to think about!

5 years 10 months ago

As usual, Ma’amselle El, you’re spot on.