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

Fri, Mar 6, 2009

Advice, Dear Em & Lo

cherriesphoto by Balakov

A few years back we answered a question from a woman who was about to pop a young man’s cherry. We took the article down when we relaunched our site, but The American Virgin blog asked us so nicely that we thought we’d re-post it…

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 nothings 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 Responses to “Dear Em & Lo: How Do I Deflower a Nice Young Man?”

  1. ABITS Says:

    As always, beautifully done.

    nice refresh and review for veterans as well. these are good suggestions for any new coupling. might as well start off on the correct foot, so to speak, right? no sense in assuming, just because one or both of you are experienced, that all the finer points have been refined.

  2. kyril96 Says:

    I’d be careful about #5 (just let him lie there his first time): my first few times I had to be taking an active (moving) part, not just receiving. I would “zoom out” and observe because I wasn’t doing anything to feel like part of it. As you can imagine, this did not work well. So make sure he’s engaged and active when you finally do “the act”, if I had it to do over again, I would have started out in missionary position and moved on to cowgirl later…

    Also, as far as anal (#13), remember you don’t have to penetrate to stimulate! The shower is definitely a good place to start out trying it.

  3. Slartibartfast Says:

    It’s bits like this that showcase why Em & Lo are among the best darned sex writers in New Media for their demographic and time slots. If I’d run into someone who’d read this (or been fortunate enough to find it for myself) Once Upon a Time, I’d probably still be interested in having sex.

  4. Marcie Says:

    I love this guide and find it incredibly sensible. Thanks for remaining the clearest, most open and clear (let’s add considerate as well) sex writers I’ve ever come across!

  5. Brent Says:

    Leave the poor guy alone. He’s not a toy. It is clear you don’t have any emotional attachment to him or love for him, so when he does for you, you will just break his heart. Let him share that moment with someone he truly loves and someone that truly loves him.

  6. Irene Says:

    Brent is right on que. I totally agree. Something as special as your first time should be with someone that you adore. And unless it is a learning experience for both partners. Leave him alone.

  7. Chimot Says:

    Why you help to spread the demoralization to the public?. I respect people who stay virgin for the good reasons. Just leave the virgin guy alone. Sex is sacred for people with high moral standard people anyway. Keep your seduction skill for yourself and your partners.

  8. Nicci Says:

    I cannot believe you are actulally telling someone to seduce another whom is not yet ready to embrace the sacredness of sexual intimacy! Do you know how old these two are? Sexual intimacy is strictly for married couples. This entire topic should actually be called “How to Rape a Young Man” You are wrong for spreading this around! True relationships are never based on sex…get it right nymphos!

  9. Crystal Says:

    Nice. I was actually wondering about it since my fiance isn’t a virgin, but I am. these are some really good tips. Keep up the good work.

  10. Sandra Rais Says:

    Hi I agree with what Nicci says..
    Emm, Cherry.. do you think that you are a savior by doing this to others?
    Oh Please! Cut it off! You are just spreading some bad idea to another. I believe that you haven’t find your true love yet.. try to appreciate and devoted to love with the one that truely love you, you will discover one day that the happiness you encounter is greater than the pleasure of sex… love is sacred but not flirting around.. bear in mind.

  11. Kara Says:

    Nicci, you’re a prude!
    Nice work Em & Lo, it was really refreshing.

  12. holly Says:

    I am a 39 year old wife and mother of 2 from the “bible belt”(upstate SC). I was reading the comments after reading this very interesting article and was shocked at the finger-wagging, tsk,tsk,tsk, attitudes of some of the readers. If the comments they left are any indication of their real selves, I can’t figure out why they were perusing an article like this in the first place! Furthermore, where did it say in the post that the female was the aggressor? She only said that he was a virgin and she wasn’t. That does not mean that she was planning some kind of rape session with this “poor guy”. I doubt that many people would refer to him as “that poor guy” if they could see his face after his VFT if this much attention was really given to making the task so very open and comfortable. Unlike most of us who had their left pinke toe behind their right ear in a 1969 Chevelle! I’d be more inclined to say “lucky bastard”!!

  13. Duffy Says:

    Conflicted! Having lived a life style that is a reflection of the ideas that
    you seem to profess Em n Lo, I must side with the folks who say let this man
    make love to someone, however inept he might be to someone he loves atleast
    the first time. Before all the cynicism and shallowness of the times to come
    jade what should be more than just a mutual getting off session. For those of
    us who’s main purpose is mutual gratification..great advise. As a footnote
    it has been my experience that those of us men and women who are more sexually
    liberated and without a doubt technically better lovers…are almost always
    at some point cheaters…

  14. Ann Says:

    I like the Harry Potter books, I read the article because I’m (1) a writer and curious about people’s experiences and (2) often asked to give advice to people experiencing situations I’ve not experienced (like making love to a virgin), and I agree with Em & Lo’s advice.

    On the other hand, I agree with some of the others that Cherry Popper seemed to be taking advantage of her guy. They’d been together for one month, she doesn’t seem to want a long-term relationship, and she made no mention of his interest. He might have broken up with her as soon as she started pushing. Some people prefer to use sex as a way to express love as well as to satisfy lust.

  15. Lady Breeze Says:

    Wow, these are interesting comments, my first time on this page…

    Anyway, I guess ill catch up later and submit my own questins, I like how Em and Lo keep it 100%.

    Also, like the way you think, question asker! Im sure if the guy knew how much consideration were putting into this , he would REALLY be unable to control himself under your power…

    FIERCE

  16. Nina Says:

    I love these tips , I may have to use them very soon!!! Thank You

  17. haha Says:

    BREAK the GUY’S HEART? ha ha ha ha ha ha ha ha ha ha ha ha ha, a NO-STRING sex breaking male’s hearts! what a good joke! Break when it stops, you meant? Well, nothing lasts for life, especially freebies… and – MALE’S HEART? It’s an oxymoron, there is NO SUCH A THING… while their penises do not suffer, HEARTS does not suffer, too…

  18. Helixbill Says:

    I really appreciate the sensitivity you show in giving this young lady advice. It is sad that for most of us our first sexual experience can be less than wonderful due to ignorance, lack of consideration on the part of either party, and/or lack of communication.

    For those who express moral indignation at your advice: If he doesn’t want to be deflowered he is always free to say “No, thank you”.

    I can respect someone who wants to save themselves because of their moral conviction. But I hope we are getting past the point where we consider anything about our bodies to be “dirty”.

    As for anal play: Just remember that whatever comes out of that end went in through your mouth so how ‘dirty’ can it be?

  19. Slartibartfast Says:

    “It is one of the superstitions of the human mind to have imagined that virginity could be a virtue.”- Voltaire

    Having returned to this thread after a hiatus, I’ve been floored by some of the comments and the amazingly fuzzy thinking they exhibit. By way of example, Nicci decrees that “Sexual intimacy is strictly for married couples.” Am I to understand that she would only kiss someone to whom she was married? I’m certainly not opposed to such a course if that’s her personal preference, but I question how suitable it is for general application. If kissing, which (done properly) is a sexual act so intimate that many prostitutes won’t do it or charge extra, is ‘off limits’ prior to the nuptials then what’s in? Does it make sense to leave an exploration of such an important and wide-ranging topic as sexual compatibility until after the contract is signed? Everyone needs to find their own answers, I suppose, but I think that sort of blinkered view is juvenile at best.

    “Moral indignation is jealousy with a halo.”- H. G. Wells

  20. Destroyer_of_BS Says:

    Though this article has some good points, both parties, the people who asked and the people who answered respectively, are missing some fundamental points:

    1) Men (people) are not tools. You shouldn’t try to ‘train’ them to be ‘better’. A relationship is a two-way process.

    2) Abstinence/Being a virgin is one’s own choice. It may be due to religion or std paranoia, but it is his decision. Unless, you plan on having a long term relationship, don’t waste his time.

  21. copykatparis Says:

    Apparently some site told its “flock” to invade this space with moralising and other nonsense. Don’t feed the trolls!

  22. randomdude Says:

    @desroyer of bs

    dude rather than knowing nothing at all and not being able to satisfy my partner I see it as a good thing that there are people that will teach you how to do a better job rather than sending you out into the world knowing absolutly nothing other than the basics

  23. Communication Says:

    I am not some religous or morality freak or a prude but CP if you’re already thinking of his future woman you’d better leave this guy alone.

    And to Emandlo, #7 is a great piece of advice but what’s with the “teach him this, teach him that, he should”, what ever happened to spontaneity and basic good communication? Besides you’re assuming that CP is a sexgoddess. CP should not be the guys teacher. Having sex is not that difficult, it´s a lot easier than learning how to walk, drive a car, even animals can do it and they don´t have access to how-to- books. If CP is going to have sex with the guy she should be should ´handle´ him as every other guy, maybe have a little more patience than usual and maybe take the lead just a little but that´s it. If she wants to have good sex with him communication is the key. CP should work on communication in general with him.

    For all the people who think this is a great article I have a question. Do you equally like this?:

    Q: I’ve been dating this gal for about a month and found out that she’s a virgin. I’m not. By far. I’m looking for tips and tricks on how to train her and introduce her to this in a good way that will make her a better person for some lucky man down the road.
    A: We totally admire your brotherly attitude! If only every man thought this way. If you think she might be a bit of a slow learner, then tell her 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!”
    1. Next time she’s over, have her stumble across a fun sex manual that “just happens” to be out in plain sight. Have fun flipping through it with her. Let her borrow it before you do the deed.
    4. Set the pace. Show her how the pace of sex can change, how you can go back and forth between oral and intercourse. Let her watch you masturbate and then have her take over. The point is to show her that there’s no preordained beginning, middle, and end to sex.
    5. 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 she attends to your pleasure, either by giving you an orgasm or assisting you in giving yourself one. In other words, teach her that every time she gets off, so should her partner (unless he says otherwise).
    7. Never laugh at her or make her 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 her with your hands or your body.
    10. Every time you go down on her, she should return the favor — if not in the same sesh, then before you offer up that favor again. She needs to learn reciprocity.
    11. Teach her that what probably feels best to her during intercourse probably doesn’t feel best to you.
    Happy boinking!

  24. Beatrice Says:

    Wow what a controversial article!

    I read it as I have a male friend who is a virgin and wants someone to teach him the ropes, no strings attached. I was unsure how to proceed or if I should infact refuse so he may find his true love for this. I respect the fact that he asked me and am flattered and feel although it may be a slight pity fuck, that if we both are concenting adults who know where we stand then where is the harm?

    Personally I think it is all great advice although I think the sex book is not needed if you are open enough to discuss these things with eachother (and you should be if you are about to have sex) and anal play isn’t really for begininers. I would also like to add the main thing that isn’t actually meantioned, if he says no or is uncomfortable then you have to respect his wishes and not “train” them out of him. Just be open and honest with eachother and above all communicate!

    One message to the others who have replied to this, what most seem to forget is that it will be between two concenting adults and you’re own personal views on what should or shouldn’t be done are therefore irrelevant unless you are one of the two involved.

    Beatrice
    xx

  25. Beatrice Says:

    Oh and yes “communication” I don’t see how it is any different if the tables are turned, I feel the same way whether it is male virgin or female virgin.

  26. Madamoiselle L Says:

    Wow, who called out the Prude Patrol? (Often websites with “agendas” say “wehatesexbecausewearen’tgettinganybutblamourreligiousupbringingforit.com) send masses of people to invade other sites which say things they “don’t believe in.” WHY? I don’t go around to nutcase Right Wing anti-sex sites and try to “enlighten” them. I couldn’t care less. Why do the haters think they have the right to shake their fingers at others, simply because THEY aren’t having any fun?

    Hey, Brent and Chimot, get laid much? My guess is no. Those are the only guys I know who hate sex. And they usually don’t get laid because they think of all women with the “whore/madonna” dichotomy. Or are just plain jerks. Or both….

    If the young gentleman doesn’t want this young woman to be his First One, all he has to do is say, “Thanks, but I think I’ll wait.” Who in heaven’s name said anything about “rape?” The thought processes of the prudish and sex haters. I’ll never understand.

    I have also never met a man who wasn’t completely grateful to the woman who was his “First.” A number of these guys were certainly not on Love with her, or she with him, but were very thankful to her for her generosity and patient teaching skills. Young men don’t get their “hearts broken” much in situations like these. Really. There may be a few young men who would say “no” to this young woman’s offer, but damn few…..

  27. Slartibartfast Says:

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

  28. wigwam Says:

    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!

  29. Ackley Says:

    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!!

  30. Heidi Says:

    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.

  31. Marissa Says:

    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.


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