How to Cash in Her V-Card

You’re a straight guy who’s had intercourse. You’re dating a woman who hasn’t. But it’s looking like you’ll be her first. Here’s how to do it right in 19 key steps:

  1. Engage in lots of foreplay. This is not the time for 2 minutes of kissing followed by 1 minute of boob grabbing before you get straight to the old in-out. Nope, you’ve got to get her very aroused before any penile poking. Think: lots of teasing.
  2. Don’t think of handwork and oral sex as foreplay. Think of it as sex. Show her that these forms of sex are just as legitimate and effective as intercourse (because there’s a good chance she’ll achieve orgasm with you via these two methods before she does via intercourse). In fact, if you’ve already engaged in handwork and oral sex together before now, explain to her that you two have already had sex. Show her how the pace of sex can change, how you can go back and forth between oral and intercourse. The point is to show her that there’s no preordained beginning, middle, and end to sex.
  3. Use lube. She’ll probably be nervous, which may adversely affect her own natural lubrication production. But it’ll also teach her that there’s no shame in using sexual aids in bed Hey, lube is just another kind of sex toy!
  4. Don’t use porn as a way to prep her. You might think it’s a good idea to prepare her for what’s to come (no pun intended) by showing her your favorite porn, but you’d be wrong. Porn is a fantasy — and chances are your fantasy is not going to be her fantasy. In fact, your fantasy might scare the pants back on her.  Sure, she might see some of the more technical or mechanical aspects of intercourse, but since a lot of porn isn’t great at conveying the tactile, emotional, spiritual and romantic aspects of sex, she might find it too clinical and thus off-putting.
  5. A great sex manual is a better way to go. If she definitely seems eager to learn more before you two get the deed done, then there’s nothing wrong with suggesting a good book or website about the how-to’s of good sex that she can take a look at on her own (or that you can peruse together).  After all, the more ignorant she feels, the more her terror is going to paralyze her, and the harder it will be for her to be in the moment.  So may we recommend “SEX: How to Do Everything” and EMandLO.com as the kinder, gentler sources of adult sex education?
  6. Find the right balance between vanilla and not-so-vanilla. You don’t want to freak her out (or make her pull a muscle) by getting into all 768 positions of the Kama Sutra early on. But you also don’t want her Very First Time (VFT) — not to mention her second and third and forth times (assuming this is going to be more than a one-night stand, we hope!) — to be so stereotypically “normal” that she gets it into her head that that’s the way intercourse is “supposed” to be. For example, if her first time is five minutes of quick thrusting in the missionary position (because you want to make things short and sweet), then she might be inclined to think, “Huh. So that’s what everyone’s been talking about? Why all the fuss?” Thus, you need to show her a broad range of what quality sex can mean so that (a) she actually enjoys intercourse, b) she can figure out what she likes and what she doesn’t, and (c) so that she won’t develop any iron-clad assumptions about what should and shouldn’t be part of sex.
  7. Talk about your health history. If she hasn’t yet asked you about your sexual health, ask her, “Don’t you want to ask me about my health record?” to show her 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.
  8. Be sure to teach protection as an integral part of the process. During the VFT, put the condom on yourself as a sexy part of the session, Christian Grey style. Don’t treat this as something unfortunate and clunky that has to be gotten out of the way. And show her 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 her roll one on you; if she gets it wrong, correct her — gently and sensually.
  9. Do the lion’s share of the work. When it comes to the actual deflowering, it’s okay to let her lie back and enjoy the ride. Don’t let her think that she has to put on a porn-style performance for your benefit. Make it clear that as long as she’s enjoying herself, you are too. It’ll take some of the pressure off.
  10. Try to give her an orgasm, but don’t go overboard.  It’s a goal worth aiming for, but not if you’re both getting frustrated and sore. She needs to know that the female orgasm can be an elusive beast, one that’s rarely achieved through stamina (or intercourse) alone: It might mean switching to oral, or using a hand, or grabbing a toy, etc. Don’t do anything to make her feel like she’s broken if it doesn’t happen for you guys. In fact, you might mention beforehand that it probably won’t happen this first time — again, to help take the pressure off.
  11. Save the toys for next time. You don’t need a 10 speed vibe to introduce her to the wild world of sex. In fact, we’d steer clear of any props (except lube and barrier protection) during her VFT. But fairly soon after that, you should encourage her to get her own toy (if she hasn’t already), so that she knows she can “practice” when you’re not around!
  12. Never laugh at her. Or make her feel stupid or silly for an unskilled move or a naive question.
  13. Be clear about what you like, but don’t simply bark directions and instructions. Where possible, lead her with your hands or your body. That said, don’t be afraid to tell her you’d love it if she’d do X, how hot it would make you if he did Y, and how Y — that thing she’s doing right now — is the best. But in order to avoid misleading her into thinking that everything that works on you will work on all guys, you might throw her a few subtle hints here and there, like saying “I know a lot of guys like X, but it just doesn’t do anything for me” or “A lot of my friends don’t like Y but I love it.” (You might want to save the latter commentary for outside the bedroom, just so she’s not overwhelmed with information in the moment.)
  14. Don’t fake an orgasm, even if she deserves an A-plus for effort. Let’s say you’ve just moved too slowly, out of respect for her, for your own O to happen. While faking may improve her mood and confidence rather drastically in the short term, it’s better for the long run to teach her that sometimes Os don’t happen, and that’s okay. She needs to know that orgasms aren’t guaranteed for anyone, male or female.
  15. Teach reciprocity. If she wants to go down on you during this first time session, then make sure you go down on her. If you go down on her first, then for this VFT she can get a pass on returning you the favor — but don’t let that become a habit. Reciprocity doesn’t have to happen in the same sesh, but it should before you offer up that favor again.
  16. Avoid jackhammering. What probably feels best to you during intercourse (deep in-and-out porny thrusting) most certainly won’t feel best to her, especially not during her VFT. Most porn is made for guys, so the subtler moves that many women enjoy don’t often get a lot of air time (plus, they’re often not as visually entertaining). Show her 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.
  17. Teach her about her spots. That is, if she doesn’t know them already. She may, and she should. But virgins often don’t. You don’t want this to turn into a clinical anatomy lesson, but you could seductively name exactly what you’re touching when you’re touching it: her clit,  g-spot, ps-spot. Hey, it’s a great way to find out what areas she likes and how she likes them paid attention to.
  18. Skip anal attention, for now. Intercourse is more than enough to take in. But sometime in the first few weeks, take a shower with her and show her a little anal attention. Don’t go in like gang busters, just introduce her to the idea that she’s got lots of nerve endings back there and that straight people (including you!) enjoy having them stimulated too.
  19. Engange in a good post-coital cuddle. This is a must. Fifteen minutes’ snuggling is just a decent thing to do — and she’s gonna want it, heck she’s gonna need it after this momentous occasion.

Happy boinking!

— Em & Lo

About to take your boyfriend’s virginity? Read:
How to Deflower a Nice, Young Man