Zeets called with a dating quandary.

Zeets: I think this girl I’m dating is a virgin.

Me: Isn’t she 27? I doubt a 27 year old living in DC is a virgin. You may as well tell me you found a real Ewok prancing in Rock Creek Park.

Zeets: No, I’m almost 100% positive she’s never had sex. First, she’s from [southeast European country]. She has that Old World culture still in her. And then there’s the way she reacts when I go to kiss her. She tenses up and kind of brushes my cheek with her retracted lips. She acts like a shy 14 year old who hasn’t been kissed!

Me: Are you sure she’s into you?

Zeets: Yes, that’s definitely not it. She has a great time with me, always laughing and smiling. And at the end of the date she asked when she could see me again. If she was truly uninterested she wouldn’t do any of that. No, this girl just has some issues with sex. I can’t believe it. Frustrating. So cute, too.

Me: These are the ballbreakers. The girls you really find attractive who won’t put out. At least with the marginal looking chicks who play hard to get, you can easily cut your losses after the first date. But the hot ones make you linger, hoping against hope she’ll eventually burst like a dam. I’m not sure what I would do.

Zeets: Even a grandmaster pig like yourself is stumped by this problem!

Me: Yeah, but imagine the feeling of accomplishment if you stick it out and succeed. There’s nothing quite like the look of shock on a virgin’s face when you first shove it in. Feliz Navidad!

***

This conversation got me wondering if there is an optimal method for dealing with older virgins and quasi-virgins (those girls who have had sex before in the distant past but remain seriously repressed about the enterprise). I’ve come to the conclusion that the best way to handle virgins is reverse psychology. The older virgin has decades of fantasies and expectations built up in her head regarding sex, so she will feel inevitable disappointment if the reality of her feelings while you are making a move on her stray even the tiniest bit from the feelings she’s nourished in her daydreaming. The way around this conundrum is to shake up her expectations so violently she is left completely at the mercy of her tingle.

Not that I’ve banged a huge number of older virgins in my life, but I can surmise they share a few important personality traits and life histories.

  1. Older virgins (or quasi-virgins) will be more feminine than the average woman. Generally, the more feminine a woman the better she will be at curbing her animal urges. (See: Alias Clio.) This is why lawyer chicks jump into the sack at the drop of a (alpha) hat.
  2. There are good odds the older virgin was molested in some creepy way by a man in her life who was close to her. Maybe her dad sneaked up behind her and licked her earlobe and cackled. Yes, this happened to a Russian girl I used to date.
  3. The older virgin likely has some deep seated issues with her sexuality. Perhaps she’s ashamed of the shape of her labia, or has control issues and the thought of an orgasm fills her with fear. Or, just as likely, she has only been with men who were horrible at sex, and thus has a poor preconception of how sex should feel.
  4. Some man done did her wrong. The quasi-virgin is especially likely to have been the recipient of an emotionally cataclysmic dumping sometime in her past, and has yet to get over it.

Given all the above, the older virgin will be very wary of any man she dates, no matter how much she is viscerally attracted to him. So how to bust through her wonderwall? Your challenges are great, my son, but the reward is exquisite. Successfully nail — and bring to orgasm — a virgin and you will have recruited a love slave for life.

One other important thing to keep in mind: Regular game won’t work as well on the older virgin. This is because the rationalization instinct that so many normal women possess, and which is called upon to justify sex with men who arouse them with tight game, is either atrophied from disuse or missing entirely in the older virgin. The older virgin won’t be able to as seamlessly rationalize her way into bed with you. You, as a man, will find this incredibly frustrating. Women’s rationalization instinct has been the fulcrum upon which all great seducers have leveraged their talents.

So, with virgins you experience a mixed bag of emotions.

Downside: Blue balls.

Upside: Loyal girlfriend.

If you think ten dates in a row without sex, and the possibility that a ten date investment might never result in sex, is worth enduring for the prize of a loyal girlfriend, then you need a specialized virgin-be-vanished strategy. This strategy is powerful in its simplicity: You play the role of the woman. Role reversal when the threat of sex enters the picture will cross her wires and short circuit her expectations. An example would be when you go in for the kiss and she purses her lips tightly for a dry pucker, you pull back first and say, without sarcasm, “MmmMmm, this is hot. We’d better not go any further, I want it to be different this time.” The idea here is to draw a contrast between your words and your actions. (Contrast is king!) You are verbally expressing pleasure but nonverbally pulling back as if you were the virgin with doubts.

But don’t get carried away with the role reversing. At some point you will need to man up and gradually escalate to bolder moves. The risk of role reversal game is that the virgin will slowly lose respect for you, as her hindbrain begs for you to take action while her forebrain begins associating the negative feelings of delayed sex with your company.

If played properly, role reversal game will break a virgin’s willpower, and the dam will gush forth at the most unexpected of times. Timing and feedback is everything. Don’t expect a shortcut to sex with the older virgin. You will need to put in more time with her than you would with a sexually liberated woman. The great risk is that each new sexless date erodes the fascination she feels for you, and the chance that her initial attraction surrenders to the dictates of her repressed vagina.

Role reversal, escalate, pull back, escalate some more, pull back a little less. Repeat ad phalluseum. This is the virgin-killer template.