Has there actually been research into any of this, or is it all anecdotal? Not that the anecdotes aren’t revealing in themselves…
I know a fair number of 30-ish probable virgins, i.e. women who their friends say have never had a boyfriend. The 20-year olds are used to the internet, so the shy ones can work up the nerve to meet some anonymous stranger for a little no-strings rumpy-pumpy. The 30-year olds have thought of it, but are prevented by inertia.
Defloration is an art. Make her relaxed, go SLOWLY, and let her pull you in, millimeter by millimeter. There should be no pain for you, the deflowerer…at least not this early in the relationship!
Screaming Jesus’s Guide to Hymen-Rupturing
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Make sure your sweetie is comfortable and relaxed. Ply her with liquor. Tell her you’re sterile, promise to maybe marry her.
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Remember that this should be a beautiful, emotional time. Gaze lovingly into her eyes and lie to her. Hold her tight, in case she comes to her senses and tries to wiggle out of your grasp.
(This is why the missionary position is so popular for first-time lovers–your weight helps pin her down.)
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Never mind condoms. They don’t feel good, and besides, you can’t get pregnant the first time. (If she does, then make sure you’ve given her somebody else’s name–like that asshole who jerked you around at your embassy!)
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If she is a Christian, you can add to her sense of boundary-transgression by shouting “Hail Satan!” and making the sign of the devil while astride her. If she is a Buddhist or Jewish, tell her you’re going to make her scream for Jesus.
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Subsequent sex should be much more relaxed and fun. Tell her to wait for you in your room, with the lights out, then send in your friend instead. (Your friend meanwhile does the same for you.) That way nobody gets too clingy about the relationship.
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If her parents barge into the room, have a ready explanation for what you’re doing.
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Look beyond shallow, superficial standards of beauty. Consider bonking a fat chick or an ugly girl–they feel just the same on the inside.
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Remember, some states have a special category under statutory rape for retarded chicks.
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Foreplay, including generous amounts of oral sex, is very important. If she seems reluctant, go into the bathroom and pretend to wash it first.
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Use a natural-based lubricant, such as spit.
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Finally, if your date is not a virgin, all is not lost. Flip her over and YEEEEEEEEE-HA!.