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Keep that attitude and they’ll be able to help you through it and probably ease a lot of your concerns. You keep picturing your girlfriend/boyfriend having sex with some other person — doing all of the things you’ve waited to do for so long with somebody else, as if it’s nothing — and it’s like knives through your heart. But so much for that, because now they’re gone, and you’re faced with the prospect of dating somebody who was nowhere near as good as them and has a sexual history that is five times as bad. To some people who are waiting till marriage, the virginity-factor can be all-consuming when picking a boyfriend/girlfriend.

That’s when issues like those mentioned above are going to come into play.Maybe they have slept with a couple of people but only in committed relationships. If you’re a virgin who regularly dates non-virgins, then you’re going to date people who have all kinds of sexual histories.Maybe they waited for a while but recently started having sex. Some may have balance factors, and some may be completely unbalanced with you (read: lots of torrid sexual history, compared to you).Sometimes this is played straight, but (particularly when the crossdressing is Played for Laughs) it's often a case of Informed Attractiveness.In such scenarios, despite the "new woman" looking mannish and homely to the audience and most characters, someone will unaccountably be smitten with "her." Hilarity Ensues as the crossdressed hero tries to fend off the advances of an unwanted suitor.

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