A Practical Guide To Popping Your Cherry

This is key. I personally hate the lube in condoms and prefer to buy unlubricated and then slather on some Astroglide, but your mileage may vary. The point is, get something to minimize the friction and your vagina will thank you in the morning.

A word on drinking.

There is an argument for being drunk for your first time, and that is: shit hurts less when you’re wasted. And yeah, if you’re having penetrative sex for the first time, it will probably hurt a little. You’re also (sorry) probably not going to come, so the fact that too much alcohol numbs your clit won’t be that big a problem. That said, we’ve all heard from plenty of after-school specials that alcohol can impair your judgment, and it’s kind of true. More importantly, it’s nice to practice being able to let go of your inhibitions unassisted by substances. So drink if you want, but keep in mind for later that sex is usually best when you’re sober enough to feel something.

Don’t worry.

If you’re concerned about seeming clumsy or inexperienced, relax. You might. But people like sex, and chances are your partner doesn’t give a shit if you elbow him/her in the head or whatever. You’ll probably worry less if you fuck someone you’re comfortable with, and who you know has a sense of humor. I also recommend that you masturbate a lot and learn to look at yourself naked in the mirror and like it. The second one can be a little tough, but luckily the first is easy.

Know yourself.

This is probably the most important tip. Part of having a happy, healthy sex life is knowing what you want, and that can take a little reflection. Ask yourself how you want to feel about the person you have sex with (if the answer is “I don’t care,” that’s fine — it’s just good to ask yourself the question). Ask yourself where you want to be and what will make you feel sexy and relaxed. It’s not that your first time is So Important that everything has to be Just Right — it’s just that with so many other people telling you what to do sex-wise, it’s good to get in the habit of taking a minute to think about exactly what you want.

Losing your virginity in high school or early college can be scary, but at least there’s kind of a cultural script for it. If you’re a little older, though, you may have to write a script of your own. Pinup and guru Von Hottie generously shared with me some options:

Get out of town. Preferably Paris, France. Pick an attractive, mysterious European stranger who doesn’t speak a word of English and is totally inappropriate for your real life, but perfect for this occasion. Wine and dine along the Seine, stroll across a bridge, then drag your man back to your hostel and ask him to teach you the real meaning of l’amour. When they ask you at customs if you have anything to declare, you can proudly proclaim, “Yes, I’m open for business!” International relations will have never been so improved.

Go Primal. Get a bunch of friends together and throw a pagan bacchanal party. Invite several eligible bachelors and wear white robes and a flower garland in your hair. After the wine has flowed freely for several hours, let The Goddess “speak from within” and choose your lover. No man can refuse what The Goddess has decreed, am I right? Bonus points if the whole party leads the two of you in a parade to your bedroom.

Do It the Old-Fashioned Way. Get drunk, get a stranger, get down. Warning: This could be the worst sex you ever have, but that’s okay because it only means it will get better. If anything goes horribly awry, like he loses his erection, or one or both of you gets a nosebleed, just take a break and try again. And this time, get on top.

And last but not least, a word of advice for advanced virgins from former twentysomething virgin KW:

I really only have one tip for losing your virginity in your twenties: The Group Experience. Mind. Gutter. Out. What I’m talking about is the need to have a solid core of female friends to guide you through the first-time sex experience. In my case, it was a gaggle of ladies I met my freshman year at college. We called ourselves the “Restless Virgins”, we read trashy romance novels, had our gay boyfriends teach us about blow jobs (demonstrate in person on bananas…), and we made one another feel better about the fact that we were in our twenties and we hadn’t given it up yet. When I finally gave myself to that “special” boy on the left coast, my girls were on the east planning a cherry popping party, complete with gifts and Madonna songs to welcome me back.

It wasn’t that my first time was traumatic (though it was the first of many experiences with men who were already taken, and therefore, traumatic), it was just that when it came down to it, I was grateful to have women who surrounded me with love, who welcomed me into the next phase of my sexual awakening. Find those women. When you wait until your twenties, it seems like you’re putting something off, or maybe it’s that you waited for this ideal experience and it turns out that after all, it’s just sex, no big deal. Really, you’ll have shared something special with your partner. And if it’s not that special, there will be people who will always love you. And those people should present you with a bowl of cherries, flavored lube, and colored condoms to remind you that a big thing just happened, it was kind of weird, hurt a little, and changed you forever, but also that it will only get better.

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