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My Magazine > Editors Archive > Advice > Tales of Hymen
Tales of Hymen   by Geoff Smullins

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More than one man has asked, "Are you sure you were a virgin?" after servicing a lady to her first fuck. That's because he's heard the stories, the very long mythology that has invented a woman's first time as something dramatic, even traumatic. As the story goes, the woman experiences pain, more pain, a pop, and then a puddle of blood. In many older cultures blood had to be found on the marriage sheets for the marriage to be considered valid (and blood was often smuggled into the wedding chamber by the bride to ensure the expected would happen). Even these days, guys expect a similar scenario from their virgin partners, and many who don't find blood or whose lovers don't experience pain start to wonder if she was really a virgin. But the first time does not have to be painful, nor does it always result in blood. In fact, when neither of these things happen, it's just as likely that the man has done it right.

The truth is, if a guy really wants to know his lady's a virgin, he should inspect her vaginal opening before, not after, they have sex. The hymen ("cherry") is a bit of skin around the vaginal opening. It's flexible; it can stretch. And it's shaped differently in every woman: some are large and cover a lot of the opening; some are small or cover very little of the opening. Some are virtually not there. So the first myth is that this "membrane" (as it's called) covers the entire opening and must be pierced in order to have sex. Closer to the truth is that when you go to penetrate the virginal opening it will feel like a very tight fit to both of you. She will feel something stretching tightly, and, as your penis makes its repeated pokes at the opening, or if you're lucky enough to penetrate slowly and continue to move your penis deeper, shallower, deeper, the hymen is not pierced but rubbed away.

Because the hymen can stretch (think how the skin around a penis must stretch every time a man gets hard), a woman's first time can happen smoothly as long as both partners make sure a few things occur:
1) You both proceed very slowly
2) You both use plenty of lube
3) He concentrates on maintaining her arousal (that is, more foreplay; keep her hot).
4) He lets her call the shots (just as in anal intercourse -- the person being penetrated calls the shots due to the delicate nature of the anus).
5) He tells her early on that she's calling the shots. Let her know that her vagina's first taste of dick can be pleasurable. Tell her you want to make that happen and she can help by letting you know when to stop (when she's feeling discomfort) and when she's ready for you to start again (when you've got her all horned up again).
5) He starts out small -- insert a finger or a bullet vibrator, into her hole -- and works his way up: several fingers, a g-spot dildo, and finally his penis.

Her calling the shots means that if she starts to feel pain, the guy should back off. He should shift his focus from trying to penetrate to getting her more aroused. This is the same sort of approach you'd use for anal intercourse (see our "Sexpert's Corner" category in the article titled "Bigger, Longer, Thicker 2" in which Tristan Taormino talks about the 10 key ingredients of anal sex).

At this point, the guy who succeeds at painless virgin penetration has a mindset made of 2 ingredients:
1) He is totally focused on getting the lady hot and keeping her that way.
2) He is confident that painless entry will come if not sooner, then later.

Her first time should be all about her. Though he's concentrating on opening up her pussy and relaxing her vagina, he should not forget that she has other knobs and buttons that love foreplay -- like nipples and lips. Distract her from time to time by lavishing attention on her tight little nipples. As you suck her nipples or kiss her lips, you can play with her pussy using your hands. The more horny you get your virgin, the more her genitals are going to swell and expand, and the more wet she'll be. The wetness helps to keep her virginal hole lubricated and ready for your entry. But don't feel obliged to remain "all-natural" in the lube department. There's nothing wrong with adding a little pharmaceutical lube to her natural juices before going in.

According to Michael Castleman in Sexual Solutions: A Guide For Men and the Women Who Love Them, lubrication (or its lack) is the major reason intercourse -- any intercourse, virginal or not -- is sometimes painful. "Like all living tissue, a moist hymen is more pliable than a dry one," says Castleman. "A moist hymen can stretch. A dry one is apt to tear and cause pain."

As in ass play, some people will have a successful entry the first time they attempt it, others need to call it a night and pick up some other night where they left off. It does get easier. In this respect, hymen are like assholes -- no two are the same. Some can be bypassed easily on the first attempt, others take several sessions before a smooth, painless entry comes about. Patience is your most valuable tool.

Each time you approach the virginal pussy there should be a rhythm to your moves: arouse her, tease her, knock gently at her pussy hole, retreat; arouse, tease, knock, retreat. If you follow this pattern, taking the slow road through foreplay, you'll find that each time the head of your dick knocks at her moist hole, she's wider, more flexible and more receptive. Eventually, her untried opening will let you in, smooth, tight, and painless.

Happy cherry popping.