young teenage couple

I’m 27 and dating a lady who is 28 and a virgin. I’ve never been with a virgin before. How do I go about having sex with her so she enjoys it and doesn’t bleed or get hurt?


  • Michael Castleman says:

    It’s usually called “deflowering.”

    What’s vaginal intercourse like the first time for women? That depends. Reactions range from awful to fantastic. It all depends on the two of you and how you make love. Even if you’re sexually experienced, the first time with any new lover raises many of the issues involved in making love with a virgin. It doesn’t matter whether it’s her very first time, or your first time with her. These suggestions should help maximize pleasure and satisfaction for both of you:

    Make sure she really wants to. According to the 1994 National Health and Social Life Survey, about one-third of women recall not wanting sex their first time, or feeling forced into it. Sexual coercion is wrong and my be criminal–not to mention that it’s a one-way ticket to lousy sex. Even when a woman consents to her first sexual experience, an estimated “75 percent feel unprepared,” according to the late sex researcher and therapist Sandra Leiblum, Ph.D., “and find their initial sexual experience distasteful. Young Romeos, even those who care deeply about their girlfriends typically lack sexual skill or finesse.”

    Plan it in advance. Virgin women (and men) are often unprepared for their first sexual experience–and often many subsequent ones–because they typically “just happen” in the heat of the (often-intoxicated) moment. Planning substantially reduces her risk of pain, and shows that you care about the quality of her experience, which helps her relax. This enhances the experience for both of you.

    You mentioned not wanting her to bleed. The myth is that first intercourse hurts women because it tears the hymen, the membrane that surrounds the vaginal opening in newborn girls. In the vast majority of women, ordinary activities wear it away by age 5. But some women have tough, persistent hymens. Ask about hers: Can she use tampons comfortably? If so, this suggests that what’s left of her hymen, if anything, probably won’t be much of an impediment her first time. But if she has trouble using tampons or can’t, then urge her to consult a physician before you attempt intercourse. She may need to have her hymen removed surgically (hymenectomy).

    As part of your planning, discuss contraception and prevention of sexually transmitted infections. If you have questions or concerns, visit a family planning clinic together. Doing this enhances sex. Great sex depends on mutual comfort, trust, and relaxation. Many women find it difficult to relax with men–and respond sexually to them–if they think you don’t care about their health or pregnancy risk. A good lover raise these issues beforehand.

    Gently explore the kinds of sensual caresses she enjoys. Before you make any move toward intercourse, allow her plenty of warm-up time. It take most women considerably longer than men to feel receptive to intercourse. Embrace her, kiss her, and massage her all over for at least 30 minutes before asking her to spread her legs.

    Use alcohol and other drugs in moderation, if at all. First times–or first times with any new lover–cause anxiety. Many men wonder: How far will she let me go? Many men also have difficulty saying: “You really turn me on. I want to make love with you.” Drugs, particularly alcohol, are an easy out. After a few drinks, it’s easier to coax a lover into bed. But alcohol is often bad for sex. It’s a central nervous system depressant that interferes with men’s erections and ejaculatory control, and with women’s sexual responsiveness and ability to express orgasm. In addition, good sex involves emotional presence, being fully in the moment with your lover. Alcohol removes you from the moment. A drink or two can be fun before sex, but try to hold the line there. You’ll enjoy sex more if you’re not drunk. Use other drugs sparingly as well.

    Provide reassurance. Just as you want to please her, she wants to please you–and wonders if you’re enjoying sex with her. If you are, say so periodically throughout your lovemaking.

    Consider lubricant. Most young women self-lubricate well, that is, as sex proceeds, their vaginas become wet. But some don’t, and even for those who do, extra lubricant can make sex more enjoyable. Lubricants are available over-the-counter at drug stores. They’re usually displayed near the condoms.

    If anything goes awry–if you come quickly, or if your erection falters–don’t flip out, and don’t blame the woman. Accept the situation gracefully. Just laugh and say something like, “I get a little nervous with a new lover.” Or: “You get me so excited, I can’t control myself.” With any lover, good sex takes practice and experience. Virgins are, by definition, inexperienced, so things may not go as smoothly as you’d like.

    Don’t expect her to have an orgasm her first time–or her first several times. “Sexually inexperienced women are not reliably orgasmic,” Leiblum notes. Even if you plan her first time well, go slow, and enjoy extended total-body sensuality with lots of lubrication and plenty of gentle, clitoral stimulation, she may feel too anxious to have an orgasm. Accept this, and reassure her that it often takes women several times–or longer–to feel comfortable enough with sex to express orgasm. Then invite her to masturbate to orgasm while you hold her close.

    For more information, read these articles: Caressing Women: Tips for Men,, and Orgasms During Intercourse – Improving Women’s Chances.

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