The Virgin’s Guide to Happily Losing It

Many people have regrets about their first time. Here’s how to avoid that.

• The Fundamentals of Sex
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Conventionally, a heterosexual virgin is a person who has not had penis-vagina intercourse (PVI). Our cultural focus on losing virginity implies an either-or situation—virgin or not. Actually, sexual initiation usually involves a gradual escalation of erotic play that, for able-bodied heterosexuals, culminates in PVI.

Know Your Limits

Absent coercion, erotic escalation usually includes four milestones:

• Above the neck: kissing, then deep kissing with tongue play.
• Above the waist: breast play with young women fully clothed, in bras, or topless.
• Below the waist: handjobs, oral sex.
• PVI.

As you ride the sexual escalator, some suggestions:

• Play solo. If you already self-sex regularly, carry on. If not, consider more solo sex. Masturbation is our original sexuality, the foundation of enjoyable partner sex. If you’re uncomfortable making love with yourself, it’s difficult to enjoy it with anyone else.
• Consent. You’re never under any obligation to do anything you don’t want to do.
• Review the ingredients of great sex. See my previous post on the subject.
• Know your mind. If you have limits, be clear about them, and enforce them.
• “Let’s have great fun going this far.” Once you’re clear about your limits, speak up. “I enjoy doing A. I’m nervous about B—let's discuss it. And for now, I’m not into C.” If you’re assertive, you gain valuable experience in sexual negotiation. You also learn if your partner respects your boundaries. If you feel pushed beyond your limits, perhaps it’s time to dump Mr. (or Ms.) Pushy. Another advantage of speaking up: It proves you’re not a tease. “I never teased you. I told you exactly how far I’d go. Weren’t you listening?”
• Attention, initiators. At every step, ask, “Is it okay if I—?” Asking shows you value your partner. It also slows the pace. Many young women complain that young men rush things. Slowing the pace allows young women the time most need to become erotically aroused and responsive. Of course, it’s no fun to feel highly aroused and have a partner say, “Stop.” But life involves disappointments and maturity involves accepting them. If you stop when asked, you just might get a “yes” down the road. If you don’t stop, you’re a jerk and possibly a rapist.
• “Take my hand in yours.” Gentlemen, if porn is your model for caressing women, your girlfriend may recoil from touch that’s too rough. Unless specifically requested otherwise, touch her gently. Keep lubricant handy and use it. Place your hand in hers and say, “Show me how you enjoy being touched.” The same goes for cunnilingus. In porn, the men lick like machine guns. Ask for coaching.
• When young women push young men. Boys should deal with aggressive girls the same way girls should deal with pushy boys. Be clear about your limits. Resist coercion. Have fun within your comfort zone. If you’re prude-shamed, say, “Sorry, I’m just not that into you.”

How to Lose It, Happily

Our culture makes a big deal of losing virginity. But it’s often over in a drunken flash and bells don’t ring. Suggestions:

• Have you been sexually abused? If you’re among the 15 percent of girls and 2 percent of boys with abuse histories, you can recover and enjoy great sex. However, abuse complicates lovemaking freely chosen. If you haven’t already, consider psychotherapy to recover from your sexual trauma.
• Ladies, check your hymens. Can you insert tampons and lubricated fingers comfortably? If not, PVI may feel uncomfortable, painful, or impossible. Consult a gynecologist. Minor hymen surgery may be necessary.
• Admit your virginity. As love-play moves below the waist, I encourage virgins to admit it. The best sex requires deep relaxation. Lying creates stress that impairs pleasure. Coming clean usually enhances first intercourse. If you admit your virginity and your partner is reassuring, you can relax, which enhances sex. But what if you’re prude-shamed? Say: “I could have done it. But I wanted it to feel special and it never did, until now.”
• Limit alcohol. During first PVI, many young people are blotto. Bad idea. Sex while drunk may impair erection and ejaculatory control in men, clitoral sensitivity in women, and pleasure and orgasm in everyone. Alcohol use by either men or women, also raises women’s risk of sexual assault, especially when both are drunk. Don’t do it drunk. Limit alcohol, or consider cannabis. Two-thirds of lovers consider it sex-enhancing. And compared with booze, it’s much less associated with sexual assault.
• Carry condoms. Use condoms your first time and every time—until you both commit to monogamy. Many women underestimate men’s willingness to use condoms. That’s what Australian researchers discovered in a survey of 819 young adults. Increasingly, young men are fine with condoms. If not, ladies, say, “Either you do, or I don’t.”
• Use lubricant. Even if the first intercourse is consensual, anxiety may reduce young women’s vaginal lubrication, causing discomfort or pain. In seconds, saliva or commercial lubrication make PVI more comfortable.
• Consider the setting. Gentlemen, most women appreciate romantic settings: candlelight, music, flowers, and clean sheets. Show her you’re willing to expend effort on her. If you make her feel special, the sex is more likely to feel special.
• Schedule it. For most first-timers, sex just happens. You drink too much and, suddenly, you’re doing it. For a satisfying first time, schedule it. Many people object to scheduled sex. They say “Spontaneity is more romantic.” And: “What if I’m not in the mood?” Being in the mood is rarely an issue for horny teens and young adults. And who says scheduling isn’t romantic? Most couples schedule their weddings well in advance. Scheduling creates anticipation, which aids arousal, and allows time to assemble condoms and lube, arrange music, and change the linen. Sex therapists recommend scheduling sex in advance.
• Review the basics. See my previous post on the ingredients of great sex.
• Coach each other. Everyone is sexually unique. Never assume you know what your partner wants. Ask. And don’t assume your lover knows what you want. Speak up.
• Don’t expect women to orgasm during intercourse. Almost all men can have orgasms during PVI, but among women, only 25 percent are consistently orgasmic that way—no matter how large the erection, how long the sex lasts, or the depth of the couple’s love. PVI doesn’t provide what most women need for orgasm—direct, gentle, extended clitoral caressing.
• Never expect simultaneous orgasms. In Hollywood sex, he pumps a few times and both peak. Actually, simultaneous orgasms are rare. Only 25 percent of women are consistently orgasmic during intercourse and even fewer at the same moment as their men. Take turns helping each other work up to orgasm.
• Laugh. There’s humor in joining genitals. Try to laugh off little difficulties. You’re young. You have decades of sex ahead of you. Keep the mood light.
• Afterward, cuddle. After mutual orgasms, cuddling increases sexual satisfaction, especially for women. A University of Toronto study shows that small increases in post-coital cuddling substantially boost couples’ sexual and relationship satisfaction.
• When do you become “experienced”? The number of times you’ve done it doesn’t matter. You’re experienced when you both consistently enjoy pleasure and help each other work up to orgasms.

• The Fundamentals of Sex
• Take our Romantic Personality Test
• Find a sex therapist near me

Edwards, G.L. and B.L. Barber. “Women May Underestimate Their Partners’ Desire to Use Condoms: Possible Implications for Behavior,” Journal of Sex Research (2010) 47:59.

Lieblum, S. and J. Sachs. Getting the Sex You Want: A Woman's Guide to Becoming Proud, Passionate and Pleased in Bed. Crown, NY, 2002.

Lynn, B. et al. “The Perceived Effects of Marijuana Use Before Sex,” Journal of Sexual Medicine (2017) 14(Suppl. 5):e357.

Muise, A. et al. “Post-Sex Affectionate Exchanges Promote Sexual and Relationship Satisfaction,” Archives of Sexual Behavior (2014) 43:1391.