In & Out

Q I really like the guy I’m dating and we’ve been talking about having sex, which neither one of us has ever done before. How do I know when I’m ready to have sex?

A As much as many people would love a “ready for sex checklist,” no such thing exists—though Heather Corinna’s book S.E.X. (DaCapo, $17.95) discusses the issue in helpful detail. What often works, though, is taking some time to consider whether this is the right time, situation and partner for you. If you don’t want to get or pass a sexually transmissible infection (STI), you should both get tested for STIs, including HIV, together—and use condoms, which can greatly reduce the risk of some but not all STIs. If you aren’t ready to become parents, make sure you’re using an effective form of birth control: Use condoms plus another form of birth control (e.g., withdrawal or the pill) if you’re a male-female couple. You might find yourself asking whether your partner is someone you not only feel attracted to but like and trust. Is he someone you feel safe with, physically as well as emotionally? Can you communicate about sex well enough that you can tell him what you want or need from sex (Lots of foreplay? A certain position? Rose petals? Pleather?). Make sure you have fair expectations of sex, too. Many guys experience premature ejaculation or erection difficulties their first few times—mainly because they’re nervous, and many women need time to learn to orgasm—so be kind and compassionate with each other. For further information about STI testing and birth control, check out plannedparenthood.org or call the Chicago Department of Public Health’s Lakeview Specialty Clinic (2861 N Clark St, 312-744-5507). For sexual health care, in addition to Planned Parenthood, you might also check out Howard Brown Health Center (particularly for gay, lesbian, bisexual and transgender health-care issues; howardbrown.org) and the Chicago Women’s Health Center.

Q Everyone talks about prostate play like it’s the holy grail for men. Is it really that great?

A There is no one type of sexual stimulation that everyone likes. Some men enjoy prostate stimulation (also called p-spot stimulation), others can’t stand it. And although some people think that prostate play is mainly for gay men, all men—regardless of sexual orientation—may find prostate stimulation pleasurable. You can stimulate the prostate externally by pressing on the area between your scrotum and anus (the “taint”) or internally by using fingers, a sex toy or a penis to stimulate the area. Just please don’t insert vegetables, shampoo bottles or any other foreign objects into the anus. For more information on prostate play, check out The Good Vibrations Guide to Sex (Cleis Press, $25.95).

Q I’ve always been vibrator-curious but never tried one, mainly because I was terrified my mom would come across it when I lived at home. Now that I’m living away from my parents, where can I get a vibrator in this town?

A Well, aren’t you in for a treat! Welcome to the world of sex toys. Lucky for you, you’re living in a sex-toy friendly town with many terrific shops. My favorite local shops include Early to Bed (5232 N Sheridan Rd, 773-271-1219), g boutique (2131 N Damen Ave, 773-235-1234), the Pleasure Chest (3436 N Lincoln Ave, 773-525-7151) and Tulip (3448 N Halsted St, 773-975-1515). You and your friends might also arrange for a sex-toy party through one of these shops, during which one of their educators can come to your apartment or dorm and you can check out various vibrators before you buy. To learn about how to shop for sex toys, how to use them alone or with a partner, how to clean them and what lubes go best with which toys, check out my book, Because It Feels Good: A Woman’s Guide to Sexual Pleasure & Satisfaction (Rodale, $21.99).

Q When does a guy’s penis stop growing? When is it his “full adult size”?

A For many men, their penis stops growing somewhere around age 17, though it does vary. Although many people fear that size matters—and penis size does matter, to some degree, to some women and men—it tends to matter less than one thinks. To be great at sex, make sure to focus on the psychological excitement and intimacy, communicate with your partner about what feels good for him or her, and patiently and compassionately listen to what partners ask of you.

Q I didn’t lose my virginity before college. How old is too old to be a virgin?

A There is truly—and I mean this—no perfect age to lose one’s virginity. Plus, virginity means different things to different people. Some define virginity as not having done anything sexual at all, and others define it as having abstained from vaginal intercourse, even if you’ve done all sorts of other things (e.g., oral or anal sex). To better situate yourself for a pleasurable sex life, choose to have sex when you feel ready and not when you think you “should.” At the same time, don’t worry about it being the one-hundred-percent perfect situation: No one is perfect and we are all doing the best we can. Instead, seek sexual experiences that are likely to be pleasurable, comfortable and that fit with your personal values.

Q How can a woman learn to have an orgasm? I’ve never had one and I’m 22. I was hoping to have one some time before graduation.

A This may be your lucky year! Nearly all women are capable of orgasm, although it can take time—weeks, months or years of practice and patience. Several books have sections about learning to orgasm, including For Yourself (Signet, $7.99) and Sex for One (Three Rivers Press, $14). A third book, Becoming Orgasmic: A Sexual and Personal Growth Program for Women (Fireside, $16), is completely dedicated to the topic and has been found to be as effective as sex therapy in terms of helping women learn to orgasm. Some women find that using a vibrator helps them experience orgasm more easily than finger stimulation or partner sex. Although being goal-oriented is a great strategy for college and the work world, it often doesn’t work as well for female orgasm. Sometimes women focus so hard on orgasm that the stress and pressure make it more difficult to orgasm. Focusing on having a more mutually pleasurable sexual experience together, for sex that involves a partner, has a better chance of resulting in a woman’s orgasm.

Read Debby Herbenick, Ph.D., every week in Time Out Chicago, or find past In&Out columns at timeoutchicago.com/inandout.