Ask Debby Herbenick - tips for virgins

Pink lube

Q: Like several readers who wrote over the summer, I’m a virgin. A female in her mid-twenties, to be exact. While I’ve been sexually active—giving/receiving oral sex, manual stimulation and, yes, even playing around with the ol’ vibrator—I’ve never had penetrative sex. Alone or with a partner, I enjoy inserting my vibrator, with no sensation of discomfort. I’m not exactly worried about a penis hurting me, per se, but I have been told by multiple girlfriends that the first time is not usually that pleasant. Can you recommend a good position to lose one’s virginity? Is it better to go the standard missionary route or do girl-on-top? Both have been suggested by helpful pals. Thanks ever so!

A: The first time that a woman has sex is uncomfortable or painful for some, but certainly not for all women. It may not hurt you at all if you are with a typical-size guy (e.g., five- or six-inch-long penis), feel relaxed and comfortable with yourself and with your partner, and use lube (if needed). For one, your body is already used to penetration from a vibrator, so—vaginally speaking—you’ve already paved the way for a penis. Another huge factor related to physical comfort is emotional comfort. The fact that you’ve had oral sex and have played with a vibrator with a partner suggests to me that you have some level of comfort being naked and up close and personal with a partner, and perhaps even talking about/showing your partner what feels good to you. These go a long way when it comes to intercourse.

That said, there is no “best” position for first-timers. An advantage with being on top is that you can control how much penis you take in as well as the pace. An advantage of being in missionary (on the bottom) is that it may involve less deep thrusting and you can relax your body while your partner enters you. There are pros and cons to each and there are dozens of other possible positions as you gain experience. If you’re not well lubricated, either because you’re on allergy meds, nervous or whatever else, slow things down—foreplay can increase your natural lubrication—and don’t be afraid to add your own lube (I like Sensua Organics and Just Like Me) to your vaginal opening and/or his penis. Assuming you plan to use a condom, slather the lube on the outside of the condom (not directly on his penis) to reduce the risk of condom slippage. Lube application, by the way, doesn’t have to be awkward. In fact, lube time can be fun and very sexy. It’s a great excuse to touch each other’s genitals or to watch your partner touch his own while you touch your own. Also, talk about sex before having it—what you want to try, as well as reassurance that you want to give it a go but that either of you can stop and switch to oral sex, vibrators, kissing or cuddling if you want—and go from there. Though I don’t know you, it sounds like you have a great starting point in terms of experience and comfort, so have fun. If you want a good overview from a book, my all-time favorite is The Good Vibrations Guide to Sex (Cleis Press, $25.95). And finally, don’t forget to have fun—with all the scary messages about sex out there, sometimes people forget how amazing, connecting and enjoyable it can be.

Q: Just received my first issue of Time Out Chicago and am impressed with your column. Thought your penis poem [“In & Out,” TOC 54] was keen, yet I have a wonderful feeling that it wasn’t complete. Not to sound obscene or suggestive, but one aspect of your description that was missing was color! I know a number of white women who prefer their men’s penises to be of the darker hue. I’m not black but I find myself enthralled by interracial couples. I would have written a long letter or poem to you—I still may do so, if you prefer—but I think this is one aspect of sexuality that is oft left to “midnight” hours or abnormal behavior! What say you, lass?

A: I want to hear more! Letter form would suffice, but a poem would be even better. I’m glad you’ve started subscribing to TOC—and that you’ve so quickly devirginized yourself by e-mailing me!

Q: I am sensitive everywhere, including my vaginal area. When I told my doctor that I have had itching with certain lubricants, he suggested olive oil as a lubricant. I was surprised for two reasons. First, I think of olive oil as a cooking—not a sex—product. Second, I thought that oils were unsafe to use with condoms (which I use), but he said it was fine. What have you heard?

A: Though I can understand why olive oil brings to mind a sauté rather than sex, health-care providers frequently recommend olive oil as a lubricant, as it appears to be less irritating for some women. However, olive oil—like other oil- and petroleum-based products—is not compatible with latex condoms and may cause condom breakage. This has been demonstrated in research, and yet somehow the myth that olive oil works with condoms persists. If you want to try olive oil, consider using polyurethane condoms. Otherwise, keep your latex condoms and consider woman-geared lube, like Pink or Sensua Organics.

Send letters to Debby Herbenick, MPH c/o Time Out Chicago, 247 South State Street, 17th floor, Chicago, IL 60604, or send e-mail to inandout@timeoutchicago.com.