Q: I am a healthy female in my mid-twenties and as of yet, have only had orgasms when using a vibrator (either masturbating or during sex). I tried manual masturbation for years, and guys I’ve dated have tried various techniques during foreplay and sex, but I have not been able to reach orgasm. I don’t have any bad experiences with sex/sexuality in my past (abuse, rape, parents indicating sexuality was bad). In fact, I’m very comfortable with my body and really enjoy my sexuality. Within the past few months, I’ve begun dating somebody and this issue has come up on a few occasions. Initially, he was unfamiliar with using vibrators, but he’s now comfortable with it and, in fact, it turns him on. However, I’d still like to experience an orgasm with him minus the vibrator. He’s really good about stimulating me in other locations (clitoris, nipples) when we’re having sex. However, it doesn’t seem to get me there. Any suggestions?

A: Absolutely. My first suggestion is to consider reading Becoming Orgasmic (Fireside, $15), which has shown to be highly effective in helping women learn to have orgasms. My guess is that you can probably learn to have orgasms in other ways, though it may take time and patience. And I mean tons of patience. That’s because the more you put pressure on yourself to come a certain way, or the more your partner pressures you whether he means to or not, it will make it a hundred times more difficult to orgasm. Similarly, some women and their partners stumble with orgasm because they focus so much on the goal (orgasm) and less on the journey (pleasure). Trying out various sexual techniques with a focus on what feels good rather than what will get you “there” can be monumentally important. When you’re having sex, go with what feels good and try letting go of expectations or an attachment to the outcome (it’s very Zen-like, really). Manual stimulation can be difficult when it comes to orgasms because it tends to take so long (sometimes as long as 45 minutes to an hour) for women to orgasm. Oral sex can also bring about orgasm for many women, particularly if they are comfortable with their body and feel positively about how their genitals look, smell and taste. Then again, it also takes a partner with decent technique and your ability to provide feedback (e.g., “I like it the most when you lick right here” or “it feels awesome when you do a fast flick with your tongue” or “I need you to maintain the same pace”). You also might be in a vibrator rut. Don’t blame your vibrator, though. This happens with hand masturbation, oral sex and intercourse, too. Often when we find things we like or that work out well for us, we do the same thing over and over again, thus training our bodies to respond specifically to that type of stimulation and perhaps not as well to others. Switching it up, however, can prepare your body to respond to a wider range of behaviors, and that can open new worlds of pleasure and orgasm, so play around a bit.

Q: Even though my issue was delivered just today, I’m going to guess I’m the million and first person to e-mail you asking for more information on stimulating the vagina [In & Out, TOC 76]. Do you have a book, or one that you recommend? I bought The G Spot by Alice Kahn Ladas, Beverly Whipple and John D. Perry, which I still have yet to finish (it’s not exactly train-commute material, plus I usually bike), but from what I’ve read, it dealt a bit on the psychological aspects of sex. I appreciate the information. Thank you!

A: I beg to differ, The G Spot (Owl Books, $15) is definitely train material—and keep reading, because it gets into very handy physiological-related info as well. What better way to liven up the work commute, make friends and demonstrate to the world that sexuality is a normal part of everyday life than to bring along a sex book? Some of my own past train/plane material has included Female Ejaculation & The G-Spot (Hunter House Publishers, $16) and The Good Vibrations Guide to Sex (Cleis Press, $26), both of which I’d recommend. I bring them along simply because it’s a good time for me to catch up on my reading, and since I work in the field of sex research and education, I tend to forget that these topics are so taboo to others. If I notice discomfort, I hide the title. But I find that many people (and not just weird stalker types) strike up interesting conversations with me about sex books, such as a woman who was curious about my interest in reading Sex for One: The Joy of Selfloving (Three Rivers Press, $14); it turned out she had read the original version back in the day, when it was first published. As for other forms of vagina love, some women enjoy Kegel exercises more while using Ben Wa Balls (www.pureromance.com). Having a tongue on or near one’s clitoris at various speeds and pressures can be exciting, too, but preferred techniques vary by woman. Some ladies love to have their labia majora (outer vaginal lips) massaged, which may stimulate the inside parts of the clitoris. And during intercourse, women can stimulate the G-spot by tilting their hips upward so that their partner’s penis or sex toy puts pressure on the front wall of the vagina. It’s total bliss.

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.