Ask Debby Herbenick | Why is it so hard for women to orgasm, and so easy for men?

Answers to your most penetrating sex questions. This week: unfair orgasms, clean(er) anal sex.

Q It's so unfair that men can always get off during sex and women can't do it so easily. I've never had an orgasm from sex and I feel pitiful having to take my vibrator out to have an orgasm after he's done and I'm still left hanging. Why is it so hard for women? I feel like it's not just me, because some of my friends have problems with orgasms too-but it really frustrates me! Will I ever be able to have an orgasm the normal way?
A Okay, a few things. First, life is not fair and neither is sex. Get over it. Second, not all men can ejaculate easily during sex—and I’m not even talking about the 78-year-olds (see below). A small but important minority of men take a very long time to ejaculate (delayed ejaculation) or find it practically impossible to do so (inhibited ejaculation). Third, at least you can have an orgasm. I’m a glass half-full/vibrator batteries half-charged person. You, my dear, sound like a glass half-empty/batteries half-drained person. Fourth, taking a vibrator out for your orgasm is not pitiful; it’s resourceful. I admire it. And many men are thrilled to find a woman who’s resourceful and comfortable enough with her body and her sexuality that she’s willing to add a vibrator to their sex play. Okay—after saying all that—I get it, I really do. I hear from women all the time who want a more effortless orgasm, especially during intercourse. A more organic orgasm, even, one that doesn’t require careful positioning or finger play or a battery-powered device. Happily, chances are that one day you will have such an orgasm. Most women are capable of experiencing orgasm during intercourse. Stressing over it doesn’t help, as stress is the enemy of orgasm. Chasing orgasm doesn’t help, either, though focusing on pleasure seems to: trying positions, fantasies, and ways of engaging with each other psychologically that bring you pleasure. The more you focus on pleasure, the more likely you are to stumble upon something that you want more and more of. And trying more and more of that thing might end up pushing you over the orgasmic edge, though it can take time. Relaxing can help. Practicing Kegel exercises (squeezing and releasing the pelvic floor muscles) may help as well, both during sex and at non-sexy times of the day. If you need to feel immensely in love, try to create more loving intimacy during sex. If you get off on power (either wielding it or submitting to it), then play with that. And if your chief complaint is that the orgasm comes from a toy and not your partner, then get your partner in the game sooner by asking for stimulation via oral sex or finger play, if you’re able to experience orgasm that way. These are all “normal” ways to experience orgasm—in fact, more common than vaginal intercourse for many women. So it doesn’t get much more “normal” than that.

Q We’re a European couple staying in Chicago this winter and we’d be thankful for any tip to encounter some erotic tension, from a burlesque show to swinger clubs. What options are around?
A Although every town has its sex-things-operating-illegally, and I’m probably not allowed to promote illegal activity (such as masturbation massage parlors or other paid sex work), there are plenty of sexy legal things going on in Chicago as well. You mentioned burlesque, for example, of which Chicago has an enormous variety. Check out Michelle L’Amour (“The Ass That Goes Pow!”; see chicagostarlets.com for her and other starlets’ schedules) and who I’ve had the good fortune to watch dance, tease and twirl on several occasions, wondering how she so effortlessly hides her privates behind careful whisks of her feathers (teach me, Michelle!). Also, local sex boutiques Early to Bed, The Pleasure Chest (thepleasurechest.com; select the Chicago location), Tulip and g Boutique offer a range of workshops, from better blow jobs to pinup photography sessions. They also, of course, sell sex toys, lubes, massage products and other delights. Dig through leather shops on Halsted Street. Spend a night in a suite at the Peninsula (I once did a photo shoot in a suite there that I wished I could have stayed in for the rest of the night). The Annoyance Theatre sometimes has some oddly erotic shows going on, too, so check it out and see what works for you. Chicago is one of the sexiest cities around, but you have to live it to find it.

Q I am 78 years old, but can have a good hard erection. It takes me a long while to come; sometimes my partner wants to quit and we will try to get me another day. It leaves me confused.
A I love when 70-something men write me about their erections! It’s so encouraging. I certainly hope to one day have a senior partner with wonderful erections (though preferably not until I am a senior myself). It’s totally normal that it takes you, at 78, a long time to ejaculate and/or reach orgasm. As men age, their refractory period—the time from one ejaculation to the ability to have the next—tends to lengthen. Some men find it difficult to ejaculate more than once a day and others need to wait a few days for tension to build again. So long as it’s pleasurable for you and your partner, and you don’t let the confusion turn into frustration for either of you, then it can be fun to play without the expectation of orgasm. In fact, it’s a lesson that many younger people could serve to learn—not to let the expectation of orgasm get in the way of a fun naked romp in the sheets.

Q My wife and I have recently discovered the pleasures of anal play, for me. What is the best means for cleaning the anal cavity?
A Some people just poop first and that’s it—no special cleaning required. And of course they steer clear of “messy poop” meals on days they are likely to engage in anal play, because who wants to stick something in there only to get a lot of poop on their fingers or tongue or sex toy? (That doesn’t often happen, but let’s just say it’s not unheard of, either.) Other people clean things out with an enema, often going with a water enema rather than anything chemical (many homemade enema “recipes” that are on the Internet are not safe). As enemas are used for medical purposes, too, enema bulbs can be found in drugstores (and on Internet drugstores). You can also sometimes find enema kits in adult bookstores where you can also find butt plugs, vibrating butt plugs, anal beads and other fun anal-sex toys. Anal-sex books are also widely available. With toys, you’ll want to opt for toys with a wider base to reduce the risk that they’ll get “lost” out of reach in the rectum. A recent study we conducted at Indiana University about lubricant use found that water-based lubricant was more pleasurable for anal sex than silicone-based lubricant, so a gloppy water-based product may be a good option. I’m glad you two have stumbled upon something fun.

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

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