Ask Debby Herbenick | Anal sex and a cross-dressing husband
TOC's sexpert tackles your most penetrating questions.
Q I’d like to comment on the guy who wrote to you about his problems staying hard the first few times he had sex (In & Out, TOC 243). I’ve worked through the same issue all my life (I am a 34-year-old hetero male): too nervous the first time to stay erect, even with partners I knew well. So, I gave my partners lots of great oral the first time we slept together, and then by the second or third time, I didn’t feel nervous anymore and was hard as a rock. Good strategy? Or just a fluke that’s worked for me?
A Focusing on one’s partner—really, anything that feels good and distracts you from worrying about your sexual performance (hey there, erection!)—is a viable strategy. It’s great that you’ve found a way to get and keep the rock-hard erection of your hetero dreams. Love it. Ian Kerner, in his book She Comes First (William Morris, $23), wrote about how his anxiety about pleasing a partner led him to become quite the cunnilinguist himself. Is it a strategy that will work for all men? Of course not—nothing works for everyone. But will it work for many men who are hoping to chill out during sex, get and stay hard and have connecting, orgasmic sex? Yes, yes and more yes.
Q My boyfriend and I have been talking about trying anal sex. But I’m not sure what’s in it for me, being a girl and not having a prostate to stimulate like guys do. Also, I’m afraid of getting poop on his dick, which would mortify me.
A What’s in it for you? Maybe nothing. Maybe discomfort or pain. Or maybe some amazing pleasure or even an orgasm (with practice) if you proceed wisely. Should you decide you’d like to try anal sex, go slowly at first, use gobs of lubricant and please, please, please communicate with your partner about how it feels and whether you want to pause, stop altogether, keep going, change the pace or switch body positions. First, to get to know your anal area (seriously!), maybe try finger-play in your butt before proceeding to your boyfriend’s penis. Check out my book, Because It Feels Good: A Woman’s Guide to Sexual Pleasure and Satisfaction (Rodale, $22), for easy-to-follow tips on getting comfortable with your butt and learning to explore anal play in comfortable, fun ways. Oh, and the poop thing? Empty yourself beforehand and maybe avoid anal play on days you’re a little “runny.” Even so, occasional poop remnants are par for the course and nothing one needs to feel mortified about at all—if your boyfriend can’t deal with the possibility of a little number two, he doesn’t belong in your butt anyway.
Q I’ve been married for two years to a man who likes to wear women’s underwear. He first told me (when we moved in together, right before the wedding), that he liked to wear lingerie sometimes because it turns him on. I said I would try to get used to the idea. The wedding was paid for and I felt like I couldn’t back out (but wanted to). We got married, and the lingerie didn’t seem to be much of an issue because it was only sometimes. I ignored it. Then I got pregnant, and his cross-dressing escalated. We had many conversations about my feelings of disapproval and his feeling that it wasn’t fair of me. He started wearing women’s tank tops at home, saying they were more comfortable than men’s tanks. I’ve been trying to turn a blind eye to his behavior, but it makes my stomach turn. The tension between us continued to build. Now he wears women’s panties daily. We’ve tried therapy and were told that cross-dressing is progressive and the therapist suggested defining boundaries. I would be very uncomfortable if my son (or anyone else) found out. He refuses to set any boundaries and doesn’t think that letting our son see him dressed that way is a problem. I know that divorce is imminent, but what can I do to make sure our son isn’t injured emotionally because of this?
A They say money is the root of all evil—and sometimes it even sways people to marry someone they have doubts about for fear of losing their various deposits. Your therapist is right that cross-dressing often progresses. The thing is: There’s nothing “wrong” about men cross-dressing. But there’s also nothing wrong with wanting to be married to a man who doesn’t wear women’s panties. Not only do you and your husband have competing needs, but you have a son to raise—a son who would benefit from parents who work together with a child psychologist (see apa.org to find one) to (eventually) explain his father’s cross-dressing. As surprising as it may seem, children typically have less of an issue with cross-dressing than one might guess; rather, your son’s struggles with divorce are likely to be the common ones: He needs to feel loved by both parents, not be put in the middle of fights and have a sense of home. You might also find crossdresserswives.com to be a helpful website for support and information.
Q My wife and I have been married less than two years, but our sex life has slowed to a stop. She seems to have no interest in me physically: I’ll try to kiss her and she turns so I can’t kiss her lips. I’ll hug her and her arms stay motionless at her sides. I’ll try to hold her hand and she’ll pull it away from mine—all signs I would have taken as “not interested” as a seventh-grader, but this is my wife! I’ve tried writing her letters to let her know how I feel and how beautiful I find her, buying lingerie and sex toys, performing conspicuous chores around the house—anything I think might make her “like me.” It’s breaking my heart. When I ask her what’s going on, she rejects the idea, acts hurt, and says I never make advances, which is not the case!
A Sounds like sex therapy is in order! In all seriousness, you have tried everything one would expect: letter writing, kissing, hand holding, hugs, lying low and doing nice things. You could try talking to her once again. Say in your own words that you love and desire her but are confused by her sense that you don’t make any advances. Gently let her know what you’ve considered to be your advances (hugs, kisses, whatever else you do) and ask her if (a) she wants to be sexual with you and (b) what types of intimacy would she enjoy (kissing, bathing together, intercourse, oral) and (c) how she would like you to initiate. You might also ask if she’d consider initiating. Please don’t wait for it to get worse; it is a totally normal human need to want to be touched, held and loved. Find a trained sex therapist through aasect.org or sstarnet.org.