Ask Debby Herbenick | Sex on your period and an open gay relationship

Q I am a 35-year-old male who would like to think of himself as quasi-enlightened: well-educated, loving, open, blah blah. I also come off as fairly masculine: big frame, muscular, strong brow—so much so that people are even intimidated by me until they realize I am a puppy dog inside. My issue is that my girlfriend wants me to be more “manly.” She says she was initially attracted to me because I come off as confident and look masculine but now she is getting sick of my lack of confidence, assertiveness, etc. This is a problem for me as I am shy and insecure (aren’t we all?), but I also have Buddhist leanings where I try to tread lightly and realize things aren’t always as clear as they seem; hence no manly assertiveness of what I “know” to be right. Regardless, I want to “man up,” but I want to do it in a healthy, positive way. The majority of books I have found are either misogynistic and/or just about “how to get laid.”

A One thing I loved about the movie I Love You, Man was the different shades of masculinity depicted. There is no one way to be a confident, assertive man in 2009, which is great because it means you have options. Your path is not about how to “man up” like every other guy, but how to do so in a way that suits you. There are differences between assertiveness and aggressiveness, and you might ask your girlfriend if she can give an example of how she finds you to be less than assertive. For example, do you express your wishes or desires or do you just do whatever she wants all of the time? Let’s take dinner: If you’re in the mood for pizza, do you say “I’d like some pizza tonight” or do you kowtow to her wishes even if she wants sandwiches, which you hate? On the other hand: If she wants you to beat a guy up at a bar when he looks at her the wrong way, that’s aggression (and illegal)—and as hot as some rare women may find that, you probably don’t want to be that person. What about sex? Does she want it to be more physical and rambunctious? Rather than looking for a “how to be a man” book, let me suggest The New Male Sexuality (Bantam, $17), which presents a complex and interesting picture of being a man in a relationship with a woman. You might also check out autobiographies of men you admire for their confidence, as a way of learning about the way they talk about themselves, express their opinions or negotiate their relationships. Finally, consider spending more time with men you like, whether at a bar, on the basketball court, or getting tea after a meditation workshop. Pay attention to how they assert themselves. You might even ask men you admire who have similar leanings how they’ve developed their sense of manliness in a culture that so often supports misogynistic behavior. And if you find that you’re happy how you are, you may need to (assertively) point that out to your girlfriend. You can’t fix everything—her perspective included.

Q I’ve been dating a man who couldn’t jump into sex more quickly. We have crazy chemistry and at first I thought it was just that. The months are wearing on now, though, and I see he’s just not into foreplay. My vagina gets sore when we always jump in so quickly (though he’s quick to say how much he likes a “tight pussy” when it’s not wet yet). I know they say that you can’t change a person, but can a man who’s not into the pre-game show learn to like it at least a little?

A Oh, some men and their tight-vagina fantasies. Sure, it may feel good to have a tight fit, but unless a guy has a massive penis, the tightness is often due to a lack of natural vaginal lubrication. Low lubrication may mean that sex has been rushed or that a woman isn’t aroused. Why not try to slow the process down next time? Most people can adjust their sexual style and learn to enjoy a new pace. When he starts to drop his pants, encourage him to keep them on. Or set time limits: Maybe you can take charge and decide that you’re going to kiss—without even touching each other’s genitals—for at least 10 minutes. Changing one’s sex routine can be hot, whether it’s going from a quickie to drawn-out sex or vice versa. To set the stage for slow sex, consider trading massages, lighting candles, drinking wine together or bathing together first (make sure to have lube out for afterward, as warm water dries the vagina).

Q I’m a gay man in my early thirties. I did the “have sex with everything that’s not nailed down” thing (safely, thank you very much) and then wanted a relationship. I met another man who felt the same. Now we’re three years into a monogamous relationship. He regularly says how happy he is, how he doesn’t miss his old days of HIV testing, etc. Me? I want to have sex with other men. I haven’t done it, and I don’t want a lot of it, but I want the freedom to get a blow job from another man or jerk off in a bathroom stall with someone a couple times a year. I think I’m okay with him doing this too, but I know it’s not what he wants and I don’t want to lose him. What do I do?

A If you want to be with someone else with every cell of your being, then that’s a difficult force to stop. It doesn’t mean you can’t resist the urge—most people who are in monogamous relationships say they haven’t cheated on their partner, but it can sometimes be a struggle. That said, if you want to explore, consider talking to your boyfriend about it. If his happiness comes from having someone to love and count on and not be at risk for infection, are there types of sexual activities that he would give his blessing to as long as they don’t put you (and thus him) at risk? Could you and another guy watch each other masturbate in a bathroom stall but not touch each other? Could you get or give a blow job with a condom on (not no-risk, but quite low-risk). If you approach him from a place of love and reassurance—letting him know how much you value your partnership and that you wouldn’t betray his trust—you may be able to come to some type of agreement that works for you both.

Q Is it true that having sex on your period can help to end it? My boyfriend always asks to do it when I’m on my period so he can make it stop. I’d rather sit on the sofa and watch a movie than have sex when I’m bleeding. Is he right?

A Yes and no. Sometimes, sex toward the end of a woman’s period can help to draw more blood and tissue out, thanks to the contractions associated with sexual excitement and orgasm. But it’s not always the case. And if you have sex toward the beginning of your period, it’s going to need time—no matter how many orgasms you have. Bodies take their own sweet time. If you two do want to connect sexually, consider ways of being intimate together that feel comfortable for you or that interest you enough to leave the sofa and your movies.