Dear Dan,

I’m a 23 straight female, and I need some advice. The other night, after we both drank heavily, my boyfriend, 24, revealed he was wearing my underwear, he wanted to be pegged, and he wanted me to call him a bitch. We’ve been together for over 5 years (lived together for 4), and we’ve only had sex with each other, so this came as quite a surprise, especially since he’s never been terribly interested in sex. Before, we had sex maybe once or twice a month and only when he was horny (I don’t initiate because he always says no). This was initially worrisome to me a) because he has difficulty maintaining an erection during vaginal intercourse, and b) since I’ve been indulging some of his kinks (I’ve tied him up, put makeup on him, called him a bitch, fingered him etc.), we’ve been having sex a lot more often. He assured me that he isn’t gay though, so, in a fairly short amount of time (2 weeks), I’ve become more comfortable.

However, I feel I may be more vanilla than I initially thought. I like some of the light BDSM, but the crossdressing and anal play is more difficult for me. A friend of mine suggested reading your blog, which I have, and I’m trying to be GGG. I just don’t know what to do because I like my men more masculine. I don’t mind indulging him once in a while (he says he likes the “wrongness” of being “vulnerable” with me), but his requests are escalating, and I’m afraid he’s going to ask for something I really don’t want to do, and I don’t want to make him feel uncomfortable or think he can’t share his desires with me. When I’m drunk, I am much more game and can just be turned on by him being turned on, but when I’m sober, some of the stuff completely turns me off.

1. The sex has been better and more frequent (something I’ve always wanted). Should I just buck up and do it, my own arousal be damned?

2. How much should I be willing to do? (e.g., I’m not sure I can wear a strap-on with him, something he asked for the first night.)

3. I’ve told him some of my fantasies, which he didn’t seem too keen on (I want to have sex in semi-public, like a car; he said it wasn’t feasible). I also asked him to do some research on how to please me better since I’ve done a lot of research on this, and he is unwilling. He can’t give me a clitoral orgasm anymore, and I’ve never had a vaginal one. Am I within my rights to demand a little more from him?

4. Lastly, and I feel stupid asking this, but do you think there is a possibility my boyfriend (who I know loves me) might be gay or bi and not know it yet/be repressing it?

Too Confused for Clever Acronyms

My response after the jump...

Dear Too Confused for Clever Acronyms:

The sex has been better and more frequent because your boyfriend has finally been able to reveal his desires and fantasies to you. That’s a big deal, and when it happens, many people can go through a phase of being selfish and self-centered. It’s fantastic for him that you’ve been game to try them, and I want to applaud you for being so open and validating to him; whatever happens between the two of you, you’ve made a huge difference in his life by accepting his fantasies. But if you want more sex, getting more of a kind of sex you’re not necessarily into isn’t going to scratch your itch. You should never sideline your own desires or arousal—you’ll just end up unsatisfied and resentful. It seems like you are trying really hard to be GGG, but he’s not doing the same. If you’re willing to try out some of his fantasies, he should be willing to do some of what you like, which he’s not. He’s “unwilling” to figure out how to give you an orgasm? That seems unreasonable.

Sure, your boyfriend could be gay or bisexual, but my take is different: I think he’s a crossdresser who gets super turned on by gender play (and most crossdressers are heterosexual actually). His desires totally fit the bill. There is also a possibility that he may not just love gender play, but he may be genderqueer or transgender. Either way, his desire to wear women’s underwear and makeup and explore a feminine persona or his own femininity and your desire for masculine men may be difficult to resolve. This scenario reminds me a lot of two fabulous books by Helen Boyd you should definitely read, My Husband Betty: Love, Sex, and Life with a Crossdresser, and the follow up: She’s Not The Man I Married: My Life with a Transgender Husband. I’m concerned that when you’re sober, you’re turned off by the crossdressing and anal sex. You’ve clearly opened his Pandora’s Box, so there’s really no going back now. I assume that he wants more crossdressing and anal sex, not less. There is a lot going on in this situation and lots of questions for you to ask yourselves and each other. Can you meet his needs without sacrificing your own or doing things that turn you off? Can he step up to the plate and meet your desires? If the answers are yes, you’ve got a place to start. If the answers are no, it may be time to part ways.