My boyfriend of one year is 27 and I am 45. He has revealed to me that he is a transvestite and has been “dressing,” as he calls it, for years. He has all the gear — wig, false breasts, waist-cincher, hip pads — and looks quite convincing in it. He assures me that he is not gay, and I understand the majority of transvestites are straight. I have allowed him to “dress” in my presence and I am not repelled by it, but I am also not a lesbian and I don’t want to be in bed with another woman. When he asks me to call him by a female name or stroke his “breasts” or “pussy,” I do not find this a turn-on.
But I am a good actress, and since I was not actually repelled, I indulged him and acted as if I were enjoying it. However, he now insists that I was turned on, and will not drop the...
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...I were enjoying it. However, he now insists that I was turned on, and will not drop the subject. He talks about little else but “dressing” now that he’s found the courage to “come out” to me, and wants to wear the clothes, falsies, etc., in bed all the time. This is boring me witless. I know he cannot stop cross-dressing — and why should he? — but he doesn’t seem capable of give and take, or of accepting that I do not want him dressed EVERY time we have sex.
I have decided to end this relationship, not because of the cross-dressing but because he is boring me. But I am afraid that, whatever I tell him, he will believe I’m ending it because of his cross-dressing. We do not live together, so it will not be that difficult to be rid of him, but I do not want to upset him after he has revealed an obviously deep secret. (When he first told me he was near to tears.) Any advice on what I can do to convince him to have “normal” sex (whatever that means), and keep cross-dressing to, say, one night a fortnight, or to finish [the relationship] without destroying him?
Woman Into Guys
Your 27-year-old boyfriend has probably been fantasizing about a woman like you, WIG, since the day he hit puberty and pulled on a pair of his mother’s pantyhose. It probably took him 15 years to scrape up the courage to come out to a girlfriend about his cross-dressing, and I’ll bet you he didn’t expect you to react as well as you did. When you not only didn’t freak out but elected to indulge him and appeared to enjoy his “breasts” and “pussy” (where your acting skills came in), you probably made him feel like he won the lottery.
And in a way he did win the lottery: Judging from the regular appearance of letters in Anne Landers’ fine advice column from freaked out housewives who’ve discovered their husbands cross-dress, women willing to tolerate men who cross-dress are few and far between. Women who’ll call their cross-dressing boyfriends by their “girl names” while having sex with them, stroking their breasts and pussies, are rarer still. Your boyfriend is lucky to have you — and he knows it. He also knows that if this relationship ends he’ll have to come out to his next girlfriend, a woman who might not be so indulgent or understanding. This gives you a certain amount of leverage, my fine non-lesbian friend, and if you want to keep this young man in your life, I’d suggest you start using it.
So, WIG, I’d advise you to tell your boyfriend one last time that his cross-dressing DOES NOT TURN YOU ON (speak in caps for added emphasis), but that like any good sex partner you’re willing to indulge since it clearly turns him on so much. BUT (caps again), if he can’t have sex with you as a guy nine out of ten times, then IT IS OVER. If you’re concerned about his feelings, explain that it’s not the cross-dressing that’s the problem but his selfishness. You’re willing to do the things he enjoys (having sex with him as a “her”), but only so long as he’s willing to do the things you enjoy (having sex with you as a “him”). If he can’t enjoy “normal” (whatever that means) sex with you nine out of ten times, then you’ll have to toss him — and his wig, false breasts, waist-cincher, and hip pads — out the door.
I’m a young man, in the prime of my life, living in the youth capital of the world, San Francisco. As a recent immigrant, I’m struggling with the housing crisis. There is a wonderful woman who loves me to death and lets me stay with her in her apartment, presumably until I find my own (we have yet to discuss it at any length). My dilemma is that I don’t feel the same for her as she does for me. I fear that by staying with her I am using/abusing her. I consider myself to be an honorable person and I wonder if I am doing the right thing. But otherwise, I would be homeless. What do you think?
This sounds more like a question for the Ethicist, a charming new advice column in The New York Times Magazine, but since you asked, I’ll give it a go: You are an asshole. Why haven’t you discussed your living arrangements “at any length” with this woman? Because you know that laying your cards on the table — you’re not interested in her, you just need a place to stay — will get your using/abusing ass tossed into the street. You’re allowing this woman to make assumptions — false assumptions — about your intentions for your own gain, and the longer you stay, the greater the hurt for her when you move on and she realizes you were using her. The choice you face isn’t between using this woman or being homeless, it’s between being honorable or dishonorable. The honorable man would answer a roommate ad; the dishonorable fuckwad would stay put.
I sometimes notice an unlikely consistency between the aliases of the people who write you. “Spike,” “Mike,” and “Tyke” all want to meet older women; “Mrs. Masturbator,” “Ms. Midlifer,” and “Miss Masturbation” were all featured in Pussypalooza. Do you always make up pseudonyms? I sometimes wonder how the yahoos who write you can be so consistently clever when signing off.
Wanking Instead of Working
What’s the deal with the questions from men into older women? They’re signed Mike, Tyke, and Spike. That seems like an odd coincidence. Are you writing your own mail, Dan?!
I’m a Big Asshole
One last time: Making up letters would only mean more work for me. I get plenty of mail, and as I’ve admitted in the past, I’m lazy. So, no, I don’t write my own mail. However, I am often forced to make up aliases for people who write me letters. Many arrive unsigned; others have sign-offs that make no sense or are too long. Take your letters, WIW and IBA. Wanking Instead of Working’s sign-off is his own, it works, so I left it alone. I’m a Big Asshole’s original sign-off, on the other hand, just didn’t capture IBA’s personality, so I came up with a new sign-off for him.
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