Sunday, April 27, 2014

Woman's Boyfriend Wants Cross-Dressing Men

Dear Dr. Bill,

I've found your blog and would like to see if you can help me understand my now ex-boyfriend's sexuality. Ill try to keep long story short.. its mainly to understand where he's coming from and to have closure for me.

He is in his fifties, and I'm in my thirties. Things began well and I thought we were truly in love. Later on I started to find out he is a cheater, I've taken him back several times over the course of one year. I've found out things through his emails and texts with other women. The last time I took him back, he made me a promise that he'd be true to me because he wants to be with me. But I broke up with him yesterday because I've found out he was answering ads on Craigslist for sex, which I've caught him doing before. Except this time, he answered ads for "m4m" and "t4m".   In one email he asked a potential T/CD [crossdresser] if he has clothes because he'd like to try get dressed. I know not all CD are gay, but I think he is bi. Because in another email, he has met up with a T to get a "massage".  And I believe he wants to meet more CD who wants to have sex. 

I've always been supportive of LGBT community, him finding himself isn't my biggest issue, but it's his lies, and his multiple partners made me feel very unsafe about my sexual health. So I had to break up with him.  He of course denies all.

Can you help me to understand what he is going through? What can I say, or not say? I'm stuck between confusion and a broken heart. I love him, but he has done too much damage to me emotionally. I know this day will come, just didn't expect to be this way.  I feel hopeless, unattractive, and somewhat used.  How do I cope with this feeling, Dr. Bill?  Has any woman asked you for the same advice?  I've Googled quite a bite lately and found out a lot of women are going through the same thing.  It's always very insightful to listen to advice from the other perspective.
Thank you Dr. Bill. I hope to hear from you soon.

It sounds like I don't need to tell you that the main problem with this guy isn't whatever his sexual orientation may be but that he's sexually active with multiple partners behind your back, and isn't honest about it. It sounds like he probably lived a fairly "straight" life for most of his life and then hit middle age and decided he wanted to check out everything he'd been fantasizing about for so long while he still could. Is he gay, or at least bisexual? If he's looking for sex just with post-operative trans women that may be one thing, but if he's actively seeking sex with men [or, to put it crudely, "chicks with dicks"] that's another matter. He clearly seems to have some attraction for other men.

Open-minded you may be, but having a partner who needs to experiment with other sexual partners on a regular basis is a little too much for most people, so you were probably right in calling it quits with this guy. Especially when he lies to you about it on top of it. 


Yes, I have heard from a lot of women who feel as you do. You may well have been used, but there's no need to feel hopeless or unattractive because of it, or because of one wrong man entering and leaving your life. I would suggest coping with it by moving on, meeting new people, dating a variety of men until you meet someone honest and right for you. While it's primarily for people who have been married, the Straight Spouse Network proivides support for people who have been in "mixed" [gay/straight] relationships and feel confused and used.

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