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Does Wearing Women’s Clothing Make Me Gay?

521 days ago
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Am I crazy? My girlfriend let me dress up a couple of months ago. Now I’m finding I like women’s clothes a lot and seem to be attracted to men. I just love the feeling of the whole deal. My girlfriend told her friend, who told everybody else. We split up, and I lost some friends, but I find that I’m happier when dressed as a woman and in the company of a man. Am I becoming gay?

First of all, I do not think you’re “crazy.” Enjoying women’s clothing and being attracted to men are both well within the range of normal human sexual and gender expression, which can change throughout our lives. I’m sorry that your girlfriend and some of your friends weren’t supportive of your newfound desires. That kind of rejection can really hurt, but it doesn’t mean that there’s anything wrong with you.

The act of enjoying wearing women’s clothing does not necessarily mean you are gay (I wrote a column recently answering a somewhat similar question from another reader).  Finding happiness in dressing as a woman and being attracted to men are two separate things. One has to do with your own gender expression, and the other has to do with who you are attracted to. You could enjoy expressing a feminine side of yourself and be attracted to women, men, folks with non-binary gender identities or all of the above. You might be gay, or you might not—sexuality is not neatly divided into little boxes, and our identities can be quite complex and unique.

I encourage you to explore all of the new feelings you’re having, separately and together. You mention being “happier when dressed as a woman and in the company of a man.” Chase that happiness. What do you enjoy about women’s clothing? Do you like wearing it alone, with others or both? Only in sexual situations, or during other activities? What about it makes you happy? Same thing for your attraction to men—are you attracted to men only when wearing women’s clothing, or at other times? What is it about men or masculinity that you find attractive? There are no right answers to these questions, except what makes you happy. I hope that you have other people and partners in your life who are supportive of your exploration, because you (and all of us) deserve happiness.

Laura Anne Stuart owns the Tool Shed, an erotic boutique on Milwaukee’s East Side. She has a master’s degree in public health and has worked as a sexuality educator for more than fifteen years. Want Laura to answer your questions in SEXPress? Send them to laura@shepex.com. Not all questions received will be answered in the column, and Laura cannot provide personal answers to questions that do not appear here. Questions sent to this address may be reproduced in this column, both in print and online, and may be edited for clarity and content.


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