Have you ever cross-dressed before?

I have done it secretly just for the thrill! Female clothes feel very comfortable to me!


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Most Helpful Girl

  • I really want to try it but I'm scared I'm going to get stereotypical and dress like the most obvious male swag

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Most Helpful Guy

  • in high school i went to Halloween as a cheerleader i played middle line backer so it was funny.

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What Girls Said 1

  • no i have not.

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What Guys Said 8

  • When I was about 4 or 5 my big sisters dressed me as a girl for Halloween. My Dad got pissed, but I didn't really care.

    But no, I've never had any desire to wear women's clothes. Most of them look so uncomfortable I don't understand why women wear them.

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  • Nope! Never have, never will. I'm already comfortable in my male clothes, so I don't have any incentive to wear female clothes.

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  • I can't say I have but I have no problem if anyone else wants to.

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  • I've worn women's jeans and a women's hoodie one time, not sure if that counts as I wanted to put on ones closest to looking like guys clothing.

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  • Yes, and I agree they can be very comfortable, but there's also the 'daring' aspect of wearing something society tells you that you shouldn't!

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  • Yes, I dress in dresses and skirts often

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  • just the underwear...

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  • As a kid, I had an older sister who wanted to play dress up, but there were no girls around to play with. So she dragged me into it (literally and figuratively). I didn't like it at all.

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    • You said you "had" and older sister? What happened to her? lol

    • I still have an older sister lol. I implied that she used to like to play dress-up, hence the past tense of 'have'

    • I know. I know. It just sounded like something happened to her. HAHAHA

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