Girls, Is cross-dressing this acceptable?

I was talking to a female friend of mine recently, and she made the comment that she likes to go to the vintage clothing store and "dress up like a boy" just because she finds it to be fun. She doesn't buy the clothes, just in the fitting room.

Anyway, during the conversation, I said "I can only imagine how different this conversation would be if I were the one talking about cross-dressing." To which she replied, "So much funnier."

Then a few days later, it came up again somehow, and I was sort of stating why I wouldn't ever try it (it's just not my thing, no problem with people that enjoy it) and mentioned that I have no fashion sense. She said "Fashion sense doesn't matter, just throw on a dress."

So girls, is she just being silly, trying to egg me into trying it so she can laugh at me. Is there something that you all actually find cool about it? In other words, what's going on here?


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Most Helpful Girl

  • It's fine for a costume party or something where you're clearly ripping the piss.

    My brothers used to run into my room and grab bras and skirts, put them on and run around the house screaming in a high pitched voice "I'm a girl, look at my boobies". That was funny and clearly not because they wanted to pretend they were girls for real. Also ruined all my clothes.

    But serious cross-dressing you should keep to yourself. You'd be hard pushed to find a partner that would accept that. I wouldn't.

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What Girls Said 4

  • well,maybe she's into that sort of thing,but people also just do it for fun sometimes. plenty of men enjoy wearing dresses,it's worth a try,just so you know what it's like

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    • I don't doubt it, but personally I've just never had any urge or curiosity about it. Completely neutral. I am of Scottish heritage and have worn kilts before, and speedos and stuff. I've got no problem wearing "different" clothes, just never wanted to try out women's.

  • I have worn my boyfriends boxers around the house and to bed, and I have worn his button down shirts, and being silly he has tried on my panties,

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  • Well it what she finds fun. I don't think any should be able to say if it is 'acceptable' since she ain't breaking any laws and it's for fun. Even if it wasn't for fun why would there be a problem.

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  • I dressed like a man for Halloween once.

    But it's hard for me because of a big chest.

    I didn't enjoy it for being a man though. I'm pretty happy dressing as a woman and prefer when people know I'm a woman, haha!

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    • Why you did not enjoy being a man?

    • Show All
    • I think that a guy being a woman for will have a more uncomfortable time.

    • It wasn't uncomfortable, I just like being and looking like a woman since I feel like a woman.

What Guys Said 1

  • So many years ago on a dare my girlfriend dared us to go to a Halloween Party in role reversal. She dressed up in my suit and tie but wore full make-up put her hair up and wore heels, she made me wear a slinky dress coctail dress, flats with a wig and make up. We went as each other. We won the contest for daring costume and recieved 100.00 bucks and a bottle of rum. later that night she confessed that she thought it was hot and confessed she had a thing for tranny's., something she found sexy. She had bought lingerie for me but didn't think i would go for it. I did and we spent the weekend in role reversal dressing. She loved it. so did i and i still do but i don't share it. I learned over the years the hard way that most women are insecure with men that like to cross dress. I had one girlfriend years later that was bi and she had asked me on more than one occasion if i was. I told her i was not which is true. This turned out to be more about her dealing with her bisexuality and accepting it than me. I confessed that i have cross dressed at times previously and even she had an issue with it. Did not like it and wished i had never told her. Only 2 out of many women i met over the past 20 years have ever been even remotely ok with the idea of it. Most of the time it is a dare to wear her panties or she wear my boxers and you would be surprised how many times that comes up with the many women i have known over the years. However its always comes down to the same thing. end result. Any admission of enjoyment of cross dressing has forever changed their opinion of me as their partner.. After admitting it i have had women leave me shortly after. cheat on me in the near future and tell me I'm just not the right guy for them or even tell me i'm masking being a homosexual. I am straight. I enjoy cross dressing in private and now married to a women that adores me and she does not know and i have learned my lesson. If i love them don't tell and be prepared to hide it forever.

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