Crossdressing - a guy as a girl?

As a relatively new person to the concept/idea of it, who here (if anyone) has let people they know that they like to crossdress?
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Most Helpful Guys

  • I don't cross dress but if I did I wouldn't tell anyone about it. I'd lead like a secret double life and have a completely different set of cross dressing friends. It would be some real psychotic shit. I imagine I'd be getting fucked by strange guys - it would be awful.

  • Do you need others to know starting off so that you feel comfortable?

Most Helpful Girls

  • I have A friend that like cross dressing , to try what’s like being a woman. Got addicted to it. Even jerk off with dildo but he said he is not gay. He has a wife.

    • I wouldn't go that far to have "fun" with a dildo, but if I'm honest, what I dress as does turn me on as well (for the most part) The experience itself, maybe the fear of being caught, is what makes it fun?

    • Oh, and to add to that as well, I'd consider myself completely straight as well, just with this twist :/ I'm wholeheartedly all for girls, especially ones that can dress the way I try to, but it's extremely rare I ever see anybody that is dresses the way I like to.

    • My friend said he wants to know how do girls feel. And touching woman’s things turned him on. things like bra, heels , dress. He’s completely straight. Don’t want to hook up with any guys. I guess the best thing he wants to do is hook up with another woman while he s in woman ‘s outfit. Like switch. The woman be the one on top.

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  • I would just rather dress to be comfortable... Do whatever makes you happy...

    • YAY 🙋 Thanks for most helpful girl 🎀

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What Girls & Guys Said

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  • Only worn friends panties while we fooled around.

  • I don't like seeing people dress as the opposite sex,

  • I mainly like wearing underwear, though sometimes I try on a little more. No, I have not told anyone before.

  • Have cross dressed in the past and been dressed up by female friends for a laugh.

    • Was it obvious that you were dressed up? Like as a prank or something like that? Or to the point of you wouldn't know from a distance or if you asked?

    • Back then depended on who you asked but most guys can't pull of cross dressing convincingly. First time I did it wasn't convincing at all but when friends dressed me and make up maybe might have fooled someone but doubt it

    • Ahhh ok, my first two "public" experiences were not that convincing at all, but I guess I have the body to pull it off from a distance - the facial hair was pretty much the dead giveaway. Now, not so much.

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