How do i bring up the subject of crossdressing in dating?

17 Comments

The only sexual fantasies that have ever really appealed to me are crossdressing and pegging. I don't really get off on the idea of anything else but I still feel normal emotional ties and needs so I want to find someone who's ok with that but I don't know how to bring it up and I don't want to be abandoned because of them. And what should do I do if I like someone and they're not into it?

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  • Iambillythemenacetosociety
    1 year ago | pl

    Yet another crossdressing post that has been posted a thousand times. Can't wait for the next one.

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  • sweetone89
    1 year ago | pl

    Remember, the right person will never abandon you. Maybe you feel awkward saying it out loud? Maybe you and your sexual partner could write out your fantasies for the other to read?

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    • Anonymous Post Author
      1 year ago | pl

      i'm just not sure about how to bring it up at all or when the best time is to

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      • sweetone89
        1 year ago | pl

        Do it when you feel comfortable. How close are you to your partner?

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        • Anonymous Post Author
          1 year ago | pl

          i don't have anyone yet i'm just worried about it

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  • Anonymous Post Author
    1 year ago | pl

    maybe I can make it less weird by choosing a character. i feel like I'd be cute as alice in wonderland.

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  • Lusty-Argonian
    1 year ago | pl

    I'd suggest just being straight about it a few dates in after they've gotten around to knowing you. Some are into it but most will not be. If you like guys at all that'd be an easier path for dating but dating women will just harder because of it

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  • Curiouskitten444
    1 year ago | pl

    I would wait until date 3 to disclose that. The way I would go about it would be to play a game of "what's your freakiest kink?"

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  • donteatstuffoffthesidewalk
    1 year ago | pl

    when she asks if you have any hobbies tell her youre in a j edgar hoover reenactment club

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  • bigbudchonger
    1 year ago | pl

    You don't man, because your chance of attracting a mate with such perverse measures are close to 0

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    • Anonymous Post Author
      1 year ago | pl

      My main worry is that the only women into it are promiscuous and non-committal. There are obviously women into this but most I've heard of are not really the relationship types.

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    • Lusty-Argonian
      1 year ago | pl

      Perverse measures? Please elaborate im curious what you mean exactly

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      • bigbudchonger
        1 year ago | pl

        The guy likes getting fucked up the arse with a strap-on whilst wearing women's clothing.

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        • Anonymous Post Author
          1 year ago | pl

          i also like long walks on the beaches gazing at the stars and cuddling. i'm hoping it at least cancels out to at least neutral.

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        • Lusty-Argonian
          1 year ago | pl

          This conversation was alot more fun in my head

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