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I Want To Go On A Date Dressed As A Women

Personal Stories, Advice, and Support 534 People

    My ultimate goal is to go out on a date with a

    feminine transgendered woman. I'm a very straight looking and acting, blue collar guy. I am big enough and strong enough to make you feel secure and passable on my arm. Although I am just a regular guy, I am uniquely supportive and encouraging of my transgendered partner...
    Hot4Tgurlz Hot4Tgurlz
    41-45, M
    6 Responses Dec 29, 2015

    I would love to do this,

    it has always been a fantasy of mine. I want to be treated as the women I am trying to be. Wined and dined and made love to.
    Michelle1976 Michelle1976
    36-40, T
    4 Responses Mar 23, 2014

    Out With Wife Dressed

    My wife loves that I crossdress and we often go out in public dressed, to movies, bars, parks and even to dinner. We try and stick to the places that are usually not lighted the best, like bars, movie theaters, and walking around a park at night. Sticking to these places lets me...
    pantiescouple pantiescouple
    Jan 28, 2013

    I Have Already Been Doing This For Many Years.

    I go on dates with men and we are just like a man and woman out on a date. Even though I have passed in public as a woman many times my date usually takes me out to a gay TG friendly nightclub or bar. Sometimes we even go to a straight nightclub or bar and also may go to a movie...
    JulieLisa JulieLisa
    66-70, T
    3 Responses Aug 29, 2013

    This Would Really Be Great!

    OK, it isn't easy for me to even convince myself that it is OK to just go out in public dressed as a woman. I haven't really done it yet. But I've always thought that it would be a lot easier in the company of another CD. But it would be so much easier and more fun to have a man...
    RayanneA RayanneA
    56-60, M
    Sep 30, 2013

    Not A Real Date But Close Enough

    Recently I had made plans to go out to a very late night lunch/dinner whatever you want to call it with a very good friend of mine from school. What makes this worth telling is that she knows that im a crossdresser and that she wanted me to dress up when we went out. What makes...
    deleted deleted
    6 Responses May 1, 2013

    It Could Go Either Way

    trans1 trans1
    26-30, T
    Sep 1, 2012

    I think this would be

    so much fun :) I got to go out as a girl on a date!!:)
    Shelly6395 Shelly6395
    2 Responses Aug 7, 2015

    Remember that episode of family guy

    where Stevie pranks Brian as a woman and gets him to touch his penis? That was the best moment of the whole episode for me!
    Studdleywizbi Studdleywizbi
    18-21, M
    Nov 7, 2014

    Sort Of Have Already, Sort Of Haven't Too...

    well technically my friend and I are not dating, yet... but we've gone on two, I guess "pre-dates" you could call them and I've been partially dressed but eventually as I work on completing my work and as I make progress with my friend and we perhaps start actual dating soon...
    22-25, M
    Jul 29, 2012

    The Wish To Show Them

    I have been going out dressed as a women a couple of times now and it was great fun. It only was a visit to good friends who knows about me and it was dark allready, so we drove up to their place and got out of the car and in to the house. Not much up to it I guess, but, for it...
    laikagirl laikagirl
    51-55, M
    Aug 23, 2012

    My First Date As A Woman

    I have been fantasizing for a long time about going on a date as a woman. I have been going out dressed for many years. But dating was just a fantasy. I met a guy online and chatted for a few months. He asked me to go on a date. I was apprehensive at first because we are never...
    ka851 ka851
    51-55, T
    1 Response Dec 16, 2012

    Treat Me Good

    i would love to go on a date dressed as a women. i would wear soft sexy lingerie with stockings, 5 inch heels and a sexy dress but not too short. my face would be made up along with my toe and fingernails being painted and put on a nice wig. i would then go out to meet my date...
    badanbald badanbald
    4 Responses Jan 1, 2013

    I've Been Doing That For Years

    When I came back out quite a few years ago after a hiatus it took me awhile to get used to being out in public... but I kept doing it, going out daytimes most often because that's when I had the opportunity. And I was also online a lot and lots of guys kept wanting to get...
    deleted deleted
    2 Responses Oct 6, 2012
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