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I Want To Go On A Date Dressed As A Women

Personal Stories, Advice, and Support 533 People

    I really want a cute boy to take me out on a

    date and i can wear a cute dress then after the date we can back to his place☺️
    Girlyboyrachel Girlyboyrachel 18-21, M 2 Responses Jul 14

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    An Erotic Date.

    I have often wanted to go out dressed as a woman on a date with a bi guy, we both know it was going to end up in bed.  I think about sucking **** and having mine sucked. 
    amysatinpants amysatinpants 56-60, M 3 Responses Nov 30, 2012

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    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 26-30 Jan 28, 2013

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    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 26-30 2 Responses Oct 6, 2012

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    I Do Date While Dressed

    I am usually asked out on dates a couple of times a month where I go out all dressed up and the last time was September 21st. All of my friends know I love going out all dressed up and if they are the one who takes me out they are the ones who are going to get to do what ever...
    ChristinaLynn ChristinaLynn 36-40, T 7 Responses Oct 2, 2012

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    It Could Go Either Way

    I DID ONCE AND IT WASN'T ALL THAT GREAT, LETS JUST SAY HE WAS A BIT SELF CONSCIOUS
    trans1 trans1 26-30, T Sep 1, 2012

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    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...
    glasscitycd90 glasscitycd90 22-25 10 Responses May 1, 2013

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    I Want To Date A Certain Boy Who Might Tell Stories.

    I think this guy named Steve is full of bull, he's always bragging about his dates being so aggressive towards him that he has to put his foot down to control the passion displayed, I imagine on our date how I'd turn him on,and make simple gestures, then advances, and finally...
    Chrysanthe Chrysanthe 18-21, M 2 Responses Feb 16, 2013

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    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 36-40 4 Responses Jan 1, 2013

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    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...
    STLCD STLCD 22-25, M Jul 29, 2012

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    How I'd Do It

    It would be senior prom with a dreamy guy I'd had a crush on forever. I'd spend the morning at the salon tanning and getting my hair nails and makeup done. I would have the dress picked out forever a pink halter top dress that flairs out slightly at the waist and comes down to my...
    MadisonElizabethTG MadisonElizabethTG 18-21, T 6 Responses Sep 9, 2012

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    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

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    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

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    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

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    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 61-65, T Aug 29, 2013

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    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

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    Can I Take You Out?

    This is one of the few fantasies that I have that I haven't acted on. I am a bisexual male and love both men and women. I have dated plenty of women but never dated a man. My fantasy date would involve a guy that wears very feminine clothing, fixes his hair, wears makeup, etc...
    rhouse rhouse 41-45 9 Responses Sep 12, 2012

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    The taste, smell, and feel. █I love it all :)
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    online that is. I'm a practicing heterosexual male who's not interested in men as a man. But online I like to be treated as a girl by men and women as well for that matter. I get...
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    I can never get excited by a naked girls body. Well maybe I can but that's rare. Foreplay is important to me, and if a girl wears stockings and heels for me, I'm a fired up. High...
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    so this is a story about the time my friend treated me like her sister so one day I was talking to my best friend and she asked me if i could be her sister for a day and i said...
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    Pretty much every attractive women I see...You could be a customer of mine in my office, or a random woman walking down the street..This is what i'm thinking...I wonder how you are...
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    I find it strange that some people on this site app whatever you want to call it get on here to try and find a girlfriend or boyfriend. I'm on here just to write and chat with...
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    Well I had a feeling that this was going to happen and my assumption was correct I had reciently came out of the closet and told my wife that i love wearing womens clothing...
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