I Going Out Crossdressed

Personal Stories, Advice, and Support 104 People

    I was showing my girlfriend a new ensemble

    that I picked up yesterday, and she said: "With that outfit, I will go shopping with you fully dressed anytime!" I cried! I absolutely cried. I've been dying to go out shopping with her fully dressed en femme for over a year. I've tried and tried to get my style right...
    deleted deleted
    26-30
    4 Responses Oct 20, 2015

    I'm going out tonight

    as Lisa with some girlfriends. I'm so excited, going to be a great night :) I will be wearing a nice royal blue dress with nude tights and nude heels. Love the combination of blue and nude. Getting dressed to go out as a woman is so much more fun than putting a shirt and jeans...
    deleted deleted
    26-30
    3 Responses May 9, 2015

    Since EP is about to end,

    I just have to share today's incredible experience. As many of you know, I have a girlfriend who had been incredibly supportive of my dressing. She is my bff, my stylist, and my biggest fan. She had been promising me a shopping trip for over a year, and today it finally...
    deleted deleted
    26-30
    4 Responses Mar 28, 2016

    I try not to call it crossdressing.

    At least not until all those girls in jeans and tee shirts start calling themselves crossdressers. But yes. Yesterday was a wonderful girlfriend Christmas shopping day and dinner after. This time of year, the weather is frightful but the shopping delightful. And we are in a...
    JoanieNewHampshire JoanieNewHampshire
    61-65, T
    7 Responses Dec 22, 2014

    I'm a boy and whenever someone I don't know

    uses female pronouns on me in public, I get an exhilarated rush. Dressing in "men's" clothes always made me feel like nothing, but when I go out dressed in women's clothes, I feel powerful. And when someone thinks I am a girl I feel even more empowered.
    ToshiLSB ToshiLSB
    22-25
    1 Response Feb 24, 2015

    I spent the whole day crossdressed in public

    today. Well not the whole day since I didn't leave the house till 1:30. I started out by going and playing bingo, which I do every Sunday. I was wearing a white bra, with breast forms, under a thin flannel looking shirt, with top two buttons undone, and over that I had a crochet...
    Michelle1976 Michelle1976
    36-40, T
    2 Responses Dec 22, 2014
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