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Thread: My first time going out while crossdressed

  1. #1
    Junior Member
    Join Date
    Oct 2009

    Talking My first time going out while crossdressed

    Well this Halloween was certainly one to remember, for the first time ever I had the opportunity and the guts to wear woman's clothing in public. I know I know, it's Halloween and everybody is allowed to do something crazy - but it was my chance.

    So before last week I had never:
    *worn a skirt or dress for more than a few moments
    *worn high heeled shoes for more than a few moments
    *been dressed completely as a woman
    *worn anything unusual in front of anybody - ever

    I told some of my friends who were going costume shopping that I needed their help with my costume - I went as former Alaskan Governor and 2012 presidential hopeful: Sarah Palin

    So we went to the mall and got costumes for everybody, and myself and others got clothes from the secondhand store (Goodwill). My friend Adam and his girlfriend helped me get clothes and I think his girlfriend was absolutely delighted to participate in this - she helped me buy a woman's business suit (skirt and blazer), some medium heeled shoes.

    Of course I had to act like I didn't know anything about these things.

    Before we left his girlfriend quickly snapped "wait a minute, do you want to wear pantyhose?"
    Now if you've read any of my other posts, I'm not as much even a crossdresser as I am a pantyhose fetishist.
    I had intended to wear pantyhose with this outfit from the beginning, but I can't believe SHE asked ME if I wanted them.

    So we stopped at Target and by her recommendation we bought 2 pairs of Leggs Sheer Energy Full Support pantyhose. I know a lot about pantyhose, so I had to use my best bluffing skills to feign ignorance about such terms as control panty and reinforced toe.
    His girlfriend said I should wear both pairs at the same time to hide my leg hair

    So we ate dinner and everybody went home to prepare for Halloween the next day.

    The next day I went to my friend's room where everybody was getting ready for the party (or parties) that evening and put on my costume.
    I hope nobody saw me expertly put pantyhose on in under 30 seconds.
    And it all felt so wonderful, the shoes were not uncomfortable at all, the skirt was a taut business skirt, and the pantyhose were so very tight and controlling - and the second pair more than tripled how tight they were.

    After I was finished everybody had a good laugh.

    Shortly after I was dressed I got a call from a girl I know (she's not my girlfriend but we do like each other very much) and she said she wanted to surprise me with her costume. I told her "wellllll I think mine might be a bigger surprise"
    I was terrified knowing that a girl who likes me is about to see me dressed like this.

    She came upstairs (she was dressed a a LOLcat, very funny too) and her jaw dropped, I didn't know if she was disgusted or in awe.

    Without saying anything she reached down and rubbed my leg to see how my pantyhose felt!

    She asked me all kinds of questions and I answered truthfully really. "so how do you feel" "actually very good, maybe *too* good"
    In fact I told lots of girls that night what I want to say all the time but have no reason to.
    "I don't know what women are complaining about, I'm a guy and I don't mind wearing them at all. You girls should wear these because you look much better than I do in them."

    We went to several parties that night and actually I didn't receive the dirty looks as I thought I would. My (kind of) girlfriend stayed with me all night and I caught her several times eyeing my legs - I still don't know what she was really thinking.

    And we all got really drunk, and did all the things we normally would have done no matter how we were dressed.
    I "accidentally" (on purpose) fell asleep in my costume in the dorm room were several of us passed out that night

    I was sad to take my costume off as I probably won't have this chance until next Halloween. But it all went so extremely well.
    So no I do not and do not intend to openly cross dress, but Halloween is always the exception to all rules.
    And yes I'm sorry no pictures exist - I refused to be photographed.

  2. #2
    Join Date
    Nov 2009
    sound awsome. i was away over halloween so couldnt dress up but, im glad u had a great time. were u wearing panties/bra

  3. #3
    Junior Member
    Join Date
    Oct 2009
    Quote Originally Posted by StephHamilton View Post
    were u wearing panties/bra
    No, I didn't wear anything that wasn't mentioned. No fake breasts or anything, I wore my regular briefs under the pantyhose .
    Well, under the blazer I wore a blue t-shirt that was mine.

    Ha, I just realized that I wrote a sort of long story.
    Well it was a big night.

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