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  • #8377
    Debra Wright
    Participant
    Registered On: August 25, 2015
    Topics: 1
    Replies: 19
    Has thanked: 1 time
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    Black long line bustier a black slip and black short (mid thigh) skirt black nylons black lace panties 1.5 in black heels I had a auburn shoulder length wig was dress as hooker for halloween

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    • #15814
      cdheaven
      Registered On: September 18, 2015
      Topics: 1411
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      Oh goodness, it was soooo long ago!…and oh so simple.  I wore girls jeans, a powder blue plaid top, simple black pumps, my big hair, big sun glasses, and a big smile.  I was nervous at first, but I settled down by the time I got to the movie store I was going to, and I calmly walked and returned the movie.  The clerk said “thank you ma’am”, I said you’re welcome in my best girl voice, and walked out as he was telling me to have a nice day.

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    • #9425
      oh to be rachel
      Lady
      Registered On: October 6, 2015
      Topics: 3
      Replies: 13
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      A wedding dress. Thank god for halloween.

    • #9327
      Anonymous
      Topics: 0
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      Kept it simple: bootcut jeans, turquoise flats, pink blouse and black cardigan with my long blonde wig.

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    • #9091
      Vanessa Law
      Managing Ambassador
      Registered On: April 19, 2012
      Topics: 78
      Replies: 158
      Has thanked: 42 times
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      My first time out… wow it was so long ago. I think I wore blue jeans, high heel boots, and a feminine turquoise top.

      1 user thanked author for this post.
    • #9007
      skippy1965 Cynthia
      Ambassador
      Registered On: August 25, 2015
      Topics: 114
      Replies: 1291
      Has thanked: 571 times
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      Ok-wow! I wish I Could see pics of each of you beauties! I m so jealous! I’ll be posting soon about my first time but it was not near as exciting as several of you. You rock girls!

    • #8657
      cdheaven
      Registered On: September 18, 2015
      Topics: 1411
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      It was not really a good look. Do you really want to know what I wore, well OK here goes…
      I had a floral dress with a pale cream as the background colour, mustard coloured opaque tights and pale cream high heels, too high for easy walking. I had a scarf that had dark red and other colours. I borrowed a beige coloured coat. My wig was dark brown and fairly short. I did not have many clothes at the time so really there was not much choice for what to wear!

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    • #8374
      Jenifur Charne
      Duchess
      Registered On: August 22, 2015
      Topics: 23
      Replies: 74
      Has thanked: 16 times
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      On the evening of the local crossdressers get together that turned into my first time out, I was wearing an early 1990s nightclubbing LBD, black low chunky heel courts, and my mid length wig. I can’t recall what lingerie or jewellery I was wearing that night. 🙁

      As for the day I came out full time as TS, white blouse, short black skirt, white padded Wonderbra, beige pantyhose, black low chunky heel courts, a cheap gold plated necklace and clip-on earrings, and my wig.
      At the time, my hair wasn’t, yet, quite long enough to be passable, so I needed to keep wearing the wig. By the end of that summer, the wig had been retired. The Wonderbra was all the rage at the time, so to help with my bustline and cleavage I followed the herd and got a few. I hadn’t, yet, got my ears pierced so I was still using clip-on earrings.

      1 user thanked author for this post.
    • #8275
      Kendra
      Duchess
      Registered On: September 10, 2015
      Topics: 20
      Replies: 62
      Has thanked: 19 times
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      It was 1980, a gay friend talked me into getting dressed en femme with him and going to a female impersonator show (actually I lost a bet that I secretly wanted to lose) It was his closet and his makeup skills. I still remember what I wore because it was such an intense experience for me – a shoulder length chestnut brown wig, a black and red print top, a black padded bra, a fairly short black flared skirt, red pantyhose, and a black pair of t-strap shoes with heels that were 3 or 4 inches. He had two other friends into this as well and they shared closets and were able to come up with stuff that fit me and made a decent outfit. The room itself was filled with crossdressed gay men, my friend was a wizard with makeup, I was young and fit and I had good skin and long eyelashes. So while I was totally freaked out at what i was doing, and while my heart was pounding intensely – I probably blended in pretty well. Sadly not a single photo – I had a couple but got rid them in a purge.

      But that is very different than going out for a stroll on the street or joining a group on non-crossed people at an outing. My experience, terrifying as it was for me, took a lot less courage I think than the other examples on this posting

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    • #7114
      Holly G
      Lady
      Registered On: August 25, 2015
      Topics: 12
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      I feel like I’ve had 2 first times out. The first time I saw no one aside from the worker at the drive through I went to. That time I wore (much like Millicent ) my tight little black dress, fishnet stockings with a garter belt, red 4″ heels, and my red head page boy wig. Probably way too much makeup, plus clip on earrings, bracelets and a necklace.   I love being outside in a skirt/dress!

      The second time was WAY more public and terrifying, so I tried to blend more…tried…???? I wore tight jeans with 4″ heels (I know I know but I LOVE walking in heels!) a tucked in t-shirt, the same wig, clip on earrings, and a few bangle bracelets. I also had sparkle purple toenails which I loved. MUCH less makeup this time but a HUGE smile! ????????????????????

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    • #7113
      Holly G
      Lady
      Registered On: August 25, 2015
      Topics: 12
      Replies: 123
      Has thanked: 65 times
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      Sounds like an incredible evening out with a wonderful wife and very accepting friends! What a birthday gift!????????

    • #6782
      Millicent Teasedale
      Duchess
      Registered On: August 24, 2015
      Topics: 13
      Replies: 203
      Has thanked: 47 times
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      My very first time, as I mentioned in another thread, a little black dress way too short and way too young for me, stayup fishnets, heels, a 3/4 wig with a headband and my bangs brushed forward, bra stuffed with homemade forms made of rice, a girdle of some sort, and makeup that probably didn’t look as good as I thought I did. Since then I’ve toned it down – black palazzo pants and a pink blouse with strappy heels, a red skirt, white blouse and black cardigan with suntan hose and black flats (think Amy  Farrah Fowler), a far more appropriate LBD.

      1 user thanked author for this post.
    • #6775
      cdheaven
      Registered On: September 18, 2015
      Topics: 1411
      Replies: 3942
      Has thanked: 0 times
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      I have been dressing since i was 5 or 6, my first time really out was with a very nice couple was a little back dress with heels and pretty ugly wig. I did pass Ok that was a dozen years ago. I now am out at least once a week and pass very well. Still working on my voice

      how about you

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