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Thread: Whats maybe the Craziest/Funnest Outfit you ever put on ?

  1. #1
    Aspiring Member Robbiegirl's Avatar
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    Whats maybe the Craziest/Funnest Outfit you ever put on ?

    So many of us have these bucket lists and I have often wondered if the experience was half as fun as the Fantasy

    Did you ever wear a square dance dress, or Playboy bunny outfit, or even harem girl ?

    My only really fun one was wearing my sisters new Tennis dress and ruffle but panties. Watching in the mirror how the skirt would swish and fly up while i swung the tennis racket was silly but fun. And of course everytime I barely moved you could see the ruffle butt Panties !

    tennis.jpg

  2. #2
    Senior Member
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    Robbie you look GORGIOUS in the included picture.

    Where were you playing? Wimbledon?

    For the record I'd love to dress up as either a square dancer or playboy bunny.

  3. #3
    Sallee Sallee's Avatar
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    I ride bike alot I have only dressed once to ride with riding tights shorts and shirt. No pics sorry. I did for a short ride and felt really self conscious. I certainly could not make that look work as well as all those women who dress in bicycle drag
    [SIGPIC][/SIGPIC]Sallee

  4. #4
    Female Illusionist! docrobbysherry's Avatar
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    Too many ridiculous outfits to just pick one, Robbie. But, have done the Playboy Bunny and harem girl looks!
    These r both very old and horrible quality pics, tho!

    15231.jpg

    18103.jpg
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  5. #5
    Aspiring Member Joyce Swindell's Avatar
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    Our Moose lodge had a "Pimp and Ho" dance once. I went as the Ho and my wife was my Pimp. I wore a very short silver sparkling dress with matching 4" heels. She wore a costume leopard print jacket, stick on mustache and dollar sign bling. It was very fun and I would do it again in a heartbeat. I drove and my wife's parents rode along! Too much fun! However...it didn't take long for me to loose the spikes! lol

  6. #6
    Platinum Member Beverley Sims's Avatar
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    I have achieved all three of those things.

    I was given the playboy bunny outfit from a TV studio I worked for, yes I had to wear it to a costume party for a bet.

    I regularly played tennis years ago in a dress and white ruffle undies and I usee to square dance at one time too.

    The funniest outfit was a white rabbit outfit for an Easter Egg hunt.

    Which reminds me Easter 'aint that far away. :-)
    Work on your elegance,
    and beauty will follow.

  7. #7
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    One of my favorite outfits is also super funny because I sure I just look ridiculous. I break out my biggest forms which are just way too big for me. Put on the massive bra I need to hold them. Then I put on some baby pink tights, my thong style leotard, then my underbust corset. I finish it off with my 6 inch “dancer/hooker platform heels.

  8. #8
    Brandi Brandie.n's Avatar
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    ballerina,supergirl,hooker and a maid all fun
    Flickr- https://www.flickr.com/photos/brandiedaniels/

  9. #9
    Silver Member Leslie Mary S's Avatar
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    Done the Square Dancer thing several times.The yellow 3 piece outfit I picked out when DarkAnGGel wasn't around. She keeps wanting me to burn it fast.
    The face makeup was my doing just to be fun. As for the green dress, It isn't. It is just a piece of cloth and I am holding it in place with my hands. We did not take the green outfit out of the studio but I did once wear the yellow outfit once.

    PS I still have the yellow suit.
    Leslie Mary Shy
    Remember this:
    You do not have to be a man to love a woman, or be a woman to love women's clothes on her or yourself.
    _________________________

  10. #10
    TrueNorth Strong & Fierce Princess Chantal's Avatar
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    When my partner and I dressed up as Ukranian Babas at a restaurant for a perogy dinner party with friends. Dressing theme and event was of my creation where all 20+ friends had to at the least wear a babushka. Have been getting asked from those that attended when are we doing it again!
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  11. #11
    Resident Polymath MarinaTwelve200's Avatar
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    Likely Have to be my GYPSY FORTUNE TELLER----While a bit more elaborate than one I had done several years before, it made me look a lot older and FAT. The eye makeup didn't go as planned either. But it was still "Fun" I just didn't look as good.
    Attached Images Attached Images

  12. #12
    AKA Lexi sometimes_miss's Avatar
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    I made a Playboy bunny outfit out of a shiny one piece black bathing suit (snipped the shoulder straps off), rabbit ears, and the bunny tail, collar & cuffs from a real bunny costume. I purchased the bunny cuff links off of ebay.
    I have several cute maid's uniforms, again, from ebay.
    Cheerleader uniforms, available from real cheer uniform companies.
    I have one prom dress from promgirl.com; there are a few decent plus size dresses there.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  13. #13
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    My Wife once dressed me up in a French Maid's outfit, with Fish Net Hose, and a cute Apron.
    I must admit, If it was not for Halloween, I would never wear it and be seen.
    Rader

  14. #14
    Member Nastasha's Avatar
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    A friends Stewardess uniform. With her blessing and help - skirt, blouse, jacket, bra, panties and hose.
    We were about a year out of high school and she knew I dressed, I had mentioned more than once how I thought the uniform looked awesome and that it would be fun to wear. So when I said it again one day she just looked at me and said OK, you obviously want to try it on so, if you want to, go ahead and try it on.
    It was fun, and just as glam as I thought it would be.

  15. #15
    Platinum Blonde member Ressie's Avatar
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    Nothing too wild. It was an '80s theme support meeting. Asked to dress like an '80s chick rocker.

    80s Theme.jpg80s Theme 2.jpg
    "You're the only one to see the changes you take yourself through", Stevie Wonder

  16. #16
    Silver Member Bobbi46's Avatar
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    I dressed up as a witch for a haloween party. I used a black plastic bin liner as shiny mini skirt. a black tee shirt with the biggest baloons underneath I could find, black licra cycling tights a black pointed hat and broom. I won first prise as well!!!
    I started life a lost man now I am a found woman

  17. #17
    Senior Member Read only Allison Chaynes's Avatar
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    Witch outfit and certain female political figure mask.... went around on Halloween threatening to redistribute candy to kids who were too lazy to trick or treat.
    Life is too short to be boring.

  18. #18
    Member Joan58's Avatar
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    Allison, Perfect
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  19. #19
    tiptoeing thru the tulips ellbee's Avatar
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    Sounds rather boring, but another Halloween witch, here!


    Not really crazy, but actually pretty fun. Definitely memorable, as although I've dressed up quite often for Halloween as various things, this one immediately popped into my head, even though it was like 15 years ago...


    And it was all about THE DRESS!

    Though technically, it was a ball gown.

    A freakin' *gorgeous* one, at that.


    All black, with a stretch velvet long-sleeve bodice, and a HUGE poofy satin floor-length skirt with tons of crinoline underneath.

    The weight & volume & sheer bulk of it was pretty amazing & atypical for me.

    Not exactly something you get to wear every day, ya know?


    Of course, with the usual accessories, like a femmy witch hat, choker, long fake nails, etc.


    Ended up staying home & passing out candy on Halloween. Not a whole lot of trick-or-treaters that evening, but those who did show up seemed to be pretty impressed (and fooled ).


    Was it kinda weird, on some level? Sure, why not. I admit that. Though at the same time, there was no real harm or foul.

    Just a fun & different experience for me. And showed that it's okay for adults to join in & play dress-up, too.


    Oh, and did I mention the gorgeous ball gown??

    (Purged long ago, but whatever. The wonderful memories remain! )

  20. #20
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    The most fun? Probably this one that I wore to Oktoberfest 2018 in Portland:

    https://www.crossdressers.com/forums...1&d=1538282601

  21. #21
    Gold Member Read only Rachael Leigh's Avatar
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    As many have I did the French maid outfit for a party but I also went to a party in what was a pink frilly little girl dress.
    More like a toddler little girl

  22. #22
    Senior Member Asew's Avatar
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    The first outfit I ever wore (and many times after) was a costume for a late 1800s dress with bonnet. It was beckoned me to wear it hanging in the front closet, but definitely something odd to wear indeed.

  23. #23
    Aspiring Member Robbiegirl's Avatar
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    Now how did you get lucky enough to have an 1800s dress and bonnet hanging in your front closet ? LOL

    For your sake I hope it was something fun like this !

    Southern.jpg

  24. #24
    Senior Member michelleddg's Avatar
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    This is Sandy Clifton and me last October at a showing of The Rocky Horror Picture Show at the Wortham Center in Houston. We scarcely turned heads but had a blast. Hugs, Michelle
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  25. #25
    Aspiring Member Robbiegirl's Avatar
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    Quote Originally Posted by Linda E. Woodworth View Post
    Robbie you look GORGIOUS in the included picture.

    Where were you playing? Wimbledon?

    For the record I'd love to dress up as either a square dancer or playboy bunny.
    So Sorry that is the famous female tennis player Chris Everett. I made the mistake of assuming people would recognize her.
    I was just trying to give you guys an example of what tennis dresses looked like back in the day
    Girls Tennis Team.jpg

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