Results 1 to 22 of 22

Thread: Bet a friend to wear womens' clothing

  1. #1
    Member
    Join Date
    Oct 2016
    Location
    Dallas, TX
    Posts
    378

    Bet a friend to wear womens' clothing

    When I went to the mall the other day with my friend, we passed by a bridal shop. Naturally being a crossdresser, the gorgeous lovely gowns caught my interest. Since I have not come out to him yet about my crossdressing, I couldn't very well go into the shop and look at them. But I did ask him "Would you wear a wedding gown and walk around the mall if someone bet u $100?" He said no and then I said $1000, and he said yes he would. Obviously I don't have to tell u that I'd do it, but not for $100, so much as not to let onto him that I crossdress and am willing to do it without much persuasion.
    How many out there have friends who don't crossddress but would take that bet?

  2. #2
    Aspiring Member
    Join Date
    Aug 2013
    Location
    Northern Georgia
    Posts
    515
    Interesting. I've been thinking about inviting a friend over to watch the Super Bowl and then making it interesting by making a bet. The loser has to dress up as a woman. Of course I would hope to lose.

  3. #3
    Member ambigendrous's Avatar
    Join Date
    Dec 2012
    Location
    San Jose, Ca, USA
    Posts
    328
    I've often wondered how to pull off a "Come as Your Spouse" party, without being the one to suggest it!
    Ambigendrous
    Wealth should not be measured by how much you have, but by how little you need - anon

  4. #4
    Member
    Join Date
    Oct 2016
    Location
    Dallas, TX
    Posts
    378
    Quote Originally Posted by Confucius View Post
    Interesting. I've been thinking about inviting a friend over to watch the Super Bowl and then making it interesting by making a bet. The loser has to dress up as a woman. Of course I would hope to lose.
    If I were to bet, I'd do it for money. Then I'd use that money to buy a new dress or something else feminine.

  5. #5
    Banned Spammer
    Join Date
    Aug 2008
    Location
    Between here and there but mostly here close to the donuts.
    Posts
    22,257
    The old bet line huh?
    He will have you figured out soon so be ready for the talk.LOL
    If you ever get caught dressing by a friend and you say you lost a bet he will know you are lying trust me.
    Its the oldest lie in the book.

  6. #6
    Aspiring Member LaurenS's Avatar
    Join Date
    Jun 2014
    Location
    Western Oklahoma
    Posts
    520
    Everyone has a price.
    You are you. You are beautiful. Labels are worthless.

  7. #7
    Platinum Member alwayshave's Avatar
    Join Date
    Dec 2011
    Location
    Washington, DC
    Posts
    12,771
    Actually, at my local pub there was a bet between fans of rival teams for a playoff series. The losers showed up in drag. One of the guys looked so good that his girlfriend broke up with him at the pub while he was dressed.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  8. #8
    Member tylia's Avatar
    Join Date
    Nov 2013
    Posts
    401
    If you lose the bet and show up with the perfect fitting outfit,perfectly coiffed wig and your make up is flawless.....there will be questions....unless your wife is the same size as you. .....Hard to come up with the femme walk overnight also.......just sayin"

  9. #9
    Reality Check
    Join Date
    Feb 2014
    Posts
    8,842
    Then there's the old "Would you sleep with me for $100?"

    She answers "no."

    "Well would you sleep with me for $1,000?"

    She answers "yes."

    He answers "So we've established that you are a prostitute, now we're just haggling over the price!"
    Krisi

  10. #10
    Aspiring Member KymG's Avatar
    Join Date
    Apr 2017
    Location
    Basingstoke, Uk
    Posts
    590
    There is walking around in the wedding dress, and then there is walking around in the dress, 100% dolled up.
    I would if i could get away with it as a bet.....

  11. #11
    Reality Check
    Join Date
    Feb 2014
    Posts
    8,842
    As tyla pointed out, if most of us showed up "in drag" around our friends as a result of a bet or come as your spouse party or a Halloween party, we would be read as a crossdresser pretty quickly. What normal guy has a pair of silicone breast forms, hip and butt padding, a perfectly fitted wig, perfectly fitting women's shoes, shaved legs, and full makeup?

    People will figure out that we don't do this just once a year.

    If you don't want your family or friends to know you wear women's clothes, don't dress up around them.
    Krisi

  12. #12
    Girl about Town Jodie_Lynn's Avatar
    Join Date
    Sep 2005
    Location
    Catskill, NY
    Posts
    1,181
    ... or show up looking like a badly (cross)dressed Ken doll and hope a lady friend decides to improve your style.....

    (This is for all the "I wish someone would 'force' me to dress like a girl" crowd )
    Before you can love another, you must first like yourself

    I Aim To Misbehave

    Labels belong on BOXES, not PEOPLE!

  13. #13
    Gold Member NicoleScott's Avatar
    Join Date
    Mar 2008
    Location
    Mississippi
    Posts
    5,000
    RD, how do you know your friend doesn't crossdress? After all, he doesn't know that you do.

  14. #14
    Heisthebride Heisthebride's Avatar
    Join Date
    Jun 2010
    Location
    Minnesota
    Posts
    335
    Quote Originally Posted by Krisi View Post
    As tyla pointed out, if most of us showed up "in drag" around our friends as a result of a bet or come as your spouse party or a Halloween party, we would be read as a crossdresser pretty quickly. What normal guy has a pair of silicone breast forms, hip and butt padding, a perfectly fitted wig, perfectly fitting women's shoes, shaved legs, and full makeup?

    People will figure out that we don't do this just once a year.

    If you don't want your family or friends to know you wear women's clothes, don't dress up around them.
    I managed to pull this off for Halloween one year, but it took a lot of scheming.
    1. I made a bet with a girl that escalated until she said I would have to wear a wedding dress one night in Las Vegas, I agreed if she would wear a gorilla suit if she lost. Sadly, I won the bet and she copped out.
    2. In the background I emailed the annual host of our Halloween party to “gather intel” on how the bet would turn out, letting her know what I would have to do if I lost.
    3. 3 months later, after the bet was over, the Halloween host announced to a group of friends that I should go to the party as a bride since they didn’t get to see it in Las Vegas. Seed planted earlier came to fruition. Total luck.
    4. “Accidentally” win an EBay bid for a wedding dress, tell the story to the Halloween host saying it probably won’t even fit.
    5. Convince 2 male friends to be my bridesmaids.
    6. Hire a makeup artist to do my bridal makeup, explains away why my hair and makeup were so good.
    7. Attend party as a bride in full regalia, I’m not the only one crossdressed because of my bridesmaids. But I look the best because I have professional makeup. People asked I for I shaved my legs, I said of course I did, why wouldn’t I?

    6E15E31C-2617-457F-AF5D-ECDC3A40FEC5.jpg
    Rebecca Bas

  15. #15
    Female Illusionist! docrobbysherry's Avatar
    Join Date
    Sep 2007
    Location
    Orange County, Calif.
    Posts
    24,843
    Good one, Krisi! I was going to post that.

    The point being; it's one thing to chat about crossdressing with vanillas for money. But, quite another to actually have a vanilla man do it!
    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!

  16. #16
    Member StephanieM's Avatar
    Join Date
    Dec 2016
    Location
    Tallahassee
    Posts
    216
    Quote Originally Posted by Tracii G View Post
    The old bet line huh?
    He will have you figured out soon so be ready for the talk.LOL
    If you ever get caught dressing by a friend and you say you lost a bet he will know you are lying trust me.
    Its the oldest lie in the book.
    Yes I don't believe anyone buys that line. I have used it before but I put a twist on it, I said I was bet that I wouldn't go out dressed like this and I won.

  17. #17
    Junior Member
    Join Date
    Jun 2017
    Location
    North Carolina
    Posts
    55
    Heisthebride, you are too much, you devious Girl!! Remind me to never wager against you - on anything. I think I would lose. Oh what the heck, let's wager on the Super Bowl.

  18. #18
    Junior Member
    Join Date
    Aug 2017
    Location
    England
    Posts
    40
    A friend jokingly dared me to cosplay as a princess at comic con. I was like "jackpot!"

    After attending quite a few cons, I'll assume MANY men get this dare lol.

  19. #19
    Banned Spammer
    Join Date
    Aug 2008
    Location
    Between here and there but mostly here close to the donuts.
    Posts
    22,257
    Sabrina I think cosplay and comic con type men don't need to be dared to dress up as a female comic character.
    I see so many online it pretty common actually.

  20. #20
    Platinum Member Beverley Sims's Avatar
    Join Date
    Nov 2011
    Location
    Lowestoft UK. Beverley was here.
    Posts
    30,955
    Is cosplay just a way to hide your crossdressing? :-)
    Work on your elegance,
    and beauty will follow.

  21. #21
    Member Lea's Avatar
    Join Date
    May 2007
    Location
    South east
    Posts
    359
    I always enjoyed reading heisthebride blog.

  22. #22
    Member
    Join Date
    Oct 2016
    Location
    Dallas, TX
    Posts
    378
    Quote Originally Posted by Beverley Sims View Post
    Is cosplay just a way to hide your crossdressing? :-)
    I've never really been into cosplay, and didn't even know what it was when I would dress up as Princess Peach. But I know I would absolutely love cosplay, and would probably want to dress up mostly as female characters. Funny enough, I haven't dressed as Peach since I started crossdressing, or even given the pink princess outfit much thought. But I do know I'd totally jump at the chance to dress up as her, or any other princess. I think they are gorgeous, cute, lovely, etc.

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •  


Check out these other hot web properties:
Catholic Personals | Jewish Personals | Millionaire Personals | Unsigned Artists | Crossdressing Relationship
BBW Personals | Latino Personals | Black Personals | Crossdresser Chat | Crossdressing QA
Biker Personals | CD Relationship | Crossdressing Dating | FTM Relationship | Dating | TG Relationship


The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs.
We are always trying to improve the forum to better serve the crossdresser in all of us.

Browse Crossdressers By State