Ever Lost A Bet Wear A GG made you dress up in womans clothes?

[brassieres]

I haven't really, but just wondering if this really happens or not? Probably does, but not too often though.

[WandaRae2009]

I could only wish that would happen. I think that is many of our wishes, but then I worry, for us that are not out in the local public, if we do too good of a job would that out us.

[Shikyo]

I didn't lose a bet or anything but I've ended up having a girl polish up my nails. Another time they wanted to do something with my hair so they also played around with that. So in the end even if I would have been against it( I wasn't, of course) I don't think I could have gotten out from that easily because they were rather determined of doing what they wanted to do.

[Annette_boy]

Nope but thats what I told the guys I was locked up with when I got arrested three years ago (It was a DUI and I am not proud of being that stupid ) By the way it worked
Hugs Annette

[Bailey_in_Mansfield]

Well, I didn't lose a bet like you said...but I did go to work dressed as Sarah Palin in order to WIN a bet with some GGs there! Some women had bet me $100 that I wouldn't go as a woman on Halloween. So I picked Palin, enlisted my secretary's help and borrowed some of her clothes, since she and I are just about the same size, and spent an hour and a half with her and her teenage daughter on Halloween morning getting all dressed to the nines. :) And I got my $100, dammit. ;) And compliments on my legs! Gave a quick fake campaign speech while they were coughing up the money, just to show how well I could imitate Palin's accent too. Too bad I can't get the pitch! ;)

[brassieres]

I have to admit she does have a good look.

[docrobbysherry]

In my DREAMS!:brolleyes:

HEY! Isn't Bailey a cutie!?:D

[The_Juggler]

never on a bet, but sort of a dare.
I was "reluctantly" talked into dressing as Sarah Palin for last Halloween.
http://www.crossdressers.com/forums/showthread.php?t=119011

[Loni]

not had such luck.

but I would love to loose that bet every night. :-)


.

[Bailey_in_Mansfield]

never on a bet, but sort of a dare.
I was "reluctantly" talked into dressing as Sarah Palin for last Halloween.
http://www.crossdressers.com/forums/showthread.php?t=119011

That's strange, I saw before you edited it, you said Hillary. >.>


In my DREAMS!:brolleyes:

HEY! Isn't Bailey a cutie!?:D

Huh? *innocent grin* I dunno what you're talking about! *changes avatar* :D

[Kerigirl2009]

Never a bet, However I would take that bet and probably lose on purpous.
When I was a teen My sister dared me to be Cindy Lauper for Halloween. I took the dare (cute flowing skirt) Then I dared myself to go to a halloween party as Cleopatra (Head piece and all)
And when I was even younger but not much my cousins did curl my hair up and treat me like a girl for a while, FUN FUN but that had to end because of my football practice. :) Now who could I make this bet with ---Anyone, anyone, anyone. Darn it all anyways:)

[Amanda Styles]

I never made a bet and lost to a GG, but I did have a girlfriend in HS that kept insisting I come over and let her wash and style my hair, (which was shoulder length) , and put makeup on me. She said she did it to another male friend of mine all the time and he didn't mind. I don't know if it was true or not but he spent a lot of time more time there than I did. I just wished I had let her do what she wanted. She actually got mad when I told her I had already washed my hair.
I should not have let that one get away.

[Stephenie S]

This is an urban myth. Many guys try to use it as an excuse. "Oh yeah, well I lost a bet." No one EVER believes this.

Stephie

[Karren H]

Ohh yeah!!!! I've got standing bets with almost every woman in our office building.... on all kinds of things and if I loose I have to wear their clothing.. But with my bad luck... To date... I keep winning all the bets!!! Noooooooo. Even when I'm lucky... I'm unlucky! Hahahahah.

Race you to the water cooler... Last one there has to wear a dress... Gooooooo. :D

[Bailey_in_Mansfield]

LOL that's awesome... The ladies at my old office job would have figured out way too easily that I enjoyed that stuff too much! ^_^

[The_Juggler]

That's strange, I saw before you edited it, you said Hillary. >.>yah I had considered and planned the costume to be Hillary Clinton in the beginning and later decided I would be Palin as it's easier to do a comical impression of her. And I've never seen Clinton in a skirt
Honestly it was just a skirt suit and I could have called myself any character, celebrity, or otherwise well known person who dresses like this.

I still can't get over that girl rubbing my legs because she couldn't believe her eyes - she never said anything about it since but I sort of wish she would have.

[Bailey_in_Mansfield]

Yeah, Sarah Palin at least has more of a trademark, established look. As soon as I walked in with the red blazer jacket they knew who I was. :P (The McCain/Palin pin I had on helped a bit too, hehe.)

[StaceyJane]

Sarah Palin just did a book signing nearby. Now if only a GG had bet me to go to that dressed as Sarah Palin. :)

[Erica2Sweet]

Ever Lost A Bet Wear A GG made you dress up in womans clothes?

Never.

[Bailey_in_Mansfield]

Sarah Palin just did a book signing nearby. Now if only a GG had bet me to go to that dressed as Sarah Palin. :)

Yeah, she did one near me too. I couldn't go though. :( Didn't have a ticket.

.......WAIT, that reminds me! *heads back over to the "which celebrity would you like to be" thread*

:D

[Emma68]

That's strange, I saw before you edited it, you said Hillary. >.>



Huh? *innocent grin* I dunno what you're talking about! *changes avatar* :D

Nope, doesn't work. Still a cutie :)

[Kate Simmons]

Not really Hon. Actually I'd rather play Strip Poker with some hot GG's I know though (I never lose).:battingeyelashes::)

[brassieres]

Never a bet, However I would take that bet and probably lose on purpous.
When I was a teen My sister dared me to be Cindy Lauper for Halloween. I took the dare (cute flowing skirt) Then I dared myself to go to a halloween party as Cleopatra (Head piece and all)
And when I was even younger but not much my cousins did curl my hair up and treat me like a girl for a while, FUN FUN but that had to end because of my football practice. :) Now who could I make this bet with ---Anyone, anyone, anyone. Darn it all anyways:)

I wanted to be Madonna myself back in the day. And such a beautiful dress in the Borderline video too!




I never made a bet and lost to a GG, but I did have a girlfriend in HS that kept insisting I come over and let her wash and style my hair, (which was shoulder length) , and put makeup on me. She said she did it to another male friend of mine all the time and he didn't mind. I don't know if it was true or not but he spent a lot of time more time there than I did. I just wished I had let her do what she wanted. She actually got mad when I told her I had already washed my hair.
I should not have let that one get away.

Oh, I wish I could find a woman like that!

[Rachel Morley]

Kind of ..... except it wasn't a bet it was a forfeit game and I was 16 years old. Two of my best GG friends used to like to play forfeit games with me where we would ask each other questions and if you got the answer wrong you had to do a forfeit. They always seemed to ask me questions that I didn't know the answer to ... my forfeits were always girly ones like where they would paint my nails and I had to keep the nail polish on for 24 hours, or they would make me shave my legs, or that I would have to wear a barrette in my hair for a day, or I would have to wear one of their sweaters for the rest of the day. :)

Guess what though? ..... I loved it, and I used to pretend that I was all embarrassed about having to do their girly forfeits. Also I would play dumb and give the wrong answer so that I had to do a forfeit. I think they loved the power they had over me ...... so did I ! :D

[brassieres]

When I was a teenager I lost a bet and one of things that I had to do was wear perfume for 10 minutes, but it never really did happen though. I got the best of myself and kept bothering my friend about it wear she just said forget it instead.

She did want me to go dressed up as girl too, however her mom said no. Just as well though, this was back in the 80's and I did not live in a tolerant neighborhood at all.

[aggi123]

I once won a bet from my girlfriend to go out and seduce my roommate while dressed up in her clothes. That was fun.

[trannie T]

Several years ago "Losing the Bet" was my excuse for buying womens clothing. Now my excuse is, "It's for me, I'm a crossdresser."