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?

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.

I've often wondered how to pull off a "Come as Your Spouse" party, without being the one to suggest it!

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Originally Posted by Confucius

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.

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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. :)

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.

Everyone has a price.

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.

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"

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!"

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.....

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.

... 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 ;) )

RD, how do you know your friend doesn't crossdress? After all, he doesn't know that you do.

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Originally Posted by Krisi

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.

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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?

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Good one, Krisi! I was going to post that. :heehee:

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!:tongueout

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Originally Posted by Tracii G

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.

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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.

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.

A friend jokingly dared me to cosplay as a princess at comic con. I was like "jackpot!" :D

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

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.

Is cosplay just a way to hide your crossdressing? :-)

I always enjoyed reading heisthebride blog.

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Originally Posted by Beverley Sims

Is cosplay just a way to hide your crossdressing? :-)

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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.