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Crossdress him for a lost bet?

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My b/f lost a bet. conditions were hed do whatever i said for a week. After seeing some other polls along this line i thought why not try something similar.
Should i crossdress him as part of his lost bet?
Yes
No, thats just stupid
If yes, how long should it be for
Just a day
A couple of Days
The Whole Week
How far should he be dressed up
Bra
Panties
Stockings/Pantyhose
Skirt
Dress
Blouse or other femine top
Heels
Other, ill tell you in messahe center
Should his dressing be private or public?
Just between the two of you
Invite some of your close friends over
Have some fun with him and and let anyone know
Should i just dress him or take him out places dressed?
Take him lingerie shopping
Just shopping
Out to dinner
Out to a club
Bueaty salon
To the movies
Dont take him anywere thats too mean
Other, ill let you know in the message center
Is this too much to ask of him just because of a bet
No, he was the one that lost
Yes, it goes to far only for a bet
Do you think this will hurt our relationship
Yes
No
He will most likely do anything i say, but i dont want him to do anything he will really hate. Do you think he would be alright with this
Yes
No
Maybe
Will you help me further by giving imput on other things, events, etc. that would be a good part of the bet.
Yes, look for my ideas in the message center
No thanks
This poll was created on 2004-03-22 03:06:35 by Jessica122