Help with a bet

[925AS]

So a friend of mine asked me to have a challenge with the upcoming NCAA mens tournament. There is no money is involved.

I have to wear a dress for dinner with a bunch of our friends. I can't figure out what she should do if I win.
Having her dress like a guy would not be the same, so I need some help.

 

[Abstract]

Make her wear a strap-on.

 

[mad jew]

...Backwards.



Dunno if that's a punishment though. 😱

 

[GFLPraxis]

Have her shave her head.
😀
We need an evil grin emoticon.

 

[®îçhå®?]

Have her turn up in a bikini.

Dress like a drag queen despite already being female.

 

[iSaint]

Sounds like you'll be fulfilling her fantasy. Why don't you have her fulfill yours?

 

[iBlue]

Have her wear giant granny underwear on the outside of her clothes.

 

[devilot]

Dress like a drag queen despite already being female.

I actually really really like this idea. Probably the only one so far that I think is on-par with you wearing a dress. The other ideas are bit unfair (to her).

 

[emw]

I actually really really like this idea. Probably the only one so far that I think is on-par with you wearing a dress. The other ideas are bit unfair (to her).

Agreed. A man wearing a dress is embarrassing, but it is also short-term. Shaving her head or something like that is out of bounds.

Apparel-related things seem to be the most even:

- Drag queen
- Hooker
- Dress like a man, but wear a fake beard and mustache

I'm assuming this is dinner at a public place?

 

[heehee]

Is she hot? A slutty nurse outfit. 😛

 

[iGav]

I have to wear a dress for dinner with a bunch of our friends.

And that's a challenge??? 😉 😀

 

[shecky]

is a blowjob out of the question?

 

[925AS]

Is she hot? A slutty nurse outfit. 😛

She would wear one anyways.

actually I came up with something and she said she would rather shave her head. I don't want to be completely cruel, the dress thing for me would just be funny and embarrasing for a couple hours.

She just gave me her bracket and all I can say is that I already have this in the bag. She has a 6 seed in the final four and a couple lower seeds advancing pretty far. Odds are on my side.

 

[iSaint]

I actually really really like this idea. Probably the only one so far that I think is on-par with you wearing a dress. The other ideas are bit unfair (to her).

Why is my idea not on-par? Like I said, he's obviously fulfilling her fantasy! 😉

 

[jayb2000]

Haver her wear this:

Assuming that
A) She is not a lesbian
B) That would embarrass her

 

[mattscott306]

Haver her wear this:

Assuming that
A) She is not a lesbian
B) That would embarrass her

I actually like that idea, see how many guys buy her a drink.