So here is what I will do.
Underwear: Thong, push up bra.
Top or Bottoms: Dress (Women's Haloween Costume) (If it fits. If it doesn't) Women's Frilly Top + Regular Skirt
Hoisery: Black Tights/Pantyhose
Shoes: Vans/COnverse(Well... it'll be whatever I have)
Makeup: Lip stick, Eye shadow, blush, eye liner, mascara (Or rather, whatever of that I find and can put on)
Extra: Penis tucked back,
Dare:
Masturbate and moan while doing it.
Webcam: Tell them you've lost a bet and you have to do atleast one thing they say. Do whatever they say that stays within your limits.
Inside: Watch a music video by a female artist and try to recreate that video
(I only have to do the first one to not get a punishment. The others are extra.)
Duration: 3 Hours (I take that to mean how long i have to be in outfit - I will be doing other stuff too during those 3 hours)
Punishment for failure:
Fall asleep while wearing outfit.
I'll post pics once completed!
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