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Cheeky’s PM Dares

Cheekyftm

Active member
Joined
May 28, 2026
Location
USA
Gender
Trans man
Pride
Transgender Transgender
ATOMIC - I will stay in an atomic wedgie for 5 minutes

HANG UP - I’ll do a hanging wedgie for 1 minute

TIPPY TOES - I’ll do a dangling wedgie for d20 minutes

JOCK LOCK - I will get in a jock lock wedgie until I can free myself without using my hands. If I fail to do so within 25 minutes, I have to complete CLEAN AS A WHISTLE with max amount of swipes (45) immediately after the jock lock

SISSY - I’ll wear my most feminine pair of underwear the next time I change clothes

PROPELLER - I’ll do a propeller wedgie with d20 amount of twists

BOOKWORM X - I have to stay in a wedgie of your choice while reading X (5-30) pages of my current book

CLEAN AS A WHISTLE X - I’ll do X (5-45) swipes of squeaky clean wedgie

WEDGIE YOGA - I’ll do upward facing dog with the front of my underwear between my teeth for 5 minutes

SPIN - I will spin this wheel and complete whichever task it lands on

ADD X - I’ll add X (your choice of wedgie dare) to the wheel above

PASSWORD X - I’ll play X (5-15) levels of The password game in a wedgie of your choice

DO THIS - Send me any wedgie pic and I’ll do my best to recreate it (does not include pic of the result)

More to come! Any suggestions?
 
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