cum 3 times before you can sleep

Tie your balls really tight, then tie your legs and hands together. Also don't sleep with anything covering you.

Wear to bed a cum covered pair of underwear

Sleep naked with door unlocked (sheets allowed if you want)

sleep with your balls tied to a weight dangling off the edge of your bed

sleep with tied balls and clamps on your nipples

Sleep in a duct tape pajama and gag

Sleep hogtied with nipples clamps
Mine would be permanent please!

vibrator taped to your dick or balls on high

Sleep on your back, if you wake up on anything else than your back, you are not allowed to cum for a week.

Sleep tightly wrapped in a blanket. Use ropes or tape to make sure it won't unwrap.

Sleep with a mildly painful wedgie all night.

you will insert 9 ice cubes into your ass and enjoy your nights rest

Sleep in nothing but a pair of panties and a stuffed bra no covers ;)

Wearing only panties you must take your covers and pillows off the bed and sleep on them like it's a cat bed.