Get in a shoulder wedgie then roll a d-20. If its a 1-4 hit yourself in the balls that many times. If its 5-8 do that many squats. If its 9-12 put on a second pair and get in an atomic for that many minutes. If its a 13-19 do that many squeaky clean pulls. If its a 20 do all of the above, either for 20 minutes or 20 times where applicable.

You can stop when you roll the same number at least three times

(prefer long and/or creative dares)

https://www.getdare.com/bbs/showthread.php?t=321916

Do this dice dare

Use a piece of string to keep yourself in a front/back wedgie for an hour. (The string should look like suspenders, going through the back legholes, over your shoulders, then tying through the front leg holes)

Wait until you really really need to pee then tuck yourself. If you dont start peeing straight away, then start giving yourself regular wedgies. You can stop when you pee yourself. Afterwards, take off yoyr belt toie a wedgie through your belt. Keep in the permanent pissed in wedgie for an hour before cleaning yourself up.

Atomic wedgie do not stop till you start ripping you undies

Pull so hard your ass hurts

Sit in a chair wedgie for 30 minutes, then give yourself an atomic wedgie right after for 5 minutes

Do a shoulder wedgie with something in your ass for 1 hour

Chair wedgie for 20 mins

Sit in a chair wedgie for an hour while watching wedgie videos

A thong bra connection, with a granny panty shoulder wedgie layered on top, hidden under clothes for a day

I have a challenge for you. You need to reach 100 points in a week.

Here are your options :

Frontal/Normal > 2 points per hour
Shoulder/Bra connection > 3 points per hour
Hanging/Dangling/Chair > 5 points per hour

For any wedgie done in public, the points are doubled.

If you haven't reached 100 points in a week, spank yourself X times.
X is the number of points you have reached.

Put on a thong and a pair of granny panties, mix honey, and crushed potato chips or dry rice into the back. Sit in that for 3 hours before giving yourself a shoulder wedgie, if not stretchy enough do a propeller wedgie.

Give yourself a backwards wedgie, then blindfold yourself before you stand in front of a window. Atwitch your play with yourself for 1 min before removing