Here's an anal dare for everyone
Choose two buttplugs or common objects or dildos that can be used instead, one should be very comfortable to use anally and one should be big enough to fill you up but such that you are still able to perform anal thrusts with it.
Now insert the smaller comfortable plug/object in for an hour, then after an hour, keep spinning
this wheel until you get "STOP" and doing the corresponding anal thrusts. Start with the smaller dildo and whenever you get "SWAP", switch the dildo so the first swap will get you to use the bigger dildo for subsequent spins until you get swap again. Note that after spinning each time, the option you landed on gets removed from the wheel. Have fun and feel free to modify the dare a bit based on your thresholds.