Spank his balls. Have him spread his ass cheeks as far as they'll go then beat him directly on his anus. Once you've got that nice and sore, ram something (hand, fingers, dildo, carrot ... etc) into his ass and then fuck him with it. Grab his balls, squeeze tightly, and then lead him around backwards using them as a leash
Later:
Quote:
Originally Posted by linearizationcannon
I think you need to lay on your back with your legs spread, and hold your pussy lips open with your hands so that he can belt the interior of your pussy 45 times ... while you count and thank him for each strike.
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Repeat this one, only 100 times (also knees UP, legs spread). Then use a stiff, prickly, cylindrical hairbrush to fuck/scour her pussy while she squeezes it tight and pushes it even tighter with her hands. Spank her pussy 10 more times and rub salt into it. She then has to start handwriting her report of how this went while he fucks that sore, tender pussy as brutally as possible. She cannot finish the report until he has finished fucking her (whereupon he can choose to returning to tormenting her pussy in other ways). Once he has, she can announce that she thinks she's done. If he judges it a long and thorough enough report then this dare is done. If not, back to writing. If he is ready for round 2 of fucking her abused pussy, he can start again and her report cannot be finished until he does and agrees that it is finished.
Afterwards transfer the handwritten report into an electronic report and post it here.