For round 1 I got my right hand on my right ass cheek 10 times. Pretty easy! Round 2 I got one finger 30 times, not too bad. On round 3 I got a pen with toothpaste as my lube. Kinda ow. I didn't use too big a pen though, so fucking myself with it fifty times wasn't so awful. The toothpaste was getting pretty burny by the end, of course. For round 4 I got a big marker (but I'm not very good with anal so I actually used a sort of smallish marker, still bigger than what I'm used to though), and I assumed I had to keep using the toothpaste. This round was tough, five minutes seemed to last so long and my ass really hurt after it was up. Foolishly, I decided to go for round 5. Even though I got the easiest one, just one ice cube, I couldn't do it. I really suck at anal and couldn't get the darn thing inside my pathetic asshole. Feeling like a wimp for giving up in the middle of a round I did punishment five as well as punishment four. And I'm thinking I probably deserve another punishment for failing in the middle of a round.
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20/M
Submissive
Likes: Masturbation, porn, light anal, nipple clamps, edging, spanking, feet, name-calling, teasing, body-writing, orgasm control
Kind of wants to try: cum play, pee, wedgie, role playing
Limits: public, extreme pain, poop, crossdressing, messy
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