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Requesting Humiliating or/and painfull afternoom

Thank you puppie_slutty i will do the first one second can't be done with cage and clotheping
Alright that's fine then, sorry I didn't see the part at the top saying you were caged. You can put the toothpaste on your asshole instead(doesn't have to be inside). Reapply every 3 deaths. If you die 10 times before beating a boss, squirt a little toothpaste inside your anus.
 
So far i failed to beat a boss before my ten run
I will now kneel...
I also apply toothpaste on my ass (i really dislike that....)
Nipple hurt, and balls also

I will happily exchange some pain dare for humiliating one... i will keep playing until i reach 25 deaths i think after that i will ask to release some of the pain Sirs
 
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22 deaths
I try to kneel on rice but that with the other pain was too much

So i request a punishment from you DMD ?

I also remove the clotheping (nipple hurt like hell, i'm shaking from it (and from the cold))
 
Sorry not been active for a minute there - anyone can give you the punishment, if I come up with something I'll let you know
 
You should have kept kneeling then - you're lucky they didn't specify the object
 
can i have a punishment who not mess with my sleep ?
Dmd Sir having something in my ass is less problematic than cold for sleeping
 
I will allow one item to cover you while sleeping(sheet, blanket, etc) No more complaining or else you’re sleeping on the floor
 
Thank you puppie_slutties and since i haven't beat a boss i wet myself naked in the bathroom
Hope you enjoy it Sir
 
bwahahaha that was cute

the underwear should be a gag if you need any further punishments later lol
 
i always need a good punishment Sir, should i put the underwear gag right now since it's wet ?
 
Take a close up picture of your spread out asshole wide open. Then draw its shape with sharpie on your belly. Post them side by side
 
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