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PrinceOfCanada
PrinceOfCanada

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[C][WIP] Sam in Diaper Prison

Squeezed one more commission into my current batch for a friend :3 Will be opening them up later this month or early next. Here we have Sam in the same Diaper Prison that Rudy was sent to recently. Except this cutie seems to have earned himself level 3 security, which means being tightly strapped down to the crib for a full night of chastity and vibrator torment. Also it seems as though the overseers of this prison have been revealed: Each boy gets their own personal Mr. Bear as a guard :3

[C][WIP] Sam in Diaper Prison [C][WIP] Sam in Diaper Prison

Comments

Fair point, I guess I have two ticklish boys of mine that would be elated to have their tiny awfully ticklish soles tormented to no ends along the rest, not that they enjoy footwear (matter of fact they despise it) but it's not like we give them any choice either 😌

ClmUbrn

I bet they have rubber booties with built-in ticklers for exactly that purpose ^^ Gotta makes sure the prisoners are constantly testing their restraints after all!

PrinceOfCanada

I'd reckon I'd take a lifetime membership if they propose an extra feet tickling option, I would go sooooo crazy from this (⁠*⁠´⁠ω⁠`⁠*⁠)

ClmUbrn

O_O! The idea of a shared crib hadn't even entered my mind, and holy cow! Thinking about the number of ways they could use that to torment us both even more is making me realize I'm gonna need to lock MY cage on soon! <_<

thewebb414

Hehe, the real question is if there's two cribs in a shared cell, or if the prisoners share one ^^

PrinceOfCanada

Oh the leaking and straining would be my favorite part, especially if I had to watch my pamp swell while I'm pleading for mercy from the vibrator. And heck, let's go find this place together! Maybe we can convince them to put us in a room together so we can watch each other squirm and struggle to escape while we're tormented. I have to imagine it would be so fun to get to hear your muffled pleas alongside mine as we slowly go mad and slip into endless horny oblivion! <_< *blushes intensly*

thewebb414

Oh he's definitely strapped extra tight, all prisoners are ^^ He's definitely earned the max thickness pamps as well, which I imagine actually get thicker the more he leaks into them as an extra source of humiliation. With how tight that cage is too, the orgasms are going to be extremely frustrating and sparse, just lots of leaking and straining to look forward too >:3 Thanks so much, glad you like it <3 I agree, I'd join him in an instant ^^

PrinceOfCanada

*drools on myself while imagining being in his position* Man, I knew level 3 would be intense, but the amount of jealousy I have for this boy cannot be put into words. Those straps just look SO tight and restrictive and the matching identification on both the straitjacket and the diaper is an excellent addition IMO, and seeing how big that diaper already is, god his muffled pleas for mercy must sound like a choir of angels by this point. My only hope is they leave him there until his cream is leaking out of every inch, and his eyes are rolling back in his head in maddening frustration with each orgasm! Now I just have to find this prison and convince them to "admit" me permanently, and hope that a bunch of big strong guards drag me away kicking and pleading for mercy while Mr. Bear grins at me with that beautiful crop! Heck, I'll even tip them if they pull every single strap EXTRA tight! Bravo again!

thewebb414

I definitely want to draw more Gregory! ^^ And I haven't been working on the Demon Lands, I have been enjoying focusing on other projects in the meantime :3 I will probably get back to it before the end of the year though.

PrinceOfCanada

Cute as always. Would love to see more of Gregory from fnaf. And do you have an update on demon lands

Bongo_drum


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