Diaper Humiliation Caption Gallery

bucky's arm cute asses neutronstarmerger lauravanarendonkbaugh gaboy1231

CAUTION; SPILLED MILK! [Censored Version]Make Sure To Diaper Your Sissy Before Letting Him Read Book

Pampers Olympics (His New Mommy - Issue 9)*Another homage I made in honor of WhAP! (Women Who Admini

“THE EMBARRASSMENT FILES: Dolly Show-and-Tell Time!” I am ‘encouraged’ to ge

Looking sweet for Mommy as I make wettums for her in my Princess Pampies as dolly wets her Pampies t

SPANKED INTO SISSYHOOD: ‘Baby-sulking’ doesn’t pay! See his terror as he gets spanked outdoors in fr

Courtney was dressed as a sissy locked in chastity, and wearing a diaper, then taken to the local st

What was it, how do you explain it?xoxo

Another Dirty Dirty Gif xoxo

You’re so naughty! Aren’t you…xoxo

sissy-caroline: Frills galore. Hehe sissies should always be at maximum poof and thick diapers

Tom was on the verge of tears. This was going to be the worst day of his life. “It’s just a kink eve

They were obviously trying to get rid of her. Scraping every single boundary set in their contract.

ClickFinas phonecamera did it’s job and accuratly captured the worlds, or in this case, her coworker

There was no way she could hide it. Bright colours, loud crinkles and ludicrously thick, this diaper

Stella looked like an idiot. But at this point in time, she couldn’t care less. She didn’t care abou

PART 2 (Sissybaby Tea Party): As much as I dreaded the intense humiliation, my knoblet would spurt c

A little diapered maid gets the window extra nice and clean … because it faces the street out

Look, little one, there are mirrors in that shop window. Let’s wait for these people to move

There was a wild padded puppy that could be found strolling through MAL last night after a friend fo

@akalpha recently came over before I was about to take a nap and decided he was going to have some f

bimboslaveslutfuckbitch: Wanna try em all

ericaashcroft: beta-girlfriend: callalilly849: therealhotpotatogirl: collegecuckcake25: @subkrissyh

I so want those frillies

nikkidlsd: satinsissy-me: girdleluv: futuretransformedsissy: I would I’d beg to wear that dres

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