Sissy Discipline Gallery

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HUBBIES WEEKEND PUNISHMENT DIAPERS™ [Poster] WELCOME TO YOUR WEEKEND! Hubbies Weekend Punishment Dia

HIGHCHAIR HUMILIATION TIME! - “Open wide! Here comes the strained peas choo-choo train!”

MOMMY’S GARDEN FAIRY - Weak and sexless beta-males undergoing ‘baby training’ need to sp

24/7 Sissybaby - “Fully conditioned and regressed, he now enjoys his permanent status as a swe

MOMMY’S KISSY BOY - Mommy insists that her baby gives a warm smile and kisses to all her guest

Getting ‘CHEEKY’ in the Punishment Nursery - People often say he could benefit from a go

‘Baby Mattie’s 1st Visit With Mommy Ellen’ - Part 2 of my true experience with Mommy Ellen is now up

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

“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

I’ve been properly exposed for being a “small-dicked failure of a man” who has been demoted to sissy

I’ve been properly exposed for being a “small-dicked failure of a man” who’s been demoted to sissyba

Poor Sissy! He had been a very naughty boy and so they feminised him and made him wear a bra and gav

‘Baby Mattie’s 1st Visit With Mommy Ellen’ - Part 1 of my true experience with Mommy Ellen is now up

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

The Sissy Alphabet - comes handy…

SISSY EASTER EGG HUNT! The big baby is being very careful to find every last egg otherwise spankies

fmatty:LESSONS IN NURSERY DISCIPLINE - Witness the look of sheer mortification as baby is told that

Happy Easter to everyone!! This is a special ‘Easter Egg’ picture. Please click to be taken over to

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

colleeneris: Always under Strict Discipline by -Celestine Sissy-Maid u.k.- #flickstackr Flickr: htt

chasteandimpure: Flirting With Punishment Up at the crack of dawn, Sissy put the kettle on and wande

bilbng86: -Sissy Discipline = Attitude Adjustment -

My sissy never really had a chance at becoming a real man, Michael (courtney) grew up with a strict

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