Sissy Cumpilation

Ask me anything   Submit   Pictures and Captions of Sissies being diapered, feminized, and humiliated in all sorts of ways!

All pictures have been found across the internet. None of these are my own. Any copyright infringement is purely unintentional, and images will be removed if a problem arises. If you are under 18 please leave and DO NOT follow this blog. This blog is NSFW.

The Human Sissypede!!

The Human Sissypede!!

(Source: gh-05-t, via aaliyahxtaylor)

— 2 days ago with 465 notes
crossdressedcumslut:

For the lovers of used condoms… like me! xxx

crossdressedcumslut:

For the lovers of used condoms… like me! xxx

(Source: straightsissy)

— 2 days ago with 67 notes
ukbdsm:

Amateur-BDSM.org: The home of Amateur Bondage / BDSM on the Internet. Real Amateurs in Pain and Submission.
Amateur Bondage : Ball Gag : Femdom : Humiliation : Amateur-BDSM.org
Submit your Amateur BDSM & Fetish Pictures Here

ukbdsm:

Amateur-BDSM.org: The home of Amateur Bondage / BDSM on the Internet. Real Amateurs in Pain and Submission.

Amateur Bondage : Ball Gag : Femdom : Humiliation : Amateur-BDSM.org

Submit your Amateur BDSM & Fetish Pictures Here

(Source: sirdaddybigcock, via feminizationofsally)

— 2 days ago with 4101 notes
helplesslyregressed:

Go on, Baby.  Pee.  It’ll happen eventually, so you might as well do it before Mama starts to really make you uncomfortable.

helplesslyregressed:

Go on, Baby.  Pee.  It’ll happen eventually, so you might as well do it before Mama starts to really make you uncomfortable.

(via ofteninnappies)

— 2 days ago with 90 notes
helplesslyregressed:

"Mama?  Mama, please, I’ve been on time-out for such a long time now.”
"I measure time by how full your diaper is, not by the clock.  So I guess you had better stop trying to pretend you’re a big girl and let your peepee come trickling out like it wants to."

helplesslyregressed:

"Mama?  Mama, please, I’ve been on time-out for such a long time now.”

"I measure time by how full your diaper is, not by the clock.  So I guess you had better stop trying to pretend you’re a big girl and let your peepee come trickling out like it wants to."

— 2 days ago with 293 notes
helplesslyregressed:

Don’t you look sweet — padded and protected down below and restrained up above so you can’t hurt yourself on all the sharp corners of the world.  Don’t you feel better this way, sweetheart?  Isn’t it so much nicer than being a grownup?

helplesslyregressed:

Don’t you look sweet — padded and protected down below and restrained up above so you can’t hurt yourself on all the sharp corners of the world.  Don’t you feel better this way, sweetheart?  Isn’t it so much nicer than being a grownup?

(Source: diapersfortwo)

— 2 days ago with 349 notes
helplesslyregressed:

Don’t like being strapped to your crib, little one?  Well, let’s let you camp out somewhere really special tonight!  Mommy will come back to get you in the morning, and she expects to see you a happy, grateful little tot!

helplesslyregressed:

Don’t like being strapped to your crib, little one?  Well, let’s let you camp out somewhere really special tonight!  Mommy will come back to get you in the morning, and she expects to see you a happy, grateful little tot!

(Source: diaperpunishmentphotos)

— 2 days ago with 77 notes
helplesslyregressed:

I love how as soon as the spanking implements come out, suddenly she goes from “Mommy, Mommy, please take my diaper off, I don’t need it, I need the toilet, Mommy, I need changed” to “Oh, Mommy, please leave me in my diaper!”

helplesslyregressed:

I love how as soon as the spanking implements come out, suddenly she goes from “Mommy, Mommy, please take my diaper off, I don’t need it, I need the toilet, Mommy, I need changed” to “Oh, Mommy, please leave me in my diaper!”

— 2 days ago with 317 notes
I feel like such a proud mother watching my sissy husband work all those big black cocks!

I feel like such a proud mother watching my sissy husband work all those big black cocks!

(Source: bbchunter, via crossdressedcumslut)

— 2 days ago with 461 notes
crossdressedcumslut:

Mmmm… A double helping for you tonight Sissy… xxxx

crossdressedcumslut:

Mmmm… A double helping for you tonight Sissy… xxxx

— 3 days ago with 16 notes
crossdressedcumslut:

sissycuckwannabe:

Love Love Love it  :) Tessa sissycuckwannabe genericidd@yahoo.com
mistressgabriellebliss:

tumblintodarkness:

Training continues

Suck it


xxx

crossdressedcumslut:

sissycuckwannabe:

Love Love Love it  :) Tessa sissycuckwannabe genericidd@yahoo.com

mistressgabriellebliss:

tumblintodarkness:

Training continues

Suck it

xxx

— 3 days ago with 245 notes
"What? You think you make one pissy diaper and you’re done? Hahaha oh nooo sweety! We’ve still got a 30-pack of diapers for you to get through, and you haven’t even had to make stinky in one yet! Now that i can not WAIT to see! Now quit your whining and hold still! You don’t wanna add another week to your chastity cage do you?”

"What? You think you make one pissy diaper and you’re done? Hahaha oh nooo sweety! We’ve still got a 30-pack of diapers for you to get through, and you haven’t even had to make stinky in one yet! Now that i can not WAIT to see! Now quit your whining and hold still! You don’t wanna add another week to your chastity cage do you?”

— 3 days ago with 22 notes
#caption  #diaper