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.

This isn’t really how you expected “swinging” to go…

This isn’t really how you expected “swinging” to go…

(Source: fedomsissy, via sissychristie)

— 18 hours ago with 92 notes
tammynicolesmith:

Mommy insists on changing me on a diaper changing station when we are at the mall. 

tammynicolesmith:

Mommy insists on changing me on a diaper changing station when we are at the mall. 

— 19 hours ago with 17 notes
Sissy photshoot.  He’s a cheerleader today!! And as you can see he’s not too happy about it…

Sissy photshoot.  He’s a cheerleader today!! And as you can see he’s not too happy about it…

(Source: staykinky, via krystel74)

— 20 hours ago with 129 notes
"That’s right! Suck his dick you pathetic excuse for a husband! I’m gonna do what you always did to me and slam your head all up and down that cock! Uh oh was that a little gagging a hear? OH WELL!!"

"That’s right! Suck his dick you pathetic excuse for a husband! I’m gonna do what you always did to me and slam your head all up and down that cock! Uh oh was that a little gagging a hear? OH WELL!!"

(Source: clothedfemalenudebisexualmen)

— 20 hours ago with 183 notes
Waiting for another “customer”…

Waiting for another “customer”…

(Source: slaveshouse)

— 20 hours ago with 66 notes
"There’s no need to cry sweetheart, look how pretty you look! You’re going to be the most beautiful girl at the pageant! Of course, you’ll be the only boy in the pageant but no one needs to know that! You just be a pretty little a fairy and do your little thing for mommy! If you win…I might even let you out of your chastity belt for a little bit.  Now quit your crying! We don’t want to smear your makeup!”

"There’s no need to cry sweetheart, look how pretty you look! You’re going to be the most beautiful girl at the pageant! Of course, you’ll be the only boy in the pageant but no one needs to know that! You just be a pretty little a fairy and do your little thing for mommy! If you win…I might even let you out of your chastity belt for a little bit.  Now quit your crying! We don’t want to smear your makeup!”

(via sissyjacqui)

— 21 hours ago with 161 notes
"It won’t be that bad sweetheart, you’ve sucked some dick before! Granted, there’ll be about 12 more of them but you’ll get used to it! And just think of all the cum you’ll be getting!"

"It won’t be that bad sweetheart, you’ve sucked some dick before! Granted, there’ll be about 12 more of them but you’ll get used to it! And just think of all the cum you’ll be getting!"

(Source: strictly4mygoddess, via femdom-sm)

— 21 hours ago with 363 notes
This event is known as the “Peg Race”.  In which the two sissy pledges have to make to the end to see who gets to be let out of chastity, and who has to spend the week in the dungeon…

This event is known as the “Peg Race”.  In which the two sissy pledges have to make to the end to see who gets to be let out of chastity, and who has to spend the week in the dungeon…

(Source: cuckoldingnl)

— 22 hours ago with 72 notes
Almost all of the new pledges at Delta Iota Kappa fall for it.  During their first party of the year, we just have to see how many guys we can lure back to our sorority house.  Then it’s just a matter of slipping them a couple Rufies, getting them tied up and dolled up, and watching the panicked looks on their faces as they wake up to the new house they’ll be pledging.  Let’s just say there’ll be much more than paddling and drinking in their future. Yes, these new little sissies are going to be in for a rough semester. 

Almost all of the new pledges at Delta Iota Kappa fall for it.  During their first party of the year, we just have to see how many guys we can lure back to our sorority house.  Then it’s just a matter of slipping them a couple Rufies, getting them tied up and dolled up, and watching the panicked looks on their faces as they wake up to the new house they’ll be pledging.  Let’s just say there’ll be much more than paddling and drinking in their future. Yes, these new little sissies are going to be in for a rough semester. 

(Source: beautibound)

— 22 hours ago with 34 notes
#sissy sorority  #captured  #bondage  #tied  #forced fem  #caption  #fantasy 
teased-pleased:

Keep shooting that cum for me. I want everything youve got in those squeezed balls.

teased-pleased:

Keep shooting that cum for me. I want everything youve got in those squeezed balls.

(via diapermarty)

— 23 hours ago with 2725 notes
Training the sissy for the double stuff.

Training the sissy for the double stuff.

(Source: femdomboss, via diapermarty)

— 1 day ago with 47 notes
"Louder!"
"AHHHhh! Ahhhh! I wet the bed like a little baby!"
"LOUDER!"
"AHH!! AHHH! I WET THE BED LIKE A LITTLE BABY!"
"Keep your head in that wet spot! Smell your fucking pissy mess!"

"Louder!"

"AHHHhh! Ahhhh! I wet the bed like a little baby!"

"LOUDER!"

"AHH!! AHHH! I WET THE BED LIKE A LITTLE BABY!"

"Keep your head in that wet spot! Smell your fucking pissy mess!"

(Source: yourkinkymistress, via lilbabytaytay73)

— 1 day ago with 172 notes
She’s just doing a systems check to make sure you’ll be on your best behaviour for the party tonight…

She’s just doing a systems check to make sure you’ll be on your best behaviour for the party tonight…

(Source: yourkinkymistress, via diapermarty)

— 1 day ago with 182 notes