8 XXX : sissy in chastity

My handsfree sissy cummies gif, in 1.5in chastity cage. x

gfycat.com category @ChastitySissy

New Corset came in! + 2 weeks of chastity update

imgur.com category @Jessica_Ril

My handsfree sissy cummies gif, in 1.5in chastity cage . c

gfycat.com category @ChastitySissy

Locked in sissy boy

imgur.com category @tusspuss

(gif) nearly 3 weeks of chastity made me ride my 8 incher in front of the camera

imgur.com category @shymax

New Account - New Pictures (Chastity webms in comments)

imgur.com category @vegadk

Second post in years, got a chastity hooray!

imgur.com category @ABST1

Super excited to dress up in my new pink cage! [sissy]

imgur.com category @KinkbythePound

Black Dildo in Bed - Sissy Caged

imgur.com category @F_HOLD

Corset + plug + chastity = one pathetically horny trans girl

imgur.com category @queer-doll

pink sissy(who is this?)

gfycat.com category @sissyboychas

Presenting my hole like a good little caged sissy

imgur.com category @LogiTab33

A sissy's greatest ASSet

imgur.com category @LogiTab33

Every sissy should be like this

imgur.com category @bi_luv_xoxo

Locked like every sissy should be

imgur.com category @scribbles96

Pink panties and chastity ( Crosspost r/ShemalesParadise )

imgur.com category @Marigum

Step by step - Sissy

imgur.com category @HazmoSissy

Sentenced to months of chastity, and forced to dress up cute for it.

imgur.com category @PropertyOfMiss

How sissies take selfies

imgur.com category @LogiTab33

Smooth and locked liked a sissy should be

imgur.com category @LacyGracy

First few days in permanent chastity :)

imgur.com category @MySithLady

Lock Up Your Clitty - Sissy Caption

imgur.com category @Mastersissytrainer

Plugged and Caged, there's no better way to be for a sissy

imgur.com category @xLianaAmesX

Sissygirl in a sissy world

imgur.com category @MySithLady

Dressed up in my french maid outfit and locked in my tiny cage!

imgur.com category @RhiannonT

Being cute in my sissy underwear

imgur.com category @MySithLady

caged & plugged, as a sissy should be...

tumblr.com category @sissyslutpupper

Good sissies show off their cage

imgur.com category @LogiTab33

I'm on day 10 of chastity! My longest streak ever! To celebrate, here's 10 of my favorite pics of me locked up.

imgur.com category @xLianaAmesX

Good Girl - Sissy Caption

imgur.com category @Mastersissytrainer

You can always tell an excited sissy by the length of her fairy drop

imgur.com category @sissy_slut_kikme9999

Going to a public kink party tonight with Mistress in lingerie, collar, heels and a chastity cage. I am both overjoyed and very nervous;)

imgur.com category @SissyTrill

There's a clitty in a cage in a lock in some lace in a hole in the bottom of the sea

imgur.com category @drunkencolumbus

One month locked up really makes a big difference in sissy training...

imgur.com category @DaceyCD

Cumming through my cage - I love chastity! [GIF] (x-post /r/sissies)

gfycat.com category @suddenlypanties

[Sissy] She'll be doing all the fucking from now on.

imgur.com category @aimless_ascendant

[Sissy/Trans] Maybe you should just be a girl.

imgur.com category @aimless_ascendant

[Sissy/Trans] Embarassed and denied (x-post from /r/HentaiCaptions)

imgur.com category @aimless_ascendant

Sissy Slut

imgur.com category @[deleted]

Sissy Milking

tumblr.com category @[deleted]

Sissy Maid Bukkake (PoisonCupid)

imgur.com category @thrushed

Sissy Bliss

imgur.com category @[deleted]

Sissy Quicky (from /r/BDSM_Artwork)

imgur.com category @[deleted]

Sissy pegging from Angierosr64

tumblr.com category @account4244

Sissy bound to bed and fucked

tumblr.com category @account4244

Ruined myself 7 times in 6 minutes after coming out of chastity... Here's a little clip :)

gfycat.com category @startersissy

Locked in a fancysteel sissy belt!

imgur.com category @letmenl

Sissy Succubus [OC]

imgur.com category @1stGarden

Sissy asking his mistress for release [Femdom] [Chastity] [Denial] [Sissy]

imgur.com category @Mr_Bluedrobe

Sissy warm up before riding her largest dildo

gfycat.com category @SubEloise