8 XXX : sissy time

A Part-Time Sissy

gfycat.com category @sgameonsexy

I remade the part-time sissy gif

gfycat.com category @[deleted]

Album of gifs for you all! Haven't put one together in ages and thought it was about time! (none of it is OC)

imgur.com category @Digging-For-Gold

Tumblr Preview #5 [Ten this time b/c I love my bitches]

imgur.com category @seattlejasmine

It's only a matter of time.

tumblr.com category @[deleted]

The moment you realize you've been wasting your time with girls

imgur.com category @str8-to-sissy

Some Quality Time Together

imgur.com category @Assassinshadow1

There better be DADDIES in my inbox at all times ;)

imgur.com category @[deleted]

(SW)All the time

imgur.com category @Ilovesissygirls69

It's time to play with some... panties

imgur.com category @AndyPeel

First time posting on this subreddit.

imgur.com category @LilaTrap

Im in position, now would be a good time...

imgur.com category @tyheelslove

First time sharing a photo (x-post from /r/sissymaid)

imgur.com category @nikki258

Couples first time posting on this page.. feedback would be much appreciated :)

imgur.com category @PassionateChemistry

First time posting here...hopefully you guys like my big ass :)

imgur.com category @SissyJenna13

First time posting, Please humiliate me

imgur.com category @SissyAmberxxx

First time sharing, be nice please

imgur.com category @Eva_sissy

It's a little late to get off your knees. Time to live with your decisions sissy.

imgur.com category @Sissy-Carmella

It's Almost Time, Sissy

imgur.com category @PHXCurious

It's decision time, sissy!

imgur.com category @Streeet_Life

First time post.

imgur.com category @Keira2000

Since you all loved my last caged orgasm! (I'll get a better angle and bigger dildo next time

gfycat.com category @DaceyCD

Mommy and Daddy are away so it’s time to play ☺️

gfycat.com category @jamiedylan18

You can't tell in the photo, but I gave myself a creampie for this shot. Better luck capturing it next time, perhaps?

imgur.com category @helpmedrip

Taking Chance for the First Time

imgur.com category @addyftw1

the front this time :)

imgur.com category @AliciaSub

First time locked up. 2 hours for every upvote.

imgur.com category @tendersiss

Love my cage time.

imgur.com category @Keira2000

Familiar with chastity, new to sissification. First time poster. Am I doing this right?

imgur.com category @secretsissykins

Got sissied up for the first time with my cage on and took some pics!

imgur.com category @JessicaSissyCumSlut

First time posting, should I do it more?

imgur.com category @sissy_slut_kikme9999

Crazy to think my first time with dick inside my hurt and I thought I’d never want it. Now I crave it and I’m making this face. I’d like to thank my cage for that. :)

imgur.com category @[deleted]

First time using my first dildo! Love it soo much!

gfycat.com category @My-N-quite-SFW-alt

Lost my virginity today wearing this. Daddy came in my ass then locked me back up after I sucked him off for a long time.

imgur.com category @GimmeDaZoppity

First time in chastity, you can tell I’m a bit excited!

imgur.com category @Thisisntathroaway

Is it worth going back to? It always felt REALLY good and also really fulfilling but I'd always end up stopping because it seemed like too much work or wasn't worth my time. Also, I'm new to this sub hello everone! (Pic is a few months old)

imgur.com category @chromosomeFarmer23

[HANDSFREE] I cum twice in less than 30sec(1st time i cum on my dildo & 2nd time after i insert the semen in my ass)

gfycat.com category @DaisyCartonCD

Cant wait to spend some time locked up agian!

imgur.com category @CDTasha

Gave a blowjob for the first time yesterday and I loved every second

imgur.com category @SisKayra

\\ CHASIS CORPORATION -- Sissy Meal Time. //

imgur.com category @CHASIS_CORP

Thought for sure I was going to get fucked for the first time ever last night. Got flaked on

imgur.com category @Therealjennibaby69

milking time fun xD

imgur.com category @sleepinghottie

Every time I post a new pic or video, I secretly hope that some of my guy friends recognise me :P

gfycat.com category @Nina_LaBelle

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

gfycat.com category @startersissy

Trust me, no matter how many times you try to stop it, you can't escape becoming a cock hungry sissy princess..After all, if you didn't want it, why are you here? ;)

gfycat.com category @leebsisme

While ago I was a straight boy, but now I'm almost bending over... And I think my panties are too skimpy to save me this time..

imgur.com category @Popiecolo

The last time is far too long ago, feels good to be wearing this again..

imgur.com category @serpentipes

Feeding time for the doggy bitch!

imgur.com category @sissy-anisha

First time being a sissy in public

imgur.com category @mrcave81

I tried doing my own makeup for the first time before chores, instead of having it done for me by my friend! She says it was rather good for a first-time effort. I hope you all like it too!

imgur.com category @softerword