Categories

SELECT COUNT(*) FROM gallery WHERE topic_category="SissyChastity"

You find me bent over and dripping in the Walmart bathroom, what's next?

You find me bent over and dripping in the Walmart bathroom, what's next?

That's right bitch you know the routine Mia😈 The moment you get up you do your verifications sissy slave. Soon we'll have you back on your masturbation sessions slave😇 Have to work you back up to that huge toy that you have 😈

That's right bitch you know the routine Mia😈 The moment you get up you do your verifications sissy slave. Soon we'll have you back on your masturbation sessions slave😇 Have to work you back up to that huge toy that you have 😈

I've been naughty this year 🥺

I've been naughty this year 🥺

Im always so happy now that I've accepted chastity as a permanent part of my life

Im always so happy now that I've accepted chastity as a permanent part of my life

Just sent this to my straight friends...feeling kinda nervous 👉👈

Just sent this to my straight friends...feeling kinda nervous 👉👈

add me on my snap ruby.wood23 if you want to be my little sissy in chastity. 20 likes and i post sissy tasks. :***

add me on my snap ruby.wood23 if you want to be my little sissy in chastity. 20 likes and i post sissy tasks. :***

My first Locktober with a keyholder 😄 Day 8... getting desperate for (her) attention 😭

My first Locktober with a keyholder 😄 Day 8... getting desperate for (her) attention 😭

should i participate in locktober?

should i participate in locktober?

Listening to my girlfriend get fucked in the other room again

Listening to my girlfriend get fucked in the other room again

Love how metal feels

Love how metal feels

I downsized

I downsized

Happy Valentines ❤️

Happy Valentines ❤️

All boys do this when they're home alone right? ☺️

All boys do this when they're home alone right? ☺️

Too small for my small cage…

Too small for my small cage…

Locktober fun...

Locktober fun...

Do you think I need a matching pink plug? 🤔

Do you think I need a matching pink plug? 🤔

Back in..pink! With superglued locks

Back in..pink! With superglued locks

love waking up like this 💖

love waking up like this 💖

Who asked for a footjob in chastity?

Who asked for a footjob in chastity?

Do I look good caged ?! 🥰🔐🍆

Do I look good caged ?! 🥰🔐🍆

For the ones that asked, of course my enslave sissy Rose 🌹 is in Chastity all the time 😈 Rose's morning verification.

For the ones that asked, of course my enslave sissy Rose 🌹 is in Chastity all the time 😈 Rose's morning verification.

As so it begins!

As so it begins!

Your male life is completely over now Megan, get used to your new clothing sissy bitch and get that pussy ready for your masturbation today.

Your male life is completely over now Megan, get used to your new clothing sissy bitch and get that pussy ready for your masturbation today.

Nice room, so watcha wanna do now?

Nice room, so watcha wanna do now?

Day #2 locked up by my baby 🥰, Day #9 not cumming 🤫

Day #2 locked up by my baby 🥰, Day #9 not cumming 🤫

Love choking my locked up clitty

Love choking my locked up clitty

I’ve been horny all day 🙈 someone replace my toy, please! 👀

I’ve been horny all day 🙈 someone replace my toy, please! 👀

Locked back up after failing to satisfy my gf. I don’t think I’m ever getting unlocked again.

Locked back up after failing to satisfy my gf. I don’t think I’m ever getting unlocked again.

everything feels better when a cage is involved 💝

everything feels better when a cage is involved 💝

Waiting for my Mastress Add/u/RainSeraph to call so i can ride their dick🙈🥰

Waiting for my Mastress Add/u/RainSeraph to call so i can ride their dick🙈🥰

My permanently locked micro clit turns me into anal public slut🔐👌 I really want to be filled with cum🥰💦

My permanently locked micro clit turns me into anal public slut🔐👌 I really want to be filled with cum🥰💦

Ugggg day 6 please someone fuck the cum out of me

Ugggg day 6 please someone fuck the cum out of me

I Think I Should Stay Locked For The Year 🔒

I Think I Should Stay Locked For The Year 🔒

Something racy for Friday

Something racy for Friday

Take my key and control me daddy

Take my key and control me daddy

My enslaved Ariane's panties verification this morning.

My enslaved Ariane's panties verification this morning.

This is the girl that almost two months of chastity has created…

This is the girl that almost two months of chastity has created…

Caged and cuffed and helpless

Caged and cuffed and helpless

Look… no hands :) seemed like a convenient place to keep a condom just in case… ;)

Look… no hands :) seemed like a convenient place to keep a condom just in case… ;)

I wish someone would just do me already...💋

I wish someone would just do me already...💋

I'm wondering what would some of you wonderful people here on Reddit do to my sweet kitty Megan's hole🤔 do you stuff it or would you lick it 😛

I'm wondering what would some of you wonderful people here on Reddit do to my sweet kitty Megan's hole🤔 do you stuff it or would you lick it 😛

My first post on here🥰

My first post on here🥰

Totally your fantasy

Totally your fantasy

Dressed to suck seed

Dressed to suck seed

A sissy’s POV

A sissy’s POV

Who's ready for the new year

Who's ready for the new year

How do you think my chastity training is going? 🥺😇🔐

How do you think my chastity training is going? 🥺😇🔐

My enslaved sissy Ariane's check in this morning.

My enslaved sissy Ariane's check in this morning.

im thankful i realized im a cum slut 🥴

im thankful i realized im a cum slut 🥴

sissy slut all locked up

sissy slut all locked up

Keep my locked up clit in my panties like a good girl

Keep my locked up clit in my panties like a good girl

💋 someone tell me i'm cute 🍑

💋 someone tell me i'm cute 🍑

Still locked for NOvember :(

Still locked for NOvember :(

A little coy, but I hope you enjoy 💋

A little coy, but I hope you enjoy 💋

Showered and shaved and back in chastity

Showered and shaved and back in chastity

Caged and plugged like it should be

Caged and plugged like it should be

Yay i can post on here now.

Yay i can post on here now.

I never really anticipated that this was how I'd be

I never really anticipated that this was how I'd be "masturbating", but, well, here we are!

My little locked clit is almost invisible under this tight suit🔐🖤

My little locked clit is almost invisible under this tight suit🔐🖤

Locktober Day 17 freshly shaved and clean

Locktober Day 17 freshly shaved and clean

My sweet Rose's🌹 clit feeling aroused first thing in the morning😈 plugging up that bussy seems to help 😇

My sweet Rose's🌹 clit feeling aroused first thing in the morning😈 plugging up that bussy seems to help 😇

What do you say to layered nylons?

What do you say to layered nylons?

My enslaved sissy Ariane's morning verification.

My enslaved sissy Ariane's morning verification.

My enslaved sissy Lucy's verification from work 😇

My enslaved sissy Lucy's verification from work 😇

I hope you don’t mind that I wore my chastity cage on our date…

I hope you don’t mind that I wore my chastity cage on our date…

Need someone to take the key

Need someone to take the key

All locked away in garter belt and stockings at work. Happy Locktober ♥️

All locked away in garter belt and stockings at work. Happy Locktober ♥️

I love love love being caged.

I love love love being caged.

If a rock hard jock were to gawk at or mock my cock lock, I'd be shocked.

If a rock hard jock were to gawk at or mock my cock lock, I'd be shocked.

Day 1 of my chastity journey 😊

Day 1 of my chastity journey 😊

reminder that i’m not a real man

reminder that i’m not a real man

Keep my clit permanently locked🔐👌🏻 To be sluty and hot🍑🥰

Keep my clit permanently locked🔐👌🏻 To be sluty and hot🍑🥰

Anyone want to play in Ohio?

Anyone want to play in Ohio?

:3 playing games and noones knows im locked in chastity 😍

:3 playing games and noones knows im locked in chastity 😍

Would you kiss my body?

Would you kiss my body?

Lock is bigger than my clitty

Lock is bigger than my clitty

Uff, it's thight

Uff, it's thight

No touching 😳

No touching 😳

How long should I leave it on for this time? 💕

How long should I leave it on for this time? 💕

It's official this bitch has given up her rights and privacy to be one of my enslaved sex objects 😈 welcome to the harem my sissy enslaved Lucy 😇

It's official this bitch has given up her rights and privacy to be one of my enslaved sex objects 😈 welcome to the harem my sissy enslaved Lucy 😇

My stockings have torn, who would buy me a new pair?? 🥺❤️

My stockings have torn, who would buy me a new pair?? 🥺❤️

tight fit 😟

tight fit 😟

Some asked me for a before and after I became a Sissy. Am I turning into a pretty girl?

Some asked me for a before and after I became a Sissy. Am I turning into a pretty girl?

Be limp

Who wants to come breed me 😝

Who wants to come breed me 😝

Hello 👋🏻😊 This is my first post on here

Hello 👋🏻😊 This is my first post on here

Day 18 🥵

Day 18 🥵

Locktober Day 9: Who wants to see what's under my skirt?

Locktober Day 9: Who wants to see what's under my skirt?

Cute little pink cage and thicc thighs in white stockings

Cute little pink cage and thicc thighs in white stockings

hey 💕

The things chastity makes you do. Presenting my vitiligo pussy

The things chastity makes you do. Presenting my vitiligo pussy

Locking up helps me focus on my work

Locking up helps me focus on my work

Woke up straining

Woke up straining

Locked in for 17 more days! 💖

Locked in for 17 more days! 💖

Think I’m Ready for a smaller cage

Think I’m Ready for a smaller cage

Cum give me your stuffing 🦃

Cum give me your stuffing 🦃

I don't see masculinity here... 😬

I don't see masculinity here... 😬

My enslaved German Sophia morning verification 😇

My enslaved German Sophia morning verification 😇

Love this cute new 🐷 🔐

Love this cute new 🐷 🔐