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Chastity Punishment gifs

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She slid her little clit out of her cage so she could touch herself. How should I

She slid her little clit out of her cage so she could touch herself. How should I punish her? Her smaller cage should get here soon.

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It doesn’t get much more submissive than my man…on the floor, taking my piss.

It doesn’t get much more submissive than my man…on the floor, taking my piss.

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Look what o found on someone’s phone….this was before I put him in permanent

Look what o found on someone’s phone….this was before I put him in permanent lockdown and it would appear he can still get some release….just trying to decide how I should punish him 😈😂

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It gets me so wet when I know he's getting absolutely no pleasure...naughty boys

It gets me so wet when I know he's getting absolutely no pleasure...naughty boys get punished 😈

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Last day of punishment/complete pussy ban...I do love riding the strap on while he

Last day of punishment/complete pussy ban...I do love riding the strap on while he begs me to unlock him .😏

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I only got short clips from today's session with my new spanking machine. Help decide

I only got short clips from today's session with my new spanking machine. Help decide my punishment?

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alright sissies. Tonight’s task. Squirt in your cage. If you have diapers. Over

alright sissies. Tonight’s task. Squirt in your cage. If you have diapers. Over that too. Message me either a vid of you succeeding for more tasks, or failing for punishment

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Miss has been punishing me all day and its exactly what I deserve

Miss has been punishing me all day and its exactly what I deserve

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I know you've been sniffing my panties. Now it's time for your punishment.

I know you've been sniffing my panties. Now it's time for your punishment.

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He's clearly not learnt his lesson from his last punishment. Orgasmed again without

He's clearly not learnt his lesson from his last punishment. Orgasmed again without permission. Three weeks of no pussy at all for him while I fuck my bulls...I'll keep you all updated 😉

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Say ME if you dare to take hard punishment from daddy 😈🤫

Say ME if you dare to take hard punishment from daddy 😈🤫

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Chastity Femdom Punishment Sissy Strap On gif

Chastity Femdom Punishment Sissy Strap On gif

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New to punishing my good boy, what should I do next?

New to punishing my good boy, what should I do next?

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I know I’m gonna get it fit this ? I’ll take my punishment to share to you all,

I know I’m gonna get it fit this ? I’ll take my punishment to share to you all, just couldn’t help myself ?thanks for following?? ?

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Flr at it best :) boys getting punished

Flr at it best :) boys getting punished

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I've been a very bad boy and I need punishment 🤐

I've been a very bad boy and I need punishment 🤐

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from small to smaller to punished

from small to smaller to punished

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She let me out of my cage but punished me for misbehaving 😈

She let me out of my cage but punished me for misbehaving 😈

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When he misbehaves this is his punishment

When he misbehaves this is his punishment

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Comment your loser size to receive a properly punishment for a sissy Beta like you…

Comment your loser size to receive a properly punishment for a sissy Beta like you…

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As per our punishment for my cuck cumming without permission the other day.. I decided

As per our punishment for my cuck cumming without permission the other day.. I decided to tell him I was going to let him out to play with him.. Unfortunately not in the way he thought I meant.. 😈😘 Here's a little preview 😘

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Hubby's locked and ready to break his old record 🤭 are you ready to watch along

Hubby's locked and ready to break his old record 🤭 are you ready to watch along and help me make it as difficult as possible? 🤭😘🔒 Only 85 more days to go 🤣

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Took too long to fulfill a task, Daddy ordered to whip my balls as punishment 😰

Took too long to fulfill a task, Daddy ordered to whip my balls as punishment 😰 kik janisjanis1

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If you don’t wear it I’ll punish you

If you don’t wear it I’ll punish you

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🎮Sophia is my best png girlfriend 🐉⚔️

🎮Sophia is my best png girlfriend 🐉⚔️

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If you cum, you will be punished.

If you cum, you will be punished.

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[domme] if you ask the answer is always no!

[domme] if you ask the answer is always no!

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♥️Red Day♥️

♥️Red Day♥️

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last of punishment today 👀

last of punishment today 👀

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Oops 🤭😈😂 I think I broke the key 😲😲 I guess I don't know my own strength

Oops 🤭😈😂 I think I broke the key 😲😲 I guess I don't know my own strength 🤭😘

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I didn’t expect to squirt like this from just punishing my balls for a little bit,

I didn’t expect to squirt like this from just punishing my balls for a little bit, was so excited to see it 🤭

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Locktober Failure Tax & Tasks NEW CLIP available on LOCKEDinChastity.com

Locktober Failure Tax & Tasks NEW CLIP available on LOCKEDinChastity.com

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Rough Pegging and as a reward... some cane punishment!

Rough Pegging and as a reward... some cane punishment!

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It's only locktober 3rd and he's already misbehaving. I had to spank him to remind

It's only locktober 3rd and he's already misbehaving. I had to spank him to remind him who's in charge. If he doesn't learn his lesson, it's going to be a long month for him.

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chastity femdom mistress punishment slave gif

chastity femdom mistress punishment slave gif

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NNN Day 9 Sissygasm, what should my punishment be? 👉👈

NNN Day 9 Sissygasm, what should my punishment be? 👉👈

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your mommy can punish and humiliate you if you don't behave well... don't make her

your mommy can punish and humiliate you if you don't behave well... don't make her angry! but if you behave well there may be prizes! subscribe for free to my only fans

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Your mistress will give you great recognition if you do your punishment on time.

Your mistress will give you great recognition if you do your punishment on time.

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Sometimes you get punished for being too obedient...

Sometimes you get punished for being too obedient...

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A dildo is a sissy's best friend💕

A dildo is a sissy's best friend💕

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It's all honest. I trade orgasm for orgasm

It's all honest. I trade orgasm for orgasm

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belt to punish sissys, who will be the first?

belt to punish sissys, who will be the first?

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should this be encouraged or punished?

should this be encouraged or punished?

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A little night time spanking before bed. [m] I love watching his poor caged cock

A little night time spanking before bed. [m] I love watching his poor caged cock and balls swing with ever impact. Should I go easy?

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I failed on the last day of NNN 🫣 what should my punishment be?

I failed on the last day of NNN 🫣 what should my punishment be?

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1st cum in 99 days

1st cum in 99 days

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College girl locked up for texting boys without permission

College girl locked up for texting boys without permission

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I worked hard tonight to change my hole.

I worked hard tonight to change my hole.

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Just lock yourself in once and you'll forever be captivated by these unforgettable

Just lock yourself in once and you'll forever be captivated by these unforgettable feelings and sensations!

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My punishment for being knotty

My punishment for being knotty

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Ready to begin 28 days of flat cage punishment, maybe it will be extended even longer...

Ready to begin 28 days of flat cage punishment, maybe it will be extended even longer...

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It's very difficult to hold the camera and record oneself sucking dick, but I figured

It's very difficult to hold the camera and record oneself sucking dick, but I figured you'd appreciate the video regardless 😘

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chastity feminization punishment sissy sissy slut trailer sissycaption gif

chastity feminization punishment sissy sissy slut trailer sissycaption gif

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Should locked sissies be required to punish themselves?

Should locked sissies be required to punish themselves?

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What’s the punishment when you use the toilet without permission? You have to dance

What’s the punishment when you use the toilet without permission? You have to dance and twist and squeeze yourself into your last used diaper while I sip my coffee and watch ☁️

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Do you like a clever keyholder who uses punishment and degradation to keep you at

Do you like a clever keyholder who uses punishment and degradation to keep you at her mercy? Or do you prefer a gentle keyholder who uses to motivation and rewards to control you?

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chastity cuckold femboy german hardcore humiliation piss pissing punishment sissy

chastity cuckold femboy german hardcore humiliation piss pissing punishment sissy bbc-sissy gay-slut sissy-chastity sissy-training trans-sissy-porn gif

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Just the inverted cage in action

Just the inverted cage in action

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Ready to be unlocked

Ready to be unlocked

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Daddy says I’ve been bad and have to be punished 🥺🤭🥰

Daddy says I’ve been bad and have to be punished 🥺🤭🥰

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