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Painful Chastity

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His pain is my pleasure ;) (HJ33-9)

His pain is my pleasure ;) (HJ33-9)

New anal only chastity video! EvilKitties

New anal only chastity video! EvilKitties

Veronica | I Give Him a Painful Orgasm in His Chastity Cage with My Hitachi

Veronica | I Give Him a Painful Orgasm in His Chastity Cage with My Hitachi

Painful Cumming in Chastity

Painful Cumming in Chastity

Bound with EStim urethral plug, giving him some pained release.

Bound with EStim urethral plug, giving him some pained release.

I get to fuck your wife while your little dick is caged. Good luck with that painful boner.

I get to fuck your wife while your little dick is caged. Good luck with that painful

Dominant Wife Locks Slave Husband Up In Chastity

Dominant Wife Locks Slave Husband Up In Chastity

Pain is pleasure

Pain is pleasure

Someone used to occasionally play with my sack during cuddling. It would throb, try to get hard, I would squirm, complain or try to hump hand just to get a very painful balls slap for being too ..frisky pet, and then he would continue.

Someone used to occasionally play with my sack during cuddling. It would throb, try

This morning was painful ?

This morning was painful ?

🦋So tight it hurts…what I call a “beautiful kind of pain”🦋

🦋So tight it hurts…what I call a “beautiful kind of pain”🦋

If you managed not to cum, you would've get two weeks of freedom from chastity!

If you managed not to cum, you would've get two weeks of freedom from chastity!

New girlfriend got a bit carried away while filming… (sound on to hear how much fun she’s having and how much pain I’m in)

New girlfriend got a bit carried away while filming… (sound on to hear how much

Small key hanging betwen my breast... All I need to control you cock, cum and cause you pain

Small key hanging betwen my breast... All I need to control you cock, cum and cause

Ride through the pain ??

Ride through the pain ??

He Thinks His Blue Balls are Going to PoP in Ball Crusher! But I know They Can Take More Pain for Mistress Loow. 😈

He Thinks His Blue Balls are Going to PoP in Ball Crusher! But I know They Can Take

And I hope it's painful 😈

And I hope it's painful 😈

A little pain with our pleasure this evening. [m]

A little pain with our pleasure this evening. [m]

This will be serious, painful and very educational!

This will be serious, painful and very educational!

Most underestimate the level of pain a hard cock in a spiked cage can produce!

Most underestimate the level of pain a hard cock in a spiked cage can produce!

Squirming and moaning in pain while slapping my full balls.

Squirming and moaning in pain while slapping my full balls.

The Doxy is the most pleasurable pain, for a slut in chastity ? [domme]

The Doxy is the most pleasurable pain, for a slut in chastity ? [domme]

A little chastity acceptance training… If he asks to be let out he pays a painful price 😈

A little chastity acceptance training… If he asks to be let out he pays a painful

Starting our adventure down cbt, remind him I own his pain and pleasure

Starting our adventure down cbt, remind him I own his pain and pleasure

Flattening his Blue Swollen Balls in Chastity Cage with all my weight between Seat While my Parents are Home… I hope they did not Hear us since he Did Not Shut Up about his Stupid Painful Balls.

Flattening his Blue Swollen Balls in Chastity Cage with all my weight between Seat

alls in Metal Crusher While he Stays in Micro Chastity Cage for our Pleasure!

alls in Metal Crusher While he Stays in Micro Chastity Cage for our Pleasure!

There should always be a little pain before the pleasure 😈😏

There should always be a little pain before the pleasure 😈😏

Throwback to when pain and pleasure were the same

Throwback to when pain and pleasure were the same

Its time for a game of pleasure or pain. Roll an even number and get pleasure. Odd equals pain. Full 12 minute game on OF!

Its time for a game of pleasure or pain. Roll an even number and get pleasure. Odd

Pain Slut said he wanted to use the Vibrator on his Small Chastity Cage because he has Bad Blue Balls so I Crushed them with All my Weight in between the Toilet Seat and allowed him to use the Vibrator. 😈 I am so Nice to my Pain Slut. 😇

Pain Slut said he wanted to use the Vibrator on his Small Chastity Cage because he

Day 5 of Locktober! 🔒 Using my New Strong Ball Crusher on Pain Slut’s Swollen Blue Balls!

Day 5 of Locktober! 🔒 Using my New Strong Ball Crusher on Pain Slut’s Swollen

I allowed him to Worship my ass While he is Locked in Small Chastity Cage but I want his balls in between the Toilet Seat with all my weight as I smother him in my Ass! 🍑🚽💦😈

I allowed him to Worship my ass While he is Locked in Small Chastity Cage but I want

You think you're in pain now? Just you wait..

You think you're in pain now? Just you wait..

Your pain is my pleasure

Your pain is my pleasure

Sissy in small chastity

Sissy in small chastity

I'm not sure what was more painful. The ruined handjob or the overstimulation afterwards. This was after a month of chastity 😭😭

I'm not sure what was more painful. The ruined handjob or the overstimulation afterwards.

I love watching it struggle to escape, trying to squeeze out of every opening (Locktober Day 10)

I love watching it struggle to escape, trying to squeeze out of every opening (Locktober

No release for you, only a painful tease...

No release for you, only a painful tease...

these were painful

these were painful

It doesn't always have to be a cage

It doesn't always have to be a cage

You have chosen a sadist as a key holder, so I guess you have to go through with it!

You have chosen a sadist as a key holder, so I guess you have to go through with

You better make an effort, because every second more means more pain!

You better make an effort, because every second more means more pain!

chastity cheating edging femdom intense pain teasing clip

chastity cheating edging femdom intense pain teasing clip

I left town for a few days and came back to this 👿. His balls are in for a world of pain 👊 sorry hubby. You brought this on yourself 😜

I left town for a few days and came back to this 👿. His balls are in for a world

Pain is always a pleasure to give- and one my sub will eager accept if I'm sitting on their face!

Pain is always a pleasure to give- and one my sub will eager accept if I'm sitting

She gives you pleasure and pain!

She gives you pleasure and pain!

I have been getting more and more desperate after a while in chastity, so when my hole isn't ready, I start harshly kneading my balls, it's painful, but it does quench the thirst, and it's the closest I can get to touching my clit

I have been getting more and more desperate after a while in chastity, so when my

Cute skinny tranny locked in chastity gets her asshole torn apart with massive cocks.

Cute skinny tranny locked in chastity gets her asshole torn apart with massive cocks.

[💜OF] i used to feel pain but now i just feel pleasure!

[💜OF] i used to feel pain but now i just feel pleasure!

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?

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

Day 17 of NNN, challenge 16 accepted 😊Always feel good to slap my useless balls with my hands , it’s a different pain and pleasure than slapping them with a bbc dildo 😝

Day 17 of NNN, challenge 16 accepted 😊Always feel good to slap my useless balls

Bondage, Chastity, Punishment and beautiful clothed Mistress

Bondage, Chastity, Punishment and beautiful clothed Mistress

I don't care if it's painful, I'm still going to tease you!

I don't care if it's painful, I'm still going to tease you!

Pushing the 22 inches deep inside my tight ass. It was oddly tight, filling, painful and pleasurable all in one. Full video on my OF page (PPV with currently free subscription)

Pushing the 22 inches deep inside my tight ass. It was oddly tight, filling, painful

My GF said she loves hearing me moan in pain while trying to escape the chains I'm locked in. She told me the sound of me suffering turns her on... [CD]

My GF said she loves hearing me moan in pain while trying to escape the chains I'm

All locked and denied..would you give my sensitive nipples teasing pleasure or clamping pain

All locked and denied..would you give my sensitive nipples teasing pleasure or clamping

I don't know what made me moan more. When my GF teased me with her hands or the pain of the super tight armbinder

I don't know what made me moan more. When my GF teased me with her hands or the pain

My Small Cock Coming Out Of A Chastity

My Small Cock Coming Out Of A Chastity

[domme] In the depths of pain, I sculpt your submission, molding you into my masterpiece of desire, forever marked by the exquisite torment of my dominance. 🔥

[domme] In the depths of pain, I sculpt your submission, molding you into my masterpiece

A quick lesson in who's in charge!

A quick lesson in who's in charge!

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