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Painful Caning gifs

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cane gif

cane gif

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Daddy’s cane hurts

Daddy’s cane hurts

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Spanked Girl

Spanked Girl

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Took some suggestions from other users & we and got a paddle...cane me any

Took some suggestions from other users & we and got a paddle...cane me any day because I found this more painful 🙈 however we enjoyed it

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[Paid content] Masochistic Mindfuck: Hypnotised Sub Orgasming from Pain

[Paid content] Masochistic Mindfuck: Hypnotised Sub Orgasming from Pain

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Pain and Cane

Pain and Cane

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Dressed like an innocent slut taking a caning

Dressed like an innocent slut taking a caning

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More caning from Bobbi Starr

More caning from Bobbi Starr

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Caning Challenge

Caning Challenge

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Caned by Bobbi Starr

Caned by Bobbi Starr

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Caning my inferior tits for superior White Kings

Caning my inferior tits for superior White Kings

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Painful.

Painful.

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A painful hand caning.

A painful hand caning.

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a painful caning.

a painful caning.

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Caning Pain Masochism gif

Caning Pain Masochism gif

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A painful caning.

A painful caning.

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Caning Pain Schoolgirl Spanking gif

Caning Pain Schoolgirl Spanking gif

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Sir likes to use my latex thong to whip my asshole before inserting my anal hook

Sir likes to use my latex thong to whip my asshole before inserting my anal hook for maximum pain. (Sound on)

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MILF Mommy Pain Punishment

MILF Mommy Pain Punishment

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Ass Up For a Caning

Ass Up For a Caning

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Daddy drew blood with this cane bundle on my ass 🥵 [F] [NB]

Daddy drew blood with this cane bundle on my ass 🥵 [F] [NB]

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Caning FTM Pain gif

Caning FTM Pain gif

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Simone Sonay gets caned for coming off of his cock before he said she could

Simone Sonay gets caned for coming off of his cock before he said she could

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Slave took 20 hard strokes on her ass for another girl, to allow her to have orgasm.

Slave took 20 hard strokes on her ass for another girl, to allow her to have orgasm.

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My pussy was so sore after this session with Mistress Noir... I loved it!

My pussy was so sore after this session with Mistress Noir... I loved it!

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She cries and she begs but her cunt gets sloppy wet

She cries and she begs but her cunt gets sloppy wet

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[f] I'm just a bad girl being forced to squirt while getting caned!

[f] I'm just a bad girl being forced to squirt while getting caned!

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You better get up on those toes, Bobbi...

You better get up on those toes, Bobbi...

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Calico gets her ass striped red by Maitresse Madeline

Calico gets her ass striped red by Maitresse Madeline

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Jessie Cox gets trained to handle the pain

Jessie Cox gets trained to handle the pain

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Salivating Snotty Anguish

Salivating Snotty Anguish

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just where i belong—locked up in a strait jacket with my soles exposed for tickles

just where i belong—locked up in a strait jacket with my soles exposed for tickles and pain for almost an hour ❣️ ft. fettish vids

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Gauging my pain tolerance 1-10 🥵 don't miss the full video tomorrow!

Gauging my pain tolerance 1-10 🥵 don't miss the full video tomorrow!

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A painful caning.

A painful caning.

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Pleasures and Pain

Pleasures and Pain

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upside down blindfolded caning

upside down blindfolded caning

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Caning the phobia into the hetero twink

Caning the phobia into the hetero twink

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This was very painful for Lola.

This was very painful for Lola.

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Caning Play/Pain

Caning Play/Pain

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Caned Tits and Tears

Caned Tits and Tears

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Rebel Rhyder - Caning

Rebel Rhyder - Caning

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When Indians Go Truly Wild! [M][F]

When Indians Go Truly Wild! [M][F]

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caning myself for being a desperate whore

caning myself for being a desperate whore

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Hypnotized my slave to only feel pleasure from pain - and make her cum that way

Hypnotized my slave to only feel pleasure from pain - and make her cum that way

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Extra Strenght Canes - Apply liberally as needed to the the offending young ladies

Extra Strenght Canes - Apply liberally as needed to the the offending young ladies bottom for acute misbehavior

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Tired of your slut's same ugly face? Make it interesting!

Tired of your slut's same ugly face? Make it interesting!

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More ice predicaments for Calico

More ice predicaments for Calico

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Scarlet Faux can orgasm just from having her feet caned

Scarlet Faux can orgasm just from having her feet caned

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I got in trouble. I ate more Halloween chocolate than Sir said I could have, so I

I got in trouble. I ate more Halloween chocolate than Sir said I could have, so I got punished with the cane and with a butt plug in 😤. It was worth it though 😈

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We did a scene with the worst cane ever and i had an orgasm during caning.

We did a scene with the worst cane ever and i had an orgasm during caning.

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No pain, no gain!

No pain, no gain!

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Final challenge: A paddle for Sugar and the cane for Lou 😊🤤 Who might have

Final challenge: A paddle for Sugar and the cane for Lou 😊🤤 Who might have won?

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Playing with my nipples before I get my big tits caned 🔥

Playing with my nipples before I get my big tits caned 🔥

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The caning feels so good on my big titties

The caning feels so good on my big titties

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Next comes the Rattan Cane.

Next comes the Rattan Cane.

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Amelia's Naked Caning

Amelia's Naked Caning

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Skylar's Curfew Caning

Skylar's Curfew Caning

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I bring the pain like!! [M] [OC]

I bring the pain like!! [M] [OC]

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Hard and Painful Femdom Caning (sound on)

Hard and Painful Femdom Caning (sound on)

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(Nb) Caning my naughty clit, how many swats would you give it?

(Nb) Caning my naughty clit, how many swats would you give it?

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