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Daddy’s cane hurts

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

Pain and Cane

Dressed like an innocent slut taking a caning

Caning Challenge

Caned by Bobbi Starr

Caning my inferior tits for superior White Kings

Painful.

A painful hand caning.

a painful caning.

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A painful caning.

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

MILF Mommy Pain Punishment

Ass Up For a Caning

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Caning FTM Pain gif

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

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

Jessie Cox gets trained to handle the pain

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Salivating Snotty Anguish

A painful caning.

upside down blindfolded caning

Caning the phobia into the hetero twink

This was very painful for Lola.

Caning Play/Pain

Caned Tits and Tears

caning myself for being a desperate whore

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

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

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

Scarlet Faux can orgasm just from having her feet caned

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 😈

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

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No pain, no gain!

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

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

The caning feels so good on my big titties

Next comes the Rattan Cane.

Amelia's Naked Caning

Skylar's Curfew Caning

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Hard and Painful Femdom Caning (sound on)

Holly Michaels gets pilloried, spanked, flogged, whipped, and caned

Hard bare bottom caning

A painful thigh caning by Miss Belle.

A painful thigh caning.

Spanking Saturday 🔥

Tit caning makes me cry out for pain

Caned lying down

Caned on jeans

Caned

I failed my domestic duties today and was punished with 12 cane strokes 😭... Since there is no warm up they are actually really painful! My Owner has set rules and every time I break one, I have to note it down on our "Bad Board".

My [F] "attitude adjustment" caning yesterday. I don't think I'll ever learn!