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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

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

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.

Caning Pain Masochism gif

A painful caning.

Caning Pain Schoolgirl Spanking gif

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

Caning FTM Pain gif

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

Jessie Cox gets trained to handle the pain

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

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.

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

Hard and Painful Femdom Caning (sound on)

Dollified and used as a pain toy.

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

Wiggle your ass when you're ready for your caning

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!

Caning the underboob. [OC]

Happy Spanksgiving! Grateful for the pain I got

Paddle slaps on already caned and paddled pussy

Master likes to inflict pain to his submissive

Pain and pleasure