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64% HD 1:01 / 15:23

Sissy Caned by Two Cruel Mistresses

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Your Love of Pain Gets You the Cane

69% 1:01 / 10:07

Your Love of Pain Gets You the Cane

FapHouse prije 10 mjeseci

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Premium HD 5:35

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Sissy Caned by Two Cruel Mistresses

Sissy Caned by Two Cruel Mistresses

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Mistressae Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

61% HD 1:01 / 31:19

Mistressae Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

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caned and wanked

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Mistressae Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

55% HD 0:39 / 31:19

Mistressae Sessions with Princess Latex Rubber Doll: Impact & Spit Roast Training

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Very hard caning

Very hard caning

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The English education of a cuckold

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Khloe's Toy

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I punish my husband because he doesn't lick his

I punish my husband because he doesn't lick his

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Your Love of Pain Gets You the Cane

66% 0:39 / 10:07

Your Love of Pain Gets You the Cane

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”How to Train your Slut Part I”

”How to Train your Slut Part I”

TransHero prije 2 tjedana

Naughty Fashion Show - compilation of stylings with hard caning and vast cumshot

Naughty Fashion Show - compilation of stylings with hard caning and vast cumshot

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65% HD 0:10 / 4:44

sissy maid caned in wet knickers

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Sissy punished 50 smacks with the cane.

Sissy punished 50 smacks with the cane.

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Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

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crossdresser spanking

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Spanking with carpet beater and cane

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hot latina tranny enjoys cock🌭 in hallway — squirting freely for all to see

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Caned by Princes Ammy 7

Caned by Princes Ammy 7

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TS driving student smashes stunning slut in the classroom

TS driving student smashes stunning slut in the classroom

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Mistress Baton’s Sissy Finishing School guest starring Mistress Vixen: Sissy Caning & BJ Training

HD 0:10 / 24:01

Mistress Baton’s Sissy Finishing School guest starring Mistress Vixen: Sissy Caning & BJ Training

LoyalFans prije 3 tjedana

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63% HD 0:10 / 9:05

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HD 0:10 / 10:35

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A Disgrace to Our Town Part 1

60% 1:01 / 21:04

A Disgrace to Our Town Part 1

FapHouse prije 9 mjeseci

You can break my ass #Kodabratz

You can break my ass #Kodabratz

xHamster prije 3 godina

The Smut Peddlers: Part Two Helena Locke and Natalie Mars

Premium 65% HD 37:13

The Smut Peddlers: Part Two Helena Locke and Natalie Mars

KinkTrans prije 5 godina

French Aged S&M 1 of three

French Aged S&M 1 of three

MatureTubeHere prije 2 godina

Trans woman gets her twat and butt destroyed after some kinky play - DemonicSensuality part 4

Trans woman gets her twat and butt destroyed after some kinky play - DemonicSensuality part 4

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Trans slave Luzi punished and fucked

HD 0:10 / 14:09

Trans slave Luzi punished and fucked

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The Masculines Moneyless My Culo and Pushed Caned Juice Inwards Me - Nicolly Summers ADDITIONAL GIGS

The Masculines Moneyless My Culo and Pushed Caned Juice Inwards Me - Nicolly Summers ADDITIONAL GIGS

KeekAss prije 11 mjeseci

Mistresse Aprils black female serf gets punished for masturbating

Mistresse Aprils black female serf gets punished for masturbating

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His wife enjoys his punishment for not licking her

His wife enjoys his punishment for not licking her

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CD Sissy ass caned hard

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French Aged S&M two of three

French Aged S&M two of three

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Booted Sissy In Need For Cane & Dicks

Booted Sissy In Need For Cane & Dicks

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Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

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Severe Caned In A Pleated Satin Gown

Severe Caned In A Pleated Satin Gown

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MTF Trans Cutie Deepthroats, Gets Her Titties Caned, and Gets Overspread in Cum

MTF Trans Cutie Deepthroats, Gets Her Titties Caned, and Gets Overspread in Cum

Amateur8 prije 2 mjeseci

Cane have fun

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Bent Over

HD 0:10 / 21:27

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Bondage Spitroast Caning Pt2

Bondage Spitroast Caning Pt2

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Thrilling moment from "Booted Sissy In Need For Cane & Dicks"

Thrilling moment from "Booted Sissy In Need For Cane & Dicks"

xHamster prije 4 mjeseci

Kitsy paddled & caned a severe spanking in strappado with anal hook

Kitsy paddled & caned a severe spanking in strappado with anal hook

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Caning Sweetie

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TS dominant canes fastened dude

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KitsyMe0w. Ten minute fuck. (Anal sex)

KitsyMe0w. Ten minute fuck. (Anal sex)

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Latex Maid Lisa Gets a Good Spanking and Flogging From Tgirl Mistress Lucy

HD 1:01 / 32:14

Latex Maid Lisa Gets a Good Spanking and Flogging From Tgirl Mistress Lucy

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300 + 1

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”Asian Transgender canes & fucks bound man”

”Asian Transgender canes & fucks bound man”

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Flagellating my PHAT Clittie - Cunt Absorption + Using a Flog on my turgid FAT Clitoris

Flagellating my PHAT Clittie - Cunt Absorption + Using a Flog on my turgid FAT Clitoris

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julie caned then fucked by Master D

julie caned then fucked by Master D

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Twink Sub Whipped By Brazilian Shemale Transwoman Domme Multiple Whips and Caning - Michelly Ximenez

Twink Sub Whipped By Brazilian Shemale Transwoman Domme Multiple Whips and Caning - Michelly Ximenez

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Plugged & Spanked Sissy Bride - ready for use

Plugged & Spanked Sissy Bride - ready for use

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TS-Kristy Punished and Helpless in Pillory as Dominatrix Delivers Relentless Whipping and Spanking for Disobedience (HD)

HD 0:30 / 23:58

TS-Kristy Punished and Helpless in Pillory as Dominatrix Delivers Relentless Whipping and Spanking for Disobedience (HD)

Clips4sale prije 4 mjeseci

Freak of Nature Self Cuntspank

Freak of Nature Self Cuntspank

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Trans woman gets her cunt and butt destroyed after some kinky play - DemonicSensuality part 4

Trans woman gets her cunt and butt destroyed after some kinky play - DemonicSensuality part 4

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Sissy Slut's First Impact Play

65% HD 0:21 / 5:00

Sissy Slut's First Impact Play

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The punishment of Louisa Part 7 of 8

65% 0:30 / 6:30

The punishment of Louisa Part 7 of 8

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The punishment of Louisa Part 8 of 8 Final clip in this set

66% 0:30 / 6:50

The punishment of Louisa Part 8 of 8 Final clip in this set

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Caned And Fucked Double Domination

Caned And Fucked Double Domination

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LADY SCARLET - OUR PUPPY - IL NOSTRO CANE

HD 0:10 / 10:30

LADY SCARLET - OUR PUPPY - IL NOSTRO CANE

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The Contract Fucker Part 2 (WMV HD)

The Contract Fucker Part 2 (WMV HD)

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Raphaella Ferrari's enormous And thick ramrod Comes After The Caning

Raphaella Ferrari's enormous And thick ramrod Comes After The Caning

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77% 0:57 / 16:08

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TS Kitten Gal Pixi Lust dominated & fucked by Daddy Draven Navarro in a hardcore BDSM scene

TS Kitten Gal Pixi Lust dominated & fucked by Daddy Draven Navarro in a hardcore BDSM scene

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70% 0:30 / 11:15

24 strokes for Jennifer plus 12 bonus whacks

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AfterSchool Tag - Episode 1 (teaser)

AfterSchool Tag - Episode 1 (teaser)

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CLEANING MISTRESS'S FRIENDS COCK

62% 4K 1:00 / 40:19

CLEANING MISTRESS'S FRIENDS COCK

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73% HD 0:55 / 20:47

Tight Breast Bind Exposed Ass Whipped and Plugged Femdom

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71% 1:00 / 11:25

The Sixth Former's Bargain

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The punishment of Louisa Part 6 of 8

57% 0:30 / 5:00

The punishment of Louisa Part 6 of 8

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69% 4K 0:53 / 20:39

Bought & Broken In (1080 HD)

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A caning from Lady Krampus

A caning from Lady Krampus

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Severe Punishment for Dirty Sissy Slut by Harsh Mistress Part 2

Severe Punishment for Dirty Sissy Slut by Harsh Mistress Part 2

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Dark Skinned Shemale Gets Caned And Cuntsucked In The Dungeon

Dark Skinned Shemale Gets Caned And Cuntsucked In The Dungeon

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Old Mature teen girl and old boyfriend have hot sex with Oma Hunter

Old Mature teen girl and old boyfriend have hot sex with Oma Hunter

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66% 0:10 / 19:38

Sissy Maid's caning punishment WL1718

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Sharp nipples stretch eagerly as the tranny ishornyedly fucked by her boyfriend′s ass🍑

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77% 0:30 / 11:34

Truant Jenny gets caned

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57% 0:30 / 14:48

TWO DOMMES USING HIM (GER)

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HD 0:18 / 11:09

Birthday Bi Party - Part Two - Full - MP4 (HD)

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Birthday Bi Party - Part Two - 1 - MP4

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Dominatrix caning useless slave

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Discipline Day For Joanne 1 The Pre Caning Warm Up

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T-Models cane and shag

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Michelly Ximenez In Twink Sub Whipped By Brazilian Shemale Transwoman Domme Multiple Whips & Caning

Michelly Ximenez In Twink Sub Whipped By Brazilian Shemale Transwoman Domme Multiple Whips & Caning

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Dominatrix caning useless slave

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Towheaded Whipped

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Beauty Slaves Dominated by a Heartless Tranny

Beauty Slaves Dominated by a Heartless Tranny

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Wild mega-bitch Madeline gets hard-core tantalized by her Sir

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This ladyboy breezy Madeline is vulnerable as she gets stiff penalty from her tormentor

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Double Domme: A Lesson in Sissydom & Spanks by Miss Jenn and Mistress Brigitte [MP4](HD)

64% HD 0:11 / 8:47

Double Domme: A Lesson in Sissydom & Spanks by Miss Jenn and Mistress Brigitte [MP4](HD)

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He Cane Prepare Ready to Devore Me

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JockPussy - Luke Hudson & super tasty Luke pussy fucking

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Towheaded Canes 31

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JockPussy: Sweet Luke pussy fuck caning

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