Punishment Videos (40,830)

Catheterized Chastity Slave, Become Obligatory a Sissy

55% HD 0:39 / 18:53

Catheterized Chastity Slave, Become Obligatory a Sissy

FapHouse 3 months ago

Futa Anna Punishes the Submissive Burglar in Her House

Futa Anna Punishes the Submissive Burglar in Her House

3DPornDude 3 weeks ago

Dom Fucks and Spank Delia Delions

66% HD 1:01 / 33:03

Dom Fucks and Spank Delia Delions

FapHouse 2 years ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

Dom Fucks and Spank Delia Delions

57% HD 0:39 / 33:03

Dom Fucks and Spank Delia Delions

FapHouse 2 years ago

Roommate Feminized and Fucked for Punishment

Roommate Feminized and Fucked for Punishment

xHamster 3 months ago

I Need to Be Punished

I Need to Be Punished

FapHouse 8 months ago

Latex Dom Stretches T-boy

HD 1:01 / 26:28

Latex Dom Stretches T-boy

FapHouse 1 month ago

Stepmother Teaches Her Transgender Stepdaughter How to Perform Rituals to Bring a Slave to Orgasm

Stepmother Teaches Her Transgender Stepdaughter How to Perform Rituals to Bring a Slave to Orgasm

FapHouse 1 week ago

Damazonia & Rachel Rampage train their sluts to be Orgy party favors

72% HD 0:10 / 26:24

Damazonia & Rachel Rampage train their sluts to be Orgy party favors

LoyalFans 1 year ago

”Black tbabe step mom rimmed & banged hard by Nick”

”Black tbabe step mom rimmed & banged hard by Nick”

4Wank 2 years ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Young sissy edges and cums while riding huge dildo

Young sissy edges and cums while riding huge dildo

Tranny.one 4 years ago

Trans Babysitter Gets taught a lesson by HOT milf

Trans Babysitter Gets taught a lesson by HOT milf

xHamster 4 years ago

Part 3:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

Part 3:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

xHamster 6 months ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

59% 1:01 / 21:31

Shemale Domination - 15 - Isa Laurens & Rick Bitch

FapHouse 3 months ago

Mrs Samantha outdoor Spanking Marina

Mrs Samantha outdoor Spanking Marina

Tranny.one 4 years ago

Tranny fucks male sub in pink dungeon

Tranny fucks male sub in pink dungeon

Analdin 2 weeks ago

Trans hottie Sunshyne Monroe gets huge cock in her hot trans ass

Trans hottie Sunshyne Monroe gets huge cock in her hot trans ass

xHamster 1 month ago

Latex wearing transgender babe tortures and fucks a helpless slave without a condom

Latex wearing transgender babe tortures and fucks a helpless slave without a condom

Tranny.one 4 years ago

Sissy Slut Swallows Sissygasm- CEI JOI Cum Eating Instructions by Goddess Nikki Kit

Sissy Slut Swallows Sissygasm- CEI JOI Cum Eating Instructions by Goddess Nikki Kit

IWantClips 1 year ago

Gay bottoms deepthroat then get their asses wrecked hard

Gay bottoms deepthroat then get their asses wrecked hard

analpornvids 3 weeks ago

Archie Blossom Private Show

55% HD 2:00 / 16:54

Archie Blossom Private Show

Flirt4Free 1 month ago

This cute asian ladyboy needs a real hard punishement

This cute asian ladyboy needs a real hard punishement

Sheshaft 5 years ago

Verticalargument4tight Dress

44% 0:39 / 1:58

Verticalargument4tight Dress

FapHouse 1 month ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 3 months ago

Trans Beauty Worships His Trans Dick Previous to That guy Wrecks Her Butt

Trans Beauty Worships His Trans Dick Previous to That guy Wrecks Her Butt

FreePorn8 5 months ago

”Shemale Kate Zoha punishes Korra Del Rio with deep rough fucking”

”Shemale Kate Zoha punishes Korra Del Rio with deep rough fucking”

4Wank 11 months ago

Towheaded Whipped

Towheaded Whipped

TrannyGem 5 years ago

Dustin & Angel & Bayron Private Show

57% HD 2:00 / 4:45

Dustin & Angel & Bayron Private Show

Flirt4Free 2 years ago

Esa Tight Dress

Esa Tight Dress

xHamster 1 month ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 6 days ago

”Shemale Kate Zoha punishes Korra Del Rio with deep rough fucking”

”Shemale Kate Zoha punishes Korra Del Rio with deep rough fucking”

Trashreality 10 months ago

$Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen$ 63% HD 2:00 / 27:28

Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen

Flirt4Free 9 months ago

I can't stop thinking about my best friend's relationship with me

I can't stop thinking about my best friend's relationship with me

xHamster 4 months ago

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Tortured Breasts

Tortured Breasts

xHamster 10 years ago

Patric & Alexander & Lian Private Show

53% HD 2:00 / 1:09:57

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Hot shemale professor gives the naughty guy a punishment he will never forget

Hot shemale professor gives the naughty guy a punishment he will never forget

Tranny.one 4 years ago

a lot of punishment of ur fucking cock

a lot of punishment of ur fucking cock

xHamster 1 month ago

Simon & Juseph & Alejandro Private Show

58% HD 2:00 / 1:02:40

Simon & Juseph & Alejandro Private Show

Flirt4Free 2 years ago

flawless Sissy Homo Penalized By BIG BLACK COCK Interracia

flawless Sissy Homo Penalized By BIG BLACK COCK Interracia

TrannyGem 6 years ago

”Fucked Behind Bars”

”Fucked Behind Bars”

Rainblow 1 year ago

Sophia Loreen Party on Sep 14, 2025 - Part 2

4K 2:00 / 18:15

Sophia Loreen Party on Sep 14, 2025 - Part 2

Flirt4Free 7 months ago

Criss & Angeel Private Show

Criss & Angeel Private Show

Flirt4Free 3 years ago

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

TrannyGem 4 years ago

School teenie Practices Painfull Sensation

School teenie Practices Painfull Sensation

GayDudesFucking 1 year ago

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

60% HD 0:39 / 13:12

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

FapHouse 3 months ago

Master Collins Private Show

HD 2:00 / 1:04:18

Master Collins Private Show

Flirt4Free 8 months ago

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

xHamster 1 year ago

Sophia Loreen Party on May 9, 2026 - Part 3

HD 2:00 / 31:50

Sophia Loreen Party on May 9, 2026 - Part 3

Flirt4Free 1 day ago

”Shemale Kate Zoha punishes Korra Del Rio with deep rough fucking”

”Shemale Kate Zoha punishes Korra Del Rio with deep rough fucking”

ThePornstar 1 year ago

Step Mom Punishment Her Son With Bondage Sex - Uncensored Hentai

Step Mom Punishment Her Son With Bondage Sex - Uncensored Hentai

HentaiGem 2 years ago

Blazing Hot Domination by The Fire FULL video from

Blazing Hot Domination by The Fire FULL video from

xHamster 1 year ago

Threesome with bella

Threesome with bella

Tranny.one 4 years ago

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

xHamster 1 year ago

Wild Sabrina Private Show

60% HD 2:00 / 5:31

Wild Sabrina Private Show

Flirt4Free 4 years ago

Dani Saenz Private Show

51% HD 2:00 / 33:18

Dani Saenz Private Show

Flirt4Free 4 years ago

Master & Ithan & Aleex Private Show

54% HD 2:00 / 38:32

Master & Ithan & Aleex Private Show

Flirt4Free 10 months ago

Dominatrix caning useless slave

Dominatrix caning useless slave

Tranny.one 4 years ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 8 months ago

Latex TS Clone Anal Punishment BDSM

Latex TS Clone Anal Punishment BDSM

TrannyGem 4 months ago

Owen & Ronaldo & Patric Private Show

49% HD 2:00 / 14:02

Owen & Ronaldo & Patric Private Show

Flirt4Free 3 years ago

Orianna Dunn Private Show

55% HD 2:00 / 12:27

Orianna Dunn Private Show

Flirt4Free 2 years ago

TS Larissa seduces the teacher and buggers him

TS Larissa seduces the teacher and buggers him

xHamster 1 year ago

Three trannies in black leather get sucked by a man before

Three trannies in black leather get sucked by a man before

xHamster 1 year ago

Zara Clark Private Show

Zara Clark Private Show

Flirt4Free 1 week ago

Dominant TS Danni Daniels Threesome

Dominant TS Danni Daniels Threesome

Yeswegays 1 month ago

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

67% 0:39 / 24:48

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

FapHouse 5 months ago

Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad

Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad

Tranny.one 4 years ago

flexing

64% HD 2:00 / 2:23

Flirt4Free 14 years ago

Wild Sabrina Private Show

47% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free 6 years ago

Owen & Stivens & Patric Private Show

HD 2:00 / 23:20

Owen & Stivens & Patric Private Show

Flirt4Free 3 years ago

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

xHamster 6 months ago

Ts creampie guys ass first time Punish my nineteen year-old caboose and mouth

Ts creampie guys ass first time Punish my nineteen year-old caboose and mouth

Eporner 2 years ago

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

53% 1:01 / 24:48

When I Get Home I Find a Tranny with a Huge Dick Who Fucked My Partner and so I Punish Her.

FapHouse 5 months ago

Release Me! Superman is the Villain's Bitch by ManUpFilms

Release Me! Superman is the Villain's Bitch by ManUpFilms

xHamster 1 year ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Sheshaft 11 months ago

Aubrey Kate Dominates Pierce Paris

Aubrey Kate Dominates Pierce Paris

Tranny.one 2 months ago

Matt & Oliver & Andres Private Show

68% HD 2:00 / 4:56

Matt & Oliver & Andres Private Show

Flirt4Free 3 years ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 2 months ago

Slave rental

xHamster 11 months ago

Priscilla makes her slave happy with her hard cock

Priscilla makes her slave happy with her hard cock

xHamster 1 year ago

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

xHamster 1 year ago

Busty trans Daisty Taylor gets dominated

Busty trans Daisty Taylor gets dominated

PornDR 3 years ago

Executioners

Some.Porn 11 months ago

Nvh-055 Transsexual Bondage Training Lesbian Female Teacher Punishes Student 18+ As Extracurricular Lesson Suzune Nico/arimura Nozomi

Nvh-055 Transsexual Bondage Training Lesbian Female Teacher Punishes Student 18+ As Extracurricular Lesson Suzune Nico/arimura Nozomi

getTranny 8 months ago

Black tranny domina punishes a guy's anus hard

Black tranny domina punishes a guy's anus hard

aShemaleTube 7 months ago

Sophia Loreen Private Show

HD 2:00 / 10:40

Sophia Loreen Private Show

Flirt4Free 2 days ago

Blonde Latex TS sub Lianna Lawson -Censored- and anal sex punishment by master Dominic Pacifico

Blonde Latex TS sub Lianna Lawson -Censored- and anal sex punishment by master Dominic Pacifico

Sheshaft 7 months ago

Thonged legs in nylons tied blond Ranie Mae with hands in strappado gets whipped then in second scene black Ana Foxxx gets corporal torture by lezdom Claire Adams on device servitude

Thonged legs in nylons tied blond Ranie Mae with hands in strappado gets whipped then in second scene black Ana Foxxx gets corporal torture by lezdom Claire Adams on device servitude

Ebony8 3 months ago

Sasha Earth sissy crossdresser have hard anal sex with strap on by dominatrix girlfriend

Sasha Earth sissy crossdresser have hard anal sex with strap on by dominatrix girlfriend

SissyFlix 1 year ago

BDSM master puts stick in sub's gaping pussy after fingering

BDSM master puts stick in sub's gaping pussy after fingering

Some.Porn 1 year ago

Delivery guy gets tipped by the kinky TS babe with the hardcore anal banging

Delivery guy gets tipped by the kinky TS babe with the hardcore anal banging

Tranny.one 4 years ago

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

HD 0:39 / 11:00

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

FapHouse 6 months ago

Sexy TS Viviana Rose gets fucked by The BBC PUNISHER

Sexy TS Viviana Rose gets fucked by The BBC PUNISHER

aShemaleTube 4 months ago

The Reward for the Locked-up Sissy

66% HD 0:39 / 12:56

The Reward for the Locked-up Sissy

FapHouse 5 months ago

Sexy ebony trans punishing her submissive bf

Sexy ebony trans punishing her submissive bf

Sheshaft 2 months ago

In the Clothes of her Mistress

HD 0:13 / 16:06

In the Clothes of her Mistress

IWantClips 8 years ago

Top 10 Sissy Ideas 2023

HD 0:39 / 23:35

Top 10 Sissy Ideas 2023

FapHouse 1 year ago

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

Trashreality 9 months ago

TRANSFIXED - Two Naughty Students In Detention Get Punished Well By Her Hot Trans Teacher TS Foxxy

TRANSFIXED - Two Naughty Students In Detention Get Punished Well By Her Hot Trans Teacher TS Foxxy

Eporner 4 months ago

Trans Maid Kaela Luna Wants to Be Used by Her New Boss

Trans Maid Kaela Luna Wants to Be Used by Her New Boss

ShemaleSex 3 months ago

Luccas & Jhordy Private Show

67% HD 2:00 / 6:43

Luccas & Jhordy Private Show

Flirt4Free 11 months ago

The teacher wants the cock of the young TS Larissa

The teacher wants the cock of the young TS Larissa

xHamster 4 years ago

Sophia Loreen Party on Apr 18, 2026 - Part 3

73% HD 2:00 / 44:10

Sophia Loreen Party on Apr 18, 2026 - Part 3

Flirt4Free 3 weeks ago

Sabrina Smiith Private Show

63% HD 2:00 / 7:26

Sabrina Smiith Private Show

Flirt4Free 6 months ago

Sophia Loreen Party on Nov 5, 2025 - Part 3

66% 4K 2:00 / 25:47

Sophia Loreen Party on Nov 5, 2025 - Part 3

Flirt4Free 6 months ago

Two friends humiliate and punish a sissy

Two friends humiliate and punish a sissy

aShemaleTube 2 years ago

A Disgrace to Our Town Part 1

A Disgrace to Our Town Part 1

xHamster 1 year ago

Wanted: Episode 1

Wanted: Episode 1

Some.Porn 8 months ago

Triple Domme CBT: Pulled, Punched & Punished

62% HD 0:10 / 14:14

Triple Domme CBT: Pulled, Punched & Punished

LoyalFans 5 months ago

Japanese Shemale Fucks Female - Niko Suzune & Nozomi Arimura

Japanese Shemale Fucks Female - Niko Suzune & Nozomi Arimura

Eporner 7 months ago

Are You Ready to Please Your Mistress

Are You Ready to Please Your Mistress

xHamster 3 months ago

Sophie Fantasy Private Show

61% HD 2:00 / 1:17:45

Sophie Fantasy Private Show

Flirt4Free 3 years ago

I Fucked My New Toy, and I Left All My Cum Inside It

61% HD 2:00 / 4:00

I Fucked My New Toy, and I Left All My Cum Inside It

Flirt4Free 3 years ago

Topping Emma Rose

45% HD 0:10 / 20:34

Topping Emma Rose

LoyalFans 3 months ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

xHamster 2 months ago

Desire Sweet Private Show

HD 2:00 / 12:31

Desire Sweet Private Show

Flirt4Free 1 year ago

TS Viviana Rose gets Punished #1 OMG shes so sexy 😍

TS Viviana Rose gets Punished #1 OMG shes so sexy 😍

aShemaleTube 3 months ago

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