Punish Videos (59,616)

”Alina Lopez lets old man fuck her to avoid punishment!”

”Alina Lopez lets old man fuck her to avoid punishment!”

TransHero 7 months ago

Sophia Loreen Private Show

63% 4K 2:00 / 45:37

Sophia Loreen Private Show

Camster 2 days ago

Latex TS sub chastity and butt fucking sex

Latex TS sub chastity and butt fucking sex

Analdin 2 months ago

Sophia Loreen Private Show

67% HD 2:00 / 4:29

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

lusty lesbian lie part 2

55% HD 0:10 / 11:29

lusty lesbian lie part 2

LoyalFans 5 years ago

Assfucked Maid Jasmine

Assfucked Maid Jasmine

FapHouse 6 months ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

XHamster 2 months ago

Aleex & Paulo Private Show

52% HD 2:00 / 8:12

Aleex & Paulo Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 8 months ago

Severe punishment for Bella to teach her who’s the Boss.

HD 0:10 / 10:40

Severe punishment for Bella to teach her who’s the Boss.

LoyalFans 3 weeks 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 11 months ago

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

69% HD 1:01 / 15:56

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

FapHouse 8 months ago

Amateur UK crossdressers suck fuck with Grandpa and step dad CD

Amateur UK crossdressers suck fuck with Grandpa and step dad CD

Tranny.one 4 years ago

Step mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min - Teaser Video

Step mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min - Teaser Video

GetTranny 3 years ago

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

65% 4K 0:30 / 58:54

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

Clips4sale 1 year ago

Punished sissy

56% HD 0:39 / 34:04

FapHouse 5 years ago

Stepdaddy and little shemale brat Chelsea Marie

Stepdaddy and little shemale brat Chelsea Marie

Eporner 2 years ago

TS goddesses punish the amateur sex robbers

TS goddesses punish the amateur sex robbers

Analdin 2 months ago

The cross dresser is punished

56% 0:11 / 2:13

The cross dresser is punished

Clips4sale 2 years ago

Lika Kai Private Show

Lika Kai Private Show

Camster 2 weeks ago

Viky & Master Private Show

63% HD 2:00 / 5:28

Viky & Master Private Show

Flirt4Free 11 months ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Yeswegays 1 year ago

Chubby ginger-haired babe punished with belt and dick by a hot shemale

Chubby ginger-haired babe punished with belt and dick by a hot shemale

GayX 3 months ago

School uniform tranny analized by principal

School uniform tranny analized by principal

Tranny.one 4 years ago

Ambar & Oliver Party on May 1, 2026 - Part 2

61% HD 2:00 / 44:48

Ambar & Oliver Party on May 1, 2026 - Part 2

Camster 2 months ago

TGIRLS HOOKUP: Lying Top Gets Humiliated and Punished!

TGIRLS HOOKUP: Lying Top Gets Humiliated and Punished!

Fapnado 2 years ago

Sophia Loreen Party on Jul 18, 2026 - Part 3

HD 2:00 / 48:02

Sophia Loreen Party on Jul 18, 2026 - Part 3

Flirt4Free 1 week ago

Ladyboy Amy Punished Bareback

Ladyboy Amy Punished Bareback

Eporner 8 years ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

XHamster 2 months ago

Nutty Bareback Punishment

Nutty Bareback Punishment

Some.Porn 1 year ago

Naughty tranny gets punished by Dom

Naughty tranny gets punished by Dom

Analdin 2 months ago

$Sex and Cum in Elias\' Mouth$ 58% HD 2:00 / 35:38

Sex and Cum in Elias\' Mouth

Flirt4Free 10 months ago

Tania training slave part 2

67% 4K 0:10 / 11:26

Tania training slave part 2

Clips4sale 2 years ago

Mature crossdresser punishing masked slave in BDSM session

Mature crossdresser punishing masked slave in BDSM session

PornLib 2 years ago

gangbang part.2 - punishing the mechanic who didnt deliver the job

gangbang part.2 - punishing the mechanic who didnt deliver the job

PornOne 1 year ago

Mike Swift & David Golden Private Show

HD 2:00 / 32:38

Mike Swift & David Golden Private Show

Flirt4Free 6 days ago

Patricia the crossdresser gets a good spanking and six of the best!

67% HD 0:10 / 3:59

Patricia the crossdresser gets a good spanking and six of the best!

LoyalFans 11 months ago

Luccas & Jhordy Private Show

63% HD 2:00 / 7:43

Luccas & Jhordy Private Show

Flirt4Free 1 year ago

Cheating 18yo Twink Femboy Gets Anal Bareback Punishment by His Boyfriend

Cheating 18yo Twink Femboy Gets Anal Bareback Punishment by His Boyfriend

XHamster 2 years ago

”TS Nanny Natalie Mars Gets Caught in the Act!”

”TS Nanny Natalie Mars Gets Caught in the Act!”

4Wank 2 years ago

Sophia’s Playful Lesbian Challenge

Sophia’s Playful Lesbian Challenge

ALOTPorn 4 days ago

HOT Trans Avery Angel gets fucked by the BBC PUNISHER and takes a nice facial cumshot

HOT Trans Avery Angel gets fucked by the BBC PUNISHER and takes a nice facial cumshot

AShemaleTube 1 year ago

Jennifer Skanes Private Show

HD 2:00 / 19:02

Jennifer Skanes Private Show

Camster 3 weeks ago

Training My Sissy

46% HD 0:15 / 8:49

Training My Sissy

Clips4sale 4 years ago

Extremely sensitive nipples after extreme sucking. My pimped-up tits want to be treated hard and consistently.

Extremely sensitive nipples after extreme sucking. My pimped-up tits want to be treated hard and consistently.

XHamster 3 days ago

”Nasty Student Gets Punished By Angry Stepfather”

”Nasty Student Gets Punished By Angry Stepfather”

ThePornstar 9 months ago

Trans Girl Punishes And Dominates This Guy And Destroys His Asshole Roughly

Trans Girl Punishes And Dominates This Guy And Destroys His Asshole Roughly

BeMyHole 2 years ago

Exotic stepdaughter sucks huge dick and ends up cr

Exotic stepdaughter sucks huge dick and ends up cr

ALOTPorn 1 year ago

Shemale Pornstar: Natalia Coxxx

63% HD 0:30 / 1:36:00

Shemale Pornstar: Natalia Coxxx

AEBN 16 years ago

LACED #39 Preview! (SADISM & MASOCHISM ASMR) Jizz Hatch Femboy Puppy Punished & Milked! (Utter:LaceVoid,com)

LACED #39 Preview! (SADISM & MASOCHISM ASMR) Jizz Hatch Femboy Puppy Punished & Milked! (Utter:LaceVoid,com)

GayCK 4 years ago

Julieta Shayk Private Show

Julieta Shayk Private Show

Camster 5 years ago

Jacob Malik Private Show

Jacob Malik Private Show

Flirt4Free 1 year ago

Set Life

Some.Porn 1 year ago

Jewel Selfsucker Private Show

66% HD 2:00 / 4:31

Jewel Selfsucker Private Show

Flirt4Free 6 days ago

Asian Shemale Takes on 3 Big Cocks

Asian Shemale Takes on 3 Big Cocks

XHamster 8 years ago

Ryan Boness & Eduar Senni Private Show

Ryan Boness & Eduar Senni Private Show

Flirt4Free 1 month ago

Lady Fee Punishes Sissy Dee for Playing with Her Toys

Lady Fee Punishes Sissy Dee for Playing with Her Toys

XHamster 1 month ago

TRANSEROTICA - Sexbot Natalie Mars submits to BDSM with Asian mistress

TRANSEROTICA - Sexbot Natalie Mars submits to BDSM with Asian mistress

AShemaleTube 2 weeks ago

Part 1- Lanista Bear Has Maid Jayne and Bottom Feeder to Worship His Body

HD 0:39 / 13:22

Part 1- Lanista Bear Has Maid Jayne and Bottom Feeder to Worship His Body

FapHouse 2 weeks ago

Trans Stepsister Femdom

Trans Stepsister Femdom

XHamster 1 year ago

Crossdresser Valerie Cums Hard in Nylon Stockings

Crossdresser Valerie Cums Hard in Nylon Stockings

WebcamBros 1 month ago

Trans Sub Ana Cums Over and Over PART 1

61% HD 0:30 / 8:40

Trans Sub Ana Cums Over and Over PART 1

Clips4sale 4 years ago

My girlfriend in video training me to the handjob I fail and punish me for swallowing my juice

My girlfriend in video training me to the handjob I fail and punish me for swallowing my juice

XHamster 1 month ago

Mistress and Her maid

73% 0:20 / 6:51

Mistress and Her maid

Clips4sale 1 year ago

BITCH STEPMOM Makes her Fem Pussy HOUSEBOY Vacuum then turns him into her Footrest

BITCH STEPMOM Makes her Fem Pussy HOUSEBOY Vacuum then turns him into her Footrest

XHamster 6 days ago

Carter Rains Private Show

57% 4K 2:00 / 11:15

Carter Rains Private Show

Camster 3 weeks ago

Dimitri Caruso Private Show

HD 2:00 / 22:05

Dimitri Caruso Private Show

Flirt4Free 4 years ago

Trans Dominatrix Girl Punishes This Guy By Destroying His Ass

Trans Dominatrix Girl Punishes This Guy By Destroying His Ass

BeMyHole 2 years ago

Priscilla makes her slave happy with her hard cock

Priscilla makes her slave happy with her hard cock

XHamster 1 year ago

Peeper's Punishment: TS Foxxy Takes Down Peeping Tom

HD 0:30 / 33:00

Peeper's Punishment: TS Foxxy Takes Down Peeping Tom

AEBN 2 weeks ago

Femtop.xxx - Roxxie Moth - Latex Sub Aphrodyte Adams Punished For Sneaking Out

Femtop.xxx - Roxxie Moth - Latex Sub Aphrodyte Adams Punished For Sneaking Out

AbTranny 4 years ago

Strap-on & chastity punishment for stealing Mistress' clothes 😭🔐 @Saskia_and_Sasha on OF

Strap-on & chastity punishment for stealing Mistress' clothes 😭🔐 @Saskia_and_Sasha on OF

AShemaleTube 1 year ago

You were a bad boy! As a punishment, punch yourself while jerking off! JOI CBT GERMAN

You were a bad boy! As a punishment, punch yourself while jerking off! JOI CBT GERMAN

XHamster 1 year ago

Cock Prisoner Aroma Obsession

Cock Prisoner Aroma Obsession

XHamster 1 week ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 5 days ago

COCK IN A FROCK #6

74% 4K 0:30 / 13:00

COCK IN A FROCK #6

Clips4sale 2 years ago

Tranny Bondage Cock Sucking Fest

Tranny Bondage Cock Sucking Fest

AbTranny 8 years ago

Booty Calls Ep 1: Shiri Allwood Fucks Nikki Darling's Whore Holes!

Booty Calls Ep 1: Shiri Allwood Fucks Nikki Darling's Whore Holes!

XHamster 9 months ago

Paul Walkers Private Show

HD 2:00 / 23:30

Paul Walkers Private Show

Flirt4Free 1 day ago

Part 2. My mistress punishes my ass because I was disobedient

Part 2. My mistress punishes my ass because I was disobedient

XHamster 2 months ago

Home College

Some.Porn 2 years ago

BDSM anal babe whipped and throatfucked by master

BDSM anal babe whipped and throatfucked by master

Some.Porn 2 years ago

angelina please and sergeant miles my army stepdad fucks me for misbehaving

angelina please and sergeant miles my army stepdad fucks me for misbehaving

TransDoe 2 years ago

”Transgender in chastity punished & anal fucked”

”Transgender in chastity punished & anal fucked”

ThePornstar 1 year ago

Big Girl Dick TS Chanel Jordan, fucks Pretty Trans girl, Gray Perrier in doggy with red lingerie

Big Girl Dick TS Chanel Jordan, fucks Pretty Trans girl, Gray Perrier in doggy with red lingerie

XHamster 8 months ago

Femboy Raven Punishing her Puffy Nipples and Lactating her Growing Tits with Vacuum Machine Clip 1

Femboy Raven Punishing her Puffy Nipples and Lactating her Growing Tits with Vacuum Machine Clip 1

XHamster 1 month ago

Alexxa & Francesco Private Show

55% HD 2:00 / 4:56

Alexxa & Francesco Private Show

Flirt4Free 3 years ago

Fat blonde slut gets spanked by her horny master

Fat blonde slut gets spanked by her horny master

XHamster 2 years ago

Jhon & Derek & Chris Private Show

44% HD 2:00 / 32:48

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

Hung Latina Tgirl Punished by Boyfriend with Choking Slapping & Rough Anal

Hung Latina Tgirl Punished by Boyfriend with Choking Slapping & Rough Anal

TrannyGem 7 years ago

Lady In Black - in need for punishment, dicks and cum

Lady In Black - in need for punishment, dicks and cum

XHamster 1 year ago

Spice Up Your Love Life With T-girl Daisy Taylor And Ricky Larkin's Role Play Adventure

Spice Up Your Love Life With T-girl Daisy Taylor And Ricky Larkin's Role Play Adventure

Eporner 1 year ago

Submissive ladyboy slut got mouth and ass used

Submissive ladyboy slut got mouth and ass used

Sheshaft 2 years ago

Busty ebony shemale anal fucks blonde

Busty ebony shemale anal fucks blonde

Eporner 4 years ago

Extreme Anal Sissy Femboy Fucked Compilation Nasty Cosplay Ass Gaped

62% HD 0:39 / 35:30

Extreme Anal Sissy Femboy Fucked Compilation Nasty Cosplay Ass Gaped

FapHouse 10 months ago

Sophie Fantasy Private Show

Sophie Fantasy Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Jul 17, 2026 - Part 4

61% HD 2:00 / 43:44

Sophia Loreen Party on Jul 17, 2026 - Part 4

Flirt4Free 1 week ago

”Thicc Juicy BBQ”

”Thicc Juicy BBQ”

429Men 6 months ago

Japanese MILF Anal - Rough Deep Creampie Punishment Shemale

Japanese MILF Anal - Rough Deep Creampie Punishment Shemale

POVJP 1 year ago

Cruel dominatrix spanks incel

Cruel dominatrix spanks incel

Some.Porn 1 year ago

Luna Florez Private Show

Luna Florez Private Show

Camster 2 weeks ago

Four shemales in black leather dominate a man before cumming

Four shemales in black leather dominate a man before cumming

XHamster 2 years ago

Natasha Milk Private Show

Natasha Milk Private Show

Camster 1 week ago

Chanel Santini Has To Punish Her Employees When They Get Caught Masturbating On The Clock!

Chanel Santini Has To Punish Her Employees When They Get Caught Masturbating On The Clock!

BeMyHole 2 years ago

Brunette tranny punisher with huge ass spanks and fucks until cumshot

Brunette tranny punisher with huge ass spanks and fucks until cumshot

AShemaleTube 2 years ago

Spanked by the Sadistic Sex Fiends!

Premium 62% HD 39:45

Spanked by the Sadistic Sex Fiends!

TransAngels 6 years ago

Discipline Day For Joanne 1 The Pre Caning Warm Up

Discipline Day For Joanne 1 The Pre Caning Warm Up

Tranny.one 4 years ago

TS Seduction: Exercise Torment By Sexy, Fitness Babe, Jaquelin Braxton

57% HD 0:30 / 46:00

TS Seduction: Exercise Torment By Sexy, Fitness Babe, Jaquelin Braxton

AEBN 9 years ago

Vicky Katherine Private Show

64% HD 2:00 / 28:15

Vicky Katherine Private Show

Flirt4Free 3 years ago

Punish Babe 3D Hardcore Doggystyle Milf

Punish Babe 3D Hardcore Doggystyle Milf

Tranny.one 6 years ago

Natalie Mars Punishment

Natalie Mars Punishment

Eporner 2 years ago

Avery Angel gets fucked by The BBC PUNISHER and takes a nasty facial cumshot

Avery Angel gets fucked by The BBC PUNISHER and takes a nasty facial cumshot

AShemaleTube 1 year ago

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Piss

68% HD 0:39 / 31:35

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Piss

FapHouse 3 months ago

Sophia Loreen Party on Jul 23, 2026 - Part 4

HD 2:00 / 13:47

Sophia Loreen Party on Jul 23, 2026 - Part 4

Flirt4Free 1 week ago

Sexy tbabe Cassidy Quinn spanked hard and diapered

Sexy tbabe Cassidy Quinn spanked hard and diapered

Tranny.one 4 years ago

Sophia Loreen Private Show

4K 2:00 / 17:41

Sophia Loreen Private Show

Camster 2 days ago

Sara & Elver Private Show

66% HD 2:00 / 6:50

Sara & Elver Private Show

Flirt4Free 8 months ago

Tranny Secretary Gets Wedgied and Spanked

Tranny Secretary Gets Wedgied and Spanked

XHamster 8 months ago

”Hot tbabe Stefani Special rails stranger Endza Adairs in the sauna”

”Hot tbabe Stefani Special rails stranger Endza Adairs in the sauna”

ThePornstar 3 months ago

Mara Nova and Sydney Farron In Punishment by Principal

Mara Nova and Sydney Farron In Punishment by Principal

Tranny.one 6 years ago

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