Punish Videos (38,544)

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Sexy Police Outfit I Was a Naughty Boy and the Police Lady Had to Show Me What Happens to Naughty Boys

HD 0:39 / 15:46

Sexy Police Outfit I Was a Naughty Boy and the Police Lady Had to Show Me What Happens to Naughty Boys

FapHouse 1 year ago

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Tranny.one 4 years ago

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

HD 1:01 / 15:56

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

FapHouse 2 months ago

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

69% HD 0:10 / 26:24

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

LoyalFans 9 months ago

TS Larissa seduces the teacher and buggers him

TS Larissa seduces the teacher and buggers him

xHamster 1 year ago

Shemale Punishes Her Puffy Nipples Until Lactation

68% HD 1:01 / 5:40

Shemale Punishes Her Puffy Nipples Until Lactation

FapHouse 4 months ago

”Transgender in chastity punished & anal fucked”

”Transgender in chastity punished & anal fucked”

Rainblow 1 year ago

futa nurse pegging part 4: double Dommed, punished, facialed w/ Kendall Morr

HD 0:10 / 29:52

futa nurse pegging part 4: double Dommed, punished, facialed w/ Kendall Morr

LoyalFans 6 months ago

School teenie Practices Painfull Sensation

School teenie Practices Painfull Sensation

GayVids 3 years ago

Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

57% HD 1:01 / 24:06

Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

FapHouse 4 weeks ago

Thirsty Boy Gets Fed & Fucked!

Thirsty Boy Gets Fed & Fucked!

FapHouse 5 months ago

you were meant to be a girl: loving feminization and pov bj - full video on Veggiebabyy Manyvids

you were meant to be a girl: loving feminization and pov bj - full video on Veggiebabyy Manyvids

xHamster 7 months ago

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

HD 1:01 / 16:04

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

FapHouse 2 weeks ago

Busty Ts punishes her maid by destrying her pussy

Busty Ts punishes her maid by destrying her pussy

aShemaleTube 1 week ago

I was so overwhelmed that I had to take care of myself

I was so overwhelmed that I had to take care of myself

xHamster 3 weeks ago

”Ass tbabe Jessy Dubai punishes Ruckus & gives him BDSM session”

”Ass tbabe Jessy Dubai punishes Ruckus & gives him BDSM session”

LesbianBliss 4 days ago

”On The Wrong Track - Reagan Foxx, Madi Collins, Kimmy Kimm”

”On The Wrong Track - Reagan Foxx, Madi Collins, Kimmy Kimm”

TransHero 3 weeks 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

getTranny 1 month ago

Tied up and left in the mud! Wet and messy tranny girl pees in her pants!

Tied up and left in the mud! Wet and messy tranny girl pees in her pants!

xHamster 5 days ago

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

xHamster 1 year ago

trio.

Tranny.one 4 years ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 4 months ago

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

Eporner 2 months ago

Nikolly Gaucha punishes his partner

Nikolly Gaucha punishes his partner

xHamster 1 year ago

Veruzca Bigcock punishes guy so hard

Veruzca Bigcock punishes guy so hard

aShemaleTube 2 months ago

Bad ladyboy punished for cheating

Bad ladyboy punished for cheating

VikiPorn 1 year ago

Shemale gets punished in the prison

Shemale gets punished in the prison

Tranny.one 4 years ago

Draven and The Duchess: Aspen Brooks punishes horny beefcake slave

Draven and The Duchess: Aspen Brooks punishes horny beefcake slave

Tranny.one 4 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 2 months ago

house maid Slave boy punishing with cadle

house maid Slave boy punishing with cadle

xHamster 8 months ago

”big black dick t-girl Leilani Li assfucking destroys tight booty for sub Sage Roux”

”big black dick t-girl Leilani Li assfucking destroys tight booty for sub Sage Roux”

Zatube 1 month ago

Kinky twink gets his ass plummeted by the nasty Tgirl on the couch

Kinky twink gets his ass plummeted by the nasty Tgirl on the couch

Tranny.one 3 years ago

Liam Jacobson Private Show

61% HD 2:00 / 8:50

Liam Jacobson Private Show

Flirt4Free 1 month ago

Jacob Malik Private Show

54% HD 2:00 / 16:32

Jacob Malik Private Show

Flirt4Free 3 months ago

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

xHamster 2 months ago

Love Triangle Lesbian Gangbang

Love Triangle Lesbian Gangbang

Tranny.one 4 years ago

Chastity punishment

Chastity punishment

xHamster 2 months ago

The teacher wants the cock of the young TS Larissa

The teacher wants the cock of the young TS Larissa

xHamster 3 years 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 3 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 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 1 month ago

Please Don't Tell Countess!

Please Don't Tell Countess!

xHamster 1 year ago

Sophia Loreen Strip

53% HD 2:00 / 4:00

Sophia Loreen Strip

Flirt4Free 2 years ago

Jenny Wei gets fucked by The BBC PUNISHER! Full 20 min video available now 😈

Jenny Wei gets fucked by The BBC PUNISHER! Full 20 min video available now 😈

aShemaleTube 7 months ago

The BBC Punisher fucks Jenny Wei

The BBC Punisher fucks Jenny Wei

aShemaleTube 1 year ago

While my best friend is at work, this is the first time I've ever been to work

While my best friend is at work, this is the first time I've ever been to work

xHamster 1 month ago

Mistress and trainee use an old slave

Mistress and trainee use an old slave

Fetishpapa 1 month ago

Colombian Boys Private Show

60% HD 2:00 / 11:48

Colombian Boys Private Show

Flirt4Free 4 months 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

Guy was pretty glad to be anally punished by seductive shemale

Guy was pretty glad to be anally punished by seductive shemale

Tranny.one 8 years ago

Colombian Boys Private Show

49% HD 2:00 / 7:59

Colombian Boys Private Show

Flirt4Free 1 year ago

Busty Mature MILF Punishes Naughty Tranny And Latina With Strapon

Busty Mature MILF Punishes Naughty Tranny And Latina With Strapon

BeMyHole 3 weeks ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 2 weeks ago

A Private Punishment

A Private Punishment

Tranny.one 4 years ago

Bald Black Shemale Gets Hard Anal👌 Punishment Roughly

Bald Black Shemale Gets Hard Anal👌 Punishment Roughly

AnalRZ 7 months ago

TRANSSEXUAL TORTURE - (Full Original Movie in HD Version)

TRANSSEXUAL TORTURE - (Full Original Movie in HD Version)

xHamster 3 years ago

Latex Punishment and Fingering [Chastity OTK finger fuck]

HD 0:10 / 15:30

Latex Punishment and Fingering [Chastity OTK finger fuck]

LoyalFans 2 months ago

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

HD 0:39 / 16:04

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

FapHouse 2 weeks ago

Matt & Oliver & Andres Private Show

70% HD 2:00 / 4:56

Matt & Oliver & Andres Private Show

Flirt4Free 3 years ago

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Tranny.one 4 years 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

xHamster 6 months ago

TS stars Vaniity and Mia Isabella anal punish thieves in a gangbang rope bondage

TS stars Vaniity and Mia Isabella anal punish thieves in a gangbang rope bondage

KeekAss 2 months ago

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Tranny.one 4 years ago

Tovez Private Show

67% HD 2:00 / 36:59

Tovez Private Show

Flirt4Free 1 year ago

frenchbaguettes-yaya-the-punisher

frenchbaguettes-yaya-the-punisher

TransTube.tv 1 year ago

Black Thong Femboy Anal Fucking herself after Wedgie and Cumfarts

Black Thong Femboy Anal Fucking herself after Wedgie and Cumfarts

xHamster 3 weeks ago

Mistress Korra Punishes Naughty With Korra Del Rio

Mistress Korra Punishes Naughty With Korra Del Rio

AbTranny 2 years ago

Elvis & Alfonso & Master Private Show

62% HD 2:00 / 8:58

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Sissy Strained to Suck Mistress's Strap-on Before Getting Fucked Hard

Sissy Strained to Suck Mistress's Strap-on Before Getting Fucked Hard

xHamster 4 months ago

GERMAN BDSM - Mistress domina punish ugly guys painful

GERMAN BDSM - Mistress domina punish ugly guys painful

xHamster 3 years ago

”Latex femdom strapon banging submissive lesbian”

”Latex femdom strapon banging submissive lesbian”

TransHero 2 weeks ago

Fuck the Slut

HD 2:00 / 48:30

Flirt4Free 1 year ago

Hot Asian Shemale Sucks Hard and Takes Rough Punishment in a Wild Triad Scene

Hot Asian Shemale Sucks Hard and Takes Rough Punishment in a Wild Triad Scene

3SumXL 1 year ago

new trans katia. cold water. humilation orders by sasha beart !!!

new trans katia. cold water. humilation orders by sasha beart !!!

PornBox 2 years ago

Boy Ties His Friend to Punish Him on the Roof

Boy Ties His Friend to Punish Him on the Roof

xHamster 1 year ago

cherry and i dominate our disobedient puppies nyxi and livi

41% HD 0:30 / 33:02

cherry and i dominate our disobedient puppies nyxi and livi

AnalVids 1 year ago

Executioners

Some.Porn 7 months ago

Trans Gal Worships His Trans Wang In advance of This guy Wrecks Her Butt

Trans Gal Worships His Trans Wang In advance of This guy Wrecks Her Butt

Lesbian8 1 month ago

Elvis & Alfonso & Master Private Show

55% HD 2:00 / 10:47

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Haycka Fucks the Gardener and Gets Fucked in the Ass by Her Boyfriend

Haycka Fucks the Gardener and Gets Fucked in the Ass by Her Boyfriend

xHamster 9 months ago

Transvestite from hell

Transvestite from hell

xHamster 9 months ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Flirt4Free 1 year ago

Ponytailed Ladyboy Slave For Cock

Ponytailed Ladyboy Slave For Cock

Eporner 3 years ago

Busty TS chick dominates a hogtied submissive masked man

Busty TS chick dominates a hogtied submissive masked man

Tranny.one 4 years ago

Patric & Simon & Frederick Private Show

51% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 1 year ago

Curvy Babes Cumpilation ft Natasha Nice, Jenna Starr - GirlfriendsFilms

Curvy Babes Cumpilation ft Natasha Nice, Jenna Starr - GirlfriendsFilms

Some.Porn 4 months ago

Elias & Elix Private Show

61% HD 2:00 / 13:10

Elias & Elix Private Show

Flirt4Free 2 months ago

Young man gets punished for misbehaving by his TS step mom as she fucks his ass nice and hard

Young man gets punished for misbehaving by his TS step mom as she fucks his ass nice and hard

BeMyHole 4 years ago

The Most beautiful Trans Tits in the World Pinched and Lactating

The Most beautiful Trans Tits in the World Pinched and Lactating

xHamster 1 month ago

Valentina Melo breaks the boy's ass and then she gets her banging

Valentina Melo breaks the boy's ass and then she gets her banging

xHamster 1 year ago

Sophia Loreen Private Show

61% 4K 2:00 / 23:02

Sophia Loreen Private Show

Flirt4Free 7 months ago

Shiri Allwood - Isabella Sorrenti Punishes Peeping Shiri

Shiri Allwood - Isabella Sorrenti Punishes Peeping Shiri

TubeOn 1 year ago

Master & Ithan & Aleex Private Show

57% HD 2:00 / 31:36

Master & Ithan & Aleex Private Show

Flirt4Free 5 months ago

”Lustful Emma Hix tied up & screwed”

”Lustful Emma Hix tied up & screwed”

ThePornstar 1 year ago

Sissy Public Punishment

Premium HD 30:51

Sissy Public Punishment

xnxxGold 3 years ago

Avery Angel gets Punished #2 trailer full video Available now! Only 4.99

Avery Angel gets Punished #2 trailer full video Available now! Only 4.99

aShemaleTube 9 months ago

Orianna Dunn Private Show

65% HD 2:00 / 4:47

Orianna Dunn Private Show

Flirt4Free 1 year ago

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

Tranny.one 4 years ago

It's very easy to get out of bed when it's cold and raining

It's very easy to get out of bed when it's cold and raining

xHamster 2 weeks ago

Real SISSY ENEMA slave cums in his own mouth

Real SISSY ENEMA slave cums in his own mouth

xHamster 1 year ago

Elvis & Alfonso & Master Private Show

Elvis & Alfonso & Master Private Show

Flirt4Free 3 years ago

Christian & Nicco & Elvis Private Show

50% HD 2:00 / 5:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

”Adorable teen in wetlook gets hard punishment”

”Adorable teen in wetlook gets hard punishment”

ThePornstar 7 months ago

Elias & Elix Private Show

55% HD 2:00 / 37:58

Elias & Elix Private Show

Flirt4Free 5 months ago

Shiri Allwood - Gets Punished

Shiri Allwood - Gets Punished

AbTranny 2 years ago

German Domina Punish A Crossdresser Slave

German Domina Punish A Crossdresser Slave

PornUse 3 days ago

Sophia Loreen Party on Dec 17, 2025 - Part 2

4K 2:00 / 20:05

Sophia Loreen Party on Dec 17, 2025 - Part 2

Flirt4Free 3 weeks ago

Courageous TS Natalie Mars bends down and lets the giant rubber cock destroy her asshole

Courageous TS Natalie Mars bends down and lets the giant rubber cock destroy her asshole

Fapnado 2 years ago

Wild Sabrina Private Show

61% HD 2:00 / 9:11

Wild Sabrina Private Show

Flirt4Free 4 years ago

Master & Christian Mckenzie & Christian Rey Private Show

66% HD 2:00 / 7:39

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Oct 23, 2025 - Part 2

65% 4K 2:00 / 23:12

Sophia Loreen Party on Oct 23, 2025 - Part 2

Flirt4Free 2 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Submissive Gets Owned By Four Dommes by TSDomme.com

Submissive Gets Owned By Four Dommes by TSDomme.com

xHamster 1 year ago

TS Mistress Fucks Her Bound Male Slave

TS Mistress Fucks Her Bound Male Slave

TrannyGem 2 days ago

The League of Extraordinary Transsexuals: The Final Punishment

The League of Extraordinary Transsexuals: The Final Punishment

AbTranny 9 years ago

Sexy punishment by hard sissy dick for misspelling

Sexy punishment by hard sissy dick for misspelling

xHamster 4 years ago

Cute Dance with Naughty Girl

Cute Dance with Naughty Girl

Flirt4Free 11 months ago

Dominatrix caning useless slave

Dominatrix caning useless slave

Tranny.one 4 years ago

”Deep Feet Punishment: Mouth Screwed”

”Deep Feet Punishment: Mouth Screwed”

TransHero 3 weeks ago

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