Punishment Videos (42,170)

Sissy in Bondage Teased by Mistress

Sissy in Bondage Teased by Mistress

FapHouse 1 week ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 4 months ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

Futa Anna Punishes the Submissive Burglar in Her House

Futa Anna Punishes the Submissive Burglar in Her House

3DPornDude 1 month ago

Busty brunette babe getting her ass red after getting spanked by her punisher

Busty brunette babe getting her ass red after getting spanked by her punisher

xHamster 2 years ago

Pink Latex Shebabe Punishes Her Bf

Pink Latex Shebabe Punishes Her Bf

Eporner 3 months ago

Trap revealed but still fucked by the two black thugs

Trap revealed but still fucked by the two black thugs

Tranny.one 3 years ago

Trans Demon Punishes You with Her Huge Dick and Massive Load of Hot Cum

HD 1:01 / 25:52

Trans Demon Punishes You with Her Huge Dick and Massive Load of Hot Cum

FapHouse 2 weeks ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

xHamster 2 months ago

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

Sissy slave Alina Painwhore is dominated, mouth fucked drinks piss got humiliative punishment for missing piss on toilet floor

xHamster 1 year ago

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

60% HD 1:01 / 28:08

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

FapHouse 3 months ago

Kitty Kunt and her huge she cock

Kitty Kunt and her huge she cock

xHamster 2 months ago

Zoe dominates and punishes her submissive with her tight pecker in spandex

Zoe dominates and punishes her submissive with her tight pecker in spandex

TrannyMovs 1 week ago

Tall shemale domme flogs and anal fucks man

Tall shemale domme flogs and anal fucks man

Eporner 2 years ago

Muscle man gets dominated by the nasty TS chick in this hardcore sex

Muscle man gets dominated by the nasty TS chick in this hardcore sex

Tranny.one 4 years ago

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

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

xHamster 4 months ago

Sasha Earth Takes it Up the Ass from Strapon-Wielding Russian Dominatrix

Sasha Earth Takes it Up the Ass from Strapon-Wielding Russian Dominatrix

XXXShake 1 year ago

Puffy Nipples Teen Shemale Lactating and Punished with Vacuum Machine and Slapped with Big Brown Dildo

HD 0:39 / 36:44

Puffy Nipples Teen Shemale Lactating and Punished with Vacuum Machine and Slapped with Big Brown Dildo

FapHouse 1 week ago

GERMAN BDSM - Mistress domina punish ugly guys painful

GERMAN BDSM - Mistress domina punish ugly guys painful

xHamster 3 years ago

Sissy Slave Tranny Punished & Fucked - Full Video

Sissy Slave Tranny Punished & Fucked - Full Video

xHamster 4 years ago

TS Mistress Fucks Her Bound Male Slave

TS Mistress Fucks Her Bound Male Slave

Xozilla 1 week ago

Huge Cock Tranny Fucks Male Slave!

Huge Cock Tranny Fucks Male Slave!

Eporner 3 years ago

Tranny maid River Enza disciplined for being naughty

Tranny maid River Enza disciplined for being naughty

UrGayPorn 1 year ago

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

63% 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 6 months ago

”Shemale Delia DeLions punishes stepson & Siouxsie Q in spicy 3some”

”Shemale Delia DeLions punishes stepson & Siouxsie Q in spicy 3some”

ThePornstar 1 month ago

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

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

4Wank 2 years ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

xHamster 1 year ago

I Need to Be Punished

I Need to Be Punished

FapHouse 9 months ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 9 months ago

Blond hair babe Femdom Tranny Butt sex Nailing

Blond hair babe Femdom Tranny Butt sex Nailing

Analdin 6 days ago

Threesome with bella

Threesome with bella

Tranny.one 4 years ago

I'm Your Nasty Girl: Eva Maxim Submits Her Body to Ricky Larkin

I'm Your Nasty Girl: Eva Maxim Submits Her Body to Ricky Larkin

xHamster 2 months ago

Part 2 - Domina-Satana and I sensually play with Booboo with smoking.

Part 2 - Domina-Satana and I sensually play with Booboo with smoking.

xHamster 1 month ago

Trans Demon Punishes You With Her Huge Dick And Massive Load of Hot Cum

Trans Demon Punishes You With Her Huge Dick And Massive Load of Hot Cum

xHamster 3 weeks ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 3 months ago

Blonde TS Samara De Macedo Gangbanged

Blonde TS Samara De Macedo Gangbanged

Sheshaft 4 years ago

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

HD 0:23 / 41:59

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

AnalVids 2 weeks ago

Lady Punishes Her Sissy Slut Michelle for Not Wearing Propper Lingerie for Bed

Lady Punishes Her Sissy Slut Michelle for Not Wearing Propper Lingerie for Bed

xHamster 2 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 7 months ago

Jade Indica, Lorelei Lee and Sexy Jade Part 3 of 4 of the June Live Feed

Premium 63% HD 41:55

Jade Indica, Lorelei Lee and Sexy Jade Part 3 of 4 of the June Live Feed

Kink 16 years ago

Skinny dude buttfucked by stranger

Skinny dude buttfucked by stranger

Some.Porn 9 months ago

Jacob Malik Private Show

58% HD 2:00 / 11:23

Jacob Malik Private Show

Flirt4Free 3 months ago

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

xHamster 1 month ago

Extreme Cock & Ball Torture Device (DIY)

Extreme Cock & Ball Torture Device (DIY)

xHamster 1 year ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

xHamster 7 months ago

This cute asian ladyboy needs a real hard punishement

This cute asian ladyboy needs a real hard punishement

Sheshaft 5 years ago

Big Tits Shemale Raven Slapping and Lactating Her Puffy Nipples

Big Tits Shemale Raven Slapping and Lactating Her Puffy Nipples

xHamster 5 days ago

Officer Punished A Horny Shemale At The Court

Officer Punished A Horny Shemale At The Court

Eporner 1 year ago

Danni Daniels Fucks Straight Couple in The Red Light Restricted Scene

Danni Daniels Fucks Straight Couple in The Red Light Restricted Scene

Pornicom 2 weeks ago

Chubby stepmom in stockings deepthroats before getting buttfucked

Chubby stepmom in stockings deepthroats before getting buttfucked

Some.Porn 2 years ago

Leather outfit ts domina punishes her slave's ass and mouth

Leather outfit ts domina punishes her slave's ass and mouth

aShemaleTube 4 months ago

Femboy maid gets caught playing Project QT and has to be punished

Femboy maid gets caught playing Project QT and has to be punished

ShemaleSin 1 year ago

”StepSiblingsCaught: My Stepsis Alicia Williams Wants Me To Walk Her Like A Dog”

”StepSiblingsCaught: My Stepsis Alicia Williams Wants Me To Walk Her Like A Dog”

ThePornstar 1 year ago

Sophia Loreen Party on Oct 31, 2025 - Part 2

55% 4K 2:00 / 6:28

Sophia Loreen Party on Oct 31, 2025 - Part 2

Flirt4Free 7 months ago

Thai Transgender WomanFembabythwas Punished By Having Ejaculation Inside Her Anus

Thai Transgender WomanFembabythwas Punished By Having Ejaculation Inside Her Anus

Eporner 1 week ago

Roy & Hercules & Jamer Private Show

46% HD 2:00 / 4:09

Roy & Hercules & Jamer Private Show

Flirt4Free 3 years ago

Four shemale punishers in black leather outfits manhandle a

Four shemale punishers in black leather outfits manhandle a

xHamster 1 year ago

Melaniie Moon Private Show

HD 2:00 / 50:49

Melaniie Moon Private Show

Flirt4Free 1 week ago

Step-mommy Teaches You About Condoms JOI

Step-mommy Teaches You About Condoms JOI

xHamster 1 year ago

Pride and Orifice Part 2

Premium HD 30:35

Pride and Orifice Part 2

TransAngels 3 years ago

Sabrisse and Jia Lissa in wild lesbian 69 with trimmed pussy and high heels

Sabrisse and Jia Lissa in wild lesbian 69 with trimmed pussy and high heels

Some.Porn 2 years 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 5 months ago

Big-titted MILF pounded by stunningTS

Big-titted MILF pounded by stunningTS

Some.Porn 10 months ago

Humiliated By Two Futas - Ft Imilia Audley & TheeCeleste

Humiliated By Two Futas - Ft Imilia Audley & TheeCeleste

Clips4sale 1 year ago

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

52% 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 6 months ago

Athletic trans loves painal by bbc

Athletic trans loves painal by bbc

Sheshaft 3 months ago

Consequences for Breaking Out of Chastity

65% HD 1:01 / 42:05

Consequences for Breaking Out of Chastity

FapHouse 2 weeks ago

Tiny Liar Devoured by My Huge Cock - Caught Forever in My Balls

Tiny Liar Devoured by My Huge Cock - Caught Forever in My Balls

xHamster 4 months ago

Jacob Malik Private Show

56% HD 2:00 / 8:46

Jacob Malik Private Show

Flirt4Free 3 months ago

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

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

xHamster 2 weeks ago

Sami - Femboy Punished by Futa for Spilling the Order

Sami - Femboy Punished by Futa for Spilling the Order

3DPornDude 2 weeks ago

The Most beautiful Trans Tits in the World Pinched and Lactating

The Most beautiful Trans Tits in the World Pinched and Lactating

xHamster 6 months ago

Four femdom shemales punish males

Four femdom shemales punish males

Analdin 1 week ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 week ago

Luccas & Jhordy & Master Private Show

56% HD 2:00 / 12:04

Luccas & Jhordy & Master Private Show

Flirt4Free 3 months ago

Nicco & Patric & Santiago Have Amazing Threesome

62% HD 2:00 / 1:04:58

Nicco & Patric & Santiago Have Amazing Threesome

Flirt4Free 2 years ago

Melaniie Moon Private Show

Melaniie Moon Private Show

Flirt4Free 2 days ago

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Sarah Dark her Own Crossdressing Sissy

Sarah Dark her Own Crossdressing Sissy

its.PORN 7 years ago

See the New Slave They Humiliate, Torment & Hard Fist

65% HD 1:01 / 18:02

See the New Slave They Humiliate, Torment & Hard Fist

FapHouse 1 year ago

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

51% HD 0:39 / 7:52

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

FapHouse 1 month ago

Paulo & Jose & Sander Private Show

67% HD 2:00 / 7:57

Paulo & Jose & Sander Private Show

Flirt4Free 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

stupid shy brat boy from TS unmasked, humiliated and fucked hard until she breeds him

stupid shy brat boy from TS unmasked, humiliated and fucked hard until she breeds him

aShemaleTube 6 months 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 6 months ago

Daphne Millerr Private Show

4K 2:00 / 21:09

Daphne Millerr Private Show

Flirt4Free 1 week ago

Denali Danger gets Punished #2

Denali Danger gets Punished #2

aShemaleTube 1 year ago

Sophia Loreen Party on May 1, 2026 - Part 3

HD 2:00 / 1:44:32

Sophia Loreen Party on May 1, 2026 - Part 3

Flirt4Free 1 month ago

Bukkake #2 the *** 9 T-girls Mass Cumming

55% HD 1:01 / 29:41

Bukkake #2 the *** 9 T-girls Mass Cumming

FapHouse 3 years ago

Freaks of Nature 26 Older Fisted and Snatch Slapping

Freaks of Nature 26 Older Fisted and Snatch Slapping

Amateur8 5 years ago

Anal Gaping!

xHamster 6 days ago

A Private Discipline

A Private Discipline

Some.Porn 5 months ago

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

TS Kendall Penny dominates Bussy Bradley with -Censored- BDSM

Sheshaft 1 year ago

Daphne Millerr Private Show

Daphne Millerr Private Show

Flirt4Free 1 week ago

FEMINIZED - Rubber Maid Punishment (Natalie Mars, Shiri

FEMINIZED - Rubber Maid Punishment (Natalie Mars, Shiri

IcePorn 11 months ago

This Is How I Punish Myself When I Am Too Sorry

This Is How I Punish Myself When I Am Too Sorry

xHamster 10 months ago

cherry and i dominate our disobedient puppies nyxi and livi

61% HD 0:30 / 33:02

cherry and i dominate our disobedient puppies nyxi and livi

PornBox 1 year ago

Corrine Dittmann Private Show

59% 4K 2:00 / 5:04

Corrine Dittmann Private Show

Flirt4Free 9 months ago

Sabrina Smiith Private Show

70% 4K 2:00 / 10:26

Sabrina Smiith Private Show

Flirt4Free 5 months 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 6 months ago

Lucy Hart Makes me SO Heavy at SweetFemdom

Lucy Hart Makes me SO Heavy at SweetFemdom

xHamster 6 days ago

Avery Angel gets fucked by The BBC PUNISHER! Full 22 min vid available now! SO HOT!

Avery Angel gets fucked by The BBC PUNISHER! Full 22 min vid available now! SO HOT!

aShemaleTube 9 months ago

Jhordy & Maxx Private Show

42% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

Black Futa With A Huge Cock Punishes The Housekeeper

Black Futa With A Huge Cock Punishes The Housekeeper

AbTranny 1 week ago

I want it like this before she comes back home

I want it like this before she comes back home

xHamster 1 year ago

Black Tgirls: Mistress Venom's Amazing Cumshot

62% HD 0:39 / 18:23

Black Tgirls: Mistress Venom's Amazing Cumshot

FapHouse 3 months ago

Duct Tape on My Mouth

HD 2:00 / 11:45

Duct Tape on My Mouth

Flirt4Free 6 months ago

Part 4:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

Part 4:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

xHamster 7 months ago

Sophia Loreen Party on Apr 6, 2026 - Part 2

51% HD 2:00 / 56:20

Sophia Loreen Party on Apr 6, 2026 - Part 2

Flirt4Free 2 months ago

Put Your Tongue into My Foreskin

61% HD 2:00 / 5:07

Put Your Tongue into My Foreskin

Flirt4Free 2 years ago

Fit shemale domina punishing a dude and fucking him in the ass

Fit shemale domina punishing a dude and fucking him in the ass

aShemaleTube 1 year ago

Liam Jacobson Private Show

50% HD 2:00 / 5:47

Liam Jacobson Private Show

Flirt4Free 1 year ago

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliation, Gapes.)

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliation, Gapes.)

Interracial 2 years ago

Maintenance spanking for Kitsy. Blowjob and sex following the punishment.

Maintenance spanking for Kitsy. Blowjob and sex following the punishment.

xHamster 3 years ago

Edlin Dockray Private Show

60% HD 2:00 / 13:31

Edlin Dockray Private Show

Flirt4Free 2 years ago

Subservient guy gets his wet asshole destroyed by the kinky tranny in hardcore bondage fuck

Subservient guy gets his wet asshole destroyed by the kinky tranny in hardcore bondage fuck

Tranny.one 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 weeks ago

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

HD 0:23 / 41:59

broke out of chastity and punished - ts gray perrier dominated by slayerxxx

PornBox 2 weeks ago

TS Natalie Mars fisted and stretched by MILF Penny Barber

TS Natalie Mars fisted and stretched by MILF Penny Barber

Fapcat 11 months ago

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