Punishment Videos (41,979)

Consequences for Breaking Out of Chastity

61% HD 1:01 / 42:05

Consequences for Breaking Out of Chastity

FapHouse 1 week ago

Sissy in Bondage Teased by Mistress

Sissy in Bondage Teased by Mistress

FapHouse 4 days ago

TSLALA DELUXXXBlack Man With Huge Penis Punishes Internal Ejaculation

TSLALA DELUXXXBlack Man With Huge Penis Punishes Internal Ejaculation

Eporner 6 days ago

Thai Transgender WomanFembabythwas Punished By Having Ejaculation Inside Her Anus

Thai Transgender WomanFembabythwas Punished By Having Ejaculation Inside Her Anus

Eporner 5 days 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

Chubby stepmom in stockings deepthroats before getting buttfucked

Chubby stepmom in stockings deepthroats before getting buttfucked

Some.Porn 2 years ago

This cute asian ladyboy needs a real hard punishement

This cute asian ladyboy needs a real hard punishement

Sheshaft 5 years ago

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Dirty cd tranny slut gets toyed by perverted police chick

Dirty cd tranny slut gets toyed by perverted police chick

Tranny.one 8 years ago

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

55% HD 0:39 / 28:08

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

FapHouse 2 months ago

Pegging GLASS EGGS!!

Premium HD 16:02

Pegging GLASS EGGS!!

XVideosRed 3 weeks ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

xHamster 1 month 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

Pink Latex Shebabe Punishes Her Bf

Pink Latex Shebabe Punishes Her Bf

Eporner 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 Deepthroat Challenge of the Gagging Reflex - Pig Pushes Its Limits

Extreme Deepthroat Challenge of the Gagging Reflex - Pig Pushes Its Limits

FapHouse 1 week ago

GERMAN BDSM - Mistress domina punish ugly guys painful

GERMAN BDSM - Mistress domina punish ugly guys painful

xHamster 3 years ago

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

47% HD 0:39 / 29:41

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

FapHouse 3 years 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 2 months ago

Active Booty

Premium 62% HD 39:44

TransAngels 8 years ago

Post Orgasm Fleshlight Milking

HD 0:39 / 18:00

Post Orgasm Fleshlight Milking

FapHouse 2 years ago

A Private Punishment

A Private Punishment

Tranny.one 4 years ago

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass

xHamster 6 months ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 9 months ago

Ultimate punishment for beta losers! Stop & Go masturbation to a pixel ass! Tranny JOI CEI

Ultimate punishment for beta losers! Stop & Go masturbation to a pixel ass! Tranny JOI CEI

xHamster 2 weeks 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

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

Hercules & Matt & Lance Private Show

HD 2:00 / 1:12:58

Hercules & Matt & Lance Private Show

Flirt4Free 3 years ago

Cute Maid's Lessons

Cute Maid's Lessons

Some.Porn 6 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

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

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

Sami - Femboy Punished by Futa for Spilling the Order

Sami - Femboy Punished by Futa for Spilling the Order

3DPornDude 1 week ago

TS Mistress Fucks Her Bound Male Slave

TS Mistress Fucks Her Bound Male Slave

Xozilla 4 days 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 3 days 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 2 weeks ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

57% HD 0:39 / 7:13

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

FapHouse 2 months ago

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

69% HD 1:01 / 19:41

She Is Going to Punish This Submissive Brat and Give Her a Red Ass

FapHouse 6 months ago

Cute Lie Ponce was completely delighted with her step-grandfather's thick cock.

Cute Lie Ponce was completely delighted with her step-grandfather's thick cock.

XGroovy 3 months 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

Sexy secretary talks about small in meeting room

Sexy secretary talks about small in meeting room

Some.Porn 2 years ago

Kitty Kunt and her huge she cock

Kitty Kunt and her huge she cock

xHamster 2 months 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

Skinny ts punished by BBC

Skinny ts punished by BBC

KeekAss 22 hours 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

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 1 week ago

The Sex Cafe 2

Some.Porn 6 months 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 1 week ago

TRANSFIXED - Sexy Ember Snow Craves Creampie After Ember Fieras Stunning Dress Reveal

TRANSFIXED - Sexy Ember Snow Craves Creampie After Ember Fieras Stunning Dress Reveal

Some.Porn 9 months ago

Punish Her

BeMyHole 3 days 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

$Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen$ 61% HD 2:00 / 27:28

Jhordy Gets Fucked and Enjoys Luccas\' Tasty Semen

Flirt4Free 9 months ago

cherry and i dominate our disobedient puppies nyxi and livi

58% HD 0:30 / 33:02

cherry and i dominate our disobedient puppies nyxi and livi

PornBox 1 year ago

Foot Torment Foot Jobs and TS Doctor Sex

Foot Torment Foot Jobs and TS Doctor Sex

xHamster 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

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

xHamster 3 months ago

Four shemale dominas fucks a guy with a mask and give him

Four shemale dominas fucks a guy with a mask and give him

xHamster 1 year ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 9 years ago

cuntwhipping stapler ache

cuntwhipping stapler ache

MatureTubeHere 5 years ago

Futa Anna Punishes the Submissive Burglar in Her House

Futa Anna Punishes the Submissive Burglar in Her House

3DPornDude 1 month ago

TS Larissa seduces the teacher and buggers him

TS Larissa seduces the teacher and buggers him

xHamster 1 year ago

Stiv Soul Private Show

Stiv Soul Private Show

Flirt4Free 3 years 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

Owen & Stivens & Patric Private Show

HD 2:00 / 23:20

Owen & Stivens & Patric Private Show

Flirt4Free 3 years 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

Matt & Oliver & Andres Private Show

64% HD 2:00 / 4:56

Matt & Oliver & Andres Private Show

Flirt4Free 3 years ago

Visceratio Gets Her Ass Punished - ShemaleDreamCams

Visceratio Gets Her Ass Punished - ShemaleDreamCams

Sheshaft 8 years ago

Pride and Orifice Part 2

Premium HD 30:35

Pride and Orifice Part 2

TransAngels 3 years ago

This Is How I Punish Myself When I Am Too Sorry

This Is How I Punish Myself When I Am Too Sorry

xHamster 9 months ago

SHEMALE DOMINATION - 95 - BARBARA PIRES & RICK BITCH - FULL VERSION - WMV

SHEMALE DOMINATION - 95 - BARBARA PIRES & RICK BITCH - FULL VERSION - WMV

Clips4sale 2 weeks 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

Booty trans Jessy Dubai punishes Ruckus and gives him BDSM session

Booty trans Jessy Dubai punishes Ruckus and gives him BDSM session

UrGayPorn 11 months ago

Threesome with bella

Threesome with bella

Tranny.one 4 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

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Latex TS sub chastity and butt fucking sex

Latex TS sub chastity and butt fucking sex

Analdin 1 week ago

Melaniie Moon Private Show

HD 2:00 / 50:49

Melaniie Moon Private Show

Flirt4Free 3 days 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

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

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 5 years ago

Andres & Hercules & Lian Private Show

64% HD 2:00 / 5:16

Andres & Hercules & Lian Private Show

Flirt4Free 3 years ago

Jose & Richard Private Show

53% HD 2:00 / 6:00

Jose & Richard Private Show

Flirt4Free 3 weeks ago

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

xHamster 6 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 1 week ago

Paul Walkers Private Show

Paul Walkers Private Show

Flirt4Free 1 week ago

Dimitri Caruso Private Show

4K 2:00 / 14:57

Dimitri Caruso Private Show

Flirt4Free 1 year ago

Patric & Oliver Private Show

48% HD 2:00 / 7:39

Patric & Oliver Private Show

Flirt4Free 3 years ago

Dom Fucks and Spank Delia Delions

Dom Fucks and Spank Delia Delions

xHamster 2 years ago

This roleplay will drop your jaw

62% HD 2:00 / 13:13

This roleplay will drop your jaw

Flirt4Free 7 years ago

$You Can\'t Stay Away from My Bulge and from My Dom Attitude$ 55% HD 2:00 / 22:20

You Can\'t Stay Away from My Bulge and from My Dom Attitude

Flirt4Free 3 years ago

Jose & Richard Private Show

Jose & Richard Private Show

Flirt4Free 3 weeks ago

Four shemale punishers in black leather outfits manhandle a

Four shemale punishers in black leather outfits manhandle a

xHamster 1 year ago

Athletic trans loves painal by bbc

Athletic trans loves painal by bbc

Sheshaft 3 months ago

Sarah Dark her Own Crossdressing Sissy

Sarah Dark her Own Crossdressing Sissy

its.PORN 7 years ago

a lot of punishment of ur fucking cock Clip 1

a lot of punishment of ur fucking cock Clip 1

xHamster 3 weeks ago

Eat My Fuckin Big Dick Ya Little Bitch-dom Show

50% HD 2:00 / 13:50

Eat My Fuckin Big Dick Ya Little Bitch-dom Show

Flirt4Free 7 years ago

Kennedy Rose Gets a Donut on her Butthole While Taking 2 Strap-ons

Kennedy Rose Gets a Donut on her Butthole While Taking 2 Strap-ons

Some.Porn 9 months ago

Danni Daniels Fucks Straight Couple in The Red Light Restricted Scene

Danni Daniels Fucks Straight Couple in The Red Light Restricted Scene

Pornicom 1 week ago

Sandy Nell Private Show

67% HD 2:00 / 4:19

Sandy Nell Private Show

Flirt4Free 4 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

Daphne Millerr Private Show

4K 2:00 / 21:09

Daphne Millerr Private Show

Flirt4Free 2 days ago

Huge Ass Trans Black Widow Wedgie and Ass Destroyed after Massive Anal Creampie and Cumfarts

Huge Ass Trans Black Widow Wedgie and Ass Destroyed after Massive Anal Creampie and Cumfarts

xHamster 1 month 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

TSDOMME: Straight Guy Bound and Punished

TSDOMME: Straight Guy Bound and Punished

xHamster 1 year ago

Sommer Kitty Private Show

HD 2:00 / 13:11

Sommer Kitty Private Show

Flirt4Free 1 year 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

Sophia Loreen Private Show

65% HD 2:00 / 6:21

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Mv – Shiri Allwood – Caught And Punished By Boyfriends Wife

Mv – Shiri Allwood – Caught And Punished By Boyfriends Wife

AbTranny 4 years ago

Femboy Raven Punishing her Puffy Teats and Lactating her Growing Breasts with Vacuum Machine

Femboy Raven Punishing her Puffy Teats and Lactating her Growing Breasts with Vacuum Machine

ShemaleSin 1 week ago

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

Yeswegays 1 year 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 2 days ago

secretary caught jerking off

66% HD 0:10 / 39:44

secretary caught jerking off

Clips4sale 2 years ago

Luccas & Jhordy & Master Private Show

56% HD 2:00 / 12:04

Luccas & Jhordy & Master Private Show

Flirt4Free 3 months ago

NAUGHTY VARIETY CAUGHT MASTURBATING

NAUGHTY VARIETY CAUGHT MASTURBATING

xnxxGold 8 months ago

PUNISHED IN PLACE #1 featuring Erin Everheart

Premium HD 21:31

PUNISHED IN PLACE #1 featuring Erin Everheart

XVideosRed 2 years ago

Corrine Dittmann Private Show

59% 4K 2:00 / 5:04

Corrine Dittmann Private Show

Flirt4Free 9 months ago

Big-titted MILF pounded by stunningTS

Big-titted MILF pounded by stunningTS

Some.Porn 9 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 1 month 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

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