Punishment Videos (26,210)

Tatiana & Owen Private Show

61% HD 2:00 / 6:44

Tatiana & Owen Private Show

Camster 1 month 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

Katty's Punishment

Katty's Punishment

Some.Porn 2 years ago

Trans Aubrey Kate face fucks and anal plows Pierce Paris

Trans Aubrey Kate face fucks and anal plows Pierce Paris

UrGayPorn 9 months ago

Trans Girl Worships His Trans Weenie In advance of He Wrecks Her Ass

Trans Girl Worships His Trans Weenie In advance of He Wrecks Her Ass

PornFreeNow 9 months ago

Slut Takes Double Anal Punishment DP, DAP, ATM Covered in Cum Facials

Slut Takes Double Anal Punishment DP, DAP, ATM Covered in Cum Facials

XHamster 5 months ago

Crossdresser slave

Crossdresser slave

Fetishpapa 4 years ago

Jose Castell Black Dominates with Whip 1

Jose Castell Black Dominates with Whip 1

XHamster 1 year ago

Lilit Hot Private Show

HD 2:00 / 15:12

Lilit Hot Private Show

Camster 5 days ago

NEW RIKA FOX! The BBC PUNISHER fucks Rika Fox! Full video available now subscribe 😈

NEW RIKA FOX! The BBC PUNISHER fucks Rika Fox! Full video available now subscribe 😈

AShemaleTube 1 year ago

Blonde White Femboy Milking her Nipples and Slapping them with Big Dildo

Blonde White Femboy Milking her Nipples and Slapping them with Big Dildo

XHamster 8 months ago

OBEDIENT CHINESE TRANNY ANAL INVASION AUDITION & MARIONETTE INSTRUCTING

OBEDIENT CHINESE TRANNY ANAL INVASION AUDITION & MARIONETTE INSTRUCTING

TrannyGem 1 month ago

femout - jill pill portland tranny xmas hardcore sex

femout - jill pill portland tranny xmas hardcore sex

TransDoe 2 years ago

Mop in the Ass of Sissy Katryn to Punish Her Negligence

Mop in the Ass of Sissy Katryn to Punish Her Negligence

XHamster 4 weeks ago

TRANSSEXUAL TORTURE - (Full Original Movie in HD Version)

TRANSSEXUAL TORTURE - (Full Original Movie in HD Version)

XHamster 4 years ago

Dani Saenz Private Show

HD 2:00 / 1:04:58

Dani Saenz Private Show

Camster 2 years ago

”Transgender Ryder Monroe bound fisted & screwed hard in AI punishment”

”Transgender Ryder Monroe bound fisted & screwed hard in AI punishment”

IFuckedYourGF 1 year ago

Naughty TS babe Lianna Lawson caged punished and fucked deep

Naughty TS babe Lianna Lawson caged punished and fucked deep

UrGayPorn 11 months ago

Cute Blonde Sissy Lactating her Tits and Spanking her Big Boobs with Black Cock

Cute Blonde Sissy Lactating her Tits and Spanking her Big Boobs with Black Cock

XHamster 7 months ago

Bbc Punishments

Bbc Punishments

Eporner 9 months ago

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

TS Delia DeLions punishes stepson and Siouxsie Q in spicy threesome

Fapcat 1 year ago

Caught walking her hotel and takes a huge cum load

Caught walking her hotel and takes a huge cum load

XHamster 2 months 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

lizzy laynez punished lizzy laines

lizzy laynez punished lizzy laines

PornOne 2 years ago

A sissy is punished for theft by having his ass fucked bareback

A sissy is punished for theft by having his ass fucked bareback

XXXShemalePorn 1 week ago

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

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

Trashreality 1 year ago

Hot shemale punisher in black fishnets gives a massive

Hot shemale punisher in black fishnets gives a massive

XHamster 2 years ago

Latex maid Lisa gets a good spanking and flogging from TGirl Mistress Lucy Clip 1

Latex maid Lisa gets a good spanking and flogging from TGirl Mistress Lucy Clip 1

XHamster 1 year ago

Lilit Hot Private Show

66% HD 2:00 / 7:40

Lilit Hot Private Show

Camster 2 weeks ago

Subby Gets Ass Punished by TS Sasha Blue

Subby Gets Ass Punished by TS Sasha Blue

XHamster 4 months ago

Open Your Mouth for Me..

Open Your Mouth for Me..

XHamster 2 months ago

Fucked and Punished by a Tran

Fucked and Punished by a Tran

AShemaleTube 13 years ago

Gabriella Bruni Private Show

64% 4K 2:00 / 5:46

Gabriella Bruni Private Show

Camster 10 months ago

FilthyPov - CAUGHT Sniffing Her Panties, Busty Stepmom Punished Me By Riding My Cock

FilthyPov - CAUGHT Sniffing Her Panties, Busty Stepmom Punished Me By Riding My Cock

Some.Porn 1 year ago

No189 Punishment for peeing

No189 Punishment for peeing

XHamster 5 months ago

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

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

PornBox 3 years ago

Ts Jessy Dubai Punishes Her Maid By Destrying Her Pussy

Ts Jessy Dubai Punishes Her Maid By Destrying Her Pussy

AShemaleTube 7 months ago

Nelly Gale Party on Sep 12, 2026 - Part 2

66% 4K 2:00 / 56:04

Nelly Gale Party on Sep 12, 2026 - Part 2

Camster 1 week ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

XHamster 4 months ago

Futanari - animatie Dimitrescu Punishes You

Futanari - animatie Dimitrescu Punishes You

Xfeed 5 months ago

Yasmin Lee In Ts Devastatingly Gorgeous Secretary Punishes Boss Ass

Yasmin Lee In Ts Devastatingly Gorgeous Secretary Punishes Boss Ass

AbTranny 9 months ago

My teenage fantasy.

My teenage fantasy.

Amateur8 1 month ago

Anitta's Addiction

Anitta's Addiction

Some.Porn 1 year 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

Honey FoXXX and Scout in Steamy Locker Room Encounter with College pornx Crush

Honey FoXXX and Scout in Steamy Locker Room Encounter with College pornx Crush

Pornicom 3 months ago

Avery Angel gets Punished #2

Avery Angel gets Punished #2

AShemaleTube 1 year ago

Goddess Venus Punishes Arrogant Boy Toy

Goddess Venus Punishes Arrogant Boy Toy

XHamster 1 year ago

Sissy Trans Anal Fuck with German Dominatrix

Sissy Trans Anal Fuck with German Dominatrix

Tranny.one 5 years ago

Hanna Ven Private Show

63% HD 2:00 / 9:04

Hanna Ven Private Show

Camster 2 years ago

Honey FoXXX and Scout in Steamy Locker Room Encounter with College -Censored- Crush

Honey FoXXX and Scout in Steamy Locker Room Encounter with College -Censored- Crush

Sheshaft 4 months ago

”Transgender in chastity punished & anal fucked”

”Transgender in chastity punished & anal fucked”

ThePornstar 1 year ago

OUT OF THE FAMILY - HOTTEST INTERRACIAL COMPILATION! STEPDAUGHTER, TEEN, PETITE, AND MORE!

OUT OF THE FAMILY - HOTTEST INTERRACIAL COMPILATION! STEPDAUGHTER, TEEN, PETITE, AND MORE!

Some.Porn 2 years ago

Doc punishing his bratty submissive femboy sissy Michele

Doc punishing his bratty submissive femboy sissy Michele

XHamster 4 years ago

Transgender Princess Punishers Raunchy up Man Plaything Evelin Rangel , Bruna Castro

Transgender Princess Punishers Raunchy up Man Plaything Evelin Rangel , Bruna Castro

TrannyGem 5 years ago

Latex TS Queens Dominate Their Subs

Latex TS Queens Dominate Their Subs

Xozilla 3 months ago

Punished For Skipping Chores - 1/2 - Spanked And Paddled

Punished For Skipping Chores - 1/2 - Spanked And Paddled

AbTranny 4 years ago

Drake Von punishes Khloe Kay for seducing his girlfriend

Drake Von punishes Khloe Kay for seducing his girlfriend

WeGotDicks 6 months 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

Nelly Gale Private Show

4K 2:00 / 16:28

Nelly Gale Private Show

Camster 1 week ago

Angellica Good and Rana Katana roll out colorful mats and start doing yoga together

Angellica Good and Rana Katana roll out colorful mats and start doing yoga together

Yeswegays 1 year ago

Punishment Transexual (Full porn movie)

Punishment Transexual (Full porn movie)

XHamster 11 months ago

Spoiled and Happy on Mothers' Day

Spoiled and Happy on Mothers' Day

Some.Porn 11 months ago

”Charlie Patterson is banging his trans prof Kayleigh Coxx”

”Charlie Patterson is banging his trans prof Kayleigh Coxx”

Rainblow 2 years ago

Lisan & Mine Private Show

Lisan & Mine Private Show

Camster 1 day 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

Sophia Loreen Private Show

4K 2:00 / 26:08

Sophia Loreen Private Show

Camster 1 year ago

Chocolate Fill Play with My Sissy Gurlfriend Part 1

Chocolate Fill Play with My Sissy Gurlfriend Part 1

XHamster 8 months ago

TS Vaniity Dominates Boy Rick Monroe Anal Fuck And Face Fucking For Intense Cum Swap

TS Vaniity Dominates Boy Rick Monroe Anal Fuck And Face Fucking For Intense Cum Swap

Sheshaft 8 months ago

”Gagged hoe toyed & screwed in public”

”Gagged hoe toyed & screwed in public”

TransHero 9 months ago

Trans army gets punished by sergeant

Trans army gets punished by sergeant

AShemaleTube 1 day ago

Sandy Lee Private Show

Sandy Lee Private Show

Camster 10 years ago

The Vandal

Some.Porn 2 years ago

Submissive bloke gets his ass destroyed by the horny TS babe

Submissive bloke gets his ass destroyed by the horny TS babe

Tranny.one 4 years ago

Kai Bailey's Threesome Delight: Submissive Trans Bambi Bliss Takes Two Hard Cocks

Kai Bailey's Threesome Delight: Submissive Trans Bambi Bliss Takes Two Hard Cocks

BallsNBoobs 7 months ago

Crossdresser boyfriend is fucked by dominatrix with strapon

Crossdresser boyfriend is fucked by dominatrix with strapon

XGroovy 3 years ago

Nettles chastity torture

Nettles chastity torture

XHamster 3 years ago

TS Shiri Bangs Him Until Self Facial

TS Shiri Bangs Him Until Self Facial

ShemaleSin 4 years ago

Costumed Pornstar Plays A Game With TS

Costumed Pornstar Plays A Game With TS

Fetishpapa 1 week ago

”Nutty : Bareback Punishment”

”Nutty : Bareback Punishment”

TransHero 6 years ago

a trans policewoman punishes the thief

a trans policewoman punishes the thief

PornBox 4 years ago

Mistress Korra Punishes Naughty With Korra Del Rio

Mistress Korra Punishes Naughty With Korra Del Rio

AbTranny 3 years ago

Kinky shemale chick dressed as police punishes the guy with a hardcore anal pounding

Kinky shemale chick dressed as police punishes the guy with a hardcore anal pounding

BeMyHole 3 years ago

winter bluu sock wrestling loser gets punished

winter bluu sock wrestling loser gets punished

AShemaleTube 4 years ago

”Tatted babe punishes Girlfriend for cheating”

”Tatted babe punishes Girlfriend for cheating”

TransHero 9 months ago

Keoki Star dominates and punishes petite girl in hot BDSM fetish scene without condom

Keoki Star dominates and punishes petite girl in hot BDSM fetish scene without condom

TrannyMovs 3 months 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

No mercy PEGGING for CHASTITY slave

No mercy PEGGING for CHASTITY slave

XHamster 1 year ago

Claire Punishment Fucking her self again

Claire Punishment Fucking her self again

AShemaleTube 1 month ago

”The Asian Nanny Lulu Chu Needs Discipline”

”The Asian Nanny Lulu Chu Needs Discipline”

TransHero 9 months ago

FTM Puppy Gets Wedgie and Locked in a Cell

FTM Puppy Gets Wedgie and Locked in a Cell

TransTube.tv 1 year ago

Humiliating BF gets her punishment by his shemale GF

Humiliating BF gets her punishment by his shemale GF

Fapnado 5 years ago

Edging Masturbation with Post Climax Punishment

Edging Masturbation with Post Climax Punishment

ShemaleSin 3 months ago

Punishment Edging with Cockcage

Punishment Edging with Cockcage

AShemaleTube 1 month ago

Lika Kai Private Show

Lika Kai Private Show

Camster 1 week ago

Big Tits Femboy Ben Tennyson Lactating and Pumping her Puffy Nipples with Vacuum Milking Machine Clip 2

Big Tits Femboy Ben Tennyson Lactating and Pumping her Puffy Nipples with Vacuum Milking Machine Clip 2

XHamster 2 months ago

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

Top 10 Sissy Ideas 2023 (pegging, Butt Plugs, Piss, Chastity, Diapers, Enema)

XHamster 1 year ago

Ladyboy Amy Punished Bareback

Ladyboy Amy Punished Bareback

Sheshaft 9 years ago

Top 10 ideas for sissification - big compilation

Top 10 ideas for sissification - big compilation

XCafe 1 year ago

The Reward for the Locked-up Sissy

The Reward for the Locked-up Sissy

XHamster 10 months ago

Sophia Loreen Private Show

56% 4K 2:00 / 8:29

Sophia Loreen Private Show

Camster 1 week ago

Pretty Bella Fucked Nicely

Pretty Bella Fucked Nicely

Some.Porn 1 year ago

Bad ladyboy punished for cheating

Bad ladyboy punished for cheating

Sheshaft 2 years ago

cuntwhipping stapler ache

cuntwhipping stapler ache

MatureTubeHere 5 years ago

Too Quickly Cumshot and Punished After Orgasm

Too Quickly Cumshot and Punished After Orgasm

XHamster 5 months ago

Tgirl Sissy Slut Anal Dildo Punishment

Tgirl Sissy Slut Anal Dildo Punishment

AShemaleTube 8 years ago

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

XHamster 6 months ago

Doing Life and Your Wife

Doing Life and Your Wife

Some.Porn 2 years ago

Cock sounding punishment for pitiful slaves in group session

Cock sounding punishment for pitiful slaves in group session

PornLib 7 months ago

Sub Shemale Drilled Coarse by Dom

Sub Shemale Drilled Coarse by Dom

ShemaleSin 5 years ago

Shemale mistress loves punishing her slave boy

Shemale mistress loves punishing her slave boy

Fapcat 4 months 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 4 months ago

”Please punish me professor for being bad”

”Please punish me professor for being bad”

TransHero 9 months ago

The League of Extraordinary Transsexuals: Part 1 Super Hero Feature

The League of Extraordinary Transsexuals: Part 1 Super Hero Feature

AShemaleTube 6 days ago

Staying in: Chelsea Marie Punishes Girlfriend Cherry Torn

Staying in: Chelsea Marie Punishes Girlfriend Cherry Torn

ShemaleSin 9 months ago

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

Xshemale 2 years ago

crossdresser punishment

crossdresser punishment

AShemaleTube 4 years ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

XHamster 11 months ago

Lika Kai Private Show

59% 4K 2:00 / 4:26

Lika Kai Private Show

Camster 2 months ago

Japanese MILF Anal - Rough Deep Creampie Punishment Shemale

Japanese MILF Anal - Rough Deep Creampie Punishment Shemale

POVJP 1 year 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 5 months ago

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