Punishment Videos (40,574)

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

HD 0:39 / 52:10

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

FapHouse 1 week ago

Hot Trans Sabrina gets her punishment after fucking my partner.

Hot Trans Sabrina gets her punishment after fucking my partner.

XVideosRed 4 months ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 1 month ago

Female Director Haruna's Amateur Lesbian Picking Up Girls 110 Friends And Tsubaki Kato Punishment First Lesbian 3P Iki Rolling Punishment Game! Intro

Female Director Haruna's Amateur Lesbian Picking Up Girls 110 Friends And Tsubaki Kato Punishment First Lesbian 3P Iki Rolling Punishment Game! Intro

Bokep.PORN 2 weeks ago

Archie Blossom Private Show

57% HD 2:00 / 16:54

Archie Blossom Private Show

Flirt4Free 1 month ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

xHamster 3 months ago

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Goddess Cherry Punishes My Slutty Holes

63% HD 1:01 / 23:44

Goddess Cherry Punishes My Slutty Holes

FapHouse 2 years ago

This Town Ain't Big Enough for the Two of Us: Futa Sheriff Gives Criminal Rough Punishment Pegging

This Town Ain't Big Enough for the Two of Us: Futa Sheriff Gives Criminal Rough Punishment Pegging

xHamster 3 months ago

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 3

66% HD 2:00 / 9:54

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 3

Flirt4Free 2 days ago

Busty trans Daisty Taylor gets dominated

Busty trans Daisty Taylor gets dominated

PornDR 3 years ago

Roommate Feminized and Fucked for Punishment

Roommate Feminized and Fucked for Punishment

xHamster 2 months ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

xHamster 1 month ago

The Papi Chulo BBC Fisted Me Deep Until I Came

The Papi Chulo BBC Fisted Me Deep Until I Came

xHamster 1 month ago

Heat Gel Pt.3

51% 1:00 / 29:29

Hentaied.Pro 3 days 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 4 months ago

”Black tbabe step mom rimmed & banged hard by Nick”

”Black tbabe step mom rimmed & banged hard by Nick”

4Wank 2 years ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 2 months ago

Matt & Oliver & Andres Private Show

63% HD 2:00 / 7:43

Matt & Oliver & Andres Private Show

Flirt4Free 3 years ago

from cheater to sissy: punishment pegging from futa mommy

55% HD 0:10 / 13:09

from cheater to sissy: punishment pegging from futa mommy

LoyalFans 2 years ago

a lot of punishment of ur fucking cock

a lot of punishment of ur fucking cock

xHamster 3 weeks ago

Trans Beauty Worships His Trans Penis Previous to This guy Wrecks Her Butt

Trans Beauty Worships His Trans Penis Previous to This guy Wrecks Her Butt

BigTitsLust 4 months 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 4 years ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

xHamster 3 months ago

Verbal Domination, Making Fun of His Nickname and His Existance

55% HD 2:00 / 4:02

Verbal Domination, Making Fun of His Nickname and His Existance

Flirt4Free 7 months ago

Mary & Polly Private Show

4K 2:00 / 15:21

Mary & Polly Private Show

Flirt4Free 8 months ago

For Your Boy Pussy Ashley Sinclair

69% HD 1:01 / 5:13

For Your Boy Pussy Ashley Sinclair

FapHouse 3 days ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 3 years ago

Tall redhead shemale punishing a dude's asshole

Tall redhead shemale punishing a dude's asshole

aShemaleTube 1 month ago

Busty tranny takes over after stud is done fucking his petite GF

Busty tranny takes over after stud is done fucking his petite GF

Katestube 1 year ago

A Dominant Granny Trains These Little Whores

63% 1:01 / 42:07

A Dominant Granny Trains These Little Whores

FapHouse 6 months ago

The Most beautiful Trans Tits in the World Pinched and Lactating

The Most beautiful Trans Tits in the World Pinched and Lactating

xHamster 4 months ago

Darksome skin transsexual punisher screws a chap in servitude and cums

Darksome skin transsexual punisher screws a chap in servitude and cums

ShemaleSin 2 years ago

Nelly Gale Private Show

4K 2:00 / 11:36

Nelly Gale Private Show

Flirt4Free 2 days ago

Sophia Loreen Private Show

48% HD 2:00 / 10:53

Sophia Loreen Private Show

Flirt4Free 3 years ago

Bondman dominates and punishes with rough bareback fucking and cumshots

Bondman dominates and punishes with rough bareback fucking and cumshots

TrannyMovs 1 week 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 3 months ago

Alejandra & Hellen Private Show

HD 2:00 / 11:27

Alejandra & Hellen Private Show

Flirt4Free 2 years ago

KachuaLeFreak dominates and punishes her sissy playmate with hardcore BDSM

KachuaLeFreak dominates and punishes her sissy playmate with hardcore BDSM

GayVD 1 week ago

Jacob Malik Private Show

60% HD 2:00 / 8:46

Jacob Malik Private Show

Flirt4Free 1 month ago

Katy Ling Private Show

Katy Ling Private Show

Flirt4Free 1 week ago

”Titty mature STEPMOM punishes naughty TS & Latin with strapon”

”Titty mature STEPMOM punishes naughty TS & Latin with strapon”

Zatube 2 weeks ago

Bia Bastos dominates and punishes her hesitating GF with a hardcore handjob and more

Bia Bastos dominates and punishes her hesitating GF with a hardcore handjob and more

TrannyMovs 5 days ago

Wicked family games two

Wicked family games two

MatureTubeHere 5 years ago

Troy Khalil Private Show

HD 2:00 / 18:10

Troy Khalil Private Show

Flirt4Free 2 years ago

Fuck Me with Big Toy and Make Made Squirt

HD 2:00 / 13:58

Fuck Me with Big Toy and Make Made Squirt

Flirt4Free 1 year ago

Sissy tgirl rough anal

Sissy tgirl rough anal

Fetishpapa 8 years ago

cum show

56% HD 2:00 / 7:48

Flirt4Free 4 years ago

Jepsen Rae Private Show

HD 2:00 / 16:18

Jepsen Rae Private Show

Flirt4Free 2 weeks ago

Threesome with bella

Threesome with bella

Tranny.one 4 years ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

aShemaleTube 1 week ago

”Sexy Mommy Transgender punishing naughty hubby”

”Sexy Mommy Transgender punishing naughty hubby”

TransHero 2 years ago

Black Tgirls: Mistress Venom's Amazing Cumshot

63% HD 0:39 / 18:23

Black Tgirls: Mistress Venom's Amazing Cumshot

FapHouse 1 month ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 7 months ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

Dionisio & Perseo & Elvis Private Show

53% HD 2:00 / 30:47

Dionisio & Perseo & Elvis Private Show

Flirt4Free 3 years ago

Sophia Loreen Private Show

64% HD 2:00 / 18:04

Sophia Loreen Private Show

Flirt4Free 2 days ago

Joanna Jet dominates and punishes her student Sarah Vandella with a rough deepthroat and rimming session

Joanna Jet dominates and punishes her student Sarah Vandella with a rough deepthroat and rimming session

Pornicom 5 months 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 9 months ago

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

Big Tits Shemale Gwen Tennyson Lactating Her Nipples with Vacuum Milking Machine

xHamster 2 weeks ago

kinktestshoots - tori easton and rodrigo amor bound for delivery transgirl on male

kinktestshoots - tori easton and rodrigo amor bound for delivery transgirl on male

TransDoe 2 years ago

Sophia Loreen Party on Apr 17, 2026 - Part 3

HD 2:00 / 24:33

Sophia Loreen Party on Apr 17, 2026 - Part 3

Flirt4Free 2 days ago

Master & Ithan & Aleex Private Show

38% HD 2:00 / 33:20

Master & Ithan & Aleex Private Show

Flirt4Free 9 months ago

Brunette shemale punisher spanks and fucks her lover outdoors

Brunette shemale punisher spanks and fucks her lover outdoors

aShemaleTube 1 year ago

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

Rainblow 9 months ago

King Noire Fucks Pixi Lust Tiny Asshole

King Noire Fucks Pixi Lust Tiny Asshole

Analdin 1 week ago

Jenny Demian Private Show

HD 2:00 / 15:31

Jenny Demian Private Show

Flirt4Free 4 months ago

Liam Jacobson Private Show

61% HD 2:00 / 14:42

Liam Jacobson Private Show

Flirt4Free 1 year ago

Viky & Master Private Show

57% HD 2:00 / 14:39

Viky & Master Private Show

Flirt4Free 8 months ago

Doe Cosplay | Masturbation Without Panties

Doe Cosplay | Masturbation Without Panties

Flirt4Free 4 months ago

squirt - Part 2

63% 4K 2:00 / 9:52

squirt - Part 2

Flirt4Free 10 months ago

”SARINAANDROBIN - GODDESS CHERRY PUNISHES MY SLUTTY HOLES”

”SARINAANDROBIN - GODDESS CHERRY PUNISHES MY SLUTTY HOLES”

Fapnow 3 weeks ago

Doc punishing his bratty submissive femboy sissy Michele

Doc punishing his bratty submissive femboy sissy Michele

xHamster 3 years ago

Cock Head Burning Punishment

51% HD 1:01 / 6:01

Cock Head Burning Punishment

FapHouse 2 years ago

Jasmin Keur & Rick Fix Private Show

HD 2:00 / 15:11

Jasmin Keur & Rick Fix Private Show

Flirt4Free 1 year ago

Sold As a Slave by Roman Soldiers

54% HD 2:00 / 9:30

Sold As a Slave by Roman Soldiers

Flirt4Free 1 year ago

Submissive in an Electrified Cage - Punishment Under Needles

63% 0:39 / 8:18

Submissive in an Electrified Cage - Punishment Under Needles

FapHouse 1 week ago

Liam Jacobson Members-Only Show - Part 2

61% HD 2:00 / 36:43

Liam Jacobson Members-Only Show - Part 2

Flirt4Free 1 year ago

Busted Watching Porn at Work Boss Punishes Bad Employee w Her Own Cock

Busted Watching Porn at Work Boss Punishes Bad Employee w Her Own Cock

Xshemale 11 years ago

Jessica Host One Night Stand

61% HD 0:39 / 35:34

Jessica Host One Night Stand

FapHouse 9 months ago

Patric & Alexander & Lian Private Show

48% HD 2:00 / 38:16

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Introducing Kinky TS Kitty Kat

66% 0:39 / 14:21

Introducing Kinky TS Kitty Kat

FapHouse 1 year ago

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliat

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliat

PornoXO 1 year ago

Tranny ass fucking fucks stocked male

Tranny ass fucking fucks stocked male

Analdin 2 weeks ago

Domme Mercer Latex Sissy Punished by Chastity, Fuckmachine, Slapping, Dicksucking, and Pegging

Domme Mercer Latex Sissy Punished by Chastity, Fuckmachine, Slapping, Dicksucking, and Pegging

TransTube.tv 1 year ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Katy Ling Private Show

HD 2:00 / 26:16

Katy Ling Private Show

Flirt4Free 5 days ago

Liam Jacobson Private Show

62% HD 2:00 / 8:02

Liam Jacobson Private Show

Flirt4Free 1 year ago

Pietra Mancini and friend break and use up the slave, fistin and fuckin

Pietra Mancini and friend break and use up the slave, fistin and fuckin

aShemaleTube 5 months ago

Izzy Wilde tells stepbro she has a cock and gets anal punishment

Izzy Wilde tells stepbro she has a cock and gets anal punishment

AnySex 3 years ago

I'm Angry with You, My Boy! as a Punishment, You Punch Yourself While Jerking off! JOI CBT German

I'm Angry with You, My Boy! as a Punishment, You Punch Yourself While Jerking off! JOI CBT German

FapHouse 2 months ago

Naughty Boy's Get Punished

Naughty Boy's Get Punished

xHamster 3 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 4 months ago

Sophia Loreen Strip

55% HD 2:00 / 4:00

Sophia Loreen Strip

Flirt4Free 3 years ago

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

HD 0:39 / 49:41

The Naughty Nun: Korra Del Rio Punishes Disgraceful Sinner Dj

FapHouse 5 months ago

King Noire Fucks Pixi Lust Tiny Asshole

King Noire Fucks Pixi Lust Tiny Asshole

GayVids 2 months ago

Orianna Dunn Private Show

51% HD 2:00 / 12:27

Orianna Dunn Private Show

Flirt4Free 2 years ago

Welcome to Paradise Side of Prison

47% HD 0:39 / 6:27

Welcome to Paradise Side of Prison

FapHouse 3 months ago

Trans Stepmommy JOI CEI Cum, Anal Milk & Creampie PoV

Trans Stepmommy JOI CEI Cum, Anal Milk & Creampie PoV

xHamster 3 weeks ago

TS Foxxy Punishes Slob Boyfriend with Drubbing & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Drubbing & Nonstop Pounding!

ShemaleSin 1 week ago

t-model Punishers coarse Up fellow plaything Evelin Rangel Bruna Castro

t-model Punishers coarse Up fellow plaything Evelin Rangel Bruna Castro

Transvids.tv 1 year ago

”Stepmum Skylar Snow demands satisfaction!”

”Stepmum Skylar Snow demands satisfaction!”

TransHero 4 months ago

Camila Grant Private Show

Camila Grant Private Show

Flirt4Free 4 days ago

Executioners

Some.Porn 10 months ago

Sissy Trans Whore Servs Owner as BDSM Sex Slave Got Dominated Deepthroated Faceslaped During Football Punished Humiliation

58% HD 1:01 / 50:47

Sissy Trans Whore Servs Owner as BDSM Sex Slave Got Dominated Deepthroated Faceslaped During Football Punished Humiliation

FapHouse 10 months ago

Schwangere holt sich Callboy

Schwangere holt sich Callboy

Tranny.one 4 years ago

Colombian Boys Private Show

HD 2:00 / 23:35

Colombian Boys Private Show

Flirt4Free 2 years ago

ride dildo

53% HD 2:00 / 6:53

Flirt4Free 4 years ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 3 months ago

Freak of Nature 38 Older SADOMASOCHISM

Freak of Nature 38 Older SADOMASOCHISM

MatureTubeHere 5 years ago

Bound and Restrained: 2 Masters Pleasure and Punish Slave

Bound and Restrained: 2 Masters Pleasure and Punish Slave

SexTubeSpot 8 years ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 3 months 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 4 months ago

Head Mistress Fucks and Milks Handcuffed Trans Nun

Head Mistress Fucks and Milks Handcuffed Trans Nun

FapHouse 1 year ago

Archie Blossom Private Show

HD 2:00 / 14:11

Archie Blossom Private Show

Flirt4Free 1 week 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

Charlie Cano Private Show

46% HD 2:00 / 5:58

Charlie Cano Private Show

Flirt4Free 3 years ago

Luccas & Archie & Jose Private Show

63% HD 2:00 / 52:50

Luccas & Archie & Jose Private Show

Flirt4Free 2 months ago

Wild Sabrina Private Show

49% HD 2:00 / 16:26

Wild Sabrina Private Show

Flirt4Free 6 years ago

Big Booty TS Esther gets fucked by the BBC PUNISHER and Facialed

Big Booty TS Esther gets fucked by the BBC PUNISHER and Facialed

aShemaleTube 1 month ago

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