Punishment Videos (58,550)

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

Part 1:- Lanista Bear and Maid Jayne Has a Treat in the Library

Part 1:- Lanista Bear and Maid Jayne Has a Treat in the Library

FapHouse 1 week ago

Peeper's Punishment: TS Foxxy Takes Down Peeping Tom

65% HD 0:39 / 33:08

Peeper's Punishment: TS Foxxy Takes Down Peeping Tom

FapHouse 3 months ago

Sophia Loreen Party on Jun 23, 2026 - Part 4

64% HD 2:00 / 35:23

Sophia Loreen Party on Jun 23, 2026 - Part 4

Camster 1 week ago

Little brat Emmy Angels is cheeky to Domme Peggy DeVille, who happens to be holding all the impact toys.... so her butt, clitty and tits are punished.

57% HD 0:10 / 19:36

Little brat Emmy Angels is cheeky to Domme Peggy DeVille, who happens to be holding all the impact toys.... so her butt, clitty and tits are punished.

LoyalFans 7 months ago

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Veggiebabyy - You Forgot Vday Futa Punishment Pegging

Nuvid 2 years ago

Danielle Punish Curieuse Skater Boy

Danielle Punish Curieuse Skater Boy

Eporner 3 days ago

Chastity Doll Pounded in Chastity by Femdom

HD 0:10 / 28:13

Chastity Doll Pounded in Chastity by Femdom

LoyalFans 1 week ago

Adding You to My Ass: Tiny Becomes Part of a Giantess

HD 0:39 / 11:02

Adding You to My Ass: Tiny Becomes Part of a Giantess

FapHouse 1 month ago

Crossdresser Valerie Cums Hard in Nylon Stockings

Crossdresser Valerie Cums Hard in Nylon Stockings

WebcamBros 1 week ago

Sophia Loreen Private Show

HD 2:00 / 15:51

Sophia Loreen Private Show

Camster 1 week ago

Jennifer Skanes Private Show

HD 2:00 / 19:49

Jennifer Skanes Private Show

Camster 1 week ago

Your Favorite Distraction

Your Favorite Distraction

Camster 3 weeks 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

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

HD 1:01 / 21:15

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

FapHouse 3 days ago

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

HD 0:39 / 16:23

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

FapHouse 1 week ago

Mistress Trap Punishment

Mistress Trap Punishment

aShemaleTube 10 months ago

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

49% HD 0:39 / 13:12

Jessie Shrinks Her Tiny & Crushes Him with Her Monster Cock

FapHouse 4 months ago

Roommate Feminized and Fucked for Punishment

Roommate Feminized and Fucked for Punishment

xHamster 5 months ago

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

Chastity Christmas! Naughty tranny girl gets punished! Spanking! Mouthfuck! Assfuck!

xHamster 5 months ago

Futa Anna Punishes the Submissive Burglar in Her House

Futa Anna Punishes the Submissive Burglar in Her House

3DPornDude 2 months ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 1 year ago

ride dildo

55% HD 2:00 / 6:53

Flirt4Free 4 years ago

futa step-sis makes you her slave- punishment painal, slapping, spitting

HD 0:30 / 21:03

futa step-sis makes you her slave- punishment painal, slapping, spitting

IWantClips 3 years ago

Ryan Boness & Eduar Senni Private Show

59% HD 2:00 / 4:57

Ryan Boness & Eduar Senni Private Show

Flirt4Free 3 weeks ago

A Private Punishment

A Private Punishment

Tranny.one 4 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 10 months ago

Maya Spring Private Show

Maya Spring Private Show

Camster 1 week ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

63% HD 0:39 / 52:10

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

FapHouse 2 months 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

Jhordy & Maxx Private Show

46% HD 2:00 / 1:47:48

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

Xoxo da punisher

Xoxo da punisher

KeekAss 4 years ago

Sophia Loreen Private Show

HD 2:00 / 18:12

Sophia Loreen Private Show

Flirt4Free 1 week ago

Trans Doll Housewife Punishes Peeping Tom

Trans Doll Housewife Punishes Peeping Tom

Eporner 5 days ago

Sophia Loreen Party on Apr 18, 2026 - Part 3

53% HD 2:00 / 33:08

Sophia Loreen Party on Apr 18, 2026 - Part 3

Flirt4Free 2 months 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 5 months ago

Kitty Kunt and her huge she cock

Kitty Kunt and her huge she cock

xHamster 3 months ago

Busty Shemale Punishes Dude in Black Mask

Busty Shemale Punishes Dude in Black Mask

BeMyHole 1 year ago

Izzi Private Show

Izzi Private Show

Flirt4Free 5 days ago

PUNISHMENT

aShemaleTube 8 months ago

Venezuelan friend with good cock of 23cm eating chicken ass Bogota

Venezuelan friend with good cock of 23cm eating chicken ass Bogota

xHamster 2 weeks ago

Ambar & Lord Private Show

Ambar & Lord Private Show

Camster 6 days ago

Master & Ithan Private Show

54% HD 2:00 / 9:40

Master & Ithan Private Show

Flirt4Free 1 year ago

Petite Goth Girl Gets Ragdolled Sweet & Rough by Slavemaster Shemale and Takes Her Load

Petite Goth Girl Gets Ragdolled Sweet & Rough by Slavemaster Shemale and Takes Her Load

Dafreeporn 1 week ago

Sophia Loreen Private Show

HD 2:00 / 22:54

Sophia Loreen Private Show

Camster 5 days ago

shemale wearing a bdsm mask and asuka cosplay stretches her nipples and punishes her breasts with a vacuum machine until they lactate

56% HD 0:30 / 15:58

shemale wearing a bdsm mask and asuka cosplay stretches her nipples and punishes her breasts with a vacuum machine until they lactate

PornBox 6 months ago

Tommy & Master Private Show

Tommy & Master Private Show

Flirt4Free 3 months ago

Patric & Oliver Private Show

63% HD 2:00 / 14:54

Patric & Oliver Private Show

Flirt4Free 3 years ago

step-mommy punishes gamer girl nyxi

HD 0:30 / 11:47

step-mommy punishes gamer girl nyxi

PornBox 4 weeks ago

Angel Joseph Private Show

HD 2:00 / 26:57

Angel Joseph Private Show

Flirt4Free 4 months ago

Latex Domination and Sissy Training

Latex Domination and Sissy Training

TransTube.tv 1 week ago

Dani Saenz Private Show

HD 2:00 / 12:31

Dani Saenz Private Show

Camster 4 years ago

Patric & Simon & Frederick Private Show

55% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 2 years ago

Jacob Malik Private Show

62% HD 2:00 / 4:28

Jacob Malik Private Show

Flirt4Free 4 months ago

Ball-gagged slut gets tied up and punished with toys, deepthroats and blowjobs by a sissy crossdresser

Ball-gagged slut gets tied up and punished with toys, deepthroats and blowjobs by a sissy crossdresser

TrannyMovs 1 week ago

Victoria Rousso Private Show

HD 2:00 / 15:14

Victoria Rousso Private Show

Flirt4Free 3 years ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

Lanna & Nefertiti Private Show

64% HD 2:00 / 5:57

Lanna & Nefertiti Private Show

Flirt4Free 3 years ago

India new sexx girls happy moment

India new sexx girls happy moment

xHamster 1 year ago

Japanese Shemale Fucks Female - Niko Suzune & Nozomi Arimura

Japanese Shemale Fucks Female - Niko Suzune & Nozomi Arimura

Eporner 9 months ago

Bossy Dillon Stone punishes lazy FTM Joey Michaels with her thick pussy

Bossy Dillon Stone punishes lazy FTM Joey Michaels with her thick pussy

MenGem 1 year ago

Hottie Harmony

Some.Porn 1 year 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 10 months ago

Jhordy & Maxx Private Show

69% HD 2:00 / 5:03

Jhordy & Maxx Private Show

Flirt4Free 10 months ago

Nerdy transgirl in tight suit has failed the no nut november and drinks her own as punishment

Nerdy transgirl in tight suit has failed the no nut november and drinks her own as punishment

xHamster 1 year ago

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

65% 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 7 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 month ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 1 week ago

Are You Ready to Please Your Mistress

Are You Ready to Please Your Mistress

xHamster 5 months ago

Topping Emma Rose

42% HD 0:10 / 20:34

Topping Emma Rose

LoyalFans 5 months ago

Shemale Yanka And Kimberlly Dirty Stinky Farting Punishment V

Shemale Yanka And Kimberlly Dirty Stinky Farting Punishment V

Clips4sale 5 months ago

Black Tgirls: Mistress Venom's Amazing Cumshot

54% HD 0:39 / 18:23

Black Tgirls: Mistress Venom's Amazing Cumshot

FapHouse 3 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Paulo & Jose & Sander Private Show

64% HD 2:00 / 11:56

Paulo & Jose & Sander Private Show

Flirt4Free 3 weeks ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 6 days ago

Cock torture with toothpaste day 2

Cock torture with toothpaste day 2

xHamster 2 years ago

YesFather: Mason Anderson amongst Parent Fiore punished

YesFather: Mason Anderson amongst Parent Fiore punished

Gay4Porn 4 years ago

Bitch caught watching tranny porn and masturbating alone, she must be punished now

Bitch caught watching tranny porn and masturbating alone, she must be punished now

xHamster 5 months ago

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

BeMyHole 6 years ago

Takes Parker To A Secret Dungeon, Punishes And Fucks Him With Sarina Valentina

Takes Parker To A Secret Dungeon, Punishes And Fucks Him With Sarina Valentina

AbTranny 9 months ago

Lucy Hart Makes me SO Heavy at SweetFemdom

Lucy Hart Makes me SO Heavy at SweetFemdom

xHamster 4 weeks ago

Cross Training LaSirena

Cross Training LaSirena

Some.Porn 8 months ago

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

61% HD 1:01 / 28:08

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

FapHouse 3 months ago

Sissy selfbondage tied in abandoned attic

Sissy selfbondage tied in abandoned attic

xHamster 11 months ago

The Papi Chulo BBC Fisted Me Deep Until I Came

The Papi Chulo BBC Fisted Me Deep Until I Came

xHamster 3 months ago

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

61% HD 1:01 / 29:41

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

FapHouse 3 years ago

Exciting Trans Vaniity Mia Isabella Pound

Exciting Trans Vaniity Mia Isabella Pound

Analdin 1 month ago

Sophia Loreen Party on Jun 9, 2026 - Part 3

HD 2:00 / 1:07:26

Sophia Loreen Party on Jun 9, 2026 - Part 3

Flirt4Free 3 weeks ago

Honey Shemale Locker Room Jerk Off

Honey Shemale Locker Room Jerk Off

Yeswegays 3 months ago

The teacher wants the cock of the young TS Larissa

The teacher wants the cock of the young TS Larissa

xHamster 4 years ago

Pride and Orifice Part 2

Premium HD 30:35

Pride and Orifice Part 2

TransAngels 3 years ago

Sophia Loreen Private Show - Part 2

57% HD 2:00 / 10:36

Sophia Loreen Private Show - Part 2

Flirt4Free 1 month ago

Jessica Host One Night Stand

Jessica Host One Night Stand

aShemaleTube 1 year ago

PHAT BOOTY Sissy Slut Rips Open Fishnet Tights, TWERKS, SPANKS, FUCKS Dildo, GAPES, and CUMS

PHAT BOOTY Sissy Slut Rips Open Fishnet Tights, TWERKS, SPANKS, FUCKS Dildo, GAPES, and CUMS

xHamster 2 years ago

Paulo & Jose & Sander Private Show

59% HD 2:00 / 10:44

Paulo & Jose & Sander Private Show

Flirt4Free 4 weeks ago

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

xHamster 2 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 4 months ago

Sandy Nell Private Show

67% HD 2:00 / 4:19

Sandy Nell Private Show

Flirt4Free 5 years ago

Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad

Massage session with the kinky TS babe turns into an amazing anal fuck for the lucky lad

Tranny.one 4 years ago

Worship Khloe: Submissive Helena Locke Devotes Herself to Mistress Kay

Worship Khloe: Submissive Helena Locke Devotes Herself to Mistress Kay

xHamster 1 month ago

Bad ladyboy punished for cheating

Bad ladyboy punished for cheating

VikiPorn 2 years 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 6 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 5 years ago

Jerking Off and Dirty Talk

HD 2:00 / 17:59

Jerking Off and Dirty Talk

Flirt4Free 8 years ago

Corrine Dittmann Private Show

51% 4K 2:00 / 17:14

Corrine Dittmann Private Show

Flirt4Free 10 months 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

FapHouse 5 months ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

xHamster 2 months ago

Femdom cropping pathetic sub

Femdom cropping pathetic sub

Some.Porn 7 months ago

Are You Ready to Please Your Mistress

Are You Ready to Please Your Mistress

xHamster 3 months ago

Shemale Punishes Her Puffy Nipples Until Lactation

Shemale Punishes Her Puffy Nipples Until Lactation

xHamster 8 months ago

Sophia Loreen Private Show

54% HD 2:00 / 37:35

Sophia Loreen Private Show

Flirt4Free 2 months ago

Hot Submissive Tgirl Slut Hired to Take Down Dictation Drink Piss Eat Ass Swallow Cum

Premium 50% 20:43

Hot Submissive Tgirl Slut Hired to Take Down Dictation Drink Piss Eat Ass Swallow Cum

xnxxGold 1 year ago

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

59% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

LoyalFans 8 months ago

Aleex & Paulo Private Show

52% HD 2:00 / 9:50

Aleex & Paulo Private Show

Flirt4Free 1 year ago

TRANSEROTICA Submissive Cassidy Quinn Endures Rough Torment

TRANSEROTICA Submissive Cassidy Quinn Endures Rough Torment

xHamster 3 years ago

A young 18-year-old student was fucked in the ass and filled with sperm with a smooth, beautiful narrow point!

A young 18-year-old student was fucked in the ass and filled with sperm with a smooth, beautiful narrow point!

xHamster 2 years ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 3 months ago

Leggy shemale domina punishes her bf's ass

Leggy shemale domina punishes her bf's ass

aShemaleTube 2 days ago

Punished sissy

72% HD 1:01 / 34:04

FapHouse 5 years ago

Sophia Loreen Private Show

60% HD 2:00 / 4:42

Sophia Loreen Private Show

Flirt4Free 1 month ago

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