Punishment Videos (60,204)

Blonde White Femboy Milking Her Nipples and Slapping Them with Big Dildo

72% HD 0:39 / 11:02

Blonde White Femboy Milking Her Nipples and Slapping Them with Big Dildo

FapHouse 6 months ago

Futa Punishes Her Step-slut

59% 0:39 / 19:11

Futa Punishes Her Step-slut

FapHouse 7 months ago

Paulo & Jose & Sander Private Show

56% HD 2:00 / 15:24

Paulo & Jose & Sander Private Show

Flirt4Free 2 months ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

52% 1:01 / 21:31

Shemale Domination - 15 - Isa Laurens & Rick Bitch

FapHouse 7 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 6 months ago

Roommate Feminized and Fucked for Punishment

Roommate Feminized and Fucked for Punishment

XHamster 7 months ago

Lika Kai Party on Jul 16, 2026 - Part 2

55% 4K 2:00 / 15:57

Lika Kai Party on Jul 16, 2026 - Part 2

Flirt4Free 1 month ago

Black Tgirls: Mistress Venom's Amazing Cumshot

58% HD 0:39 / 18:23

Black Tgirls: Mistress Venom's Amazing Cumshot

FapHouse 6 months ago

Teaching My Trans Stepsister How To Fuck - TGIRLS HOUSE

Teaching My Trans Stepsister How To Fuck - TGIRLS HOUSE

XHamster 1 month ago

Leggy tranny domina punishing a dude to creampie

Leggy tranny domina punishing a dude to creampie

AShemaleTube 2 weeks ago

Shiri Allwood - Femboy Brat Jasper Gets Punished

Shiri Allwood - Femboy Brat Jasper Gets Punished

KeekAss 3 years ago

The Papi Chulo BBC Fisted Me Deep Until I Came

The Papi Chulo BBC Fisted Me Deep Until I Came

XHamster 5 months ago

Liz Rainbow Rough Fucking and Squirting by Crossdresser Perverted Freak

Liz Rainbow Rough Fucking and Squirting by Crossdresser Perverted Freak

XHamster 2 years ago

Jhordy & Maxx Private Show

54% HD 2:00 / 24:38

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

73% HD 1:01 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 3 years ago

Busty TS chick dominates a hogtied submissive masked man

Busty TS chick dominates a hogtied submissive masked man

Tranny.one 4 years ago

Lily Demure Deepthroats

Lily Demure Deepthroats

XHamster 6 months ago

Sophia Loreen Private Show

52% HD 2:00 / 18:41

Sophia Loreen Private Show

Flirt4Free 2 months ago

Dani Saenz Private Show

57% HD 2:00 / 33:18

Dani Saenz Private Show

Flirt4Free 4 years ago

Black Man With Huge Penis Punishes Internal Ejaculation

Black Man With Huge Penis Punishes Internal Ejaculation

ShemaleSex 3 weeks ago

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

Rough Punishment Pegging and Breeding for Panty Sniffing Step-bro

XHamster 4 months ago

Mike Swift & David Golden Private Show

65% HD 2:00 / 14:34

Mike Swift & David Golden Private Show

Flirt4Free 2 weeks ago

Lisan & Mine Private Show

66% 4K 2:00 / 23:47

Lisan & Mine Private Show

Camster 1 week ago

Sophie Fantasy Private Show

HD 2:00 / 22:02

Sophie Fantasy Private Show

Flirt4Free 1 month ago

Sophia Loreen Private Show

4K 2:00 / 11:45

Sophia Loreen Private Show

Camster 3 weeks ago

Four shemale punishers in black leather outfits manhandle a

Four shemale punishers in black leather outfits manhandle a

XHamster 2 years ago

Patric & Simon & Frederick Private Show

54% HD 2:00 / 11:22

Patric & Simon & Frederick Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

4K 2:00 / 10:50

Sophia Loreen Private Show

Camster 2 days ago

Sophia Loreen Party on Sep 7, 2026 - Part 3

Sophia Loreen Party on Sep 7, 2026 - Part 3

Flirt4Free 2 days ago

Sophia Loreen Party on Aug 22, 2026 - Part 3

64% 4K 2:00 / 1:33:22

Sophia Loreen Party on Aug 22, 2026 - Part 3

Flirt4Free 2 weeks ago

Femboy Viii punished

Femboy Viii punished

Transvids.tv 1 year ago

Sophia Loreen Private Show - Part 3

66% 4K 2:00 / 6:09

Sophia Loreen Private Show - Part 3

Flirt4Free 1 year ago

Wearing to cross dress

Wearing to cross dress

XHamster 1 year ago

Hot Early Footage of Pornstar Holly Parker

Hot Early Footage of Pornstar Holly Parker

XHamster 3 weeks ago

Why I Should Be Punished

Why I Should Be Punished

XHamster 1 week ago

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

Trans Girl Worships His Trans Cock Before He Wrecks Her Ass

XHamster 10 months ago

sissy college girls get back at their mean coach

69% HD 1:01 / 38:51

sissy college girls get back at their mean coach

FapHouse 4 years ago

Corrine Dittmann Private Show

54% 4K 2:00 / 17:14

Corrine Dittmann Private Show

Flirt4Free 1 year ago

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

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

ShemaleSex 1 month ago

Leather outfit ts domina punishes her slave s ass and m

Leather outfit ts domina punishes her slave s ass and m

FetishShrine 2 months ago

Lika Kai Private Show

4K 2:00 / 27:22

Lika Kai Private Show

Flirt4Free 1 week ago

Mistress Trap Punishment

Mistress Trap Punishment

AShemaleTube 1 year ago

Crossdressed twink fucked bareback by straight curious Arab

Crossdressed twink fucked bareback by straight curious Arab

Tranny.one 3 years ago

CBT Genital Rubber Band Torture and Ruined Orgasm of Trans Slut

CBT Genital Rubber Band Torture and Ruined Orgasm of Trans Slut

XHamster 2 years ago

Sophia Loreen Party on Aug 21, 2026 - Part 6

61% 4K 2:00 / 54:49

Sophia Loreen Party on Aug 21, 2026 - Part 6

Camster 2 weeks ago

”Assfucking Punishment for Submissive Sluts on the Upper Floor”

”Assfucking Punishment for Submissive Sluts on the Upper Floor”

TransHero 9 months ago

Oliver Whitee Party on Aug 28, 2026 - Part 4

HD 2:00 / 2:17:20

Oliver Whitee Party on Aug 28, 2026 - Part 4

Flirt4Free 1 week ago

Slave rental

XHamster 1 year ago

Sophia Loreen Party on Aug 21, 2026 - Part 6

4K 2:00 / 54:49

Sophia Loreen Party on Aug 21, 2026 - Part 6

Flirt4Free 2 weeks ago

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Tranny.one 4 years ago

Sophia Loreen Party on Jul 17, 2026 - Part 4

HD 2:00 / 1:01:12

Sophia Loreen Party on Jul 17, 2026 - Part 4

Flirt4Free 1 month ago

Viky & Master Private Show

66% HD 2:00 / 10:29

Viky & Master Private Show

Camster 9 months ago

Michael Hawtin Private Show

57% HD 2:00 / 16:48

Michael Hawtin Private Show

Flirt4Free 1 year ago

Archie Blossom Private Show

60% HD 2:00 / 8:15

Archie Blossom Private Show

Flirt4Free 6 months ago

Sissy Slut Ball Busting Jessica Bloom Has Two Plapping Orgsams Back to Back And Eats Her Own Cum!

Sissy Slut Ball Busting Jessica Bloom Has Two Plapping Orgsams Back to Back And Eats Her Own Cum!

XHamster 1 week ago

Punished In Place 2: featuring Livi Doll

Premium HD 27:39

Punished In Place 2: featuring Livi Doll

XVideosRed 2 years ago

Sophia Loreen Party on Sep 4, 2026 - Part 2

4K 2:00 / 54:21

Sophia Loreen Party on Sep 4, 2026 - Part 2

Camster 4 days ago

Lily Demure Deepthroats

Lily Demure Deepthroats

XHamster 7 months ago

3some with Two Shemale Tops

3some with Two Shemale Tops

Pervclips 6 days ago

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Tranny.one 4 years ago

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

55% HD 0:39 / 39:21

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

FapHouse 5 months ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Camster 2 months ago

Jose & Richard Private Show

Jose & Richard Private Show

Flirt4Free 4 months ago

Spanked while chained up in the Mrs Playroom

Spanked while chained up in the Mrs Playroom

Tranny.one 4 years ago

Getting Punished for Braking in the Apartments

54% 1:01 / 32:23

Getting Punished for Braking in the Apartments

FapHouse 5 months ago

Hot White Dress

Hot White Dress

Flirt4Free 5 months ago

Cute Trans Elastic Mommy Tit Slap and Lactating after Pumping her Tits with Vacuum Milking Machine

Cute Trans Elastic Mommy Tit Slap and Lactating after Pumping her Tits with Vacuum Milking Machine

XHamster 3 weeks ago

Jacob Malik Private Show

HD 2:00 / 15:57

Jacob Malik Private Show

Flirt4Free 1 year ago

3some with Two Shemale Tops

3some with Two Shemale Tops

Katestube 1 week ago

Piss Pump With Enema Option

Piss Pump With Enema Option

XHamster 3 years ago

Sophia Loreen Private Show

66% HD 2:00 / 4:58

Sophia Loreen Private Show

Flirt4Free 3 months ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

XHamster 9 months ago

Troy Khalil Private Show

HD 2:00 / 13:47

Troy Khalil Private Show

Flirt4Free 2 years ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

XHamster 4 months ago

Robber gets punished with some hardcore anal pounding by the horny TS chick

Robber gets punished with some hardcore anal pounding by the horny TS chick

Tranny.one 4 years ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

67% HD 0:30 / 58:54

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)

Clips4sale 2 years ago

Master & Christian Mckenzie & Christian Rey Private Show

54% HD 2:00 / 13:53

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Dudes caught transexual and punished him orally and anally

Dudes caught transexual and punished him orally and anally

Tranny.one 9 years ago

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

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

Clips4sale 3 years ago

Julia ebony sex doll slave blonde bobcut

Julia ebony sex doll slave blonde bobcut

XHamster 6 days ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Colombian Boys Private Show

48% HD 2:00 / 7:59

Colombian Boys Private Show

Flirt4Free 2 years 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

Tranny.one 4 years ago

Sophia Loreen Private Show

67% HD 2:00 / 7:25

Sophia Loreen Private Show

Camster 1 month ago

Sensually Milking & Edging Trans Cock

63% HD 0:10 / 14:44

Sensually Milking & Edging Trans Cock

LoyalFans 2 years ago

Busty Shemale Punishes Dude in Black Mask

Busty Shemale Punishes Dude in Black Mask

BeMyHole 1 year ago

Skinny ts punished by BBC

Skinny ts punished by BBC

KeekAss 3 months ago

Sophia Loreen Party on Jul 29, 2026 - Part 3

55% 4K 2:00 / 1:17:55

Sophia Loreen Party on Jul 29, 2026 - Part 3

Camster 1 month ago

Lovely trans babe in the black dress humiliates and fucks the nasty subservient lad

Lovely trans babe in the black dress humiliates and fucks the nasty subservient lad

Tranny.one 4 years ago

Whiping It out Through My Nerdy Shirt

Whiping It out Through My Nerdy Shirt

Flirt4Free 2 years ago

Unbelievable double dildo punishment Fuck

Unbelievable double dildo punishment Fuck

AShemaleTube 2 weeks 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

German TS Surprised by a Creep - as a Punishment, He Is Being Fucked Hard and Pissed on

57% 1:01 / 17:41

German TS Surprised by a Creep - as a Punishment, He Is Being Fucked Hard and Pissed on

FapHouse 3 years ago

Sensually Milking & Edging Trans Cock

74% 0:25 / 14:43

Sensually Milking & Edging Trans Cock

Clips4sale 2 years ago

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

XHamster 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

Mistress Flo Fists the Ass of Two Mature Transvestites

Mistress Flo Fists the Ass of Two Mature Transvestites

XHamster 9 months ago

Frederick & Aleex & Daaniel Private Show

58% HD 2:00 / 4:03

Frederick & Aleex & Daaniel Private Show

Flirt4Free 11 months ago

Double domination - TS creampie

58% 1:01 / 22:11

Double domination - TS creampie

FapHouse 5 years ago

Aspen Brooks Fucks New Comer Jessie Prather Into Domestic Bliss

Aspen Brooks Fucks New Comer Jessie Prather Into Domestic Bliss

XHamster 3 months ago

Bhabhi Punished her Shemale Cock

Bhabhi Punished her Shemale Cock

XHamster 4 weeks ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Hot Ebony Baddie TS 5F61 Gets Punished & Loves It

Hot Ebony Baddie TS 5F61 Gets Punished & Loves It

Eporner 8 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

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

”Babe deep throat sucks in public”

”Babe deep throat sucks in public”

TransHero 8 months ago

Anabel Fiofilova Private Show

Anabel Fiofilova Private Show

Camster 3 weeks ago

Pledge and get spot for my group show..start now!!

60% HD 2:00 / 19:52

Pledge and get spot for my group show..start now!!

Flirt4Free 7 years ago

Shemale Punishes Her Puffy Nipples Until Lactation

65% HD 1:01 / 5:40

Shemale Punishes Her Puffy Nipples Until Lactation

FapHouse 1 year ago

Sophia Loreen Party on Sep 8, 2026 - Part 4

4K 2:00 / 49:05

Sophia Loreen Party on Sep 8, 2026 - Part 4

Camster 1 day ago

Trans All Girl Dominance. Restrain Bondage, Electro Ass Fucking and Deep-Throat Jobs.

Trans All Girl Dominance. Restrain Bondage, Electro Ass Fucking and Deep-Throat Jobs.

TrannyGem 7 years ago

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

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

XHamster 7 months ago

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Innocent intern guy gets his ass banged by the nasty shemale boss in the office

Tranny.one 4 years ago

Gia Darling and Her Scrub Brush

Gia Darling and Her Scrub Brush

XHamster 1 year ago

Kendall Cent - Penalizes Corbin Dallas

Kendall Cent - Penalizes Corbin Dallas

TrannyGem 6 years ago

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

Punished Slaves BDSM Bondage Gay Amador Big Dick 2

XHamster 6 months ago

Step Mom Punishment Her Son With Bondage Sex - Uncensored Hentai

Step Mom Punishment Her Son With Bondage Sex - Uncensored Hentai

HentaiGem 3 years ago

Shemale Ananda India Face Fuck - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 34 MINUTES FOR US$ 15,99!

66% HD 0:30 / 33:49

Shemale Ananda India Face Fuck - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 34 MINUTES FOR US$ 15,99!

Clips4sale 10 months ago

School teenie Practices Painfull Sensation

School teenie Practices Painfull Sensation

GayDudesFucking 1 year ago

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