Punish Videos (38,585)

Julia Gives a Schooling - TGirlJapanHardcore

Julia Gives a Schooling - TGirlJapanHardcore

AbTranny 6 years ago

Courageous TS Natalie Mars bends down and lets the giant rubber cock destroy her asshole

Courageous TS Natalie Mars bends down and lets the giant rubber cock destroy her asshole

Fapnado 2 years ago

Fuck the Slut

HD 2:00 / 48:30

Flirt4Free 1 year ago

Master & Christian Mckenzie & Christian Rey Private Show

66% HD 2:00 / 7:39

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Oct 23, 2025 - Part 2

65% 4K 2:00 / 23:12

Sophia Loreen Party on Oct 23, 2025 - Part 2

Flirt4Free 2 months ago

Hercules & Lance & Lian Miller Private Show

41% HD 2:00 / 5:02

Hercules & Lance & Lian Miller Private Show

Flirt4Free 3 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 4 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

”Deep Feet Punishment: Mouth Screwed”

”Deep Feet Punishment: Mouth Screwed”

TransHero 3 weeks ago

Submissive Gets Owned By Four Dommes by TSDomme.com

Submissive Gets Owned By Four Dommes by TSDomme.com

xHamster 1 year ago

Master & Ithan & Aleex Private Show

57% HD 2:00 / 31:36

Master & Ithan & Aleex Private Show

Flirt4Free 5 months ago

The Sissy Toy of the Goddess

64% HD 1:01 / 14:37

The Sissy Toy of the Goddess

FapHouse 1 year ago

Dominatrix caning useless slave

Dominatrix caning useless slave

Tranny.one 4 years ago

Full-naked Femboy Shows Her Tits And Faps Shaft

Full-naked Femboy Shows Her Tits And Faps Shaft

Rock.PORN 1 year ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 4 days ago

Dani Saenz Private Show

HD 2:00 / 15:42

Dani Saenz Private Show

Flirt4Free 4 years ago

My Nipples So Hard^^

My Nipples So Hard^^

Flirt4Free 8 months ago

Leather mistress punishes sub with gayblowjob

Leather mistress punishes sub with gayblowjob

SexTubeSpot 4 years ago

AS TRANS ME LEVARAM PRA HIDRO E PRO CLOSET PRA COMER MEU CU

Premium HD 6:27

AS TRANS ME LEVARAM PRA HIDRO E PRO CLOSET PRA COMER MEU CU

XVideosRed 3 years ago

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

59% HD 1:01 / 29:35

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

FapHouse 3 years ago

frenchbaguettes-yaya-the-punisher

frenchbaguettes-yaya-the-punisher

KeekAss 2 years ago

full mouth gag device bondage submissive tgirl shock collar pain slut training

63% HD 0:29 / 13:38

full mouth gag device bondage submissive tgirl shock collar pain slut training

PornBox 1 year ago

Lovely lad fulfills the TS babe's feet fetish before sucking and riding her thick cock

Lovely lad fulfills the TS babe's feet fetish before sucking and riding her thick cock

Tranny.one 4 years ago

”Transgender in chastity punished & anal fucked”

”Transgender in chastity punished & anal fucked”

ThePornstar 1 year ago

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

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

PornBox 2 years ago

PUNISHMENT

aShemaleTube 2 months ago

Curvy inked tranny punishes her best friend

Curvy inked tranny punishes her best friend

Eporner 3 years ago

Blazing Hot Domination by The Fire FULL video from

Blazing Hot Domination by The Fire FULL video from

xHamster 1 year ago

Wearing to cross dress

Wearing to cross dress

xHamster 1 year ago

Rika Fox gets punished #8 full 23 min vid out now! Subscribe and enjoy 😉

Rika Fox gets punished #8 full 23 min vid out now! Subscribe and enjoy 😉

aShemaleTube 6 months ago

A Disgrace to Our Town Part 1

A Disgrace to Our Town Part 1

xHamster 9 months ago

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass

Releasing Enemas and Pissing Her Mouth before Pegging Her Ass

xHamster 1 month ago

”Amazing teen Vienna Rose banged by her professor's big cock”

”Amazing teen Vienna Rose banged by her professor's big cock”

ThePornstar 7 months ago

TS Mistress Alexa Dominates Muscular

TS Mistress Alexa Dominates Muscular

TrannyGem 2 weeks ago

”Satisfying Kasey Kei submits to King Noire for rough assfucking punishment”

”Satisfying Kasey Kei submits to King Noire for rough assfucking punishment”

Zatube 1 month 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

HOT Rika Fox getting Punished by The BBC PUNISHER

HOT Rika Fox getting Punished by The BBC PUNISHER

aShemaleTube 3 weeks ago

Alice Kizar Private Show

Alice Kizar Private Show

Flirt4Free 3 days ago

Mistress punishes mask boy

Mistress punishes mask boy

FapCat 1 month ago

Cuckold Therapy - Sarina Havok, Robin Coffins and Cherry Mavrik

Premium HD 21:05

Cuckold Therapy - Sarina Havok, Robin Coffins and Cherry Mavrik

XVideosRed 3 years ago

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

HD 0:39 / 19:41

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

FapHouse 1 month ago

Messy Sissy Cream Enema & Banana Strapon Ride

67% HD 1:01 / 26:42

Messy Sissy Cream Enema & Banana Strapon Ride

FapHouse 4 months ago

Lucky man gets gangbanged by the gorgeous TS chicks

Lucky man gets gangbanged by the gorgeous TS chicks

Tranny.one 4 years ago

TS teacher anal punishes Matthew in a study hall

TS teacher anal punishes Matthew in a study hall

aShemaleTube 3 months ago

Desire Sweet Private Show

HD 2:00 / 32:10

Desire Sweet Private Show

Flirt4Free 1 week ago

Hung ebony shemale S.S punishes a guyu with her big cock

Hung ebony shemale S.S punishes a guyu with her big cock

aShemaleTube 5 months ago

Dom Fucks and Spank Delia Delions

57% HD 0:39 / 33:03

Dom Fucks and Spank Delia Delions

FapHouse 2 years 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.

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 1 month ago

Lucas Miiller Private Show

HD 2:00 / 26:15

Lucas Miiller Private Show

Flirt4Free 1 week ago

TS Nicole Montero fucking the TS Pornstar Laisa Lins after the wel deserved Punishment, and cums over her

TS Nicole Montero fucking the TS Pornstar Laisa Lins after the wel deserved Punishment, and cums over her

XVideosRed 5 years ago

”Francesca Le eats her maid out”

”Francesca Le eats her maid out”

ThePornstar 1 year ago

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

49% HD 0:39 / 29:35

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

FapHouse 3 years ago

Punish Me Shrine God, if I Am Too Provocative

Punish Me Shrine God, if I Am Too Provocative

xHamster 2 weeks ago

I Love This Hot Time

HD 2:00 / 16:10

I Love This Hot Time

Flirt4Free 3 years 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 3 weeks ago

Sissy tgirl rough anal

Sissy tgirl rough anal

Fetishpapa 8 years ago

”Used Hoe Holes part II”

”Used Hoe Holes part II”

TransHero 1 week ago

Shocking Confession to the Wedding Priest!

69% HD 0:39 / 9:27

Shocking Confession to the Wedding Priest!

FapHouse 1 year ago

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

64% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman | MahoganyQen

LoyalFans 2 months ago

Katy Ling Private Show

Katy Ling Private Show

Flirt4Free 1 week ago

Bondage hentai shemale with three cocks gets punishment

Bondage hentai shemale with three cocks gets punishment

SleazyNEasy 12 years ago

”Mansion maid teaches Eiji BDSM”

”Mansion maid teaches Eiji BDSM”

TransHero 3 weeks ago

Freya Bliss Private Show

Freya Bliss Private Show

Flirt4Free 4 days ago

Trans Gal Worships His Trans Wang Before This chab Wrecks Her Ass

Trans Gal Worships His Trans Wang Before This chab Wrecks Her Ass

Dafreeporn 4 weeks ago

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

Spandex Sissy Punished by V-Card Fuckmachine Smacking Dickblowing Pegging by Domina Mercer

TrannyGem 4 years ago

squirt - Part 2

57% 4K 2:00 / 9:52

squirt - Part 2

Flirt4Free 7 months ago

”Dominant latex Trans Aspen Brooks ass pumping pounds Draven Navarro hard”

”Dominant latex Trans Aspen Brooks ass pumping pounds Draven Navarro hard”

Zatube 3 weeks ago

Bound up femboy required to cum! Post Climax Punishment

Bound up femboy required to cum! Post Climax Punishment

ShemaleSin 8 months ago

Naughty boy gets punished by the sexy tranny queen in hardcore TS fuck

Naughty boy gets punished by the sexy tranny queen in hardcore TS fuck

Tranny.one 3 years ago

Visceratio Gets Her Ass Punished

Visceratio Gets Her Ass Punished

AbTranny 8 years ago

Double Dommed in the Dungeon, a Trans Femdom BDSM Threesome

65% HD 0:10 / 27:36

Double Dommed in the Dungeon, a Trans Femdom BDSM Threesome

LoyalFans 7 months ago

”River Enza punishes big transgender butthole with dildo”

”River Enza punishes big transgender butthole with dildo”

HQBang 10 months ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

xHamster 1 month ago

Viky & Master Private Show

67% HD 2:00 / 10:29

Viky & Master Private Show

Flirt4Free 1 month ago

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

63% HD 0:39 / 14:56

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

FapHouse 2 months ago

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

54% 1:01 / 24:48

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

FapHouse 1 month ago

Lily Demure Deepthroats

69% HD 1:01 / 30:01

Lily Demure Deepthroats

FapHouse 1 year ago

Trans Angels - Chanel Santini Has to Punish Her Employees When They Get Caught Masturbating on the Clock!

Trans Angels - Chanel Santini Has to Punish Her Employees When They Get Caught Masturbating on the Clock!

xHamster 2 years ago

Going Knuckle Deep torture

Going Knuckle Deep torture

TrannyGem 5 years ago

Pervert pigs 2

52% HD 0:39 / 11:02

FapHouse 3 years ago

AS TRANS PIROCUDAS ME FIZERAM DE ESCRAVA NA COZINHA E COMERAM MEU CU

AS TRANS PIROCUDAS ME FIZERAM DE ESCRAVA NA COZINHA E COMERAM MEU CU

XVideosRed 3 years 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

Tranny nun punishing anal male prisoner

Tranny nun punishing anal male prisoner

aShemaleTube 6 years ago

Cross-training Cock

Cross-training Cock

Some.Porn 1 year ago

Sophia Loreen Private Show

52% 4K 2:00 / 5:19

Sophia Loreen Private Show

Flirt4Free 4 months 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

The League of Extraordinary Transsexuals: The Final Punishment

The League of Extraordinary Transsexuals: The Final Punishment

AbTranny 9 years ago

Ts bondage Punish my 19 year-old donk and mouth

Ts bondage Punish my 19 year-old donk and mouth

Eporner 1 year ago

”T-girl in chastity punished & anal fucked”

”T-girl in chastity punished & anal fucked”

LesbianBliss 2 weeks ago

”Cougar TS mother in law punishing lazy teeanger”

”Cougar TS mother in law punishing lazy teeanger”

4Wank 1 year ago

Got caught peeping upon Trans Roommate jerking-off punished including girlcock

Got caught peeping upon Trans Roommate jerking-off punished including girlcock

KAMS 10 months ago

Owen & Ronaldo & Patric Private Show

48% HD 2:00 / 14:02

Owen & Ronaldo & Patric Private Show

Flirt4Free 2 years 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

Feelipe & Adara Private Show

64% HD 2:00 / 4:26

Feelipe & Adara Private Show

Flirt4Free 6 months ago

Slut throatfucked in front of audience till cum in mouth

Slut throatfucked in front of audience till cum in mouth

Some.Porn 1 year ago

Watch torment of a Asian shemale

Watch torment of a Asian shemale

xHamster 1 year ago

”Bondage teen punished hard with ropes & prick”

”Bondage teen punished hard with ropes & prick”

TransHero 3 weeks 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 7 months ago

Babysit On My Chest

Babysit On My Chest

Some.Porn 4 months ago

Elix & Elias & Paulo Private Show

44% HD 2:00 / 5:24

Elix & Elias & Paulo Private Show

Flirt4Free 5 months ago

Three brunette and one blonde tranny punisher fuck a stud in bondage

Three brunette and one blonde tranny punisher fuck a stud in bondage

aShemaleTube 1 year ago

Trans Angel Worships His Trans Weenie Previous to This guy Wrecks Her Booty

Trans Angel Worships His Trans Weenie Previous to This guy Wrecks Her Booty

ShemaleSin 3 weeks ago

asian trans beauty billie beaumont punishes petite trans cutie in nurse outfit

HD 0:30 / 15:21

asian trans beauty billie beaumont punishes petite trans cutie in nurse outfit

PornBox 2 months ago

Spit-roasted And Treated Like A Plaything

Spit-roasted And Treated Like A Plaything

Tranny.one 4 years ago

A slim girl getting punished by her old master in a dungeon

A slim girl getting punished by her old master in a dungeon

xHamster 1 year ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 4 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

Independent Training No72 Punishment Training Chair Part 2

Independent Training No72 Punishment Training Chair Part 2

xHamster 5 days ago

Master & Ithan Private Show

41% HD 2:00 / 12:09

Master & Ithan Private Show

Flirt4Free 6 months ago

Jhordy & Maxx Private Show

44% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 4 months ago

Feelipe & Adara Private Show

54% HD 2:00 / 8:50

Feelipe & Adara Private Show

Flirt4Free 3 months ago

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

xHamster 2 months ago

Mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min

Mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min

AbTranny 3 years ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 6 years ago

Instructions from the trainer No 11 Daily exposure walks

Instructions from the trainer No 11 Daily exposure walks

xHamster 1 month ago

Mistress Kora Bell Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance

Mistress Kora Bell Punishes Trans Toy: Creampie Clean-up & Foot Worship After Defiance

xHamster 2 months ago

Petite TS Avery Angel loves BBC! Avery gets punished she's so hot!

Petite TS Avery Angel loves BBC! Avery gets punished she's so hot!

aShemaleTube 1 week ago

Busty Shemale Punishes Dude in Black Mask

Busty Shemale Punishes Dude in Black Mask

BeMyHole 1 year ago

Jessica Host One Night Stand

68% HD 1:01 / 35:34

Jessica Host One Night Stand

FapHouse 6 months ago

1 2 3 4 5

38,585 results found

Narrow your search

punish mom mom punish anal punish punish anal teen punish 18+ stepdad punish punish teen 18+ punish teens 18+ lesbian punish teacher punish stepmom punish school punish punish stepmom punish orgasm punish wife milf punish gia dimarco punish tori black punish trina michaels punish kelly divine punish

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.