Punishment Videos (35,217)

Mistress Kara Is a Hot Milf Librarian Who Will Punish Misbehavers

70% 0:11 / 37:31

Mistress Kara Is a Hot Milf Librarian Who Will Punish Misbehavers

Clips4sale 2 years ago

Rashel Mendoza Private Show

HD 2:00 / 16:57

Rashel Mendoza Private Show

Flirt4Free 1 year ago

Vintage Bad Girl and Christian XXX Fuck Bang

HD 0:39 / 27:55

Vintage Bad Girl and Christian XXX Fuck Bang

FapHouse 1 month ago

Bondage Sissy Bitch - 720HD

Bondage Sissy Bitch - 720HD

Clips4sale 3 years ago

A Futanari Miracle

A Futanari Miracle

Hentaied.Pro 3 years ago

How Santa Deep Throated and Anal Fucked Disobedient Teen Trans Slut Girl and Turned Her Into a Sissy Deer

HD 1:01 / 46:07

How Santa Deep Throated and Anal Fucked Disobedient Teen Trans Slut Girl and Turned Her Into a Sissy Deer

FapHouse 1 year ago

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Premium 56% HD 33:02

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

XNXXGold 2 years ago

Brunette Vinnie gets ass whip

65% HD 0:39 / 3:14

Brunette Vinnie gets ass whip

FapHouse 6 years ago

PISS JOCK: FtM Alpha Pees on You as Punishment for Spying - 1080p

PISS JOCK: FtM Alpha Pees on You as Punishment for Spying - 1080p

Clips4sale 2 years ago

(4K) Sissy Club Slut Part 1 of 2 : Mistress Stellina Trains Sissy for Deep Throating & Fat Cock Pegging (4K)

63% 4K 0:30 / 21:43

(4K) Sissy Club Slut Part 1 of 2 : Mistress Stellina Trains Sissy for Deep Throating & Fat Cock Pegging (4K)

Clips4sale 2 years ago

Shemale Sophia Ayalla Delicious Smother Fullweight - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - VERY SPECIAL PRICE: 34 MINUTES FOR US$ 15,99!

64% HD 0:30 / 33:53

Shemale Sophia Ayalla Delicious Smother Fullweight - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - VERY SPECIAL PRICE: 34 MINUTES FOR US$ 15,99!

Clips4sale 8 months ago

Piss as punishment

49% HD 0:13 / 4:18

Piss as punishment

Clips4sale 4 years ago

Kitty Kunt and her huge she cock

56% HD 0:39 / 23:01

Kitty Kunt and her huge she cock

FapHouse 4 years ago

Hot Sissygasm Cumpilation - 13 Cumshots in a Row!

Hot Sissygasm Cumpilation - 13 Cumshots in a Row!

Clips4sale 2 years ago

The Anal Whore of the Monastery

63% HD 0:39 / 31:44

The Anal Whore of the Monastery

FapHouse 5 months ago

Fat-co : Eating contest for your life, POV

Fat-co : Eating contest for your life, POV

LoyalFans 5 months ago

Wedgies Will Save You From Krampus!

4K 0:30 / 17:40

Wedgies Will Save You From Krampus!

Clips4sale 1 year ago

Hard Spanking For Naughty TV Jessica (MP4)

64% 0:12 / 9:26

Hard Spanking For Naughty TV Jessica (MP4)

Clips4sale 1 year ago

THE TRAINING: STRAP-ON, FINGERING & CHASTITY DENIAL

THE TRAINING: STRAP-ON, FINGERING & CHASTITY DENIAL

LoyalFans 1 month ago

You Want to Worship My Ass Big Time and then Smell My Armpits

HD 2:00 / 1:38:02

You Want to Worship My Ass Big Time and then Smell My Armpits

Flirt4Free 3 years ago

Fernanda Clar Private Show

Fernanda Clar Private Show

Flirt4Free 2 years ago

New Dildo 42cm X 10cm Extreme Dilation and Masochistic Slut Punishes Herself

New Dildo 42cm X 10cm Extreme Dilation and Masochistic Slut Punishes Herself

FapHouse 2 days ago

Melody Dubois Private Show

Melody Dubois Private Show

Flirt4Free 4 months ago

Dimitri Caruso Private Show

63% HD 2:00 / 16:56

Dimitri Caruso Private Show

Flirt4Free 3 years ago

Troy Colton Especial Private Fetish Show

HD 2:00 / 17:32

Troy Colton Especial Private Fetish Show

Flirt4Free 3 years ago

Lorens Tyler Private Show

60% HD 2:00 / 5:49

Lorens Tyler Private Show

Flirt4Free 2 years ago

The Po Opper Dom Daddy Show

57% 4K 2:00 / 15:13

The Po Opper Dom Daddy Show

Flirt4Free 1 year ago

Andres & Hercules & Lian Private Show

64% HD 2:00 / 5:16

Andres & Hercules & Lian Private Show

Flirt4Free 3 years ago

Do you dare to Dance?:dancer:Let me catch you with my Sexy MovesNaked and Horny(fire)(sarcasm)(c)

Do you dare to Dance?:dancer:Let me catch you with my Sexy MovesNaked and Horny(fire)(sarcasm)(c)

Flirt4Free 4 years ago

Busted!

FapHouse 11 months ago

Punishment in Perfection: The Dungeon's Discipline - Maitresse Julia

Punishment in Perfection: The Dungeon's Discipline - Maitresse Julia

Clips4sale 1 year ago

Big Cock stepMommy Turns You Sissy - hd mp4

41% HD 0:30 / 13:00

Big Cock stepMommy Turns You Sissy - hd mp4

Clips4sale 4 years ago

Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

73% 0:11 / 42:29

Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

C4S 3 years ago

Marianna,young gal in heels gets ass whip

Marianna,young gal in heels gets ass whip

FapHouse 6 years ago

Femdom Pool Party Fuck Fest - Mistress Kendra, Mistress Susi, Ts Slayer, pegging, orgy, ts girls wmv

58% HD 0:51 / 26:15

Femdom Pool Party Fuck Fest - Mistress Kendra, Mistress Susi, Ts Slayer, pegging, orgy, ts girls wmv

Clips4sale 3 years ago

Shemale Fetish Passion

HD 0:30 / 2:43:00

Shemale Fetish Passion

AEBN 11 years ago

Maximu Steel Private Show

Maximu Steel Private Show

Flirt4Free 3 weeks ago

hard crossdresser pegging. fuck anal with two dildo and fisting. big dildo sissy humiliation

HD 0:30 / 15:09

hard crossdresser pegging. fuck anal with two dildo and fisting. big dildo sissy humiliation

PornBox 3 years ago

MY RUBBERDOLL -Ch1: gagged, Slapped, whipped and punished -720p

4K 0:38 / 17:23

MY RUBBERDOLL -Ch1: gagged, Slapped, whipped and punished -720p

Clips4sale 1 year ago

Lazy House slave gets pegged hard for skipping chores

65% HD 0:39 / 19:10

Lazy House slave gets pegged hard for skipping chores

Clips4sale 2 years ago

All Girls Together Part 1 Lesbian Personal Services

All Girls Together Part 1 Lesbian Personal Services

Clips4sale 3 years ago

Melody Dubois Private Show

Melody Dubois Private Show

Flirt4Free 4 months ago

Brutus K Flexing Muscles on Cam

Brutus K Flexing Muscles on Cam

Flirt4Free 8 years ago

SHEMALE DOMINATION - 74 - ISABELLA FONTANELI & FABI - CLIP 1 OF 5 - MP4

SHEMALE DOMINATION - 74 - ISABELLA FONTANELI & FABI - CLIP 1 OF 5 - MP4

Clips4sale 1 year ago

Vintage Trans and Girl Blow Job and Anal Toy!

HD 1:01 / 32:19

Vintage Trans and Girl Blow Job and Anal Toy!

FapHouse 1 month ago

Melody Dubois Private Show

Melody Dubois Private Show

Flirt4Free 4 months ago

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

42% HD 1:01 / 25:09

Female Boss Makes Employee a Crossdresser, Stimulates His Dick with an Electric Vibrator, and Teases and Denies Him

FapHouse 1 year ago

Brayann & Bayron & Alejandro Private Show

Brayann & Bayron & Alejandro Private Show

Flirt4Free 2 years ago

Dimitri Caruso Private Show

Dimitri Caruso Private Show

Flirt4Free 4 years ago

My Man Alex Da Swinging Batista

HD 2:00 / 49:47

My Man Alex Da Swinging Batista

Flirt4Free 3 years ago

Loser slave loses bet against 7 Dommes and is gangbanged (1080 EN-sub)

44% HD 0:31 / 23:10

Loser slave loses bet against 7 Dommes and is gangbanged (1080 EN-sub)

Clips4sale 1 year ago

Futanari's Diary Pt.2. Stepson's Sph

57% HD 0:39 / 17:48

Futanari's Diary Pt.2. Stepson's Sph

FapHouse 3 months ago

Micky Mackenzie Private Show

66% HD 2:00 / 1:02:46

Micky Mackenzie Private Show

Flirt4Free 12 years ago

Mistress makes you her Sexless Sissy

Mistress makes you her Sexless Sissy

Clips4sale 11 months ago

Puppy in heat has to be locked away twice! Role Play by Tranny Dom! Sock Fetish Teasing! FULL CLIP

66% HD 0:30 / 16:50

Puppy in heat has to be locked away twice! Role Play by Tranny Dom! Sock Fetish Teasing! FULL CLIP

Clips4sale 1 year ago

Trans Femboy Slave Facesittig by BBW Mistress Sweaty Farts

Trans Femboy Slave Facesittig by BBW Mistress Sweaty Farts

Clips4sale 9 months ago

Licking My Feets

Licking My Feets

Flirt4Free 1 year ago

Thirsty Boy Gets Fed & Fucked!

Thirsty Boy Gets Fed & Fucked!

FapHouse 1 year ago

Alice Dildo Perfect Ass and Sticks out Long Tongue

HD 2:00 / 10:51

Alice Dildo Perfect Ass and Sticks out Long Tongue

Flirt4Free 4 years ago

Paul Walkers Private Show

Paul Walkers Private Show

Flirt4Free 2 months ago

THE CRUEL GIANT PUNISHING LITTLE JACK WITH FARTS - BY BRUNA SILVA - FULL VERSION IN FULL HD

62% HD 1:00 / 24:41

THE CRUEL GIANT PUNISHING LITTLE JACK WITH FARTS - BY BRUNA SILVA - FULL VERSION IN FULL HD

Clips4sale 3 years ago

Disciplining the Disobedient Sissy With Pegging - Mistress Julia

Disciplining the Disobedient Sissy With Pegging - Mistress Julia

Clips4sale 1 year ago

I’ve Been Fucking Your Gf , How Does My Cum Taste ?

57% HD 2:00 / 26:54

I’ve Been Fucking Your Gf , How Does My Cum Taste ?

Flirt4Free 3 years ago

Melody Dubois Private Show

63% HD 2:00 / 11:08

Melody Dubois Private Show

Flirt4Free 4 months ago

Angel Moran Private Show

Angel Moran Private Show

Flirt4Free 3 years ago

Archie Blossom Private Show

HD 2:00 / 22:44

Archie Blossom Private Show

Flirt4Free 6 months ago

Introducing Kinky TS Kitty Kat

46% 1:01 / 14:21

Introducing Kinky TS Kitty Kat

FapHouse 1 year ago

Jenny Skinny Private Show

65% HD 2:00 / 34:09

Jenny Skinny Private Show

Flirt4Free 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 2 weeks ago

Celeste Darell Private Show

HD 2:00 / 14:22

Celeste Darell Private Show

Flirt4Free 2 years ago

Snacktime! The Trans Giantess is hungry for ... you!

Premium HD 17:20

Snacktime! The Trans Giantess is hungry for ... you!

Sheer 1 month ago

Yasmin Cums to Collect!

53% 0:11 / 39:05

Yasmin Cums to Collect!

C4S 3 years ago

Alicia Akbar Private Show

Alicia Akbar Private Show

Flirt4Free 3 years ago

Maria Jade Fondled, Wedgied & Made To Orgasm (HD1080 WMV)

HD 0:11 / 13:17

Maria Jade Fondled, Wedgied & Made To Orgasm (HD1080 WMV)

Clips4sale 4 years ago

Dirty Talk in Spanish

Dirty Talk in Spanish

Flirt4Free 1 year ago

Archie Blossom Private Show

HD 2:00 / 10:00

Archie Blossom Private Show

Flirt4Free 7 months ago

Tranny slave girl in the pillory! Wax, ice and spanking until ecstasy!

66% HD 0:29 / 10:43

Tranny slave girl in the pillory! Wax, ice and spanking until ecstasy!

Clips4sale 1 year ago

Punishing The Sissy Maid

68% HD 0:28 / 29:34

Punishing The Sissy Maid

Clips4sale 2 years ago

Superman Confessing to Jimmy - Part 1

55% HD 2:00 / 16:37

Superman Confessing to Jimmy - Part 1

Flirt4Free 5 years ago

Violetta R Private Show

Violetta R Private Show

Flirt4Free 2 years ago

Ema Devine Private Show

66% 4K 2:00 / 5:07

Ema Devine Private Show

Flirt4Free 1 year ago

SHEMALE DOMINATION - 75 - YASMIN CASTRO & RICK BITCH - CLIP 3 OF 5 - WMV

SHEMALE DOMINATION - 75 - YASMIN CASTRO & RICK BITCH - CLIP 3 OF 5 - WMV

Clips4sale 1 year ago

My Punishment Turn Into Your Pleasure

65% 0:39 / 4:18

My Punishment Turn Into Your Pleasure

FapHouse 11 months ago

Susana & Britney Private Show

HD 2:00 / 17:27

Susana & Britney Private Show

Flirt4Free 2 years ago

Lena Pauline Private Show

Lena Pauline Private Show

Flirt4Free 3 years ago

Alice Woonder Private Show

HD 2:00 / 14:49

Alice Woonder Private Show

Flirt4Free 2 years ago

omocha Punished! Violet Wand and Strappado

omocha Punished! Violet Wand and Strappado

Clips4sale 9 months ago

Maid to Be Step-Daddy's Slut

56% HD 0:29 / 18:40

Maid to Be Step-Daddy's Slut

Clips4sale 3 years ago

Melody Dubois Private Show

Melody Dubois Private Show

Flirt4Free 4 months ago

you were meant to be a girl: loving feminization and pov bj - SD

you were meant to be a girl: loving feminization and pov bj - SD

Clips4sale 1 year ago

let s give your damn hole a good massage with my strap-on and my fingers, my trans slut!

63% 0:30 / 25:08

let s give your damn hole a good massage with my strap-on and my fingers, my trans slut!

PornBox 3 weeks ago

Melody Dubois Private Show

Melody Dubois Private Show

Flirt4Free 4 months ago

He Rides That Dildo Like a Good Boi

HD 2:00 / 15:57

He Rides That Dildo Like a Good Boi

Flirt4Free 2 years ago

My House Maid

Clips4sale 2 years ago

Ava Venom Bound and Ball Busted Ft Mistress Synthia Strong

Ava Venom Bound and Ball Busted Ft Mistress Synthia Strong

Clips4sale 1 year ago

Burlesque Bed of Nails pain and stocking striptease

Burlesque Bed of Nails pain and stocking striptease

Clips4sale 4 years ago

Melody Dubois Private Show

Melody Dubois Private Show

Flirt4Free 4 months ago

Porn Toy Venus TV

Porn Toy Venus TV

Clips4sale 2 years ago

720P Witch Turns You Into A Sissy Maid To Pay Off Your Debt

720P Witch Turns You Into A Sissy Maid To Pay Off Your Debt

Clips4sale 2 years ago

Cataleya Divine Private Show

Cataleya Divine Private Show

Flirt4Free 3 years ago

Wild Sabrina Private Show

Wild Sabrina Private Show

Flirt4Free 3 years ago

Irina Royce Private Show

Irina Royce Private Show

Flirt4Free 2 years ago

Witch Turns You Into A Sissy Maid To Pay Off Your Debt

Witch Turns You Into A Sissy Maid To Pay Off Your Debt

Clips4sale 2 years ago

Beatfuck The Pooch

60% HD 0:11 / 31:07

Beatfuck The Pooch

Clips4sale 2 years ago

Diabla Rivers Private Show

Diabla Rivers Private Show

Flirt4Free 2 years ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 5 years ago

meet my slave wmv

Premium 4K 34:30

meet my slave wmv

Clips4sale 1 year ago

Bullying her Sissy Balls Part 2: Humiliating Ball Weights

Premium HD 10:43

Bullying her Sissy Balls Part 2: Humiliating Ball Weights

Clips4sale 3 months ago

Cloe & Charlotte Private Show

Cloe & Charlotte Private Show

Flirt4Free 3 years ago

Angel Moran Private Show

Angel Moran Private Show

Flirt4Free 3 years ago

Etiquette school headmistress Inara Vesper trains and punishes naughty Gwendolyn

HD 0:10 / 22:13

Etiquette school headmistress Inara Vesper trains and punishes naughty Gwendolyn

LoyalFans 1 month ago

Goddess Sondra disciplines Barbie Satin

63% HD 0:10 / 8:20

Goddess Sondra disciplines Barbie Satin

LoyalFans 3 years ago

The BDSM Rebel TS Luzigain Is Punished and Fucked by Miss Nicanordic

65% HD 0:39 / 14:13

The BDSM Rebel TS Luzigain Is Punished and Fucked by Miss Nicanordic

FapHouse 2 years ago

Lilly Tino is a Sissy not Trans

Lilly Tino is a Sissy not Trans

Clips4sale 1 year ago

Alice Hottets Private Show

Alice Hottets Private Show

Flirt4Free 4 years ago

Introducing Kinky TS Kitty Kat

51% 0:39 / 14:21

Introducing Kinky TS Kitty Kat

FapHouse 1 year ago

Amber Burnt Private Show

HD 2:00 / 13:27

Amber Burnt Private Show

Flirt4Free 2 years ago

Caroline Bella Private Show

HD 2:00 / 14:58

Caroline Bella Private Show

Flirt4Free 3 years ago

Sandra Palmer Private Show

4K 2:00 / 24:59

Sandra Palmer Private Show

Flirt4Free 3 months ago

15 16 17 18 19

35,217 results found

Narrow your search

diaper punishment bbc punishment slave punishment spanking punishment anal punishment punishment gangbang punishment anal enema punishment self punishment asian punishment bdsm punishment teen punishment 18+ anal bbc punishment lesbian punishment hard punishment stepdaughter punishment femdom punishment pornstar punishment pussy punishment pegging punishment

Categories Pornstars

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.

© 2026 Pornmd.com. All rights reserved.