Punishment Videos (40,584)

Maria Saint Private Show

Maria Saint Private Show

Flirt4Free 6 months ago

Horny Sissy Old Foreign with My Pinoy Master Trans

Horny Sissy Old Foreign with My Pinoy Master Trans

xHamster 11 months ago

Danna Nichols Private Show

Danna Nichols Private Show

Flirt4Free 2 years ago

Nadia Honey Private Show

HD 2:00 / 16:56

Nadia Honey Private Show

Flirt4Free 2 years ago

While my best friend is at work, this is the first time I've ever been to work Clip 2

While my best friend is at work, this is the first time I've ever been to work Clip 2

xHamster 2 months ago

I Fucked Your Husband Again

HD 2:00 / 38:51

I Fucked Your Husband Again

Flirt4Free 5 years ago

Big Girl Dick TS Chanel Jordan, fucks Pretty Trans girl, Gray Perrier in doggy with red lingerie Clip 2

Big Girl Dick TS Chanel Jordan, fucks Pretty Trans girl, Gray Perrier in doggy with red lingerie Clip 2

xHamster 4 months ago

Alexxa Ivanova Private Show

HD 2:00 / 11:06

Alexxa Ivanova Private Show

Flirt4Free 2 years ago

Brutus K Private Show

HD 2:00 / 14:26

Brutus K Private Show

Flirt4Free 4 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 2 years ago

Micky Mackenzie Private Show

56% HD 2:00 / 5:38

Micky Mackenzie Private Show

Flirt4Free 11 years ago

TS Dominant-Bitch in Latex Bangs Guy (Natalie Mars)

TS Dominant-Bitch in Latex Bangs Guy (Natalie Mars)

ShemaleSin 2 years ago

Jineteando de frente sobre el potro

Jineteando de frente sobre el potro

Tranny.one 4 years ago

Elvis Rey & Andres & Aron Private Show

HD 2:00 / 26:40

Elvis Rey & Andres & Aron Private Show

Flirt4Free 2 years ago

Sebastian Herrera Private Show

Sebastian Herrera Private Show

Flirt4Free 1 year ago

Maria Saint Private Show

Maria Saint Private Show

Flirt4Free 6 months ago

Margaux Fox Private Show

Margaux Fox Private Show

Flirt4Free 4 years ago

hot jerk off and pec play

HD 2:00 / 24:58

hot jerk off and pec play

Flirt4Free 14 years ago

Sissy gets cone punishment

Sissy gets cone punishment

Pornzona 3 weeks ago

Freak of Nature 13 Older Endless Soundy Cuntrubbing

Freak of Nature 13 Older Endless Soundy Cuntrubbing

SortPorn 5 years ago

Luccas & Jhordy Private Show

63% HD 2:00 / 7:43

Luccas & Jhordy Private Show

Flirt4Free 8 months ago

Brunette tranny punishers take a stud prisoner and fuck him

Brunette tranny punishers take a stud prisoner and fuck him

VipTube 1 year ago

Piss Punishment for Tiny Pest

Piss Punishment for Tiny Pest

Clips4sale 3 years ago

Avid Edging Punishment - Restrained On the Impalement Chair Estim Electro Shlong Stimultion and Anal sex tool Prostate Milking Precum Trickling Jizz flow Ruined

Avid Edging Punishment - Restrained On the Impalement Chair Estim Electro Shlong Stimultion and Anal sex tool Prostate Milking Precum Trickling Jizz flow Ruined

ShemaleSin 4 weeks ago

See the best ride and the best ass cheekcs bouncing!!

See the best ride and the best ass cheekcs bouncing!!

Flirt4Free 3 years ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 6 months ago

Max Russel Private Show

Max Russel Private Show

Flirt4Free 2 years ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 4 years ago

Sophia Loreen Party on Oct 16, 2024 - Part 3

HD 2:00 / 18:33

Sophia Loreen Party on Oct 16, 2024 - Part 3

Flirt4Free 1 year ago

Outdoor Fisting Gangbang - Past the Elbow Featuring Jasmine_dlight, Hairy Kink Mоther & Roxxie Sweetheart

HD 0:39 / 10:47

Outdoor Fisting Gangbang - Past the Elbow Featuring Jasmine_dlight, Hairy Kink Mоther & Roxxie Sweetheart

FapHouse 3 months ago

Crossdresser Punishment

Crossdresser Punishment

AbGay 1 year ago

”Seductive Tranny Chelsea Marie teases until Pierce Paris fucks her hard”

”Seductive Tranny Chelsea Marie teases until Pierce Paris fucks her hard”

LesbianBliss 3 weeks ago

Nelly Gale Private Show

66% 4K 2:00 / 7:58

Nelly Gale Private Show

Flirt4Free 5 months ago

Lyndon F Private Show

63% HD 2:00 / 9:30

Lyndon F Private Show

Flirt4Free 1 month ago

A shy teen girl gets a hard spanking from her master with a long whip

A shy teen girl gets a hard spanking from her master with a long whip

xHamster 1 year ago

Fucking Machine

67% HD 0:11 / 14:09

Fucking Machine

Clips4sale 3 years ago

Flame and Control

Flame and Control

LoyalFans 4 months ago

Desi horny Sissy Anal and big cock cum shot

Desi horny Sissy Anal and big cock cum shot

xHamster 1 year ago

Alice Kizar Private Show

4K 2:00 / 21:04

Alice Kizar Private Show

Flirt4Free 1 month ago

pegging him with my two side strapon

pegging him with my two side strapon

AnalVids 1 year ago

Dominating Kyla Keys Spanking and Bondage Rough Fuck

HD 0:10 / 16:10

Dominating Kyla Keys Spanking and Bondage Rough Fuck

LoyalFans 2 years ago

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

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

ThePornstar 10 months ago

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

65% 4K 0:30 / 58:54

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

Clips4sale 1 year ago

Alessia Viilla & Charlie Lenox Private Show

Alessia Viilla & Charlie Lenox Private Show

Flirt4Free 9 months ago

”POV - Lilu Moon bribes you & gets punished by dick”

”POV - Lilu Moon bribes you & gets punished by dick”

TransHero 3 months ago

TS Paradise gets stretched her asshole by Jayden Marcos

TS Paradise gets stretched her asshole by Jayden Marcos

Fapnado 3 years ago

Femboy Samus Wedgie and Anal Stretching Punishment with Huge Dildo

Femboy Samus Wedgie and Anal Stretching Punishment with Huge Dildo

xHamster 2 months ago

The Almost all nice-looking Trans Boobs in the World Pinched and Lactating

The Almost all nice-looking Trans Boobs in the World Pinched and Lactating

PornFreeNow 4 months ago

Trans Ass POV

Premium HD 7:00

AEBN 2 years ago

spanking crossdresser

spanking crossdresser

BDSMX 1 year ago

bbw farting on trans girl slave cock

HD 0:30 / 12:44

bbw farting on trans girl slave cock

PornBox 1 year ago

Gangbanged TS punished with cum in own mouth

Gangbanged TS punished with cum in own mouth

AbTranny 6 years ago

The Sissification of Brenda 5 Part Collection Written by Sissy Brenda Narrated by Shayla Aspasia

Premium HD 3:14:26

The Sissification of Brenda 5 Part Collection Written by Sissy Brenda Narrated by Shayla Aspasia

Clips4sale 1 year ago

Goddess Sondra disciplines Barbie Satin

Goddess Sondra disciplines Barbie Satin

LoyalFans 3 years ago

”Big dick shemales turn their yoga class into an ass fucking 3some”

”Big dick shemales turn their yoga class into an ass fucking 3some”

ThePornstar 3 months ago

Roxanne Roulette Spank Ass Long Masturbate Anal Play

HD 2:00 / 47:43

Roxanne Roulette Spank Ass Long Masturbate Anal Play

Flirt4Free 9 years ago

Denali Danger gets Punished clips #3

Denali Danger gets Punished clips #3

aShemaleTube 1 year ago

Sophia Loreen Private Show

HD 2:00 / 20:49

Sophia Loreen Private Show

Flirt4Free 3 weeks ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Lover of Satisfaction

Lover of Satisfaction

Flirt4Free 2 years ago

Shemale wearing a BDSM mask and Asuka Cosplay Stretches her Nipples and Punishes her Breasts with a Vacuum Machine until they Lactate

Premium HD 15:59

Shemale wearing a BDSM mask and Asuka Cosplay Stretches her Nipples and Punishes her Breasts with a Vacuum Machine until they Lactate

XVideosRed 3 months ago

Incontinent Diaper Dominatrix

HD 0:29 / 10:35

Incontinent Diaper Dominatrix

Clips4sale 7 months ago

A Blonde Shemale Punishes The Dirty Ass Of A Dude

A Blonde Shemale Punishes The Dirty Ass Of A Dude

ShemaleSex 3 months ago

Flaming Wax Play on Nipples and Cock

HD 2:00 / 10:17

Flaming Wax Play on Nipples and Cock

Flirt4Free 9 years ago

Elix & Elias & Paulo Private Show

61% HD 2:00 / 5:20

Elix & Elias & Paulo Private Show

Flirt4Free 8 months ago

Punish fucking my slut ass for being naughty

Punish fucking my slut ass for being naughty

FapHouse 3 weeks ago

Troy Khalil Private Show

HD 2:00 / 11:32

Troy Khalil Private Show

Flirt4Free 2 years ago

Izzy Wilde dominates with rough anal sex and BDSM punishment for Colby Jansen

Izzy Wilde dominates with rough anal sex and BDSM punishment for Colby Jansen

Sheshaft 3 months ago

”Courageous Transgender Natalie Mars bends down & lets the giant rubber dick destroy her butthole”

”Courageous Transgender Natalie Mars bends down & lets the giant rubber dick destroy her butthole”

429Men 1 year ago

Slave Olympics and the Punishment Orgy aftermath FullHD

54% HD 0:11 / 23:21

Slave Olympics and the Punishment Orgy aftermath FullHD

Clips4sale 3 years ago

Darksome skinned tgirl punishes a bound up stud with her large

Darksome skinned tgirl punishes a bound up stud with her large

ShemaleSin 1 year ago

Rashel Mendoza Private Show

Rashel Mendoza Private Show

Flirt4Free 5 months ago

TSlut steel bound for FemDom orgasms (MP4 HD 6000kbps)

HD 0:11 / 10:35

TSlut steel bound for FemDom orgasms (MP4 HD 6000kbps)

Clips4sale 1 year ago

Busty tranny boss loves to feel big black cock in her nice butt

Busty tranny boss loves to feel big black cock in her nice butt

XGroovy 2 years ago

Sensually Milking & Edging Trans Cock

63% HD 0:10 / 14:44

Sensually Milking & Edging Trans Cock

LoyalFans 2 years ago

Leonardo & Angel & Johan & Bayron Party on Apr 7, 2024

55% HD 2:00 / 23:21

Leonardo & Angel & Johan & Bayron Party on Apr 7, 2024

Flirt4Free 1 year ago

TS Mistress Dominates Beefy Sub

TS Mistress Dominates Beefy Sub

TransTube.tv 1 month ago

Asian MILF tgirl domina punish fucked her assistant

Asian MILF tgirl domina punish fucked her assistant

Tranny.one 3 years ago

Victoria Rousso Private Show

Victoria Rousso Private Show

Flirt4Free 2 years ago

Beautiful blonde tranny Mel Vogue has a black bull punishing her ass

Beautiful blonde tranny Mel Vogue has a black bull punishing her ass

DrTuber 9 years ago

Brutus K Private Show

Brutus K Private Show

Flirt4Free 6 years ago

Skinny cowgirl Ava Eden punished for trespassing with doggystyle cumshot

Skinny cowgirl Ava Eden punished for trespassing with doggystyle cumshot

XXXShake 4 years ago

Amateur thief Casey Cumz cuffed and punished by trans Venus Luxa

Amateur thief Casey Cumz cuffed and punished by trans Venus Luxa

MenGem 3 months ago

Angela Lelli Private Show

Angela Lelli Private Show

Flirt4Free 2 years ago

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

Year Long Chastity Release Shemale Femdom Foot Worship Anal Pegging and Face Fucking

Eporner 4 months ago

Sissy in Burqa: Height Humiliation and Domination - Candid Session with Goddess Marcy

56% HD 0:25 / 10:57

Sissy in Burqa: Height Humiliation and Domination - Candid Session with Goddess Marcy

Clips4sale 1 year ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 4 years ago

Triple Threat Domination: Liam Idols & Vladicoff Spit-Roast a Begging Sub Slut

HD 0:10 / 27:41

Triple Threat Domination: Liam Idols & Vladicoff Spit-Roast a Begging Sub Slut

LoyalFans 4 months ago

FTM Dom Punishes Nerd With Cock Sucking

FTM Dom Punishes Nerd With Cock Sucking

APClips 1 year ago

Brutus K Private Show

HD 2:00 / 48:58

Brutus K Private Show

Flirt4Free 6 years ago

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

”Tranny Sergeant Jessy Dubai Trains Her New Recruits”

Rainblow 1 year ago

Thirty-Six Needle Clitoris Punishment Masturbator (ES976)

Thirty-Six Needle Clitoris Punishment Masturbator (ES976)

Clips4sale 1 year ago

Dommes in Heels Punish Innocent Trans Catgirl

Premium HD 13:24

Dommes in Heels Punish Innocent Trans Catgirl

Sheer 3 years ago

Punishment must be

Punishment must be

xHamster 1 month ago

The Papi Chulo BBC Fisted Me Deep Until I Came

65% 1:01 / 17:57

The Papi Chulo BBC Fisted Me Deep Until I Came

FapHouse 2 weeks ago

Shemale Chelsea Marie was punished with oral and anal sex in the kitchen by Pierce Paris

Shemale Chelsea Marie was punished with oral and anal sex in the kitchen by Pierce Paris

Eporner 1 year ago

”itsPOV: Pleasure fuck foursome with petite teens Kaisa Nord, Mona Blue & Stefany Kyler”

”itsPOV: Pleasure fuck foursome with petite teens Kaisa Nord, Mona Blue & Stefany Kyler”

ThePornstar 8 months ago

Large shlong police officer Lucy screwing and humiliating chastity sub

Large shlong police officer Lucy screwing and humiliating chastity sub

ShemaleSin 3 weeks ago

Intense Crossdress Session Part 7

Intense Crossdress Session Part 7

Tranny.one 4 years ago

Denali Danger gets Punished #3 trailer shes so fucking sexy! Full video available now!

Denali Danger gets Punished #3 trailer shes so fucking sexy! Full video available now!

aShemaleTube 11 months ago

Sabrina Smiith Private Show

4K 2:00 / 38:59

Sabrina Smiith Private Show

Flirt4Free 1 week ago

Crazy Night

45% HD 2:00 / 32:38

Flirt4Free 3 years ago

Elix & Elias & Paulo Private Show

64% HD 2:00 / 7:41

Elix & Elias & Paulo Private Show

Flirt4Free 8 months ago

”Blonde hides necklace in ass its time to punish her”

”Blonde hides necklace in ass its time to punish her”

TransHero 3 months ago

Avery Angel gets tag teamed and punished

Avery Angel gets tag teamed and punished

aShemaleTube 1 year ago

”Apolonia & Zoe Doll are going to get punished for being wet down their pants”

”Apolonia & Zoe Doll are going to get punished for being wet down their pants”

ThePornstar 1 year ago

Sabrina Smiith Private Show

4K 2:00 / 41:27

Sabrina Smiith Private Show

Flirt4Free 3 months ago

Stepdad gets hard spanking stepdaughter

Stepdad gets hard spanking stepdaughter

Fapcat 2 years ago

Sissy Steph gets Punished by The BBC PUNISHER and takes a HUGE facial cumshot!

Sissy Steph gets Punished by The BBC PUNISHER and takes a HUGE facial cumshot!

aShemaleTube 1 year ago

Jewel Selfsucker Private Show

Jewel Selfsucker Private Show

Flirt4Free 3 years ago

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

HD 1:01 / 13:25

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

FapHouse 6 months ago

Izzi Private Show

Izzi Private Show

Flirt4Free 1 week ago

Brutus K is Playing for His Guest

Brutus K is Playing for His Guest

Flirt4Free 8 years ago

Gamer Girl [Part 1]

4K 0:11 / 15:44

Gamer Girl [Part 1]

Clips4sale 4 years ago

Three shemales punish a tied up dude before cumming on his

Three shemales punish a tied up dude before cumming on his

IcePorn 1 year ago

Desi Indian Step Father Punishes his step Daughter for not to listen him ( Hindi Audio )

Desi Indian Step Father Punishes his step Daughter for not to listen him ( Hindi Audio )

XVideos 1 year ago

Victoria Rousso Private Show

Victoria Rousso Private Show

Flirt4Free 2 years ago

Lucky dude fucks and gets fucked by a bunch of hot trannies

Lucky dude fucks and gets fucked by a bunch of hot trannies

Fapality 1 year ago

Elvis Rey & Andres & Aron Private Show

63% HD 2:00 / 30:59

Elvis Rey & Andres & Aron Private Show

Flirt4Free 3 years ago

Luciana Sainz Private Show

HD 2:00 / 21:17

Luciana Sainz Private Show

Flirt4Free 2 weeks ago

32 33 34 35 36

40,584 results found

Narrow your search

slave punishment spanking punishment bbc punishment punishment anal anal punishment punishment gangbang self punishment cruel punishment strapon punishment enema punishment rough punishment corporal punishment pegging punishment anal bbc punishment mom punishment gangbang punishment bdsm punishment stepdaughter punishment pornstar punishment diaper punishment

Categories Pornstars

Categories Pornstars

PornMD: A Porn Search Engine.

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.