Punishment Videos (59,611)

Shemale Mafia Punish Poor Girl

Shemale Mafia Punish Poor Girl

Wankoz 1 week ago

Pimp and prostitute-shemale punished prostitute-rival

Pimp and prostitute-shemale punished prostitute-rival

AShemaleTube 8 years ago

Blonde White Femboy Milking her Nipples and Slapping them with Big Dildo

Blonde White Femboy Milking her Nipples and Slapping them with Big Dildo

XHamster 6 months ago

Vibrator Ruining in Nylon Catsuit

68% HD 0:10 / 14:52

Vibrator Ruining in Nylon Catsuit

Clips4sale 4 years ago

Peepers Punishment Is Punished By Shecock - Ts Foxxy

Peepers Punishment Is Punished By Shecock - Ts Foxxy

AbTranny 10 months ago

BITCH STEPMOM Makes her Fem Pussy HOUSEBOY Vacuum then turns him into her Footrest

BITCH STEPMOM Makes her Fem Pussy HOUSEBOY Vacuum then turns him into her Footrest

XHamster 1 week ago

Watch these tattooed babes get their asses drilled in this bareback compilation of wishful thinking and anal punishment

Watch these tattooed babes get their asses drilled in this bareback compilation of wishful thinking and anal punishment

TrannyMovs 1 week ago

Breaking Ts Jasmine Lotus: Chasity Slut Punished & Covered in Cum

59% 0:30 / 16:29

Breaking Ts Jasmine Lotus: Chasity Slut Punished & Covered in Cum

Clips4sale 10 months ago

Ts Vaniity and Mia Isabella dominate and punish thieves with their massive cocks in a group fuck

Ts Vaniity and Mia Isabella dominate and punish thieves with their massive cocks in a group fuck

Eporner 7 months ago

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

Big booty Femboy Raven Wedgie and Big Anal Gape with Inflatable Dildo

XHamster 5 months ago

Skinny shemale with big round boobs slams her cock in a tight ass

Skinny shemale with big round boobs slams her cock in a tight ass

Tranny.one 4 years ago

Sissy Teased by Mistress's Strapon

Sissy Teased by Mistress's Strapon

FapHouse 2 weeks ago

Anitta's Addiction

Anitta's Addiction

Some.Porn 1 year ago

Venezuelan friend with good cock of 23cm eating chicken ass Bogota Clip 1

Venezuelan friend with good cock of 23cm eating chicken ass Bogota Clip 1

XHamster 1 month ago

LACED #39 Preview! (SADISM & MASOCHISM ASMR) Jizz Hatch Femboy Puppy Punished & Milked! (Utter:LaceVoid,com)

LACED #39 Preview! (SADISM & MASOCHISM ASMR) Jizz Hatch Femboy Puppy Punished & Milked! (Utter:LaceVoid,com)

GayCK 4 years ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

XHamster 9 months ago

Humiliated

XHamster 2 years ago

Black tranny domina punishes a guy's anus hard

Black tranny domina punishes a guy's anus hard

AShemaleTube 10 months ago

Female and tranny dominate two slaves

Female and tranny dominate two slaves

Fetishpapa 4 months ago

Punishing My Cock with My Sandals and I Cumi on Them, and I Lick My Cum

Punishing My Cock with My Sandals and I Cumi on Them, and I Lick My Cum

FapHouse 2 days ago

Stepdaddy Catches His Horny Sissy Girl

54% HD 1:01 / 10:53

Stepdaddy Catches His Horny Sissy Girl

FapHouse 10 months ago

Femdom Anal Annihilation: 60-Minutes of Giant Strap-on Pegging & Deep Fisting Full-Length (1080p)

54% HD 0:30 / 1:04:09

Femdom Anal Annihilation: 60-Minutes of Giant Strap-on Pegging & Deep Fisting Full-Length (1080p)

Clips4sale 2 years ago

Stepdaddy and little shemale brat Chelsea Marie

Stepdaddy and little shemale brat Chelsea Marie

Eporner 2 years ago

Shut Up! Im Going To Sit On Your Face And Cum! - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 35 MINUTES FOR US$ 19,99!

61% HD 0:11 / 34:55

Shut Up! Im Going To Sit On Your Face And Cum! - FULL VERSION - FULL HD QUALITY (1920 X 1080) MP4 VIDEO FILE - SPECIAL PRICE: 35 MINUTES FOR US$ 19,99!

Clips4sale 2 years ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

69% HD 0:39 / 49:11

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

FapHouse 7 months ago

ATS Avery Angel Gets Punished #2 Shes so sexy 😍

ATS Avery Angel Gets Punished #2 Shes so sexy 😍

AShemaleTube 3 months ago

Alice Kizar Private Show

55% 4K 2:00 / 7:37

Alice Kizar Private Show

Camster 3 weeks ago

Hard Cash Payback!

Hard Cash Payback!

XHamster 1 year ago

Pliant a.i. - Hawt Ryder Monroe Is Punished by Cynical Scientist

Pliant a.i. - Hawt Ryder Monroe Is Punished by Cynical Scientist

ShemaleSin 6 months ago

Hot shemale punisher in black fishnets gives a massive

Hot shemale punisher in black fishnets gives a massive

XHamster 2 years ago

Tranny Addiction 4

52% HD 0:30 / 2:02:00

Tranny Addiction 4

AEBN 8 years ago

Sophie Fantasy Private Show

61% HD 2:00 / 31:39

Sophie Fantasy Private Show

Flirt4Free 3 weeks ago

”T-girl Kate Zoha punishes Korra Del Rio with deep rough fucking”

”T-girl Kate Zoha punishes Korra Del Rio with deep rough fucking”

TransHero 1 year ago

Aleex & Paulo Private Show

52% HD 2:00 / 8:12

Aleex & Paulo Private Show

Flirt4Free 1 year ago

Cute Big Tits Trans Girl in Caulifla Cosplay Pumping and Punishing her Tits with Vacuum Milking Machine and Lactation

Cute Big Tits Trans Girl in Caulifla Cosplay Pumping and Punishing her Tits with Vacuum Milking Machine and Lactation

XHamster 1 month ago

frenchbaguettes-yaya-the-punisher

frenchbaguettes-yaya-the-punisher

KeekAss 2 years ago

Soft eggs for breakfast... Ballbusting until cumshot! CBT by cute Tranny Girl

Soft eggs for breakfast... Ballbusting until cumshot! CBT by cute Tranny Girl

XHamster 1 year ago

I Want to Have You Below Me

HD 2:00 / 19:48

I Want to Have You Below Me

Flirt4Free 7 years ago

Sophia Loreen Private Show

4K 2:00 / 45:37

Sophia Loreen Private Show

Flirt4Free 5 days ago

Sexy strip, twerk naked, playing with my nipples and with my pussy, lets play with my dildo and make me wet!!

Sexy strip, twerk naked, playing with my nipples and with my pussy, lets play with my dildo and make me wet!!

Flirt4Free 4 years ago

Rough anal treatment for Tranny Sabina

Rough anal treatment for Tranny Sabina

Tranny.one 4 years ago

Obedient Shemale Slave Fully Trained for Extreme Anal Punishment

Obedient Shemale Slave Fully Trained for Extreme Anal Punishment

JapaneseMatures 3 years ago

Camila & Samael Private Show

77% HD 2:00 / 22:30

Camila & Samael Private Show

Flirt4Free 1 year ago

Face sitting punishment Fuck my ass, pulverize my head EXTREME!

Face sitting punishment Fuck my ass, pulverize my head EXTREME!

Eporner 2 years ago

”Blindfolded strapped & public banged”

”Blindfolded strapped & public banged”

TransHero 7 months ago

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

TS Foxxy Punishes Slob Boyfriend with Spanking & Nonstop Pounding!

XHamster 2 months ago

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

45% HD 2:00 / 4:52

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

Flirt4Free 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 5 months ago

thaysa carvalho (ts) fucked hard by white boyfriend

thaysa carvalho (ts) fucked hard by white boyfriend

PornOne 4 years ago

Dominant tranny punishes her boytoy with her massive Tcock

Dominant tranny punishes her boytoy with her massive Tcock

BeMyHole 6 years ago

Nvh-055 Transsexual Bondage Training Lesbian Female Teacher Punishes Student 18+ As Extracurricular Lesson Suzune Nico/arimura Nozomi

Nvh-055 Transsexual Bondage Training Lesbian Female Teacher Punishes Student 18+ As Extracurricular Lesson Suzune Nico/arimura Nozomi

GetTranny 11 months ago

Cleaning Lady Gets Dirty

Cleaning Lady Gets Dirty

Some.Porn 9 months ago

Sophia Loreen Private Show

71% HD 2:00 / 16:24

Sophia Loreen Private Show

Flirt4Free 1 year ago

The League of Extraordinary Transsexuals: The Final Punishment

The League of Extraordinary Transsexuals: The Final Punishment

AbTranny 10 years ago

La Cherry Spice, Dorian

La Cherry Spice, Dorian

XHamster 1 year ago

Jessica Host Dominates Bound Man Hardcore Anal Sex Rough Domination

Jessica Host Dominates Bound Man Hardcore Anal Sex Rough Domination

Sheshaft 6 months ago

Sophia Loreen Private Show

62% HD 2:00 / 8:41

Sophia Loreen Private Show

Flirt4Free 2 months ago

Hanna Ven Private Show

54% HD 2:00 / 2:17:23

Hanna Ven Private Show

Flirt4Free 2 years ago

Sophia Loreen Party on Jul 23, 2026 - Part 4

HD 2:00 / 13:47

Sophia Loreen Party on Jul 23, 2026 - Part 4

Camster 1 week ago

girlfriend lily cheating on me mounts my cock before her boyfriend arrives to satiate his desires, hard sex submissive girlfriend, fetish doll

girlfriend lily cheating on me mounts my cock before her boyfriend arrives to satiate his desires, hard sex submissive girlfriend, fetish doll

XHamster 1 month ago

Sophie Fantasy Private Show

HD 2:00 / 27:48

Sophie Fantasy Private Show

Flirt4Free 1 week ago

The Reward for the Locked-up Sissy

The Reward for the Locked-up Sissy

XHamster 8 months ago

Toxic male ***: dominated & made to eat trans girl ass

HD 1:01 / 21:17

Toxic male ***: dominated & made to eat trans girl ass

FapHouse 4 years ago

cherry and i dominate our disobedient puppies nyxi and livi

41% HD 0:30 / 33:02

cherry and i dominate our disobedient puppies nyxi and livi

AnalVids 1 year ago

lizzy laynez punished lizzy laines

lizzy laynez punished lizzy laines

PornOne 2 years ago

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

TS Kate Zoha punishes Korra Del Rio with deep rough fucking

KeekAss 1 year ago

FilthyPov - CAUGHT Sniffing Her Panties, Busty Stepmom Punished Me By Riding My Cock

FilthyPov - CAUGHT Sniffing Her Panties, Busty Stepmom Punished Me By Riding My Cock

Some.Porn 1 year ago

Slap My Horny Ass ^^

Slap My Horny Ass ^^

Camster 1 year ago

Blue Skinned Succubus Has Booty Destroyed By Futa Arch Demon - Futa - CG Porn

Blue Skinned Succubus Has Booty Destroyed By Futa Arch Demon - Futa - CG Porn

ShemaleSin 17 hours ago

TS Yoga Instructor Dominates Foot-Sniffer

TS Yoga Instructor Dominates Foot-Sniffer

AShemaleTube 10 years ago

Sophia Loreen Private Show

68% HD 2:00 / 6:30

Sophia Loreen Private Show

Flirt4Free 3 months ago

Pink Latex Shebabe Punishes Her Bf

Pink Latex Shebabe Punishes Her Bf

BeMyHole 1 month ago

You were a bad boy! As a punishment, punch yourself while jerking off! JOI CBT GERMAN

You were a bad boy! As a punishment, punch yourself while jerking off! JOI CBT GERMAN

XHamster 1 year ago

Mike Swift & David Golden Private Show

HD 2:00 / 10:37

Mike Swift & David Golden Private Show

Flirt4Free 1 day ago

Marian & Richard Private Show

58% HD 2:00 / 1:56:58

Marian & Richard Private Show

Flirt4Free 1 month ago

A Perfect Punish - Morgan Bailey, Alex Ander And Alexander Gustavo

A Perfect Punish - Morgan Bailey, Alex Ander And Alexander Gustavo

AbTranny 2 years ago

TS Kendall Penny dominates Bussy Bradley with pornx BDSM

TS Kendall Penny dominates Bussy Bradley with pornx BDSM

Pornicom 1 year ago

West Wing Porn - the Dirtiest Business of All - Politics

West Wing Porn - the Dirtiest Business of All - Politics

FreePorn8 2 weeks ago

Trans Maid Kaela Luna Wants To Be Used By Her New Boss

64% HD 0:30 / 31:40

Trans Maid Kaela Luna Wants To Be Used By Her New Boss

Clips4sale 11 months ago

My Pink Fantassy! Veronica Vixen Punishes Gracie Jane at GenderFlux

My Pink Fantassy! Veronica Vixen Punishes Gracie Jane at GenderFlux

Xshemale 10 months ago

Painfully decorated and stuffed

Painfully decorated and stuffed

XHamster 2 years ago

Jenny Wei is BACK! Jenny gets fucked by The BBC PUNISHER full video available now 😈

Jenny Wei is BACK! Jenny gets fucked by The BBC PUNISHER full video available now 😈

AShemaleTube 1 year ago

Big Booty TS Esther gets fucked by the BBC PUNISHER and Facialed

Big Booty TS Esther gets fucked by the BBC PUNISHER and Facialed

AShemaleTube 5 months ago

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

69% HD 1:01 / 15:56

Full Version of Dia De Muertos Mummy Pumps and Punishes Her Lactating Nipples with a Vacuum Machine

FapHouse 8 months ago

FEMINIZED - Rubber Maid Punishment (Natalie Mars, Shiri

FEMINIZED - Rubber Maid Punishment (Natalie Mars, Shiri

IcePorn 1 year ago

Lesbian Seeks TGirl

63% HD 0:30 / 1:46:00

Lesbian Seeks TGirl

AEBN 6 years ago

Sophia Loreen Private Show

63% HD 2:00 / 18:12

Sophia Loreen Private Show

Camster 1 month ago

Jenny Wei Gets Punished #3

Jenny Wei Gets Punished #3

AShemaleTube 6 months ago

Sophia Loreen Private Show

62% HD 2:00 / 31:53

Sophia Loreen Private Show

Flirt4Free 2 months ago

Cute Femboy Lactating her Tits after Punishing her Nipples with Dildo, Clamps and Vacuum Milking Machine Clip 2

Cute Femboy Lactating her Tits after Punishing her Nipples with Dildo, Clamps and Vacuum Milking Machine Clip 2

XHamster 4 months ago

Whipping Punishment for the Sissy Slut - Part 2

Whipping Punishment for the Sissy Slut - Part 2

XHamster 3 months ago

West Wing Porn - the Dirtiest Business of All - Politics

West Wing Porn - the Dirtiest Business of All - Politics

SortPorn 2 weeks ago

Pride and Orifice Part 2

Premium HD 30:35

Pride and Orifice Part 2

TransAngels 3 years ago

Step mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min - Teaser Video

Step mommy Dom Jessica Bloom Babies And Punishes Bratty Girl Jenby (short Version) 24 Min - Teaser Video

GetTranny 3 years ago

Italian tranny Anna Hickiman punishes wardrobe attendant

66% HD 1:01 / 46:46

Italian tranny Anna Hickiman punishes wardrobe attendant

FapHouse 3 years ago

Anal punishment and pleasure for sexy Japanese shemale

Anal punishment and pleasure for sexy Japanese shemale

PornLib 1 year ago

punished in place 2: featuring livi doll

66% HD 0:30 / 27:39

punished in place 2: featuring livi doll

AnalVids 2 years ago

Sophia Loreen Party on Jul 28, 2026 - Part 2

4K 2:00 / 51:31

Sophia Loreen Party on Jul 28, 2026 - Part 2

Camster 6 days ago

Punishment enema Some of these pigs just don't get it.

Punishment enema Some of these pigs just don't get it.

Tranny.one 4 years ago

Perfect Ass for the Job

66% HD 0:10 / 5:23

Perfect Ass for the Job

LoyalFans 1 year ago

Futa Punishes Her Step-slut

47% 1:01 / 19:11

Futa Punishes Her Step-slut

FapHouse 5 months ago

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

59% HD 1:01 / 9:37

Shemale on Balcony Outdoor Fisting Punishment - Obeyladymk Catches Jasmine Dlight Smoking and Fists Me Outdoors

FapHouse 1 year ago

Aub Kat - Wife Punishes You

Aub Kat - Wife Punishes You

Eporner 1 year ago

Punishment Transexual (Full porn movie)

Punishment Transexual (Full porn movie)

XHamster 9 months ago

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

58% HD 0:30 / 15:21

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

AnalVids 8 months ago

MILF Librarian Punishes TS Delinquent

MILF Librarian Punishes TS Delinquent

AShemaleTube 11 years ago

Punishing You Makes Stepmom's Cock Grow - Ft Imilia Audley

46% HD 0:28 / 27:25

Punishing You Makes Stepmom's Cock Grow - Ft Imilia Audley

Clips4sale 1 year ago

Another Long Night of Slow, Sadistic Punishment

Another Long Night of Slow, Sadistic Punishment

FapHouse 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Camster 1 day ago

Wearing to cross dress

Wearing to cross dress

XHamster 1 year ago

Sexxxy Jaide punishes boy friend

Sexxxy Jaide punishes boy friend

AShemaleTube 4 years ago

Viky & Master Private Show

58% HD 2:00 / 14:39

Viky & Master Private Show

Flirt4Free 11 months ago

Latex TS Queens Dominate Their Subs

Latex TS Queens Dominate Their Subs

Xozilla 2 months ago

BDSM and fist for crossdresser

BDSM and fist for crossdresser

Fetishpapa 8 months ago

Hairy hunk with a big cock gets a hot creampie after getting caught in the act

Hairy hunk with a big cock gets a hot creampie after getting caught in the act

GayVD 2 months ago

Leya Falcon punishes Aphrodite Adams with massive strap on

Leya Falcon punishes Aphrodite Adams with massive strap on

Fapnado 1 month ago

Severe punishment for Bella to teach her who’s the Boss.

HD 0:10 / 10:40

Severe punishment for Bella to teach her who’s the Boss.

LoyalFans 3 weeks ago

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

Chastity Sissy Slut Training - Jessica Bloom Huge Anal Orgasm

XHamster 2 years ago

Moreno sends video masturbating to wives

Moreno sends video masturbating to wives

XHamster 3 years ago

Spanked by the Mean Sex Fiends!

Spanked by the Mean Sex Fiends!

Some.Porn 3 days ago

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