Punishment Videos (38,635)

Latex maid Lisa gets a worthwhile thrashing and thrashing from tranny Mistresse Lucy

Latex maid Lisa gets a worthwhile thrashing and thrashing from tranny Mistresse Lucy

MatureTubeHere 1 year ago

Sophie Fantasy Private Show

56% HD 2:00 / 4:35

Sophie Fantasy Private Show

Flirt4Free 1 year ago

trans domme beats and fucks ftm in pillory - jaq quicksilver and cherry mavrik - mtf dominatrix puts trans man in bondage for punishment - t4t, stocks, bdsm, ts, spanking, facefuck

HD 0:28 / 25:05

trans domme beats and fucks ftm in pillory - jaq quicksilver and cherry mavrik - mtf dominatrix puts trans man in bondage for punishment - t4t, stocks, bdsm, ts, spanking, facefuck

PornBox 11 months ago

Ebony tranny domina punishes her bf in the kitchen

Ebony tranny domina punishes her bf in the kitchen

aShemaleTube 3 weeks ago

''When I See A Hard Dick I Want To Suck It!'' - GenderXFilms - Angelina Teenmodels

''When I See A Hard Dick I Want To Suck It!'' - GenderXFilms - Angelina Teenmodels

Rock.PORN 11 months ago

Curvy inked tranny punishes her best friend

Curvy inked tranny punishes her best friend

Eporner 3 years ago

Elvis Rey & Andres & Aron Private Show

63% HD 2:00 / 23:08

Elvis Rey & Andres & Aron Private Show

Flirt4Free 2 years ago

Trix Bell Private Show

Trix Bell Private Show

Flirt4Free 5 months ago

HOTTEST CUMSHOW

HOTTEST CUMSHOW

Flirt4Free 1 year ago

Sophia Loreen Private Show

66% HD 2:00 / 13:38

Sophia Loreen Private Show

Flirt4Free 6 months ago

Sophia Loreen Party on May 24, 2025 - Part 2

65% 4K 2:00 / 25:52

Sophia Loreen Party on May 24, 2025 - Part 2

Flirt4Free 7 months ago

Master & Ithan Private Show

56% HD 2:00 / 17:23

Master & Ithan Private Show

Flirt4Free 5 months ago

Irina Royce Private Show

Irina Royce Private Show

Flirt4Free 1 year ago

Elias & Elix Private Show

52% HD 2:00 / 16:27

Elias & Elix Private Show

Flirt4Free 4 months ago

Priscilla makes her slave happy with her hard cock

Priscilla makes her slave happy with her hard cock

xHamster 1 year ago

Tiffanny Lombardi Private Show

66% HD 2:00 / 4:26

Tiffanny Lombardi Private Show

Flirt4Free 2 years ago

Tovez Private Show

67% HD 2:00 / 36:59

Tovez Private Show

Flirt4Free 1 year ago

Part 4:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

Part 4:- Lamista Bear, Domina Satana, Allegro and Satana's Butler

xHamster 3 months ago

Jhordy & Maxx Private Show

65% HD 2:00 / 1:24:58

Jhordy & Maxx Private Show

Flirt4Free 5 months ago

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

69% HD 1:01 / 19:41

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

FapHouse 1 month ago

26mins (FULL) Five Mistresses and One Boytoy

26mins (FULL) Five Mistresses and One Boytoy

xHamster 10 months ago

Schwangere holt sich Callboy

Schwangere holt sich Callboy

Tranny.one 3 years ago

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

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

StarWank 7 months ago

Bbc Punishments

Bbc Punishments

Eporner 1 month ago

Butt Slut Bootcamp: Latina Dommes Pegging & CEI Challenge

68% HD 0:39 / 26:17

Butt Slut Bootcamp: Latina Dommes Pegging & CEI Challenge

FapHouse 1 month ago

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Premium HD 33:02

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Sheer 1 year ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 3 weeks ago

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

Yasmin Lee Devastatingly Gorgeous Secretary Punishes Sexist Boss Pig!

AbTranny 6 months ago

Master & Ithan & Aleex Private Show

52% HD 2:00 / 38:32

Master & Ithan & Aleex Private Show

Flirt4Free 6 months ago

Euro Model, Brutus Plays with His Dick

53% HD 2:00 / 27:12

Euro Model, Brutus Plays with His Dick

Flirt4Free 10 years ago

Liz Rainbow Rough Fucking and Squirting by Crossdresser Perverted Freak

Liz Rainbow Rough Fucking and Squirting by Crossdresser Perverted Freak

xHamster 1 year ago

Threeway Punishment

Threeway Punishment

aShemaleTube 13 years 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

Thicc juicy bbq

Thicc juicy bbq

FapCat 1 year ago

The Pantyhose Show

56% HD 2:00 / 5:29

The Pantyhose Show

Flirt4Free 2 years ago

Trans Gal Worships His Trans Wang In advance of This guy Wrecks Her Butt

Trans Gal Worships His Trans Wang In advance of This guy Wrecks Her Butt

Lesbian8 1 month ago

Sophia Loreen Private Show

68% HD 2:00 / 16:24

Sophia Loreen Private Show

Flirt4Free 6 months ago

Punishing my balls and dick huge cumshot

Punishing my balls and dick huge cumshot

aShemaleTube 5 months ago

Sock Worship Roleplay

HD 2:00 / 11:49

Sock Worship Roleplay

Flirt4Free 7 years ago

Slave rental

xHamster 8 months ago

Kitty Kunt and her huge she cock

70% HD 1:01 / 22:55

Kitty Kunt and her huge she cock

FapHouse 3 years ago

Your Pink Punishment Walk Home

Your Pink Punishment Walk Home

LoyalFans 2 years ago

Viky & Master Private Show

52% HD 2:00 / 7:04

Viky & Master Private Show

Flirt4Free 1 month ago

Richii Smiith Private Show

4K 2:00 / 13:28

Richii Smiith Private Show

Flirt4Free 1 week ago

4 cocks pegging gangbang to punish naughty students

64% HD 0:10 / 13:00

4 cocks pegging gangbang to punish naughty students

LoyalFans 9 months 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 4 months ago

Hot Teasing with My Boobs

Hot Teasing with My Boobs

Flirt4Free 8 months ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 5 months ago

Elix & Master & Aleex Private Show

59% HD 2:00 / 37:17

Elix & Master & Aleex Private Show

Flirt4Free 5 months ago

Growing Into a Slut - MILF Step-Mommy Sydney Screams Punishes Slut TS Step-Daughter Sammi Smith

Premium HD 20:29

Growing Into a Slut - MILF Step-Mommy Sydney Screams Punishes Slut TS Step-Daughter Sammi Smith

XVideosRed 1 year ago

shemale mistress in high heeled boots punishes her slave by destroying his ass

shemale mistress in high heeled boots punishes her slave by destroying his ass

PornBox 2 years ago

Master & Ithan & Aleex Private Show

41% HD 2:00 / 33:20

Master & Ithan & Aleex Private Show

Flirt4Free 5 months ago

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

HD 0:39 / 16:04

Big Tits Sissy with Asuka Cosplay Pumps and Punishes Her Puffy Nipples

FapHouse 3 weeks ago

A Disgrace to Our Town Part 1

A Disgrace to Our Town Part 1

xHamster 9 months ago

Runaway Punished with spitroast + left leaking tgirls cum

65% HD 0:10 / 13:00

Runaway Punished with spitroast + left leaking tgirls cum

LoyalFans 1 year ago

My Nipples So Hard^^

My Nipples So Hard^^

Flirt4Free 9 months ago

Shiri Allwood - Isabella Sorrenti Punishes Peeping Shiri

Shiri Allwood - Isabella Sorrenti Punishes Peeping Shiri

TubeOn 1 year ago

you were meant to be a girl: loving feminization and pov bj - full video on Veggiebabyy Manyvids

you were meant to be a girl: loving feminization and pov bj - full video on Veggiebabyy Manyvids

xHamster 7 months ago

Exotic Sophia Loreen in Pvt Pumps Pussy and Rides Cock

HD 2:00 / 35:35

Exotic Sophia Loreen in Pvt Pumps Pussy and Rides Cock

Flirt4Free 3 years ago

”Hot shemale Cassidy Quinn spanked hard & diapered”

”Hot shemale Cassidy Quinn spanked hard & diapered”

Fapnow 1 year ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

xHamster 2 months ago

Master & Christian & Nicco Private Show

50% HD 2:00 / 14:59

Master & Christian & Nicco Private Show

Flirt4Free 1 year ago

Luccas & Jhordy & Master Private Show

42% HD 2:00 / 1:13:44

Luccas & Jhordy & Master Private Show

Flirt4Free 7 months ago

”Hardcore sex in a dungeon with shemale punishment”

”Hardcore sex in a dungeon with shemale punishment”

Trashreality 1 year ago

Hpt Cumshoot on Me^^

Hpt Cumshoot on Me^^

Flirt4Free 7 months ago

Feelipe & Adara Private Show

53% HD 2:00 / 8:50

Feelipe & Adara Private Show

Flirt4Free 4 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 4 weeks ago

Mary & Polly Private Show

55% 4K 2:00 / 6:05

Mary & Polly Private Show

Flirt4Free 7 months ago

Topping Emma Rose

55% HD 0:10 / 20:34

Topping Emma Rose

LoyalFans 2 days ago

Trans Mistress Foxxy Trains Submissive Sherman Maus With BDSM Fisting And Huge Cock

Trans Mistress Foxxy Trains Submissive Sherman Maus With BDSM Fisting And Huge Cock

Eporner 1 month ago

Christian & Nicco & Elvis Private Show

41% HD 2:00 / 19:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

EvilWoman: TS slut destroyed with huge dildo

64% 0:31 / 11:28

EvilWoman: TS slut destroyed with huge dildo

Clips4sale 2 weeks ago

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

72% HD 0:10 / 16:19

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

LoyalFans 3 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 8 months ago

house maid Slave boy punishing with cadle

house maid Slave boy punishing with cadle

xHamster 8 months ago

Tranny nun punishing anal male prisoner

Tranny nun punishing anal male prisoner

aShemaleTube 6 years ago

Step Mom Punishment Her Son With Bondage Sex | Uncensored Hentai

Step Mom Punishment Her Son With Bondage Sex | Uncensored Hentai

W4NKR 5 months ago

Gorgeous TS babe Venus Lux anal pounds her slutty teacher aide

Gorgeous TS babe Venus Lux anal pounds her slutty teacher aide

UrGayPorn 7 months ago

Sophia Loreen Party on Dec 14, 2025 - Part 3

4K 2:00 / 46:18

Sophia Loreen Party on Dec 14, 2025 - Part 3

Flirt4Free 1 month ago

”Babe gang bang ravaged at public gallery”

”Babe gang bang ravaged at public gallery”

TransHero 1 month ago

Trans Babysitter Gets taught a lesson by HOT milf

Trans Babysitter Gets taught a lesson by HOT milf

xHamster 4 years ago

Big Tits Submissive Russian Slut Returns For Ass Eating & Rough Sex

Big Tits Submissive Russian Slut Returns For Ass Eating & Rough Sex

FapCat 9 months ago

Master & Ithan & Aleex Private Show

55% HD 2:00 / 31:36

Master & Ithan & Aleex Private Show

Flirt4Free 5 months ago

Shiri Allwood - Gets Punished

Shiri Allwood - Gets Punished

AbTranny 2 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 1 year ago

Leela's Thanksgiving Day Dinner

59% HD 1:01 / 21:36

Leela's Thanksgiving Day Dinner

FapHouse 2 years ago

Wearing to cross dress

Wearing to cross dress

xHamster 1 year ago

”Kendra Sunderland's Deserved Punishment”

”Kendra Sunderland's Deserved Punishment”

TransHero 3 weeks ago

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

Stupid sissy slut take the dick inside throat and suffers humiliated like a good girl

xHamster 1 year ago

Master & Ithan Private Show

41% HD 2:00 / 12:09

Master & Ithan Private Show

Flirt4Free 6 months 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

futa nurse pegging part 4: double Dommed, punished, facialed

57% 0:10 / 29:52

futa nurse pegging part 4: double Dommed, punished, facialed

APClips 7 months ago

Master & Ithan Private Show

54% HD 2:00 / 4:56

Master & Ithan Private Show

Flirt4Free 8 months ago

Trans JOI Punishing With My Real Cock with VibeWithMommy

Premium HD 10:55

Trans JOI Punishing With My Real Cock with VibeWithMommy

XVideosRed 2 years ago

Pretty Ebony TS Cheerleader TRA Punished & Rewarded Deep

Pretty Ebony TS Cheerleader TRA Punished & Rewarded Deep

Eporner 3 days ago

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

54% 1:01 / 17:35

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

FapHouse 2 years ago

”Francesca Le eats her maid out”

”Francesca Le eats her maid out”

ThePornstar 1 year ago

Feelipe & Adara Private Show

72% HD 2:00 / 7:06

Feelipe & Adara Private Show

Flirt4Free 6 months ago

Elix & Elias & Paulo Private Show

44% HD 2:00 / 5:24

Elix & Elias & Paulo Private Show

Flirt4Free 6 months 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

Jenny Wei gets fucked by The BBC PUNISHER! Full 20 min video available now 😈

Jenny Wei gets fucked by The BBC PUNISHER! Full 20 min video available now 😈

aShemaleTube 8 months 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

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

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliation, Gapes.)

Two Very Horny BBC Took Punishes And Fuck The Cute TS MARCELA DIMOV (Interracial, BBC, DAP, Humiliation, Gapes.)

Interracial 1 year ago

sissy vampire punishes visitor

sissy vampire punishes visitor

aShemaleTube 1 year ago

Trap revealed but still fucked by the two black thugs

Trap revealed but still fucked by the two black thugs

Tranny.one 3 years ago

Cum Eating with Your Kitty

Cum Eating with Your Kitty

Flirt4Free 11 months ago

Owen & Ronaldo & Patric Private Show

48% HD 2:00 / 14:02

Owen & Ronaldo & Patric Private Show

Flirt4Free 2 years ago

Alexander Gustavo loves his lustful punishment from TS Morgan Bailey

Alexander Gustavo loves his lustful punishment from TS Morgan Bailey

VikiPorn 5 months ago

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

47% 0:39 / 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

You are punished by futa cops after breaking the law - Futa Joi ( Anal destruction )

You are punished by futa cops after breaking the law - Futa Joi ( Anal destruction )

XVideos 9 months ago

Busty Patricia Bysmark gets her big cock sucked by a dude in

Busty Patricia Bysmark gets her big cock sucked by a dude in

xHamster 11 months ago

Whips and Feet (HD)

63% HD 0:30 / 12:26

Whips and Feet (HD)

Clips4sale 9 months ago

Julia Winston tops her lover

66% HD 1:01 / 31:03

Julia Winston tops her lover

FapHouse 4 years ago

Sophia Loreen Private Show

48% HD 2:00 / 10:53

Sophia Loreen Private Show

Flirt4Free 3 years ago

Orianna Dunn Private Show

45% HD 2:00 / 4:33

Orianna Dunn Private Show

Flirt4Free 2 years ago

Sensually Milking & Edging Trans Cock

73% 0:25 / 14:43

Sensually Milking & Edging Trans Cock

Clips4sale 1 year ago

Sophia Loreen Private Show

60% 4K 2:00 / 58:12

Sophia Loreen Private Show

Flirt4Free 6 months ago

Ballbusting Triangle: Goddess Lilith, Ava Venom, double ballbusting

65% HD 0:10 / 7:11

Ballbusting Triangle: Goddess Lilith, Ava Venom, double ballbusting

LoyalFans 1 year ago

Trans Girl Receives Atomic Wedgie, CBT and Hard Spank. Ft Lucia Skywalker & Xfoxxylady

66% HD 1:01 / 14:12

Trans Girl Receives Atomic Wedgie, CBT and Hard Spank. Ft Lucia Skywalker & Xfoxxylady

FapHouse 5 months ago

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