Punishment Videos (40,288)

”Tied up teen gets merciless punishment she secretly enjoys”

”Tied up teen gets merciless punishment she secretly enjoys”

ThePornstar 1 year ago

Large shlong police officer Lucy screwing and humiliating chastity sub

Large shlong police officer Lucy screwing and humiliating chastity sub

ShemaleSin 2 days ago

Sophia Loreen Party on Feb 27, 2026 - Part 3

60% 4K 2:00 / 15:19

Sophia Loreen Party on Feb 27, 2026 - Part 3

Flirt4Free 5 days ago

crossdresser punished

crossdresser punished

Eporner 2 years ago

Sabrisse and Jia Lissa in wild lesbian 69 with trimmed pussy and high heels

Sabrisse and Jia Lissa in wild lesbian 69 with trimmed pussy and high heels

Some.Porn 2 years ago

Slim Domina Pegs a Sissy Femboy For Wearing Her Panties And Milks His Cock Till He Drains His Balls

Slim Domina Pegs a Sissy Femboy For Wearing Her Panties And Milks His Cock Till He Drains His Balls

XGroovy 2 years ago

Big Dick Trans Mommy Cumming and Milking her Tits

Big Dick Trans Mommy Cumming and Milking her Tits

xHamster 3 months ago

Angel Joseph Private Show

Angel Joseph Private Show

Flirt4Free 1 week ago

Trans Beauty Worships His Trans Dick Previous to That guy Wrecks Her Butt

Trans Beauty Worships His Trans Dick Previous to That guy Wrecks Her Butt

FreePorn8 2 months ago

Futa Step-Sis’s Belly Perv Punishment Feat Aria Nicole 4K

4K 0:10 / 19:56

Futa Step-Sis’s Belly Perv Punishment Feat Aria Nicole 4K

LoyalFans 4 months ago

Luccas & Jhordy & Master Private Show

61% HD 2:00 / 14:28

Luccas & Jhordy & Master Private Show

Flirt4Free 3 weeks ago

Nikolly Gaucha punishes his partner

Nikolly Gaucha punishes his partner

xHamster 1 year ago

Jennifer Jen Private Show

4K 2:00 / 2:54:19

Jennifer Jen Private Show

Flirt4Free 6 days ago

winter bluu sock wrestling loser gets punished

winter bluu sock wrestling loser gets punished

Tranny.one 3 years ago

Elix & Elias & Paulo Private Show

46% HD 2:00 / 11:00

Elix & Elias & Paulo Private Show

Flirt4Free 7 months ago

Even though we had too much time to keep my body warm

Even though we had too much time to keep my body warm

xHamster 3 weeks ago

Peepers Punishment Is Punished By Shecock - Ts Foxxy

Peepers Punishment Is Punished By Shecock - Ts Foxxy

AbTranny 5 months ago

”Tatted babe punishes Girlfriend for cheating”

”Tatted babe punishes Girlfriend for cheating”

TransHero 2 months ago

TS Jesse Punishes A Cis and Trans Man

TS Jesse Punishes A Cis and Trans Man

aShemaleTube 7 years ago

Red lingeried domina ts punishing her bf

Red lingeried domina ts punishing her bf

aShemaleTube 1 month ago

Two friends humiliate and punish a sissy

Two friends humiliate and punish a sissy

aShemaleTube 2 years ago

BDSM and fist for crossdresser

BDSM and fist for crossdresser

Fetishpapa 3 months ago

Luccas & Jhordy & Master Private Show

58% HD 2:00 / 12:04

Luccas & Jhordy & Master Private Show

Flirt4Free 3 weeks ago

Ebony tgirl domina punishes her bf in the kitchen

Ebony tgirl domina punishes her bf in the kitchen

Sheshaft 2 months ago

Cute Tranny Gal Lactating her Titties after Punishing her Teats with Sex-toy, Clamps and Vacuum Milking Machine

Cute Tranny Gal Lactating her Titties after Punishing her Teats with Sex-toy, Clamps and Vacuum Milking Machine

SortPorn 2 weeks ago

MOMMY PUNISHMENT 2

MOMMY PUNISHMENT 2

aShemaleTube 3 days ago

Dominant Ts punishes her maid & fucked his bussy hard

Dominant Ts punishes her maid & fucked his bussy hard

aShemaleTube 3 weeks ago

Trans Babysitter Gets taught a lesson by HOT milf

Trans Babysitter Gets taught a lesson by HOT milf

xHamster 4 years ago

Pink Latex Shebabe Punishes Her Bf

Pink Latex Shebabe Punishes Her Bf

Eporner 3 weeks ago

Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH

Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH

xHamster 8 months ago

Pervert pigs 2

51% HD 0:39 / 11:02

FapHouse 3 years ago

Charlie Cano Private Show

61% HD 2:00 / 25:10

Charlie Cano Private Show

Flirt4Free 3 years ago

Trans hottie Sunshyne Monroe gets huge cock in her hot trans ass

69% HD 1:01 / 26:07

Trans hottie Sunshyne Monroe gets huge cock in her hot trans ass

FapHouse 5 years ago

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

The naughty TS assistant pleases her boss by banging his juicy butthole deep and hard

Tranny.one 4 years ago

Lily Demure Deepthroats

Lily Demure Deepthroats

xHamster 1 month ago

TS Larissa seduces the teacher and buggers him

TS Larissa seduces the teacher and buggers him

xHamster 1 year ago

Sissy Maid Self Bondage Electro Punishment

Sissy Maid Self Bondage Electro Punishment

xHamster 2 years ago

Futa Punishes Her Step-slut

54% 1:01 / 19:11

Futa Punishes Her Step-slut

FapHouse 3 weeks ago

Sophia Loreen Private Show

55% 4K 2:00 / 58:12

Sophia Loreen Private Show

Flirt4Free 8 months ago

Giantess Game: Tiny Man Trapped, Cuckolded Punished in My First Pussy Fucked

67% HD 1:01 / 14:05

Giantess Game: Tiny Man Trapped, Cuckolded Punished in My First Pussy Fucked

FapHouse 4 months ago

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

HD 1:01 / 16:04

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

FapHouse 2 months ago

Blonde Latex TS sub Lianna Lawson -Censored- and anal sex punishment by master Dominic Pacifico

Blonde Latex TS sub Lianna Lawson -Censored- and anal sex punishment by master Dominic Pacifico

Sheshaft 4 months ago

Shemale Domination - 15 - Isa Laurens & Rick Bitch

Shemale Domination - 15 - Isa Laurens & Rick Bitch

xHamster 1 month ago

Freaks of Nature 22 Midget two

Freaks of Nature 22 Midget two

SortPorn 3 years ago

Angel Joseph Private Show

HD 2:00 / 21:11

Angel Joseph Private Show

Flirt4Free 2 weeks ago

futa nurse pegging part 4: double Dommed, punished, facialed w/ Kendall Morr

HD 0:10 / 29:52

futa nurse pegging part 4: double Dommed, punished, facialed w/ Kendall Morr

LoyalFans 8 months ago

Pietra Mancini and friend break and use up the slave, fistin and fuckin

Pietra Mancini and friend break and use up the slave, fistin and fuckin

aShemaleTube 3 months ago

Exploring Your Giantess!

Exploring Your Giantess!

LoyalFans 1 year ago

Sabrina punishes the ass of her feMale with no mercy

Sabrina punishes the ass of her feMale with no mercy

aShemaleTube 2 years ago

Mistress and trainee use an old slave

Mistress and trainee use an old slave

Fetishpapa 3 months ago

Crazy fetish trannys! Chastity sex with a live rubber doll!

Crazy fetish trannys! Chastity sex with a live rubber doll!

xHamster 1 year ago

Jenny Wei Gets Punished #3

Jenny Wei Gets Punished #3

aShemaleTube 1 month ago

Independent Training No72 Punishment Training Chair Part 2

Independent Training No72 Punishment Training Chair Part 2

xHamster 2 months ago

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Kinky latex wearing transsexual slut fucks a kinky male toy lover

Tranny.one 4 years 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 7 months ago

Draven and The Duchess: Aspen Brooks punishes horny beefcake slave

Draven and The Duchess: Aspen Brooks punishes horny beefcake slave

Tranny.one 4 years ago

Having My My Bulge, Feet and Armpits Worshiped

54% HD 2:00 / 2:46:22

Having My My Bulge, Feet and Armpits Worshiped

Flirt4Free 2 years ago

Freaks of Nature 26 Aged Fisted and Vagina Slapping

Freaks of Nature 26 Aged Fisted and Vagina Slapping

MatureTubeHere 4 years ago

My Nipples So Hard^^

My Nipples So Hard^^

Flirt4Free 10 months ago

Busty Shemale Punishes Dude in Black Mask

Busty Shemale Punishes Dude in Black Mask

BeMyHole 1 year ago

Orianna Dunn Private Show

48% HD 2:00 / 12:27

Orianna Dunn Private Show

Flirt4Free 1 year ago

Christian & Nicco & Elvis Private Show

41% HD 2:00 / 19:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Stud gets punished by shemale mistress

Stud gets punished by shemale mistress

Fapcat 1 day ago

This Is How I Punish Myself When I Am Too Sorry

This Is How I Punish Myself When I Am Too Sorry

xHamster 6 months ago

Blonde Sissy Mitch Taylor gets punished #1 OMG that ass is so phat! 🤩🍑

Blonde Sissy Mitch Taylor gets punished #1 OMG that ass is so phat! 🤩🍑

aShemaleTube 1 month ago

Thai Mickey Gets Punished Bdsm And Bareback Domination

Thai Mickey Gets Punished Bdsm And Bareback Domination

Eporner 1 month ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

xHamster 3 months ago

Jhordy & Maxx Private Show

42% HD 2:00 / 33:20

Jhordy & Maxx Private Show

Flirt4Free 6 months ago

TS Vaniity Dominates Boy Rick Monroe Anal Fuck And Face Fucking For Intense Cum Swap

TS Vaniity Dominates Boy Rick Monroe Anal Fuck And Face Fucking For Intense Cum Swap

Sheshaft 1 month ago

Shemale Domination - 09 - Ale & Re Farias & Rick Bitch

61% 1:01 / 22:08

Shemale Domination - 09 - Ale & Re Farias & Rick Bitch

FapHouse 1 month 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

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

xHamster 1 month ago

Brunette tranny punishers take a stud prisoner and fuck him

Brunette tranny punishers take a stud prisoner and fuck him

xHamster 1 year ago

Troy Khalil Private Show

72% HD 2:00 / 18:38

Troy Khalil Private Show

Flirt4Free 2 years ago

punishment my pussy

punishment my pussy

xHamster 11 months ago

Punishing My Girlcock With a Fleshlight Until I Explode

Punishing My Girlcock With a Fleshlight Until I Explode

ShemaleSin 10 months ago

Kinky Guy Punishes TS Lorena Eduarda

Kinky Guy Punishes TS Lorena Eduarda

Eporner 4 years ago

PHAT BOOTY Sissy Slut Rips Open Fishnet Tights, TWERKS, SPANKS, FUCKS Dildo, GAPES, and CUMS

PHAT BOOTY Sissy Slut Rips Open Fishnet Tights, TWERKS, SPANKS, FUCKS Dildo, GAPES, and CUMS

xHamster 2 years ago

Hung Trans Mistresse Punishes Inactive Sissy Maid

Hung Trans Mistresse Punishes Inactive Sissy Maid

BigTitsLust 5 months ago

Trix Bell Private Show

56% 4K 2:00 / 10:54

Trix Bell Private Show

Flirt4Free 6 months ago

Angry teacher Izzy Wilde dominates and punishes her students Misbehaving Students Leana Lovings & Little Puck in a hardcore threesome

Angry teacher Izzy Wilde dominates and punishes her students Misbehaving Students Leana Lovings & Little Puck in a hardcore threesome

TrannyMovs 5 months ago

Welcome to Paradise Side of Prison

48% HD 0:39 / 6:27

Welcome to Paradise Side of Prison

FapHouse 2 months ago

PUNISHMENT

aShemaleTube 4 months ago

Viky & Master Private Show

58% HD 2:00 / 14:49

Viky & Master Private Show

Flirt4Free 5 months ago

”Elder Mabry’s Booty Atonement”

”Elder Mabry’s Booty Atonement”

TransHero 2 months ago

MOMMY PUNISHMENT 1

MOMMY PUNISHMENT 1

aShemaleTube 4 days ago

Spit a Lot of Saliva on My Shiny Boobs^^

Spit a Lot of Saliva on My Shiny Boobs^^

Flirt4Free 8 months ago

Headmaster punishes and fucks bound trans student

Headmaster punishes and fucks bound trans student

Sheshaft 1 year ago

Tommy & Master Private Show

Tommy & Master Private Show

Flirt4Free 1 day ago

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

Japanese mistress trains and punishes house slave who is excited by the Mistress's laundry by making him wear women's underwear

xHamster 4 months ago

Cross-training Cock

Cross-training Cock

Some.Porn 1 year ago

Trans Girl Worships His Cock then Fucked in her ass until she cums hard

Trans Girl Worships His Cock then Fucked in her ass until she cums hard

xHamster 4 months ago

Sophia Loreen Private Show

4K 2:00 / 29:01

Sophia Loreen Private Show

Flirt4Free 4 days ago

Young Trans Girl Milks her Big Natural Tits after being Punished

Young Trans Girl Milks her Big Natural Tits after being Punished

xHamster 5 months ago

Richii Smiith Private Show

4K 2:00 / 10:51

Richii Smiith Private Show

Flirt4Free 1 month ago

Leana Lovings and Little Puck punish their teacher Izzy Wilde in a wild threesome

Leana Lovings and Little Puck punish their teacher Izzy Wilde in a wild threesome

WeGotDicks 1 week ago

Aub Kat - Wife Punishes You

Aub Kat - Wife Punishes You

Eporner 8 months ago

Gia Darling and Her Scrub Brush

71% HD 1:01 / 36:50

Gia Darling and Her Scrub Brush

FapHouse 9 months ago

Sissy Club Slut Part 1/2: Huge Dildo Deep Throat Training & Femdom Pegging with Mistress Stellina Obscura

HD 0:10 / 21:43

Sissy Club Slut Part 1/2: Huge Dildo Deep Throat Training & Femdom Pegging with Mistress Stellina Obscura

LoyalFans 9 months ago

I was so overwhelmed that I had to take care of myself

I was so overwhelmed that I had to take care of myself

xHamster 2 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Atticus Cole loses his hole to his trans roommate Natassia Dreams

Atticus Cole loses his hole to his trans roommate Natassia Dreams

UrGayPorn 6 months ago

Sophia Loreen Private Show

49% HD 2:00 / 10:53

Sophia Loreen Private Show

Flirt4Free 3 years ago

Cami Scott Private Show

HD 2:00 / 20:51

Cami Scott Private Show

Flirt4Free 1 year ago

Tgirl slave anal punishment

Tgirl slave anal punishment

Fetishpapa 8 years ago

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

Sultry trans chick punishes the thief as she shoves her big cock balls deep in his ass

BeMyHole 5 years ago

Mean femdom Flagellation Treatment

Mean femdom Flagellation Treatment

Some.Porn 1 year ago

Charlie Cano Private Show

HD 2:00 / 27:25

Charlie Cano Private Show

Flirt4Free 3 years ago

”Shemale housewife wait all day for her hubby's cock”

”Shemale housewife wait all day for her hubby's cock”

LesbianBliss 1 month ago

Luccas & Jhordy Private Show

59% HD 2:00 / 43:43

Luccas & Jhordy Private Show

Flirt4Free 5 months ago

A Private Punishment

A Private Punishment

Tranny.one 4 years 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 4 months ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

ShemaleSin 2 months ago

Some wax and spanking before the rough bareback anal

Some wax and spanking before the rough bareback anal

Eporner 2 years 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

Aron & Master & Elvis Private Show

55% HD 2:00 / 22:53

Aron & Master & Elvis Private Show

Flirt4Free 3 years ago

Zara Clark Private Show

4K 2:00 / 15:14

Zara Clark Private Show

Flirt4Free 3 months ago

Sabrina Smiith Private Show

4K 2:00 / 14:03

Sabrina Smiith Private Show

Flirt4Free 2 months ago

Curvy Babes Cumpilation ft Natasha Nice, Jenna Starr - GirlfriendsFilms

Curvy Babes Cumpilation ft Natasha Nice, Jenna Starr - GirlfriendsFilms

Some.Porn 6 months ago

Elvis Rey & Andres & Aron Private Show

67% HD 2:00 / 23:08

Elvis Rey & Andres & Aron Private Show

Flirt4Free 2 years ago

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