Punishment Videos (59,633)

TS Mistress Fucks Her Bound Male Slave

TS Mistress Fucks Her Bound Male Slave

Xozilla 2 months ago

Tall redhead shemale punishing a dude's asshole

Tall redhead shemale punishing a dude's asshole

AShemaleTube 5 months ago

Throat Fucked & Ass Gaped: TS Grey Perrier’s Painful Anal Redemption

66% HD 0:10 / 42:03

Throat Fucked & Ass Gaped: TS Grey Perrier’s Painful Anal Redemption

LoyalFans 2 months ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

XHamster 6 months ago

Ryan Boness & Eduar Senni Private Show

62% HD 2:00 / 4:57

Ryan Boness & Eduar Senni Private Show

Flirt4Free 1 month ago

Rough anal treatment for Tranny Sabina

Rough anal treatment for Tranny Sabina

Tranny.one 4 years ago

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

Mistress Baton's Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

XHamster 6 months ago

TS Nicole Montero fucking the TS Pornstar Laisa Lins after the well deserved Punishment

TS Nicole Montero fucking the TS Pornstar Laisa Lins after the well deserved Punishment

FapHouse 3 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

Stepdad pounds his stepdaughter's tight pussy while wearing braces - Scarlet Skies

Stepdad pounds his stepdaughter's tight pussy while wearing braces - Scarlet Skies

Some.Porn 2 years ago

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

Sluts Get Fucked: New Girl Ella Hollywood Fucked by Sebastian Keys

XHamster 2 months ago

Ponytailed Ladyboy Slave For Cock

Ponytailed Ladyboy Slave For Cock

Eporner 3 years ago

Submissive Slave Dominated By Ts Dommes [Full Movie]

Submissive Slave Dominated By Ts Dommes [Full Movie]

XHamster 1 year ago

Feelipe & Adara Private Show

65% HD 2:00 / 6:26

Feelipe & Adara Private Show

Flirt4Free 10 months ago

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now 😈

Avery Angel gets deep strokes and fucked by The BBC PUNISHER! Full video available now 😈

AShemaleTube 1 year ago

Hot Early Footage of Pornstar Holly Parker

HD 0:39 / 32:05

Hot Early Footage of Pornstar Holly Parker

FapHouse 2 weeks ago

Thick ebony shemale punishes a dude hard

Thick ebony shemale punishes a dude hard

TrannyGem 3 years ago

Mistress and Her maid

63% HD 0:10 / 6:52

Mistress and Her maid

LoyalFans 1 year ago

Sophia Loreen Private Show

66% HD 2:00 / 35:48

Sophia Loreen Private Show

Camster 1 month ago

Femdom Ts Pool Party Fuck Fest wmv

51% HD 0:11 / 26:16

Femdom Ts Pool Party Fuck Fest wmv

Clips4sale 4 years 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 3 days ago

Sophia Loreen Private Show

HD 2:00 / 12:23

Sophia Loreen Private Show

Camster 1 month ago

Punishing the Cupcake Thief - A trans anal threesome scene

Premium HD 25:14

Punishing the Cupcake Thief - A trans anal threesome scene

XVideosRed 3 years ago

Christian & Lian Private Show

54% HD 2:00 / 5:42

Christian & Lian Private Show

Flirt4Free 3 years ago

Sissy Dee should be cleaning, but she gets carried away playing

Sissy Dee should be cleaning, but she gets carried away playing

XHamster 2 months ago

Jennifer Skanes Private Show

50% HD 2:00 / 19:49

Jennifer Skanes Private Show

Camster 1 month ago

Black tranny domina punishes a guy's anus hard

Black tranny domina punishes a guy's anus hard

AShemaleTube 10 months ago

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

DIAPER and PISS ENEMA treatment for SISSY husband in CHASTITY

XHamster 2 years ago

Sophia Loreen Private Show

HD 2:00 / 38:25

Sophia Loreen Private Show

Camster 1 month ago

Carla Novais and Lukas Leal

Carla Novais and Lukas Leal

XHamster 1 year ago

Domina shemale damages spiderman's ass

Domina shemale damages spiderman's ass

Eporner 5 months 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 1 week ago

Enjoying pounding my jiggly butt with a dildo

Enjoying pounding my jiggly butt with a dildo

XHamster 4 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

Sara Salazar And Cherry Mavrik In Goddess Cherry Punishes My Slutty Holes

Sara Salazar And Cherry Mavrik In Goddess Cherry Punishes My Slutty Holes

Xshemale 1 month ago

Milas Carteros Private Show

HD 2:00 / 13:28

Milas Carteros Private Show

Camster 2 days ago

Big Tits Crossdresser Jerking and Cumming Her Big Cock After Wedgie

HD 1:01 / 20:15

Big Tits Crossdresser Jerking and Cumming Her Big Cock After Wedgie

FapHouse 2 weeks ago

Hot trans Aubrey Kate punishes Jordan Lake with deep hard fucking

Hot trans Aubrey Kate punishes Jordan Lake with deep hard fucking

MenGem 4 weeks 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

TS Seduction 4: Rubber Room Rituals

HD 0:30 / 2:46:00

TS Seduction 4: Rubber Room Rituals

AEBN 7 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

strict mistress with huge strapon and big cock catch and punish her robber

strict mistress with huge strapon and big cock catch and punish her robber

AShemaleTube 1 year ago

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

Sexy Teacher Dea Satin Orders You to Suck Her Strap-on Dildo Deep and Long

XHamster 5 months ago

Exotic stepdaughter sucks huge dick and ends up cr

Exotic stepdaughter sucks huge dick and ends up cr

ALOTPorn 1 year ago

Verticalargument4

57% HD 0:39 / 1:28

Verticalargument4

FapHouse 2 months ago

Nasty tranny cop Aylla fucks guy

Nasty tranny cop Aylla fucks guy

XHamster 1 year ago

Lika Kai Private Show

4K 2:00 / 10:07

Lika Kai Private Show

Camster 1 day ago

TRANSFIXED - Two Naughty Students In Detention Get Punished Well By Her Hot Trans Teacher TS Foxxy

TRANSFIXED - Two Naughty Students In Detention Get Punished Well By Her Hot Trans Teacher TS Foxxy

Eporner 7 months ago

Three kinky mistresses punish their submissive with a hard spanking in their high heels

Three kinky mistresses punish their submissive with a hard spanking in their high heels

Some.Porn 2 years ago

Jumping Babes

Some.Porn 10 months ago

Sandy Nell Private Show

64% 4K 2:00 / 11:20

Sandy Nell Private Show

Camster 2 weeks ago

You Won't Cum if You're Not GAY

66% 4K 0:30 / 15:16

You Won't Cum if You're Not GAY

Clips4sale 5 months 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

Busty trans Daisty Taylor gets dominated

Busty trans Daisty Taylor gets dominated

PornDR 3 years ago

Shemale Asuka Extreme Tits Vacuum Pump Lactation and Nipple Punishment with Heels

HD 1:01 / 19:19

Shemale Asuka Extreme Tits Vacuum Pump Lactation and Nipple Punishment with Heels

FapHouse 6 days ago

Shemale bdsm dungeon dominatrix

Shemale bdsm dungeon dominatrix

XHamster 11 months ago

Balls crushed & Cock electric torture

Balls crushed & Cock electric torture

XHamster 3 years ago

Punish Babe 3D Hardcore Doggystyle Milf

Punish Babe 3D Hardcore Doggystyle Milf

Tranny.one 6 years ago

Out Foxed, Flogged, and Fucked

58% HD 0:39 / 34:05

Out Foxed, Flogged, and Fucked

FapHouse 2 months ago

This Ass

FapHouse 5 months ago

Sophia Loreen Party on Jul 29, 2026 - Part 2

4K 2:00 / 22:38

Sophia Loreen Party on Jul 29, 2026 - Part 2

Camster 6 days ago

Tranny Dom Cam Session! Loser cums quickly fucking a rubber doll!

Tranny Dom Cam Session! Loser cums quickly fucking a rubber doll!

XHamster 1 year ago

The Mistress Urinates Into the Cross-dressing Slave's Mouth

HD 0:39 / 15:00

The Mistress Urinates Into the Cross-dressing Slave's Mouth

FapHouse 3 months ago

Shemales in leather boots tie up a man before fucking him in

Shemales in leather boots tie up a man before fucking him in

XHamster 1 year ago

Sorority Sitters Part 3 - Khloe Kay, Drake Von

Sorority Sitters Part 3 - Khloe Kay, Drake Von

Eporner 1 year ago

Sophia Loreen Private Show - Part 2

HD 2:00 / 40:15

Sophia Loreen Private Show - Part 2

Camster 2 weeks ago

Mary & Polly Private Show

HD 2:00 / 21:35

Mary & Polly Private Show

Camster 1 year ago

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

58% HD 0:39 / 11:00

Trans JOI Punishing You with My Real Cock! I've Had a Couple People Request a Trans JOI! so Here It Is

FapHouse 8 months ago

Employee's Dad

Some.Porn 2 years ago

femdom shemale boss punishes employee with rough sex 🔥 (ai generated)

46% HD 0:15 / 5:13

femdom shemale boss punishes employee with rough sex 🔥 (ai generated)

PornBox 2 weeks ago

Punished for Creating a Havoc Inside the Food Store

Punished for Creating a Havoc Inside the Food Store

3DPornDude 1 month ago

Jade’s BDSM Play

Jade’s BDSM Play

ALOTPorn 2 days ago

Aubrey Kate Dominates Pierce Paris

Aubrey Kate Dominates Pierce Paris

Tranny.one 5 months ago

Humiliated

XHamster 2 years ago

Teacher Anally Punishes A Bad student 18+

Teacher Anally Punishes A Bad student 18+

AniPorn 2 years ago

Bossy Dillon Stone punishes lazy FTM Joey Michaels with her thick pussy

Bossy Dillon Stone punishes lazy FTM Joey Michaels with her thick pussy

UrGayPorn 9 months ago

Sophia Loreen Private Show

HD 2:00 / 25:41

Sophia Loreen Private Show

Camster 4 weeks ago

Sophia Loreen Private Show

63% HD 2:00 / 18:12

Sophia Loreen Private Show

Camster 1 month ago

Tranny maid River Enza disciplined for being naughty

Tranny maid River Enza disciplined for being naughty

UrGayPorn 1 year ago

Venezuelan mate with great trouser snake of 23cm licking chicken butt Bogota

Venezuelan mate with great trouser snake of 23cm licking chicken butt Bogota

MenGem 4 weeks ago

Princes Ammy punishes naughty crossdresser with a hard handjob and ass pounding

Princes Ammy punishes naughty crossdresser with a hard handjob and ass pounding

GayX 3 days ago

Aubrey Saint Private Show

Aubrey Saint Private Show

Camster 2 weeks ago

NIkki Montero punishing Laisa Lins

NIkki Montero punishing Laisa Lins

FapHouse 6 years 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 5 months ago

Wild shemale need punishment

Wild shemale need punishment

XHamster 3 years ago

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

HD 1:01 / 21:15

Dominated - Getting Punched by the Trans Boy and Sucking Pussy

FapHouse 1 month ago

Cock Prisoner Aroma Obsession

Cock Prisoner Aroma Obsession

XHamster 2 weeks ago

Sophia Loreen Private Show

HD 2:00 / 23:59

Sophia Loreen Private Show

Camster 1 week ago

Instruction from the trainer No 12 Exposure walk in the sports park

Instruction from the trainer No 12 Exposure walk in the sports park

XHamster 8 months ago

Roommate Issues

Roommate Issues

Some.Porn 2 years ago

Viky & Master Private Show

58% HD 2:00 / 25:32

Viky & Master Private Show

Flirt4Free 11 months ago

Mistress Makes House Slave Cross-dress, Orders Him to Fap, Watches Him Jerk off His Dick, and Cum Denial with Handjob

Mistress Makes House Slave Cross-dress, Orders Him to Fap, Watches Him Jerk off His Dick, and Cum Denial with Handjob

XHamster 8 months 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

Troy Khalil Private Show

64% HD 2:00 / 5:47

Troy Khalil Private Show

Flirt4Free 2 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

Mike Swift & David Golden Private Show

63% HD 2:00 / 5:45

Mike Swift & David Golden Private Show

Flirt4Free 6 days ago

Sophia Loreen Party on Jul 25, 2026 - Part 3

61% HD 2:00 / 41:09

Sophia Loreen Party on Jul 25, 2026 - Part 3

Flirt4Free 1 week 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

Dare to Get a Little Closer.

Dare to Get a Little Closer.

Flirt4Free 2 weeks ago

Viky & Master Private Show

58% HD 2:00 / 14:39

Viky & Master Private Show

Flirt4Free 11 months ago

Femdom Shemale Gangbang Action by TSDomme.com

Femdom Shemale Gangbang Action by TSDomme.com

XHamster 1 year ago

Master & Christian Mckenzie & Christian Rey Private Show

54% HD 2:00 / 39:40

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Shemale Mafia Punish Poor Girl

Shemale Mafia Punish Poor Girl

Nuvid 1 week ago

”Blindfolded strapped & public banged”

”Blindfolded strapped & public banged”

TransHero 7 months ago

Hot Bhabhi Playing with Her Toy. Faphouse XXX

Hot Bhabhi Playing with Her Toy. Faphouse XXX

FapHouse 2 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

The League of Extraordinary Transsexuals: The Final Punishment

The League of Extraordinary Transsexuals: The Final Punishment

AbTranny 10 years ago

Top 10 Femdom Ideas 2022

Top 10 Femdom Ideas 2022

XHamster 2 years 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

Vibrator Ruining in Nylon Catsuit

70% HD 0:10 / 14:52

Vibrator Ruining in Nylon Catsuit

Clips4sale 4 years ago

Puffy Nipples Trans Samus Pumping and Lactatingg her Tits with Vacuum Milking Machine until they Grow (Breast Expansion)

Puffy Nipples Trans Samus Pumping and Lactatingg her Tits with Vacuum Milking Machine until they Grow (Breast Expansion)

XHamster 6 days 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

$Christian\'s Turn to Eject His Cum into Master\'s Mouth$ 61% HD 2:00 / 9:58

Christian\'s Turn to Eject His Cum into Master\'s Mouth

Flirt4Free 3 years ago

1080P Trans slut really curvy likes boys with tight asses

HD 0:25 / 14:24

1080P Trans slut really curvy likes boys with tight asses

Clips4sale 2 years ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 11 months ago

Alaia & Elver Private Show

61% HD 2:00 / 6:13

Alaia & Elver Private Show

Camster 2 years ago

Tranny nun punishing anal male prisoner

Tranny nun punishing anal male prisoner

AShemaleTube 7 years ago

Sexy Ana Foxxx dominates thick sub Katie St. Ives

Sexy Ana Foxxx dominates thick sub Katie St. Ives

Some.Porn 7 months ago

Hang Ups & Hook Ups: Kayleigh Coxx Calls up Mason Lear

Hang Ups & Hook Ups: Kayleigh Coxx Calls up Mason Lear

XHamster 7 months ago

Hard Cash Payback!

Hard Cash Payback!

XHamster 1 year ago

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