Punishment Videos (61,079)

Nasty tranny cop Aylla fucks guy

Nasty tranny cop Aylla fucks guy

XHamster 1 year ago

Dominant trans chick sticks her thick Tcock in the sissy's ass deep and hard

Dominant trans chick sticks her thick Tcock in the sissy's ass deep and hard

Tranny.one 5 years ago

Extreme Beautiful Young Trans Girl Lactating and Pumping her Tits with Milking Machine

Extreme Beautiful Young Trans Girl Lactating and Pumping her Tits with Milking Machine

XHamster 5 days ago

Police Shemale Punishes Trans In Her Car - AI Generated

Premium HD 18:02

Police Shemale Punishes Trans In Her Car - AI Generated

Sheer 5 days ago

Ungrateful Goth Teen Fucked Into Line by Step-parents

HD 0:39 / 1:15:01

Ungrateful Goth Teen Fucked Into Line by Step-parents

FapHouse 2 weeks ago

Femdom inserts heel into urethra of bound submissive

Femdom inserts heel into urethra of bound submissive

Some.Porn 2 years ago

Hot Early Footage of Pornstar Holly Parker

65% HD 1:01 / 32:05

Hot Early Footage of Pornstar Holly Parker

FapHouse 2 months ago

police shemale punishes trans in her car - ai generated

police shemale punishes trans in her car - ai generated

PornBox 3 days ago

Dimitry Rolex & Liliith Private Show

50% HD 2:00 / 23:20

Dimitry Rolex & Liliith Private Show

Camster 2 years ago

Detention with Ms. Aura POV Anal Gaping

57% HD 1:01 / 22:41

Detention with Ms. Aura POV Anal Gaping

FapHouse 3 months ago

Kira's punishment part one

69% HD 0:39 / 13:06

Kira's punishment part one

FapHouse 4 years ago

Jerk off for Your Latex Mistress! Stop & Go Jerk off Instruction with Pre Cum Licking! German

52% HD 1:01 / 11:56

Jerk off for Your Latex Mistress! Stop & Go Jerk off Instruction with Pre Cum Licking! German

FapHouse 7 months ago

Sombra X Kiriko - Caught Masturbating in the Shower & Punished

Sombra X Kiriko - Caught Masturbating in the Shower & Punished

3DPornDude 6 days ago

Troy & Kiros Private Show

64% HD 2:00 / 5:11

Troy & Kiros Private Show

Flirt4Free 2 years ago

Slutty Ta Gets T&a From Dtf TS School Administrator Venus Lux!

Slutty Ta Gets T&a From Dtf TS School Administrator Venus Lux!

XHamster 1 month ago

Brutus K Models a Red Thong

70% HD 2:00 / 8:55

Brutus K Models a Red Thong

Flirt4Free 1 year ago

A Master Is Interrogating a Slave for the Truth

62% HD 0:39 / 6:32

A Master Is Interrogating a Slave for the Truth

FapHouse 2 years ago

Wild Sabrina Members-Only Show

45% HD 2:00 / 12:20

Wild Sabrina Members-Only Show

Flirt4Free 5 years ago

Bad Boy Whipping Hard by His Friend

Bad Boy Whipping Hard by His Friend

FapHouse 1 month ago

Young sissy edges and cums while riding huge dildo

Young sissy edges and cums while riding huge dildo

Tranny.one 4 years ago

Ambar & Oliver Party on May 1, 2026 - Part 2

60% HD 2:00 / 44:48

Ambar & Oliver Party on May 1, 2026 - Part 2

Camster 4 months ago

Kira's punishment part one

63% HD 1:01 / 13:06

Kira's punishment part one

FapHouse 4 years ago

Kendall Cent - Penalizes Corbin Dallas

Kendall Cent - Penalizes Corbin Dallas

TrannyGem 6 years ago

Sara & Elver Private Show

53% HD 2:00 / 6:14

Sara & Elver Private Show

Flirt4Free 9 months ago

Ryan Boness & Eduar Senni Private Show

64% HD 2:00 / 4:57

Ryan Boness & Eduar Senni Private Show

Flirt4Free 3 months ago

Real SISSY ENEMA slave cums in his own mouth

Real SISSY ENEMA slave cums in his own mouth

XHamster 1 year ago

Mission to Orgasm

Mission to Orgasm

Some.Porn 11 months ago

Annabelle Moore

Annabelle Moore

Some.Porn 1 year ago

hard pegging male in the kitchen

46% HD 0:20 / 6:48

hard pegging male in the kitchen

AnalVids 1 year ago

Employee's Dad

Some.Porn 2 years ago

Sophie Fantasy Private Show

61% HD 2:00 / 1:17:45

Sophie Fantasy Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Jul 29, 2026 - Part 2

65% 4K 2:00 / 22:38

Sophia Loreen Party on Jul 29, 2026 - Part 2

Flirt4Free 1 month ago

”Babe gang bang ravaged at public gallery”

”Babe gang bang ravaged at public gallery”

TransHero 9 months ago

Zara Clark Private Show

57% 4K 2:00 / 7:34

Zara Clark Private Show

Flirt4Free 8 months ago

This Dildo Got What It Deserved

71% 0:39 / 4:05

This Dildo Got What It Deserved

FapHouse 8 months ago

Lika Kai Party on Jul 16, 2026 - Part 2

56% 4K 2:00 / 15:57

Lika Kai Party on Jul 16, 2026 - Part 2

Camster 2 months ago

Fuck me in an office uniform, I'm your boss.

Fuck me in an office uniform, I'm your boss.

XHamster 1 year ago

Anal Punishment with Melany Furie

HD 1:01 / 23:36

Anal Punishment with Melany Furie

FapHouse 4 days ago

Hung Dominant Mistress Shemale Fucks bog ass toy boy in the kitchen and punish him

Hung Dominant Mistress Shemale Fucks bog ass toy boy in the kitchen and punish him

AShemaleTube 1 month ago

Sophia Loreen Private Show

56% 4K 2:00 / 8:29

Sophia Loreen Private Show

Camster 1 week ago

Muscled leather hunk at the mercy of Mr. Ducati

Premium 68% HD 53:51

Muscled leather hunk at the mercy of Mr. Ducati

KinkMen 11 years ago

Latex Slave Fucked by Cock & Machine

68% HD 0:39 / 19:21

Latex Slave Fucked by Cock & Machine

FapHouse 8 months ago

Put Your Tongue into My Foreskin

67% HD 2:00 / 5:07

Put Your Tongue into My Foreskin

Flirt4Free 2 years ago

Watch as Sissy Gimp gets disciplined for smoking instead of vaping and gets punished with a tranny spanking

Watch as Sissy Gimp gets disciplined for smoking instead of vaping and gets punished with a tranny spanking

TrannyMovs 6 months 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 2 years ago

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

52% HD 0:39 / 28:08

Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial

FapHouse 6 months ago

Buttfucking The School Bully

Buttfucking The School Bully

Some.Porn 1 month ago

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

Submissive a.i. - Sexy Ryder Monroe Is Punished by Cynical Scientist

XHamster 1 year ago

A Dominant Granny Trains These Little Whores

A Dominant Granny Trains These Little Whores

XHamster 10 months ago

Troy Khalil Private Show

74% 4K 2:00 / 9:29

Troy Khalil Private Show

Flirt4Free 9 months ago

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

GetTranny 9 months ago

Sophia Loreen Private Show

65% 4K 2:00 / 10:47

Sophia Loreen Private Show

Camster 2 months ago

Playtime for Mister K

54% HD 2:00 / 23:54

Playtime for Mister K

Flirt4Free 11 years ago

Jhordy & Maxx Private Show

48% HD 2:00 / 1:21:10

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Slave rental

XHamster 1 year ago

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

”Atticus Cole loses his hole to his transgender roomie Natassia Dreams”

Trashreality 1 year ago

Sophia Loreen Private Show

4K 2:00 / 10:50

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Sophia Loreen Party on Sep 7, 2026 - Part 3

57% 4K 2:00 / 4:07

Sophia Loreen Party on Sep 7, 2026 - Part 3

Camster 2 weeks ago

I Fucked My New Toy, and I Left All My Cum Inside It

60% HD 2:00 / 4:00

I Fucked My New Toy, and I Left All My Cum Inside It

Flirt4Free 3 years ago

Sophia Loreen Private Show

57% HD 2:00 / 10:44

Sophia Loreen Private Show

Flirt4Free 2 years ago

TS Dominatrix Jesse Fucks and Punishes a Submissive Man and a TS Man!

63% HD 0:39 / 48:17

TS Dominatrix Jesse Fucks and Punishes a Submissive Man and a TS Man!

FapHouse 1 month ago

Sophie Fantasy Private Show

62% HD 2:00 / 36:14

Sophie Fantasy Private Show

Flirt4Free 1 month ago

I'll Punish You so Well, You'll Be Crawling Back for More, Begging Like the Needy Little Whore You Are

I'll Punish You so Well, You'll Be Crawling Back for More, Begging Like the Needy Little Whore You Are

XHamster 1 month ago

Elias & Elix Private Show

52% HD 2:00 / 37:58

Elias & Elix Private Show

Flirt4Free 1 year ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 9 years ago

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

Shemale Domination - 04 - Vitoria Neves & Rick Bitch

XHamster 8 months ago

Dazzling Rose Private Show

57% 4K 2:00 / 6:50

Dazzling Rose Private Show

Flirt4Free 1 month ago

Hawt femdom shemale on bike ride! Ballbusting and CBT for slutty camery man!

Hawt femdom shemale on bike ride! Ballbusting and CBT for slutty camery man!

Amateur8 1 week ago

Skinny dude buttfucked by stranger

Skinny dude buttfucked by stranger

Some.Porn 1 year ago

DOMINATE'S GRIP CHOKES CONTROL IN SHADOWED CHAINS

DOMINATE'S GRIP CHOKES CONTROL IN SHADOWED CHAINS

XHamster 5 months ago

Sophia Loreen Party on May 28, 2026 - Part 3

59% HD 2:00 / 49:53

Sophia Loreen Party on May 28, 2026 - Part 3

Flirt4Free 3 months ago

Your Favorite Distraction

Your Favorite Distraction

Camster 3 months ago

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

Nasty thief gets punished for robbing by getting his ass stretched wide by the hot trans chick's huge Tcock

BeMyHole 6 years ago

Elvis & Alfonso & Master Private Show

63% HD 2:00 / 10:47

Elvis & Alfonso & Master Private Show

Flirt4Free 4 years ago

Jacob Malik Private Show

63% HD 2:00 / 15:29

Jacob Malik Private Show

Flirt4Free 7 months ago

Sophia Loreen Private Show

66% 4K 2:00 / 41:26

Sophia Loreen Private Show

Flirt4Free 1 month ago

Hanna Ven Private Show

57% HD 2:00 / 2:17:23

Hanna Ven Private Show

Flirt4Free 2 years ago

Flexing and Dirty Talking About My Biceps

69% HD 2:00 / 4:19

Flexing and Dirty Talking About My Biceps

Flirt4Free 8 months ago

Double Dommed in the Dungeon, a Trans Femdom BDSM Threesome

65% HD 0:10 / 27:36

Double Dommed in the Dungeon, a Trans Femdom BDSM Threesome

LoyalFans 1 year ago

Sophia Loreen Private Show

58% HD 2:00 / 37:35

Sophia Loreen Private Show

Flirt4Free 5 months 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

PostOp Ladyboy Nid Self Punishment

PostOp Ladyboy Nid Self Punishment

Tranny.one 7 years ago

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting Full-length (1080p)

66% HD 1:01 / 59:00

Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting Full-length (1080p)

FapHouse 2 weeks ago

Transvestite from hell

Transvestite from hell

XHamster 1 year ago

Sexy Jade Trolling for Poling

HD 0:39 / 44:42

Sexy Jade Trolling for Poling

FapHouse 1 year ago

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

Fantasy Solo Hot Girl Next Door Amatuer T Girl!

XHamster 3 months ago

Futa Fellate Sissy Ass fucking - Amirah Adara & Austin Ponce

Futa Fellate Sissy Ass fucking - Amirah Adara & Austin Ponce

4Gay 3 weeks ago

Sophia Loreen Party on Jul 25, 2026 - Part 3

67% HD 2:00 / 41:09

Sophia Loreen Party on Jul 25, 2026 - Part 3

Camster 1 month ago

How a Tgirl severely punishs her big cock. Clip 1

How a Tgirl severely punishs her big cock. Clip 1

XHamster 11 months ago

Interracial Tease & Ballbusting For Trans Woman Julia Masakova | MahoganyQen

58% HD 0:10 / 14:58

Interracial Tease & Ballbusting For Trans Woman Julia Masakova | MahoganyQen

LoyalFans 2 months ago

Tomb Raider Futa Butt sex - Melody Marks & Nicolas Novoa

Tomb Raider Futa Butt sex - Melody Marks & Nicolas Novoa

4Gay 2 weeks ago

Step Stepmommy Has a Cock Bratty New Stepdaughter Finds Out the Hard Way

HD 1:01 / 48:35

Step Stepmommy Has a Cock Bratty New Stepdaughter Finds Out the Hard Way

FapHouse 3 days ago

Bad Naomi anally punished near 35cm vibrator. Creamfill, tied underneath, belly expansion(out Naomi 5 scene)

Bad Naomi anally punished near 35cm vibrator. Creamfill, tied underneath, belly expansion(out Naomi 5 scene)

KAMS 1 year ago

submissive asian ladyboy anal casting & slave training

submissive asian ladyboy anal casting & slave training

PornBox 1 month ago

Beautiful Blonde Asian Trans Girl Sunbathing Ends up in My Room Getting Fucked

HD 1:01 / 38:05

Beautiful Blonde Asian Trans Girl Sunbathing Ends up in My Room Getting Fucked

FapHouse 4 months ago

Pink lingeried black shemale punishes her bf

Pink lingeried black shemale punishes her bf

AShemaleTube 6 months ago

From massage to hard sex

From massage to hard sex

Some.Porn 1 year ago

Huge BBC Takes Ria Bentley to Poundtown with Creampie

Huge BBC Takes Ria Bentley to Poundtown with Creampie

XHamster 2 years ago

Jacob Malik Private Show

58% HD 2:00 / 8:00

Jacob Malik Private Show

Flirt4Free 10 months ago

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

69% HD 1:01 / 14:56

Petite Emo White Trans Girl with Big Puffy Nipples Sucks and Milks Them with a Vacuum Pump

FapHouse 10 months ago

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

Kayleigh Coxx Punishes Peeping Motel Manager Lauren Phillips

XHamster 8 months ago

Boy Ties His Friend to Punish Him on the Roof

Boy Ties His Friend to Punish Him on the Roof

XHamster 2 years ago

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

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

XHamster 9 months ago

Izzy Punishing her Asshole

Izzy Punishing her Asshole

AShemaleTube 3 weeks ago

Charlie Cano Private Show

67% HD 2:00 / 6:23

Charlie Cano Private Show

Flirt4Free 3 years 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 2 years ago

Sophia Loreen Private Show

59% HD 2:00 / 15:34

Sophia Loreen Private Show

Camster 2 months ago

Jacob Malik Party on Aug 18, 2024

65% HD 2:00 / 1:10:04

Jacob Malik Party on Aug 18, 2024

Flirt4Free 2 years ago

Tatiana & Lord Private Show

55% HD 2:00 / 9:23

Tatiana & Lord Private Show

Camster 2 months ago

Lisan & Mine Private Show

4K 2:00 / 23:47

Lisan & Mine Private Show

Flirt4Free 3 weeks ago

TGirl Ria Bentley Gets Her Ass Punished By Car Repair Guy

77% HD 0:22 / 15:49

TGirl Ria Bentley Gets Her Ass Punished By Car Repair Guy

Clips4sale 2 years ago

Cheap Slut Part 2 - Sex Slave Training

Cheap Slut Part 2 - Sex Slave Training

XHamster 1 year ago

Stuard & Jhordy & Ronaldo Private Show

57% HD 2:00 / 6:10

Stuard & Jhordy & Ronaldo Private Show

Flirt4Free 2 years ago

Liam Jacobson Private Show

62% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 10 months ago

Brutus Wear Leather Jacket and Leather Gloves and Jerks

55% HD 2:00 / 9:29

Brutus Wear Leather Jacket and Leather Gloves and Jerks

Flirt4Free 7 years ago

Asian Dommes Training White Sissy Slave Kassie

65% 0:39 / 12:34

Asian Dommes Training White Sissy Slave Kassie

FapHouse 1 week ago

Patric & Alexander & Lian Private Show

46% HD 2:00 / 38:16

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Aubrey Saint Private Show

HD 2:00 / 15:48

Aubrey Saint Private Show

Camster 1 week ago

Liam Jacobson Private Show

71% HD 2:00 / 8:02

Liam Jacobson Private Show

Flirt4Free 1 year ago

TS Seduction: Steven Sweat and Danielle Foxxx

55% HD 0:30 / 44:00

TS Seduction: Steven Sweat and Danielle Foxxx

AEBN 9 years ago

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