Punishment Videos (35,206)

Hercules & Lance & Lian Miller Private Show

58% HD 2:00 / 8:05

Hercules & Lance & Lian Miller Private Show

Flirt4Free 3 years ago

Cock Prisoner Aroma Obsession

HD 0:39 / 14:28

Cock Prisoner Aroma Obsession

FapHouse 2 months ago

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

63% HD 1:01 / 32:22

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

FapHouse 1 year ago

Patric & Alexander & Lian Private Show

47% HD 2:00 / 38:16

Patric & Alexander & Lian Private Show

Flirt4Free 3 years ago

Trans Ria Bentley Gets Peg Punished By Dana Delvey

80% 0:30 / 21:27

Trans Ria Bentley Gets Peg Punished By Dana Delvey

Clips4sale 1 year ago

Marian & Richard Private Show

57% HD 2:00 / 1:56:58

Marian & Richard Private Show

Flirt4Free 3 months ago

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

Premium 56% HD 33:02

Cherry and I Dominate Our Disobedient Puppies Nyxi and Livi

XVideosRed 2 years ago

Jacob Malik Private Show

63% HD 2:00 / 15:29

Jacob Malik Private Show

Flirt4Free 7 months ago

Jennifer Venturi Private Show

Jennifer Venturi Private Show

Flirt4Free 1 week ago

Tovez Private Show

66% HD 2:00 / 36:59

Tovez Private Show

Flirt4Free 2 years ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 1 year ago

Charlie Cano Private Show

HD 2:00 / 11:36

Charlie Cano Private Show

Flirt4Free 3 years ago

Mistress Has Found a Way to Stop Sissy From Playing

Mistress Has Found a Way to Stop Sissy From Playing

FapHouse 1 month ago

Big Tits Femboy Ben Tennyson Lactating and Pumping Her Puffy Nipples with Vacuum Milking Machine

67% HD 0:39 / 19:40

Big Tits Femboy Ben Tennyson Lactating and Pumping Her Puffy Nipples with Vacuum Milking Machine

FapHouse 3 months ago

Feelipe & Adara Private Show

68% HD 2:00 / 13:21

Feelipe & Adara Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

HD 2:00 / 14:02

Sophia Loreen Private Show

Flirt4Free 5 months ago

Valentin & Harris Private Show

Valentin & Harris Private Show

Flirt4Free 4 years ago

Kaled & Lian Private Show

57% HD 2:00 / 11:41

Kaled & Lian Private Show

Flirt4Free 3 years ago

Cuckold Therapy - Sarina Havok, Robin Coffins and Cherry Mavrik

Premium HD 21:05

Cuckold Therapy - Sarina Havok, Robin Coffins and Cherry Mavrik

Sheer 4 years ago

Corrine Dittmann Private Show

Corrine Dittmann Private Show

Flirt4Free 4 months ago

Alejandro & Bayron & Angel & Johan Private Show

Alejandro & Bayron & Angel & Johan Private Show

Flirt4Free 2 years ago

HIGH HEELS VIBRATOR BONDAGE PUNISHMENT RETURNS - SHAKING & TREMBLING RUBBERSLAVE MILKED WITH NO SAFEWORD

HIGH HEELS VIBRATOR BONDAGE PUNISHMENT RETURNS - SHAKING & TREMBLING RUBBERSLAVE MILKED WITH NO SAFEWORD

Clips4sale 9 months ago

Mike Swift & David Golden Private Show

60% HD 2:00 / 8:59

Mike Swift & David Golden Private Show

Flirt4Free 1 month ago

The League of Extraordinary Transsexuals: Part 1 Super Hero Feature

HD 1:01 / 49:47

The League of Extraordinary Transsexuals: Part 1 Super Hero Feature

FapHouse 4 weeks ago

Patric & Oliver Private Show

69% HD 2:00 / 8:26

Patric & Oliver Private Show

Flirt4Free 4 years ago

Nelly Gale Private Show

4K 2:00 / 20:02

Nelly Gale Private Show

Flirt4Free 2 days ago

Domination - Pop Per Instructions and Verbal

55% HD 2:00 / 7:30

Domination - Pop Per Instructions and Verbal

Flirt4Free 2 years ago

step-mommy punishes gamer girl nyxi

HD 0:30 / 11:47

step-mommy punishes gamer girl nyxi

AnalVids 4 months ago

Petite Alt Girl Gets Ragdolled Sweet & Rough by Dominant Tgirl and Takes Her Load

65% 0:39 / 31:44

Petite Alt Girl Gets Ragdolled Sweet & Rough by Dominant Tgirl and Takes Her Load

FapHouse 3 months ago

Luccas & Jhordy Private Show

63% HD 2:00 / 7:43

Luccas & Jhordy Private Show

Flirt4Free 1 year ago

Livid Doll Gives stepMommy a Blowjob : hot trans deepthroat facefuck action with hungbig dick girlcock for little

HD 0:14 / 22:26

Livid Doll Gives stepMommy a Blowjob : hot trans deepthroat facefuck action with hungbig dick girlcock for little

Clips4sale 1 year ago

Desire Sweet Private Show

HD 2:00 / 33:58

Desire Sweet Private Show

Flirt4Free 18 hours ago

Marcelo & Angel & Ivan Private Show

Marcelo & Angel & Ivan Private Show

Flirt4Free 2 years ago

Colombian Boys Private Show

60% 4K 2:00 / 5:27

Colombian Boys Private Show

Flirt4Free 4 months ago

Willy Veins Private Show

61% HD 2:00 / 7:35

Willy Veins Private Show

Flirt4Free 1 year ago

Jewel Selfsucker Private Show

57% HD 2:00 / 4:48

Jewel Selfsucker Private Show

Flirt4Free 11 months ago

Extreme Blowjob with Tape Tied Hands and Legs

54% HD 0:39 / 10:37

Extreme Blowjob with Tape Tied Hands and Legs

FapHouse 1 year ago

Jennifer Venturi Private Show

4K 2:00 / 16:06

Jennifer Venturi Private Show

Flirt4Free 1 day ago

Sommer Kitty Private Show

HD 2:00 / 13:11

Sommer Kitty Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

62% 4K 2:00 / 15:20

Sophia Loreen Private Show

Flirt4Free 1 month ago

Shocking Confession to the Wedding Priest!

53% HD 1:01 / 9:27

Shocking Confession to the Wedding Priest!

FapHouse 2 years 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

Shemale Slut Carla Fucking Her Ass with a Big Dildo

62% HD 0:39 / 4:18

Shemale Slut Carla Fucking Her Ass with a Big Dildo

FapHouse 5 months ago

naked full dance

55% HD 2:00 / 4:52

naked full dance

Flirt4Free 3 years ago

Rock Star

66% HD 2:00 / 4:25

Flirt4Free 6 years ago

Troy Khalil Private Show

59% HD 2:00 / 6:28

Troy Khalil Private Show

Flirt4Free 2 years ago

Tatiana & Lord Private Show

66% HD 2:00 / 8:23

Tatiana & Lord Private Show

Flirt4Free 2 months ago

4 cocks pegging gangbang to punish naughty students

66% HD 0:10 / 13:00

4 cocks pegging gangbang to punish naughty students

LoyalFans 1 year ago

A Disgrace to Our Town Part 1

54% 1:01 / 21:04

A Disgrace to Our Town Part 1

FapHouse 1 year ago

Trans Angels - Couple Catches Natalie Mars Masturbating, Then Lance Hart & Veronica Avluv Join in

HD 1:01 / 29:34

Trans Angels - Couple Catches Natalie Mars Masturbating, Then Lance Hart & Veronica Avluv Join in

FapHouse 6 days ago

Master & Ithan Private Show

62% HD 2:00 / 44:15

Master & Ithan Private Show

Flirt4Free 1 year 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 weeks ago

Sara & Elver Private Show

62% HD 2:00 / 14:48

Sara & Elver Private Show

Flirt4Free 10 months ago

Jhon & Derek & Chris Private Show

68% HD 2:00 / 19:26

Jhon & Derek & Chris Private Show

Flirt4Free 4 years ago

Asian Trans Beauty Billie Beaumont Punishes Petite Trans Cutie in Nurse Outfit

Premium HD 15:21

Asian Trans Beauty Billie Beaumont Punishes Petite Trans Cutie in Nurse Outfit

XVideosRed 11 months ago

Sophie Fantasy Private Show

59% HD 2:00 / 4:53

Sophie Fantasy Private Show

Flirt4Free 5 months ago

this town ain't big enough for the two of us: futa sheriff gives criminal rough punishment pegging - SD wmv

this town ain't big enough for the two of us: futa sheriff gives criminal rough punishment pegging - SD wmv

Clips4sale 9 months ago

Jennifer Venturi Private Show

Jennifer Venturi Private Show

Flirt4Free 2 weeks ago

You Sit Between My Big Legs, Because You Love the View

HD 2:00 / 36:03

You Sit Between My Big Legs, Because You Love the View

Flirt4Free 3 years ago

Stepmom use strapon for punishing

Premium HD 4:13

Stepmom use strapon for punishing

XVideosRed 2 months ago

Charlie Cano Private Show

59% HD 2:00 / 13:13

Charlie Cano Private Show

Flirt4Free 3 years ago

Jhordy & Maxx Private Show

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

Jhordy & Maxx Private Show

Flirt4Free 1 year ago

Riley Wears Cummy Pee Stained Panties

55% 0:11 / 18:05

Riley Wears Cummy Pee Stained Panties

Clips4sale 3 years ago

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

62% HD 0:39 / 48:17

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

FapHouse 1 month ago

My Shemale Fantasy Ends in a Cumshot as She Pegs My Asshole

My Shemale Fantasy Ends in a Cumshot as She Pegs My Asshole

FapHouse 3 months ago

Lena Pauline Private Show

Lena Pauline Private Show

Flirt4Free 3 years ago

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

Punished Slaves BDSM Bondage Gay Amador Big Dick - 1

FapHouse 6 months ago

Axxle Harris Private Show

HD 2:00 / 19:45

Axxle Harris Private Show

Flirt4Free 4 years ago

PUNISHED IN PLACE #1 featuring Erin Everheart

Premium HD 21:31

PUNISHED IN PLACE #1 featuring Erin Everheart

XVideosRed 2 years ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 1 week ago

Charlie Cano Private Show

65% HD 2:00 / 9:57

Charlie Cano Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Jun 19, 2026 - Part 3

60% HD 2:00 / 47:03

Sophia Loreen Party on Jun 19, 2026 - Part 3

Flirt4Free 3 months ago

Wild Sabrina Private Show

65% HD 2:00 / 5:12

Wild Sabrina Private Show

Flirt4Free 3 years ago

Anal Sluts: Audrey Rose and Lea Lexis

HD 0:39 / 1:24:48

Anal Sluts: Audrey Rose and Lea Lexis

FapHouse 3 months ago

Master & Ithan Private Show

54% HD 2:00 / 9:40

Master & Ithan Private Show

Flirt4Free 1 year ago

Sissy bride chastity - Wedding night tease

50% 0:11 / 12:31

Sissy bride chastity - Wedding night tease

Clips4sale 2 years ago

Sissy Maid Dee Gets Carried Away Riding Dildos

HD 1:01 / 10:12

Sissy Maid Dee Gets Carried Away Riding Dildos

FapHouse 3 days ago

Lika Kai Private Show

Lika Kai Private Show

Flirt4Free 1 week ago

Stepmother Teaches Her Transgender Stepdaughter How to Perform Rituals to Bring a Slave to Orgasm

48% HD 0:39 / 7:52

Stepmother Teaches Her Transgender Stepdaughter How to Perform Rituals to Bring a Slave to Orgasm

FapHouse 5 months ago

Anal Punishment with Melany Furie

HD 0:39 / 23:36

Anal Punishment with Melany Furie

FapHouse 3 weeks ago

Piss as punishment (720p)

62% HD 0:13 / 4:18

Piss as punishment (720p)

Clips4sale 4 years ago

Sexy femdom tranny on bike ride! Ballbusting and CBT for horny camery guy!

HD 0:30 / 11:58

Sexy femdom tranny on bike ride! Ballbusting and CBT for horny camery guy!

Clips4sale 2 months ago

The Legal Aid: Chelsea Marie and Dale Savage

HD 1:40 / 32:44

The Legal Aid: Chelsea Marie and Dale Savage

KinkTrans 4 years ago

Sophia Loreen Private Show

4K 2:00 / 14:29

Sophia Loreen Private Show

Flirt4Free 5 days ago

Lora Bakers Private Show

HD 2:00 / 24:21

Lora Bakers Private Show

Flirt4Free 2 years ago

The Ultimate Prostate Exam

46% HD 0:10 / 11:47

The Ultimate Prostate Exam

LoyalFans 2 years ago

Sexy striptease, savage twerk naked, fingering and more ;)

Sexy striptease, savage twerk naked, fingering and more ;)

Flirt4Free 5 years ago

Sophia Loreen Pillow Cowgirl Ride

HD 2:00 / 11:08

Sophia Loreen Pillow Cowgirl Ride

Flirt4Free 3 years ago

fucked him before work. hardcore pegging!

48% HD 0:27 / 9:05

fucked him before work. hardcore pegging!

AnalVids 1 year ago

Lika Kai Private Show

61% 4K 2:00 / 8:46

Lika Kai Private Show

Flirt4Free 3 days ago

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Piss

70% HD 0:39 / 31:35

Rans Ria Bentley Makes Dolly Rotten Snort Cum and Eat Her Piss

FapHouse 5 months ago

9:55 of glossy black tape punishment in crisp HD. Bad girls get completely wrapped – and tonight I was wrapped in nothing but matte black PVC tape.

9:55 of glossy black tape punishment in crisp HD. Bad girls get completely wrapped – and tonight I was wrapped in nothing but matte black PVC tape.

Clips4sale 10 months ago

Ambar & Oliver Private Show

60% HD 2:00 / 7:59

Ambar & Oliver Private Show

Flirt4Free 5 months ago

Elvis & Alfonso & Master Private Show

62% HD 2:00 / 14:58

Elvis & Alfonso & Master Private Show

Flirt4Free 4 years ago

Pegging gangbang for naughty students

59% 0:21 / 12:59

Pegging gangbang for naughty students

Clips4sale 3 years ago

Liam Jacobson Private Show

62% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 10 months ago

$Hot Dildo Cumshow, we\'re starting with tease, light touches and then we go deeper and naughty. Let\'s cum together guys - Part 2$ HD 2:00 / 24:49

Hot Dildo Cumshow, we\'re starting with tease, light touches and then we go deeper and naughty. Let\'s cum together guys - Part 2

Flirt4Free 1 year ago

TS step-daughter Slut Training

55% HD 0:10 / 15:25

TS step-daughter Slut Training

LoyalFans 2 months ago

Michael Hawtin Private Show

Michael Hawtin Private Show

Flirt4Free 1 year ago

Asian Trans Stroking and Cumming

51% HD 2:00 / 18:44

Asian Trans Stroking and Cumming

Flirt4Free 7 years ago

Colombian Boys Private Show

Colombian Boys Private Show

Flirt4Free 1 week ago

SHEMALE DOMINATION - 33 - YASMIN DE CASTRO & RICK BITCH - FULL VERSION - WMV

67% 0:30 / 21:45

SHEMALE DOMINATION - 33 - YASMIN DE CASTRO & RICK BITCH - FULL VERSION - WMV

Clips4sale 2 years ago

Bought & Broken In (1080 HD)

71% 4K 0:53 / 20:39

Bought & Broken In (1080 HD)

Clips4sale 4 years ago

Stuard & Jhordy & Ronaldo Private Show

61% HD 2:00 / 6:10

Stuard & Jhordy & Ronaldo Private Show

Flirt4Free 2 years ago

Femdom Trans Orgy with prisioners - BDSM - Humiliation - Big Butts - Big Cocks --

Premium HD 45:21

Femdom Trans Orgy with prisioners - BDSM - Humiliation - Big Butts - Big Cocks --

Clips4sale 1 month ago

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

63% HD 1:34 / 48:12

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

KinkTrans 9 years ago

Shemale Yanka Disgusting Farting Punishment II

Premium HD 5:10

Shemale Yanka Disgusting Farting Punishment II

Clips4sale 1 day ago

Sex Offender

66% HD 1:01 / 52:23

FapHouse 1 month ago

Patric & Oliver Private Show

64% HD 2:00 / 14:54

Patric & Oliver Private Show

Flirt4Free 4 years ago

italian tranny anna hickiman punishes wardrobe attendant

HD 0:30 / 46:40

italian tranny anna hickiman punishes wardrobe attendant

AnalVids 3 years ago

Subservient tranny Daisy Taylor punished by tattooed master H3ll4SL00tz

Subservient tranny Daisy Taylor punished by tattooed master H3ll4SL00tz

ShemalesTube 5 years ago

Futa Punishes Her Step-slut

59% 0:39 / 19:11

Futa Punishes Her Step-slut

FapHouse 8 months ago

pegging him with my two side strapon

pegging him with my two side strapon

PornBox 1 year ago

Anal Fingering

Flirt4Free 4 years ago

Sarait Gil Private Show

61% HD 2:00 / 6:20

Sarait Gil Private Show

Flirt4Free 2 years ago

Step-Mommy comes home to tease her PetGirl- Variety Itsol

Step-Mommy comes home to tease her PetGirl- Variety Itsol

Clips4sale 1 year ago

Colombian Boys Private Show

47% HD 2:00 / 23:35

Colombian Boys Private Show

Flirt4Free 2 years ago

Zara Clark Private Show

Zara Clark Private Show

Flirt4Free 5 months ago

Marian & Richard Private Show

57% HD 2:00 / 20:44

Marian & Richard Private Show

Flirt4Free 1 month ago

Celeste & Liz Private Show

62% HD 2:00 / 4:37

Celeste & Liz Private Show

Flirt4Free 3 years ago

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