Chastity Training (51,106)

Ava Maddison Private Show

64% 4K 2:00 / 6:12

Ava Maddison Private Show

Flirt4Free 1 week ago

Gwen Drew Party on Feb 21, 2026 - Part 2

61% 4K 2:00 / 46:31

Gwen Drew Party on Feb 21, 2026 - Part 2

Flirt4Free 2 days ago

Viky & Mateo Private Show

62% HD 2:00 / 4:35

Viky & Mateo Private Show

Flirt4Free 1 month ago

Kennya and Faith chastity and toilet slavery for life

61% HD 0:10 / 16:00

Kennya and Faith chastity and toilet slavery for life

LoyalFans 2 years ago

Sissy Chastity Training with Two BBC

57% 0:11 / 20:25

Sissy Chastity Training with Two BBC

Clips4sale 8 months ago

Sissy Slave's First Stretching

68% HD 0:10 / 26:49

Sissy Slave's First Stretching

LoyalFans 3 years ago

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

51% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 3 months ago

Train My Ass Miss Dia, Plllllease!

58% HD 1:01 / 46:44

Train My Ass Miss Dia, Plllllease!

FapHouse 1 year ago

Viky & Mateo Private Show

67% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 1 month ago

Cuckold Watches Anal Sex and Gets to Clean Up Afterwards

Cuckold Watches Anal Sex and Gets to Clean Up Afterwards

xHamster 1 month ago

The slave training of Bobbi Starr: Day 2

65% HD 1:01 / 43:38

The slave training of Bobbi Starr: Day 2

FapHouse 8 years ago

Fun Feminization

49% HD 0:10 / 5:34

Fun Feminization

LoyalFans 7 months ago

Sissy Stash Discovered

51% HD 0:10 / 6:14

Sissy Stash Discovered

LoyalFans 1 day ago

Cumming from Jerking off in Chastity on Leather High Heel Boots for Pathetic Slave Pup

Cumming from Jerking off in Chastity on Leather High Heel Boots for Pathetic Slave Pup

xHamster 1 year ago

LOCKTOBER MILKING / HUCOW

48% HD 0:10 / 9:28

LOCKTOBER MILKING / HUCOW

LoyalFans 4 months ago

Training And Teasing My Butler - Chastity Orgasm Denial

Training And Teasing My Butler - Chastity Orgasm Denial

xHamster 1 year ago

Using Lowly Servant for My Pleasure! Erotica! *custom Clip*

69% HD 1:01 / 9:28

Using Lowly Servant for My Pleasure! Erotica! *custom Clip*

FapHouse 8 months ago

The slave training of Bobbi Starr: Day 1

51% HD 1:01 / 1:22:05

The slave training of Bobbi Starr: Day 1

FapHouse 8 years ago

Educating a Bitch Boy Episode: 1

67% HD 0:39 / 44:39

Educating a Bitch Boy Episode: 1

FapHouse 2 years ago

Sweet & Daaniel Private Show

57% HD 2:00 / 12:04

Sweet & Daaniel Private Show

Flirt4Free 1 month ago

Monster dicks and the Goddesses who wield them

68% HD 0:10 / 9:18

Monster dicks and the Goddesses who wield them

LoyalFans 3 years ago

Cum Collar And Cage Challenge

57% HD 0:10 / 10:54

Cum Collar And Cage Challenge

LoyalFans 4 months ago

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

57% HD 0:39 / 12:35

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

FapHouse 3 weeks ago

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

lick my pussy after pissing. oh yes good bitch. feminization of the stepbrother.

PissVids 3 years ago

1st Sissy Experience With Miss Shell

57% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 2 years ago

Sissy compilation volume 2

51% HD 1:01 / 13:42

Sissy compilation volume 2

FapHouse 3 years ago

Educating a Bitchboy: Episode 4 "last Chance"

74% HD 1:01 / 1:02:24

Educating a Bitchboy: Episode 4 "last Chance"

FapHouse 6 months ago

Stunning moment from "3D Metal Bondage and Latex Compilation"

Stunning moment from "3D Metal Bondage and Latex Compilation"

xHamster 4 months ago

Japanese Femdom Human Chair and Ponyboy

57% HD 0:39 / 14:46

Japanese Femdom Human Chair and Ponyboy

FapHouse 1 year ago

Absolute Obedience 2

45% HD 1:01 / 12:14

Absolute Obedience 2

FapHouse 5 months ago

Femdom marriage: trained to suck for Miss Ema’s pleasure by Matriarch Ezada Sinn and Mistress Kennya

65% HD 0:10 / 13:01

Femdom marriage: trained to suck for Miss Ema’s pleasure by Matriarch Ezada Sinn and Mistress Kennya

LoyalFans 10 months ago

Ass Worship Reward: Giada Da Vinci licks My sweat in chastity in my gym

65% HD 0:10 / 10:36

Ass Worship Reward: Giada Da Vinci licks My sweat in chastity in my gym

LoyalFans 4 months ago

Sissy Gets Caught

Sissy Gets Caught

LoyalFans 2 months ago

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

65% HD 0:39 / 12:35

Caged Sissy Cuckold Gaming - Mistress Gives Slave in Chastity a Handjob with Ruined Orgasm

FapHouse 3 weeks ago

Brittney & Elvis Private Show

53% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 2 years ago

Pegging, Cuckolding and Training - Adreena Winters & The Cuckold Diary

62% HD 0:10 / 36:17

Pegging, Cuckolding and Training - Adreena Winters & The Cuckold Diary

LoyalFans 11 months ago

Viky & Mateo Private Show

69% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 1 month ago

Mistress Makes Masochist Wear Chastity Belt and Locks It, Then Puts the Key on Her Necklace and Controls Him

Mistress Makes Masochist Wear Chastity Belt and Locks It, Then Puts the Key on Her Necklace and Controls Him

xHamster 2 weeks ago

Part 2: How Do You Reframe a Disobedient Hairy Slave? Turn Him Into a Pet- Maitresse Julia

68% 1:01 / 5:48

Part 2: How Do You Reframe a Disobedient Hairy Slave? Turn Him Into a Pet- Maitresse Julia

FapHouse 1 year ago

Ava Maddison Private Show

66% 4K 2:00 / 8:28

Ava Maddison Private Show

Flirt4Free 1 week ago

Total Transformation - HD

39% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 7 months ago

Testing My New house slave feat Bambi Femdom

53% HD 0:10 / 6:21

Testing My New house slave feat Bambi Femdom

LoyalFans 5 months ago

Using Lowly Servant for My Pleasure! Erotica! *custom Clip*

65% HD 0:39 / 9:28

Using Lowly Servant for My Pleasure! Erotica! *custom Clip*

FapHouse 8 months ago

my step brother becomes my step sister- sissy. sissy cums in a chastity cage. syssification.

my step brother becomes my step sister- sissy. sissy cums in a chastity cage. syssification.

PornBox 2 years ago

Sissy Training in Chastity

57% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Viky & Mateo Private Show

59% HD 2:00 / 4:46

Viky & Mateo Private Show

Flirt4Free 1 month ago

Edging and Sounding by Dominafire

65% 0:39 / 24:43

Edging and Sounding by Dominafire

FapHouse 1 year ago

Prissy sissy Dolly - Locked in frills

60% HD 0:10 / 13:13

Prissy sissy Dolly - Locked in frills

LoyalFans 7 months ago

Viky & Mateo Private Show

60% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 1 month ago

POV - Predicament - Endurance - Spider Web - Pegging (244)

58% 1:01 / 26:05

POV - Predicament - Endurance - Spider Web - Pegging (244)

FapHouse 2 weeks ago

My Bull Called, He Wants Us Both to Prepare Our Asses

46% HD 1:01 / 19:18

My Bull Called, He Wants Us Both to Prepare Our Asses

FapHouse 2 months ago

Passing the Torch: Anal Pornstar Ava Devine Breeds a New Anal Slut

65% HD 0:10 / 37:16

Passing the Torch: Anal Pornstar Ava Devine Breeds a New Anal Slut

LoyalFans 4 months ago

Femdom Pegging Gangbang

65% HD 0:39 / 12:36

Femdom Pegging Gangbang

FapHouse 1 week ago

Viky & Mateo Private Show

56% HD 2:00 / 4:48

Viky & Mateo Private Show

Flirt4Free 1 month ago

Sissy-schlampe Wird Bestraft!

Sissy-schlampe Wird Bestraft!

FapHouse 5 months ago

Chastity Tease and taken for training: Matriarch Ezada Sinn and Mistress Luna torment blindfolded chattel

HD 0:10 / 16:33

Chastity Tease and taken for training: Matriarch Ezada Sinn and Mistress Luna torment blindfolded chattel

LoyalFans 2 weeks ago

Making StepBro My Step-Sissy: Telling My Friends Pt 3 Feat Aria Nicole 4K

4K 0:10 / 10:11

Making StepBro My Step-Sissy: Telling My Friends Pt 3 Feat Aria Nicole 4K

LoyalFans 2 weeks ago

Sissy Step 5

49% HD 0:10 / 17:04

LoyalFans 1 year ago

Anal Stretching on the First Date

46% HD 0:39 / 12:53

Anal Stretching on the First Date

FapHouse 5 months ago

Red Lips Tease and Pussyplay

59% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 2 years ago

Life in My cage

52% HD 0:10 / 6:07

Life in My cage

LoyalFans 3 years ago

Weights on nipple clamps

49% HD 0:10 / 6:46

Weights on nipple clamps

LoyalFans 4 months ago

Using male objects at the OWK

68% HD 0:10 / 7:59

Using male objects at the OWK

LoyalFans 4 years ago

Katharine Cane Party on Feb 15, 2026 - Part 2

4K 2:00 / 14:42

Katharine Cane Party on Feb 15, 2026 - Part 2

Flirt4Free 1 week ago

Chastity patient prostate exam by DominaFire 1/2

57% 1:01 / 5:05

Chastity patient prostate exam by DominaFire 1/2

FapHouse 2 years ago

Chastity Obedience slave Training!

57% HD 0:10 / 8:04

Chastity Obedience slave Training!

LoyalFans 3 months ago

Two Days with My Well-trained Pup Rufus - Mistress Julia

HD 1:01 / 42:19

Two Days with My Well-trained Pup Rufus - Mistress Julia

FapHouse 1 week ago

Gwen Drew Private Show

56% 4K 2:00 / 1:22:02

Gwen Drew Private Show

Flirt4Free 2 months ago

CHASTITY TRAINING WITH VAGINAL PLUG AND ANAL PLAY

65% HD 0:10 / 8:02

CHASTITY TRAINING WITH VAGINAL PLUG AND ANAL PLAY

LoyalFans 8 months ago

Boyfriend Slave Training (Chastity Tease & Ruined Orgasm)

HD 0:10 / 23:04

Boyfriend Slave Training (Chastity Tease & Ruined Orgasm)

LoyalFans 1 month ago

Training Zero Femdom Cum Ruined Orgasm in Chastity Cage Post Orgasm Ballbusting CBT Real Homemade Milf Stepmom Bondage BDSM

Training Zero Femdom Cum Ruined Orgasm in Chastity Cage Post Orgasm Ballbusting CBT Real Homemade Milf Stepmom Bondage BDSM

xHamster 1 year ago

Cock Sucking Cuckold

62% HD 0:10 / 34:18

Cock Sucking Cuckold

LoyalFans 1 year ago

Sissy husbands cock caged and fucked in his ass with mistress's big strapon

Sissy husbands cock caged and fucked in his ass with mistress's big strapon

xHamster 2 years ago

I Trained My Chastity Slave To Squirt In His Cage! - Hell Never Be Free Again

I Trained My Chastity Slave To Squirt In His Cage! - Hell Never Be Free Again

AbBDSM 4 days ago

Mistressae & Lady Valeska’s Anal Stretching School: Second Semester

65% HD 1:01 / 8:37

Mistressae & Lady Valeska’s Anal Stretching School: Second Semester

FapHouse 7 months ago

The Bimbofication Serum

58% HD 0:10 / 16:32

The Bimbofication Serum

LoyalFans 2 years ago

From Worthless to Worthy in Five Mistresses Episode 3, "chastity CBT"

56% HD 1:01 / 55:13

From Worthless to Worthy in Five Mistresses Episode 3, "chastity CBT"

FapHouse 2 months ago

Christina Callaway Private Show

Christina Callaway Private Show

Flirt4Free 2 weeks ago

Chastity Training, Humiliation and Cock on Ice Punishment with Mistress Lexy Noir

HD 0:10 / 11:56

Chastity Training, Humiliation and Cock on Ice Punishment with Mistress Lexy Noir

LoyalFans 1 day ago

Viky & Mateo Private Show

60% HD 2:00 / 44:54

Viky & Mateo Private Show

Flirt4Free 1 month ago

Stinky Chinese Asian Feet Domination Permanent Chastity Key Flush Orgasm Denial Tease & Denial Sweaty Soles POV Femdom Foot Slave Training - Permanent Denial - Chastity Ruin Sissy Slave Foot Worship , stinky feet, sweaty feet, Chinese feet

Stinky Chinese Asian Feet Domination Permanent Chastity Key Flush Orgasm Denial Tease & Denial Sweaty Soles POV Femdom Foot Slave Training - Permanent Denial - Chastity Ruin Sissy Slave Foot Worship , stinky feet, sweaty feet, Chinese feet

Clips4sale 3 weeks ago

Examining the Teachers Pet: Episode 4 "the Eastern European Dominatrix"

67% HD 1:01 / 49:20

Examining the Teachers Pet: Episode 4 "the Eastern European Dominatrix"

FapHouse 5 months ago

Autumn Woods Party on Jan 21, 2026 - Part 2

HD 2:00 / 55:27

Autumn Woods Party on Jan 21, 2026 - Part 2

Flirt4Free 1 month ago

Female Instructors Make Slaves Jerk off in Front of Them, Put Ice on Dicks Just Before Cum, and Put on Chastity Belts

66% HD 0:39 / 16:13

Female Instructors Make Slaves Jerk off in Front of Them, Put Ice on Dicks Just Before Cum, and Put on Chastity Belts

FapHouse 1 year ago

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

47% HD 0:39 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 3 months ago

We own his Ass with our Strap-On Cocks

64% HD 0:10 / 20:15

We own his Ass with our Strap-On Cocks

LoyalFans 3 months ago

MERCILESS HOT WIFE - HOLD THE DILDO IN YOUR MOUTH WHILE I SLAP YOU HARD! - CRUEL BITCHSLAP TRAINING

57% HD 0:10 / 14:37

MERCILESS HOT WIFE - HOLD THE DILDO IN YOUR MOUTH WHILE I SLAP YOU HARD! - CRUEL BITCHSLAP TRAINING

LoyalFans 1 month ago

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

58% HD 0:10 / 16:20

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

LoyalFans 1 year ago

Sissy Training in the Dungeon

55% HD 0:10 / 13:29

Sissy Training in the Dungeon

LoyalFans 1 year ago

Meryem Basharaa Private Show

49% HD 2:00 / 4:00

Meryem Basharaa Private Show

Flirt4Free 1 year ago

Fall into Temptation: test your commitment, inspire weakness Andrea Rosu

64% HD 0:10 / 13:30

Fall into Temptation: test your commitment, inspire weakness Andrea Rosu

LoyalFans 1 year ago

Sissy Step 7

48% HD 0:10 / 21:22

LoyalFans 1 year ago

Stepdaughter Humiliator - Kendra James & Star Nine

49% HD 0:10 / 7:49

Stepdaughter Humiliator - Kendra James & Star Nine

LoyalFans 2 years ago

Normalize Chastity

HD 0:10 / 10:50

Normalize Chastity

LoyalFans 3 years ago

Milking in Sissy Mouth and Pegging Training

66% HD 1:01 / 16:24

Milking in Sissy Mouth and Pegging Training

FapHouse 1 year ago

Matching Panties & a Locked up Cock

Matching Panties & a Locked up Cock

xHamster 1 year ago

AFTERNOON PEGGING: feminized boyfriend gets his ass pounded by mommy

AFTERNOON PEGGING: feminized boyfriend gets his ass pounded by mommy

xHamster 8 months ago

Doctor's Orders: Your Weakened Wrist Merits Professional Masturbatory Guidance

66% HD 0:10 / 31:57

Doctor's Orders: Your Weakened Wrist Merits Professional Masturbatory Guidance

LoyalFans 3 years ago

How Do You Reframe a Disobedient Hairy Slave? Turn Him Into a Pet - Maitresse Julia

66% 0:39 / 7:20

How Do You Reframe a Disobedient Hairy Slave? Turn Him Into a Pet - Maitresse Julia

FapHouse 1 year ago

Hold the position – pain is just weakness leaving the body

66% HD 0:10 / 12:08

Hold the position – pain is just weakness leaving the body

LoyalFans 2 weeks ago

Breath taking face sitting remastered: Matriarch Ezada Sinn trains Her human cushion with Her pantyhose-clad arse

65% HD 0:10 / 8:12

Breath taking face sitting remastered: Matriarch Ezada Sinn trains Her human cushion with Her pantyhose-clad arse

LoyalFans 9 months ago

Chastity Cage, Pegging, Xxl Toys and Deep Fisting with a French MILF

HD 0:39 / 22:49

Chastity Cage, Pegging, Xxl Toys and Deep Fisting with a French MILF

FapHouse 2 weeks ago

Kiss my feet, chastity slut!

76% HD 1:01 / 8:37

Kiss my feet, chastity slut!

FapHouse 5 years ago

Chelsea Roset Private Show

63% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 2 years ago

Teasing my butler's cock during My reading and coffee time

Teasing my butler's cock during My reading and coffee time

xHamster 1 year ago

He Tries to Escape When Trapped for Anal Penetration

58% HD 0:39 / 25:39

He Tries to Escape When Trapped for Anal Penetration

FapHouse 1 year ago

Ares & Adara Private Show

46% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 1 year ago

Super Sadistic Teasing for His Cock and Balls

56% HD 0:10 / 16:26

Super Sadistic Teasing for His Cock and Balls

LoyalFans 1 week ago

My Husband Sissified: A Female Latex Slave Doll Pegged - Mistress Julia feat. Sukeban

58% 4K 0:10 / 20:46

My Husband Sissified: A Female Latex Slave Doll Pegged - Mistress Julia feat. Sukeban

LoyalFans 5 months ago

How Do You Reframe a Disobedient Hairy Slave? Turn Him Into a Pet - Maitresse Julia

55% 1:01 / 7:20

How Do You Reframe a Disobedient Hairy Slave? Turn Him Into a Pet - Maitresse Julia

FapHouse 1 year ago

Lock-up Tease & Denial

HD 1:01 / 10:14

Lock-up Tease & Denial

FapHouse 1 week ago

Training Guide: Sissy Cuckold Husband

57% 4K 0:10 / 34:44

Training Guide: Sissy Cuckold Husband

LoyalFans 3 years ago

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

55% HD 0:10 / 2:40:24

FULL LIVE - Sissification Slumber Party & Beta Bullying - Featuring Goddess Jay

LoyalFans 2 weeks ago

Caged Sissy Has to Suck Her First Real Cock

HD 0:39 / 12:30

Caged Sissy Has to Suck Her First Real Cock

FapHouse 6 months ago

Lock It Up! Chastity Training Orgasm Denial Strict Control Femdom POV by Goddess Kyaa

53% HD 0:10 / 11:23

Lock It Up! Chastity Training Orgasm Denial Strict Control Femdom POV by Goddess Kyaa

LoyalFans 1 month ago

Lingerie Lover - Sissy Pegging POV

59% HD 1:01 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 11 months ago

Sissies Service Real Men

66% HD 0:10 / 17:19

Sissies Service Real Men

LoyalFans 3 years ago

He Finally Gets to Fuck His Empress - Not with His Cock Though:)

63% 1:01 / 9:40

He Finally Gets to Fuck His Empress - Not with His Cock Though:)

FapHouse 3 weeks ago

Matriarch Ezada Sinn’s strap-on training: from anal obsession to full toilet servitude

71% HD 0:10 / 13:33

Matriarch Ezada Sinn’s strap-on training: from anal obsession to full toilet servitude

LoyalFans 10 months ago

Step-Mommy’s Rubber Boy: Femdom Pegging, Fisting, Facesitting, & Chastity - Full-length 1-HR of Female Domination (1080p)

62% HD 0:29 / 1:02:20

Step-Mommy’s Rubber Boy: Femdom Pegging, Fisting, Facesitting, & Chastity - Full-length 1-HR of Female Domination (1080p)

Clips4sale 1 year ago

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