Chastity Training - Sex Videos (97,901)

Cuckold Watches Anal Sex and Gets to Clean Up Afterwards

Cuckold Watches Anal Sex and Gets to Clean Up Afterwards

XHamster 5 months ago

She Locked Me in Chastity and Showed Me How She Fucks

She Locked Me in Chastity and Showed Me How She Fucks

XHamster 3 weeks ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 4 years ago

Grisha Mochka Private Show

71% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 2 weeks ago

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

59% HD 1:01 / 55:13

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

FapHouse 7 months ago

Katharine Cane Party on Jul 4, 2026 - Part 2

55% HD 2:00 / 50:15

Katharine Cane Party on Jul 4, 2026 - Part 2

Camster 1 week ago

Educating a Bitchboy Episode: 2

Educating a Bitchboy Episode: 2

XHamster 1 year ago

Wedding Bride Chastity Strapon Fuck | Mistress Nalini

73% HD 0:10 / 15:11

Wedding Bride Chastity Strapon Fuck | Mistress Nalini

LoyalFans 2 months ago

If you don't keep your hands off your cock I will do it for you!

Premium HD 53:43

If you don't keep your hands off your cock I will do it for you!

Kink 12 years ago

The Education of Chastity Lynn - Lesbian Reform Skool!

55% HD 1:01 / 1:18:47

The Education of Chastity Lynn - Lesbian Reform Skool!

FapHouse 1 month ago

Chastity Belts Plus Verbal Training

59% HD 1:01 / 1:18:34

Chastity Belts Plus Verbal Training

FapHouse 4 months ago

Lady Caitlyn Party on Jun 30, 2026

49% HD 2:00 / 1:00:18

Lady Caitlyn Party on Jun 30, 2026

Camster 1 week ago

LOCKTOBER MILKING / HUCOW

51% HD 0:10 / 9:28

LOCKTOBER MILKING / HUCOW

LoyalFans 9 months ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

XHamster 2 years ago

Lunge whipping

61% HD 0:10 / 10:02

LoyalFans 3 months ago

Cuckold Cleanup Compilation Vol 1: Real Creampie Eating Sessions - The Cuckold Diary [4K Ultra HD]

71% 4K 0:46 / 27:47

Cuckold Cleanup Compilation Vol 1: Real Creampie Eating Sessions - The Cuckold Diary [4K Ultra HD]

Clips4sale 2 months ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Chastity Belts Plus Verbal Training

Chastity Belts Plus Verbal Training

XHamster 4 weeks ago

Sexy Asian Mistress Dominates You

Sexy Asian Mistress Dominates You

FapHouse 2 weeks ago

Sissy Wife Pegged In Chastity - Clara Dee POV

Sissy Wife Pegged In Chastity - Clara Dee POV

XHamster 2 years ago

7-day Foot Obedience Trial

HD 1:01 / 14:03

7-day Foot Obedience Trial

FapHouse 1 week ago

Slave Graduation Final Test Extreme Torment and Obedience Training for blonde Chastity Lynn

Slave Graduation Final Test Extreme Torment and Obedience Training for blonde Chastity Lynn

Eporner 8 months ago

2 Dildos 1 Chastity Cage Anal JOI

57% HD 0:10 / 9:47

2 Dildos 1 Chastity Cage Anal JOI

LoyalFans 2 years ago

Khloe Clark Private Show

50% 4K 2:00 / 24:07

Khloe Clark Private Show

Camster 3 weeks ago

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

64% HD 1:01 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 3 weeks ago

Pool Party Pegging

65% HD 0:10 / 16:35

Pool Party Pegging

LoyalFans 1 week ago

Femdom POV Sissy Training Pleasure Him

48% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Sophie Elodie – steel ballet heels

80% 4K 0:10 / 4:53

Sophie Elodie – steel ballet heels

Clips4sale 1 year ago

Female Instructors Make Slaves Lick Their Pussies While They Eat

48% HD 0:39 / 5:11

Female Instructors Make Slaves Lick Their Pussies While They Eat

FapHouse 1 year ago

POV Cuckold volume 20

POV Cuckold volume 20

XHamster 4 years ago

Chastity Come Back

HD 0:10 / 15:49

Chastity Come Back

LoyalFans 3 weeks ago

Romantic Chastity

HD 0:10 / 13:31

Romantic Chastity

LoyalFans 1 week ago

Maximum Torture - Screwed After Climax

Maximum Torture - Screwed After Climax

Amateur8 2 weeks ago

The slave training of Bobbi Starr: Day 2

64% HD 1:01 / 43:44

The slave training of Bobbi Starr: Day 2

FapHouse 8 years ago

Lock and Key

XHamster 4 months ago

Sissy Academy Part 1

Sissy Academy Part 1

XHamster 9 months ago

Chastity Belt Cuffed job training

Chastity Belt Cuffed job training

BDSMX 6 months ago

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

FILIPINA DOMINATRIX PEGGING WHITE CHASTITY SLAVE

XHamster 4 years ago

Toilet Must Swallow

50% HD 1:01 / 13:06

Toilet Must Swallow

FapHouse 2 months ago

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

50% HD 0:39 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 3 weeks ago

chastity training instructions cock cage sissy slave rubberband snaps ball torture

chastity training instructions cock cage sissy slave rubberband snaps ball torture

Itsrealamateurs 4 days ago

Femdom pegging with 8 inch strapon

Femdom pegging with 8 inch strapon

XHamster 8 months ago

2 Mean Girls - His first Day as a Slave

2 Mean Girls - His first Day as a Slave

XHamster 5 months ago

Electro Sissy Begs to Cum

HD 0:10 / 10:11

Electro Sissy Begs to Cum

LoyalFans 1 year ago

I open her chastity belt to only edge her and lock her back up - Watch her reaction

I open her chastity belt to only edge her and lock her back up - Watch her reaction

EpicGFs 2 years ago

Isadora Dunkan Private Show

65% 4K 2:00 / 10:17

Isadora Dunkan Private Show

Camster 1 week ago

Sissy-academy Part 1 - Sissys Chastity

62% HD 0:39 / 5:11

Sissy-academy Part 1 - Sissys Chastity

FapHouse 1 month ago

Prissy sissy dolly - Maid to be used

63% 0:30 / 13:35

Prissy sissy dolly - Maid to be used

Clips4sale 1 year ago

POV: Rubber Catsuit Hinako Takes Control; Chastity Series, Episode 31

63% 0:15 / 23:09

POV: Rubber Catsuit Hinako Takes Control; Chastity Series, Episode 31

Clips4sale 2 weeks ago

Fooled and Unfortunately No Orgasm

Fooled and Unfortunately No Orgasm

XHamster 10 months 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

Manu Eyngri Private Show

4K 2:00 / 14:29

Manu Eyngri Private Show

Camster 5 days ago

CBT, handjob and humiliation by Mistress Luna

CBT, handjob and humiliation by Mistress Luna

Clips4sale 1 year ago

Mistress gives her slave a large enema training for failing the anal challenge

Mistress gives her slave a large enema training for failing the anal challenge

XHamster 4 years ago

Pantyhose Chastity Tease & Encouragement Ebony FemDom POV | Mistress Nalini

66% 0:29 / 14:54

Pantyhose Chastity Tease & Encouragement Ebony FemDom POV | Mistress Nalini

Clips4sale 2 weeks ago

The slave training of Bobbi Starr: Day 1

The slave training of Bobbi Starr: Day 1

XHamster 4 months ago

The Education of Chastity Lynn - Lesbian Reform Skool!

60% HD 0:39 / 1:18:47

The Education of Chastity Lynn - Lesbian Reform Skool!

FapHouse 1 month ago

Lady Caitlyn Party on Jun 25, 2026

HD 2:00 / 1:35:27

Lady Caitlyn Party on Jun 25, 2026

Camster 2 weeks ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

XHamster 2 years ago

Guiding you through chastity - Countess Diamond's Chastity Training Program

Guiding you through chastity - Countess Diamond's Chastity Training Program

Pornzona 3 weeks ago

From Business Man To Serving Girl (HD MP4)

4K 0:30 / 14:13

From Business Man To Serving Girl (HD MP4)

Clips4sale 3 years ago

The Dominique Doll!

57% 4K 0:10 / 3:59

The Dominique Doll!

Clips4sale 1 year ago

Sunday Humiliation for Sissy husband Full

Sunday Humiliation for Sissy husband Full

XHamster 1 year ago

Berlin femdom mommy chokes роре уоur throat raw

Berlin femdom mommy chokes роре уоur throat raw

AveXXX 1 week ago

Alisa – slave post

77% 4K 0:10 / 4:51

Alisa – slave post

Clips4sale 1 year ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

sissy joyce - goddess annie i love their helpless porn video

sissy joyce - goddess annie i love their helpless porn video

BDSMShip 1 year ago

Chastity Belt Cuffed Training

Chastity Belt Cuffed Training

Eporner 7 months ago

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Femdom Mistress Goddess V humiliates & fully feminizes chastity cuckold sissy sub slave w/ sph 1/3

Dafreeporn 1 year ago

The Education of Chastity Lynn - Lesbo Reform Skool!

The Education of Chastity Lynn - Lesbo Reform Skool!

FreePorn8 1 month ago

Chastity Training 1

Chastity Training 1

PornUse 6 months ago

Chastity tutorial - how to wear a chastity cage - part 1

Chastity tutorial - how to wear a chastity cage - part 1

XHamster 5 months ago

chastity belts Slavery training

chastity belts Slavery training

VivaTube 3 years ago

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

49% HD 1:01 / 19:18

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

FapHouse 7 months ago

Trained to Obey: the Start of His New Life

Trained to Obey: the Start of His New Life

XHamster 11 months ago

14 days long Anal orgasm sissy calendar - TASK

56% 0:25 / 18:08

14 days long Anal orgasm sissy calendar - TASK

Clips4sale 1 year ago

Mean Wife locked me in chastity and mads to fuck her with a strap on

Mean Wife locked me in chastity and mads to fuck her with a strap on

XHamster 1 year ago

THE PERMANENT CHASTITY OF MY HUSBAND. A SLAVE MUST BE CONTROLLED. BDSM INSTRUCTION CHASTITY BELT

Premium HD 14:18

THE PERMANENT CHASTITY OF MY HUSBAND. A SLAVE MUST BE CONTROLLED. BDSM INSTRUCTION CHASTITY BELT

XVideosRed 3 years ago

Lovely Anais Private Show

Lovely Anais Private Show

Camster 1 year ago

Asian Hotwife Turns Husband Into a Cum-eating Cuck

Asian Hotwife Turns Husband Into a Cum-eating Cuck

XHamster 3 months ago

Educating a Bitchboy: Episode 4 "last Chance"

Educating a Bitchboy: Episode 4 "last Chance"

XHamster 11 months ago

Double Domination Strap-on Worship - Chastity, femdom, Mistress Kendra + Lexi Luna sd

65% HD 0:49 / 10:37

Double Domination Strap-on Worship - Chastity, femdom, Mistress Kendra + Lexi Luna sd

Clips4sale 9 months ago

He Tries to Escape When Trapped for Anal Penetration

HD 0:30 / 25:34

He Tries to Escape When Trapped for Anal Penetration

Clips4sale 1 year ago

Make Him Bi Episode 6: Pegging Spitroast & Alpha Cock Worship Initiation with Goddess Luna Law: Making Him to Beg for Bull

HD 0:25 / 15:18

Make Him Bi Episode 6: Pegging Spitroast & Alpha Cock Worship Initiation with Goddess Luna Law: Making Him to Beg for Bull

IWantClips 4 weeks ago

Two month locked.Tease and orgasm denial

Two month locked.Tease and orgasm denial

XHamster 8 months ago

POV Cuckold vol 30

POV Cuckold vol 30

XHamster 5 months ago

Brunette and Chastity slave having some fun

Brunette and Chastity slave having some fun

XHamster 1 year ago

Bizarre StepMom Mouth Training: Enormous Gagging, ATM, Giant Anal Toys, Sissification, CBT and Golden Shower Finale! Heartless SADOMASOCHISM big beautiful woman Dominatrix-bitch

Bizarre StepMom Mouth Training: Enormous Gagging, ATM, Giant Anal Toys, Sissification, CBT and Golden Shower Finale! Heartless SADOMASOCHISM big beautiful woman Dominatrix-bitch

Amateur8 2 months ago

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 1-2

INSTITUTION X - Prostate Milking Anal Training Pspot Orgasm COMPILATION 1-2

Pornzona 1 month ago

Femdom FuckDoll

51% HD 0:25 / 24:43

Femdom FuckDoll

IWantClips 4 weeks ago

Sissy femboy makes chastity content and streams on chaturbate

Sissy femboy makes chastity content and streams on chaturbate

SortPorn 1 year ago

Whipping Bondage Object: Matriarch Ezada Sinn and Mistress Luna torment displayed chattel

HD 0:30 / 12:58

Whipping Bondage Object: Matriarch Ezada Sinn and Mistress Luna torment displayed chattel

IWantClips 4 weeks ago

Cuckold Clean Up Initiation - Queen Lucy's First Cum Eating & BBC Creampie Cleanup Training [4K Ultra HD]

65% 4K 0:30 / 31:16

Cuckold Clean Up Initiation - Queen Lucy's First Cum Eating & BBC Creampie Cleanup Training [4K Ultra HD]

Clips4sale 2 months ago

Candice Mia Private Show

63% 4K 2:00 / 4:43

Candice Mia Private Show

Flirt4Free 7 months ago

Sissy trained to swallow all the cum

53% 4K 0:16 / 7:44

Sissy trained to swallow all the cum

Clips4sale 2 years ago

Edging my pet until he shakes

Edging my pet until he shakes

Pornzona 3 weeks ago

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

61% 1:00 / 10:40

How I Destroyed My Cock (REAL Soft Cock Training) [MOV Format]

Clips4sale 4 months ago

Shaving and balls busting part 2

Shaving and balls busting part 2

XHamster 11 months ago

Cali – Trains Chastity Slave To Worship Ass FemDom

Cali – Trains Chastity Slave To Worship Ass FemDom

YepTube 1 month ago

He once again thought he was allowed to fuck

He once again thought he was allowed to fuck

XHamster 2 years ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 6 months ago

Latex Strapon Queen Pegging Slave [Short Version]

Latex Strapon Queen Pegging Slave [Short Version]

Pornfact 2 days ago

The Education of Chastity Lynn - Lesbian Reform Skool!

The Education of Chastity Lynn - Lesbian Reform Skool!

XHamster 3 weeks ago

Life in My cage

49% HD 0:10 / 6:07

Life in My cage

LoyalFans 3 years ago

$let\'s have some fun - Part 2$ 4K 2:00 / 4:52

let\'s have some fun - Part 2

Camster 2 weeks ago

Sissy in chastity - feminization - verbal instructions - anal training

HD 0:25 / 11:04

Sissy in chastity - feminization - verbal instructions - anal training

Clips4sale 1 month ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

XHamster 11 months ago

Gala Smith Private Show

Gala Smith Private Show

Camster 1 week ago

Sissy Chastity Vibrator Cum Challenge

Sissy Chastity Vibrator Cum Challenge

Pornfact 2 months ago

From Worthless to Worthy in Five Mistresses Episode 4 "chastity Woes"

From Worthless to Worthy in Five Mistresses Episode 4 "chastity Woes"

XHamster 6 months ago

My cum eating chastity slave gets to clean my feet

My cum eating chastity slave gets to clean my feet

XHamster 1 year ago

Pussy-Free Cuck Training: Pegging, Anal Fisting, Humiliation & Pussy Deprivation with Mistress Stellina Obscura

Pussy-Free Cuck Training: Pegging, Anal Fisting, Humiliation & Pussy Deprivation with Mistress Stellina Obscura

XHamster 4 months ago

Compilation Training Varias Mistress

Compilation Training Varias Mistress

XHamster 1 year ago

Bimbo rubber doll - Chastity and dick sucking

65% 0:30 / 9:47

Bimbo rubber doll - Chastity and dick sucking

Clips4sale 1 year ago

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

XHamster 1 year ago

USING lowly servant for MY pleasure! EROTICA! *CUSTOM CLIP* (sex, part 2)

77% 0:33 / 9:23

USING lowly servant for MY pleasure! EROTICA! *CUSTOM CLIP* (sex, part 2)

Clips4sale 1 year ago

elf femboy in chastity strap gets constricted butt stretched by bbc schlong and screw machine until cum

elf femboy in chastity strap gets constricted butt stretched by bbc schlong and screw machine until cum

BigTitsLust 1 year ago

Chastity belt girl outfit vlog

53% HD 0:41 / 25:42

Chastity belt girl outfit vlog

Clips4sale 2 years ago

Femdom Pegging Gangbang

Femdom Pegging Gangbang

XHamster 1 year ago

Ballbusting Bitch Boi (HD 4K MP4)

Ballbusting Bitch Boi (HD 4K MP4)

Clips4sale 2 years ago

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