Chastity Training (103,187)

The best and newest chastity training videos

Double Dom with Lady Valeska: Horny Sissy Being Sucked in the Latex Bag

61% HD 0:39 / 8:39

Double Dom with Lady Valeska: Horny Sissy Being Sucked in the Latex Bag

FapHouse 1 year ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Katharine Cane Party on Jul 6, 2026 - Part 2

56% 4K 2:00 / 6:32

Katharine Cane Party on Jul 6, 2026 - Part 2

Flirt4Free 2 months ago

Sissy Gets Caught

62% HD 0:10 / 9:26

Sissy Gets Caught

LoyalFans 8 months ago

Sissy Maid Servitude, Chastity Check, Punishment, and Throat Training

68% 0:10 / 13:09

Sissy Maid Servitude, Chastity Check, Punishment, and Throat Training

Clips4sale 1 year ago

1st Sissy Experience With Miss Shell

65% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 2 years ago

Kandi More & Jamer Private Show

57% HD 2:00 / 5:32

Kandi More & Jamer Private Show

Flirt4Free 3 years ago

Felicity Fantasy Private Show

HD 2:00 / 1:26:27

Felicity Fantasy Private Show

Camster 5 years ago

Hard-core fuck-a-thon with cane and crotchrope

Hard-core fuck-a-thon with cane and crotchrope

PornDR 10 months ago

Amber Sweeett Private Show

HD 2:00 / 17:11

Amber Sweeett Private Show

Flirt4Free 1 day ago

My owner becomes my SIssy

My owner becomes my SIssy

XHamster 2 years ago

Mistress Baton’s Sissy Finishing School Part 4 - Strapping & Caning

Mistress Baton’s Sissy Finishing School Part 4 - Strapping & Caning

LoyalFans 2 months ago

Shiny Sissy Caught Slacking and Strapped on the Swing

HD 0:10 / 16:42

Shiny Sissy Caught Slacking and Strapped on the Swing

LoyalFans 4 months ago

8 INCH Strapon fucking my chastity slut in Latex

8 INCH Strapon fucking my chastity slut in Latex

XHamster 4 years ago

Turned into a Prissy Sissy Dolly Bird! (1080p)

57% HD 0:30 / 9:44

Turned into a Prissy Sissy Dolly Bird! (1080p)

Clips4sale 2 years ago

Feminisation Bundle (720p)

68% HD 0:36 / 40:44

Feminisation Bundle (720p)

Clips4sale 1 year ago

Mistress Lady Renee - Making you dress - mp4

72% 0:16 / 14:03

Mistress Lady Renee - Making you dress - mp4

Clips4sale 1 year 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 2 months ago

Grooming care for chastity sissy

Grooming care for chastity sissy

XHamster 6 months ago

Chaste & Sissified

43% HD 0:10 / 7:19

Chaste & Sissified

LoyalFans 3 months ago

Lady Sara Borgia's Sissy School: Introduction and Instruction (1080p)

HD 0:16 / 11:44

Lady Sara Borgia's Sissy School: Introduction and Instruction (1080p)

Clips4sale 1 month ago

BBW Femdom - Pegging Chaste Sissy Anal

BBW Femdom - Pegging Chaste Sissy Anal

XHamster 2 years ago

Mistress Sophia Sahara & Goddess Slavena peg latex sissy Natalie Goth

61% 0:26 / 17:48

Mistress Sophia Sahara & Goddess Slavena peg latex sissy Natalie Goth

Clips4sale 4 years ago

Worthless husband pegged in his boi pussy whilst pathetic cock is caged up

Worthless husband pegged in his boi pussy whilst pathetic cock is caged up

XHamster 3 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

Making My Husband into a Cuckold Sissy!

50% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 3 years ago

amber slave training with foot worship porn video

amber slave training with foot worship porn video

BDSMShip 1 year ago

Slave Broken by Goddess Draya's Cruel Training Regime

Slave Broken by Goddess Draya's Cruel Training Regime

Fetishpapa 3 months ago

training zero femdom day at the beach

HD 1:17 / 11:22

training zero femdom day at the beach

PornBox 1 month ago

insanely hot huge pegging compilation #2

insanely hot huge pegging compilation #2

PornBox 1 week ago

Extreme Chastity Cock Shrinking

72% HD 0:10 / 10:41

Extreme Chastity Cock Shrinking

LoyalFans 2 years ago

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

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

XHamster 7 months ago

Penis Cage & Pegging for Submissive Husband #831

Penis Cage & Pegging for Submissive Husband #831

XHamster 7 months ago

Cuck Confessions Part 14! the Service Cuck Training the Perfect Bi Cuck

61% HD 0:39 / 29:11

Cuck Confessions Part 14! the Service Cuck Training the Perfect Bi Cuck

FapHouse 4 months ago

Chained Chastity Predicament

65% 0:30 / 11:32

Chained Chastity Predicament

Clips4sale 4 months ago

Caged And Collared For Her Pleasure (SD)

55% 0:30 / 27:27

Caged And Collared For Her Pleasure (SD)

Clips4sale 1 year ago

!!! MUST WATCH!!! Perfectly ruined orgasm

!!! MUST WATCH!!! Perfectly ruined orgasm

XHamster 5 years ago

Facesitting & Deepthroat Training

Facesitting & Deepthroat Training

XHamster 3 weeks ago

LOCKTOBER MILKING / HUCOW

49% HD 0:10 / 9:28

LOCKTOBER MILKING / HUCOW

LoyalFans 10 months ago

I Had Sex With My Sub?

57% 0:11 / 13:42

I Had Sex With My Sub?

Clips4sale 2 years ago

Bimbo rubber doll - Chastity and dick sucking

65% 0:30 / 9:47

Bimbo rubber doll - Chastity and dick sucking

Clips4sale 2 years ago

Chastity Lynn - Asshole Training For Pegging Nube

Chastity Lynn - Asshole Training For Pegging Nube

YepTube 8 months ago

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

53% HD 1:01 / 19:18

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

FapHouse 8 months ago

Adara Smith & Elver Rodriguez Private Show

63% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Camster 3 years ago

Real Dick VS Sissy Dick - SPH

60% 0:23 / 3:30

Real Dick VS Sissy Dick - SPH

Clips4sale 3 years ago

No more jerking off for you naughty boy

No more jerking off for you naughty boy

XHamster 7 years ago

Mental Cage PT 2

Mental Cage PT 2

Clips4sale 1 year ago

Chastity Bi Training (WL1711)

69% HD 0:10 / 15:09

Chastity Bi Training (WL1711)

LoyalFans 7 months ago

Training Your Ass for Me in Chastity

Training Your Ass for Me in Chastity

XHamster 1 month ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Cuckold Fantasies Volume 20

Cuckold Fantasies Volume 20

XHamster 5 years ago

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

Sissy Slut BEGS for cock all night - Hardcore Femdom Pegging with Mistress Stellina Obscura

XHamster 1 year ago

Genitalia haircut & edging for chastity slave

Genitalia haircut & edging for chastity slave

XHamster 1 year ago

Happy Humiliatrix 6

51% 0:11 / 16:27

Happy Humiliatrix 6

Clips4sale 3 years ago

Cana&rsquo_s Pet Training Joi Cbt Cei (Pet Play, Dildo Play, Chastity, NO HANDS, Denial, Ruined Orgasm)

Cana&rsquo_s Pet Training Joi Cbt Cei (Pet Play, Dildo Play, Chastity, NO HANDS, Denial, Ruined Orgasm)

XVideos 3 years ago

In Foil Bondage at the Mercy of Two Mean Mistresses

In Foil Bondage at the Mercy of Two Mean Mistresses

XVideos 2 years ago

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

HD 1:01 / 54:59

Femdom Strict Sissy Training Session: Cock Sucking, CBT, Pegging & Fisting with Mistress Stellina (1080p)

FapHouse 6 days ago

Nazanin Hunter Private Show

59% HD 2:00 / 8:38

Nazanin Hunter Private Show

Flirt4Free 3 years ago

Brittney & Elvis Private Show

58% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 3 years ago

Viky & Mateo Private Show

55% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 7 months ago

show me your stretched anal hole. bisexual husband in chastity belt as he gets fucked by mistress!

63% HD 0:15 / 5:13

show me your stretched anal hole. bisexual husband in chastity belt as he gets fucked by mistress!

PornBox 3 years ago

Earn Your Release

HD 0:10 / 11:24

Earn Your Release

LoyalFans 1 month ago

Junior & Brittney Private Show

Junior & Brittney Private Show

Camster 2 years ago

Nurse's Master Key

66% HD 0:39 / 10:22

Nurse's Master Key

FapHouse 3 months ago

i made my little sissy have a chastity orgasm

i made my little sissy have a chastity orgasm

XHamster 7 months ago

Lady Mons Private Show

45% 4K 2:00 / 26:31

Lady Mons Private Show

Flirt4Free 1 year ago

Mistress Gives Strict Training to Slave on How to Polish and Clean the Floor

Mistress Gives Strict Training to Slave on How to Polish and Clean the Floor

XHamster 1 year ago

Junior & Brittney Private Show

64% HD 2:00 / 4:02

Junior & Brittney Private Show

Flirt4Free 2 years ago

Group Milking, Edging Games: who is going to be a cumming loser with Electra Santiago, Nova Nocturnal & Alrik Angel, And Domina Andrea Rosu - Facesitting Handjob 1080

HD 1:00 / 18:56

Group Milking, Edging Games: who is going to be a cumming loser with Electra Santiago, Nova Nocturnal & Alrik Angel, And Domina Andrea Rosu - Facesitting Handjob 1080

Clips4sale 9 months ago

Viky & Mateo Private Show

56% HD 2:00 / 11:13

Viky & Mateo Private Show

Camster 7 months ago

Destroying Faces

Destroying Faces

Clips4sale 2 years ago

Office sissy training

Office sissy training

XHamster 6 months ago

Cornelia Adams Private Show

69% HD 2:00 / 4:51

Cornelia Adams Private Show

Flirt4Free 7 months ago

Lis Vega Private Show

Lis Vega Private Show

Camster 1 year ago

Cock-Lock Chastity Extension (1920x1080)

Cock-Lock Chastity Extension (1920x1080)

Clips4sale 1 year ago

Red Lips Tease and Pussyplay

49% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Camster 3 years ago

The Education of Chastity Lynn - Lesbian Reform Skool!

The Education of Chastity Lynn - Lesbian Reform Skool!

XHamster 3 months ago

$let\'s get naughty - Part 2$ 4K 2:00 / 4:52

let\'s get naughty - Part 2

Flirt4Free 1 month ago

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

teaseandthankyou - mandy marx look into my gorgeous eyes while im pegging you but dont shoot too soon porn video

BDSMShip 1 year ago

Dare to Come Closer?

64% HD 2:00 / 2:20

Dare to Come Closer?

Camster 1 year ago

Femdom POV Sissy Training Pleasure Him

48% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 5 months ago

Wanking resistance training: teased and denied in chastity by Mistress Lexy Noir

65% HD 0:10 / 13:21

Wanking resistance training: teased and denied in chastity by Mistress Lexy Noir

LoyalFans 1 year ago

Ares & Adara Private Show

61% HD 2:00 / 15:45

Ares & Adara Private Show

Camster 1 year ago

No Sex For Quick Dicks

62% HD 0:31 / 10:40

No Sex For Quick Dicks

IWantClips 2 years ago

Facesitting and Blowjob Training with Inflatable Collar

Facesitting and Blowjob Training with Inflatable Collar

XHamster 1 year ago

Viky & Mateo Private Show

55% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 7 months ago

Ares & Adara Private Show

54% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Sweet & Daaniel Private Show

63% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 2 months ago

Femdom Pov Chastity Cage Joi - Training/ Encouragement

Femdom Pov Chastity Cage Joi - Training/ Encouragement

AbXXX 1 year ago

Ultimate Japanese Electric Toy & Handjob

Ultimate Japanese Electric Toy & Handjob

Clips4sale 4 months ago

Potty Training Reversed - Ashley Edmonds

55% HD 0:10 / 12:54

Potty Training Reversed - Ashley Edmonds

LoyalFans 10 months ago

DDarkoh's Chastity Slave: Anal Training and Pegging

DDarkoh's Chastity Slave: Anal Training and Pegging

TatBabes 2 months ago

Graduation exam with two sexy teachers Madoka Hitomi and Mizuki Hayakawa

Graduation exam with two sexy teachers Madoka Hitomi and Mizuki Hayakawa

XGroovy 2 years ago

Outdoor punishment

59% 0:30 / 11:39

Outdoor punishment

Clips4sale 2 years ago

Curing Your Porn Addiction With Chastity

61% HD 0:24 / 11:14

Curing Your Porn Addiction With Chastity

IWantClips 2 years ago

Amelia Sweety Private Show

60% HD 2:00 / 4:47

Amelia Sweety Private Show

Flirt4Free 10 months ago

oubliette films - goddess serena pegging her sissy slaves boi pussy

oubliette films - goddess serena pegging her sissy slaves boi pussy

BDSMShip 3 years ago

14 ANTICHRISTmass Eve: Eternal Cuck-Faggot Damnation

57% 0:40 / 9:22

14 ANTICHRISTmass Eve: Eternal Cuck-Faggot Damnation

Clips4sale 8 months ago

Savannah Fox Vs. Fluffy with Shawn Fox Mixed Wrestling

Savannah Fox Vs. Fluffy with Shawn Fox Mixed Wrestling

XHamster 3 weeks ago

The Education of Chastity Lynn - Lesbian Reform Skool!

51% HD 1:01 / 1:18:47

The Education of Chastity Lynn - Lesbian Reform Skool!

FapHouse 3 months ago

4 Monster Dildos 4 Mistresses and 1 Slave

Premium HD 1:14

4 Monster Dildos 4 Mistresses and 1 Slave

Sheer 2 weeks ago

Chastity Belts Plus Verbal Training

Chastity Belts Plus Verbal Training

XHamster 2 months ago

Educating a Bitchboy Episode: 2

Educating a Bitchboy Episode: 2

XHamster 1 year ago

Sissified by Step-Mommy

65% HD 0:15 / 13:28

Sissified by Step-Mommy

IWantClips 2 months ago

$let\'s cum together - Part 5$ 63% 4K 2:00 / 4:52

let\'s cum together - Part 5

Camster 1 month ago

Chloe Riveiro Private Show

4K 2:00 / 12:12

Chloe Riveiro Private Show

Flirt4Free 3 days ago

The slave training of Bobbi Starr: Day 2

59% HD 1:01 / 43:44

The slave training of Bobbi Starr: Day 2

FapHouse 8 years ago

Femdom Pegging Gangbang

51% 0:39 / 11:17

Femdom Pegging Gangbang

FapHouse 6 months ago

Nika and Scarlet Venom - Content Beta Transfer

64% 0:30 / 9:17

Nika and Scarlet Venom - Content Beta Transfer

Clips 2 weeks ago

Goddess Tangent in Rubber Maid to Order

65% HD 0:25 / 39:49

Goddess Tangent in Rubber Maid to Order

IWantClips 2 months ago

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

54% HD 0:39 / 11:28

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

FapHouse 2 months ago

Gwen Drew Private Show

Gwen Drew Private Show

Camster 2 weeks ago

Slut training supergirl

Slut training supergirl

SexTVX 6 years ago

Chastity PEE and FISTING for SISSY slave

Chastity PEE and FISTING for SISSY slave

XHamster 2 years ago

Akari Niimura, Ena Satsuki (RM) Parasitic Swapping Play

Akari Niimura, Ena Satsuki (RM) Parasitic Swapping Play

Eporner 5 months ago

The Training of Slave S - Locked in Chastity

The Training of Slave S - Locked in Chastity

Lesbian8 1 year ago

Ashley Ness Private Show

63% 4K 2:00 / 9:43

Ashley Ness Private Show

Flirt4Free 2 months ago

The slave training of Bobbi Starr: Day 1

The slave training of Bobbi Starr: Day 1

XHamster 6 months ago

Kandi More & Jamer Private Show

61% HD 2:00 / 56:41

Kandi More & Jamer Private Show

Camster 3 years ago

Edging and Sounding by Dominafire

65% 1:01 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

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