Chastity Training (8,908)

The best and newest chastity training videos

My Bull Called, He Wants Us BOTH To Prepare Our Asses. He Gave Us Instructions.

My Bull Called, He Wants Us BOTH To Prepare Our Asses. He Gave Us Instructions.

Juicexxx 2 months ago

Day 5 of 7: CBT Day

Day 5 of 7: CBT Day

xHamster 2 months ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

forbidden to for my cuckold in a chastity cage

forbidden to for my cuckold in a chastity cage

xHamster 5 months ago

Chastity Sissy Acquiesces to be Cuck to get unlocked. Then Wife Pegs Butt

Chastity Sissy Acquiesces to be Cuck to get unlocked. Then Wife Pegs Butt

SortPorn 1 year ago

Muslim Hijabi mistress wearing saree while he was locked in chastity Part 1

Muslim Hijabi mistress wearing saree while he was locked in chastity Part 1

xHamster 1 month 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

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

47% HD 1:01 / 8:39

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

FapHouse 1 year ago

Junior & Brittney Private Show

63% HD 2:00 / 5:13

Junior & Brittney Private Show

Flirt4Free 1 year ago

I fuck a stranger in a parking lot to humiliate my husband

I fuck a stranger in a parking lot to humiliate my husband

xHamster 1 year ago

Wife Pisses Outdoors

Wife Pisses Outdoors

xHamster 1 week ago

The Training of Slave S - Locked in Chastity

The Training of Slave S - Locked in Chastity

Lesbian8 1 year ago

Nefertiti & Demian Private Show

57% HD 2:00 / 9:43

Nefertiti & Demian Private Show

Flirt4Free 2 years ago

Slave Training in a Cock Cage, POV, JOI, Lady Victoria Valente

Slave Training in a Cock Cage, POV, JOI, Lady Victoria Valente

xHamster 3 months 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 7 months ago

Happy Hour with Apologetic Domme - a short chastity love story

Happy Hour with Apologetic Domme - a short chastity love story

xHamster 2 years ago

I fuck my husband on the beach

I fuck my husband on the beach

xHamster 1 year ago

My husband has a new cock

My husband has a new cock

xHamster 1 year ago

POV Cuckold vol 30

POV Cuckold vol 30

xHamster 1 month ago

I lock my husband's cock in a chastity cage

I lock my husband's cock in a chastity cage

xHamster 1 year ago

Hotwife Date from the Cuckolds Point of View

Hotwife Date from the Cuckolds Point of View

xHamster 2 years ago

Training And Teasing My Butler - Chastity Orgasm Denial

Training And Teasing My Butler - Chastity Orgasm Denial

xHamster 1 year ago

ASMR sloppy caged cuck chastity cum (locktober final reward)

ASMR sloppy caged cuck chastity cum (locktober final reward)

xHamster 2 years ago

Chair Alive, Denied and Humiliated

Chair Alive, Denied and Humiliated

xHamster 1 month 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

Real Life BDSM Couple

Real Life BDSM Couple

xHamster 7 months ago

Bar Flirt Fantasy: Chastity and Sissy Transformation

Bar Flirt Fantasy: Chastity and Sissy Transformation

xHamster 6 months ago

Say Goodbye to Your First Cock Cage and Edge

Say Goodbye to Your First Cock Cage and Edge

xHamster 1 year ago

Sissy Training in Chastity

57% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Cali Carter Trains Chastity Slave To Worship Ass

Cali Carter Trains Chastity Slave To Worship Ass

AbXXX 1 year 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

Ava Maddison Private Show

66% 4K 2:00 / 8:28

Ava Maddison Private Show

Flirt4Free 1 week ago

Boyfriend's Discipline

Boyfriend's Discipline

xHamster 2 years ago

Taboo Female Supremacy - Penny Barber

Taboo Female Supremacy - Penny Barber

Lesbian8 3 weeks ago

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

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

xHamster 2 weeks ago

For My Chastity Cage Slave: Increasing Frustration

For My Chastity Cage Slave: Increasing Frustration

xHamster 1 year ago

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

xHamster 2 years ago

The evolution of the size of a chastity cage cock

The evolution of the size of a chastity cage cock

xHamster 1 year ago

On the beach, my cuckold licks my

On the beach, my cuckold licks my

xHamster 10 months 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

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 8 months ago

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

57% HD 1:01 / 22:49

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

FapHouse 2 weeks ago

The Bimbofication Serum

58% HD 0:10 / 16:32

The Bimbofication Serum

LoyalFans 2 years ago

Training Zero Femdom Slave Life Update Q&A Dominant Wife Interview with Real Married Couple

Training Zero Femdom Slave Life Update Q&A Dominant Wife Interview with Real Married Couple

xHamster 1 month ago

Ava Maddison Private Show

64% 4K 2:00 / 6:12

Ava Maddison Private Show

Flirt4Free 1 week 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

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

A sissy fetish for high heels

A sissy fetish for high heels

xHamster 3 months ago

chastity belts Slavery training

chastity belts Slavery training

WinPorn 3 years ago

Feminization of the cuckold in a chastity cage

Feminization of the cuckold in a chastity cage

PornFreeNow 6 months ago

Cuckolded, caged and humiliated

Cuckolded, caged and humiliated

xHamster 1 year ago

Chelsea Roset Private Show

63% HD 2:00 / 26:30

Chelsea Roset Private Show

Flirt4Free 2 years ago

My husband's cock is desperate in his chastity cage

My husband's cock is desperate in his chastity cage

xHamster 1 year 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

Cali Carter Trains Chastity Slave To Worship Ass

Cali Carter Trains Chastity Slave To Worship Ass

AbBDSM 1 year ago

Femdom and Cuckold Humiliation Compilation

Femdom and Cuckold Humiliation Compilation

xHamster 9 months ago

My husband lost his cock on the beach

My husband lost his cock on the beach

xHamster 2 years ago

My husband's penis frozen

My husband's penis frozen

xHamster 3 months ago

Lingerie Lover - Sissy Pegging POV

59% HD 1:01 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 11 months ago

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

68% HD 0:39 / 49:20

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

FapHouse 5 months ago

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

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

xHamster 1 month ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

Educating a Bitchboy: Episode 5 "ultimate Denial"

Educating a Bitchboy: Episode 5 "ultimate Denial"

xHamster 6 months ago

Training Guide: Sissy Cuckold Husband

57% 4K 0:10 / 34:44

Training Guide: Sissy Cuckold Husband

LoyalFans 3 years ago

POV Pink Diaper Chastity Training with Mistresse Penny Barber

POV Pink Diaper Chastity Training with Mistresse Penny Barber

MatureTubeHere 3 years ago

POV Cuckold volume 9

POV Cuckold volume 9

SortPorn 1 year 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

Taboo Female Supremacy - Penny Barber

Taboo Female Supremacy - Penny Barber

FreePorn8 4 weeks ago

Sissy Humiliation for Vanilla Party (1080p)

HD 0:19 / 10:51

Sissy Humiliation for Vanilla Party (1080p)

Clips4sale 2 weeks ago

Lady Victoria Valente - POV Anal Treatment, Cock Cage, Intensive Nipple Treatment

Lady Victoria Valente - POV Anal Treatment, Cock Cage, Intensive Nipple Treatment

xHamster 1 year ago

The Training of Slave S - Locked in Chastity

The Training of Slave S - Locked in Chastity

PornFreeNow 1 year ago

Trained Through the Screen: Denied, Rewired, Relocked -- Full Video Available

Trained Through the Screen: Denied, Rewired, Relocked -- Full Video Available

Lesbian8 7 months ago

Chastity Dressage Training

Chastity Dressage Training

AbBDSM 11 months ago

Maisa Pravo - Make me bi and chastity domination training

Maisa Pravo - Make me bi and chastity domination training

Nuvid 4 months ago

Pussy Eating Sissy (with CEI)

Pussy Eating Sissy (with CEI)

xHamster 9 months ago

Bondage Show

56% HD 2:00 / 36:00

Flirt4Free 1 year ago

Step-Mommy’s Rubber Boy Part 1 of 5: Latex Femdom Spanking, Smothering & Female Domination (1080p)

65% HD 0:28 / 12:19

Step-Mommy’s Rubber Boy Part 1 of 5: Latex Femdom Spanking, Smothering & Female Domination (1080p)

Clips4sale 1 year ago

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

Monthly Curse: Clit Tease, Electro, Ruined Orgasm

xHamster 9 months ago

Ares & Adara Private Show

46% HD 2:00 / 20:07

Ares & Adara Private Show

Flirt4Free 1 year ago

Ava Maddison Private Show

55% 4K 2:00 / 6:07

Ava Maddison Private Show

Flirt4Free 4 days ago

Masked Eva - My Favourite Way To Relax - MP4 1920x1080 HD

70% HD 0:30 / 16:03

Masked Eva - My Favourite Way To Relax - MP4 1920x1080 HD

Clips4sale 4 years ago

Sissy Wife Pegged In Chastity - Clara Dee POV

Sissy Wife Pegged In Chastity - Clara Dee POV

xHamster 2 years ago

Compilation d'humiliation femdom

Compilation d'humiliation femdom

xHamster 1 year ago

The Training of Slave S - Locked in Chastity

The Training of Slave S - Locked in Chastity

xHamster 3 years ago

Chastity Games 13 - 7 Seconds in Heaven - Clara Dee JOI Game

Chastity Games 13 - 7 Seconds in Heaven - Clara Dee JOI Game

xHamster 5 years ago

Day 5 of 7: CBT Day

Day 5 of 7: CBT Day

xHamster 1 month ago

Adara Smith & Elver Rodriguez Private Show

44% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Flirt4Free 2 years ago

Preview - Two cumshots after one week in chastity - Edging Ruined Orgasm

Preview - Two cumshots after one week in chastity - Edging Ruined Orgasm

xHamster 1 year ago

For My Chastity Cage Slave: Increasing Frustration

For My Chastity Cage Slave: Increasing Frustration

xHamster 1 year ago

Chastity Slave Fucked - Looser Training

Chastity Slave Fucked - Looser Training

xHamster 3 years ago

Fusion Ryzen Private Show

61% HD 2:00 / 16:43

Fusion Ryzen Private Show

Flirt4Free 8 months ago

Facesitters in Heat Volume 3

Facesitters in Heat Volume 3

xHamster 4 years ago

Insu Young Private Show

61% HD 2:00 / 4:05

Insu Young Private Show

Flirt4Free 12 years ago

BrookelynneBriar Good Boy Chastity Training With Stepmommy

BrookelynneBriar Good Boy Chastity Training With Stepmommy

ProPorn 2 months ago

Pussy Eating Sissy (with CEI)

Pussy Eating Sissy (with CEI)

xHamster 9 months ago

LEZ BE BAD - Nasty Tractable Hottie In Chastity Strap Gets THONG-ON Trained By Breasty Golden-haired mother I'd like to fuck

LEZ BE BAD - Nasty Tractable Hottie In Chastity Strap Gets THONG-ON Trained By Breasty Golden-haired mother I'd like to fuck

Amateur8 1 week ago

Lingerie Lover - Sissy Pegging POV

55% HD 0:39 / 15:30

Lingerie Lover - Sissy Pegging POV

FapHouse 11 months ago

Ares & Adara Private Show

53% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Isadora Dunkan Private Show

61% 4K 2:00 / 4:42

Isadora Dunkan Private Show

Flirt4Free 2 days ago

Slave Doll Aaruna Diary 2 (endless moans from electric metal butt plug and chastity belt)

Slave Doll Aaruna Diary 2 (endless moans from electric metal butt plug and chastity belt)

xHamster 1 year ago

Paintedrose.live - Taboo Milf Rosie: Cuckold Training: Cuck Serve Fluff Chastity Eat Cum

Paintedrose.live - Taboo Milf Rosie: Cuckold Training: Cuck Serve Fluff Chastity Eat Cum

AbMilf 1 year ago

Goddess Finally Got Her First Female Sub (you, Sissy)

Goddess Finally Got Her First Female Sub (you, Sissy)

xHamster 8 months ago

DOMINATRIX PEGGING CHASTITY FAGGOT

DOMINATRIX PEGGING CHASTITY FAGGOT

xHamster 2 years ago

Genny Rock Private Show

Genny Rock Private Show

Flirt4Free 3 days ago

Training Zero How to Wear Long Term Chastity Cage Femdom Orgasm Denial Slave Bondage BDSM Real Homemade Amateur Wife MILF Couple

Training Zero How to Wear Long Term Chastity Cage Femdom Orgasm Denial Slave Bondage BDSM Real Homemade Amateur Wife MILF Couple

xHamster 4 months ago

Zara Rousse Private Show

HD 2:00 / 12:24

Zara Rousse Private Show

Flirt4Free 3 weeks ago

Femdom Dominating Mistress An Li shows her boy's dick chastity

Femdom Dominating Mistress An Li shows her boy's dick chastity

MyLust 2 years ago

Viuda Nagra Private Show

62% HD 2:00 / 29:45

Viuda Nagra Private Show

Flirt4Free 2 years ago

Sissy Husband and Wife Posing

61% HD 0:39 / 2:55

Sissy Husband and Wife Posing

FapHouse 5 months ago

Mistress Alexa's Sissy Academy

61% HD 1:01 / 8:17

Mistress Alexa's Sissy Academy

FapHouse 6 months ago

I'm on vacation but my vagina works full time

I'm on vacation but my vagina works full time

xHamster 2 years ago

Paintedrose.live - Taboo Milf Rosie: Cuckold Training: Cuck Serve Fluff Chastity Eat Cum

Paintedrose.live - Taboo Milf Rosie: Cuckold Training: Cuck Serve Fluff Chastity Eat Cum

XMilf 3 years ago

How Would I Date My Femboy/sissy?

66% HD 0:39 / 9:32

How Would I Date My Femboy/sissy?

FapHouse 4 months ago

Playing with Pussy Having Fun

HD 2:00 / 19:33

Playing with Pussy Having Fun

Flirt4Free 12 years ago

Chastity Affirmations: Caged Cuckold 4K

4K 0:10 / 14:44

Chastity Affirmations: Caged Cuckold 4K

LoyalFans 3 years ago

Reprogrammed for Obedience

57% HD 0:39 / 7:55

Reprogrammed for Obedience

FapHouse 1 month ago

Panty Punishment

HD 1:01 / 32:21

Panty Punishment

FapHouse 1 week ago

Training Zero Rigid Chastity Cage Unboxing Model 20 & Model 10

Training Zero Rigid Chastity Cage Unboxing Model 20 & Model 10

xHamster 2 months ago

Isadora Dunkan Private Show

4K 2:00 / 11:41

Isadora Dunkan Private Show

Flirt4Free 3 days ago

Training Zero Femdom 8 Hours of Sensory Deprivation Bondage Cum Orgasm for my Slave Piss BDSM Homemade Real

Training Zero Femdom 8 Hours of Sensory Deprivation Bondage Cum Orgasm for my Slave Piss BDSM Homemade Real

xHamster 1 year ago

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