Sissy Chastity (48,738)

Nazanin Hunter Private Show

52% HD 2:00 / 19:16

Nazanin Hunter Private Show

Flirt4Free 2 years ago

1st TIME PEGGING ON A SWING

64% HD 0:28 / 8:20

1st TIME PEGGING ON A SWING

Clips4sale 3 years ago

Rush

65% HD 0:25 / 17:18

IWantClips 3 years ago

Maid to Suck

66% HD 0:07 / 0:40

FapHouse 2 weeks ago

Chaste & Sissified

45% HD 0:10 / 7:19

Chaste & Sissified

LoyalFans 2 months ago

New Sissy in Training (4K)

53% 4K 0:18 / 11:44

New Sissy in Training (4K)

Clips4sale 5 months ago

Sissy Husband Becomes Cocksucking Cuckold

55% HD 0:10 / 16:13

Sissy Husband Becomes Cocksucking Cuckold

LoyalFans 4 months ago

Cuckold 1 Prep Me for My Date!

58% HD 1:01 / 6:34

Cuckold 1 Prep Me for My Date!

FapHouse 1 year ago

Chastity, Locked! (absolute Power 2)

70% HD 1:01 / 9:10

Chastity, Locked! (absolute Power 2)

FapHouse 1 year ago

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

70% HD 1:01 / 11:28

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

FapHouse 1 month 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 7 months ago

Edging and Sounding by Dominafire

60% 1:01 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

Bi Domination: Not Entirely Straight

58% HD 1:01 / 21:14

Bi Domination: Not Entirely Straight

FapHouse 3 months ago

Fun Feminization

53% HD 0:10 / 5:34

Fun Feminization

LoyalFans 1 year 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 8 months ago

Sissy Training in Chastity

57% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Grisha Mochka Private Show

64% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 1 month ago

Borrow My Sissy Boyfriend

52% 1:01 / 25:50

Borrow My Sissy Boyfriend

FapHouse 6 months ago

You were born to be my slave! (WORSHIP ME)

HD 0:30 / 11:44

You were born to be my slave! (WORSHIP ME)

Clips4sale 1 week ago

Girls Night In: Dressing My Sissy Up & Talking About Boys

52% HD 0:10 / 6:13

Girls Night In: Dressing My Sissy Up & Talking About Boys

LoyalFans 2 months ago

Size Queen Sissy Boy Training with CEI

HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 3 weeks 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 5 months ago

Chaste sissy

56% HD 1:01 / 25:28

FapHouse 6 years ago

Home From the Wedding, Foot Cuck!

72% HD 1:01 / 16:14

Home From the Wedding, Foot Cuck!

FapHouse 1 year ago

Adara Smith & Elver Rodriguez Private Show

69% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Camster 2 years ago

Sissy Extreme Chastity Tease

53% HD 0:10 / 9:23

Sissy Extreme Chastity Tease

LoyalFans 4 months ago

Chaste Sissy Slut One Bar Prison Tease

62% HD 0:10 / 13:25

Chaste Sissy Slut One Bar Prison Tease

LoyalFans 3 years ago

Made over and fucked like a dirty whore

59% HD 1:01 / 13:47

Made over and fucked like a dirty whore

FapHouse 3 years ago

Size Queen Sissy Boy Training with CEI

69% HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 3 weeks ago

Borrow My Sissy Boyfriend

62% 0:39 / 25:50

Borrow My Sissy Boyfriend

FapHouse 6 months ago

Viky & Mateo Private Show

46% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 6 months ago

Viky & Mateo Private Show

57% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 6 months ago

Strap-on fucking and latex sissy training: a day in the life of a Matriarch Ezada Sinn’s sissy husband

63% HD 0:10 / 15:10

Strap-on fucking and latex sissy training: a day in the life of a Matriarch Ezada Sinn’s sissy husband

LoyalFans 1 week ago

2 Lesbians Taunt a Submissive Man and Fuck in Front of Him

HD 0:39 / 22:03

2 Lesbians Taunt a Submissive Man and Fuck in Front of Him

FapHouse 2 days ago

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

74% HD 1:01 / 13:19

Episode 2: Part 1: a Transformed Life: New Sissy Sexuality - Maitresse Julia

FapHouse 1 year ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Total Transformation - HD

42% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 1 year 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 1 month ago

Get her ready for the Cage

55% HD 1:01 / 11:40

Get her ready for the Cage

FapHouse 5 years ago

Sweet & Daaniel Private Show

64% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 1 month ago

The Milked Fleshlight Sissy Whore

51% 0:39 / 11:13

The Milked Fleshlight Sissy Whore

FapHouse 2 months ago

Cock Casting 3 - Slut Sacking

Cock Casting 3 - Slut Sacking

FapHouse 1 day ago

Femdom POV Sissy Training Pleasure Him

52% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Part 2 My Husband Sissified: a Female Latex Slave Doll Pegged - Mistress Julia

74% HD 1:01 / 7:52

Part 2 My Husband Sissified: a Female Latex Slave Doll Pegged - Mistress Julia

FapHouse 10 months ago

Creampie and Chastity

Creampie and Chastity

FapHouse 4 weeks ago

Chaste Sissy Slut One Bar Prison Tease

70% HD 0:10 / 13:25

Chaste Sissy Slut One Bar Prison Tease

LoyalFans 3 years ago

Sissy College Lesson 2 Chastity

53% HD 0:08 / 0:40

Sissy College Lesson 2 Chastity

FapHouse 9 months ago

Look, This Is How You Will Feel Soon When I Locked You up! - Chastity Tease with Orgasm Denial and Pantyhose Domination

58% HD 1:01 / 16:31

Look, This Is How You Will Feel Soon When I Locked You up! - Chastity Tease with Orgasm Denial and Pantyhose Domination

FapHouse 3 months ago

Caged Teasing Plus Uncaging and Ruined with Magic Wand

63% 1:01 / 22:31

Caged Teasing Plus Uncaging and Ruined with Magic Wand

FapHouse 1 month ago

Brittney & Elvis Private Show

60% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 3 years ago

Fucking You in Chasity

HD 1:01 / 10:26

Fucking You in Chasity

FapHouse 2 months ago

Edging and Sounding by Dominafire

60% 0:39 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

Femdom POV Sissy Training Pleasure Him

46% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

Tinder date becomes a toilet slave (edited version)

66% HD 0:39 / 26:55

Tinder date becomes a toilet slave (edited version)

FapHouse 5 years ago

Out of chastity to cum on my nylons

56% HD 1:01 / 8:31

Out of chastity to cum on my nylons

FapHouse 7 years ago

Turning You Into Sissy- Russian Edition

48% HD 0:39 / 4:38

Turning You Into Sissy- Russian Edition

FapHouse 1 month ago

You Stay Locked up and Cum in Chastity! - Cum in Chastity with Tease and Denial and Pantyhose Domination with Miss Adrastea

62% HD 1:01 / 15:47

You Stay Locked up and Cum in Chastity! - Cum in Chastity with Tease and Denial and Pantyhose Domination with Miss Adrastea

FapHouse 1 month ago

Viky & Mateo Private Show

54% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 6 months ago

Peggin Thee Stallion & Miss Oyuki: Man! I Feel Like a Femboy!

50% HD 0:10 / 14:43

Peggin Thee Stallion & Miss Oyuki: Man! I Feel Like a Femboy!

LoyalFans 5 months ago

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

59% HD 0:39 / 16:47

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

FapHouse 3 weeks ago

Girls Night In: Dressing My Sissy Up & Talking About Boys

65% HD 0:29 / 6:13

Girls Night In: Dressing My Sissy Up & Talking About Boys

IWantClips 1 month ago

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

HD 1:01 / 16:47

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

FapHouse 3 weeks ago

You are not a man! – Destroying the Cuckold Part 2

47% HD 0:10 / 26:27

You are not a man! – Destroying the Cuckold Part 2

LoyalFans 9 months ago

Cuckold 1 Prep Me for My Date!

47% HD 0:39 / 6:34

Cuckold 1 Prep Me for My Date!

FapHouse 1 year ago

Rileys Chastity House Boy

73% HD 1:01 / 10:47

Rileys Chastity House Boy

FapHouse 3 weeks ago

Anal Sissy Slut in Chastity

58% HD 0:10 / 15:25

Anal Sissy Slut in Chastity

LoyalFans 4 months ago

Sissy Strapon Fucked by Dominafire

Sissy Strapon Fucked by Dominafire

FapHouse 1 year ago

Fucking the Sissy We Found in Bed

60% HD 1:01 / 7:21

Fucking the Sissy We Found in Bed

FapHouse 1 year ago

Viky & Mateo Private Show

69% HD 2:00 / 4:48

Viky & Mateo Private Show

Camster 6 months ago

Play Time Pt.2

55% HD 0:10 / 9:48

LoyalFans 2 months ago

Katharine Cane Party on Jul 6, 2026 - Part 2

51% 4K 2:00 / 6:32

Katharine Cane Party on Jul 6, 2026 - Part 2

Camster 3 weeks ago

Teaching My Caged Passenger a Lesson

59% HD 1:01 / 26:34

Teaching My Caged Passenger a Lesson

FapHouse 4 months ago

The vice chastity cage for my sissy slut

59% HD 0:39 / 6:30

The vice chastity cage for my sissy slut

FapHouse 7 years ago

Control his piss and let's him funny masturbate

52% 1:01 / 12:58

Control his piss and let's him funny masturbate

FapHouse 3 years ago

Inverted chastity cage

48% HD 0:10 / 8:28

Inverted chastity cage

LoyalFans 9 months ago

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

54% HD 0:10 / 2:40:24

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

LoyalFans 5 months ago

1st Sissy Experience With Miss Shell

54% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 3 months ago

BG Chastity & Harsh Pegging Orgasm Denial

66% HD 0:10 / 17:15

BG Chastity & Harsh Pegging Orgasm Denial

LoyalFans 1 month ago

Chastity, Locked! (absolute Power 2)

61% HD 0:39 / 9:10

Chastity, Locked! (absolute Power 2)

FapHouse 1 year ago

Naughty Maids

52% 0:30 / 16:41

Clips4sale 5 months ago

Rosies Sissification

59% HD 1:01 / 11:09

Rosies Sissification

FapHouse 1 year ago

Sissy Maid gets Locked into Her Role (4K)

63% 4K 0:10 / 10:29

Sissy Maid gets Locked into Her Role (4K)

LoyalFans 2 weeks ago

Pegging Session with My Chastity Slave

65% HD 1:01 / 10:45

Pegging Session with My Chastity Slave

FapHouse 3 years ago

Submissive Slut Gets Strapon Gangbanged!

65% 1:01 / 7:26

Submissive Slut Gets Strapon Gangbanged!

FapHouse 1 month ago

Lady Caitlyn Party on Jun 30, 2026

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

Lady Caitlyn Party on Jun 30, 2026

Camster 4 weeks ago

🌺 Sissy Training - Learn to suck dick! 🌺

66% HD 0:10 / 7:33

🌺 Sissy Training - Learn to suck dick! 🌺

LoyalFans 10 months ago

Two Sissies Captured for Lady Sara Borgia's Sissy School (4K)

4K 0:10 / 11:26

Two Sissies Captured for Lady Sara Borgia's Sissy School (4K)

LoyalFans 2 weeks ago

Tied Gagged and Pegged by Latex Mistress

62% HD 0:10 / 20:35

Tied Gagged and Pegged by Latex Mistress

LoyalFans 3 years ago

Complete Shrink & Hole Discipline Ritual - Full Femdom POV Session

Complete Shrink & Hole Discipline Ritual - Full Femdom POV Session

XHamster 4 months ago

Sissy Huren Ausbildung Incl Sperma schlucken (deutsch) /Sissy Hure Training, including to swallow sperm (german)

54% HD 0:10 / 13:14

Sissy Huren Ausbildung Incl Sperma schlucken (deutsch) /Sissy Hure Training, including to swallow sperm (german)

LoyalFans 3 years ago

Rubber Sissy Fuck Machine Pegging

64% HD 0:10 / 14:05

Rubber Sissy Fuck Machine Pegging

LoyalFans 2 months ago

Ares & Adara Private Show

54% HD 2:00 / 9:20

Ares & Adara Private Show

Flirt4Free 1 year ago

Released For Removal: Latex Chastity Entrapment Femdom POV Removal Fantasy - Miss Roper

63% 4K 0:26 / 10:14

Released For Removal: Latex Chastity Entrapment Femdom POV Removal Fantasy - Miss Roper

Clips4sale 4 days ago

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

let\'s cum together - Part 5

Camster 4 days ago

Manu Eyngri Private Show

Manu Eyngri Private Show

Camster 1 week ago

BG hot latex chastity couple femdom edging handjob - HD

65% HD 0:30 / 9:22

BG hot latex chastity couple femdom edging handjob - HD

Clips4sale 2 years ago

Sissy Training in Chastity

67% HD 1:01 / 9:54

Sissy Training in Chastity

FapHouse 1 year 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

Worshiping divine GODDESS FEET

65% HD 0:19 / 12:37

Worshiping divine GODDESS FEET

Clips4sale 3 months ago

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

let\'s get naughty - Part 2

Camster 2 weeks ago

Sissy Cum Sisters

58% HD 0:10 / 23:23

Sissy Cum Sisters

LoyalFans 1 month ago

Petite Ma'am fucking her pink sissy maid in chastity

Petite Ma'am fucking her pink sissy maid in chastity

XHamster 3 years ago

Humiliating our sissy

77% 0:29 / 9:15

Humiliating our sissy

Clips4sale 2 years ago

Making of Sissy Sasha

63% HD 0:25 / 33:34

Making of Sissy Sasha

IWantClips 1 month ago

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

HD 0:10 / 16:00

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

LoyalFans 4 weeks ago

Reluctant Sissy Maid In Chastity Submits to Femdom

57% HD 0:10 / 14:23

Reluctant Sissy Maid In Chastity Submits to Femdom

LoyalFans 1 year ago

Brittney & Elvis Private Show

56% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 3 years ago

Chastity & Silk: Guided Sissy Transformation. Mistress Damazonia x Domina Ava Savage Part 2 of 4

54% HD 0:10 / 15:42

Chastity & Silk: Guided Sissy Transformation. Mistress Damazonia x Domina Ava Savage Part 2 of 4

LoyalFans 7 months ago

Programmed to be my rubber slut doll

64% 4K 0:11 / 27:28

Programmed to be my rubber slut doll

Clips4sale 2 years ago

Footjobs in nylon

65% HD 1:01 / 7:56

Footjobs in nylon

FapHouse 7 years ago

Chastity Sissy Tease & Denial in CBT Bondage

59% HD 0:10 / 7:36

Chastity Sissy Tease & Denial in CBT Bondage

LoyalFans 6 months ago

Strap-on pegging for your first day as my sissy POV | Evilwoman

63% HD 0:10 / 10:15

Strap-on pegging for your first day as my sissy POV | Evilwoman

LoyalFans 3 months ago

Red Lips Tease and Pussyplay

61% 4K 2:00 / 10:06

Red Lips Tease and Pussyplay

Flirt4Free 3 years ago

Goddess Worship in Bed!

HD 0:39 / 18:27

Goddess Worship in Bed!

FapHouse 2 months ago

Chastity Training Starts w Pegging

Chastity Training Starts w Pegging

LoyalFans 2 months ago

Sissy Jenna First Lesson

60% HD 1:01 / 17:38

Sissy Jenna First Lesson

FapHouse 2 years ago

Manu Eyngri Private Show

4K 2:00 / 28:43

Manu Eyngri Private Show

Camster 2 weeks ago

My Sissy Rebel. Solution: Humiliation, Dehumanization, CBT in Boots - Mistress Julia

HD 0:10 / 16:15

My Sissy Rebel. Solution: Humiliation, Dehumanization, CBT in Boots - Mistress Julia

LoyalFans 1 month ago

Femdom Pegging Gangbang

51% 0:39 / 11:17

Femdom Pegging Gangbang

FapHouse 5 months ago

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