Chastity Sissy (48,974)

Katharine Cane Party on Jul 6, 2026 - Part 2

58% 4K 2:00 / 6:32

Katharine Cane Party on Jul 6, 2026 - Part 2

Camster 2 weeks ago

Chloe Riveiro Private Show

4K 2:00 / 1:02:26

Chloe Riveiro Private Show

Flirt4Free 1 week ago

Fia & Mia Private Show

64% HD 2:00 / 14:07

Fia & Mia Private Show

Flirt4Free 3 years ago

1st TIME PEGGING ON A SWING

64% HD 0:28 / 8:20

1st TIME PEGGING ON A SWING

Clips4sale 3 years ago

Chaste Sissy Slut One Bar Prison Tease

69% HD 0:10 / 13:25

Chaste Sissy Slut One Bar Prison Tease

LoyalFans 3 years ago

Rush

65% HD 0:25 / 17:18

IWantClips 3 years ago

Edging and Sounding by Dominafire

60% 0:39 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years 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

Sissy Husband Becomes Cocksucking Cuckold

54% HD 0:10 / 16:13

Sissy Husband Becomes Cocksucking Cuckold

LoyalFans 4 months ago

Chastity, Locked! (absolute Power 2)

69% 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

64% 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

51% HD 1:01 / 19:18

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

FapHouse 7 months ago

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

54% HD 0:39 / 12:35

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

FapHouse 5 months ago

Grisha Mochka Private Show

66% 4K 2:00 / 19:56

Grisha Mochka Private Show

Camster 3 weeks ago

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

50% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 8 months ago

Fun Feminization

53% HD 0:10 / 5:34

Fun Feminization

LoyalFans 1 year ago

Edging and Sounding by Dominafire

61% 1:01 / 24:43

Edging and Sounding by Dominafire

FapHouse 2 years ago

Dressing up Sissy

55% HD 0:39 / 10:15

Dressing up Sissy

FapHouse 1 year ago

Sissy Training in Chastity

56% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Home From the Wedding, Foot Cuck!

72% HD 1:01 / 16:14

Home From the Wedding, Foot Cuck!

FapHouse 1 year 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

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

Size Queen Sissy Boy Training with CEI

HD 0:39 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 2 weeks ago

Khloe Clark Private Show

48% 4K 2:00 / 24:07

Khloe Clark Private Show

Camster 1 month 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

Bi Domination: Not Entirely Straight

55% HD 1:01 / 21:14

Bi Domination: Not Entirely Straight

FapHouse 2 months ago

Viky & Mateo Private Show

58% HD 2:00 / 11:13

Viky & Mateo Private Show

Flirt4Free 6 months ago

Size Queen Sissy Boy Training with CEI

69% HD 1:01 / 20:55

Size Queen Sissy Boy Training with CEI

FapHouse 2 weeks ago

Chaste sissy

55% HD 1:01 / 25:28

FapHouse 6 years ago

Sissy Extreme Chastity Tease

53% HD 0:10 / 9:23

Sissy Extreme Chastity Tease

LoyalFans 3 months ago

Adara Smith & Elver Rodriguez Private Show

60% HD 2:00 / 8:21

Adara Smith & Elver Rodriguez Private Show

Camster 2 years ago

Bossy and Ruthless Mistress Gives Her Feminized Husband a Humiliating Handjob - Mistress Julia

Bossy and Ruthless Mistress Gives Her Feminized Husband a Humiliating Handjob - Mistress Julia

FapHouse 3 weeks 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

Borrow My Sissy Boyfriend

51% 1:01 / 25:50

Borrow My Sissy Boyfriend

FapHouse 6 months 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

Creampie and Chastity

Creampie and Chastity

FapHouse 3 weeks ago

Rubber Sissy Fuck Machine Pegging

64% HD 0:10 / 14:05

Rubber Sissy Fuck Machine Pegging

LoyalFans 2 months ago

Home From the Wedding, Foot Cuck!

63% HD 0:39 / 16:14

Home From the Wedding, Foot Cuck!

FapHouse 1 year 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 2 weeks ago

Borrow My Sissy Boyfriend

60% 0:39 / 25:50

Borrow My Sissy Boyfriend

FapHouse 6 months ago

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

49% HD 0:10 / 26:27

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

LoyalFans 9 months ago

Part 1 Locked and Conditioned for This Sissy After 6 Months with No News - Maitresse Julia

56% HD 1:01 / 15:43

Part 1 Locked and Conditioned for This Sissy After 6 Months with No News - Maitresse Julia

FapHouse 2 years ago

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

59% 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 3 weeks ago

Sissy College Lesson 2 Chastity

53% HD 0:08 / 0:40

Sissy College Lesson 2 Chastity

FapHouse 9 months ago

Sweet & Daaniel Private Show

64% HD 2:00 / 14:05

Sweet & Daaniel Private Show

Camster 1 month ago

Boy to Girl - Permanent Transformation

46% HD 1:01 / 8:47

Boy to Girl - Permanent Transformation

FapHouse 2 years ago

Viky & Mateo Private Show

52% HD 2:00 / 32:44

Viky & Mateo Private Show

Camster 6 months ago

Chaste Sissy Slut One Bar Prison Tease

63% HD 0:10 / 13:25

Chaste Sissy Slut One Bar Prison Tease

LoyalFans 3 years 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

Chaste & Sissified

45% HD 0:10 / 7:19

Chaste & Sissified

LoyalFans 1 month ago

Femdom POV Sissy Training Pleasure Him

51% HD 1:01 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months 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

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

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 5 days ago

Sissy Cum in Chastity - Suspended by Hook

57% HD 1:01 / 7:21

Sissy Cum in Chastity - Suspended by Hook

FapHouse 3 weeks 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

Petite Ma'am fucking her pink sissy maid in chastity

Petite Ma'am fucking her pink sissy maid in chastity

XHamster 3 years ago

🌺 Sissy Training - Learn to suck dick! 🌺

66% HD 0:10 / 7:33

🌺 Sissy Training - Learn to suck dick! 🌺

LoyalFans 9 months ago

Brittney & Elvis Private Show

67% HD 2:00 / 6:22

Brittney & Elvis Private Show

Camster 2 years ago

1st Sissy Experience With Miss Shell

54% HD 0:10 / 23:00

1st Sissy Experience With Miss Shell

LoyalFans 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

Sissy Molly serving Mistress Susi in Chastity / Sissy Molly Stiefeldienst in Chastity

57% HD 0:10 / 16:13

Sissy Molly serving Mistress Susi in Chastity / Sissy Molly Stiefeldienst in Chastity

LoyalFans 3 years ago

Making My Husband into a Cuckold Sissy!

49% 0:11 / 9:49

Making My Husband into a Cuckold Sissy!

Clips4sale 2 years ago

Can You Cum, Sissy? * Custom) 4K

61% 4K 0:08 / 0:40

Can You Cum, Sissy? * Custom) 4K

FapHouse 1 month ago

Goddess Worship in Bed!

HD 0:39 / 18:27

Goddess Worship in Bed!

FapHouse 2 months ago

Naughty Maids

55% 0:30 / 16:41

Clips4sale 5 months 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

Inverted chastity cage

51% HD 0:10 / 8:28

Inverted chastity cage

LoyalFans 9 months ago

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

let\'s get naughty - Part 2

Camster 1 week ago

Sissy Maid gets Locked into Her Role (4K)

4K 0:10 / 10:29

Sissy Maid gets Locked into Her Role (4K)

LoyalFans 1 week ago

Rosies Sissification

59% HD 1:01 / 11:09

Rosies Sissification

FapHouse 1 year 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

Rileys Chastity House Boy

72% HD 1:01 / 10:47

Rileys Chastity House Boy

FapHouse 2 weeks ago

Total Transformation - HD

42% HD 0:10 / 5:28

Total Transformation - HD

LoyalFans 1 year ago

Get her ready for the Cage

55% HD 1:01 / 11:40

Get her ready for the Cage

FapHouse 5 years ago

Femdom POV Sissy Training Pleasure Him

46% HD 0:39 / 22:52

Femdom POV Sissy Training Pleasure Him

FapHouse 3 months ago

Anal Sissy Slut in Chastity

58% HD 0:10 / 15:25

Anal Sissy Slut in Chastity

LoyalFans 4 months ago

Submissive Bunny Fucked and Pissed on by 2 Dominas

HD 1:01 / 13:43

Submissive Bunny Fucked and Pissed on by 2 Dominas

FapHouse 1 week ago

My Fuck Toy

66% HD 0:10 / 9:52

LoyalFans 2 years ago

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

58% 1:00 / 10:40

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

Clips4sale 4 months ago

Sissy Cum Sisters

60% HD 0:10 / 23:23

Sissy Cum Sisters

LoyalFans 1 month ago

Ruined twice after uncaged from chastity!

58% HD 0:39 / 15:12

Ruined twice after uncaged from chastity!

FapHouse 6 years ago

Teasing My Toy Thing in Chastity! - Tease and Denial with Pantyhose Domination, Chastity and Orgasm Denial with Miss Adrastea

62% HD 1:01 / 17:40

Teasing My Toy Thing in Chastity! - Tease and Denial with Pantyhose Domination, Chastity and Orgasm Denial with Miss Adrastea

FapHouse 1 month ago

Cucks duties before and after date

63% HD 1:01 / 27:35

Cucks duties before and after date

FapHouse 3 years ago

Dominafire pov pegging her chastity sissy

Dominafire pov pegging her chastity sissy

XHamster 3 years ago

Frustrated Sissy Plugged and in Chastity

Frustrated Sissy Plugged and in Chastity

PornFreeNow 1 month ago

Viky & Mateo Private Show

56% HD 2:00 / 32:44

Viky & Mateo Private Show

Flirt4Free 6 months ago

Worshiping divine GODDESS FEET

65% HD 0:19 / 12:37

Worshiping divine GODDESS FEET

Clips4sale 3 months ago

I'll Stop When You Drop

HD 0:10 / 13:48

I'll Stop When You Drop

LoyalFans 4 days ago

Cuckold Sissy Maid in Training (4K)

65% 4K 0:13 / 10:36

Cuckold Sissy Maid in Training (4K)

Clips4sale 2 months ago

Brittney & Elvis Private Show

56% HD 2:00 / 6:22

Brittney & Elvis Private Show

Flirt4Free 2 years ago

Viky & Mateo Private Show

62% HD 2:00 / 19:22

Viky & Mateo Private Show

Flirt4Free 6 months ago

Milking the Sissy

52% HD 0:39 / 11:14

Milking the Sissy

FapHouse 4 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

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

HD 0:10 / 16:00

Mistress Baton’s Sissy Finishing School Part 3 - Spitroasting

LoyalFans 3 weeks ago

Bimbo rubber doll - Chastity and dick sucking

65% 0:30 / 9:47

Bimbo rubber doll - Chastity and dick sucking

Clips4sale 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 3 years ago

Encouraged Bi Sissy Cuckold Full Video

65% HD 0:10 / 21:42

Encouraged Bi Sissy Cuckold Full Video

LoyalFans 1 week ago

Pegging bimbo slut | Evilwoman

HD 0:10 / 13:02

Pegging bimbo slut | Evilwoman

LoyalFans 2 months ago

Strap-on Pegging surprise: Matriarch Ezada Sinn fucks sissy maid during chores

Strap-on Pegging surprise: Matriarch Ezada Sinn fucks sissy maid during chores

IWantClips 1 month ago

Can You Cum, Sissy? * Custom) 4K

4K 1:01 / 11:35

Can You Cum, Sissy? * Custom) 4K

FapHouse 1 month ago

Teaching My Caged Passenger a Lesson

59% HD 1:01 / 26:34

Teaching My Caged Passenger a Lesson

FapHouse 4 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 1 month 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

BG redhead latex domme fists sissy for the first time pt 1 - full video on Veggiebabyy Manyvids

BG redhead latex domme fists sissy for the first time pt 1 - full video on Veggiebabyy Manyvids

XHamster 2 years ago

The Milked Fleshlight Sissy Whore

55% 1:01 / 11:13

The Milked Fleshlight Sissy Whore

FapHouse 1 month ago

My New Office Sissy

61% HD 0:10 / 16:55

My New Office Sissy

LoyalFans 1 year ago

Viky & Mateo Private Show

66% HD 2:00 / 4:48

Viky & Mateo Private Show

Camster 6 months ago

Locked up and Dressed up for Worship

Locked up and Dressed up for Worship

FapHouse 2 days 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 2 weeks ago

Giant Creampie Eating Gulp Compilation Large Cum Eating Cuckolds Bitch Wife Screwing And Sucking Bbc Coarse Sex chastity ding-dong

Giant Creampie Eating Gulp Compilation Large Cum Eating Cuckolds Bitch Wife Screwing And Sucking Bbc Coarse Sex chastity ding-dong

Amateur8 3 years ago

Turning You Into Sissy- Russian Edition

48% HD 0:39 / 4:38

Turning You Into Sissy- Russian Edition

FapHouse 1 month ago

Compilation of make me bi, feminization, anal sex BBC and sissy in chastity all the time

73% 0:53 / 42:33

Compilation of make me bi, feminization, anal sex BBC and sissy in chastity all the time

Clips4sale 1 year 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

Bossy and Ruthless Mistress Gives Her Feminized Husband a Humiliating Handjob - Mistress Julia

Bossy and Ruthless Mistress Gives Her Feminized Husband a Humiliating Handjob - Mistress Julia

XHamster 3 weeks ago

Play Time Pt.2

60% HD 0:10 / 9:48

LoyalFans 1 month ago

Lucy Cucks Sissy with Bully

58% HD 0:10 / 21:05

Lucy Cucks Sissy with Bully

LoyalFans 5 months ago

Caged Pervert Caught Spying & Punished

67% HD 0:10 / 7:56

Caged Pervert Caught Spying & Punished

LoyalFans 1 year ago

Pussy Eating Sissy (with CEI)

63% HD 0:39 / 10:01

Pussy Eating Sissy (with CEI)

FapHouse 1 year ago

Chloe Riveiro Private Show

4K 2:00 / 2:09:22

Chloe Riveiro Private Show

Camster 3 days ago

Mia Califa Private Show

Mia Califa Private Show

Camster 4 days ago

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