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Sissy Chastity (72,787)

Best of Harmony Rose volume 4

Best of Harmony Rose volume 4

xHamster 8 months ago

Cuckold 1 (prep Me for My Date!)

58% HD 1:01 / 6:34

Cuckold 1 (prep Me for My Date!)

FapHouse 10 months ago

Trans Chastity Fuck Doll - deep and rough anal fucking

Trans Chastity Fuck Doll - deep and rough anal fucking

xHamster 3 weeks ago

Sissy Step 5

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LoyalFans 1 year ago

White Sissy Virginity Instructing (Smash Machine)

White Sissy Virginity Instructing (Smash Machine)

TrannyGem 3 months ago

Facesitters in Heat Volume 1

Facesitters in Heat Volume 1

xHamster 3 years 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

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Torri Texass Private Show

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Flirt4Free 1 week ago

A horny brunette fucks her boyfriend with a strap on until he cums

A horny brunette fucks her boyfriend with a strap on until he cums

XCafe 2 years ago

Cuckold on the beach

Cuckold on the beach

xHamster 2 months ago

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Dafreeporn 9 months ago

Cuckold Fantasies Volume 24

Cuckold Fantasies Volume 24

xHamster 4 years ago

Autumn Woods Party on Jan 15, 2026 - Part 2

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Autumn Woods Party on Jan 15, 2026 - Part 2

Flirt4Free 3 weeks ago

Femdom Therapist's POV: Teasing in Chastity, How Many Days Are You Destined to Be in It?

Femdom Therapist's POV: Teasing in Chastity, How Many Days Are You Destined to Be in It?

xHamster 1 month ago

Chastity Femboy Pussy! Big Cock made into Tiny Pussy and Penetrated with Sounding Rod.

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Lesbian8 1 year ago

Isadora Dunkan Private Show

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Isadora Dunkan Private Show

Flirt4Free 5 days ago

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XGroovy 2 years ago

Who wants to drink my SPECIAL yogurt

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xHamster 11 months ago

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SortPorn 1 year ago

Tyna Doll Private Show

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Flirt4Free 3 days ago

Hot sissy in chastity is fucked by machine

Hot sissy in chastity is fucked by machine

xHamster 3 weeks ago

Roy & Hercules & Jamer Private Show

46% HD 2:00 / 6:07

Roy & Hercules & Jamer Private Show

Flirt4Free 3 years ago

BBC Cumming All Over Locked Caged Chastity Trans Slut Sammi Smith

BBC Cumming All Over Locked Caged Chastity Trans Slut Sammi Smith

aShemaleTube 3 months ago

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Chastity guide : A review of all metal chastity cages by sissy joyce

BigTitsLust 1 year ago

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Amateur8 9 months ago

Worshi My Legs and Ass in Pantyhose

61% 4K 2:00 / 2:59

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Flirt4Free 6 months ago

Viky & Mateo Private Show

62% HD 2:00 / 4:46

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Flirt4Free 3 weeks ago

First Anal Sissygasm

56% HD 0:39 / 9:36

First Anal Sissygasm

FapHouse 11 months ago

sexy redhead Domme pegs her cute caged sissy boyfriend

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LoyalFans 1 year ago

Roy & Hercules & Jamer Private Show

51% HD 2:00 / 4:09

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Flirt4Free 3 years ago

Femdom Mistresse Domina V humiliates & fully feminizes chastity cuckold sissy sub serf w/ sph 1/three

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FreePorn8 1 year ago

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

Master trains his sissy in Chastity. He uses her mouth and ass to her liking making her a real whore

xHamster 3 months ago

Rosie and Robin Oral Fun Pt 2

54% HD 0:39 / 9:32

Rosie and Robin Oral Fun Pt 2

FapHouse 5 months ago

How I became a bbc addict

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aShemaleTube 8 months ago

HOTTEST Crossdresser Bailey Wilde in Chastity Banged Reverse Cowgirl

HOTTEST Crossdresser Bailey Wilde in Chastity Banged Reverse Cowgirl

Tranny.one 3 months ago

Master's Mind Game, Part 2

HD 0:10 / 13:47

Master's Mind Game, Part 2

LoyalFans 3 weeks ago

Sissy College Lesson 2 Chastity

61% HD 1:01 / 5:37

Sissy College Lesson 2 Chastity

FapHouse 1 year ago

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FapHouse 1 month ago

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Genitalia haircut & edging for chastity slave

xHamster 11 months ago

Total Sissy Amnesia

Total Sissy Amnesia

xHamster 2 months ago

Jackie

aShemaleTube 7 months 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 2 months ago

Cuckold Fantasies Volume 24

Cuckold Fantasies Volume 24

PornFreeNow 10 months ago

Big ass tranny taking it like a pro and gets creampie

Big ass tranny taking it like a pro and gets creampie

xHamster 1 month ago

One of the best teases I've ever seen

One of the best teases I've ever seen

aShemaleTube 1 month ago

Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

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xHamster 3 years ago

Skater Boy to Sissy Slut Transformation! with Ruby Onyx

49% HD 0:10 / 12:47

Skater Boy to Sissy Slut Transformation! with Ruby Onyx

LoyalFans 3 years ago

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

xHamster 2 months ago

Sissy Academy Part 1

Sissy Academy Part 1

xHamster 4 months ago

Cuckolded hubby locked away, a final handjob farewell

Cuckolded hubby locked away, a final handjob farewell

Jizzberry 2 years ago

Rosie and Robin Oral Fun Pt1

60% HD 0:39 / 10:02

Rosie and Robin Oral Fun Pt1

FapHouse 5 months ago

Hot Pegging Fat Ass Domme and Submissive Sissy Femboy in Chastity

Hot Pegging Fat Ass Domme and Submissive Sissy Femboy in Chastity

xHamster 1 year ago

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Snowbunny Slave Halloween Costume

xHamster 3 months ago

BBC6

aShemaleTube 9 months ago

Prissy sissy Dolly - Locked in frills

58% HD 0:10 / 13:13

Prissy sissy Dolly - Locked in frills

LoyalFans 6 months ago

Locked, Submissive Trans Sissy in Long Machine Play

Locked, Submissive Trans Sissy in Long Machine Play

xHamster 2 months ago

My BF Was Late to Cum Fuck Me

65% HD 0:08 / 1:02

My BF Was Late to Cum Fuck Me

FapHouse 5 months ago

Rachael Belle Justice

Rachael Belle Justice

aShemaleTube 8 months ago

Best of Harmony Rose Volume 1

Best of Harmony Rose Volume 1

xHamster 3 years ago

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

Lingerie Sissy Gets Locked Onto Her Dildo Pole and Tries to Cum in Chastity

xHamster 3 weeks ago

Bbc Vs Chastity Sissy

Bbc Vs Chastity Sissy

getTranny 1 week ago

Best of Harmony Rose vol 2

Best of Harmony Rose vol 2

xHamster 10 months ago

Cuckold Fantasies volume 23

Cuckold Fantasies volume 23

xHamster 1 year ago

Filthy Blonde MILF Psychologist Cucks Her Sissy Patient Fucking With a Big Black Guy In Front Of Him

Filthy Blonde MILF Psychologist Cucks Her Sissy Patient Fucking With a Big Black Guy In Front Of Him

AnySex 1 year ago

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

Sissygasm Training: My Cockhungry Femboi Learns to Serve and Suffer

LoyalFans 2 months ago

Sissy Hero - PMV by HoloPMV

Sissy Hero - PMV by HoloPMV

aShemaleTube 6 months ago

Sissy Maid Sissygasms, Sissy Onyx

Sissy Maid Sissygasms, Sissy Onyx

aShemaleTube 3 years ago

Best of Harmony Rose volume 5

Best of Harmony Rose volume 5

xHamster 8 months ago

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Cuckold creampie eating hot wife fucking big cock lovers while sissy husband watches and eats cum

PornFreeNow 9 months ago

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xHamster 3 weeks ago

Sissy Bride in Chastity

Sissy Bride in Chastity

xHamster 1 month ago

Autumn Woods Party on Jan 11, 2026 - Part 5

69% HD 2:00 / 24:01

Autumn Woods Party on Jan 11, 2026 - Part 5

Flirt4Free 3 weeks ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 5

xHamster 1 month ago

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LoyalFans 1 year ago

Zara Rousse Private Show

4K 2:00 / 40:23

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Flirt4Free 1 week ago

Mastix Victoria Rey Collars, gags, humiliates, spits on her sexy chastity sissy thrall spouse. SPH loser Chastity Pt 1 of 5

Mastix Victoria Rey Collars, gags, humiliates, spits on her sexy chastity sissy thrall spouse. SPH loser Chastity Pt 1 of 5

MatureTubeHere 1 year ago

Viky & Mateo Private Show

64% HD 2:00 / 4:35

Viky & Mateo Private Show

Flirt4Free 4 weeks ago

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

46% HD 1:01 / 19:18

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

FapHouse 1 month ago

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Latex Sissy Anal Chastity Discipline by Mistresse Mercer

Latex Sissy Anal Chastity Discipline by Mistresse Mercer

Amateur8 1 month ago

Size Matters

HD 0:10 / 13:00

LoyalFans 1 week ago

elf femboy in chastity belt gets tight ass stretched by bbc cock and fuck machine until cum

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Lesbian8 11 months ago

I Feminize You into a Sissy and Teach You to Suck Cock: Immersive POV - Mistress Julia

I Feminize You into a Sissy and Teach You to Suck Cock: Immersive POV - Mistress Julia

PornFreeNow 7 months ago

Ultimate Chastity Moments with Your Dominant Girlfriend - A Femdom Experience

Ultimate Chastity Moments with Your Dominant Girlfriend - A Femdom Experience

MoanTube 2 weeks ago

Worship and Cum on my boots just before i Go to see my Lover : Mistress Julia Vid111

Worship and Cum on my boots just before i Go to see my Lover : Mistress Julia Vid111

Pornzona 1 month ago

Cuckold Fantasies Volume 24

Cuckold Fantasies Volume 24

Lesbian8 10 months ago

Rachael Belle _ Kenny Kumshot - Locktober Prepped

Rachael Belle _ Kenny Kumshot - Locktober Prepped

aShemaleTube 8 months 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

The Vice Mach 2 chastity cage (prototype) product review!!

The Vice Mach 2 chastity cage (prototype) product review!!

xHamster 3 months ago

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

48% HD 0:10 / 26:27

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

LoyalFans 3 months ago

Fucking Sexy Sissy in Chastity - Compilation 2

Fucking Sexy Sissy in Chastity - Compilation 2

xHamster 1 month ago

Te Transform in Tarfa Mea

Premium HD 9:58

Te Transform in Tarfa Mea

XVideosRed 9 months ago

Sissy Wife Pegged In Chastity - Clara Dee POV

Sissy Wife Pegged In Chastity - Clara Dee POV

xHamster 2 years ago

Chastity, Locked! (absolute Power 2)

67% HD 0:39 / 9:10

Chastity, Locked! (absolute Power 2)

FapHouse 8 months ago

Worship My Nylon Feet

60% 4K 2:00 / 2:04

Worship My Nylon Feet

Flirt4Free 6 months ago

Sophia Loreen Party on May 24, 2025 - Part 2

65% 4K 2:00 / 25:52

Sophia Loreen Party on May 24, 2025 - Part 2

Flirt4Free 8 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 6 months ago

My first time with a BBC 🥵

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aShemaleTube 2 years ago

Breaking Her Sissy Doll Part 4/4: Anal Training with Fuck Machine, Huge Cock & Cum Eating with Mistress Stellina Obscura

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LoyalFans 6 months ago

Fucking of a Lifetime - Variety Itsol

Fucking of a Lifetime - Variety Itsol

BallsAndBoobs 1 year ago

A sissy fetish for high heels

A sissy fetish for high heels

xHamster 2 months ago

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

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

xHamster 1 month ago

Cuckold Dreams Volume 24

Cuckold Dreams Volume 24

FreePorn8 1 year ago

Sissy husbands

Amateur8 4 years ago

*SISSYGASM* Couldn't stop fucking myself

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LoyalFans 1 year ago

Cum in Your Panties

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xHamster 2 months ago

Cunilingus and analingus on the beach. My husband is a sissy.

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xHamster 9 months ago

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

Chatty Crossdresser chats again... and tries new plug 2023-02-26 part 1

xHamster 2 years ago

Humiliation on the beach

Humiliation on the beach

xHamster 9 months ago

Virgin Sissified & Pegged

61% HD 0:10 / 12:38

Virgin Sissified & Pegged

LoyalFans 2 years ago

Sophia Loreen Party on Oct 23, 2025 - Part 2

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Sophia Loreen Party on Oct 23, 2025 - Part 2

Flirt4Free 3 months ago

Sophia Loreen Private Show

57% 4K 2:00 / 5:19

Sophia Loreen Private Show

Flirt4Free 5 months ago

SiSSY COCK SUCKER | Veronica Vixen

65% HD 0:10 / 10:03

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LoyalFans 2 years ago

Sissy Dream

Xfeed 2 years ago

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

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xHamster 1 year ago

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