Chastity Videos - Trans (38,525)

BBC6

aShemaleTube 1 week ago

BBC4

aShemaleTube 1 week ago

Sissy Cuckold Fed Creampie and Cum Foot Worship - Jessica Bloom Ft Polieana

63% HD 0:39 / 9:26

Sissy Cuckold Fed Creampie and Cum Foot Worship - Jessica Bloom Ft Polieana

FapHouse 3 months ago

BBC5

aShemaleTube 1 week ago

Trans alternative breaths in the sissy transformation gas

Trans alternative breaths in the sissy transformation gas

ShemaleSin 2 weeks ago

Glazing Donuts

HD 0:29 / 32:49

Clips4sale 3 days ago

Mistress of the Night part II

70% 0:20 / 14:13

Mistress of the Night part II

Clips4sale 1 year ago

UNLEASH THE FURY Tattooed Shemale Teases with Chastity Belt Hell!

UNLEASH THE FURY Tattooed Shemale Teases with Chastity Belt Hell!

CrazyPorn 2 weeks ago

Daddy Fucks Cute Skinny Tgirl

Daddy Fucks Cute Skinny Tgirl

PornGem 2 days ago

Femboys Raine and Flare fucking in new apartment! (Teaser)

Femboys Raine and Flare fucking in new apartment! (Teaser)

SissyFlix 1 week ago

Shemale Slut Trains Her Throat

61% 0:10 / 6:49

Shemale Slut Trains Her Throat

Mistress starts a new PROSTATE ORGASM training (and seems to work)

Mistress starts a new PROSTATE ORGASM training (and seems to work)

Clips4sale 1 week ago

Good Girls Get Chastity From Femdom Elizabelle Dixie

HD 0:10 / 10:41

Good Girls Get Chastity From Femdom Elizabelle Dixie

LoyalFans 1 week ago

Chastity cage and Analplug

71% 0:14 / 3:48

Chastity cage and Analplug

Clips4sale 3 months ago

Woman In Rosy Innocence

Woman In Rosy Innocence

Transvids.tv 3 days ago

HOTTEST PORKING HEFTY STRAP DILDO SISSY RECTAL. THIS BIOTCH IS PREPPED TO DRILL. Sissy Nailed In Innocence

HOTTEST PORKING HEFTY STRAP DILDO SISSY RECTAL. THIS BIOTCH IS PREPPED TO DRILL. Sissy Nailed In Innocence

TrannyGem 1 week ago

Cute trap The Mortal Medusa in chastity

Cute trap The Mortal Medusa in chastity

aShemaleTube 6 years ago

Janie Blade: Butt Slut Left to Her Own Devices

59% HD 1:42 / 29:54

Janie Blade: Butt Slut Left to Her Own Devices

Kink 4 years ago

Cat Cafes New Hire

67% 4K 0:30 / 28:18

Cat Cafes New Hire

Clips4sale 1 year ago

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64% 0:13 / 7:16

trans in chastity extreme gape with inflateable butt plug

Clips4sale 3 months ago

Marvelous shemale in cage suck and bang sextoy

Marvelous shemale in cage suck and bang sextoy

ShemaleSin 2 days ago

Oiled Pink Sissy Plays with a Big Anal Toy

56% HD 0:39 / 20:22

Oiled Pink Sissy Plays with a Big Anal Toy

FapHouse 1 week ago

Educating A Bitchboy: Episode 4 "Last Chance"

52% HD 0:39 / 1:02:19

Educating A Bitchboy: Episode 4 "Last Chance"

Kink 14 years ago

Tranny Babe in Chasity Cage Gets Fucked by large

Tranny Babe in Chasity Cage Gets Fucked by large

aShemaleTube 4 years ago

An Honest Review: the Holytrainer Nub

66% HD 0:39 / 11:38

An Honest Review: the Holytrainer Nub

FapHouse 2 months ago

HANDBALLING AND ROSEBUTT IN CROSSDRESSER USING CAGE

HANDBALLING AND ROSEBUTT IN CROSSDRESSER USING CAGE

4Gay 3 weeks ago

Bbc9

aShemaleTube 8 months ago

Sissy cuck in chastity gets fucked 2

Sissy cuck in chastity gets fucked 2

GayCK 3 years ago

Caged sissy pushes out a load after a quick pump and dump (watch longer vids on OF: h.harryryan)

Caged sissy pushes out a load after a quick pump and dump (watch longer vids on OF: h.harryryan)

xHamster 8 months ago

Cum After 95 Days Chaste

59% HD 0:39 / 13:39

Cum After 95 Days Chaste

FapHouse 1 month ago

why fight it when you were made for this?my words own you now.. my voice is all that matters..

why fight it when you were made for this?my words own you now.. my voice is all that matters..

AnalVids 1 month ago

ound rather intimate surprise

ound rather intimate surprise

Hoes.tube 3 weeks ago

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free use submissive maid tgirl anal face fuck service slut

AnalVids 3 weeks ago

SISSY IN CHASTITY TAKES BIG COCK FOR FIRST TIME 2

SISSY IN CHASTITY TAKES BIG COCK FOR FIRST TIME 2

GayCK 4 years ago

Humiliated Sissy Custom #2

53% HD 0:10 / 14:23

Humiliated Sissy Custom #2

LoyalFans 2 months ago

Sissy fuck

aShemaleTube 8 months ago

Busty Shemale Masterbates her Thick Dildo while Locked in Chastity Belt

Busty Shemale Masterbates her Thick Dildo while Locked in Chastity Belt

4KPorn 1 week ago

Pink Sissy

aShemaleTube 2 years ago

easter bunny gets stretched out by two BBCs and cums in cage

HD 0:14 / 13:20

easter bunny gets stretched out by two BBCs and cums in cage

Clips4sale 3 days ago

Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!

Slutty maid training feminization Holly Hunt turns you into a sissy maid in chastity!

xHamster 2 weeks ago

Hardcore Anal Sissy TGirl Pool Orgy With Ria Bentley and Friends

68% HD 0:33 / 31:25

Hardcore Anal Sissy TGirl Pool Orgy With Ria Bentley and Friends

Clips4sale 8 months ago

skyler banx can t resist trans rachael belle

HD 0:30 / 28:23

skyler banx can t resist trans rachael belle

AnalVids 2 days ago

Collared Sissy slave in chastity is horny

Collared Sissy slave in chastity is horny

UrGayPorn 6 days ago

Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana

Sissy Cuckold Fed Creampie And Cum Foot Worship - Jessica Bloom ft Polieana

xHamster 3 months ago

Alexandra Star fucked like a slut

Alexandra Star fucked like a slut

aShemaleTube 2 weeks ago

TS chastity DAP wet

TS chastity DAP wet

Eporner 1 year ago

Fucking Myself In Chastity

Fucking Myself In Chastity

aShemaleTube 3 weeks ago

SLUT TRAINING

Clips4sale 1 month ago

Fan tip scene : How to make cum my crossdressed sub inside chastity

Fan tip scene : How to make cum my crossdressed sub inside chastity

4KPorn 2 years ago

Trans Bitch in latex fists her ass and kneels for doggy pose fuck with sex machine

Trans Bitch in latex fists her ass and kneels for doggy pose fuck with sex machine

XGroovy 2 years ago

Femboy Pet in Warmth Played and Smashed

Femboy Pet in Warmth Played and Smashed

Gayhub 3 months ago

SISSY IN PANTYHOSE, HIGH STILETTOS AND A INNOCENCE BELT CAME TO VISIT A GF. SISSY TRANSFORMATION

SISSY IN PANTYHOSE, HIGH STILETTOS AND A INNOCENCE BELT CAME TO VISIT A GF. SISSY TRANSFORMATION

TrannyGem 1 week ago

Wendy Going Down The Rabbit Hole

Wendy Going Down The Rabbit Hole

aShemaleTube 3 months ago

t-girl in Chastity with Lactating Boobs has Anal Climax Hands Free Sissygasm

t-girl in Chastity with Lactating Boobs has Anal Climax Hands Free Sissygasm

ShemaleSin 1 week ago

Enjoying a heavy ass pounding from fucking machine while in chastity with hands free orgasm and cums

Enjoying a heavy ass pounding from fucking machine while in chastity with hands free orgasm and cums

BoyFriendTV 1 week ago

rachael Belle - This is how you use a Fuck Machine

rachael Belle - This is how you use a Fuck Machine

aShemaleTube 9 months ago

Sissy Francis Malice College Dream

Sissy Francis Malice College Dream

xHamster 10 months ago

Reverse cowgirl for a caged beauty tranny

Reverse cowgirl for a caged beauty tranny

aShemaleTube 6 days ago

Caged and Plugged CD Whore Jasmyne Teases in Ebony Latex Leggings

Caged and Plugged CD Whore Jasmyne Teases in Ebony Latex Leggings

ShemaleSin 6 days ago

ASMR - Time for Locktober [Feminization] [Chastity] - Manga Audio Roleplay

ASMR - Time for Locktober [Feminization] [Chastity] - Manga Audio Roleplay

ShemaleSin 5 days ago

POV from big to micro chastity cage

POV from big to micro chastity cage

SissyFlix 6 days ago

Routine Inspection Pt 1

HD 0:10 / 11:43

Routine Inspection Pt 1

LoyalFans 1 week ago

Locked Up in My New Stainless Steel Chastity Belt

Locked Up in My New Stainless Steel Chastity Belt

Xfeed 1 month ago

Trannys Insatiable Thirst Massive Cock Slams Her Gaping Holes

Trannys Insatiable Thirst Massive Cock Slams Her Gaping Holes

4KPorn 3 weeks ago

TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED

TRANS YEEHAW: Sloppy BJ & Ride By Canadian Cowgirl ABRIDGED

xHamster 1 month ago

Sissy slut in chastity takes it in the ass in multiple positions like a good trans cuck femboy slave should!

Sissy slut in chastity takes it in the ass in multiple positions like a good trans cuck femboy slave should!

xHamster 1 year ago

Pounding Sammi Smith into submission- Shes my Permanent Wang-Thrall Now!

Pounding Sammi Smith into submission- Shes my Permanent Wang-Thrall Now!

ShemaleSin 3 weeks ago

Kylie

aShemaleTube 1 year ago

Tgirl ravages her caboose for father on FaceTime

Tgirl ravages her caboose for father on FaceTime

TrannyGem 2 months ago

sissys chastity

sissys chastity

aShemaleTube 4 weeks ago

Sissy Hailey And BBC

Sissy Hailey And BBC

aShemaleTube 2 months ago

Spandex Crossdresser rails XXL fuck sticks

Spandex Crossdresser rails XXL fuck sticks

Gayhub 1 month ago

Make Me Your Whore and Destroy My Sissy Holr

Make Me Your Whore and Destroy My Sissy Holr

SissyFlix 1 week ago

RUSSIAN FEMBOY TEARS UP WITH DOMME FOR THE VERY FIRST TIME WITH a YAM-SIZED BELT DICK, STRAPPED WITH a INNOCENCE

RUSSIAN FEMBOY TEARS UP WITH DOMME FOR THE VERY FIRST TIME WITH a YAM-SIZED BELT DICK, STRAPPED WITH a INNOCENCE

TrannyGem 3 years ago

you’ve gone too far, beta...there’s no turning back, your manhood is gone, and you’re nothing but a pretty little sissy now. might as well embrace it and seal your fate !

58% 0:30 / 34:27

you’ve gone too far, beta...there’s no turning back, your manhood is gone, and you’re nothing but a pretty little sissy now. might as well embrace it and seal your fate !

PornBox 1 month ago

transgirl dildo in the ass on webcam

transgirl dildo in the ass on webcam

aShemaleTube 3 years ago

Hole training

aShemaleTube 2 years ago

Tranny is slobber roasted by her gf and humping machine

Tranny is slobber roasted by her gf and humping machine

TrannyGem 3 years ago

Chastity Caged Sissies

Chastity Caged Sissies

aShemaleTube 3 months ago

Chastity Teen Fucked By Her Daddy

Chastity Teen Fucked By Her Daddy

Tranny.one 3 years ago

chastity fuckdolls reverse gb

66% HD 0:30 / 33:38

chastity fuckdolls reverse gb

AnalVids 2 weeks ago

Chastity Slave Eager to Suck Mommy's Cock

55% HD 0:10 / 8:18

Chastity Slave Eager to Suck Mommy's Cock

LoyalFans 1 month ago

Ass to mouth training for sissy while she waits for daddy

Ass to mouth training for sissy while she waits for daddy

xHamster 2 years ago

Hot and Nasty Dildo Babe #2.

Hot and Nasty Dildo Babe #2.

aShemaleTube 7 months ago

Whore Fuck Machine

Whore Fuck Machine

xHamster 2 years ago

Pegging and Spandex Mitten Handballing Trampy V-Card Sissy with Xxl Black Faux-Cock by Domina Mercer

Pegging and Spandex Mitten Handballing Trampy V-Card Sissy with Xxl Black Faux-Cock by Domina Mercer

TrannyGem 2 years ago

Taniax Get a Sissygasm

66% HD 0:39 / 12:13

Taniax Get a Sissygasm

FapHouse 5 days ago

My Sweet, Soft Body😳

Premium 4K 0:12

My Sweet, Soft Body😳

Flirt4Free 1 week ago

Wollip Chastity sex

Wollip Chastity sex

PornOne 2 weeks ago

Femboy shrieks from tearing up

Femboy shrieks from tearing up

TrannyGem 8 months ago

Julia X taking Daddy's Cock

Julia X taking Daddy's Cock

TrannyGem 6 years ago

Cute Trans Fucks Caged Tgirl

Cute Trans Fucks Caged Tgirl

4KPorn 10 months ago

Oiled Sissy in Flat Chastity Riding Massive Dildos

Oiled Sissy in Flat Chastity Riding Massive Dildos

SissyFlix 5 days ago

Together in a life of chastity

Together in a life of chastity

xHamster 8 months ago

Dungeon Chastity and fuck

Dungeon Chastity and fuck

aShemaleTube 1 month ago

Bound blonde tranny Lianna Lawson big dick wanked by master Dominic Pacifico

Bound blonde tranny Lianna Lawson big dick wanked by master Dominic Pacifico

4Wank 7 months ago

Creampie For A Chastity Whore

Creampie For A Chastity Whore

Eporner 4 years ago

Femboys Raine and Flare fucking in new apartment! (Teaser)

Femboys Raine and Flare fucking in new apartment! (Teaser)

Mensporn 1 week ago

Trans Lady Ass Bred After Dick Sucking

Trans Lady Ass Bred After Dick Sucking

TransVibe 8 months ago

Hot - Sissy Femboy With Chastity Cage Offers Hung College Bully His Tight Ass To Fuck

Hot - Sissy Femboy With Chastity Cage Offers Hung College Bully His Tight Ass To Fuck

3Gayz 6 days ago

BBC destroy hard sissy with big ass

BBC destroy hard sissy with big ass

xHamster 7 months ago

BBC Vs Sissy In Chastity 2

BBC Vs Sissy In Chastity 2

Eporner 4 months ago

Sissy Life In Chastity

Sissy Life In Chastity

BeMyHole 1 year ago

Trans Hotty Cums in Chastity During the time that Getting Screwed

Trans Hotty Cums in Chastity During the time that Getting Screwed

ShemaleSin 1 week ago

Anal sex with sissymaid Kitsy in chastity and bunny ears

Anal sex with sissymaid Kitsy in chastity and bunny ears

ShemaleSin 3 years ago

30 days in chastity & anal orgasm 720p

39% HD 0:15 / 9:10

30 days in chastity & anal orgasm 720p

Clips4sale 2 years ago

Secretary Tease

Secretary Tease

ShemaleSin 1 week ago

Cute Trans Fucks Caged Tgirl 2

Cute Trans Fucks Caged Tgirl 2

4KPorn 10 months ago

Chastity Sissy Games: Pegging and Pleasure in Cage Mistress Julia femdom

Chastity Sissy Games: Pegging and Pleasure in Cage Mistress Julia femdom

xHamster 1 year ago

CHASTITY slave CUMS while PEGGING after training with some XXL toys

CHASTITY slave CUMS while PEGGING after training with some XXL toys

xHamster 3 weeks ago

Near a Neighboring Village, a Bro Satisfied a sluts inside a Chastity

Near a Neighboring Village, a Bro Satisfied a sluts inside a Chastity

CrazyPorn 3 years ago

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charming trans in shlong chastity cage has an anal prostate climax and cum explodes during the time that drilled hard and fast with a biggest sex tool screw machine

ShemaleSin 3 years ago

Virginity guide : A review of all iron purity cages by sissy joyce55

Virginity guide : A review of all iron purity cages by sissy joyce55

TrannyGem 8 months ago

Trans Chastity Slut Dusti Bunni Gets Leashed & Used by Stud

Trans Chastity Slut Dusti Bunni Gets Leashed & Used by Stud

xHamster 3 months ago

Princess butt slut orgasms🍑💦

Princess butt slut orgasms🍑💦

aShemaleTube 6 months ago

CD Slut in Chastity Sucs Coc

CD Slut in Chastity Sucs Coc

aShemaleTube 12 years ago

Flat chastity cage with penis plug Cumshot

Flat chastity cage with penis plug Cumshot

SissyFlix 1 week ago

2 Sissies 1 Chastity Cage

2 Sissies 1 Chastity Cage

TransVibe 5 months ago

Bnwo Ai Training

Bnwo Ai Training

xHamster 3 months ago

Armbinder Chastity Self Servitude - Sissy Maid Getting Willing

Armbinder Chastity Self Servitude - Sissy Maid Getting Willing

ShemaleSin 1 week ago

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