Chastity Videos - Trans (44,921)

Sissy Hfo and Permanent Chastity

Sissy Hfo and Permanent Chastity

FapHouse 1 week ago

HUGE BBC fucks & breeds kinky brunette shemale

HUGE BBC fucks & breeds kinky brunette shemale

aShemaleTube 5 days ago

BBC Vs Chastity Sissy

BBC Vs Chastity Sissy

Eporner 4 days ago

Dancing in My Flat Chastity Cage

64% HD 0:08 / 0:46

Dancing in My Flat Chastity Cage

FapHouse 1 year ago

St33le And H4v0k

St33le And H4v0k

Eporner 1 week ago

Sissy Joyce fucked by a Big Black Cock

57% HD 1:01 / 10:04

Sissy Joyce fucked by a Big Black Cock

FapHouse 2 years ago

Unboxing of Gifts: Chastity Cage, Huge Buttplug and More

HD 1:01 / 31:00

Unboxing of Gifts: Chastity Cage, Huge Buttplug and More

FapHouse 1 week ago

POV: You are fucking me!!

POV: You are fucking me!!

xHamster 1 week ago

Chastity TS Vs BBC Indoor

Chastity TS Vs BBC Indoor

BeMyHole 1 week ago

Down the sissy rabbit hole - My Story

55% HD 0:10 / 17:16

Down the sissy rabbit hole - My Story

LoyalFans 4 weeks ago

Trans Sow Loren Aprile Rectal Abasement

Trans Sow Loren Aprile Rectal Abasement

TrannyGem 1 week ago

FEMOUT XXX - Compilation Updates 17th to 21st Nov'25

FEMOUT XXX - Compilation Updates 17th to 21st Nov'25

xHamster 1 week ago

Gal Goth

aShemaleTube 4 days ago

Sissy Femboy In Chastity Cage Fucked

Sissy Femboy In Chastity Cage Fucked

aShemaleTube 1 week ago

Chastity TS Vs BBC Fuck

Chastity TS Vs BBC Fuck

BeMyHole 3 months ago

Sissy Hope Compilation 14

Sissy Hope Compilation 14

xHamster 1 week ago

Sissy Bride in Chastity

Sissy Bride in Chastity

FapHouse 1 week ago

Trans Purity Crazy ass-fuck fake penis railing

Trans Purity Crazy ass-fuck fake penis railing

TrannyGem 2 years ago

Trans Angels - Doms Crystal Thayer & Lauren Phillips Put A Leash & A Chastity Cage On Tony Orlando

Trans Angels - Doms Crystal Thayer & Lauren Phillips Put A Leash & A Chastity Cage On Tony Orlando

PornFreeNow 1 week ago

Upgrading My Cage Game While Riding My Dildo

Upgrading My Cage Game While Riding My Dildo

BeMyHole 5 days ago

Sissy Hailey And BBC

Sissy Hailey And BBC

aShemaleTube 10 months ago

Trans Babe Sophia Calypso In Chastity Anal Fucked In Pov

Trans Babe Sophia Calypso In Chastity Anal Fucked In Pov

getTranny 1 week ago

Morning Bang Pov

Morning Bang Pov

ShemaleSin 2 weeks ago

Trans Beauties - Doms Crystal Thayer & Lauren Phillips Put A Leash & A Chastity Cage On Tony Orlando

Trans Beauties - Doms Crystal Thayer & Lauren Phillips Put A Leash & A Chastity Cage On Tony Orlando

Lesbian8 1 week ago

Crossdresser Sex rossiя

Crossdresser Sex rossiя

aShemaleTube 6 years ago

Naughty blonde trap removes chastity & cums

Naughty blonde trap removes chastity & cums

aShemaleTube 1 year ago

HUGE BBC balls deep in shemale pussy # 2

HUGE BBC balls deep in shemale pussy # 2

aShemaleTube 1 week ago

BBC6

aShemaleTube 7 months ago

Mistress and bbc train sissy in chastity

Mistress and bbc train sissy in chastity

aShemaleTube 6 months ago

Caged Cowgirls

aShemaleTube 3 months ago

trans cutie doxy in chastity gets drilled by machine and gapes - Ella Mox

trans cutie doxy in chastity gets drilled by machine and gapes - Ella Mox

SortPorn 1 week ago

Mistress destroys her sissy's ass with a huge dildo

Mistress destroys her sissy's ass with a huge dildo

Juicexxx 1 week ago

two slim brunette trans ladies have a good time on webcam

two slim brunette trans ladies have a good time on webcam

aShemaleTube 3 years ago

Sissy Femboy Anal Masturbation Compilation - Chastity and Feminization Progress

Sissy Femboy Anal Masturbation Compilation - Chastity and Feminization Progress

xHamster 1 year ago

Chastity futa cbt

Chastity futa cbt

Eporner 6 days ago

TRANSSEXUAL bitch has joy with two stiffys

TRANSSEXUAL bitch has joy with two stiffys

TrannyGem 1 week ago

Pretty little femboy loves BBC in her asshole

Pretty little femboy loves BBC in her asshole

Eporner 2 months ago

I cornered my Sissy with my Belt Cock and give a rigid Pegging. Total OnlyFans • FEMFORHER

I cornered my Sissy with my Belt Cock and give a rigid Pegging. Total OnlyFans • FEMFORHER

TrannyGem 6 days ago

Cute tranny in chastity playing with big dildos and anal fisting and fisting

Cute tranny in chastity playing with big dildos and anal fisting and fisting

aShemaleTube 1 week ago

Sissy Creampied After Toy Play

Sissy Creampied After Toy Play

Eporner 1 week ago

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

The Secret to Achieving Female Squirting Orgasm. Sissification for Crossdressers (part 4)

xHamster 1 month ago

Taylor's sissy hole BBC destruction

Taylor's sissy hole BBC destruction

xHamster 1 year ago

Lily's Solo Toy Play in PVC Corset and Chastity

Lily's Solo Toy Play in PVC Corset and Chastity

xHamster 4 years ago

Sissy Candy plays with numerous fuck sticks at the same time with butt to jaws

Sissy Candy plays with numerous fuck sticks at the same time with butt to jaws

TrannyGem 1 week ago

locked girl's butthole pleasure

locked girl's butthole pleasure

BeMyHole 5 years ago

onlyfans - fayefayebaby this is what every transgirl needs porn video

onlyfans - fayefayebaby this is what every transgirl needs porn video

TransDoe 11 months ago

Cute Sissygasms in Chastity Cage Anal Cumslut Jessica Bloom

Cute Sissygasms in Chastity Cage Anal Cumslut Jessica Bloom

PornFreeNow 1 week ago

Chastity TS Vs BBC

Chastity TS Vs BBC

BeMyHole 1 year ago

My lunch Break... LUVS HER THUMBS MORE!!!

My lunch Break... LUVS HER THUMBS MORE!!!

TrannyGem 1 week ago

Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2

Mamou with Rachelle Karol I Dominate a Pretty Submissive Before Taking Her Part 2

xHamster 2 weeks ago

TS Natalie Mars fisted and stretched by MILF Penny Barber

TS Natalie Mars fisted and stretched by MILF Penny Barber

UrGayPorn 4 months ago

stupid caged cunt worships master s big cock

stupid caged cunt worships master s big cock

PornBox 2 weeks ago

How I became a bbc addict

How I became a bbc addict

aShemaleTube 6 months ago

sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!

sissy orgasm on a fucking machine ! your trap rides a dildo and cums in the chastity belt!

xHamster 1 year ago

onlyfans - sissy joyce @sissyjoyce i know where you want to kiss porn video

onlyfans - sissy joyce @sissyjoyce i know where you want to kiss porn video

TransDoe 9 months ago

She's all alone with her dildo

She's all alone with her dildo

aShemaleTube 1 year ago

Jay Brock's Anal Destruction Challenge, 1500 Thrusts!

Jay Brock's Anal Destruction Challenge, 1500 Thrusts!

xHamster 1 month ago

Caged Sissy Knows Her Place In Front Of BBC

Caged Sissy Knows Her Place In Front Of BBC

aShemaleTube 3 months ago

Glazing Her Lil' Inverted Pearl In Sissy Juices

Glazing Her Lil' Inverted Pearl In Sissy Juices

TrannyGem 1 year ago

Chastity Caged Sissies

Chastity Caged Sissies

aShemaleTube 10 months ago

Hot Crossdresser alongside enormous tits and dick cage jerks-off!

Hot Crossdresser alongside enormous tits and dick cage jerks-off!

Kams.com 10 months ago

Gets Fucked Natalie Mars Passionate Sex With Owen Gray

Gets Fucked Natalie Mars Passionate Sex With Owen Gray

BeMyHole 2 years ago

Sissygasm - cuming in chastity 2

Sissygasm - cuming in chastity 2

GayCK 1 month ago

Miss April stretched me out

Miss April stretched me out

aShemaleTube 3 days ago

Sissy-Bondage-Bunny-for-BBC-Master

Sissy-Bondage-Bunny-for-BBC-Master

aShemaleTube 6 months ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 1

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 1

aShemaleTube 1 week ago

Trans maid at your service

Trans maid at your service

ShemaleSin 2 years ago

jessyca 2 vs naponap 3

jessyca 2 vs naponap 3

aShemaleTube 1 year ago

Femboy Raine in flat chastity riding best friend Flare

Femboy Raine in flat chastity riding best friend Flare

xHamster 5 months ago

onlyfans - bambifyme comfy pumpkin mreasydeck spread and ready to be pleased porn video

onlyfans - bambifyme comfy pumpkin mreasydeck spread and ready to be pleased porn video

TransDoe 8 months ago

Obey your master!

Obey your master!

aShemaleTube 1 year ago

Femboy sissy training rides BBC dildo

Femboy sissy training rides BBC dildo

aShemaleTube 1 year ago

Training Sissy Throat and Pussy 3

Training Sissy Throat and Pussy 3

BoyFriendTV 3 months ago

Trans Beauties Share a Schlong and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

Trans Beauties Share a Schlong and Chastity Cage Huge Load of Cum Jessica Bloom and JenbyDoll

PornFreeNow 6 days ago

Trans Gals Share a Wang and Chastity Cage Giant Load of Cum Jessica Bloom and JenbyDoll

Trans Gals Share a Wang and Chastity Cage Giant Load of Cum Jessica Bloom and JenbyDoll

BigTitsLust 5 days ago

trans beauty wench in chastity gets banged by machine and gapes - Ella Mox

trans beauty wench in chastity gets banged by machine and gapes - Ella Mox

FreePorn8 1 week ago

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 2

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 2

aShemaleTube 1 week ago

Hot Shemale With Cock In Chastity And Buttplug Up Her Ass Showing Her Skills With Dildo, Part 1

Hot Shemale With Cock In Chastity And Buttplug Up Her Ass Showing Her Skills With Dildo, Part 1

MyLust 5 years ago

femboy boucing and groaning on a monstrous fake penis

femboy boucing and groaning on a monstrous fake penis

TrannyGem 1 year ago

Sissy with big ass in fishnet showing her ass and cock in chastity cage

Sissy with big ass in fishnet showing her ass and cock in chastity cage

TransG 1 month ago

Cute Sissygasms in Chastity Cage Anal Cumslut Jessica Bloom

Cute Sissygasms in Chastity Cage Anal Cumslut Jessica Bloom

BigTitsLust 1 week ago

Trans Cuties Share a Ramrod and Chastity Cage Biggest Load of Cum Jessica Bloom and JenbyDoll

Trans Cuties Share a Ramrod and Chastity Cage Biggest Load of Cum Jessica Bloom and JenbyDoll

Lesbian8 6 days ago

Cute T-girl Cums Through Chastity

Cute T-girl Cums Through Chastity

Dafreeporn 1 month ago

Transgirl in chastity loves black cock

Transgirl in chastity loves black cock

Eporner 1 day ago

Trans Dame Smashed in Restrain Bondage and Virginity

Trans Dame Smashed in Restrain Bondage and Virginity

TrannyGem 2 weeks ago

Inverted chastity cage is intense

Inverted chastity cage is intense

aShemaleTube 1 week ago

Femboy POV Banging Compilation

Femboy POV Banging Compilation

ShemaleSin 2 weeks ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

ShemaleSin 3 weeks ago

Latex Overspread Pegging and Fisting for Hopeless Sissy Wench by Mistresse Mercer

Latex Overspread Pegging and Fisting for Hopeless Sissy Wench by Mistresse Mercer

ShemaleSin 2 weeks ago

Getting Pummeled Until I'm Bellowing!! Camshow Compilation

Getting Pummeled Until I'm Bellowing!! Camshow Compilation

TrannyGem 11 months ago

Femdom Mastix real amateur hotwife cuck pair Rave Magic sissy feminization anal ding-dong pegging

Femdom Mastix real amateur hotwife cuck pair Rave Magic sissy feminization anal ding-dong pegging

ShemaleSin 2 weeks ago

femboy gets railed by kraken in chastity as they use there dick as a pussy

femboy gets railed by kraken in chastity as they use there dick as a pussy

xHamster 11 months ago

Feminized Shemale Gets Horny

Feminized Shemale Gets Horny

xHamster 3 years ago

Sissy cuck in chastity gets fucked 2

Sissy cuck in chastity gets fucked 2

GayCK 4 years ago

Sissy Hope Compilation 15

Sissy Hope Compilation 15

BigTitsLust 6 days ago

Timmy Boy in Chastity Takes Rough Anal Training XXX

Timmy Boy in Chastity Takes Rough Anal Training XXX

FapHouse 2 weeks ago

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Spandex Sissy Punished By V-card Fuckmachine Smacking Dickblowing Pegging By Domina Mercer

Xshemale 5 days ago

Sissy bimbo kitten

Sissy bimbo kitten

xHamster 1 month ago

Concupiscent shemale with large weenie screws her boyfriends butt

Concupiscent shemale with large weenie screws her boyfriends butt

ShemaleSin 1 year ago

Jackie

aShemaleTube 5 months ago

Hot Transgirl Uses Biggest Buttplug Then Jerks Hard Jock For Huge Load of Cum

Hot Transgirl Uses Biggest Buttplug Then Jerks Hard Jock For Huge Load of Cum

PornFreeNow 3 weeks ago

Crimson Spandex girl Assfuck Have Fun Fuck Sticks, Butt-Plugs, Mayo, Coffee

Crimson Spandex girl Assfuck Have Fun Fuck Sticks, Butt-Plugs, Mayo, Coffee

TrannyGem 1 week ago

Trans Fun

Eporner 2 months ago

What chastity does to whiteboys

What chastity does to whiteboys

xHamster 1 year ago

Fisting Double Sissygasm Cumshots

Fisting Double Sissygasm Cumshots

xHamster 4 months ago

Sissy school in chastity and butt plug

Sissy school in chastity and butt plug

xHamster 3 weeks ago

Sissy Femboy In Chastity Cage Fucked

Sissy Femboy In Chastity Cage Fucked

Eporner 2 weeks ago

Sexy Fucking Myself In Chastity Amateur

Sexy Fucking Myself In Chastity Amateur

KeekAss 1 month ago

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

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 4 years ago

TS Istol Fucked BBC

TS Istol Fucked BBC

aShemaleTube 1 month ago

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

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

xHamster 1 month ago

Sissy Slut Training

Sissy Slut Training

xHamster 1 year ago

Trans Cuties Jock Sucking Triple Threat

Trans Cuties Jock Sucking Triple Threat

BigTitsLust 3 weeks ago

Hands-free cumshots in a cage for mistress

Hands-free cumshots in a cage for mistress

xHamster 1 month ago

Taryn Elizabeth gets strapon while in chastity

Taryn Elizabeth gets strapon while in chastity

AbTranny 1 year ago

Sissy in chastity cums on BBC

Sissy in chastity cums on BBC

Eporner 1 month ago

Whorey femboy is penalized by dressed in a virginity cell and is not permitted to jizz

Whorey femboy is penalized by dressed in a virginity cell and is not permitted to jizz

5Gays 1 week ago

Trans Girl Kitty Clip / Fufu Compilation 5

Trans Girl Kitty Clip / Fufu Compilation 5

BallsAndBoobs 4 weeks ago

RoxyDominaUK - Pegging you in Chastity BDSM instructions!

RoxyDominaUK - Pegging you in Chastity BDSM instructions!

HD21 1 month ago

Redhead Trans Girl Submits To A Bbc While In Chastity

Redhead Trans Girl Submits To A Bbc While In Chastity

getTranny 5 days ago

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