Chastity Videos - Trans (48,163)

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

HD 0:26 / 10:05

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

Clips4sale 5 months ago

Caged Sissy Massage Her Prostate With Sex toy

Caged Sissy Massage Her Prostate With Sex toy

ShemaleSin 5 months ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 5 months ago

Diamond Chastity - Motel Fun

Diamond Chastity - Motel Fun

PornUse 4 months ago

Sissy Self Pulverize Sunday

Sissy Self Pulverize Sunday

Gayhub 4 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 4 months ago

GIRLFRIENDS IN THE ROOM DECIDED TO FUCK IN ANAL. BLONDE FUCKING HER ASS FOR BIG BBS.

GIRLFRIENDS IN THE ROOM DECIDED TO FUCK IN ANAL. BLONDE FUCKING HER ASS FOR BIG BBS.

XVideos 3 years ago

Why are you leaking sissy boi? ?

Why are you leaking sissy boi? ?

XVideos 3 years ago

Want some boipussi-chocolate??

Want some boipussi-chocolate??

XVideos 3 years ago

Trans Beauty in Chastity Fucked Missionary

Trans Beauty in Chastity Fucked Missionary

XVideos 2 years ago

destroying my big sissy ass with a fuck machine and huge dildos

destroying my big sissy ass with a fuck machine and huge dildos

XVideos 2 years ago

for my fans 09 - JennStarTS The Tranny MILF Best ASS

for my fans 09 - JennStarTS The Tranny MILF Best ASS

XVideos 2 years ago

for my fans 06 - JennStarTS The Tranny MILF Best ASS

for my fans 06 - JennStarTS The Tranny MILF Best ASS

XVideos 2 years ago

misr4 - chastity cage cum on fishnet

misr4 - chastity cage cum on fishnet

XVideos 2 years ago

sissy captions for sissies - big ass sissy slut

sissy captions for sissies - big ass sissy slut

XVideos 2 years ago

horny sissy training with huge dildos in chastity ass gape

horny sissy training with huge dildos in chastity ass gape

XVideos 5 years ago

POV Blowjob by step daughter who seduces you into being her cuckold bitch step dad and suck out the creampies from her pussy and locks you in chastity

POV Blowjob by step daughter who seduces you into being her cuckold bitch step dad and suck out the creampies from her pussy and locks you in chastity

XVideos 6 years ago

Selfbondage2, My second attempt at crossdressed selfbondage, this time using remote contol vibrating eggs

Selfbondage2, My second attempt at crossdressed selfbondage, this time using remote contol vibrating eggs

XVideos 7 years ago

Sissy Oksana riding dildo with a dick in a cage Cumshot

Sissy Oksana riding dildo with a dick in a cage Cumshot

XVideos 7 years ago

white boi watching bbc vidoes caged

white boi watching bbc vidoes caged

XVideos 8 years ago

Ladyboy Strip and Piss Outdoor in Chastity Cage and Plug

HD 0:39 / 16:20

Ladyboy Strip and Piss Outdoor in Chastity Cage and Plug

FapHouse 5 months ago

Você Não Vai Acreditar Quem Está Por Trás Dessa Transa

Premium HD 11:51

Você Não Vai Acreditar Quem Está Por Trás Dessa Transa

Sheer 5 months ago

Desire Sweet Private Show

HD 2:00 / 24:28

Desire Sweet Private Show

Flirt4Free 5 months ago

Fucking Sexy Sissy in Chastity - Compilation 4

Fucking Sexy Sissy in Chastity - Compilation 4

xHamster 5 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 5 months ago

Asian Sissy Deepthroat in Chastity & Lingerie

Asian Sissy Deepthroat in Chastity & Lingerie

xHamster 5 months ago

Alice Kizar Private Show

Alice Kizar Private Show

Flirt4Free 5 months ago

EU E A MINHA AMIGA DIVIDIMOS A PIROCA DO MARIDO DELA - ALICE HAEL

EU E A MINHA AMIGA DIVIDIMOS A PIROCA DO MARIDO DELA - ALICE HAEL

XVideosRed 5 months ago

Ep2 Testing My New Sissy: Cocksucker and Anal Fingering Training - Mistress Julia

Ep2 Testing My New Sissy: Cocksucker and Anal Fingering Training - Mistress Julia

FapHouse 5 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 5 months ago

Oriental shemale is wearing a chastity, bangs a sex tool and cums multiple times

Oriental shemale is wearing a chastity, bangs a sex tool and cums multiple times

ShemaleSin 5 months ago

Testing my new chasity like a pussy

Testing my new chasity like a pussy

xHamster 5 months ago

Slamming a Clippd Trans Girls Prostate Till She Squirts

Slamming a Clippd Trans Girls Prostate Till She Squirts

XVideos 5 months ago

my both holes full of pleasure while i ride a dildo and I make a squirt mess here!!! - Part 2

HD 2:00 / 14:53

my both holes full of pleasure while i ride a dildo and I make a squirt mess here!!! - Part 2

Flirt4Free 4 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 4 months ago

Big Stretch!!

xHamster 4 months ago

Start of the dilation session

Start of the dilation session

xHamster 4 months ago

Cock Bondage with Crossdressing Gagged and Cuffed

Cock Bondage with Crossdressing Gagged and Cuffed

FapHouse 4 months ago

Sissy Surrender - Glasses and Lipstick Humiliation Asmr Clip by Findom Goaldigger

Sissy Surrender - Glasses and Lipstick Humiliation Asmr Clip by Findom Goaldigger

FapHouse 4 months ago

Trans in Chastity Fucked Raw - Compilation 3

HD 0:39 / 20:06

Trans in Chastity Fucked Raw - Compilation 3

FapHouse 4 months ago

Desire Sweet Private Show

HD 2:00 / 34:33

Desire Sweet Private Show

Flirt4Free 4 months ago

Sissy Laura - Cumming With A BBC In My Ass (Cumshot)

Sissy Laura - Cumming With A BBC In My Ass (Cumshot)

XVideos 9 years ago

Trans Woman in Chastity Fucked Hard - Compilation 5

55% HD 0:39 / 20:10

Trans Woman in Chastity Fucked Hard - Compilation 5

FapHouse 6 months ago

gymgirl fuck her ass in chastity

gymgirl fuck her ass in chastity

AnalVids 6 months ago

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

66% 1:01 / 18:20

Sissy Maid Service Practicing on a Dildo at Her Fake Glory Hole

FapHouse 6 months ago

Desire Sweet Private Show

HD 2:00 / 53:03

Desire Sweet Private Show

Flirt4Free 6 months ago

Amateur femboy fucked - she really enjoyed my BBC in her Sissy ass part2

Amateur femboy fucked - she really enjoyed my BBC in her Sissy ass part2

BallsAndBoobs 6 months ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 10

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 10

xHamster 6 months ago

Sophia Loreen Private Show

4K 2:00 / 10:20

Sophia Loreen Private Show

Flirt4Free 6 months ago

Chastity Cage Sissygasm - Huge Spunk fountain (Shorties)

Chastity Cage Sissygasm - Huge Spunk fountain (Shorties)

ShemaleSin 6 months ago

TRANSEI GOSTOSO COM MEU CUNHADO NO SOFÁ - LUANA PRADO

Premium HD 29:04

TRANSEI GOSTOSO COM MEU CUNHADO NO SOFÁ - LUANA PRADO

Sheer 6 months ago

Memorable moment from "Tina Noxx stretches her poor butt with an inflatable plug"

Memorable moment from "Tina Noxx stretches her poor butt with an inflatable plug"

xHamster 6 months ago

Pig Hole Plug Plus Vibrate

Pig Hole Plug Plus Vibrate

xHamster 6 months ago

Asian Sissy Bunny Deepthroat Cumshot

Asian Sissy Bunny Deepthroat Cumshot

FapHouse 6 months ago

Spectacular moment from "The first sensations of the sissy whore from the chastity belt"

Spectacular moment from "The first sensations of the sissy whore from the chastity belt"

xHamster 6 months ago

Story of When Stepdaddy Me Out. First Week. Anal Toy.

Story of When Stepdaddy Me Out. First Week. Anal Toy.

FapHouse 5 months ago

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 2

55% 4K 2:00 / 14:52

Best firm round ass BOUNCING IN YOUR COCK! Enjoy the wildest ride while I feel you so deep! Lets cum?? (squirt) (puppyeyes) - Part 2

Flirt4Free 5 months ago

Sissy Dog Show

xHamster 6 months ago

Trans Chastity Beauties Tease With Toys

Trans Chastity Beauties Tease With Toys

getTranny 6 months ago

Fucking Trans Woman in Chastity - Compilation 8

HD 0:39 / 20:18

Fucking Trans Woman in Chastity - Compilation 8

FapHouse 5 months ago

Chastity Advise for Sissies

Chastity Advise for Sissies

xHamster 6 months ago

Fucking Sexy Sissy in Chastity - Compilation 4

Fucking Sexy Sissy in Chastity - Compilation 4

FapHouse 5 months ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 5 months ago

sissies anal competition: who ll stay in the cage? who s in the basement? mistress julia

63% HD 0:30 / 15:01

sissies anal competition: who ll stay in the cage? who s in the basement? mistress julia

PornBox 5 months ago

Valentina Ramirezz Private Show

Valentina Ramirezz Private Show

Flirt4Free 5 months ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 5 months ago

Begging for Your Cum Pt 3!

HD 0:39 / 18:29

Begging for Your Cum Pt 3!

FapHouse 5 months ago

Sophia Loreen Party on Oct 4, 2025

4K 2:00 / 42:43

Sophia Loreen Party on Oct 4, 2025

Flirt4Free 5 months ago

Full Version of My First Time Using a Chastity Cage for My Trans Big Penis

HD 1:01 / 24:10

Full Version of My First Time Using a Chastity Cage for My Trans Big Penis

FapHouse 5 months ago

ela tem pau e ele gosta! trans comendo hetero curioso

ela tem pau e ele gosta! trans comendo hetero curioso

AnalVids 5 months ago

Whorey Sissy Bare Outdoors

Whorey Sissy Bare Outdoors

TrannyGem 5 months ago

Epic moment from "Sissy slut slaps her ass with whip and paddle"

Epic moment from "Sissy slut slaps her ass with whip and paddle"

xHamster 5 months ago

Transsexual in chastity teased anal large sex tool and anal climax

Transsexual in chastity teased anal large sex tool and anal climax

ShemaleSin 5 months ago

Tgirl Footjob and blowjob

Tgirl Footjob and blowjob

BallsAndBoobs 5 months ago

Must-share moment from "Sissy in miniskirt and chastity with big dildo outdoor"

Must-share moment from "Sissy in miniskirt and chastity with big dildo outdoor"

xHamster 5 months ago

Mamou avec Rachelle Karol baise, cravache &eacute_lectrique et &eacute_jaculation buccale ba 4.3

Mamou avec Rachelle Karol baise, cravache &eacute_lectrique et &eacute_jaculation buccale ba 4.3

XVideos 5 months ago

Mamou avec Rachelle Karol j&#039_&eacute_jacule sur une jolie soumise &agrave_ lunette partie 4 abo

Mamou avec Rachelle Karol j&#039_&eacute_jacule sur une jolie soumise &agrave_ lunette partie 4 abo

XVideosRed 5 months ago

Sissy Lucy pissing in her chastity cage

Sissy Lucy pissing in her chastity cage

RedTube Unknown

Tiffany Kitten the Sexy Blonde Sissy Crossdresser Babe Shows Her Gorgeous Body and Fucks Her BBC Dildo Part 2

Tiffany Kitten the Sexy Blonde Sissy Crossdresser Babe Shows Her Gorgeous Body and Fucks Her BBC Dildo Part 2

xHamster 5 months ago

Asian Sissy Chastity Anal Cumshot

Asian Sissy Chastity Anal Cumshot

FapHouse 5 months ago

Pinked out chastised Sissy Kenzie Star rides a big dildo

Pinked out chastised Sissy Kenzie Star rides a big dildo

xHamster 5 months ago

Cock and Ball Bondage with Nipple Clamps and Butt Plug

Cock and Ball Bondage with Nipple Clamps and Butt Plug

FapHouse 4 months ago

Cock and Ball Bondage Acting as Chastity with Nipple Clamps Butt Plug and Crossdressing

Cock and Ball Bondage Acting as Chastity with Nipple Clamps Butt Plug and Crossdressing

FapHouse 4 months ago

Sophia Loreen Private Show

4K 2:00 / 14:03

Sophia Loreen Private Show

Flirt4Free 4 months ago

Sabrina Smiith Private Show

Sabrina Smiith Private Show

Flirt4Free 4 months ago

Sabrina Smiith Private Show

4K 2:00 / 11:58

Sabrina Smiith Private Show

Flirt4Free 3 months ago

Sabrina Smiith Private Show

HD 2:00 / 10:53

Sabrina Smiith Private Show

Flirt4Free 4 months ago

Desire Sweet Private Show

HD 2:00 / 27:25

Desire Sweet Private Show

Flirt4Free 5 months ago

Sara & Elver Private Show

Sara & Elver Private Show

Flirt4Free 3 months ago

Teen Chastity Bondage And Used To Please A Big White Cock

Teen Chastity Bondage And Used To Please A Big White Cock

ShemaleSex 3 months ago

Sissygasm Chastity Vibrator Machine Dildo Fucked Pulpyboy69

HD 0:39 / 15:15

Sissygasm Chastity Vibrator Machine Dildo Fucked Pulpyboy69

FapHouse 2 months ago

Lucas Miiller Private Show

Lucas Miiller Private Show

Flirt4Free 2 months ago

Colombian Boys Private Show

HD 2:00 / 16:12

Colombian Boys Private Show

Flirt4Free 6 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 2 months ago

Large butt transsexual bangs chap in small chastity

Large butt transsexual bangs chap in small chastity

ShemaleSin 2 months ago

Chastity Release Challenge by Tranny Girl! You Have to Cum in One Minute!! German

66% HD 0:08 / 0:40

Chastity Release Challenge by Tranny Girl! You Have to Cum in One Minute!! German

FapHouse 2 months ago

Trans Woman in Chastity Fucked Hard - Compilation 3

Trans Woman in Chastity Fucked Hard - Compilation 3

xHamster 2 months ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 1 month ago

Multiple Cum in Chastity and Vibrator While Riding Dildo Hard Pulpyboy69

Multiple Cum in Chastity and Vibrator While Riding Dildo Hard Pulpyboy69

FapHouse 2 months ago

Sissy get fucked by sex maschine on table again.png

Premium HD 10:55

Sissy get fucked by sex maschine on table again.png

XVideosRed 8 months ago

Bitch Moaning on Chair with Chastity Device on

Bitch Moaning on Chair with Chastity Device on

FapHouse 1 month ago

VOYEUR

Clips4sale 1 year ago

Sissy Training Dress Up

Sissy Training Dress Up

Clips4sale 7 months ago

Holy BALLS

ShemaleSin 3 months ago

Lucas Miiller Private Show

HD 2:00 / 15:14

Lucas Miiller Private Show

Flirt4Free 3 months ago

I was enjoying myself too much jumping on that huge dildo, not wearing a chastity and cumming three times in a row :D

I was enjoying myself too much jumping on that huge dildo, not wearing a chastity and cumming three times in a row :D

XVideos 3 months ago

using my magic wand to jizz thru my virginity cell

using my magic wand to jizz thru my virginity cell

TrannyGem 3 months ago

Sissy fuckdoll rectal instructing purity

Sissy fuckdoll rectal instructing purity

TrannyGem 3 months ago

Lucas Miiller Private Show

Lucas Miiller Private Show

Flirt4Free 3 months ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 3 months ago

Fucking Trans Woman in Chastity - Compilation 4

Fucking Trans Woman in Chastity - Compilation 4

xHamster 3 months ago

Foot Job Freedom

HD 0:10 / 13:00

Foot Job Freedom

LoyalFans 3 months ago

Sophia Loreen Party on Dec 18, 2025 - Part 2

4K 2:00 / 19:20

Sophia Loreen Party on Dec 18, 2025 - Part 2

Flirt4Free 3 months ago

Fucking Sexy Sissy in Chastity - Compilation 5

Fucking Sexy Sissy in Chastity - Compilation 5

xHamster 3 months ago

Mia Malkoa Private Show

Mia Malkoa Private Show

Flirt4Free 3 months ago

Sweet Chastity 2

Sweet Chastity 2

aShemaleTube 3 months ago

Fucking Big Ass Sissy in Chastity - Compilation 3

HD 0:39 / 20:10

Fucking Big Ass Sissy in Chastity - Compilation 3

FapHouse 3 months ago

Fucking Trans Woman in Chastity - Compilation 10

Fucking Trans Woman in Chastity - Compilation 10

FapHouse 3 months ago

crossdresser slut Clip 1

crossdresser slut Clip 1

xHamster 3 months ago

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 3

Hot Trans Woman in Chastity Fucked and Sucking - Compilation 3

xHamster 3 months ago

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