Chastity Videos - Trans (22,838)

Mistress Mercer Sissy Chastity Slave Teased and Humiliated, Denied and Locked in The Vice

Mistress Mercer Sissy Chastity Slave Teased and Humiliated, Denied and Locked in The Vice

YouPorn Unknown

Cumming in chastity with vibrator

Cumming in chastity with vibrator

RedTube Unknown

Twink in chastity fucks his ass

Twink in chastity fucks his ass

YouPorn Unknown

Sissy Anna in Self Slavery - Anal, Suck, Spank & Nippleplay

Sissy Anna in Self Slavery - Anal, Suck, Spank & Nippleplay

ShemaleSin 9 months ago

Intensive Anal Training Session with Biggest Toys & POV Sissygasm - full vid on LayneLovee Manyvids!

Intensive Anal Training Session with Biggest Toys & POV Sissygasm - full vid on LayneLovee Manyvids!

ShemaleSin 9 months ago

Fucking My TIght Little Asshole Looks So Much Better in the Sun

Fucking My TIght Little Asshole Looks So Much Better in the Sun

xHamster 9 months ago

Heterosexual Jacket Restrain Bondage - Sissy Maid

Heterosexual Jacket Restrain Bondage - Sissy Maid

TrannyGem 9 months ago

Lovely Sissy Femboy - Ass-Fuck Yam-Sized Fuck Stick - internal cumshot - sissygasm - sissy ejaculation - palms free-for-all jism

Lovely Sissy Femboy - Ass-Fuck Yam-Sized Fuck Stick - internal cumshot - sissygasm - sissy ejaculation - palms free-for-all jism

TrannyGem 9 months ago

C4 Sexxroulette and Chastity Cage on the Balcony. Cumshot 4min35 [10au25] Vanessabitchx

C4 Sexxroulette and Chastity Cage on the Balcony. Cumshot 4min35 [10au25] Vanessabitchx

FapHouse 8 months ago

Latex Sissy vibrates in self bondage with chastity and breathplay

Latex Sissy vibrates in self bondage with chastity and breathplay

RedTube Unknown

Chastity Caged Sissy masturbating and cum whilst 7 inch toy unfathomable inside her booty

Chastity Caged Sissy masturbating and cum whilst 7 inch toy unfathomable inside her booty

ShemaleSin 9 months ago

Sissy Cuckold Sessions: Chastity Ruined Orgasms

Sissy Cuckold Sessions: Chastity Ruined Orgasms

YouPorn Unknown

Plastic shemale whore in chastity rides huge dildos

Plastic shemale whore in chastity rides huge dildos

RedTube Unknown

Femboy blowjob latex cosplay in chastity

Femboy blowjob latex cosplay in chastity

YouPorn Unknown

Sissy riding dildo with fake pussy on a tripod

Sissy riding dildo with fake pussy on a tripod

aShemaleTube 9 months ago

Fuzzy Sock Gag and Chastity Pegging Humiliation for Sissy with Anal Sock Stuffing by Mistress Mercer

Fuzzy Sock Gag and Chastity Pegging Humiliation for Sissy with Anal Sock Stuffing by Mistress Mercer

RedTube Unknown

Roxi Heart Chastity cage for Uncontrolled urges Shemale

Roxi Heart Chastity cage for Uncontrolled urges Shemale

YepTube 9 months ago

What It Is Like to Have a Sissy Girlfriend Pt3

What It Is Like to Have a Sissy Girlfriend Pt3

xHamster 9 months ago

What It Is Like to Have a Sissy Girlfriend Pt2

What It Is Like to Have a Sissy Girlfriend Pt2

xHamster 9 months ago

The Sissycdmish Situation Is Out of Control!

The Sissycdmish Situation Is Out of Control!

xHamster 9 months ago

T-Gal in chastity can't hold in creampie any longer...

T-Gal in chastity can't hold in creampie any longer...

ShemaleSin 9 months ago

chastity belt and sex machine

chastity belt and sex machine

xHamster 9 months ago

Helpless swedish sissy in chastity naked outdoors

Helpless swedish sissy in chastity naked outdoors

aShemaleTube 8 months ago

Spectacular moment from "Mexican Sissy Maid un chastity Cage"

Spectacular moment from "Mexican Sissy Maid un chastity Cage"

xHamster 9 months ago

i am LongLegsJessie

i am LongLegsJessie

xHamster 8 months ago

Showing Myself

xHamster 9 months ago

Key moment from "I Get Horny when i use Chastity cage."

Key moment from "I Get Horny when i use Chastity cage."

xHamster 8 months ago

Fucking Big Ass Sissy in Chastity - Compilation 6

Fucking Big Ass Sissy in Chastity - Compilation 6

FapHouse 8 months ago

Only Purity Climax - Milky Femboys 2025 (Shorties)

Only Purity Climax - Milky Femboys 2025 (Shorties)

Gayhub 8 months ago

Fucking Big Ass Sissy in Chastity - Compilation 6

HD 0:39 / 20:08

Fucking Big Ass Sissy in Chastity - Compilation 6

FapHouse 8 months ago

Sissy Lauren degraded and humiliated

Sissy Lauren degraded and humiliated

xHamster 8 months ago

Innocence Encaged At Bedtime

Innocence Encaged At Bedtime

TransTube.tv 8 months ago

Powerful moment from "Dominant big cock TGirl Lucy bareback fucking her chastity sub"

Powerful moment from "Dominant big cock TGirl Lucy bareback fucking her chastity sub"

xHamster 8 months ago

Trans Woman in Chastity Fucked Hard - Compilation 10

Trans Woman in Chastity Fucked Hard - Compilation 10

xHamster 8 months ago

Captivating moment from "chubby sissy harley quinn anal fuck"

Captivating moment from "chubby sissy harley quinn anal fuck"

xHamster 8 months ago

Fucking My Ass in Chastity

Fucking My Ass in Chastity

FapHouse 8 months ago

Key moment from "Sissy Doll Spreads Her Ass with a Monster can locked in Chastity"

Key moment from "Sissy Doll Spreads Her Ass with a Monster can locked in Chastity"

xHamster 8 months ago

Chastity slave get milked while licking trannys feet

Chastity slave get milked while licking trannys feet

xHamster 8 months ago

Slutty Sissy Vladasexytrans Crossdresser

Slutty Sissy Vladasexytrans Crossdresser

xHamster 8 months ago

Thrilling moment from "Having sissygasm with chastity cage"

Thrilling moment from "Having sissygasm with chastity cage"

xHamster 8 months ago

Fucking Big Ass Sissy in Chastity - Compilation 6

Fucking Big Ass Sissy in Chastity - Compilation 6

xHamster 8 months ago

Shiny Oiled-Up Trans Babe Takes Huge BBC Dildo in Chastity Cage and Pigtails

Shiny Oiled-Up Trans Babe Takes Huge BBC Dildo in Chastity Cage and Pigtails

aShemaleTube 8 months ago

PUNY TEENAGER SISSY CROSSDRESSER GAPES BUTT AND PLAYS WITH JIZZ 4k

PUNY TEENAGER SISSY CROSSDRESSER GAPES BUTT AND PLAYS WITH JIZZ 4k

TrannyGem 8 months ago

me pissing out my chastity cage

me pissing out my chastity cage

xHamster 9 months ago

Take off the Cage and Cum

Take off the Cage and Cum

FapHouse 8 months ago

Sissy trying to get off in her rosy nappy with a massager

Sissy trying to get off in her rosy nappy with a massager

TrannyGem 8 months ago

Andreina Sexy Tanned MILF

Andreina Sexy Tanned MILF

FapHouse 8 months ago

Multiple prostate orgasms in chastity Jessica Bloom the cum slut

HD 1:01 / 26:08

Multiple prostate orgasms in chastity Jessica Bloom the cum slut

FapHouse 3 years ago

Cute Femboy Teen Passionately Screwing Sextoy With Chastity Cage - Femboy Sissy

Cute Femboy Teen Passionately Screwing Sextoy With Chastity Cage - Femboy Sissy

ShemaleSin 1 year ago

Satin Sissy Maid Plugs Herself and Sucks Her Doll

66% 1:01 / 13:00

Satin Sissy Maid Plugs Herself and Sucks Her Doll

FapHouse 9 months ago

Asian Sissy Mastubate in Chastity and Cum

Asian Sissy Mastubate in Chastity and Cum

xHamster 9 months ago

Anal training in chastity like a good sissy slut

Anal training in chastity like a good sissy slut

aShemaleTube 8 months ago

Alisaxxxcamshot Masturbates Cock in Chastity Belt

Alisaxxxcamshot Masturbates Cock in Chastity Belt

xHamster 8 months ago

chun li cums caged

chun li cums caged

ShemaleSin 8 months ago

sissy instructing cd femboy locked in v-card by gf who is fake penis frolicking his assfucking boypussy

sissy instructing cd femboy locked in v-card by gf who is fake penis frolicking his assfucking boypussy

TrannyGem 8 months ago

Hot Trans Woman in Chastity Fucked and Sucking

Hot Trans Woman in Chastity Fucked and Sucking

xHamster 8 months ago

Transvesti First chastity cage

Transvesti First chastity cage

aShemaleTube 4 years ago

”BOBSTGIRLS: A Juicy Peachie”

”BOBSTGIRLS: A Juicy Peachie”

Rainblow 1 year ago

Trans Sow Loren Aprile Ass-fuck Dehumanization

Trans Sow Loren Aprile Ass-fuck Dehumanization

TransTube.tv 1 year ago

”Huge tits ebony TBabe anal fucks man”

”Huge tits ebony TBabe anal fucks man”

Trashreality 1 year ago

Anal Slut Squirts in Chastity with Fuck Machine

Anal Slut Squirts in Chastity with Fuck Machine

xHamster 1 year 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”

Rainblow 1 year ago

Locktober making my mind melt ????‍????

Locktober making my mind melt ????‍????

ShemaleSin 1 year ago

Double Orgasm in Chastity

Double Orgasm in Chastity

FapHouse 1 year ago

Sissy Slut Filling Her Pussy with Cum From Her Large Squirting Dildo.

Sissy Slut Filling Her Pussy with Cum From Her Large Squirting Dildo.

FapHouse 1 year ago

”Hot T-Babe picks up man off the street to suck & fuck”

”Hot T-Babe picks up man off the street to suck & fuck”

IFuckedYourGF 1 year ago

Hot Blonde Crosdresser Puts Trans Woman in Bondage

Hot Blonde Crosdresser Puts Trans Woman in Bondage

FapHouse 1 year ago

Sissykanisa Crossdresser Show How a Good Sissy Wear Panties and Take a Pee

55% 1:01 / 7:00

Sissykanisa Crossdresser Show How a Good Sissy Wear Panties and Take a Pee

FapHouse 1 year ago

Chastity Slut Anal Training - Jessica Bloom - DP and Multiple Cumshots

HD 1:01 / 32:29

Chastity Slut Anal Training - Jessica Bloom - DP and Multiple Cumshots

FapHouse 2 years ago

Femboy Playing with Purple Vibrator

Femboy Playing with Purple Vibrator

FapHouse 1 year ago

I Was Caged and My Ass Was Broken

HD 1:01 / 14:43

I Was Caged and My Ass Was Broken

FapHouse 1 year ago

Chastity Remove From Cock

Chastity Remove From Cock

FapHouse 2 years ago

This was my failed attempt at doing a hot video this morning owell there's still some nice toying in chastity and in my purple

This was my failed attempt at doing a hot video this morning owell there's still some nice toying in chastity and in my purple

FapHouse 3 years ago

Caged student girl

70% HD 1:01 / 24:25

Caged student girl

FapHouse 3 years ago

Hawt Tranny Riding Large Ebony Dick - Chastity Sissygasm

Hawt Tranny Riding Large Ebony Dick - Chastity Sissygasm

ShemaleSin 1 year ago

Sissy Jiangshi plays with dildo

Sissy Jiangshi plays with dildo

xHamster 1 year ago

Amateur crossdresser femboy sissy twink bathroom big ass caged cute boys showering in chastity dressing afterwards!

Amateur crossdresser femboy sissy twink bathroom big ass caged cute boys showering in chastity dressing afterwards!

ManPorn 1 year ago

Sissy double anal intrusion with massager and man sausage followed by a facefuck

Sissy double anal intrusion with massager and man sausage followed by a facefuck

TransTube.tv 1 year ago

Crossdresser gets machine fucked with XXL Monster Dildos #1

Crossdresser gets machine fucked with XXL Monster Dildos #1

xHamster 1 year ago

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free And Swallows Cum

AbTranny 1 year ago

”BLACK-TGIRLS: Chastity Kane Gives Love & Cheer”

”BLACK-TGIRLS: Chastity Kane Gives Love & Cheer”

IFuckedYourGF 1 year ago

Gudrun and Angie in chastity and pump plug games

Gudrun and Angie in chastity and pump plug games

aShemaleTube 5 years ago

Caged Sissy BBC Sextoy Masturbation

Caged Sissy BBC Sextoy Masturbation

ShemaleSin 1 year ago

Luxia_tv, submissive and with the chastity cage

Luxia_tv, submissive and with the chastity cage

xHamster 1 year ago

V-Card Sissy Superslut Teaching - Jessica Bloom Phat Assfucking Climax

V-Card Sissy Superslut Teaching - Jessica Bloom Phat Assfucking Climax

TrannyGem 1 year ago

Chastity Shemale Gets Gaped by Dildo Fucking Machine

Chastity Shemale Gets Gaped by Dildo Fucking Machine

xHamster 1 year ago

Yam-Sized Donk Tgirl Pummeled Rock-Hard By Fuck Stick Plumb Machine

Yam-Sized Donk Tgirl Pummeled Rock-Hard By Fuck Stick Plumb Machine

TrannyGem 1 year ago

Femboy teen chastity bondage and used

Femboy teen chastity bondage and used

TrannyGem 1 year ago

Transsexual in Chastity Screwed Doggy style

Transsexual in Chastity Screwed Doggy style

ShemaleSin 1 year ago

Trans with H cup jugs riding ginormous fake-weenie

Trans with H cup jugs riding ginormous fake-weenie

TransTube.tv 1 year ago

Сsenior trans maid jizzes rock hard from electro-vibrator

Сsenior trans maid jizzes rock hard from electro-vibrator

TransTube.tv 1 year ago

Femboy teen chastity bondage and used

Femboy teen chastity bondage and used

KeekAss 1 year ago

sissy piggy permitted inwards from its pig shed home to neat domme home angel Scarlett black

sissy piggy permitted inwards from its pig shed home to neat domme home angel Scarlett black

TrannyGem 1 year ago

Chastity Collared Sissy Slave Craves Cock

Chastity Collared Sissy Slave Craves Cock

GayCK 1 year ago

Puny sissy femboy drills her culo with v-card on

Puny sissy femboy drills her culo with v-card on

TransTube.tv 1 year ago

Will a prince come save me?

Will a prince come save me?

TrannyGem 1 year ago

Elastrator cock banding - locktober 2022 day 9 - 30min

Elastrator cock banding - locktober 2022 day 9 - 30min

SexTubeSpot 1 year ago

Brunette Shemale Dildo In Chastity Cage

Brunette Shemale Dildo In Chastity Cage

Eporner 1 year ago

”Mommy's Sissy Chastity Training #BratPerversions”

”Mommy's Sissy Chastity Training #BratPerversions”

Fapnow 2 years ago

Jamming my Dark-skinned-eye with Playthings • Flogged Splooge • Coffee Hooded June

Jamming my Dark-skinned-eye with Playthings • Flogged Splooge • Coffee Hooded June

TransTube.tv 1 year ago

Dani In Chastity For The First Time Riding A Dildo And

Dani In Chastity For The First Time Riding A Dildo And

Eporner 1 year ago

Sissy assfucking training and sissygasm in v-card_sc.9

Sissy assfucking training and sissygasm in v-card_sc.9

TransTube.tv 1 year ago

Chastity: 4 weeks of fun compilation

Chastity: 4 weeks of fun compilation

XXXShemalePorn 2 years ago

Hands Free Cuming in chastity riding large anal sex toy, caged sissygasm lots of cum

Hands Free Cuming in chastity riding large anal sex toy, caged sissygasm lots of cum

ShemaleSin 2 years ago

Sexy Trans Bailey Wilde Removes Chastity Then Jerks Off

Sexy Trans Bailey Wilde Removes Chastity Then Jerks Off

xHamster 2 years ago

Black busty tranny Chastity Michaels fucks a construction worker

Black busty tranny Chastity Michaels fucks a construction worker

BeMyHole 5 years ago

Sissy Crossdresser Lizzy Fucking in Chastity

Sissy Crossdresser Lizzy Fucking in Chastity

BeMyHole 5 years ago

Sissygasm with fake penis + rectal wand

Sissygasm with fake penis + rectal wand

TrannyGem 2 years ago

sissy Skylar plays with toys

sissy Skylar plays with toys

xHamster 2 years ago

Never mentioning age, girl, or babe in any situation

Never mentioning age, girl, or babe in any situation

XXXShemalePorn 2 years ago

Horny Sissy Michelle In Chastity Fuck BBC Dildo

Horny Sissy Michelle In Chastity Fuck BBC Dildo

AbTranny 6 years ago

Sexy Shemale Gets Fucked Hard By Dildo Fucking Machine

Sexy Shemale Gets Fucked Hard By Dildo Fucking Machine

xHamster 1 year ago

A biggest plug making my Bussy lose ????️????

A biggest plug making my Bussy lose ????️????

ShemaleSin 1 year ago

Shy Racoon is testing a fresh chastity cage

Shy Racoon is testing a fresh chastity cage

ShemaleSin 1 year ago

Sissy secretary plays with her fake penis in virginity

Sissy secretary plays with her fake penis in virginity

TransTube.tv 1 year ago

Sploog On Green

Sploog On Green

TrannyGem 1 year ago

Pigs mistresse merely allows pathetic pig to wash in CIF in its pigsty home girl Scarlett ebony

Pigs mistresse merely allows pathetic pig to wash in CIF in its pigsty home girl Scarlett ebony

ShemaleSin 1 year ago

Domina likes her piggy to emasculation neck corset its pouch and hurt them for her

Domina likes her piggy to emasculation neck corset its pouch and hurt them for her

TrannyGem 1 year ago

CD plugged & in chastity, puts on dress

CD plugged & in chastity, puts on dress

aShemaleTube 9 years ago

Lusty TS Chastity Michaels take turns ass fucking with stud

Lusty TS Chastity Michaels take turns ass fucking with stud

aShemaleTube 9 years ago

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