Chastity Videos - Trans (39,609)

Sissy CD in Innocence, Jerked Dry, Handsfree Sissygasms, Fat Fuck Sticks, Ginormous Dirt, Cleanup, Rainbow, Sto

Sissy CD in Innocence, Jerked Dry, Handsfree Sissygasms, Fat Fuck Sticks, Ginormous Dirt, Cleanup, Rainbow, Sto

TrannyGem 3 years ago

Christian & Nicco & Elvis Private Show

54% HD 2:00 / 5:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Nelly Gale Private Show

4K 2:00 / 10:26

Nelly Gale Private Show

Flirt4Free 6 days ago

just leat me - lizzy laynez ots723

72% 1:27 / 18:30

just leat me - lizzy laynez ots723

AnalVids 4 years ago

Cute Trap Solo In Small Pink Chastity

Cute Trap Solo In Small Pink Chastity

KeekAss 8 months ago

Mommy Holy - The Workload - a JOI story

Mommy Holy - The Workload - a JOI story

xHamster 11 months ago

femboy chastity dildo riding!!

femboy chastity dildo riding!!

aShemaleTube 1 year ago

Femboi Gets Bred

Femboi Gets Bred

GayCK 3 years ago

chupou o cu da novinha trans e depois comeu ela - luana prado

chupou o cu da novinha trans e depois comeu ela - luana prado

PornBox 2 weeks ago

He lost his chastity by getting drilled rock hard

He lost his chastity by getting drilled rock hard

TrannyGem 1 month ago

Sissy Intro at home and pleasuring BIG BLACK COCK Faux-cock two

Sissy Intro at home and pleasuring BIG BLACK COCK Faux-cock two

Gayhub 1 month ago

Nurse Helena is coming to visit! Immediate recovery with urine therapy and oral treatment!

Nurse Helena is coming to visit! Immediate recovery with urine therapy and oral treatment!

xHamster 8 months ago

Caged Sissygasm the right way to Cum

Caged Sissygasm the right way to Cum

TransTube.tv 11 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

Ladyboy in heels going outdoor and piss while walking in her favorite chastity cage

Ladyboy in heels going outdoor and piss while walking in her favorite chastity cage

xHamster 1 month ago

Thrusting anal plug in chastity having analgasms & sissygasms

Thrusting anal plug in chastity having analgasms & sissygasms

aShemaleTube 4 weeks ago

Actor’s Studio: A Sissy Caption TS story

Actor’s Studio: A Sissy Caption TS story

SortPorn 2 years ago

Sissy Whore Training 2

Sissy Whore Training 2

xHamster 4 months ago

Sexy Blonde Crossdresser in Chastity Fucked

Sexy Blonde Crossdresser in Chastity Fucked

xHamster 4 months ago

Maximum punishment for chaste loser slave: fuck rubber doll with cage!

Maximum punishment for chaste loser slave: fuck rubber doll with cage!

xHamster 5 months ago

Feelipe & Adara Private Show

66% HD 2:00 / 4:26

Feelipe & Adara Private Show

Flirt4Free 1 week ago

I want a big black

I want a big black

xHamster 11 months ago

Rubber Doll Drone Training For Master

Rubber Doll Drone Training For Master

xHamster 4 months ago

SissyCDMish - sissy slut with pink cage fucks her ass so good

SissyCDMish - sissy slut with pink cage fucks her ass so good

xHamster 1 month ago

Time for Locktober|ASMR [Feminization] [Chastity] | Hentai Audio Roleplay

Time for Locktober|ASMR [Feminization] [Chastity] | Hentai Audio Roleplay

XVideos 2 months ago

Sissygasm w Ava Venom

55% HD 0:10 / 8:51

Sissygasm w Ava Venom

LoyalFans 1 month ago

[Trans] The Karen Next Door!

[Trans] The Karen Next Door!

VRPorn 8 months ago

Sissy Kelli walks a hotel corridor wearing a penis gag

Sissy Kelli walks a hotel corridor wearing a penis gag

xHamster 6 months ago

Crossdresser riding large ebony sex-toy in chastity outdoors in the rain

Crossdresser riding large ebony sex-toy in chastity outdoors in the rain

BigTitsLust 22 hours ago

Chastity Cage on her PenisThai Ladyboy Threesome Fucked

Chastity Cage on her PenisThai Ladyboy Threesome Fucked

Eporner 3 years ago

Tranny Gets Cock Bondaged And Ass Banged

Tranny Gets Cock Bondaged And Ass Banged

aShemaleTube 11 years 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 4 months ago

Sissy training her ass with big dildo

Sissy training her ass with big dildo

xHamster 3 months ago

Ta nouvelle sexualité comme Sissy : EP5 Transformer un Branleur en Esclave - Maitresse Julia Female Dominance

Ta nouvelle sexualité comme Sissy : EP5 Transformer un Branleur en Esclave - Maitresse Julia Female Dominance

TrannyGem 5 months ago

SissyCDMish - Observe me cork my caboose while I webcam tramp

SissyCDMish - Observe me cork my caboose while I webcam tramp

TrannyGem 6 months ago

Young Trans Sissy Is Used Relentlessly

Young Trans Sissy Is Used Relentlessly

xHamster 1 month ago

Lisa and tranny Lucy anal training and chastity

Lisa and tranny Lucy anal training and chastity

ShemaleSin 3 years ago

Sissy Bree

ShemaleSin 1 week ago

Schlong Locked Short XXX

Schlong Locked Short XXX

ShemaleSin 18 hours ago

Taniax Get a Sissygasm

Taniax Get a Sissygasm

xHamster 2 months ago

Sissy crossdresser puts her cute clit in chastity

Sissy crossdresser puts her cute clit in chastity

xHamster 1 month ago

Sissy Maid Self Bondage Electro Punishment

Sissy Maid Self Bondage Electro Punishment

xHamster 2 years ago

Sissy crossdresser playing with toys

Sissy crossdresser playing with toys

xHamster 5 months ago

Chastity Femboy Public Buttplug Walk & Anal Orgasms in The Woods Multiple Cumshots

Chastity Femboy Public Buttplug Walk & Anal Orgasms in The Woods Multiple Cumshots

xHamster 11 months ago

sissy instructing

sissy instructing

TrannyGem 3 years ago

Luccas & Jhordy Private Show

Luccas & Jhordy Private Show

Flirt4Free 1 week ago

Worship our Big Cocks

Worship our Big Cocks

aShemaleTube 6 years ago

Sissy Fucked by BBC Locked in Chastity Cage

Sissy Fucked by BBC Locked in Chastity Cage

Eporner 7 months ago

Nyxi gets A latest V-card Box From Her Dad

Nyxi gets A latest V-card Box From Her Dad

Transvids.tv 5 months ago

Indian Sissy Locked in Chastity showing of in Local Train

Indian Sissy Locked in Chastity showing of in Local Train

xHamster 4 years ago

Pvc Anal Whore

xHamster 2 months ago

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

Uncovered CD Sissy Katie Does Live Showcase In Purity Cell

TrannyGem 2 months ago

I want to be the one who takes your ladyboy chastity

I want to be the one who takes your ladyboy chastity

TrannyGem 4 years ago

Tgirl plays valorant and penetrates her cock-squeezing butt hole

Tgirl plays valorant and penetrates her cock-squeezing butt hole

TrannyGem 1 year ago

Sweetie assistant public remote manage

Sweetie assistant public remote manage

TrannyGem 3 years ago

Sissy in v-card fellates & gets boinked

Sissy in v-card fellates & gets boinked

TransTube.tv 1 month ago

Just a short video of being banged in a flat cage and dripping from my clitty

Just a short video of being banged in a flat cage and dripping from my clitty

ShemaleSin 3 weeks ago

Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity

Sissy Maid in Armbinder and Ankle Cuffed to bed in Chastity

xHamster 1 year ago

Young Shemale Metal Bondage in Latex Stockings Tied Up

Young Shemale Metal Bondage in Latex Stockings Tied Up

BondageDen 1 week ago

Is vapid cell petite enough for this trans damsel?

Is vapid cell petite enough for this trans damsel?

TrannyGem 2 weeks ago

Crossdresser Orlandi480 Posing in Leopard Lingerie, Cock Cage, and Dildo Play

Crossdresser Orlandi480 Posing in Leopard Lingerie, Cock Cage, and Dildo Play

xHamster 3 months ago

Locktober 2023 Day 13 Chaturbate Stream

Locktober 2023 Day 13 Chaturbate Stream

ShemaleSin 1 year ago

Virginity Sissy Sissygasm

Virginity Sissy Sissygasm

TrannyGem 10 months ago

Feelipe & Adara Private Show

Feelipe & Adara Private Show

Flirt4Free 4 days ago

Trans woman spunking with just a vibing vibro

Trans woman spunking with just a vibing vibro

TrannyGem 4 weeks ago

Sophia Loreen Party on Jul 14, 2025 - Part 2

HD 2:00 / 1:22:09

Sophia Loreen Party on Jul 14, 2025 - Part 2

Flirt4Free 1 day ago

Sissy High heels fucked with BBC

Sissy High heels fucked with BBC

xHamster 1 month ago

Depraved Sissy Maid Shows Off

Depraved Sissy Maid Shows Off

xHamster 3 months ago

Crossdresser with giant speculum and toys

Crossdresser with giant speculum and toys

xHamster 2 years ago

More BBC Fucking for Caged Sissy

More BBC Fucking for Caged Sissy

aShemaleTube 2 years ago

Colombian Boys Private Show

Colombian Boys Private Show

Flirt4Free 1 week ago

Sissy in chastity and her 8" sextoy (erect) two/three

Sissy in chastity and her 8" sextoy (erect) two/three

Amateur8 1 month ago

Sissy in chastity and her 8" sex tool (erect) 1/three

Sissy in chastity and her 8" sex tool (erect) 1/three

Amateur8 1 month ago

Milky tranny in Chastity has Handsfree Sissygasm + Shows her Lactating Bazookas

Milky tranny in Chastity has Handsfree Sissygasm + Shows her Lactating Bazookas

ShemaleSin 12 hours ago

Fuzzy Sock Gag and Chastity Pegging Indignity for Sissy with Booty-ravage Sock Slamming by Dominatrix Mercer

Fuzzy Sock Gag and Chastity Pegging Indignity for Sissy with Booty-ravage Sock Slamming by Dominatrix Mercer

TransTube.tv 9 months ago

Ekaterina Jazmine Private Show

Ekaterina Jazmine Private Show

Flirt4Free 4 days ago

Sissy gaped by screw machine

Sissy gaped by screw machine

BigTitsLust 3 weeks ago

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

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

Kams.com 5 months ago

Sissy Pussy - PMV by PrimeBBC

Sissy Pussy - PMV by PrimeBBC

aShemaleTube 3 months ago

Horny tranny with big dick fuck her boyfriend ass

Horny tranny with big dick fuck her boyfriend ass

aShemaleTube 1 year ago

Ekaterina Jazmine Private Show

Ekaterina Jazmine Private Show

Flirt4Free 2 weeks ago

Teen whore TS Kitty in cage anal destroyed by her boss ActorFab

Teen whore TS Kitty in cage anal destroyed by her boss ActorFab

XVideos 3 months ago

Prison guards train your throat on duty/ Oral femdom joi

Prison guards train your throat on duty/ Oral femdom joi

XVideos 2 weeks ago

Sandy Nell Private Show

4K 2:00 / 21:10

Sandy Nell Private Show

Flirt4Free 2 days ago

VERY SEXY Blond Crossdresser in Chastity Screwed Doggy Style

VERY SEXY Blond Crossdresser in Chastity Screwed Doggy Style

ShemaleSin 1 year ago

Milla Booms Private Show

4K 2:00 / 3:09:12

Milla Booms Private Show

Flirt4Free 2 weeks ago

Cute sissy femboy public chastity

Cute sissy femboy public chastity

ShemaleSin 3 years ago

Sophia Loreen Party on Jun 19, 2025

4K 2:00 / 26:29

Sophia Loreen Party on Jun 19, 2025

Flirt4Free 3 weeks ago

Sexually excited femboy's edging and wearing a chastity cage. No climax allowed.

Sexually excited femboy's edging and wearing a chastity cage. No climax allowed.

ShemaleSin 2 months ago

Checking Locked Dick and Strapon

Checking Locked Dick and Strapon

xHamster 1 year ago

Sophia Loreen Private Show

HD 2:00 / 13:50

Sophia Loreen Private Show

Flirt4Free 1 day ago

Anal Bang Machine Compilation 6

Anal Bang Machine Compilation 6

ShemaleSin 1 year ago

Steaming compilation of sissy femboy cum-shots - Spunk compilation #01

Steaming compilation of sissy femboy cum-shots - Spunk compilation #01

TrannyGem 3 months ago

Tattooed busty shemale anal fucks man after a year in chastity

Tattooed busty shemale anal fucks man after a year in chastity

Eporner 11 months ago

Anal Training in Chastity

Anal Training in Chastity

TrannyGem 6 years ago

sissy aperture tutor ambersis each sissy have to see

sissy aperture tutor ambersis each sissy have to see

ShemaleSin 1 year ago

Ts Isabella likes sissy training for English Mistresses

Ts Isabella likes sissy training for English Mistresses

ShemaleSin 2 years ago

The sissy 4n4lyzer educate her asspussy to gape and groans like a little doxy

The sissy 4n4lyzer educate her asspussy to gape and groans like a little doxy

BigTitsLust 3 months ago

Knot Wench Depth Training Teaser

Knot Wench Depth Training Teaser

ShemaleSin 2 months ago

Alessia Viilla & Charlie Lenox Private Show

Alessia Viilla & Charlie Lenox Private Show

Flirt4Free 3 weeks ago

Sissy crossdresser in chastity bangs sex-toy and farts lube

Sissy crossdresser in chastity bangs sex-toy and farts lube

BigTitsLust 6 days ago

Riding massive sex toy locked in chastity

Riding massive sex toy locked in chastity

ShemaleSin 2 weeks ago

Sandy Nell Private Show

4K 2:00 / 15:55

Sandy Nell Private Show

Flirt4Free 1 week ago

Ada Stardust 2022-06-26 Chaturbate Load

Ada Stardust 2022-06-26 Chaturbate Load

Transvids.tv 10 months ago

Teased Trans Girl Chastity And Anal Play

Teased Trans Girl Chastity And Anal Play

BeMyHole 10 months ago

Trans hotty in chastity gets banged by a machine

Trans hotty in chastity gets banged by a machine

ShemaleSin 1 year ago

Alessia Viilla & Charlie Lenox Private Show

Alessia Viilla & Charlie Lenox Private Show

Flirt4Free 3 weeks ago

Christian & Nicco & Elvis Private Show

42% HD 2:00 / 19:28

Christian & Nicco & Elvis Private Show

Flirt4Free 1 year ago

Rebeccah Gibson Private Show

HD 2:00 / 23:07

Rebeccah Gibson Private Show

Flirt4Free 12 hours ago

Sissy gets sexy rubbing clitoris then rides ramrod with squirting handsfree climax

Sissy gets sexy rubbing clitoris then rides ramrod with squirting handsfree climax

ShemaleSin 1 week ago

Sissy in chastity and her 8" vibrator (erect) three/three

Sissy in chastity and her 8" vibrator (erect) three/three

SortPorn 4 weeks ago

Green Mesh Lingerie Riding A Dildo

Green Mesh Lingerie Riding A Dildo

xHamster 1 month ago

Sissy Intro and playing as street slut outside

Sissy Intro and playing as street slut outside

XVideos 2 weeks ago

Caged and Plugged CD Whore Jasmyne Teases in Ebony Latex Leggings

Caged and Plugged CD Whore Jasmyne Teases in Ebony Latex Leggings

ShemaleSin 2 months ago

Large anal sex tool crossdresser

Large anal sex tool crossdresser

SortPorn 4 weeks ago

Sissy puts on her latex and accessories

Sissy puts on her latex and accessories

xHamster 5 months ago

Mamou avec Loren Aprile soumission &eacute_carlate quand le cuir et la tension dansent sur une peau asservie ba 1.4

Mamou avec Loren Aprile soumission &eacute_carlate quand le cuir et la tension dansent sur une peau asservie ba 1.4

XVideos 3 weeks ago

squirt - Part 3

squirt - Part 3

Flirt4Free 1 week ago

Chastity Bimbo Talks Dirty and Rides Dildo

Chastity Bimbo Talks Dirty and Rides Dildo

XVideos 4 years ago

Oiled Sissy in Flat Chastity Riding Massive Dildos

Oiled Sissy in Flat Chastity Riding Massive Dildos

3Gayz 2 months ago

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