Chastity Videos - Trans (48,324)

Pretend Sissy Gone Too Far

75% HD 1:01 / 22:51

Pretend Sissy Gone Too Far

FapHouse 1 year ago

Sissy in Restrain Bondage Made to Jizm in Virginity

Sissy in Restrain Bondage Made to Jizm in Virginity

TrannyGem 2 years ago

Mistresse Mercer Bizarre Deepthroat Thong-on Fellatio Weenie Training for Sissy Chastity Whore

Mistresse Mercer Bizarre Deepthroat Thong-on Fellatio Weenie Training for Sissy Chastity Whore

ShemaleSin 5 years ago

Twin Game

xHamster 1 year ago

Desire Sweet Private Show

Desire Sweet Private Show

Flirt4Free 2 months ago

pau branco pra um rabo moreno

60% 0:30 / 46:00

pau branco pra um rabo moreno

PornBox 5 months ago

White cock, black cock - ass to mouth!

HD 0:10 / 12:37

White cock, black cock - ass to mouth!

LoyalFans 1 year ago

Sis-k Pinky Chinese Dress Ep1: Get Dress up

Sis-k Pinky Chinese Dress Ep1: Get Dress up

xHamster 2 years ago

The Ultimate Chastity Cage Review and Guide Video

63% HD 1:01 / 37:26

The Ultimate Chastity Cage Review and Guide Video

FapHouse 2 years ago

Chastity fox ninja cosplay and huge anal dildo destruction

Chastity fox ninja cosplay and huge anal dildo destruction

ShemaleSex 2 months ago

Taunting Her Lil' Encaged Pearl Till She Jizzes

Taunting Her Lil' Encaged Pearl Till She Jizzes

TrannyGem 1 year ago

sissy princess gets locked in chastity cage and destroys by bbc toy

sissy princess gets locked in chastity cage and destroys by bbc toy

xHamster 1 year ago

Cooking With Jessica Bloom - Thick Creampie And Marshmallows Mixed With Additional Cream!

Cooking With Jessica Bloom - Thick Creampie And Marshmallows Mixed With Additional Cream!

ShemaleSin 1 month 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

Crossdresser gets machine fucked with XXL Monster Dildos #5

Crossdresser gets machine fucked with XXL Monster Dildos #5

xHamster 1 year ago

Lanna & Nefertiti Private Show

60% HD 2:00 / 5:57

Lanna & Nefertiti Private Show

Flirt4Free 3 years ago

HFD-004 flat chastity anal dildo vibrator cum

HFD-004 flat chastity anal dildo vibrator cum

xHamster 1 year ago

Nailing my booty dressed in my purity box

Nailing my booty dressed in my purity box

TrannyGem 1 year ago

Sara & Elver Private Show

62% HD 2:00 / 7:37

Sara & Elver Private Show

Flirt4Free 4 months ago

Locked Clit cum

Locked Clit cum

xHamster 2 years ago

Memorable moment from "Penis Cage & Pegging for Submissive Husband #871 Fantasy Bisexual Threesome Part 1"

Memorable moment from "Penis Cage & Pegging for Submissive Husband #871 Fantasy Bisexual Threesome Part 1"

xHamster 8 months ago

Ela tentando d.o.r.m.i.r e eu cheio de tes&atilde_o, n&atilde_o deixei ela em paz enquanto eu n&atilde_o gozei v&aacute_rias vezes.

Premium HD 16:10

Ela tentando d.o.r.m.i.r e eu cheio de tes&atilde_o, n&atilde_o deixei ela em paz enquanto eu n&atilde_o gozei v&aacute_rias vezes.

XVideosRed 1 year ago

Nutting Over And Over From Buttfuck

Nutting Over And Over From Buttfuck

TrannyGem 2 months ago

I sucked his cook so good that he fucked me

I sucked his cook so good that he fucked me

aShemaleTube 2 years ago

Little Serving Sissy Wench

HD 0:39 / 10:38

Little Serving Sissy Wench

FapHouse 9 months ago

Sissy 80 day chastity cum

Sissy 80 day chastity cum

aShemaleTube 5 years ago

ABT250502 Sexy devil in chastity

ABT250502 Sexy devil in chastity

xHamster 11 months ago

sissy fettered up and left at side of road

sissy fettered up and left at side of road

TrannyGem 4 years ago

Sissy Chastity Cage Hardcore Anal Playplay

60% HD 1:01 / 23:02

Sissy Chastity Cage Hardcore Anal Playplay

FapHouse 1 year ago

your a plowing dummy an embarrassing sissy angel scarlett dark-hued

your a plowing dummy an embarrassing sissy angel scarlett dark-hued

TransTube.tv 1 year ago

Purity Box Challange - Day two/ten

Purity Box Challange - Day two/ten

Gayhub 8 months ago

JOKER'S XXX ENJOYMENT: Dirty Makeup Bang With Tranny Harley ABRIDGED

JOKER'S XXX ENJOYMENT: Dirty Makeup Bang With Tranny Harley ABRIDGED

Lesbian8 3 months ago

What it feels like to be a Sissy

What it feels like to be a Sissy

xHamster 3 years ago

Locked In V-Card Under My Pretty Rosy Sundress

Locked In V-Card Under My Pretty Rosy Sundress

TrannyGem 1 year ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 3 years ago

Real Sissy crossdresser cuckold slut fucking multiple big dildos in chastity cage!

Real Sissy crossdresser cuckold slut fucking multiple big dildos in chastity cage!

xHamster 2 years ago

Mistress destroys her sissy's ass with a huge dildo

Mistress destroys her sissy's ass with a huge dildo

Juicexxx 4 months ago

Vulturif experiences outdoor fun with buttplug and chastity cage

Vulturif experiences outdoor fun with buttplug and chastity cage

SexTubeSpot 2 years ago

Sissy on her back, feet in the air, fucked by fuck machine

Sissy on her back, feet in the air, fucked by fuck machine

xHamster 10 hours ago

TRANSEI COM NAMORADO DA MINHA AMIGA - LUANA PRADO

TRANSEI COM NAMORADO DA MINHA AMIGA - LUANA PRADO

XVideosRed 8 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 5 months ago

Tiny Sissy Dick

Tiny Sissy Dick

xHamster 5 months ago

Busted T-Girls, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Creampie, Cum in Mouth BTG117

Busted T-Girls, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Creampie, Cum in Mouth BTG117

xnxxGold 2 years ago

Sissy Bride Riding Her Doll

Sissy Bride Riding Her Doll

xHamster 8 months ago

Chastity release milking - Cruel tease & denial

HD 0:10 / 15:04

Chastity release milking - Cruel tease & denial

LoyalFans 3 months ago

College Angel Anal Sissy Multiple Chastity Cumshots Jessica Bloom

College Angel Anal Sissy Multiple Chastity Cumshots Jessica Bloom

ShemaleSin 1 year ago

Sissy Anal Wench Locked Down on Biggest Sex-toy One Bar Prison Fastened & Teased in Chastity Cage by Mistresse

Sissy Anal Wench Locked Down on Biggest Sex-toy One Bar Prison Fastened & Teased in Chastity Cage by Mistresse

ShemaleSin 5 months ago

Crash - CBT Sissy By HoloPMV

Crash - CBT Sissy By HoloPMV

aShemaleTube 2 months ago

Nicolle & Christian Private Show

48% HD 2:00 / 5:47

Nicolle & Christian Private Show

Flirt4Free 8 months ago

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

Chastity Sissy Floozy Training - Jessica Bloom Giant Anal Climax

ShemaleSin 1 year ago

Trans Teenie V-card Anal invasion 3some

Trans Teenie V-card Anal invasion 3some

Transvids.tv 9 months ago

AB016 - Mistress Abbykitty in chastity fuck sissy slave with strapon -cum and incontinence

AB016 - Mistress Abbykitty in chastity fuck sissy slave with strapon -cum and incontinence

aShemaleTube 6 years ago

Fuck Machine

xHamster 7 months ago

Stuffing My Tight Hole with Chastity's Massive Shecock

Stuffing My Tight Hole with Chastity's Massive Shecock

XXXShake 2 years ago

Rebeccah Gibson Private Show

HD 2:00 / 11:59

Rebeccah Gibson Private Show

Flirt4Free 1 year ago

Sissy with flat chastity and highheels is fucked hard

Sissy with flat chastity and highheels is fucked hard

xHamster 1 year ago

T-Model Large Fuck Stick Sploog and Sissygasm

T-Model Large Fuck Stick Sploog and Sissygasm

TrannyGem 1 year ago

Elix & Master & Aleex Private Show

59% HD 2:00 / 37:17

Elix & Master & Aleex Private Show

Flirt4Free 9 months ago

Competitive stocking and negative lock chastity belt

Competitive stocking and negative lock chastity belt

4Gay 8 months ago

BBC Fucking Machine Makes Sissy Cum Hard in Chastity!

BBC Fucking Machine Makes Sissy Cum Hard in Chastity!

xHamster 3 months ago

Nyxi Leon Modeling Lesson at the Sissy Institute

66% HD 0:39 / 1:53

Nyxi Leon Modeling Lesson at the Sissy Institute

FapHouse 1 year ago

Your New Life as a Sissy Slave - Episode 4 - I Turn a Compulsive Wanker Into a Slave - Maitresse Julia

65% HD 1:01 / 11:20

Your New Life as a Sissy Slave - Episode 4 - I Turn a Compulsive Wanker Into a Slave - Maitresse Julia

FapHouse 2 years ago

Sissy Jennifer's New Chastity Belt Drove Her Crazy

Sissy Jennifer's New Chastity Belt Drove Her Crazy

xHamster 10 months ago

Orianna Dunn Private Show

44% HD 2:00 / 6:57

Orianna Dunn Private Show

Flirt4Free 2 years ago

Sissigasm for a sensual trans girl in black lingerie

Sissigasm for a sensual trans girl in black lingerie

XGroovy 2 years ago

A💣French Trav BomBe does a StripTease in LiVE. chastity cage VaneSsaBiTCHx PariSCienneTrvProd91 CAM4

A💣French Trav BomBe does a StripTease in LiVE. chastity cage VaneSsaBiTCHx PariSCienneTrvProd91 CAM4

xHamster 8 months ago

hotel sex fantasy ft. shy guy blh

HD 0:29 / 20:44

hotel sex fantasy ft. shy guy blh

PornBox 1 month ago

”Submissive Artemis Faux whipped by t-girl Jessy Dubais heavy prick”

”Submissive Artemis Faux whipped by t-girl Jessy Dubais heavy prick”

429Men 1 month ago

Sissy climax in v-card belt on fuck stick for father

Sissy climax in v-card belt on fuck stick for father

TrannyGem 2 years ago

Korean Secretary With Chastity Fucks Her Anal With a Dildo

Korean Secretary With Chastity Fucks Her Anal With a Dildo

TransJizz 2 years ago

”Transgender in chastity punished & anal fucked”

”Transgender in chastity punished & anal fucked”

ThePornstar 1 year ago

Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post

Sissy Maid in Spiked Chastity Cage Cuffed to Bed Post

xHamster 2 years ago

Milk or Tea?

xHamster 4 months ago

Mike Ass Fucks Sissy Charlotte While She is Locked in EStim Chastity Cage

Mike Ass Fucks Sissy Charlotte While She is Locked in EStim Chastity Cage

xHamster 3 years ago

Shaft maniac tantalizes puffies while grubby instructing her plow mouth crevasse

Shaft maniac tantalizes puffies while grubby instructing her plow mouth crevasse

TrannyGem 1 year ago

Getting proper plowed by dom old man

Getting proper plowed by dom old man

SexTubeSpot 3 years ago

Sissy Wife Competition - Sasha de Sade and Jenny Flowers

Sissy Wife Competition - Sasha de Sade and Jenny Flowers

aShemaleTube 7 years ago

Massimo Lombardi Private Show

63% HD 2:00 / 16:44

Massimo Lombardi Private Show

Flirt4Free 1 year ago

Destroy My Asshole Huge Inflatable Anal Dildo Sissy Training - Full Video on LayneLovee Manyvids

Destroy My Asshole Huge Inflatable Anal Dildo Sissy Training - Full Video on LayneLovee Manyvids

xHamster 2 years ago

Pissing in Chastity Cage

65% HD 1:01 / 5:40

Pissing in Chastity Cage

FapHouse 1 year ago

Anal Fuck Sissygasm Practice

Anal Fuck Sissygasm Practice

xHamster 2 weeks ago

Cumpilation Jess Bloom Being a Slutty Doxy Cumming And Banging Cumshots 2025

Cumpilation Jess Bloom Being a Slutty Doxy Cumming And Banging Cumshots 2025

ShemaleSin 2 months ago

hottest pulverizing machine fuck-fest ever

hottest pulverizing machine fuck-fest ever

TrannyGem 2 years ago

Transgirl in Chastity Humps Her Pillows

65% HD 0:39 / 10:28

Transgirl in Chastity Humps Her Pillows

FapHouse 3 months ago

Small Dick Shemale Strip Tease Dance for Stepdaddy

Small Dick Shemale Strip Tease Dance for Stepdaddy

FapHouse 2 years ago

Sophia Loreen Private Show

HD 2:00 / 21:57

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Tiny Pink Sissy Trapped in Chastity Cage for Fetish Fun

Tiny Pink Sissy Trapped in Chastity Cage for Fetish Fun

XXXShake 3 years ago

Sissy Femme Sandy Anal Dildo Fuck, Ass Egg Birth and Taste Piss & Oinks

Sissy Femme Sandy Anal Dildo Fuck, Ass Egg Birth and Taste Piss & Oinks

xHamster 2 months ago

Sissy pegging sessions by DominaFire

Sissy pegging sessions by DominaFire

xHamster 2 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 years ago

Carrara chastity belt review

Carrara chastity belt review

xHamster 3 years ago

Femboy Jism Compliation

Femboy Jism Compliation

TrannyGem 1 year ago

Buttfuck have fun w fake-spunk-pumps in fishnets phat pop-shot

Buttfuck have fun w fake-spunk-pumps in fishnets phat pop-shot

TransTube.tv 1 year ago

Sissy maid Dee should be cleaning Mistress's play room but starts playing with her toys Clip 1

Sissy maid Dee should be cleaning Mistress's play room but starts playing with her toys Clip 1

xHamster 4 weeks ago

Sophia Loreen Private Show

51% HD 2:00 / 25:05

Sophia Loreen Private Show

Flirt4Free 1 year ago

Goth Trans Smokes and Bangs Her Hole

Goth Trans Smokes and Bangs Her Hole

TransTube.tv 1 year ago

ME CONTRATA UNA CHICA HETERO PARA SU PRIMERA VES CON UNA VERGA TRANS

Premium HD 18:18

ME CONTRATA UNA CHICA HETERO PARA SU PRIMERA VES CON UNA VERGA TRANS

xnxxGold 1 year ago

Fufu chastity clip

Fufu chastity clip

xHamster 6 months ago

MILF trans with big cock break fat ass of teen

Premium HD 25:19

MILF trans with big cock break fat ass of teen

XVideosRed 2 months ago

You&rsquo_ve gone too far, beta...There&rsquo_s no turning back, your manhood is gone, and you&rsquo_re nothing but a pretty little sissy now. Might as well embrace it and seal your fate !

Premium HD 34:28

You&rsquo_ve gone too far, beta...There&rsquo_s no turning back, your manhood is gone, and you&rsquo_re nothing but a pretty little sissy now. Might as well embrace it and seal your fate !

xnxxGold 1 year ago

Sissy Kanisa Caged and Plugged in Satin Dress

Sissy Kanisa Caged and Plugged in Satin Dress

xHamster 1 month ago

Trans Female Takes BIG BLACK COCK From Boink Machine ROCK HARD!!!! Encaged Boner Jism!!!!

Trans Female Takes BIG BLACK COCK From Boink Machine ROCK HARD!!!! Encaged Boner Jism!!!!

TrannyGem 8 months ago

Practicing with my husband how I would treat a girl for lesbian sex #099

Practicing with my husband how I would treat a girl for lesbian sex #099

xHamster 1 year ago

MINHA AMIGA ME PEDIU AJUDA COM O VIDEOGAME DELA , QUANDO PERCEBEMOS ESTAVAMOS TRANSANDO - EVEZZINI

Premium HD 15:11

MINHA AMIGA ME PEDIU AJUDA COM O VIDEOGAME DELA , QUANDO PERCEBEMOS ESTAVAMOS TRANSANDO - EVEZZINI

XVideosRed 1 week ago

Rebeccah Gibson Private Show

HD 2:00 / 14:47

Rebeccah Gibson Private Show

Flirt4Free 1 month ago

Jhordy & Maxx Private Show

48% HD 2:00 / 1:21:10

Jhordy & Maxx Private Show

Flirt4Free 8 months ago

Julieta Shayk Private Show

HD 2:00 / 11:10

Julieta Shayk Private Show

Flirt4Free 3 years ago

Crossdresser Slutty Slut Undresses for Visitors

Crossdresser Slutty Slut Undresses for Visitors

xHamster 2 months ago

Troy & Kiros Private Show

66% HD 2:00 / 8:38

Troy & Kiros Private Show

Flirt4Free 2 years ago

Christian & Nicco & Elvis Private Show

63% HD 2:00 / 4:40

Christian & Nicco & Elvis Private Show

Flirt4Free 2 years ago

transei com namorado da minha amiga - luana prado

61% 0:30 / 34:28

transei com namorado da minha amiga - luana prado

PornBox 8 months ago

Sissy String-on Spitroast in Chastity Pegged by Splendid doll dom Duo by Mistress Mercer

Sissy String-on Spitroast in Chastity Pegged by Splendid doll dom Duo by Mistress Mercer

TransTube.tv 1 year ago

Trans Audio Porn 2 - on Your Knees - I'm Your Mistress & You're Locked in Chastity

60% HD 0:39 / 9:18

Trans Audio Porn 2 - on Your Knees - I'm Your Mistress & You're Locked in Chastity

FapHouse 5 months ago

advance sissy fucking machine bbc sex rob piper

advance sissy fucking machine bbc sex rob piper

aShemaleTube 3 years ago

Sissy taniax, street slut exposure

Sissy taniax, street slut exposure

xHamster 10 months ago

crossdresser outside at the bus stop with sex in her chastity cage and plugged ass

crossdresser outside at the bus stop with sex in her chastity cage and plugged ass

xHamster 1 year ago

Trans Hotty Rides Vibrator in Chastity

Trans Hotty Rides Vibrator in Chastity

Dafreeporn 1 month ago

TRANSVESTITE IN ROSY INNOCENCE BELT IN SOLARIUM SUNBATHING IN PANTY Swimsuit Marks On Butt-Cheeks

TRANSVESTITE IN ROSY INNOCENCE BELT IN SOLARIUM SUNBATHING IN PANTY Swimsuit Marks On Butt-Cheeks

TrannyGem 4 years ago

CFNM whipping domina whips sub in amateur BDSM

CFNM whipping domina whips sub in amateur BDSM

Some.Porn 1 year ago

Sophia Loreen Party on Apr 17, 2026 - Part 3

HD 2:00 / 1:06:50

Sophia Loreen Party on Apr 17, 2026 - Part 3

Flirt4Free 6 days ago

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