Chastity Videos - Trans (47,557)

A Fun Video to Play Along with

A Fun Video to Play Along with

FapHouse 1 year ago

How to Put on A Chastity Device

How to Put on A Chastity Device

FapHouse 2 years ago

This was so humiliating @MistressMurmur gave me self facial training ????????

This was so humiliating @MistressMurmur gave me self facial training ????????

ShemaleSin 4 months 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 3 months ago

cutesyfemboy 12 inch dildo play onlyfans porn video

cutesyfemboy 12 inch dildo play onlyfans porn video

TransDoe 1 year ago

Hi I'm Linzy19

xHamster 2 years ago

Matt & Elvis & Aron Private Show

HD 2:00 / 13:25

Matt & Elvis & Aron Private Show

Flirt4Free 3 years ago

SisK locks her cock in transparent chastity device

SisK locks her cock in transparent chastity device

xHamster 3 years ago

Used by Mistress Susi with condom mask in chastity wmv

56% 0:11 / 8:35

Used by Mistress Susi with condom mask in chastity wmv

Clips4sale 3 years ago

Raver Sissy femboy in v-card pummels BIG BLACK COCK four Female Dom Princess while she licks dinner, harsh anal invasion biotch 4/5

Raver Sissy femboy in v-card pummels BIG BLACK COCK four Female Dom Princess while she licks dinner, harsh anal invasion biotch 4/5

TrannyGem 2 years 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 1 year ago

From Best-Friend to Key-holder

From Best-Friend to Key-holder

Clips4sale 2 years ago

FAGGOT SISSY BEING A PATHETIC DUMB WHORE PART 2

FAGGOT SISSY BEING A PATHETIC DUMB WHORE PART 2

xHamster 6 months ago

Chastity & Anal Training My Collared Slave Girl - Bondage, Denial & Strict Control! Ft. River Enza

63% HD 0:10 / 16:02

Chastity & Anal Training My Collared Slave Girl - Bondage, Denial & Strict Control! Ft. River Enza

LoyalFans 7 months ago

Emo smol femboy with a innocence box and the butt gaped

Emo smol femboy with a innocence box and the butt gaped

2BGay 7 months ago

Mommy Holy - Feminization - Time For Your First Chastity

Mommy Holy - Feminization - Time For Your First Chastity

xHamster 1 year ago

Sissy with pigtails ride big dildo

Sissy with pigtails ride big dildo

xHamster 5 months ago

Femboys Fucking in New Apartment [part 1] Riding Cowgirl

64% HD 1:01 / 6:38

Femboys Fucking in New Apartment [part 1] Riding Cowgirl

FapHouse 1 year ago

Locktober Day two: Who Says You Can't Have Joy?

Locktober Day two: Who Says You Can't Have Joy?

TrannyGem 3 years ago

Ebony parent instructed my caboose while my boner was locked @Sasha_de_Sade on Onlyfans

Ebony parent instructed my caboose while my boner was locked @Sasha_de_Sade on Onlyfans

Transvids.tv 9 months ago

Hot Blonde Sissy Bailey Wilde in Chastity Fucked Missionary

Hot Blonde Sissy Bailey Wilde in Chastity Fucked Missionary

xHamster 1 year ago

Sissy in chastity cage drinking two beers via anal

Sissy in chastity cage drinking two beers via anal

xHamster 1 year ago

rubber slave in chastity being fucked by fucking machine

rubber slave in chastity being fucked by fucking machine

xHamster 1 month ago

cum in chastity cage

cum in chastity cage

xHamster 1 year ago

Futa Public Humiliation At Restaurant - Ft Imilia Audley

HD 0:30 / 13:15

Futa Public Humiliation At Restaurant - Ft Imilia Audley

Clips4sale 5 months ago

isabelly ferreira, rosy pinheiro, fabi moranguinho e rafaella gabrielly

63% 0:30 / 15:58

isabelly ferreira, rosy pinheiro, fabi moranguinho e rafaella gabrielly

PornBox 2 months ago

”Trans Natalie Mars fisted & tightened by MILF Penny Barber”

”Trans Natalie Mars fisted & tightened by MILF Penny Barber”

LesbianBliss 1 month ago

Mommy Holy - JOI - Lock you in Chastity then Anal Milking

Mommy Holy - JOI - Lock you in Chastity then Anal Milking

xHamster 1 year ago

mamou avec loren aprile partie 2 frisson et tremblement avant une etreinte passionnee

HD 0:30 / 15:07

mamou avec loren aprile partie 2 frisson et tremblement avant une etreinte passionnee

AnalVids 8 months ago

Asian Sissy Crossdresser Milked

Asian Sissy Crossdresser Milked

xHamster 4 months ago

Charli Rides West

Charli Rides West

PornFreeNow 3 months ago

Sissy website previews - R..a..c..h..a..e..l B..e..l..l..e

Sissy website previews - R..a..c..h..a..e..l B..e..l..l..e

PornoXO 4 months ago

Crossdresser slut in yellow fishnet green miniskirt and black corsage opens his hole with big toys nipple pumps, chastity

Crossdresser slut in yellow fishnet green miniskirt and black corsage opens his hole with big toys nipple pumps, chastity

xHamster 2 years ago

Ass Fucking in Tiny Chastity

HD 0:39 / 18:43

Ass Fucking in Tiny Chastity

FapHouse 2 years ago

Estim Self Bondage Stocks Sissy Maid

Estim Self Bondage Stocks Sissy Maid

xHamster 1 year ago

Lanna & Nefertiti Private Show

57% HD 2:00 / 5:57

Lanna & Nefertiti Private Show

Flirt4Free 3 years ago

Sissy in pink Chastity, Locked

Sissy in pink Chastity, Locked

xHamster 2 years ago

Femme Sandy X Queen Elena: Messy Puppy Drenched in Golden Nectar, Drinks Served, Face Splash, & Floor Cleanup

Femme Sandy X Queen Elena: Messy Puppy Drenched in Golden Nectar, Drinks Served, Face Splash, & Floor Cleanup

xHamster 1 month ago

Shemale and Slave fucking by two Mistresses / Shemale und Sklaven Strapon fick von zwei Herrinnen

HD 0:10 / 10:07

Shemale and Slave fucking by two Mistresses / Shemale und Sklaven Strapon fick von zwei Herrinnen

LoyalFans 3 years ago

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

54% HD 1:01 / 16:50

A Boy in a Cage Trains His Boy Pussy for a Halloween Party to Get All the Dicks

FapHouse 1 year ago

Classy Sissy Bitch Exposed in Chastity, Plug and Sexy Lingerie

Classy Sissy Bitch Exposed in Chastity, Plug and Sexy Lingerie

FapHouse 2 years ago

Sissy in permanent chastity!?

Sissy in permanent chastity!?

GayCK 5 years ago

Anna May Fuck Machine 4

Anna May Fuck Machine 4

xHamster 5 months ago

Trans Bully Teases Crossdresser with Big Black Cocks

65% HD 1:01 / 11:25

Trans Bully Teases Crossdresser with Big Black Cocks

FapHouse 8 months ago

Anus gets pounded hard. Cd anal fuckmachine.

Anus gets pounded hard. Cd anal fuckmachine.

FapHouse 2 months ago

Aline Cum 6

xHamster 1 month ago

Jasmine Gets Her Ass Ravaged by Fuck Machine and Huge Toy

HD 0:39 / 18:38

Jasmine Gets Her Ass Ravaged by Fuck Machine and Huge Toy

FapHouse 1 week ago

2032 - the Bwno Future

2032 - the Bwno Future

xHamster 6 months ago

Luxia_tv, submissive and with the chastity cage

Luxia_tv, submissive and with the chastity cage

xHamster 1 year ago

CD Female Exhibition Roped on Turntable with Magic Massager

CD Female Exhibition Roped on Turntable with Magic Massager

TrannyGem 2 years ago

French maid selfbondage

French maid selfbondage

xHamster 1 year ago

LOCLED AND LUSTFUL PT 2 *HD 1080*

HD 0:10 / 10:18

LOCLED AND LUSTFUL PT 2 *HD 1080*

LoyalFans 3 years ago

Odd Inbetween Ice And Fire

Odd Inbetween Ice And Fire

TrannyGem 1 year ago

Lily Demure: Getting Ready for Stepdaddy to Fuck Me This Morning

76% HD 0:39 / 2:40

Lily Demure: Getting Ready for Stepdaddy to Fuck Me This Morning

FapHouse 1 year ago

The Feminization Room - Remy D gets caught and transformed by Princess Dandy and Megan Daw (shaving, makeup, feminization, sissy, chastity, crossdressing, double domination, pegging)

54% 0:30 / 58:28

The Feminization Room - Remy D gets caught and transformed by Princess Dandy and Megan Daw (shaving, makeup, feminization, sissy, chastity, crossdressing, double domination, pegging)

Clips4sale 1 year ago

Sissy in chastity melts her brain with a fuckmachine

Sissy in chastity melts her brain with a fuckmachine

aShemaleTube 4 months ago

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

63% HD 0:39 / 6:40

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

FapHouse 1 month ago

I make it for the first time with a cucumber anal 30CM

I make it for the first time with a cucumber anal 30CM

xHamster 1 month ago

horny small cock caged ladyboy fuck and piss

65% HD 0:30 / 12:01

horny small cock caged ladyboy fuck and piss

PissVids 11 months ago

Sissy Foot Slave Trampled in High Heel Then Licks up Cum Jessica Bloom & Polieana

HD 0:39 / 11:37

Sissy Foot Slave Trampled in High Heel Then Licks up Cum Jessica Bloom & Polieana

FapHouse 1 year ago

Ruin my Sissy Pussy - High Speed Fuck in Pantyhose and Heels FULL VID on LayneLovee Manyvids

Ruin my Sissy Pussy - High Speed Fuck in Pantyhose and Heels FULL VID on LayneLovee Manyvids

xHamster 1 year ago

Sissy Crossdresser Rides John Thomas Master POV Huge Fake tits

Sissy Crossdresser Rides John Thomas Master POV Huge Fake tits

xHamster 2 years ago

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

73% HD 1:01 / 18:03

Interactive: Chastity Challenge: Questions for a Slave - Maitresse Julia

FapHouse 1 year ago

Sissygasm in Flat Chastity Cage

Sissygasm in Flat Chastity Cage

FapHouse 1 year ago

Virginity Sissy Sissygasm

Virginity Sissy Sissygasm

TrannyGem 1 year ago

Cucetinha arrombada escorrendo e grelinho preso

Cucetinha arrombada escorrendo e grelinho preso

XVideos 5 years ago

Sissy hope riding dildo very horny until cum

Sissy hope riding dildo very horny until cum

xHamster 3 years ago

mamou avec loren aprile partie 2 frisson et tremblement avant une etreinte passionnee

HD 0:30 / 15:07

mamou avec loren aprile partie 2 frisson et tremblement avant une etreinte passionnee

PornBox 8 months ago

He so Wants to Cum, but His Hands and Head Are Shackled!

He so Wants to Cum, but His Hands and Head Are Shackled!

FapHouse 1 year ago

SISSY BATHROOM IN BLACK TIGHTS AND ROSY INNOCENCE BELT

SISSY BATHROOM IN BLACK TIGHTS AND ROSY INNOCENCE BELT

GayCK 4 years ago

Jhordy & Cody & Archie Private Show

56% HD 2:00 / 9:32

Jhordy & Cody & Archie Private Show

Flirt4Free 3 weeks ago

Ep1 Testing My New Sissy: Housework and Entertainment - Mistress Julia

Ep1 Testing My New Sissy: Housework and Entertainment - Mistress Julia

FapHouse 4 months ago

Tease sissy husband with vibrator

Tease sissy husband with vibrator

xHamster 2 years ago

Master & Ithan Private Show

41% HD 2:00 / 12:09

Master & Ithan Private Show

Flirt4Free 8 months ago

hot CD slut Tiffany Kitten wearing sexy lingerie, fucks her wet pussy ass with dildo and BBC dildo

hot CD slut Tiffany Kitten wearing sexy lingerie, fucks her wet pussy ass with dildo and BBC dildo

xHamster 4 months ago

Ultimate Innocence SISSYGASM COMPILATION - Premature Wrecked Climax Bevy July 2024

Ultimate Innocence SISSYGASM COMPILATION - Premature Wrecked Climax Bevy July 2024

TrannyGem 1 year ago

Intens caught in public

Intens caught in public

WebcamBros 3 months ago

tigresavip me apresentou o amigo dela, fizemos uma live quente e transamos muito! - alice hael

tigresavip me apresentou o amigo dela, fizemos uma live quente e transamos muito! - alice hael

AnalVids 1 week ago

Sexy sissy maid vladasexytrans

Sexy sissy maid vladasexytrans

XVideos 1 year ago

Flat Chastity, Black Mini

Flat Chastity, Black Mini

FapHouse 9 months ago

Cuckold in chastity cage fucks his wife

Cuckold in chastity cage fucks his wife

xHamster 6 months ago

Caged Sissy Unloads Hard Cock

Caged Sissy Unloads Hard Cock

xHamster 1 year ago

Pop-Shot Compilation

Pop-Shot Compilation

4Gay 1 year ago

Sissy maid for hire - Your first day

Sissy maid for hire - Your first day

Clips4sale 1 year ago

Femboy in chastity teased and tortured with toesock footjob

Femboy in chastity teased and tortured with toesock footjob

ShemaleSin 3 years ago

CUMpilation: V-Card Sissygasms, Demolished Ejaculations, & Crossdressing Popshots of a Desperate Sissy

CUMpilation: V-Card Sissygasms, Demolished Ejaculations, & Crossdressing Popshots of a Desperate Sissy

TrannyGem 3 years ago

Full Video Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks off to Big Black Cock

HD 0:39 / 18:35

Full Video Stupid Sissy in Halloween Costume and Chastity Cage Surrenders and Jerks off to Big Black Cock

FapHouse 4 months ago

Sissy stretches out hole with inflatable cumtube dildo

Sissy stretches out hole with inflatable cumtube dildo

xHamster 3 years ago

Making my sissy guy Spunk for being a excellent damsel!

Making my sissy guy Spunk for being a excellent damsel!

TrannyGem 2 years ago

With a chastity lock, femboy and sissy Crossdressing was fucked by a big black cock and cuming

With a chastity lock, femboy and sissy Crossdressing was fucked by a big black cock and cuming

xHamster 3 years ago

Mommy's Massive Monster Cock!!!!

63% HD 0:10 / 13:40

Mommy's Massive Monster Cock!!!!

LoyalFans 3 months ago

Sophia Loreen Party on Jan 14, 2026 - Part 3

4K 2:00 / 32:14

Sophia Loreen Party on Jan 14, 2026 - Part 3

Flirt4Free 1 month ago

Sissy Intro at home and pleasing BBC Dildo

Sissy Intro at home and pleasing BBC Dildo

xHamster 9 months ago

Sissy Merve Chastity DoggyStyle Fucked BBC Anal Cum BDSM Cum Last Tattoo Blonde Sexy Tgirl Femboy Stockings Hells Part 5

Sissy Merve Chastity DoggyStyle Fucked BBC Anal Cum BDSM Cum Last Tattoo Blonde Sexy Tgirl Femboy Stockings Hells Part 5

xHamster 4 months ago

Mistress Mercer wants Bimbo Dolly to find a keyholder

Mistress Mercer wants Bimbo Dolly to find a keyholder

LoyalFans 3 months ago

Cumpilation #twenty

Cumpilation #twenty

ShemaleSin 1 year ago

Caged supah-nice trans gal gets bred by bad dragon toy - POVish

Caged supah-nice trans gal gets bred by bad dragon toy - POVish

TransTube.tv 1 year ago

Sissy selfbondage tied in abandoned attic

Sissy selfbondage tied in abandoned attic

xHamster 7 months ago

Patric & Lian & Andres Private Show

HD 2:00 / 30:16

Patric & Lian & Andres Private Show

Flirt4Free 3 years ago

Lanas Weekly Anal Invasion Lesson

Lanas Weekly Anal Invasion Lesson

TrannyGem 4 years ago

Caged Sissy Slut Frustration Training

Caged Sissy Slut Frustration Training

aShemaleTube 3 months ago

Vladasexytrans anal play and big anal plug

Vladasexytrans anal play and big anal plug

xHamster 1 year ago

Sissysimran - update #54 - Small dick shemale pissing outdoor while in chastity cage and play with her limp little clitty - Oct 16, 2024

Sissysimran - update #54 - Small dick shemale pissing outdoor while in chastity cage and play with her limp little clitty - Oct 16, 2024

XVideos 1 year ago

Patric & Oliver Private Show

48% HD 2:00 / 7:39

Patric & Oliver Private Show

Flirt4Free 3 years ago

Chastised sissy Tgirl Lily Starlet Drips clitty baby batter thru her cell

Chastised sissy Tgirl Lily Starlet Drips clitty baby batter thru her cell

TrannyGem 3 years ago

Intens caught in public

Intens caught in public

Gayhub 7 months ago

Fetish Night in a Ship Cabin – I Tried My Biggest Toy

Fetish Night in a Ship Cabin – I Tried My Biggest Toy

aShemaleTube 21 hours ago

Archie Blossom Private Show

Archie Blossom Private Show

Flirt4Free 1 week ago

Twerk On My Chastity - PMV by HoloPMV

Twerk On My Chastity - PMV by HoloPMV

aShemaleTube 10 months ago

Working from Home is so much fun with a Sissy Secretary.

Working from Home is so much fun with a Sissy Secretary.

xHamster 5 years ago

Inescapable Self Bondage Steel Fiddle Sissy Maid in Chasity Gagged and Ballet Boots

Inescapable Self Bondage Steel Fiddle Sissy Maid in Chasity Gagged and Ballet Boots

xHamster 3 years ago

Chastity Fuckdoll 4 - Elizabelle

Premium HD 22:05

Chastity Fuckdoll 4 - Elizabelle

XVideosRed 7 months ago

shemale beautiful

shemale beautiful

XVideos 8 months ago

Anal Fingering

Flirt4Free 4 years ago

Viky & Master Private Show

57% HD 2:00 / 14:39

Viky & Master Private Show

Flirt4Free 7 months ago

sissy captions for sissies - big ass sissy slut

sissy captions for sissies - big ass sissy slut

AnalVids 2 years ago

Mamou with Rachelle Karol I Take a Pretty Submissive in Part 3

61% 1:01 / 12:12

Mamou with Rachelle Karol I Take a Pretty Submissive in Part 3

FapHouse 4 months ago

Cute Tgirl in Flat Chastity Clip Fucks Huge Dildo!

56% HD 1:01 / 6:02

Cute Tgirl in Flat Chastity Clip Fucks Huge Dildo!

FapHouse 2 years ago

Domina makes sissy from girlz professional gargle fake penis and then plows her rear end fashion

Domina makes sissy from girlz professional gargle fake penis and then plows her rear end fashion

TrannyGem 2 years ago

Turn Into My Dumb Bimbo Sissy - Lip - Sucking Asmr for Pretty Face Obsession Clip by Findom Goaldigger

Turn Into My Dumb Bimbo Sissy - Lip - Sucking Asmr for Pretty Face Obsession Clip by Findom Goaldigger

xHamster 4 months ago

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