Chastity Videos - Trans (46,292)

Sweet Chastity 25 - Mara Jade

Sweet Chastity 25 - Mara Jade

aShemaleTube 2 weeks ago

Man-Sized fuck machine dildo knocking off locked in chastity

Man-Sized fuck machine dildo knocking off locked in chastity

SexTubeSpot 4 years ago

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

Handcuffed Kitty Rose Fucked in Caged for Great Facial Cumshot

xHamster 6 months ago

Chastity Christmas! Nasty tgirl hotty gets punished! Flogging! Mouthfuck! Assfuck!

Chastity Christmas! Nasty tgirl hotty gets punished! Flogging! Mouthfuck! Assfuck!

ShemaleSin 2 days ago

Streaching My Sissy Femboy Gimps piss fuck-hole n lock Her instantly Back Up

Streaching My Sissy Femboy Gimps piss fuck-hole n lock Her instantly Back Up

TrannyGem 1 year ago

Caged Femboy Brings Himself to Cum with a Magic Wand

Caged Femboy Brings Himself to Cum with a Magic Wand

xHamster 1 year ago

Cutie assistant public remote manage

Cutie assistant public remote manage

TrannyGem 4 years ago

Sissy femboy Raine fucked in flat chastity by Flare Wolfsbane - Teaser Video!

Sissy femboy Raine fucked in flat chastity by Flare Wolfsbane - Teaser Video!

xHamster 4 months ago

Femdom turning him into my femboy sissy slave comp #3 her sissification journey so far

Femdom turning him into my femboy sissy slave comp #3 her sissification journey so far

Pornzona 3 weeks ago

New Steel Urethra Chastity Cage

New Steel Urethra Chastity Cage

xHamster 9 months ago

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and Jenbydoll

53% HD 0:39 / 17:43

Trans Girls Share a Cock and Chastity Cage Huge Load of Cum Jessica Bloom and Jenbydoll

FapHouse 1 month ago

Independent Training No20 Exposure Walk with a chastity belt

Independent Training No20 Exposure Walk with a chastity belt

xHamster 1 month ago

T-Model nearly ejaculations but locks up instead

T-Model nearly ejaculations but locks up instead

TrannyGem 1 year ago

blonde girl with toys

blonde girl with toys

aShemaleTube 6 years ago

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 2

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 2

aShemaleTube 1 month ago

chastity t-girl itzel saenzanal4on1

chastity t-girl itzel saenzanal4on1

PornOne 3 years ago

trans beauty whore in chastity gets banged by machine and gapes - Ella Mox

trans beauty whore in chastity gets banged by machine and gapes - Ella Mox

ShemaleSin 1 month ago

Opening Up white sugary-sweet cornhole, uncovering my girly cootchie taint

Opening Up white sugary-sweet cornhole, uncovering my girly cootchie taint

TrannyGem 2 years ago

Sexy sissy slut nun in chastity celebrates her slutty mass, begging to be blessed with lots of BBC to serve

Sexy sissy slut nun in chastity celebrates her slutty mass, begging to be blessed with lots of BBC to serve

xHamster 4 weeks ago

Frisky night into the parking lot

Frisky night into the parking lot

xHamster 1 year ago

Femboy Enjoy II

Femboy Enjoy II

TrannyGem 6 years ago

TGIRLSHOOKUP - Locked in Chastity

TGIRLSHOOKUP - Locked in Chastity

IcePorn 1 month ago

I had to show him my secret ASSet...

I had to show him my secret ASSet...

aShemaleTube 1 year ago

Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged

Trans Anal Training Cumming Twice From Monster Dildo Hard And Caged

xHamster 1 week ago

GROOBYGIRLS - Red, Locked, Ready

GROOBYGIRLS - Red, Locked, Ready

Fapnado 5 months ago

COMPLETELY 80s XXX: Post Aerobics BJ From Shemale two Cum

COMPLETELY 80s XXX: Post Aerobics BJ From Shemale two Cum

ShemaleSin 3 weeks ago

Bareback anal with sissy in flat chastity cage (Caged sissy ass to mouth)

Bareback anal with sissy in flat chastity cage (Caged sissy ass to mouth)

TitsTVX 4 months ago

Chastity Femboy Teasing Cage With Wand

Chastity Femboy Teasing Cage With Wand

getTranny 3 years ago

Locked Femboy transsexual Screws her Booty with Glass Jock

Locked Femboy transsexual Screws her Booty with Glass Jock

ShemaleSin 1 week ago

hope youre ready to watch me fill my pussy and cum for you again cumming in my flat cage

hope youre ready to watch me fill my pussy and cum for you again cumming in my flat cage

aShemaleTube 11 months ago

Sissy in Chastity Filled with Two Beer Enemas, One at the Door

Sissy in Chastity Filled with Two Beer Enemas, One at the Door

xHamster 3 weeks ago

Pegging and Latex Glove Fisting Lustful Chastity Sissy with Massive Ebony Sex toy by Mistresse Mercer

Pegging and Latex Glove Fisting Lustful Chastity Sissy with Massive Ebony Sex toy by Mistresse Mercer

ShemaleSin 1 month ago

RedHead cums caged

RedHead cums caged

ShemaleSin 9 months ago

Trans Sissy Floozy disciplined by Mistresse Murmur compilation

Trans Sissy Floozy disciplined by Mistresse Murmur compilation

BigTitsLust 4 weeks ago

Sissy walk in public locked, plugged and ball-gagged

Sissy walk in public locked, plugged and ball-gagged

TrannyGem 1 year ago

onlyfans - rachael belle what do you think of this view while i ride a fuck machine porn video

onlyfans - rachael belle what do you think of this view while i ride a fuck machine porn video

TransDoe 11 months ago

drilling deep in that butthole of thirsty natalie with four huge dicks

drilling deep in that butthole of thirsty natalie with four huge dicks

PornOne 4 years ago

Feminized Shemale Gets Horny

Feminized Shemale Gets Horny

xHamster 3 years 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

PornBox 2 years ago

Riding and gaping

Riding and gaping

xHamster 1 month ago

”Hardcore ass fucking fisting MFF”

”Hardcore ass fucking fisting MFF”

ThePornstar 3 months ago

I was enjoying myself likewise much jumping on that biggest vibrator, not wearing a chastity and cumming 3 times in a row :D

I was enjoying myself likewise much jumping on that biggest vibrator, not wearing a chastity and cumming 3 times in a row :D

ShemaleSin 1 week ago

Orianna Dunn Private Show

45% HD 2:00 / 4:33

Orianna Dunn Private Show

Flirt4Free 2 years ago

How to wear a flat chastity cage

How to wear a flat chastity cage

xHamster 1 year ago

Freya Bliss Private Show

Freya Bliss Private Show

Flirt4Free 1 week ago

Femboy in Chastity Takes Knot (Full Version on Many Movies RyuuDemonQueen)

Femboy in Chastity Takes Knot (Full Version on Many Movies RyuuDemonQueen)

Amateur8 12 hours ago

Chastity Slut In Stockings And Heels Playing

Chastity Slut In Stockings And Heels Playing

PornUse 3 months ago

Colegiala sissy putita jugando con su culo, Dios amo verme sexy

Colegiala sissy putita jugando con su culo, Dios amo verme sexy

WebcamBros 4 weeks ago

When You Fuck Me Just Right There Will Be Signs...

When You Fuck Me Just Right There Will Be Signs...

XVideos 1 week ago

Nadalinda- anal training with my biggest toy

Nadalinda- anal training with my biggest toy

xHamster 2 months ago

Amy - Sissy Splitscreen Chastity Masturbation Compilation 2

Amy - Sissy Splitscreen Chastity Masturbation Compilation 2

aShemaleTube 4 months ago

Sissy Hard-On Breezy in Innocence Pummels Self Before Jizm Shot

Sissy Hard-On Breezy in Innocence Pummels Self Before Jizm Shot

TrannyGem 8 months ago

Sophia Loreen Party on Dec 29, 2025 - Part 2

4K 2:00 / 33:01

Sophia Loreen Party on Dec 29, 2025 - Part 2

Flirt4Free 2 weeks ago

sissyjoyce - mistress laura plays with me

sissyjoyce - mistress laura plays with me

TransDoe 1 year ago

Kinky Kigarumi Chastity

Kinky Kigarumi Chastity

aShemaleTube 4 years ago

Freya Bliss Party on Jan 13, 2026 - Part 3

HD 2:00 / 25:53

Freya Bliss Party on Jan 13, 2026 - Part 3

Flirt4Free 18 hours ago

Daniela Lei chastity caged on fuck machine

Daniela Lei chastity caged on fuck machine

TrannyGem 1 month ago

Mature Slut Andreina

66% HD 0:39 / 3:36

Mature Slut Andreina

FapHouse 2 years ago

'I'm So Close!' She Doesn't Even Realise She's Jism

'I'm So Close!' She Doesn't Even Realise She's Jism

TrannyGem 1 year ago

you like seeing my squirt out of a tiny cage 💦

you like seeing my squirt out of a tiny cage 💦

aShemaleTube 5 months ago

Sissy training: supah-bi-atch in v-card having fun on hefty assfuck toys, multiple sissygasms

Sissy training: supah-bi-atch in v-card having fun on hefty assfuck toys, multiple sissygasms

Transvids.tv 1 year ago

So Strongly Fucked That I Was Wet Myself

So Strongly Fucked That I Was Wet Myself

xHamster 3 months ago

Outdoor exhibition day for a sissy, sex in her chastity cage

Outdoor exhibition day for a sissy, sex in her chastity cage

xHamster 2 years ago

Sissy in G-Cable and V-Card Boinked Stiff

Sissy in G-Cable and V-Card Boinked Stiff

TrannyGem 3 years ago

Fufu pin. Feminization. Sissification.

Fufu pin. Feminization. Sissification.

TrannyGem 1 year ago

Let yourself be fucked for your mistress, you horny sissy slut. Cum everywhere

Let yourself be fucked for your mistress, you horny sissy slut. Cum everywhere

Juicexxx 1 month ago

Asian Femboy Cumshot Eating

Asian Femboy Cumshot Eating

FapHouse 1 week ago

Twunk stuff both his crevasses with fake-sausages

Twunk stuff both his crevasses with fake-sausages

GayDudesFucking 2 weeks ago

emma rose derek kage ever wondered what happens when a cute transgirl gets a little wild porn video

emma rose derek kage ever wondered what happens when a cute transgirl gets a little wild porn video

TransDoe 1 year ago

She inspires me to be more a sissy cock cum chastity slut

She inspires me to be more a sissy cock cum chastity slut

aShemaleTube 6 months ago

Hot braceface is dildofucking herself while in chastity - Alexandra Braces Star is amazing!

Hot braceface is dildofucking herself while in chastity - Alexandra Braces Star is amazing!

xHamster 1 week ago

Skinny femboy in chastity fuck BBC

Skinny femboy in chastity fuck BBC

xHamster 9 months ago

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 5

Extraordinary Natural Tits Tgirl with a chastity cage Chapter 5

aShemaleTube 5 days ago

Outdoor chastity TS fisted

Outdoor chastity TS fisted

Eporner 1 year ago

Sissy Slaved Dominated by Two Mistresses

Sissy Slaved Dominated by Two Mistresses

Fetishpapa 8 years ago

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

Sissy Purity Marionette Taunted and Abased by Domme, Denied and Locked in the Vice

TrannyGem 5 years ago

Size queen femboy riding XXL tongue with belly bulge! (FemboyRaine)

Size queen femboy riding XXL tongue with belly bulge! (FemboyRaine)

xHamster 2 months ago

Good-Sized sissygasm compilation two

Good-Sized sissygasm compilation two

TrannyGem 2 years ago

Hotel Hookups VOL 1

HD 0:10 / 22:22

Hotel Hookups VOL 1

LoyalFans 4 days ago

Asian sissy public masturbation

Asian sissy public masturbation

Eporner 3 months ago

Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

57% HD 1:01 / 24:06

Mistress Baton’s Sissy Finishing School Guest Starring Mistress Vixen: Sissy Caning & BJ Training

FapHouse 1 month ago

Sweet Chastity 19

Sweet Chastity 19

aShemaleTube 2 weeks ago

riding my BBC dildo today, doing this never gets old for me 😅

riding my BBC dildo today, doing this never gets old for me 😅

aShemaleTube 11 months ago

Princess Sahara Taunting & Outrageous Her Trans Hoe

Princess Sahara Taunting & Outrageous Her Trans Hoe

TrannyGem 1 month ago

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

Anime Uniform Femboy Jizzing in Purity Cell ~Oscar20xxx~

GayCK 4 years ago

Sissy riding daddies dick 3

Sissy riding daddies dick 3

GayCK 2 years ago

Tiny Sissy Cock

Tiny Sissy Cock

aShemaleTube 1 year ago

onlyfans - maddie @maddietwt transgirl streaming video

onlyfans - maddie @maddietwt transgirl streaming video

TransDoe 2 years ago

Sissy bitch in sexy lingerie and chastity belt rides a big dildo and fucks her asshole with her fingers

Sissy bitch in sexy lingerie and chastity belt rides a big dildo and fucks her asshole with her fingers

xHamster 2 weeks ago

Two sissy sluts rubbing baby oil while caged and teasing in cute cheetah outfits!

Two sissy sluts rubbing baby oil while caged and teasing in cute cheetah outfits!

xHamster 2 years ago

Bi Encouragement for secret sissy - FemDom

Bi Encouragement for secret sissy - FemDom

xHamster 2 months ago

Chastity femboy beats balls and booty

Chastity femboy beats balls and booty

ShemaleSin 1 week ago

Transgirl in Chastity Humps Her Pillows

Transgirl in Chastity Humps Her Pillows

BigTitsLust 3 days ago

”Chastity Lynn gets her wet cunt fingered & licked”

”Chastity Lynn gets her wet cunt fingered & licked”

ThePornstar 1 year ago

fansly - jennifer lunden and thedongkinger mature sissy in chastity humiliated and trained by bbc

fansly - jennifer lunden and thedongkinger mature sissy in chastity humiliated and trained by bbc

TransDoe 1 year ago

POV: You are fucking me!!

POV: You are fucking me!!

xHamster 1 month ago

[SISSY] I took off my clothes by the river.

[SISSY] I took off my clothes by the river.

TrannyGem 1 year ago

Chastity Caged No Hand Cum Compilation

Chastity Caged No Hand Cum Compilation

getTranny 2 years ago

Tgirl Diversity Itsol faps dressed in fufu pin

Tgirl Diversity Itsol faps dressed in fufu pin

TrannyGem 10 months ago

LOCKTOBER DAY 31 RELEASE DAY

LOCKTOBER DAY 31 RELEASE DAY

xHamster 1 year ago

Maid costume, using a vibrator on my chastity cage until I squirt

Maid costume, using a vibrator on my chastity cage until I squirt

aShemaleTube 10 months ago

Cute Brunette Tranny Rides A Dildo

Cute Brunette Tranny Rides A Dildo

XGroovy 6 months ago

Sissy slut in chastity

Sissy slut in chastity

Eporner 5 years ago

Slave and servant for mistress soul and mind

Slave and servant for mistress soul and mind

FapCat 1 week ago

Working from home as a Chastity Sissy Secretary is so much pleasure

Working from home as a Chastity Sissy Secretary is so much pleasure

SortPorn 4 years ago

Spandex Gimpette Nail Machine Madness

Spandex Gimpette Nail Machine Madness

TrannyGem 3 years ago

Sissy Scarlet Sky Sucks Mal's Big Cock

Sissy Scarlet Sky Sucks Mal's Big Cock

BeMyHole 3 years ago

Sarah and Lucy Feminize You and Breezy You Out

Sarah and Lucy Feminize You and Breezy You Out

TrannyGem 2 years ago

Daniela Lei caged clit red lingerie solo

Daniela Lei caged clit red lingerie solo

aShemaleTube 1 month ago

Latex Sissy Anal Chastity Discipline by Headmistress Mercer

Latex Sissy Anal Chastity Discipline by Headmistress Mercer

ShemaleSin 1 month ago

Caged Sissy Rides

Caged Sissy Rides

aShemaleTube 10 months ago

Peed in my real sewing stockings and wear an electric cage

Peed in my real sewing stockings and wear an electric cage

xHamster 11 months ago

Treadmill Trussed Emo Sissy in Ache over Inflatable Ass Buttplug and V-Card Box

Treadmill Trussed Emo Sissy in Ache over Inflatable Ass Buttplug and V-Card Box

TrannyGem 1 year ago

Chastity cage change suprize oral pleasure!

Chastity cage change suprize oral pleasure!

ShemaleSin 1 year ago

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

Femdom Real Pair female domination pegging & ding-dong mastix & sissy cuck feminization FULL clip

SortPorn 1 year ago

Sexy tgirl in bodysuit gets fucked by fuckmachine and cums

Sexy tgirl in bodysuit gets fucked by fuckmachine and cums

xHamster 1 year ago

Sexy Blond Sissy Bimbo Style Doll

Sexy Blond Sissy Bimbo Style Doll

xHamster 1 year ago

Guy in a chastity gets pounded by an amazing tranny

Guy in a chastity gets pounded by an amazing tranny

Tranny.one 8 years ago

She Fucked Me with a Plug in her Ass

She Fucked Me with a Plug in her Ass

aShemaleTube 1 year ago

Fucking Sexy Sissy in Chastity - Compilation 8

Fucking Sexy Sissy in Chastity - Compilation 8

xHamster 2 months ago

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46,292 results found

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