Chastity Videos - Trans (48,648)

massive 3 story dildo fucking my big ass

massive 3 story dildo fucking my big ass

AnalVids 2 years ago

Blackate - Sissy in Hijab and Chastity Cage

Blackate - Sissy in Hijab and Chastity Cage

VipTube 1 year ago

Virginity Cell Challange - Day three/30

Virginity Cell Challange - Day three/30

Gayhub 11 months ago

Home Pegging

HD 1:01 / 20:01

FapHouse 1 month ago

jessyca 2 vs naponap 3

jessyca 2 vs naponap 3

aShemaleTube 1 year ago

peeing in my pants & drinking my own urinate during the time that in chastity

peeing in my pants & drinking my own urinate during the time that in chastity

ShemaleSin 4 years ago

Sissy Training by Queen Daralis Part 5

57% HD 0:39 / 4:59

Sissy Training by Queen Daralis Part 5

FapHouse 3 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 5 years ago

Trans Veternarian Natalie Carnot Gets The Puppy Boy Ready To Be Neutered with Femdom, Chastity

46% HD 0:10 / 13:03

Trans Veternarian Natalie Carnot Gets The Puppy Boy Ready To Be Neutered with Femdom, Chastity

LoyalFans 1 year ago

Clothespin Funbag Torment and Purity Sissy Ejaculation Denial with Lily Eden

Clothespin Funbag Torment and Purity Sissy Ejaculation Denial with Lily Eden

TrannyGem 1 year ago

Femboy Fat Ass Destroyed Swallows Whole Dildo Gushing Cum Ruin

Femboy Fat Ass Destroyed Swallows Whole Dildo Gushing Cum Ruin

JuicyTrans 3 weeks ago

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

HD 0:39 / 32:29

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

FapHouse 2 years ago

Locktober - 27 October urethral sounding play

Locktober - 27 October urethral sounding play

xHamster 2 years ago

Jude Getting Blowjob Course in Slaves Factory and Hard Ball Play from Mistress Madlen

Jude Getting Blowjob Course in Slaves Factory and Hard Ball Play from Mistress Madlen

xHamster 2 months ago

You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN

You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN

xHamster 2 years ago

video especial para o juninho - quer um video especial me chama

video especial para o juninho - quer um video especial me chama

PissVids 1 year ago

Femboy in Flat Chastity Uses Vibrator to Cum

Femboy in Flat Chastity Uses Vibrator to Cum

FapHouse 2 weeks ago

Tommy & Master Private Show

Tommy & Master Private Show

Flirt4Free 1 month ago

Transgirl in Chastity Humps Her Pillows

Transgirl in Chastity Humps Her Pillows

ShemaleSin 3 months ago

Sissy/feminization/humiliation

53% HD 0:39 / 14:30

Sissy/feminization/humiliation

FapHouse 4 years ago

Sissy Chayenne Dildo Training

Sissy Chayenne Dildo Training

xHamster 2 years ago

Lizzy Yum - Welcome home Lizzy- BDSM female chastity post op pussy masturbation orgasm

Lizzy Yum - Welcome home Lizzy- BDSM female chastity post op pussy masturbation orgasm

xHamster 2 years ago

Full Chasity Belt & Bra try on

Full Chasity Belt & Bra try on

xHamster 2 years ago

Total Sissy Amnesia

Total Sissy Amnesia

SortPorn 5 months ago

Latex Transgirl in Chastity Spanked, Teased, and Drilled by Femdom - OnlyFans @Ms_Nacke

Latex Transgirl in Chastity Spanked, Teased, and Drilled by Femdom - OnlyFans @Ms_Nacke

Amateur8 2 years ago

Interracial TS Bimbo Pegging & Face Fuck | MahoganyQen

HD 0:10 / 15:38

Interracial TS Bimbo Pegging & Face Fuck | MahoganyQen

LoyalFans 1 year ago

CD Sissy Play - Wank - Cums

CD Sissy Play - Wank - Cums

ShemaleSin 2 years ago

A Rewarding Morning Awakening: Blowjob, Fist, Pegging, Chastity Release and Handjob : Mistress Julia

A Rewarding Morning Awakening: Blowjob, Fist, Pegging, Chastity Release and Handjob : Mistress Julia

xHamster 1 year ago

Trans pair anal fisting compilation

Trans pair anal fisting compilation

ShemaleSin 8 months ago

Suck Dildo, Anal and Drink Own Cum

Suck Dildo, Anal and Drink Own Cum

xHamster 2 weeks ago

Crossdressing cosplay with ru-ka: chastity belt and anal masturbation

Crossdressing cosplay with ru-ka: chastity belt and anal masturbation

XXXShemalePorn 1 year ago

Wild & Sexy Shemale Experience: Big Shemales, Hot Sissies, & Stockings Chastity!

Wild & Sexy Shemale Experience: Big Shemales, Hot Sissies, & Stockings Chastity!

XXXShemalePorn 3 years ago

Saudi Shemale Arab Alia Alshammary Muslim Tranny Waria Hijra سكس عربي سعودي خليجي علياء الشمري شيميل عربي

Premium HD 1:55

Saudi Shemale Arab Alia Alshammary Muslim Tranny Waria Hijra سكس عربي سعودي خليجي علياء الشمري شيميل عربي

xnxxGold 3 months ago

Scott Carterr & Michael Magno Private Show

Scott Carterr & Michael Magno Private Show

Flirt4Free 2 years ago

Trans Gal Gets Screwed and Milked By Hung Bull

Trans Gal Gets Screwed and Milked By Hung Bull

ShemaleSin 2 months ago

”Black tranny Chastity Michaels fucks a guy”

”Black tranny Chastity Michaels fucks a guy”

TransHero 6 years ago

Ebony TS Chastity Michaels gets sucked and anal bangs a guy

Ebony TS Chastity Michaels gets sucked and anal bangs a guy

Sheshaft 12 years ago

BOBSTGIRLS: She's a Peachie!

BOBSTGIRLS: She's a Peachie!

xHamster 2 years ago

Sissy Slut Says Yes To Orally With A Dildo And Ruins Her Make-Up By Deepthroating

Sissy Slut Says Yes To Orally With A Dildo And Ruins Her Make-Up By Deepthroating

aShemaleTube 8 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 6 months ago

Caged sissy rides pink dildo with anal orgasms

Caged sissy rides pink dildo with anal orgasms

xHamster 1 year ago

Rectal examination with Tranny Doc Helena! The patient's ass has to take a lot!

Rectal examination with Tranny Doc Helena! The patient's ass has to take a lot!

xHamster 1 year ago

Femboys Fucking in New Apartment [part 1] Riding Cowgirl

65% HD 0:39 / 6:38

Femboys Fucking in New Apartment [part 1] Riding Cowgirl

FapHouse 1 year ago

Tgirl breezy wanks off in satin underpants pops all over

Tgirl breezy wanks off in satin underpants pops all over

TrannyGem 2 years ago

Kelli ball spanking

Kelli ball spanking

xHamster 4 years ago

Lily Starlet Frolicking with Underpants and Fake Penis getting Clitty Humid

Lily Starlet Frolicking with Underpants and Fake Penis getting Clitty Humid

TrannyGem 5 years ago

Sophia Loreen Party on Apr 23, 2026 - Part 3

HD 2:00 / 23:42

Sophia Loreen Party on Apr 23, 2026 - Part 3

Flirt4Free 1 week ago

First-Ever Time Railing Her Faux-Cock In A FuFu Clamp

First-Ever Time Railing Her Faux-Cock In A FuFu Clamp

TrannyGem 2 years ago

Dreaming of a big black

Dreaming of a big black

xHamster 1 year ago

FOOTJOB WITH MY HUBBY LIKE MY FEET IN NYLON NYLONS

FOOTJOB WITH MY HUBBY LIKE MY FEET IN NYLON NYLONS

ShemaleSin 4 years ago

GAVE MY SISSY A CHANCE TO CUM DURING HER CLEANING SHE'S BEEN SUCH A GOOD NYMPH

GAVE MY SISSY A CHANCE TO CUM DURING HER CLEANING SHE'S BEEN SUCH A GOOD NYMPH

TransTube.tv 1 year ago

TGirl Lucy wears glow in the dark chastity cage and is fucked by glowing blue dildo

TGirl Lucy wears glow in the dark chastity cage and is fucked by glowing blue dildo

xHamster 4 years ago

Maid CDAdalyn does more cleaning

Maid CDAdalyn does more cleaning

xHamster 2 years ago

Hot Shemale in a Hot live show

Hot Shemale in a Hot live show

aShemaleTube 7 years ago

Memorable moment from "Femboy Raine in flat chastity riding best friend Flare"

Memorable moment from "Femboy Raine in flat chastity riding best friend Flare"

xHamster 9 months ago

Shemale student cock tormented and anal fucked by dean

Shemale student cock tormented and anal fucked by dean

Eporner 1 year ago

Talking a little about sex and hookups with men - pegging

Talking a little about sex and hookups with men - pegging

xHamster 2 months ago

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Premature Handsfree Sissygasm - Jizz shot in 30 Seconds!

Gayhub 4 months ago

Footjob with Short White Ankle Socks

61% HD 2:00 / 7:51

Footjob with Short White Ankle Socks

Flirt4Free 4 years ago

Sissy femboy urinating in virginity cell with Emily Chick

Sissy femboy urinating in virginity cell with Emily Chick

TrannyGem 10 months ago

Sophia Loreen Private Show

HD 2:00 / 12:33

Sophia Loreen Private Show

Flirt4Free 2 weeks ago

Sissy Unlocks Her Chastity n Her Limber Clitty Bounces Around

Sissy Unlocks Her Chastity n Her Limber Clitty Bounces Around

ShemaleSin 4 years ago

Jepsen Rae Private Show

66% HD 2:00 / 14:02

Jepsen Rae Private Show

Flirt4Free 1 month ago

Shy teen sissy in chastity playing with BBC toy

Shy teen sissy in chastity playing with BBC toy

ShemaleSin 11 months ago

Jessica Bloom Riding Monster Dildos - Multiple Anal Orgasms In Chastity

Jessica Bloom Riding Monster Dildos - Multiple Anal Orgasms In Chastity

Pornzona 1 month ago

F Machine Alpha Pummels Sissy Arsehole - Jessica Bloom V-Card Ejaculation And Jizz In Throat

F Machine Alpha Pummels Sissy Arsehole - Jessica Bloom V-Card Ejaculation And Jizz In Throat

TrannyGem 1 year ago

Natalie Mars In Chastity Gets Anal By BBC

Natalie Mars In Chastity Gets Anal By BBC

VipTube 2 months ago

Pink Leopard Femboy Anal Bitch Toilet Plug Gape Cum Ruin

Pink Leopard Femboy Anal Bitch Toilet Plug Gape Cum Ruin

JuicyTrans 1 month ago

Femboy Craves CBT Punishment

73% HD 0:10 / 8:18

Femboy Craves CBT Punishment

Clips4sale 4 years ago

Sissy Locked and Loaded with Cum

Sissy Locked and Loaded with Cum

xHamster 3 months ago

sam_cdsissy sissy crossdresser masturbating and cumming

sam_cdsissy sissy crossdresser masturbating and cumming

xHamster 3 months 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

drinking a mutt's bone like a mega-slut

drinking a mutt's bone like a mega-slut

TrannyGem 3 years ago

Kitty vs Bunny

Premium HD 45:10

Sheer 1 year ago

TS Dominated and Assfucked by Mistress - TS Bimbo Pet Training with Sasha de Sade

TS Dominated and Assfucked by Mistress - TS Bimbo Pet Training with Sasha de Sade

aShemaleTube 7 years ago

Sissy Outside and Inside BBC Dildo Play

Sissy Outside and Inside BBC Dildo Play

xHamster 10 months ago

Mitts Free-For-All Cuming in purity railing yam-sized rectal fuck stick, encaged sissygasm lots of spunk

Mitts Free-For-All Cuming in purity railing yam-sized rectal fuck stick, encaged sissygasm lots of spunk

TrannyGem 2 years ago

I'm sissy joyce and I ill tease u till u explode

I'm sissy joyce and I ill tease u till u explode

ShemaleSin 6 months ago

sissy whiteboi has a plapgasm watching BNWO porn with BBC

sissy whiteboi has a plapgasm watching BNWO porn with BBC

Clips4sale 1 year ago

2024.09.07 school sailor & swimsuit

2024.09.07 school sailor & swimsuit

xHamster 1 year ago

Sissy crossdresser puts her cute love button in chastity

Sissy crossdresser puts her cute love button in chastity

ShemaleSin 11 months ago

Hard anal fuck for tied up sissy whore

Hard anal fuck for tied up sissy whore

xHamster 2 years ago

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

Premium HD 17:38

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

XVideosRed 4 months ago

Locked Chastity Sissy Gushes Ruined Sissygasm Dripping Mess

Locked Chastity Sissy Gushes Ruined Sissygasm Dripping Mess

JuicyTrans 3 weeks ago

Sissy Girl Caresses Herself And Cums In A Chastity Belt

Sissy Girl Caresses Herself And Cums In A Chastity Belt

AbTranny 3 years ago

Submissive queenie sateen gives deepthroat and grabs drilled

Submissive queenie sateen gives deepthroat and grabs drilled

HugeDickz 1 year ago

This Is How My Wife's Lover Will Be Treated #044 Bisexual Fantasy Part 2 pegging

This Is How My Wife's Lover Will Be Treated #044 Bisexual Fantasy Part 2 pegging

xHamster 1 year ago

Kink play dripping in fetish

Kink play dripping in fetish

xHamster 3 months ago

sissy in a chastity belt rips her stockings and fucks herself on a sex machine

sissy in a chastity belt rips her stockings and fucks herself on a sex machine

xHamster 1 month ago

Molly & Ostin Moon Private Show

HD 2:00 / 20:29

Molly & Ostin Moon Private Show

Flirt4Free 3 years ago

Hot TS Kitty Lucia Maya Drips Cum in Chastity Whilst Screwing Her Booty Then Unlocks Cage & Cums Hard

Hot TS Kitty Lucia Maya Drips Cum in Chastity Whilst Screwing Her Booty Then Unlocks Cage & Cums Hard

ShemaleSin 2 years ago

Milking my unshaved PAWG prostate til my brain melts ????

Milking my unshaved PAWG prostate til my brain melts ????

ShemaleSin 1 year ago

Jhon & Derek & Chris Private Show

43% HD 2:00 / 32:48

Jhon & Derek & Chris Private Show

Flirt4Free 3 years ago

Jhordy & Maxx Private Show

52% HD 2:00 / 24:57

Jhordy & Maxx Private Show

Flirt4Free 8 months 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

Sissy slave Oksana shows piss, cucumber and orange show in video chat with her Master

Sissy slave Oksana shows piss, cucumber and orange show in video chat with her Master

xHamster 3 years ago

Railing Her Faux-Cock Makes Her Pinned Clitty Seep A Pile!

Railing Her Faux-Cock Makes Her Pinned Clitty Seep A Pile!

TrannyGem 2 years ago

Virginity Box Tutorial

Virginity Box Tutorial

TrannyGem 2 years ago

Sensual Teasing and Pillow Riding

60% HD 2:00 / 7:10

Sensual Teasing and Pillow Riding

Flirt4Free 2 years ago

Chastity Cutie Ass Nectar Creams: Yum! My Favorite Treat

Chastity Cutie Ass Nectar Creams: Yum! My Favorite Treat

xHamster 5 months ago

Sissy slut extreme butt blasting jizz completion

Sissy slut extreme butt blasting jizz completion

WebcamBros 5 months ago

Ema Devine Private Show

66% 4K 2:00 / 5:07

Ema Devine Private Show

Flirt4Free 10 months ago

Redhead shemale fucked hard

Redhead shemale fucked hard

aShemaleTube 2 years ago

Ball busting makes me FERAL

Ball busting makes me FERAL

TrannyGem 2 years ago

BBC vs Sissy dick comparison & oral pleasure - Dad abased me! @ Sasha_de_Sade on all websites

BBC vs Sissy dick comparison & oral pleasure - Dad abased me! @ Sasha_de_Sade on all websites

ShemaleSin 4 years ago

Practicing For An Next Guest Sex BI #949 She Wants Threesome With Trans

Practicing For An Next Guest Sex BI #949 She Wants Threesome With Trans

xHamster 1 year ago

Caged Tranny Charlotte November Bangs Herself with Glass and BBC Toys

Caged Tranny Charlotte November Bangs Herself with Glass and BBC Toys

ShemaleSin 2 months ago

Keisy Royce Private Show

HD 2:00 / 21:59

Keisy Royce Private Show

Flirt4Free 1 month ago

Sissy anal creampie

Sissy anal creampie

xHamster 3 years ago

Sophia Loreen Party on Apr 6, 2026 - Part 2

55% HD 2:00 / 27:06

Sophia Loreen Party on Apr 6, 2026 - Part 2

Flirt4Free 3 weeks ago

christmas trans top ria bentley trains caged sissy elf lola crystals

HD 0:30 / 27:36

christmas trans top ria bentley trains caged sissy elf lola crystals

PornBox 5 months ago

Trans woman has a little surprise

Trans woman has a little surprise

xHamster 3 years ago

TV Hure Monique - My new sissy uniform with tutu

TV Hure Monique - My new sissy uniform with tutu

xHamster 4 years ago

Permanent chastity pop rivet

Permanent chastity pop rivet

FapHouse 4 years ago

POV play with my chastity clitty

POV play with my chastity clitty

xHamster 2 years ago

sissys in chastity pmv

sissys in chastity pmv

PornOne 2 years ago

Melody Lane Chastity tipped into

Melody Lane Chastity tipped into

AbTranny 6 years ago

[SISSY] I got bare in the park in the daytime

[SISSY] I got bare in the park in the daytime

TrannyGem 8 months ago

Orianna Dunn Private Show

55% HD 2:00 / 4:47

Orianna Dunn Private Show

Flirt4Free 2 years ago

Sissycdmish - Quality Ass Fucking with My Limp Clitty

63% HD 1:01 / 20:57

Sissycdmish - Quality Ass Fucking with My Limp Clitty

FapHouse 3 weeks ago

41 42 43 44 45

48,648 results found

Related categories

Trans Domination Strap-On Trans Transvestite Crossdressing Sissy Trans Fucks Trans Feminization Trans Fucks Girl Hermaphrodite Chastity Cage Ladyboy Trans Fucks Guy Trans Trans Solo Femboy 18+ Tgirl Trans Big Cock Trans Post-Op Futanari Trans Compilation

Narrow your search

chastity cage chastity cum bbc chastity chastity bbc sissy chastity femboy chastity 18+ chastity fuck chastity anal chastity sissy cum in chastity trans chastity chastity orgasm permanent chastity natalie mars chastity flat chastity chastity compilation ella hollywood chastity asian chastity chastity belt chastity bondage

Categories Pornstars

Categories Pornstars

PornMD: A Porn Search Engine.

Parents

Pornmd.com uses the "Restricted To Adults" (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornmd.com. All rights reserved.

© 2026 Pornmd.com. All rights reserved.