Chastity Videos - Trans (38,720)

Turning My Boyfriend Into A Sissy Clip 1

Turning My Boyfriend Into A Sissy Clip 1

XHamster 3 months ago

jessyca 2 vs naponap 2

jessyca 2 vs naponap 2

AShemaleTube 1 year ago

Sissy Dee sucks and rides Lady Fee's big strapon as Lady Fee squeezes Sissy Dees cage and balls Clip 1

Sissy Dee sucks and rides Lady Fee's big strapon as Lady Fee squeezes Sissy Dees cage and balls Clip 1

XHamster 5 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 2 years ago

I am a Girl

XHamster 1 year ago

Chastity husband sissy crossdresser shows under the panties his closed dick and crystal anal plug in big ass

Chastity husband sissy crossdresser shows under the panties his closed dick and crystal anal plug in big ass

XHamster 1 year ago

Tranny Hooker Sex 144

Tranny Hooker Sex 144

AShemaleTube 3 years ago

Sissy riding dildo outside

Sissy riding dildo outside

XHamster 1 year ago

Trans Cutie groans as her nuts get boiled~

Trans Cutie groans as her nuts get boiled~

Amateur8 8 months ago

Extraordinary Natural Tits Tgirl with a chastity cage Part 1

Extraordinary Natural Tits Tgirl with a chastity cage Part 1

AShemaleTube 9 months ago

Sissy rosebud teaching

Sissy rosebud teaching

TrannyGem 4 years ago

A cute trans-woman with dark brown, video created by AI

A cute trans-woman with dark brown, video created by AI

Seduced 7 months ago

She's the reason I love being a sissy slut. Love her

She's the reason I love being a sissy slut. Love her

AShemaleTube 1 year ago

Sissy bride Violetta

Sissy bride Violetta

AShemaleTube 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

Stop! Feminine sissies do not jerk their cock - sissy training and feminization with Lady Julina

Stop! Feminine sissies do not jerk their cock - sissy training and feminization with Lady Julina

XHamster 3 years ago

AB2509 Locked three months Cute femboy cum in flashlight with e-plug

AB2509 Locked three months Cute femboy cum in flashlight with e-plug

XHamster 10 months ago

You Need to Get Circumcised! i Will Circumcise You!

You Need to Get Circumcised! i Will Circumcise You!

TrannyGem 1 year ago

Pantieboy taking long BC and fat BC dildo. Filling panties with cum.

Pantieboy taking long BC and fat BC dildo. Filling panties with cum.

XHamster 8 months ago

Pinkish Punk Maid in virginity part two ass fucking instructing

Pinkish Punk Maid in virginity part two ass fucking instructing

TrannyGem 5 years ago

Zorrita Sissy

XHamster 1 year ago

Femboy gamer in fem clothing rimmed and barebacked by twink

Femboy gamer in fem clothing rimmed and barebacked by twink

Some.Porn 2 years ago

Femboy Virginity Ejaculation Compilation (palms free-for-all)

Femboy Virginity Ejaculation Compilation (palms free-for-all)

TrannyGem 1 year ago

The Only Way A Sissy Should Be Instructed To Jizz

The Only Way A Sissy Should Be Instructed To Jizz

TrannyGem 2 years ago

Stella Locke Glasses Cute Ass Barebacking

Stella Locke Glasses Cute Ass Barebacking

AShemaleTube 6 years ago

Snowbunny Slave Halloween Costume

Snowbunny Slave Halloween Costume

XHamster 10 months ago

Sophia Loreen Private Show

57% 4K 2:00 / 4:22

Sophia Loreen Private Show

Camster 2 weeks ago

Sissy wearing breast pumps to learn to lactate part 1

Sissy wearing breast pumps to learn to lactate part 1

ShemaleSin 1 month ago

AB104 Sex toy tester surrender (English subtitles)

AB104 Sex toy tester surrender (English subtitles)

XHamster 2 years ago

Chastity estim cum for cute sissy

Chastity estim cum for cute sissy

ShemaleSin 4 years ago

Anna May - Sissygasam

Anna May - Sissygasam

XHamster 4 weeks ago

Sissy Merve Rose Chastity Belt Tattoo Blonde Sexy Tgirl Femboy Special Stockings Leopard Ride BBC Fucked Hard Catgirl Tranny

Sissy Merve Rose Chastity Belt Tattoo Blonde Sexy Tgirl Femboy Special Stockings Leopard Ride BBC Fucked Hard Catgirl Tranny

XHamster 10 months ago

onlyfans - bambifyme mreasydeck all the way erected porn video

onlyfans - bambifyme mreasydeck all the way erected porn video

TransDoe 1 year ago

Sissy Alexas makes ass pussy stretching exercises in chastity 2 of 2

Sissy Alexas makes ass pussy stretching exercises in chastity 2 of 2

XHamster 3 years ago

chastity sissy to cum by Mistresses

chastity sissy to cum by Mistresses

AbTranny 6 years ago

Sissy in Chastity Destroying her Asshole with Huge Butt Plug

Sissy in Chastity Destroying her Asshole with Huge Butt Plug

XHamster 3 years ago

Black TS Girl Chastity Michaels Gets Her Big Male stick Sucke

Black TS Girl Chastity Michaels Gets Her Big Male stick Sucke

Tranny.one 1 year ago

MaureenNadh - Hijab Asian Skinny Squirting On Chastity While Dildo Ride.

MaureenNadh - Hijab Asian Skinny Squirting On Chastity While Dildo Ride.

XHamster 3 years ago

Trans Angels Dick Sucking Triple Threat

Trans Angels Dick Sucking Triple Threat

ShemaleSin 9 months ago

Cumdump in my pussy onlyfans alexiakessel1 tribalchief313

Cumdump in my pussy onlyfans alexiakessel1 tribalchief313

XHamster 7 months ago

Sophia Loreen Party on Jul 23, 2026 - Part 3

HD 2:00 / 30:23

Sophia Loreen Party on Jul 23, 2026 - Part 3

Camster 1 month ago

Blonde Bimbo Sissy Rides Dildo Like a Good Little Slut

Blonde Bimbo Sissy Rides Dildo Like a Good Little Slut

XHamster 3 months ago

Sissy Slut Anal Warmup Routine - Getting Ready for Huge Cock FULL VID ON LAYNELOVEE MANYVIDS

Sissy Slut Anal Warmup Routine - Getting Ready for Huge Cock FULL VID ON LAYNELOVEE MANYVIDS

XHamster 2 years ago

Anabel Fiofilova Private Show

4K 2:00 / 11:22

Anabel Fiofilova Private Show

Camster 2 days ago

Sissy Slut are godess - Clip

Sissy Slut are godess - Clip

AShemaleTube 3 months ago

Desire Sweet Private Show

HD 2:00 / 23:51

Desire Sweet Private Show

Camster 1 week 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 1 year ago

sissy slut gets strapped

sissy slut gets strapped

PornBox 3 years ago

Chastity Angel Anal Creampie - Sabina Steele

Chastity Angel Anal Creampie - Sabina Steele

AbTranny 11 months ago

TVROSE CROSSDRESSER SHOWING PINK SISSY CHASTITY CAGE IN BLACK LACE DRESS, STOCKINGS AND FLUFFY WHITE HEELS

TVROSE CROSSDRESSER SHOWING PINK SISSY CHASTITY CAGE IN BLACK LACE DRESS, STOCKINGS AND FLUFFY WHITE HEELS

XHamster 2 years ago

Hailey Dame gets both her crevices destroyed by BIG BLACK COCK

Hailey Dame gets both her crevices destroyed by BIG BLACK COCK

TrannyGem 1 year ago

Slutty Shemale Rides Big Black Cock Sex Doll for Sissygasm

Slutty Shemale Rides Big Black Cock Sex Doll for Sissygasm

XHamster 1 year ago

Femboy Riding a Dildo. Locked in Chastity While Wearing Thigh High Socks

Femboy Riding a Dildo. Locked in Chastity While Wearing Thigh High Socks

XHamster 5 months ago

Sissy TGirl Scarlett Rides Her Toy While Locked in Chastity

Sissy TGirl Scarlett Rides Her Toy While Locked in Chastity

XHamster 6 years ago

2025.05.24 sport swimsuit cum in chastity

2025.05.24 sport swimsuit cum in chastity

XHamster 8 months ago

Crossdresser pubes strap catheter have fun

Crossdresser pubes strap catheter have fun

4Gay 1 year ago

Sissy very first vid

Sissy very first vid

TrannyGem 2 years ago

Last Year Lunch Drinking Pee Eating Cum CEI Video

Last Year Lunch Drinking Pee Eating Cum CEI Video

XHamster 7 months ago

Princess Sahara Taunting & Outrageous Her Trans Hoe

Princess Sahara Taunting & Outrageous Her Trans Hoe

TrannyGem 9 months ago

Man attempts to get delight while he is locked in a v-card box. Compilation

Man attempts to get delight while he is locked in a v-card box. Compilation

TrannyGem 1 year ago

Tgirl plays valorant and penetrates her cock-squeezing butt hole

Tgirl plays valorant and penetrates her cock-squeezing butt hole

TrannyGem 3 years ago

Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

Tantaly : An Unexpected Christmas Gift: A Sissy's Penetration - Mistress Julia

XHamster 1 year ago

Wait, Natasha, I Have an Order.

Wait, Natasha, I Have an Order.

XHamster 8 months ago

Sissy fur slut enjoying her toy

Sissy fur slut enjoying her toy

XHamster 1 year ago

Caged sissy having a good time outdoors

Caged sissy having a good time outdoors

XHamster 4 years ago

Sissy Schoolgurl Maddy Loves Drilling Her Ass With Big Toys And Going Ass To Mouth

Sissy Schoolgurl Maddy Loves Drilling Her Ass With Big Toys And Going Ass To Mouth

XHamster 6 months ago

Cute Tgirl Variety Itsol gets her big butt plugged & anal trained with a chastity cage

Cute Tgirl Variety Itsol gets her big butt plugged & anal trained with a chastity cage

TrannyMovs 11 months ago

sissy sonya on gynochair nailed by screwing machine

sissy sonya on gynochair nailed by screwing machine

TrannyGem 2 years ago

【汚デブ女装肉便器】ド変態★淫乱ダイジェスト【女装マゾ】【みけぽ】【GMPD】【精液便所】【性奴隷】【調教】【乳首ピアス】【露出】

【汚デブ女装肉便器】ド変態★淫乱ダイジェスト【女装マゾ】【みけぽ】【GMPD】【精液便所】【性奴隷】【調教】【乳首ピアス】【露出】

TrannyGem 2 years ago

minha vizinha trans safada quis ser minha submissa, fiz lamber ate as minhas botas! - evezzini

minha vizinha trans safada quis ser minha submissa, fiz lamber ate as minhas botas! - evezzini

PornBox 2 months ago

Mean domina tramples beta incel

Mean domina tramples beta incel

Some.Porn 1 year ago

Twin Game

XHamster 2 years ago

Hands-Free Orgasm mtf trans Zoe Jarvis 39 transgender

Hands-Free Orgasm mtf trans Zoe Jarvis 39 transgender

XHamster 2 months ago

Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere

Sexy sissy fisted while sliding a sounding rod deep in her chastity locked clit until squirting everywhere

XHamster 1 year ago

Nicolle & Christian Private Show

64% HD 2:00 / 8:54

Nicolle & Christian Private Show

Camster 1 year ago

Sissygasm with BBC dildo in pink dress

Sissygasm with BBC dildo in pink dress

XHamster 11 months ago

Sex Therapist London River

Sex Therapist London River

Dafreeporn 1 month ago

Tractable Sissy Receives Coarse Butt and Mouth Screwing From Large Shlong Trans Sweetheart

Tractable Sissy Receives Coarse Butt and Mouth Screwing From Large Shlong Trans Sweetheart

ShemaleSin 1 year ago

Plappies for fun: Locked Sissy ball-busting for the BNWO

Plappies for fun: Locked Sissy ball-busting for the BNWO

XHamster 1 month ago

”Tranny is pissing over her prolapped booty”

”Tranny is pissing over her prolapped booty”

ThePornstar 6 months ago

Sissy in a Hotel

Sissy in a Hotel

XHamster 3 years ago

How to put on a fufu pinch

How to put on a fufu pinch

TrannyGem 1 year ago

Sissy Juliette in chastity lockdown for 8h. kinky fun with toys all night at home

Sissy Juliette in chastity lockdown for 8h. kinky fun with toys all night at home

XHamster 1 year ago

outdoor motel risky slutwalk chastity boots

outdoor motel risky slutwalk chastity boots

AShemaleTube 2 months ago

Femdom POV: Sissy

Femdom POV: Sissy

XHamster 2 months ago

Scrambling Her Organs Till She Pops

Scrambling Her Organs Till She Pops

TrannyGem 2 years ago

”Tranny is pissing over her prolapped booty”

”Tranny is pissing over her prolapped booty”

IFuckedYourGF 6 months ago

V-Card Femboy Cunny! Humungous Pink Cigar made into Lil Cooch and Porked with Sounding Cock.

V-Card Femboy Cunny! Humungous Pink Cigar made into Lil Cooch and Porked with Sounding Cock.

TrannyGem 2 years ago

Pegging & Latex Glove Fisting Slutty Chastity Sissy With Giant Black Dildo By Mistress Mercer

Pegging & Latex Glove Fisting Slutty Chastity Sissy With Giant Black Dildo By Mistress Mercer

BeMyHole 5 months ago

Marian & Richard Private Show

HD 2:00 / 1:01:27

Marian & Richard Private Show

Camster 1 week ago

Trans Rachael Belle Experiences A Raunchy Awakening

Trans Rachael Belle Experiences A Raunchy Awakening

BigTitsLust 1 year ago

Thick sissy boy riding dildo and posing

Thick sissy boy riding dildo and posing

XHamster 1 month ago

tspov - kitty kisses we got it hot and she got all messed up porn video

tspov - kitty kisses we got it hot and she got all messed up porn video

TransDoe 1 year ago

Gothic sissy taniax plays with dildo in the public view-PART1

Gothic sissy taniax plays with dildo in the public view-PART1

XHamster 1 year ago

Femboy pet in super-cute socks plays with playthings and cascades jism ~Oscar20xxx~

Femboy pet in super-cute socks plays with playthings and cascades jism ~Oscar20xxx~

GayCK 3 years ago

Abby Kitty's Chinese New Year Sissy Training: Cumshots & Edging

Abby Kitty's Chinese New Year Sissy Training: Cumshots & Edging

BallsAndBoobs 2 months ago

Sissy Gimp Maid

Sissy Gimp Maid

XHamster 2 months 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..

PornBox 1 year ago

Slutty gothic taniax plays with dildo and cum in the street PART 2

Slutty gothic taniax plays with dildo and cum in the street PART 2

XHamster 11 months ago

Sissy Hope, great anal gaping compilation

Sissy Hope, great anal gaping compilation

XHamster 2 years ago

The Sissycdmish Situation Is Out of Control!

The Sissycdmish Situation Is Out of Control!

XHamster 1 year ago

Sophia Loreen Private Show

4K 2:00 / 29:39

Sophia Loreen Private Show

Camster 1 week ago

Averyellisxo & MaddietwT take turns getting drilled by a massive dicked femboy in chastity cage

Averyellisxo & MaddietwT take turns getting drilled by a massive dicked femboy in chastity cage

TrannyMovs 10 months ago

Caged shemale gets her booty screwed for 11 minutes str8

Caged shemale gets her booty screwed for 11 minutes str8

SortPorn 2 months ago

Disrobing myself for you with a lil suprise

Disrobing myself for you with a lil suprise

TrannyGem 4 years ago

TS Sub Suspended Hogtied And Fucked

TS Sub Suspended Hogtied And Fucked

BeMyHole 8 months ago

Giovanni Becomes Giovanna Clip 1

Giovanni Becomes Giovanna Clip 1

XHamster 4 months ago

Cute Trans Cutie Drilled Coarse by a Large Thick Shlong

Cute Trans Cutie Drilled Coarse by a Large Thick Shlong

BigTitsLust 2 months ago

BBC fuck a white slut

BBC fuck a white slut

AShemaleTube 1 year ago

Emily austin cuckold creampie eating hottie wife sex puts sissy into chastity

Emily austin cuckold creampie eating hottie wife sex puts sissy into chastity

Tranny.one 4 years ago

outdoor motel risky slutwalk chastity boots

outdoor motel risky slutwalk chastity boots

XHamster 1 month ago

Sissy Showing Chastity Cage and Spanking Herself

Sissy Showing Chastity Cage and Spanking Herself

XHamster 5 months 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 1 year ago

Femboy moans from getting railed by a huge dick in this hot video

Femboy moans from getting railed by a huge dick in this hot video

XXXShemalePorn 1 month ago

blonde sissy fucks herself with a dildo in a chastity belt

blonde sissy fucks herself with a dildo in a chastity belt

XHamster 1 year ago

Super Hot sissy in crimson vinyl pounding a humungous 12 inch black fuck stick

Super Hot sissy in crimson vinyl pounding a humungous 12 inch black fuck stick

TrannyGem 3 years ago

Sissy Teenager In Virginity Ravages Her Caboose And Tongues The Fake Penis

Sissy Teenager In Virginity Ravages Her Caboose And Tongues The Fake Penis

TrannyGem 3 years ago

Pegging My Chastity Sissy Slave In His Tight Ass

Pegging My Chastity Sissy Slave In His Tight Ass

Eporner 8 months ago

Chastity Orgasm - PMV By HoloPMV

Chastity Orgasm - PMV By HoloPMV

AShemaleTube 2 years ago

”Emma Vai's Meat Chastity & Rosebud Experience Is Unforgettable”

”Emma Vai's Meat Chastity & Rosebud Experience Is Unforgettable”

LesbianBliss 4 months ago

24 25 26 27 28

38,720 results found

Related categories

Strap-On Trans Trans Domination Transvestite Sissy Crossdressing Feminization Hermaphrodite Trans Fucks Trans Ladyboy Trans Fucks Girl Trans Solo Trans Chastity Cage Tgirl Trans Fucks Guy Femboy 18+ Futanari Trans Big Cock Self Facial Hands Free

Narrow your search

chastity sissygasm chastity cum sissy chastity chastity fuck chastity bondage chastity compilation chastity cage trans chastity chastity gangbang femboy chastity 18+ bbc chastity chastity bbc fucked in chastity chastity sissy natalie mars chastity chastity anal flat chastity inverted chastity chastity slave chastity bdsm

Categories Pornstars

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.