Chastity Videos - Trans (47,819)

CHASTITY SISSYGASM - Sissy Hands Free Orgasm [Sissification] [HFO] [Sissy Training] Sissy Sluts, ABDL Mind Fuck

CHASTITY SISSYGASM - Sissy Hands Free Orgasm [Sissification] [HFO] [Sissy Training] Sissy Sluts, ABDL Mind Fuck

Clips4sale 1 year ago

dommes in heels punish innocent trans catgirl

HD 0:30 / 13:24

dommes in heels punish innocent trans catgirl

PornBox 3 years ago

Witcher's Delights

HD 0:18 / 21:49

Witcher's Delights

Clips4sale 4 years ago

Mistress starts a new PROSTATE ORGASM training (and seems to work)

58% HD 0:09 / 6:13

Mistress starts a new PROSTATE ORGASM training (and seems to work)

Clips4sale 11 months ago

Nurse DominaFire Sounding Innocence Sissy

Nurse DominaFire Sounding Innocence Sissy

TrannyGem 2 years ago

femboy maidboy and sissy maidgirl breeding (coarse anal chastity bang with cassie coyote!)

femboy maidboy and sissy maidgirl breeding (coarse anal chastity bang with cassie coyote!)

ShemaleSin 6 months ago

Step-MILF Makes You into Her Sissy Bitch

46% 0:10 / 11:28

Step-MILF Makes You into Her Sissy Bitch

Clips4sale 2 years ago

Gorgeous sissy cum in pants

Gorgeous sissy cum in pants

Amateur8 4 months ago

Big Dungeon Party with Slavena Tiger, Adara Jordyn, Mistress Susi PART 1

56% 0:11 / 15:15

Big Dungeon Party with Slavena Tiger, Adara Jordyn, Mistress Susi PART 1

Clips4sale 3 years ago

Sissy Hope Anal Training Pt1

Sissy Hope Anal Training Pt1

XVideos 10 months ago

Mistress Cynthya Joi Cbt Cei (ADVANCED ASS PLAY DILDO FUCK, EDGING, SELF FACIAL CUM EATING, CHASTITY)

Mistress Cynthya Joi Cbt Cei (ADVANCED ASS PLAY DILDO FUCK, EDGING, SELF FACIAL CUM EATING, CHASTITY)

XVideos 3 years ago

I'll Turn You Into My Sissy Slut!

I'll Turn You Into My Sissy Slut!

xHamster 3 months ago

Nickireks smokes and rides her new 8 inch black stud muffin.

Nickireks smokes and rides her new 8 inch black stud muffin.

xHamster 2 years ago

Keisy Royce Private Show

Keisy Royce Private Show

Flirt4Free 1 month ago

Master & Christian Mckenzie & Christian Rey Private Show

61% HD 2:00 / 11:48

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Red Velvet on Bare Skin

Red Velvet on Bare Skin

Flirt4Free 1 month ago

High Heels Love Tongue Worship (720p)

High Heels Love Tongue Worship (720p)

Clips4sale 10 months ago

Yago Tavares1 X Aline Tavares - Cheguei na casa da musa Trans cheio de tes&atilde_o e n&atilde_o resisti a ver o seu rab&atilde_o empinado de 4 , doida para ser fodida com for&ccedil_a at&eacute_ encher seu cu de leite.

Yago Tavares1 X Aline Tavares - Cheguei na casa da musa Trans cheio de tes&atilde_o e n&atilde_o resisti a ver o seu rab&atilde_o empinado de 4 , doida para ser fodida com for&ccedil_a at&eacute_ encher seu cu de leite.

XVideos 11 months ago

Im Going To Fuck You With MY COCK

45% HD 0:25 / 21:50

Im Going To Fuck You With MY COCK

Clips4sale 2 years ago

Chastity guide : A review of all metal chastity cages by sissy joyce

Chastity guide : A review of all metal chastity cages by sissy joyce

RedTube Unknown

Cloe & Charlotte Private Show

HD 2:00 / 13:22

Cloe & Charlotte Private Show

Flirt4Free 3 years ago

Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage!

Trans Sissy Scarlet Sky Sissygasms All Over Herself in Chastity and Bondage!

YouPorn Unknown

Sissy Magic Bomb Chastity Cage Challenge

Sissy Magic Bomb Chastity Cage Challenge

xHamster 2 years ago

Shemale bunny fucked

HD 0:22 / 21:44

Shemale bunny fucked

QueensOfKink 11 months ago

Sissy Oksana shastity riding anal plug

Sissy Oksana shastity riding anal plug

XVideos 7 years ago

Mamou avec Rachelle Karol baise, cravache &eacute_lectrique et &eacute_jaculation buccale ba 4.2

Mamou avec Rachelle Karol baise, cravache &eacute_lectrique et &eacute_jaculation buccale ba 4.2

XVideos 5 months ago

LET'S PLAY A GAME

LET'S PLAY A GAME

Clips4sale 3 years ago

Big Tits Brittany Andrews Breaks In Her Slutty Slavebot TS Slayer

Big Tits Brittany Andrews Breaks In Her Slutty Slavebot TS Slayer

Clips4sale 7 months ago

Cloe & Charlotte Private Show

Cloe & Charlotte Private Show

Flirt4Free 3 years ago

Caged Trans Girl Anal Training With Huge Tentacle and Plugs

HD 0:15 / 10:56

Caged Trans Girl Anal Training With Huge Tentacle and Plugs

Clips4sale 8 months ago

exposed cocklocked tranny sissy drew shows daily ass workout

exposed cocklocked tranny sissy drew shows daily ass workout

XVideos 2 years ago

Shemale Hentai stepsister cumming on her stepbro in chastity cg shemale hentai x hunk

Shemale Hentai stepsister cumming on her stepbro in chastity cg shemale hentai x hunk

ShemaleSin 3 years ago

TS Mistress Jessy Dubai

59% 0:11 / 36:34

TS Mistress Jessy Dubai

C4S 2 years ago

Hands Free Trans Cumshots Compilation 1

Hands Free Trans Cumshots Compilation 1

XVideos 1 year ago

We Like You Better as a Girl

44% HD 0:26 / 10:54

We Like You Better as a Girl

Clips4sale 1 year ago

Breakfast slave for cute tranny girl! He gets spit on and fucked in his ass!

65% HD 0:25 / 7:55

Breakfast slave for cute tranny girl! He gets spit on and fucked in his ass!

Clips4sale 1 year ago

&Eacute_ LEITE QUE VOC&Ecirc_S GOSTAM ?? Fiquem com as melhores gozadas do m&ecirc_s de julho

&Eacute_ LEITE QUE VOC&Ecirc_S GOSTAM ?? Fiquem com as melhores gozadas do m&ecirc_s de julho

XVideos 8 months ago

Fucked in Suspension by Goddess Adara and Mistress Susi FullHD

HD 0:34 / 10:11

Fucked in Suspension by Goddess Adara and Mistress Susi FullHD

Clips4sale 3 years ago

Sophia Loreen Party on Jan 31, 2026 - Part 2

4K 2:00 / 31:36

Sophia Loreen Party on Jan 31, 2026 - Part 2

Flirt4Free 1 month ago

Innocence Cell Challange - Day 1/ten

Innocence Cell Challange - Day 1/ten

Gayhub 7 months ago

Selfbondage2, My second attempt at crossdressed selfbondage, this time using remote contol vibrating eggs

Selfbondage2, My second attempt at crossdressed selfbondage, this time using remote contol vibrating eggs

XVideos 7 years ago

This Pathetic Slut Loves Can NOT Stop Cumming & Eating It After!

This Pathetic Slut Loves Can NOT Stop Cumming & Eating It After!

xHamster 1 year ago

Raver Sissy femboy in chastity fucks BBC 4 Femdom Goddess while she eats dinner, rough anal slut 4/5

Raver Sissy femboy in chastity fucks BBC 4 Femdom Goddess while she eats dinner, rough anal slut 4/5

RedTube Unknown

I will put you in virtual chastity Trans JOI

I will put you in virtual chastity Trans JOI

YouPorn Unknown

Female DOMINATION in DIAPERS and CHASTITY with a big ANAL plug and PISS

Female DOMINATION in DIAPERS and CHASTITY with a big ANAL plug and PISS

YouPorn Unknown

SPORTS TRYOUTS! OTS842

Premium HD 27:43

SPORTS TRYOUTS! OTS842

Sheer 5 years ago

Mamou avec Rachelle Karol je prends une jolie soumise en levrette ba 3.2

Mamou avec Rachelle Karol je prends une jolie soumise en levrette ba 3.2

XVideos 5 months ago

Huge Facial After Rough Throat Fuck

Huge Facial After Rough Throat Fuck

XVideos 2 years ago

Yourprettykate's Chastity Belt Fetish: Masturbating with Dildo and High Socks for Daddy's Satisfaction

Yourprettykate's Chastity Belt Fetish: Masturbating with Dildo and High Socks for Daddy's Satisfaction

TrannyMovs 6 months ago

Kandys Sissy Bitch Jizelle Gets A Caged Prostate Milking

HD 0:22 / 12:08

Kandys Sissy Bitch Jizelle Gets A Caged Prostate Milking

Clips4sale 1 month ago

Be Our Girlfriend: Miss S and I transform you into the perfect girlfriend by caging your tiny cock, dressing you in lingerie, and applying pretty makeup

Be Our Girlfriend: Miss S and I transform you into the perfect girlfriend by caging your tiny cock, dressing you in lingerie, and applying pretty makeup

Clips4sale 6 months ago

Top 10 Sissy Ideas 2024

HD 0:54 / 10:14

Top 10 Sissy Ideas 2024

Clips4sale 9 months ago

Strap on & chastity punishment for stealing Mistress' clothes 🔐 @Saskia_and_Sasha

Strap on & chastity punishment for stealing Mistress' clothes 🔐 @Saskia_and_Sasha

RedTube Unknown

My Sissy slave tore up his stockings_The Dragonlady_Femdom_Sissytraining_Feminization_Whipping (SD) (WMV)

My Sissy slave tore up his stockings_The Dragonlady_Femdom_Sissytraining_Feminization_Whipping (SD) (WMV)

Clips4sale 3 years ago

Red Devil Part 1

Red Devil Part 1

Clips4sale 2 years ago

Sissies Belong In Chastity (SD MP4)

60% 4K 0:30 / 15:17

Sissies Belong In Chastity (SD MP4)

Clips4sale 2 years ago

Sexy Blonde TS Bailey Wilde Fucked in Chastity

Sexy Blonde TS Bailey Wilde Fucked in Chastity

XVideos 1 month ago

Multiple Anal Sissy Orgasms in Chastity Cage & Then Unlocked Massive Cumshot Jessica Bloom

Multiple Anal Sissy Orgasms in Chastity Cage & Then Unlocked Massive Cumshot Jessica Bloom

YouPorn Unknown

Jessica Bloom Cumshot Compilation 2024

Jessica Bloom Cumshot Compilation 2024

XVideos 1 year ago

Sissy Shopping Rules for Good Girls – Feminization Training by Goddess Nikki Kit

63% HD 0:20 / 5:04

Sissy Shopping Rules for Good Girls – Feminization Training by Goddess Nikki Kit

Clips4sale 1 year ago

Sissy Training task - Ass Fucked in chastity

Sissy Training task - Ass Fucked in chastity

Clips4sale 1 year ago

Chastity T-Girl, Claire Tenebrarum, 5on1, Anal Fisting, DAP, Gapes, Swallow BTG063

Chastity T-Girl, Claire Tenebrarum, 5on1, Anal Fisting, DAP, Gapes, Swallow BTG063

XVideos 4 years ago

Fuzzy Sock Gag and Chastity Pegging Humiliation for Sissy with Anal Sock Stuffing by Mistress Mercer

Fuzzy Sock Gag and Chastity Pegging Humiliation for Sissy with Anal Sock Stuffing by Mistress Mercer

RedTube Unknown

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

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

XVideos 1 month ago

Sissy BNWO while get fucked by sex maschine

Sissy BNWO while get fucked by sex maschine

XVideos 7 months ago

Lady Alice compilation 05 Queen of Hell (mesmerize version) View originals by subscription 4K HIGH FR60 FPS60

Lady Alice compilation 05 Queen of Hell (mesmerize version) View originals by subscription 4K HIGH FR60 FPS60

XVideos 2 years ago

ladyboy fucks herself with huge deep plug

ladyboy fucks herself with huge deep plug

XVideos 8 months ago

FemBoy caught on cam playing with Fucking machine

FemBoy caught on cam playing with Fucking machine

xHamster 11 months ago

Trans Teen Chastity Anal Threesome

Trans Teen Chastity Anal Threesome

RedTube Unknown

Me folla a pelo el maestro de la escuela mientras su novia no est&aacute_

Me folla a pelo el maestro de la escuela mientras su novia no est&aacute_

XVideos 4 months ago

White Sissy slave in steel chastity deepthroats and tongues &#039_s ass.Sissyann

White Sissy slave in steel chastity deepthroats and tongues &#039_s ass.Sissyann

XVideos 8 years ago

Sloppy Upside Down Sissy Throat Fucking Training

Sloppy Upside Down Sissy Throat Fucking Training

XVideos 3 years ago

[FayGrey] [Femdom Futanari Harem Double Penetration sissy] (femdom assplay PetPlay and sissification)

[FayGrey] [Femdom Futanari Harem Double Penetration sissy] (femdom assplay PetPlay and sissification)

XVideos 4 years ago

Sissy School Vlog Kitten is Locked Up

61% HD 0:26 / 11:17

Sissy School Vlog Kitten is Locked Up

Clips4sale 2 years ago

[EmilyVu] Oriental Femboy masturbates with sex-toy and orgasms in chastity cage.

[EmilyVu] Oriental Femboy masturbates with sex-toy and orgasms in chastity cage.

ShemaleSin 7 months ago

Sissy Magic Bomb Chastity Cage Defiance

Sissy Magic Bomb Chastity Cage Defiance

ShemaleSin 2 years 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!

Clips4sale 1 year ago

Futa Mommydom Mesmerises You At The Movies [Femdress, Chastity, Oral, Vibrator JOI]

Futa Mommydom Mesmerises You At The Movies [Femdress, Chastity, Oral, Vibrator JOI]

YouPorn Unknown

Yourprettykate's chastity belt is a hot cum-lubricating tool for her dildo-fucking self

Yourprettykate's chastity belt is a hot cum-lubricating tool for her dildo-fucking self

TrannyMovs 6 months ago

MILF1867 - Pegging the Bully: Rachel Steele & London River’s Femdom Justice

HD 0:30 / 34:59

MILF1867 - Pegging the Bully: Rachel Steele & London River’s Femdom Justice

Clips4sale 1 year ago

Desire Sweet Private Show

HD 2:00 / 18:27

Desire Sweet Private Show

Flirt4Free 1 month ago

NOVINHA TRANS COSPLAYER DANDO O CUZINHO PARA DOIS NOVINHOS DOTADOS - COMPLETO NO RED - ALICE HAEL

NOVINHA TRANS COSPLAYER DANDO O CUZINHO PARA DOIS NOVINHOS DOTADOS - COMPLETO NO RED - ALICE HAEL

XVideos 1 month ago

Sablique - Funsize Frank Dress Up Curtsy Training

59% 0:50 / 7:15

Sablique - Funsize Frank Dress Up Curtsy Training

Clips4sale 2 years ago

女装アナニー総集編！連続メスイキで大量潮吹き/// #2（貞操帯ピストンマシーン）

女装アナニー総集編！連続メスイキで大量潮吹き/// #2（貞操帯ピストンマシーン）

TrannyGem 1 year ago

Natalie Mars Passionate Sex Scene with Owen Gray DeepLush

Natalie Mars Passionate Sex Scene with Owen Gray DeepLush

SpankBang 3 years ago

TGirl Lucy in Chastity - toying her sissy ass with big dildos

TGirl Lucy in Chastity - toying her sissy ass with big dildos

YouPorn Unknown

Chastity Tease

Clips4sale 8 months ago

Trans Venus Lux plows Reed Jameson till he is covered with her cum

Trans Venus Lux plows Reed Jameson till he is covered with her cum

UrGayPorn 5 months ago

Mistress Mercer Cumming on FuckMachine Latex Sissy Chastity Release

Mistress Mercer Cumming on FuckMachine Latex Sissy Chastity Release

YouPorn Unknown

Sissy Bimbo Brandynette First Time Caged plugged with lovense hush 45mm

Sissy Bimbo Brandynette First Time Caged plugged with lovense hush 45mm

XVideos 6 years ago

Miss Hannah Blake & Rubber Rose - Big ass MILF pegging hot TS (HD1080p)

HD 0:21 / 12:03

Miss Hannah Blake & Rubber Rose - Big ass MILF pegging hot TS (HD1080p)

Clips4sale 1 month ago

Sub Torment 8 mp4

Sub Torment 8 mp4

Clips4sale 2 years ago

Trans Chastity Beauties Tease With Toys

Trans Chastity Beauties Tease With Toys

SpankBang 7 months ago

Extreme Bondage Male: Crossdresser stepson is found by Step Mom Charlie Monaco!

56% 0:13 / 9:40

Extreme Bondage Male: Crossdresser stepson is found by Step Mom Charlie Monaco!

Clips4sale 1 year ago

Mistress Baton Does The Thousand Fist Challenge HD for QT

Premium 4K 37:46

Mistress Baton Does The Thousand Fist Challenge HD for QT

Clips4sale 1 year ago

Sissification Transformation by Roommate

Sissification Transformation by Roommate

XVideos 4 months ago

Niqab shemail locked in chastity and fucking dildo

Niqab shemail locked in chastity and fucking dildo

BallsAndBoobs 3 months ago

Hot Trans Bailey Wilde Fucked Missionary

Hot Trans Bailey Wilde Fucked Missionary

XVideos 2 weeks ago

Sissy bitch i chastity anal play

Sissy bitch i chastity anal play

XVideos 8 months ago

Locked Up and Dressed Up for Worship

Locked Up and Dressed Up for Worship

Clips4sale 5 months ago

HOTTEST Crossdresser Bailey Wilde in Pink Chastity Fucked Missionary

HOTTEST Crossdresser Bailey Wilde in Pink Chastity Fucked Missionary

XVideos 7 months ago

Sissy cuckold in chastity cage watching her girlfriend getting fucked by her lover

Sissy cuckold in chastity cage watching her girlfriend getting fucked by her lover

XVideos 1 year ago

TRAVESTI RABUDA SENTANDO FIRME NA PIROCA - COMPLETO NO RED - LUANA PRADO

TRAVESTI RABUDA SENTANDO FIRME NA PIROCA - COMPLETO NO RED - LUANA PRADO

XVideos 6 months ago

Rebecca Vanguard Turns Into A Human Skewer In A TS 3some!

Rebecca Vanguard Turns Into A Human Skewer In A TS 3some!

XVideos 1 year ago

sissy girl locked and desperate in her chastity cage while getting destroyed by big bbc toy

sissy girl locked and desperate in her chastity cage while getting destroyed by big bbc toy

RedTube Unknown

futa nurse pegging part 3: latex catsuit, sissy chastity, fisting - full video on Veggiebabyy Manyvids

futa nurse pegging part 3: latex catsuit, sissy chastity, fisting - full video on Veggiebabyy Manyvids

XVideos 1 year ago

Mamou avec Rachelle Karol je domine une jolie soumise avant de la prendre en levrette ba2.3

Mamou avec Rachelle Karol je domine une jolie soumise avant de la prendre en levrette ba2.3

XVideos 5 months ago

French bitch gets punished - Episode 1 mp4

HD 1:00 / 30:22

French bitch gets punished - Episode 1 mp4

Clips4sale 1 year ago

Your Step by Step Sissification Training

HD 0:29 / 17:19

Your Step by Step Sissification Training

Clips4sale 2 years ago

Vibrate your Clitty - Sissy Gooning JOI by Goddess Nikki Kit

Vibrate your Clitty - Sissy Gooning JOI by Goddess Nikki Kit

Clips4sale 1 year ago

Nun Dildo Dommed & Spanked By Priest

Premium HD 12:34

Nun Dildo Dommed & Spanked By Priest

Sheer 2 years ago

Triple trouble! Bleach girls break your mind /Futa/Cuck JOI

Triple trouble! Bleach girls break your mind /Futa/Cuck JOI

XVideos 11 months ago

Inverted Chastity &amp_ Candle Wax Go Together Like PB &amp_ J, Yay!

Inverted Chastity &amp_ Candle Wax Go Together Like PB &amp_ J, Yay!

XVideos 2 years ago

bubble butt slut

bubble butt slut

Clips4sale 1 year ago

TE GUSTAR&Iacute_A ESTO MIRA TODO LO QUE EST&Aacute_ EN RED

TE GUSTAR&Iacute_A ESTO MIRA TODO LO QUE EST&Aacute_ EN RED

XVideos 2 years ago

BOBSTGIRLS: A Wet Peachie

BOBSTGIRLS: A Wet Peachie

ShemaleSin 2 years ago

amazing big but tranny milf traning her ass with a fuck machine and huge dildos

amazing big but tranny milf traning her ass with a fuck machine and huge dildos

XVideos 2 years ago

Submissive Girl In Chastity Cums So Hard And Fast

Submissive Girl In Chastity Cums So Hard And Fast

XVideos 1 year ago

Meu Namorado Yago Tavares me colocou de quatro no sof&aacute_, fodeu meu cu sem d&oacute_ e ainda me deu um banho de leite

Meu Namorado Yago Tavares me colocou de quatro no sof&aacute_, fodeu meu cu sem d&oacute_ e ainda me deu um banho de leite

XVideos 8 months ago

Sissy locked in a dress and Chastity device

Sissy locked in a dress and Chastity device

XVideos 7 years ago

75 76 77 78 79

47,819 results found

Related categories

Strap-On Trans Trans Domination Transvestite Crossdressing Trans Fucks Trans Sissy Hermaphrodite Trans Fucks Girl Feminization Trans Solo Self Facial Trans Fucks Guy Self Suck Ladyboy Trans Big Cock Tgirl Chastity Cage Trans Compilation Hands Free Trans Post-Op

Narrow your search

chastity cum chastity cage chastity orgasm chastity gangbang chastity bbc trans chastity natalie mars chastity chastity dildo chastity anal bbc chastity permanent chastity chastity compilation chastity sissy asian chastity sissy chastity chastity pegging chastity bondage fucked in chastity flat chastity femboy chastity 18+

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.