Jail Videos - Trans (550)

johannesgaming - update #119 - futa dating simulator 11 ava is a prison bitch will she fuck you or will you fuck her - jun 27, 2024

johannesgaming - update #119 - futa dating simulator 11 ava is a prison bitch will she fuck you or will you fuck her - jun 27, 2024

PornBox 1 year ago

Nara offer her slave as a fuck toy for TS Alexia Duucan (720 EN-sub)

66% HD 0:30 / 20:36

Nara offer her slave as a fuck toy for TS Alexia Duucan (720 EN-sub)

Clips4sale 8 months ago

(slow Motion) - Showing My Tinder Date My Thick Flaccid Cock Before Our Date.

(slow Motion) - Showing My Tinder Date My Thick Flaccid Cock Before Our Date.

FapHouse 5 months ago

Milk Cock

FapHouse 4 months ago

Desi Hard Work Muth Mastrubation Sex Video

HD 0:39 / 10:17

Desi Hard Work Muth Mastrubation Sex Video

FapHouse 4 months ago

HONOR AMONG QUEENS

66% HD 0:10 / 24:59

HONOR AMONG QUEENS

LoyalFans 4 months ago

Young Creamy Fuck Inexperienced Femboy in Fuck. Cum in Tiny Ass BDSM

Young Creamy Fuck Inexperienced Femboy in Fuck. Cum in Tiny Ass BDSM

FapHouse 4 months ago

Man Catcher Part 6

4K 0:40 / 11:04

Man Catcher Part 6

Clips4sale 1 year ago

ts outlaw thayla santos flipflops her way out of prison dt387

HD 1:02 / 29:47

ts outlaw thayla santos flipflops her way out of prison dt387

PornBox 3 years ago

blonde transsexual prison inmate jamaima carvallo masturbates in her cel

HD 0:30 / 15:17

blonde transsexual prison inmate jamaima carvallo masturbates in her cel

PornBox 6 days ago

D Vikky Strapon and Anal Play Part 1

66% 0:15 / 6:46

D Vikky Strapon and Anal Play Part 1

Clips4sale 5 months ago

Milky Femboy Sissy with a Big Dick Fucked in a Beautiful Ass.

HD 0:39 / 10:28

Milky Femboy Sissy with a Big Dick Fucked in a Beautiful Ass.

FapHouse 7 months ago

Bigg Hunk Bwlojob

Bigg Hunk Bwlojob

FapHouse 7 months ago

he fucks sissy after he got out of jail

Premium HD 5:00

he fucks sissy after he got out of jail

XVideosRed 2 months ago

I Fuck You Like A Whore

I Fuck You Like A Whore

Clips4sale 3 years ago

WRONG HOUSE *HD 720*

HD 0:33 / 14:14

WRONG HOUSE *HD 720*

Clips4sale 2 years ago

Comendo a carcereira cheia de tes&atilde_o

Premium HD 26:26

Comendo a carcereira cheia de tes&atilde_o

xnxxGold 6 years ago

A super hot dickgirl plays with a sexy young brunette in the medieval castle

Premium HD 10:40

A super hot dickgirl plays with a sexy young brunette in the medieval castle

xnxxGold 2 years ago

Giada Da Vinci pushes the cum out of the cock with a big dildo in the ass with big toys, strap-on, crossdresser

Giada Da Vinci pushes the cum out of the cock with a big dildo in the ass with big toys, strap-on, crossdresser

Clips4sale 2 years ago

Hot Prisoner Shemale ladyboy Cute BBW Blonde Booty Crossdresser Femboy

Premium HD 16:55

Hot Prisoner Shemale ladyboy Cute BBW Blonde Booty Crossdresser Femboy

xnxxGold 2 years ago

Shemale prison fantasy

HD 0:40 / 28:25

Shemale prison fantasy

FapHouse 6 years ago

Shemale Lockdown

HD 0:30 / 1:21:00

Shemale Lockdown

AEBN 21 years ago

Hot Prisoner Shemale ladyboy Cute BBW Blonde Booty Crossdresser Femboy

Premium HD 16:55

Hot Prisoner Shemale ladyboy Cute BBW Blonde Booty Crossdresser Femboy

XVideosRed 2 years ago

Red Hot Riding PT. 1- Futa Fucking Police Station

Premium HD 7:57

Red Hot Riding PT. 1- Futa Fucking Police Station

xnxxGold 3 years ago

Princess Donna's Snatched & Kept New Sextoy Stefani Special

Premium 1:03:15

Princess Donna's Snatched & Kept New Sextoy Stefani Special

Fucked the Young Worker That Made Him Want to Eat My Cum

68% HD 0:39 / 16:55

Fucked the Young Worker That Made Him Want to Eat My Cum

FapHouse 7 months ago

He Had Me Cumming

Premium HD 24:17

He Had Me Cumming

TransAngels 1 year ago

TS-Giantess escapes prison and grows and takes over the world!!!

48% 0:30 / 5:35

TS-Giantess escapes prison and grows and takes over the world!!!

Clips4sale 5 months ago

Police with Strapon

Police with Strapon

Flirt4Free 1 year ago

Looking My Pennies

Looking My Pennies

FapHouse 10 months ago

Jasmine Dlight Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out

HD 0:39 / 11:29

Jasmine Dlight Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out

FapHouse 1 year ago

Sissy Ladyboy Sucks Dick in Prison

63% HD 0:39 / 15:13

Sissy Ladyboy Sucks Dick in Prison

FapHouse 11 months ago

Shemale Fucks Girl Standing in Bondage Prison Sex

Shemale Fucks Girl Standing in Bondage Prison Sex

FapHouse 11 months ago

Dickgirl Ladyboy Is Fucking Girl Standing In Her Prison Cell

Premium HD 17:47

Dickgirl Ladyboy Is Fucking Girl Standing In Her Prison Cell

xnxxGold 10 months ago

Big Ass

FapHouse 10 months ago

Indian Bisexual Tina Hot Scenes

Indian Bisexual Tina Hot Scenes

FapHouse 1 year ago

You're going to futa jail WMV

HD 0:26 / 11:00

You're going to futa jail WMV

Clips4sale 11 months ago

Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell

66% HD 0:07 / 0:39

Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell

FapHouse 10 months ago

Prison Thug Jacks off Huge Big Black Cock

Prison Thug Jacks off Huge Big Black Cock

FapHouse 10 months ago

shemale fucks girl standing in bondage prison sex

HD 0:30 / 15:53

shemale fucks girl standing in bondage prison sex

PornBox 10 months ago

Unique ingredient

Unique ingredient

Clips4sale 4 years ago

Blonde transsexual prison inmate Jamaima Carvallo masturbates in her cel

Blonde transsexual prison inmate Jamaima Carvallo masturbates in her cel

FapHouse 7 years ago

johannesgaming - update #121 - futa dating simulator 11 ava is a prison bitch will she fuck you or will you fuck her - jul 02, 2024

johannesgaming - update #121 - futa dating simulator 11 ava is a prison bitch will she fuck you or will you fuck her - jul 02, 2024

PornBox 1 year ago

I Have a Date with a Girl and I Want to Gain 4 Centimeters, Better Penis Pump Technique

57% HD 0:39 / 1:08

I Have a Date with a Girl and I Want to Gain 4 Centimeters, Better Penis Pump Technique

FapHouse 1 year ago

Nara offer her slave as a fuck toy for TS Alexia Duucan (720 EN-sub)

HD 0:30 / 20:36

Nara offer her slave as a fuck toy for TS Alexia Duucan (720 EN-sub)

Clips4sale 8 months ago

My Hunk Bwlojob

My Hunk Bwlojob

FapHouse 6 months ago

Prison of Sissy - Crime Is Not the Way to Go.

61% 0:39 / 31:05

Prison of Sissy - Crime Is Not the Way to Go.

FapHouse 6 months ago

Prison of Sissy - Crime Is Not the Way to Go.

Prison of Sissy - Crime Is Not the Way to Go.

FapHouse 6 months ago

My Anal Orgasm

FapHouse 5 months ago

Sissy Rozebell - Tranny Love Black Dick Part3

Sissy Rozebell - Tranny Love Black Dick Part3

FapHouse 5 months ago

Shemale Standing Fuck Ladyboy Prison Sex

Premium HD 14:13

Shemale Standing Fuck Ladyboy Prison Sex

XVideosRed 11 months ago

Blonde transsexual prison inmate Jamaima Carvallo masturbates in her cel

Blonde transsexual prison inmate Jamaima Carvallo masturbates in her cel

xnxxGold 1 week ago

Hunk Bwlojob

FapHouse 1 month ago

Blonde Big Tit Shemale Gets Anal Fucked by a Prison Guard

Blonde Big Tit Shemale Gets Anal Fucked by a Prison Guard

FapHouse 1 month ago

He just got out of prison and wanted some ass

Premium HD 10:09

He just got out of prison and wanted some ass

XVideosRed 3 months ago

You are my cum dump

HD 0:10 / 15:06

You are my cum dump

LoyalFans 2 months ago

Curvy TS prison guard Drika Lima rides inmates cock

HD 0:39 / 36:01

Curvy TS prison guard Drika Lima rides inmates cock

FapHouse 2 years ago

THE POLICE PIETRA FARTING IN THE CRIMINAL - BY PIETRA HUNTER - FULL VERSION IN FULL HD

HD 0:59 / 22:37

THE POLICE PIETRA FARTING IN THE CRIMINAL - BY PIETRA HUNTER - FULL VERSION IN FULL HD

Clips4sale 2 years ago

BLACK MEGA GIANTESS Growth - GIANT Babe + Couple - Point of view VR - 3D Hentai - Full HD MP4 1080p

BLACK MEGA GIANTESS Growth - GIANT Babe + Couple - Point of view VR - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

NO SIN GOES UNPUNISHED *HD 720*

HD 0:36 / 17:31

NO SIN GOES UNPUNISHED *HD 720*

Clips4sale 4 years ago

perverted futanari cop arranged hard anal sex and facefuck for a sexy prisoner (sims + anime hentai + sfm)

HD 5:00 / 22:01

perverted futanari cop arranged hard anal sex and facefuck for a sexy prisoner (sims + anime hentai + sfm)

PornBox 1 year ago

Femboy Zelda Captured by Ganondorf

Femboy Zelda Captured by Ganondorf

FapHouse 1 year ago

Johannesgaming - update #121 - Futa Dating Simulator 11 Ava is a prison bitch will she fuck you or will you fuck her - Jul 02, 2024

Johannesgaming - update #121 - Futa Dating Simulator 11 Ava is a prison bitch will she fuck you or will you fuck her - Jul 02, 2024

xnxxGold 1 year ago

Cyber angel dickgirl plays with a sexy young ebony in the sci-fi lab

Premium HD 11:41

Cyber angel dickgirl plays with a sexy young ebony in the sci-fi lab

xnxxGold 2 years ago

grief counseling: rip to your vanilla life

62% HD 0:10 / 8:39

grief counseling: rip to your vanilla life

LoyalFans 1 year ago

Chatlie Monaco has you Bound Gagged and Made to watch!

Chatlie Monaco has you Bound Gagged and Made to watch!

Clips4sale 1 year ago

Hairy Armpits worship (wmv)

Hairy Armpits worship (wmv)

Clips4sale 3 years ago

Bang My Tranny Ass 3

HD 0:30 / 2:07:00

Bang My Tranny Ass 3

AEBN 16 years ago

Bang My Tranny Ass 4

55% HD 0:30 / 1:44:00

Bang My Tranny Ass 4

AEBN 16 years ago

Hot active shemale fucks hard a sexy cuffed young blonde in the basement

HD 0:39 / 20:56

Hot active shemale fucks hard a sexy cuffed young blonde in the basement

FapHouse 4 years ago

Two mesmerizing TS goddesses making passionate love

HD 0:39 / 32:41

Two mesmerizing TS goddesses making passionate love

FapHouse 6 years ago

Dylan transvestites himself to satisfy transgressive sex

HD 0:39 / 21:02

Dylan transvestites himself to satisfy transgressive sex

FapHouse 4 years ago

Her Prisoner Part 20 - Sissy Training Part III **MOV**

4K 0:48 / 10:10

Her Prisoner Part 20 - Sissy Training Part III **MOV**

Clips4sale 2 years ago

GIANTESS VORE Blowjob - GIANT FEMDOM - Hot Blonde Babe Sucking a Guys Dick - 3D Hentai - Full HD MP4 1080p

GIANTESS VORE Blowjob - GIANT FEMDOM - Hot Blonde Babe Sucking a Guys Dick - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

Cyber angel dickgirl plays with a sexy young ebony in the sci-fi lab

Premium HD 11:41

Cyber angel dickgirl plays with a sexy young ebony in the sci-fi lab

XVideosRed 2 years ago

Sissy Ladyboy Standing Anal in Prison

Premium HD 14:24

Sissy Ladyboy Standing Anal in Prison

XVideosRed 11 months ago

Dickgirl Ladyboy Is Fucking Girl Standing In Her Prison Cell

Premium HD 17:47

Dickgirl Ladyboy Is Fucking Girl Standing In Her Prison Cell

XVideosRed 10 months ago

Satyam XXX Sexy Video Indian and India

Satyam XXX Sexy Video Indian and India

FapHouse 10 months ago

Anal Sex

FapHouse 10 months ago

Humiliation for Crossdresser stepson is found by Step Mom Charlie Monaco!

65% 0:13 / 9:40

Humiliation for Crossdresser stepson is found by Step Mom Charlie Monaco!

Clips4sale 11 months ago

Little Penis in Slow Motion

Little Penis in Slow Motion

FapHouse 10 months ago

Big Hunk

FapHouse 9 months ago

Chelsea Marie Pounds Strong-Willed Arielle Aquinas Into Submission

Premium HD 44:41

Chelsea Marie Pounds Strong-Willed Arielle Aquinas Into Submission

KinkTrans 7 years ago

BLUE MONDAY

Clips4sale 1 year ago

THE LAST WISH

Clips4sale 1 year ago

shemale prison

Premium HD 28:25

xnxxGold 6 years ago

Super hot gamer girl gets hard anal fuck with a sexy futanari in the sci-fi prison

HD 0:39 / 16:33

Super hot gamer girl gets hard anal fuck with a sexy futanari in the sci-fi prison

FapHouse 2 years ago

Super Sexy Trans Girl in Cuffs Gets Fucked Hard by BBC in the Prison

HD 0:39 / 10:22

Super Sexy Trans Girl in Cuffs Gets Fucked Hard by BBC in the Prison

FapHouse 2 years ago

Amazing bubble butt latina transsexual Andressa Buen strokes her cock in her jail cell

Premium HD 20:12

Amazing bubble butt latina transsexual Andressa Buen strokes her cock in her jail cell

xnxxGold 3 years ago

Facesitting for prisoner (wmv)

Facesitting for prisoner (wmv)

Clips4sale 3 years ago

Johannesgaming - update #121 - Futa Dating Simulator 11 Ava is a prison bitch will she fuck you or will you fuck her - Jul 02, 2024

Premium HD 32:02

Johannesgaming - update #121 - Futa Dating Simulator 11 Ava is a prison bitch will she fuck you or will you fuck her - Jul 02, 2024

Sheer 1 year ago

Prison of Sissy 3 the Pr Manager Fucked

55% 0:39 / 11:09

Prison of Sissy 3 the Pr Manager Fucked

FapHouse 6 months ago

Mitch West and Mia Isabella

Premium HD 42:03

Mitch West and Mia Isabella

KinkTrans 18 years ago

Prisoner Put His Dick in the Transvestite Police Officer

Prisoner Put His Dick in the Transvestite Police Officer

FapHouse 1 year ago

Kinky drill instructor insults Asian girl in prison

HD 0:39 / 23:10

Kinky drill instructor insults Asian girl in prison

FapHouse 3 years ago

Smooth Skin, Dirty Thoughts

Smooth Skin, Dirty Thoughts

FapHouse 3 months ago

Johannesgaming - update #375 - Prison of Sissy - crime is not the way to go - May 26, 2025

Premium HD 30:52

Johannesgaming - update #375 - Prison of Sissy - crime is not the way to go - May 26, 2025

Sheer 6 months ago

Prison of Sissy 3 the Pr Manager Fucked

Prison of Sissy 3 the Pr Manager Fucked

FapHouse 6 months ago

My Amateur Twink Roommate Thanks Me with Blowjob

My Amateur Twink Roommate Thanks Me with Blowjob

FapHouse 3 months ago

Johannesgaming - update #375 - Prison of Sissy - crime is not the way to go - May 26, 2025

Johannesgaming - update #375 - Prison of Sissy - crime is not the way to go - May 26, 2025

xnxxGold 6 months ago

I Enjoyed the Bathtub Naked the Other Day at the Gay Party at the Motel

HD 0:39 / 11:11

I Enjoyed the Bathtub Naked the Other Day at the Gay Party at the Motel

FapHouse 11 months ago

Big Cock Hunk Belwojob

Big Cock Hunk Belwojob

FapHouse 9 months ago

You Are a Prisoner to Your Sissy Porn

HD 0:39 / 11:48

You Are a Prisoner to Your Sissy Porn

FapHouse 5 months ago

How to Dress Your Sissy with Gwen Gordon

How to Dress Your Sissy with Gwen Gordon

C4S 4 months ago

Bnwo Sissy Breeding Stables

HD 0:39 / 10:46

Bnwo Sissy Breeding Stables

FapHouse 2 months ago

JUST OUT OF JAIL AND HE NEEDED SOME ASS

Premium HD 3:00

JUST OUT OF JAIL AND HE NEEDED SOME ASS

xnxxGold 3 months ago

Girl Sucks Sissy Ladyboy Dick in Prison

65% HD 0:39 / 14:12

Girl Sucks Sissy Ladyboy Dick in Prison

FapHouse 10 months ago

Prison of Sissy 2 Adam Used the Glory Hole Not to Get a BJ but to Give

Prison of Sissy 2 Adam Used the Glory Hole Not to Get a BJ but to Give

FapHouse 6 months ago

Secrets of Area 51. Sci-fi female android fucks a young woman strapon

Premium HD 20:03

Secrets of Area 51. Sci-fi female android fucks a young woman strapon

XVideosRed 5 years ago

Secrets of Area 51. Sci-fi female android fucks a young woman strapon

Premium HD 20:03

Secrets of Area 51. Sci-fi female android fucks a young woman strapon

xnxxGold 5 years ago

Latina shemale prison guard fucks her inmate

HD 0:39 / 34:08

Latina shemale prison guard fucks her inmate

FapHouse 6 years ago

Policewoman with a huge cock turns her prisoner into a dick slut

Premium HD 27:03

Policewoman with a huge cock turns her prisoner into a dick slut

XVideosRed 3 years ago

Cock Belwojob

HD 0:39 / 10:31

FapHouse 10 months ago

sissy ladyboy standing anal in prison

HD 0:30 / 14:23

sissy ladyboy standing anal in prison

PornBox 11 months ago

Her Prisoner Part 22 - Sissy Training V **wmv**

4K 0:26 / 10:09

Her Prisoner Part 22 - Sissy Training V **wmv**

Clips4sale 11 months ago

Nyobi Khan and Rico

Premium HD 59:46

Nyobi Khan and Rico

KinkTrans 17 years ago

Hunted & Caged Part 6

4K 0:23 / 13:19

Hunted & Caged Part 6

Clips4sale 2 years ago

Trans Teen Grazyeli Silva Toys Ass And Cums In prison

Trans Teen Grazyeli Silva Toys Ass And Cums In prison

FapHouse 2 years ago

Young Brazilian Soldier Fucks Two Beautiful Prisoner Outside The Camp

Young Brazilian Soldier Fucks Two Beautiful Prisoner Outside The Camp

xnxxGold 3 years ago

FUTA GIANTESS uses girl as Sex Toy - GIANT FUTANARI DOMINATION - Hot Babe Jerking off a Huge Dick - 3D Hentai - Full HD MP4 1080p

HD 0:10 / 15:18

FUTA GIANTESS uses girl as Sex Toy - GIANT FUTANARI DOMINATION - Hot Babe Jerking off a Huge Dick - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

1 2 3 4 5

550 results found

Related categories

Prison Dungeon Basement Bound Spanked Maledom Tied Up Cage Suspension Slave Mud Leashed Hazing Bondage Tied Up & Fucked WTF Training Bondage Orgasm Librarian Handcuffed

Narrow your search

gay jail jail sex black jail lesbian jail jail gangbang lisa ann jail jail lesbian daisy marie jail lexi belle jail madison parker jail japanese jail audrey bitoni jail anna claire clouds jail aletta ocean jail krissy lynn jail shyla stylez jail jail femdom phoenix marie jail alexis texas jail belladonna jail

Categories Pornstars

Categories Pornstars

Legal

Terms of Service Privacy Statement Statement of Responsibility Notice and Action Policy (Link Removal) DMCA / Copyright Acceptable Content Policy Digital Services Act 2257

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.

© 2025 Pornmd.com. All rights reserved.