Jail Tube (3,328)

Avery Angel BJ Exchange

54% HD 0:11 / 17:06

Avery Angel BJ Exchange

Clips4sale 2 years ago

DISCIPLINARY ACTION

DISCIPLINARY ACTION

Clips4sale 9 months ago

Road Trip Day 4

56% HD 1:01 / 31:40

Road Trip Day 4

FapHouse 5 months ago

Classic Shoot: Ts Sasha Strokes & Her TEN Inches of Law and Order

60% 0:11 / 49:57

Classic Shoot: Ts Sasha Strokes & Her TEN Inches of Law and Order

C4S 2 years ago

TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee

TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee

xHamster 1 year ago

Jesse and Steven Garcia

61% HD 2:03 / 47:31

Jesse and Steven Garcia

KinkTrans 17 years ago

Hot Trans Wife Kellie Shaw Ass Fucked While Husband's In Jail

Hot Trans Wife Kellie Shaw Ass Fucked While Husband's In Jail

LoveTranSex 6 months ago

Trans Prison- Full Movie

Trans Prison- Full Movie

Eporner 3 years ago

Horny guy pounds gorgeous Tgirls tight ass in jail

Horny guy pounds gorgeous Tgirls tight ass in jail

Sheshaft 7 years ago

Trans prisoner Natalie Mars anal toyed

Trans prisoner Natalie Mars anal toyed

Love4Porn 3 years ago

Amateur Bodybuilder vs. Faggyboi: Prison Sissy 4

Amateur Bodybuilder vs. Faggyboi: Prison Sissy 4

GayCK 3 years ago

Prison cell mate fucks her ass toy and blows a load

Prison cell mate fucks her ass toy and blows a load

aShemaleTube 1 year ago

Busty latina teen suspect punish fucked by a LP officer

Busty latina teen suspect punish fucked by a LP officer

ALOTPorn 6 years ago

TS Seduction: Steven Sweat and Danielle Foxxx

64% HD 0:30 / 44:00

TS Seduction: Steven Sweat and Danielle Foxxx

AEBN 8 years ago

Dominant Ebony tranny Kortney Dash fucks a prisoner through the cage

Dominant Ebony tranny Kortney Dash fucks a prisoner through the cage

XCafe 2 months ago

TG Jail three

TrannyGem 4 years ago

Tranny nun punishing anal male prisoner

Tranny nun punishing anal male prisoner

aShemaleTube 6 years ago

Jailhouse shetwink

Jailhouse shetwink

TransTube.tv 3 months ago

Black Prison Thug Dominates White Fat Tranny

Black Prison Thug Dominates White Fat Tranny

Eporner 10 months ago

IMPLANTED: CONVICT ON PAROLE - Hung Aussie Breeds Sissy with Dick Implant

IMPLANTED: CONVICT ON PAROLE - Hung Aussie Breeds Sissy with Dick Implant

TrannyGem 6 years ago

Locked Up And Horned Up - busty ebony Kira Noir ass fucking shemale babe with strapon in jail

Locked Up And Horned Up - busty ebony Kira Noir ass fucking shemale babe with strapon in jail

Xtits 11 months ago

Sissy Anal invasion Super-bitch Locked Down on Giant Fake penis One Pub Jail Trussed & Taunted in Innocence Box by Dominatrix

Sissy Anal invasion Super-bitch Locked Down on Giant Fake penis One Pub Jail Trussed & Taunted in Innocence Box by Dominatrix

TransTube.tv 1 month ago

Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out by valentinarosa89

Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out by valentinarosa89

xHamster 7 months ago

Jail Guard Fucks Blonde Inmate After FUTA Transformation Ends With Huge Facial TRAILER

Jail Guard Fucks Blonde Inmate After FUTA Transformation Ends With Huge Facial TRAILER

ThePornstar 2 months ago

T.S. Hookers 2

HD 0:30 / 1:36:00

AEBN 8 years ago

Your Whore in Jail

Your Whore in Jail

aShemaleTube 9 years ago

Sissy Anal Invasion Fuckslut Locked Down on Giant Fake Penis One Pub Jail Strapped & Taunted in Virginity Box by Domme

Sissy Anal Invasion Fuckslut Locked Down on Giant Fake Penis One Pub Jail Strapped & Taunted in Virginity Box by Domme

TrannyGem 2 years ago

Reality Prison Sex: Locked Up And Horned Up Part 3 - Latina T-girl Lola Morena

Reality Prison Sex: Locked Up And Horned Up Part 3 - Latina T-girl Lola Morena

XHand 1 year ago

Ts Jail Guard Pokes An Inmate

Ts Jail Guard Pokes An Inmate

KeekAss 3 years ago

Busty Asian TS lingerie MILF gets anally banged in prison

Busty Asian TS lingerie MILF gets anally banged in prison

TrannyGem 2 years ago

Giulia Furacao fucked hard with the Wheelchair-bound RD

Giulia Furacao fucked hard with the Wheelchair-bound RD

xHamster 2 months ago

TS Gal Amy Daly Cheers A Guy Up With Sex

TS Gal Amy Daly Cheers A Guy Up With Sex

Sheshaft 2 years ago

Trannie Visit Pt 2

Trannie Visit Pt 2

Clips4sale 2 years ago

Your crud In Prison

Your crud In Prison

TrannyGem 5 years ago

Twistys- Preppy Alex Grey gets screwed! hard inside prison by african Honey Gold

Twistys- Preppy Alex Grey gets screwed! hard inside prison by african Honey Gold

Love4Porn 2 years ago

Shemale Chanel Santini fucks dude in the jail

Shemale Chanel Santini fucks dude in the jail

XHand 3 years ago

two hawt brunettes tears up With lad In The Prison

two hawt brunettes tears up With lad In The Prison

TransTube.tv 2 months ago

Prison Guard Barbie Rous Got Her Holes Stretched By Real Futanari Ashby Winter in a Cell

Prison Guard Barbie Rous Got Her Holes Stretched By Real Futanari Ashby Winter in a Cell

Xfeed 1 year ago

Nathalia Fontes Is Dominated and Punished in Abandoned Prison

Nathalia Fontes Is Dominated and Punished in Abandoned Prison

xHamster 1 year ago

He Had Me Cumming

He Had Me Cumming

StarWank 6 months ago

Brunette Tranny wants dildo in ass and blowjob, Break In The New Girl part 2 - Laila Delight

Brunette Tranny wants dildo in ass and blowjob, Break In The New Girl part 2 - Laila Delight

XHand 1 year ago

Your Whore in Jail

Your Whore in Jail

Tranny.one 3 years ago

Beautiful sissy in jail needs you

Beautiful sissy in jail needs you

Tranny.one 3 years ago

Jail Birds

TrannyGem 6 years ago

Tgirl India Castelani surprises with her big cock

Tgirl India Castelani surprises with her big cock

xHamster 9 months ago

BDSM Full of Cums

BDSM Full of Cums

xHamster 2 months ago

Shemale babe and her ebony lesbian prison guard - Locked Up And Horned Up Part 1 - Kira Noir delievers strapon anal

Shemale babe and her ebony lesbian prison guard - Locked Up And Horned Up Part 1 - Kira Noir delievers strapon anal

Xtits 1 year ago

Locked Up And Horned Up Part 3 - Lola Morena ass fucked by detective officer in interrogation room

Locked Up And Horned Up Part 3 - Lola Morena ass fucked by detective officer in interrogation room

Xtits 11 months ago

Big dick t-girl anal fucks little man

Big dick t-girl anal fucks little man

Sheshaft 4 years ago

Passionate sex with a tranny in a prison

Passionate sex with a tranny in a prison

aShemaleTube 14 years ago

Femboy gives it up to jail guard

Femboy gives it up to jail guard

AbTranny 5 years ago

Transsexual prison guard Patricia Arruda teases bubble butt and jerks off - HoneyTrans

Transsexual prison guard Patricia Arruda teases bubble butt and jerks off - HoneyTrans

Xshemale 3 years ago

my pretty pussy and feet in prison

my pretty pussy and feet in prison

xHamster 4 months ago

Aimee Lee In Jail

Aimee Lee In Jail

Transvids.tv 6 months ago

Lola Jail Guard

Lola Jail Guard

TrannyGem 4 years ago

Wood Greedy TRANSSEXUAL Officer Drika Lima Lets The Prisoner Ravage Her Arse

Wood Greedy TRANSSEXUAL Officer Drika Lima Lets The Prisoner Ravage Her Arse

KeekAss 2 years ago

Pulling Rank: Dirty Hot Cop Melanie Brooks Fucks Evidence Room Boy

Pulling Rank: Dirty Hot Cop Melanie Brooks Fucks Evidence Room Boy

xHamster 2 months ago

Private Fox Is Hiding Launch Codes In Her Box

66% HD 0:10 / 34:15

Private Fox Is Hiding Launch Codes In Her Box

LoyalFans 4 years ago

sissies in prison

sissies in prison

ShemaleSin 4 years ago

very hard fuck behind bars

very hard fuck behind bars

Tranny.one 3 years ago

Lance Gets Fucked by Jaquelin in Prison

Lance Gets Fucked by Jaquelin in Prison

aShemaleTube 6 years ago

Cruel shemale Mistress humiliates a dude in a prison cell

Cruel shemale Mistress humiliates a dude in a prison cell

Tranny.one 8 years ago

Tranny babe dominated in the prison

Tranny babe dominated in the prison

aShemaleTube 12 years ago

The Sex Prisoner

The Sex Prisoner

getTranny 9 months ago

TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Dream Prisoner Kimberlee

TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Dream Prisoner Kimberlee

TransVibe 10 months ago

DevilsGangbangs - Sexsual Shani Reid Gets An Butt Cumshot After A hot double penetration

DevilsGangbangs - Sexsual Shani Reid Gets An Butt Cumshot After A hot double penetration

Love4Porn 2 years ago

TransAngels: Humid & beefy oily voluptuous smooching

TransAngels: Humid & beefy oily voluptuous smooching

Transvids.tv 1 month ago

weird German Basement Transvestite rosy pucker penetrate In Prison

weird German Basement Transvestite rosy pucker penetrate In Prison

TrannyGem 4 years ago

DL Prison Dad Bangs me like a Inexperienced Doxy

DL Prison Dad Bangs me like a Inexperienced Doxy

ShemaleSin 4 years ago

Submissive Bimbo Get Nasty Facial Cummed

Submissive Bimbo Get Nasty Facial Cummed

Love4Porn 3 years ago

Horny t-girl cops squad arrest a horny dude and decide to fuck him through his ass instead

Horny t-girl cops squad arrest a horny dude and decide to fuck him through his ass instead

Sheshaft 5 years ago

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

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

xHamster 1 month ago

BDSM Full of Cums

BDSM Full of Cums

xHamster 7 months ago

Black cutie Jasminy Villar gets arrested then drilled by TS Panter Cat and the prison guard (Promo Video for ALT036)

Black cutie Jasminy Villar gets arrested then drilled by TS Panter Cat and the prison guard (Promo Video for ALT036)

ShemaleSin 11 months ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 7 years ago

18 bimbo gets her freedom by fucking 2 hung mall cops

18 bimbo gets her freedom by fucking 2 hung mall cops

Hoes.tube 3 years ago

Detective Yasmin Lee fucks prisoner

Detective Yasmin Lee fucks prisoner

aShemaleTube 6 months ago

transgirl pummels Prisoner In Jail Cage

transgirl pummels Prisoner In Jail Cage

TrannyGem 5 years ago

Tranny Inmate Ass fucked: Locked Up And Horned Up - Lola Morena

Tranny Inmate Ass fucked: Locked Up And Horned Up - Lola Morena

XHand 1 year ago

The Dancehall Bitch- gay scene in prison 8

The Dancehall Bitch- gay scene in prison 8

GayCK 2 years ago

He Came Fumbling This N Ig Ga Along the Pubic hair Path and Got Screwed

He Came Fumbling This N Ig Ga Along the Pubic hair Path and Got Screwed

4Gay 3 months ago

Tranny Bangs Hotty Standing in Servitude Prison Sex

Tranny Bangs Hotty Standing in Servitude Prison Sex

ShemaleSin 1 week ago

He Cumming

Eporner 2 months ago

Hot anal trans sex prison house fantasies

Hot anal trans sex prison house fantasies

TransVibe 8 months ago

Shemale babe and her ebony lesbian prison guard - Locked Up And Horned Up Part 1 - Kira Noir delievers strapon anal

Shemale babe and her ebony lesbian prison guard - Locked Up And Horned Up Part 1 - Kira Noir delievers strapon anal

Tranny.one 1 year ago

Akanes Hot Fuck Session - TGirlJapanHardcore

Akanes Hot Fuck Session - TGirlJapanHardcore

AbTranny 5 years ago

ts prison nurse shemale sasha strokes takes hard anal pounding

ts prison nurse shemale sasha strokes takes hard anal pounding

PornOne 1 month ago

3D Futa Prison Stories

3D Futa Prison Stories

Eporner 7 months ago

How much schlong can a dong sucker suck when a knob sucker suck a shlong ?

How much schlong can a dong sucker suck when a knob sucker suck a shlong ?

ShemaleSin 3 years ago

Prison of Sissy: The First Friend

Prison of Sissy: The First Friend

xHamster 2 months ago

Fleeing Trans Inmate Kendall Penny Gives Cops the Slip

Fleeing Trans Inmate Kendall Penny Gives Cops the Slip

Jizzberry 1 year ago

Shemale Porn Video Alura Jenson Fucked By Trans In Jail

Shemale Porn Video Alura Jenson Fucked By Trans In Jail

Tranny.one 8 months ago

Texas Jail Group Member just out of the Joint at my Gloryhole

Texas Jail Group Member just out of the Joint at my Gloryhole

GayCK 5 years ago

Interracial Prison Twink

Interracial Prison Twink

Eporner 8 years ago

Lucky Dude Got Surprised With Hard Sex And A Blowjob By Lana Knight

Lucky Dude Got Surprised With Hard Sex And A Blowjob By Lana Knight

BeMyHole 1 year ago

TRANNY ANGELS Tranny officer seduces fresh prisoner

TRANNY ANGELS Tranny officer seduces fresh prisoner

TransHero 2 years ago

DL Prison Dad Screws Me Like a Naive Bitch

DL Prison Dad Screws Me Like a Naive Bitch

ShemaleSin 4 years ago

Fernanda Zocal fucks her prisoner Max Scar

Fernanda Zocal fucks her prisoner Max Scar

Tranny.one 5 years ago

My prison bitch

My prison bitch

Tranny.one 3 years ago

Screwed Behind Bars

Screwed Behind Bars

TransHero 8 months ago

Alyssa Prison

TrannyGem 4 years ago

Prison of Sissy - The 1st Day in Jail

Prison of Sissy - The 1st Day in Jail

ShemaleSin 2 months ago

The huge melons prisoner wants sex

The huge melons prisoner wants sex

CrazyPorn 2 years ago

Jail guard is intensely drilled by a stiff tranny cock

Jail guard is intensely drilled by a stiff tranny cock

Tranny.one 7 years ago

DEVILS T GIRLS - Hot Trans Hooker Jessy Dubai Gets Assfucked Hard In Jail After Getting Caug

DEVILS T GIRLS - Hot Trans Hooker Jessy Dubai Gets Assfucked Hard In Jail After Getting Caug

aShemaleTube 3 years ago

Alura Jenson Fucked By Trans In Jail

Alura Jenson Fucked By Trans In Jail

BeMyHole 11 months ago

Shemale Inmates Ass Fucking Each Other After SHower - Locked Up And Horned Up Part 2 - Jade Venus

Shemale Inmates Ass Fucking Each Other After SHower - Locked Up And Horned Up Part 2 - Jade Venus

Xtits 11 months ago

Shemale Officer Fucks Hot Pearl In Prison With A Big Dick - Rough Sex Futa Cumshots TRAILER

Shemale Officer Fucks Hot Pearl In Prison With A Big Dick - Rough Sex Futa Cumshots TRAILER

BallsAndBoobs 6 months ago

Transsexual Prison Guard Fucks An Inmate

Transsexual Prison Guard Fucks An Inmate

xHamster 3 years ago

Guy will get out of prison only if he serves the dick of tranny cop Drika Lima well

Guy will get out of prison only if he serves the dick of tranny cop Drika Lima well

AnySex 1 year ago

Weekend Jail Time in an All Girl Cell and Her Bunk Mate has a Cock

45% HD 0:52 / 38:10

Weekend Jail Time in an All Girl Cell and Her Bunk Mate has a Cock

KinkTrans 11 years ago

Prisoner Put His Dick in the Transvestite Police Officer

Prisoner Put His Dick in the Transvestite Police Officer

xHamster 1 year ago

Hot anal trans sex prison house fantasies

53% HD 0:39 / 24:27

Hot anal trans sex prison house fantasies

FapHouse 4 years ago

He Had Me Cumming

He Had Me Cumming

Fapnow 7 months ago

Transvestite in stockings fucks blond

Transvestite in stockings fucks blond

XXXShemalePorn 6 years ago

Lesbian milf guard uses her power to make the blonde suck her clit and finger her shaved pussy

Lesbian milf guard uses her power to make the blonde suck her clit and finger her shaved pussy

xHamster 2 years ago

Curvy TS Prison Guard Drika Lima Rides Inmates Cock and Cums in His Mouth

Curvy TS Prison Guard Drika Lima Rides Inmates Cock and Cums in His Mouth

aShemaleTube 4 years ago

Prisons Super chick - Audio Sensual ASMR Porn

Prisons Super chick - Audio Sensual ASMR Porn

Love4Porn 4 years ago

Strap It Up, Suck Me Dry

Strap It Up, Suck Me Dry

Hoes.tube 2 weeks ago

StepMommy Wants Her Babyboy POV Virtual Sex Cumshot 10

StepMommy Wants Her Babyboy POV Virtual Sex Cumshot 10

4KPorn 1 year ago

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3,328 results found

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