Jail Tube (3,866)

Steven Sweat and Danielle Foxxx

Steven Sweat and Danielle Foxxx

xHamster 1 year ago

Trans Prison- Full Movie

Trans Prison- Full Movie

Eporner 4 years ago

Sissies Belong In Chastity (4KUHD MP4)

HD 0:30 / 15:17

Sissies Belong In Chastity (4KUHD MP4)

Clips4sale 1 year ago

two hawt brunettes tears up With lad In The Prison

two hawt brunettes tears up With lad In The Prison

TransTube.tv 5 months ago

Lance Gets Fucked by Jaquelin in Prison

Lance Gets Fucked by Jaquelin in Prison

aShemaleTube 7 years ago

Screwed Behind Bars

Screwed Behind Bars

Fapnow 8 months ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 8 years ago

Banged Behind Bars

HD 0:40 / 19:10

Banged Behind Bars

TransAngels 1 year 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 1 year ago

Steven Sweat and Danielle Foxxx

64% HD 0:39 / 44:48

Steven Sweat and Danielle Foxxx

FapHouse 1 year ago

Prison Slave Submitting to Female Dominance — Transgender Domination — Anal👌 Gape Play — ASMR Orgasms

Prison Slave Submitting to Female Dominance — Transgender Domination — Anal👌 Gape Play — ASMR Orgasms

SexPester 5 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 2 years ago

Alyssa Prison

TrannyGem 5 years ago

Strict female guard sissyfies and strapon fucks the smooth prisoner

Strict female guard sissyfies and strapon fucks the smooth prisoner

Tranny.one 3 years ago

Private Fox Is Hiding Launch Codes in Her Box

54% HD 1:01 / 40:15

Private Fox Is Hiding Launch Codes in Her Box

FapHouse 4 months 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

Big butt TS Jessica ass fucks a submissive prison bitch

Big butt TS Jessica ass fucks a submissive prison bitch

Tranny.one 7 years ago

TS Seduction: Steven Sweat and Danielle Foxxx

63% HD 0:30 / 44:00

TS Seduction: Steven Sweat and Danielle Foxxx

AEBN 8 years ago

Your Whore in Jail

Your Whore in Jail

aShemaleTube 9 years ago

Jail taskmaster

Jail taskmaster

2BGay 6 months 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 5 months 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

Large Tits Shemale Guard Dominates Young Male Prisoner

Large Tits Shemale Guard Dominates Young Male Prisoner

DykeHQ 2 months ago

Best Outdoor Scene of the Year 9 Tops Vs Part 2

Best Outdoor Scene of the Year 9 Tops Vs Part 2

xHamster 1 week 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 8 months ago

Rosy Pinheiro (Warden Breaking Her Prisoner)

Rosy Pinheiro (Warden Breaking Her Prisoner)

Tranny.one 3 years ago

Ruckus just got out of jail and is feeling frisky, TS Foxxy is his hot Stepmom and he takes a fancy to her.

Ruckus just got out of jail and is feeling frisky, TS Foxxy is his hot Stepmom and he takes a fancy to her.

TransVibe 1 year 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

xHamster 3 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

Horny guy pounds gorgeous Tgirls tight ass in jail

Horny guy pounds gorgeous Tgirls tight ass in jail

Sheshaft 7 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

RawFTM- Fuck my FTM Pussy like we did in Prison

RawFTM- Fuck my FTM Pussy like we did in Prison

BoyFriendTV 1 year ago

Attractive tranny cop investigates a suspect with her hard cock

Attractive tranny cop investigates a suspect with her hard cock

Tranny.one 8 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

sissies in prison

sissies in prison

ShemaleSin 4 years ago

Young Japanese woman has sex in prison with prison guard, she squirts when he fucks her with his fingers

Young Japanese woman has sex in prison with prison guard, she squirts when he fucks her with his fingers

Tranny.one 2 years ago

Detained Latina tranny ass fingered during interrogation - Locked Up And Horned Up Part 3 with Lola Morena

Detained Latina tranny ass fingered during interrogation - Locked Up And Horned Up Part 3 with Lola Morena

Xtits 2 years ago

Shemale fucks tied guy in jail

Shemale fucks tied guy in jail

aShemaleTube 13 years ago

Tranny fucks hairy soldier in bdsm

Tranny fucks hairy soldier in bdsm

Sheshaft 6 years ago

Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee

Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee

BeMyHole 9 months ago

Aimee Lee In Jail

Aimee Lee In Jail

Transvids.tv 9 months ago

Jail guard is intensely drilled by a stiff tranny cock

Jail guard is intensely drilled by a stiff tranny cock

Tranny.one 8 years ago

Femboy gives it up to jail guard

Femboy gives it up to jail guard

AbTranny 5 years ago

Anal Prison Break - Fetish Roleplay with Transgender Model Yasmine Lee

Anal Prison Break - Fetish Roleplay with Transgender Model Yasmine Lee

Love4Porn 1 month ago

TG Jail three

TrannyGem 4 years ago

Jail shemale fuck

Jail shemale fuck

aShemaleTube 9 years ago

Locked Up and Horned Up Part 1

62% HD 1:09 / 32:46

Locked Up and Horned Up Part 1

TransAngels 3 years 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 6 years ago

The extroverted boy's first day in a maximum security prison.

The extroverted boy's first day in a maximum security prison.

xHamster 2 months ago

Bosomy domme tranny sodomized bangs officer

Bosomy domme tranny sodomized bangs officer

Xozilla 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 1 year ago

prison boy sucks tranny greedy giant cock

prison boy sucks tranny greedy giant cock

xHamster 2 years ago

Real-Life Futanari Tiffany Tatum Stretches Hot Pearl Holes

Real-Life Futanari Tiffany Tatum Stretches Hot Pearl Holes

Xfeed 1 year ago

He Cumming

Eporner 5 months ago

NO Lesbo Action in County Jail Honey Foxxx and her Massive Cock Fuck a Blonde Inmate

NO Lesbo Action in County Jail Honey Foxxx and her Massive Cock Fuck a Blonde Inmate

AbTranny 11 years ago

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

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

xHamster 1 year ago

American huge slut sex hot again xvideos

American huge slut sex hot again xvideos

xHamster 5 months ago

Road Trip Day 4

Road Trip Day 4

xHamster 5 months ago

Your Whore in Jail

Your Whore in Jail

Tranny.one 3 years ago

Rosy Pinheiro (Warden Breaking Her Prisoner)

Rosy Pinheiro (Warden Breaking Her Prisoner)

BeMyHole 4 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

Jenna Ivory Gets Screwed By Her Ebony Lesbo Cellmates (Amber Star, Monique Symone, Chanell Heart)

Jenna Ivory Gets Screwed By Her Ebony Lesbo Cellmates (Amber Star, Monique Symone, Chanell Heart)

Ebony8 1 year ago

Dominant Ebony tranny Kortney Dash fucks a prisoner through the cage

Dominant Ebony tranny Kortney Dash fucks a prisoner through the cage

XCafe 4 months ago

Aimee Lee in Jail

Aimee Lee in Jail

Tranny.one 3 years ago

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

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

xHamster 2 months ago

Stunning tranny Bia Gaucha is taken prisoner and gets fucked

Stunning tranny Bia Gaucha is taken prisoner and gets fucked

xHamster 1 month ago

Shemale prisoner anal fucks guard

Shemale prisoner anal fucks guard

Sheshaft 6 years ago

Alura Jenson Fucked By Trans In Jail

Alura Jenson Fucked By Trans In Jail

BeMyHole 1 year ago

Shemale gets punished in the prison

Shemale gets punished in the prison

aShemaleTube 13 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 4 months ago

Prison sex with a classic tranny bitch

Prison sex with a classic tranny bitch

SexTVX 6 years ago

Sissy Ladyboy Standing Anal In Prison

Sissy Ladyboy Standing Anal In Prison

AniPorn 8 months ago

Sex with tranny in a jail

Sex with tranny in a jail

Tranny.one 3 years ago

chinese Jail gang-intercourse

chinese Jail gang-intercourse

TrannyGem 6 years ago

Pipers Prison Pal

Pipers Prison Pal

Some.Porn 2 months 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

big dick shemale fucks prisoner

big dick shemale fucks prisoner

Eporner 3 years ago

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

48% HD 0:52 / 38:10

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

KinkTrans 12 years ago

Jail Birds

TrannyGem 6 years ago

Petite bazookas black steals a dog leash and the officer stripsearches her and puts it on her as a collar.This chab dominates her to give him a bj and bangs her

Petite bazookas black steals a dog leash and the officer stripsearches her and puts it on her as a collar.This chab dominates her to give him a bj and bangs her

Ebony8 3 weeks ago

Interracial Prison Twink

Interracial Prison Twink

Eporner 9 years ago

Prison Thug Fucks White Little cock Fat Tranny

Prison Thug Fucks White Little cock Fat Tranny

DrTuber 4 years ago

He Had Me Cumming

He Had Me Cumming

4Wank 6 months ago

mariah prison

TrannyGem 5 years ago

DIe Masche mit dem Schlitz (1980, classic German)

DIe Masche mit dem Schlitz (1980, classic German)

Love4Porn 4 years ago

Tgirl prison guard Patricia Arruda teases bubble ass and jerks off

Tgirl prison guard Patricia Arruda teases bubble ass and jerks off

Lesbian8 3 weeks ago

Sultry trans prostitute fucks a prisoner

Sultry trans prostitute fucks a prisoner

XXXShemalePorn 2 years ago

Prisoner Kendall Penny In POV

Prisoner Kendall Penny In POV

BeMyHole 4 years ago

Prisoner Put His Dick in the Transvestite Police Officer

61% HD 1:01 / 13:10

Prisoner Put His Dick in the Transvestite Police Officer

FapHouse 1 year ago

Passionate sex with a tranny in a prison

Passionate sex with a tranny in a prison

AmateurTVx 6 years ago

Nympho t-girl Jade Venus fucks dirty female jailer Kira Noir

Nympho t-girl Jade Venus fucks dirty female jailer Kira Noir

Fapnado 3 years ago

Latina shemale prison guard fucks her inmate

Latina shemale prison guard fucks her inmate

xHamster 4 months ago

Two Gay crossdressers fucked in jail -WickedWhims

Two Gay crossdressers fucked in jail -WickedWhims

xHamster 1 year 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

Shemale Fucking In Jail

Shemale Fucking In Jail

Sheshaft 11 years ago

Two hot brunettes fucks with guy in the prison

Two hot brunettes fucks with guy in the prison

aShemaleTube 11 years ago

Trans Angels - Muscly Kimberlee wanking romp vignette

Trans Angels - Muscly Kimberlee wanking romp vignette

TrannyGem 4 years ago

prison sex with her cellmate for a big cock black tgirl

prison sex with her cellmate for a big cock black tgirl

PornOne 8 months ago

Shemale prison guard Alessia Barbosa sex

Shemale prison guard Alessia Barbosa sex

xHamster 1 year ago

TS prisoner getting assfucked by jail manager - Lola Morena

TS prisoner getting assfucked by jail manager - Lola Morena

Fapnado 3 years ago

webcam shemale masturbating fato cock

webcam shemale masturbating fato cock

TransVibe 1 year ago

Trans prisoner Natalie Mars anal toyed

Trans prisoner Natalie Mars anal toyed

Love4Porn 3 years ago

Agatha Vega Tg Prison Fuck - Horny Shemale Detective Gets Blowjob from Latina Girl

Agatha Vega Tg Prison Fuck - Horny Shemale Detective Gets Blowjob from Latina Girl

PornFreeNow 1 month ago

A white tranny gets shared between two black shemale cops. 3D

A white tranny gets shared between two black shemale cops. 3D

Analdin 6 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

pegging a strap on love story

pegging a strap on love story

BDSMDoe 3 weeks ago

A Demand for The Cure - Prison of Sissy

A Demand for The Cure - Prison of Sissy

xHamster 4 months ago

Jail house she twink

Jail house she twink

TrannyGem 5 years ago

Drilling Deep in the Prison With Super Sexy Chanel

Drilling Deep in the Prison With Super Sexy Chanel

Tranny.one 3 years ago

Big cock shemale anal fucks little man

Big cock shemale anal fucks little man

SexTVX 5 years ago

helpless is my favorite feeling porn video

helpless is my favorite feeling porn video

MyGrowl 1 month ago

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Hot TS jailer punishes the sexy guy as she penetrates her huge cock deep in his ass

Tranny.one 3 years 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 1 year ago

Aimee - Teenage Black Shegirl in Jail

Aimee - Teenage Black Shegirl in Jail

TrannyGem 6 years ago

My prison bitch

My prison bitch

Tranny.one 3 years 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

Alessia barbosa: ladyboy prison guard fucks an inmate

Alessia barbosa: ladyboy prison guard fucks an inmate

XXXShemalePorn 2 years ago

cherrypimps - lauren phillips strapon potpourri ready to dominate porn video

cherrypimps - lauren phillips strapon potpourri ready to dominate porn video

MyGrowl 1 month ago

Big Cocks in Prison: Amateur Blowjobs in the Dance Hall

Big Cocks in Prison: Amateur Blowjobs in the Dance Hall

GayCK 11 months ago

Transvestite in stockings fucks blond

Transvestite in stockings fucks blond

Tranny.one 3 years ago

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3,866 results found

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