Prison Porn Movies - Trans (4,882)

Nathalia Fontes Is Dominated and Punished in Abandoned Prison

Nathalia Fontes Is Dominated and Punished in Abandoned Prison

XHamster 2 years ago

GenderX - Nadia Love Takes A Massive BBC To Avoid Jail Time

GenderX - Nadia Love Takes A Massive BBC To Avoid Jail Time

XHamster 5 years ago

Bosomy domme tranny sodomized bangs officer

Bosomy domme tranny sodomized bangs officer

Xozilla 7 years ago

Horny Pearl's Futa Cumsplatting Punishment

Horny Pearl's Futa Cumsplatting Punishment

DykeHQ 1 year ago

Venezuelan homie with superb pecker of 23cm munching chicken booty Bogota

Venezuelan homie with superb pecker of 23cm munching chicken booty Bogota

4Gay 2 months ago

I caught my TS girlfriend with my stepmom

I caught my TS girlfriend with my stepmom

Some.Porn 6 months ago

Tgirl guard fucks inmate in office

Tgirl guard fucks inmate in office

Sheshaft 4 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 3 years ago

Am your Hore In Prison

Am your Hore In Prison

TransTube.tv 1 year ago

Jail guard bum sex pummels she-creature inmate

Jail guard bum sex pummels she-creature inmate

PornDR 5 months ago

Spreading My Ass Stance to A Prison Inmate to Seduce Him in Bathroom

Spreading My Ass Stance to A Prison Inmate to Seduce Him in Bathroom

XHamster 4 months ago

”He Had Me Cumming”

”He Had Me Cumming”

Rainblow 1 year ago

Lance Gets Fucked by Jaquelin in Prison

Lance Gets Fucked by Jaquelin in Prison

AShemaleTube 8 years ago

Went to Prison This Morning And She Got Me Out With Her Spouse's Money Just To Poke Her Like This

Went to Prison This Morning And She Got Me Out With Her Spouse's Money Just To Poke Her Like This

GayCK 4 years ago

Drilling Deep in the Prison With Super Sexy Chanel

Drilling Deep in the Prison With Super Sexy Chanel

Tranny.one 4 years 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 3 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 1 year ago

To join their prison gang she needs to be part of their hot lesbian orgy

To join their prison gang she needs to be part of their hot lesbian orgy

XHamster 2 years ago

Jail warden fuck this two horny inmates

Jail warden fuck this two horny inmates

Sheshaft 2 weeks ago

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

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

XHamster 1 year ago

Jail She-male

KeekAss 10 months ago

Aspen Brooks Is Too Pretty for Jail!

Aspen Brooks Is Too Pretty for Jail!

XHamster 1 year ago

Tranny jail: Break In The New Girl - Natalie Mars licking hairy pussy

Tranny jail: Break In The New Girl - Natalie Mars licking hairy pussy

XHand 3 years ago

Venezuelan friend with good cock of 23cm eating chicken ass Bogota

Venezuelan friend with good cock of 23cm eating chicken ass Bogota

XHamster 3 months ago

Gym Jail Bang Frenzy

Gym Jail Bang Frenzy

Some.Porn 1 month ago

Femboy Sucks His Friend's Dick Who Has Just Been Released From Jail

74% HD 1:01 / 7:53

Femboy Sucks His Friend's Dick Who Has Just Been Released From Jail

FapHouse 6 months ago

Alluring tranny in stockings sodomizes a guy in the prison

Alluring tranny in stockings sodomizes a guy in the prison

Tranny.one 9 years ago

”What Happens When a Prisoner Seduces Officer Chanel Santini?”

”What Happens When a Prisoner Seduces Officer Chanel Santini?”

Trashreality 1 year ago

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

64% 0:39 / 45:14

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

FapHouse 1 year ago

Big Cocks in Prison: Amateur Blowjobs in the Dance Hall

Big Cocks in Prison: Amateur Blowjobs in the Dance Hall

GayCK 1 year 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 7 years ago

very hard fuck behind bars

very hard fuck behind bars

Tranny.one 4 years ago

Got Fucked by My Stepmom Bodyguard

Got Fucked by My Stepmom Bodyguard

XHamster 1 year ago

Prison Guard

XHamster 2 months ago

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

XHamster 2 months ago

Trans Prison- Full Movie

Trans Prison- Full Movie

Eporner 5 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 2 years ago

Nympho T-girl Jade Venus Fucks Dirty Female Jailer Kira Noir

Nympho T-girl Jade Venus Fucks Dirty Female Jailer Kira Noir

Eporner 1 year ago

Aimee Lee In Prison

Aimee Lee In Prison

TransTube.tv 1 month ago

The Dancehall Bitch- gay scene in prison 3

The Dancehall Bitch- gay scene in prison 3

GayCK 5 years ago

Kourtney Dash Rides Hard Justice's Cock in Raw Prison Sex Scene

Kourtney Dash Rides Hard Justice's Cock in Raw Prison Sex Scene

BallsNBoobs 3 months ago

Jesse and Steven Garcia

Jesse and Steven Garcia

XHamster 1 year ago

”Fucked Behind Bars”

”Fucked Behind Bars”

IFuckedYourGF 1 year ago

Tgirl India Castelani surprises with her big cock

Tgirl India Castelani surprises with her big cock

XHamster 1 year ago

Alura Jenson vs Jay West

Alura Jenson vs Jay West

Some.Porn 10 months ago

Horny jail guard fucks the new busty TS inmate

Horny jail guard fucks the new busty TS inmate

GayVids 3 months ago

Tgirl TOPs Prison Pounding Bottoms **Warning Rough**

Tgirl TOPs Prison Pounding Bottoms **Warning Rough**

Tranny.one 4 years ago

Jail warden enjoys the ass of sexy new TS inmate

Jail warden enjoys the ass of sexy new TS inmate

Some.Porn 1 week ago

Blonde rookie did DP, officers and sucked at Glory Hole in jail

Blonde rookie did DP, officers and sucked at Glory Hole in jail

XHamster 2 years ago

The Dancehall Bitch- gay scene in prison 8

The Dancehall Bitch- gay scene in prison 8

GayCK 3 years ago

The Enticing Chanel Santini

61% HD 0:30 / 1:34:00

The Enticing Chanel Santini

AEBN 1 month ago

TRANS BEAUTIES - Kourtney Dash Delivers Hard Justice With Raw Prison Sex And A Steamy Cellblock Facial

TRANS BEAUTIES - Kourtney Dash Delivers Hard Justice With Raw Prison Sex And A Steamy Cellblock Facial

ShemaleSin 3 months ago

”What Happens When a Prisoner Seduces Officer Chanel Santini?”

”What Happens When a Prisoner Seduces Officer Chanel Santini?”

LesbianBliss 7 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 11 months ago

Chubby Asian Mistress Anal-fucks a Submissive Plump Red-hair Sissy-boy With her Dildo And Strap-on

Chubby Asian Mistress Anal-fucks a Submissive Plump Red-hair Sissy-boy With her Dildo And Strap-on

AnySex 2 years ago

Cross-Dressing Criminal Gets His Just Deserts

Cross-Dressing Criminal Gets His Just Deserts

GayPorn 2 weeks ago

Vid 20

XHamster 1 year ago

He Cumming

Eporner 1 year ago

Gorgeous Blonde Ebony Ts Parris Does Take Prisoners

Gorgeous Blonde Ebony Ts Parris Does Take Prisoners

PePorn 8 months ago

No Lesbian Action in County Jail: Playgirl Foxxx and Her Giant Knob Screw a Blond Inmate

No Lesbian Action in County Jail: Playgirl Foxxx and Her Giant Knob Screw a Blond Inmate

ShemaleSin 4 months ago

From the jail cell to the t-girl booty

From the jail cell to the t-girl booty

ShemaleSin 4 years ago

Watch three hot shemales enjoy a hardcore prison threesome with a hot tranny

Watch three hot shemales enjoy a hardcore prison threesome with a hot tranny

TrannyMovs 5 months ago

German guy with a tranny fetish fucks and pounds In Prison with his hot tranny friend

German guy with a tranny fetish fucks and pounds In Prison with his hot tranny friend

TrannyMovs 2 months ago

Your crud In Prison

Your crud In Prison

TrannyGem 6 years ago

DEMONS T DOLLS Super-Steamy Trans Escort Jessy Dubai Gets Booty-Fucked Rock-Hard In Prison After Getting Caught (Jaxton Wheeler)

DEMONS T DOLLS Super-Steamy Trans Escort Jessy Dubai Gets Booty-Fucked Rock-Hard In Prison After Getting Caught (Jaxton Wheeler)

TrannyGem 4 years 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 4 years ago

Rosy Pinheiro (Warden Breaking Her Prisoner)

Rosy Pinheiro (Warden Breaking Her Prisoner)

Tranny.one 4 years ago

Prison of Sissy - The 1st Day in Jail

Prison of Sissy - The 1st Day in Jail

ShemaleSin 1 year ago

TS prisoner getting assfucked by jail manager - Lola Morena

TS prisoner getting assfucked by jail manager - Lola Morena

Fapnado 4 years ago

Kelly Ladyboy From Cebu Suck and Fuck Stepdaddy Then Cum and Pee on His Face

49% 0:39 / 15:27

Kelly Ladyboy From Cebu Suck and Fuck Stepdaddy Then Cum and Pee on His Face

FapHouse 1 year ago

shelady Dynasty four - Vignette two

shelady Dynasty four - Vignette two

TrannyGem 6 years ago

Big Ass Deeper Anal Make to the Ass with Full Strength

68% 0:39 / 6:05

Big Ass Deeper Anal Make to the Ass with Full Strength

FapHouse 11 months ago

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

72% HD 1:01 / 16:55

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

FapHouse 1 year ago

Your Whore in Jail

Your Whore in Jail

AShemaleTube 10 years ago

succulent latina sheboy receives pounded In Jail

succulent latina sheboy receives pounded In Jail

TrannyGem 6 years ago

Disciplinary Action

60% 4K 0:25 / 32:13

Disciplinary Action

Futanari 2 years ago

Prison Temptation

56% 4K 0:20 / 21:45

Prison Temptation

Futanari 2 years ago

sissies in prison

sissies in prison

ShemaleSin 5 years ago

Young prisoners Lovers Can't Keep Their Hands Off Each Other

Young prisoners Lovers Can't Keep Their Hands Off Each Other

XHamster 2 months ago

Trans beauty Chanel Santini fucks lawyer to get out of jail

Trans beauty Chanel Santini fucks lawyer to get out of jail

GayCK 1 month ago

Trans prisoner Lola Morena is barebacked

Trans prisoner Lola Morena is barebacked

ShemaleSex 3 weeks ago

Super Thick Shemale Plays with the Dick of Her Prisoner

Super Thick Shemale Plays with the Dick of Her Prisoner

XHamster 1 week ago

Trans Teen Grazyeli Silva Toys Ass And Cums In prison

Trans Teen Grazyeli Silva Toys Ass And Cums In prison

FapHouse 1 year ago

Prison Brake

XHamster 1 year ago

Prison cell mate fucks her ass toy and blows a load

Prison cell mate fucks her ass toy and blows a load

AShemaleTube 2 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 3 years ago

Cock Prisoner Aroma Obsession

HD 0:39 / 14:28

Cock Prisoner Aroma Obsession

FapHouse 1 month ago

Cellmate

65% 4K 0:30 / 32:40

Futanari 1 year ago

Transvestite in stockings fucks blond

Transvestite in stockings fucks blond

Tranny.one 4 years ago

SADISM & MASOCHISM Utter of Blows a load

SADISM & MASOCHISM Utter of Blows a load

4Gay 10 months ago

Dick Smack His Asshole and Watch It Bounce Until It Opens - Starring Dj Buttpussy

Dick Smack His Asshole and Watch It Bounce Until It Opens - Starring Dj Buttpussy

XHamster 7 months ago

Kelly Ladyboy From Cebu Suck and Fuck Stepdaddy Then Cum and Pee on His Face

61% 0:39 / 15:27

Kelly Ladyboy From Cebu Suck and Fuck Stepdaddy Then Cum and Pee on His Face

FapHouse 1 year ago

Futa Prison Cosplay Gay Sex - Mika Ayden & Nata Gold

Futa Prison Cosplay Gay Sex - Mika Ayden & Nata Gold

XHamster 3 weeks ago

Vintage tranny in a prison

Vintage tranny in a prison

AShemaleTube 12 years ago

Older bangs tranny in prison (2019)

Older bangs tranny in prison (2019)

Tranny.one 4 years ago

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

XHamster 1 month ago

Prison Bodybuilder Takes Control Of Sissy Faggyboi

Prison Bodybuilder Takes Control Of Sissy Faggyboi

Eporner 4 months ago

”TRANSSENSUAL Sweaty Gym Seduction”

”TRANSSENSUAL Sweaty Gym Seduction”

IFuckedYourGF 1 month ago

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

70% 1:01 / 45:14

Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers

FapHouse 1 year ago

Trans pirocuda broke the ass of the boy behind bars

57% HD 1:01 / 28:18

Trans pirocuda broke the ass of the boy behind bars

FapHouse 3 years ago

Hot anal trans sex prison house fantasies

Hot anal trans sex prison house fantasies

Tranny.one 2 years ago

Hot anal trans sex prison house fantasies

Hot anal trans sex prison house fantasies

XHamster 2 years ago

Pay up with Your Pussy TS Jackie Woods Fucks a Hot ***

HD 0:39 / 35:11

Pay up with Your Pussy TS Jackie Woods Fucks a Hot ***

FapHouse 1 month ago

C*M*F-074 Crossdresser Anal Perversion Sacrifice of a Hard-on Beautiful Stem Natsufuyuka Decensored

C*M*F-074 Crossdresser Anal Perversion Sacrifice of a Hard-on Beautiful Stem Natsufuyuka Decensored

Eporner 1 year ago

Trans girl in prison [AI Generated]

Trans girl in prison [AI Generated]

AShemaleTube 10 months ago

Gorgeous tranny barebacked hard by her attorney in jail cell

Gorgeous tranny barebacked hard by her attorney in jail cell

MenGem 3 years ago

damsel-fellow In Prison

damsel-fellow In Prison

TransTube.tv 1 year ago

Beautiful sissy in jail needs you

Beautiful sissy in jail needs you

Tranny.one 4 years ago

From Prison to Pussy Release Day Fuck

From Prison to Pussy Release Day Fuck

AShemaleTube 6 years ago

”Screwed Behind Bars”

”Screwed Behind Bars”

TransHero 1 year ago

Big who tight anal taking by big Dick rong slut

Big who tight anal taking by big Dick rong slut

XHamster 1 year ago

Prison of Sissy 3 the Pr Manager Fucked

Prison of Sissy 3 the Pr Manager Fucked

XHamster 1 year ago

Transsexual prison guard Patricia Arruda teases bubble butt and jerks off

Transsexual prison guard Patricia Arruda teases bubble butt and jerks off

XHamster 6 months ago

Prison Heat - A Taste of Freedom

Prison Heat - A Taste of Freedom

Some.Porn 5 months ago

TS Isabella Salvatore Masturbates Alone Just for You

TS Isabella Salvatore Masturbates Alone Just for You

Some.Porn 3 months ago

Shemale inmates and a black guy fuck in a jail

Shemale inmates and a black guy fuck in a jail

Tranny.one 5 years ago

Rachel Meets The Rich Sturdy Black Guy With Huge Monsterous Dick in The Prison Cleaning Room

Rachel Meets The Rich Sturdy Black Guy With Huge Monsterous Dick in The Prison Cleaning Room

XHamster 5 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 2 years 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 year ago

Cop dominates guy in prison

Cop dominates guy in prison

AShemaleTube 9 years ago

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