Jail Videos - Trans (551)

Bastinado and tickling

Bastinado and tickling

Clips4sale 3 years ago

Sandra Gibbons - Captive in Leather and Chain (mp4 HD)

Sandra Gibbons - Captive in Leather and Chain (mp4 HD)

Clips4sale 1 year ago

Man Catcher - the punishment collar *MOV*

61% HD 0:22 / 11:30

Man Catcher - the punishment collar *MOV*

Clips4sale 1 year ago

COUNSELOR CARISSAS LEZDOM CRISIS PT2 *HD 720*

63% HD 0:30 / 16:37

COUNSELOR CARISSAS LEZDOM CRISIS PT2 *HD 720*

Clips4sale 1 year ago

Sissies Belong In Chastity (SD MP4)

60% 4K 0:30 / 15:17

Sissies Belong In Chastity (SD MP4)

Clips4sale 2 years ago

He Looks so Sexy with My Big Black Dick in His Little Fuck Hole

HD 0:39 / 39:37

He Looks so Sexy with My Big Black Dick in His Little Fuck Hole

FapHouse 4 months ago

Slut Prison - Made to Crossdress

HD 0:10 / 10:51

Slut Prison - Made to Crossdress

LoyalFans 1 month ago

Big Dick with a Tight Glasses of Handsome Sissy Femboy on a Rubberless Cruise Fuck!

HD 0:39 / 13:51

Big Dick with a Tight Glasses of Handsome Sissy Femboy on a Rubberless Cruise Fuck!

FapHouse 2 months ago

BNWO Prisoner Orientation Video

55% 4K 0:26 / 12:53

BNWO Prisoner Orientation Video

Clips4sale 6 months ago

Anal Bottal Handjob

Anal Bottal Handjob

FapHouse 6 months ago

Trans Teen Grazyeli Silva Toys Ass And Cums In Jail

Premium HD 21:11

Trans Teen Grazyeli Silva Toys Ass And Cums In Jail

Sheer 2 years ago

Dominant Shemale Turns You Into a Cum Dump

Dominant Shemale Turns You Into a Cum Dump

FapHouse 3 months ago

Nylon Pantyhose Encasement Bondage Cocoon | FHD

HD 0:14 / 36:42

Nylon Pantyhose Encasement Bondage Cocoon | FHD

Clips4sale 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

XVideosRed 3 months ago

PEGGING NURSES

68% HD 0:30 / 9:46

Clips4sale 3 years ago

My First Day in Prison: Bathroom Experience

32% HD 0:39 / 7:30

My First Day in Prison: Bathroom Experience

FapHouse 7 months ago

Fat Guy with a Fat Cock Moans and Cums All Over Himself

59% HD 0:39 / 11:00

Fat Guy with a Fat Cock Moans and Cums All Over Himself

FapHouse 6 months ago

PERVERTED FUTANARI COP ARRANGED HARD ANAL SEX AND FACEFUCK FOR A SEXY PRISONER (SIMS + ANIME HENTAI + SFM)

Premium HD 22:01

PERVERTED FUTANARI COP ARRANGED HARD ANAL SEX AND FACEFUCK FOR A SEXY PRISONER (SIMS + ANIME HENTAI + SFM)

Sheer 1 year ago

The big boobs prisoner wants sex

HD 0:39 / 46:13

The big boobs prisoner wants sex

FapHouse 2 years ago

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

HD 1:00 / 11:40

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

Clips4sale 2 years ago

My New Big Anal Toy 2 - Anal Ring

My New Big Anal Toy 2 - Anal Ring

FapHouse 2 years ago

Trans Teen Grazyeli Silva Toys Ass And Cums In Jail

Trans Teen Grazyeli Silva Toys Ass And Cums In Jail

XVideosRed 2 years ago

Giada da Vinci offers LunaFeetCute her only monthly chance to have an orgasm with chastity belt, crossdressing, cock tease, tease&denial, anal masturbation

HD 0:29 / 13:48

Giada da Vinci offers LunaFeetCute her only monthly chance to have an orgasm with chastity belt, crossdressing, cock tease, tease&denial, anal masturbation

Clips4sale 1 year ago

Cuff It Like Beyonce

Cuff It Like Beyonce

FapHouse 1 year ago

Her Prisoner Part 24 - Sissy Training VII

59% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 2 years ago

Hairy Armpits worship

Hairy Armpits worship

Clips4sale 3 years ago

T.S. Hookers 2

HD 0:30 / 1:36:00

AEBN 8 years ago

unethical prison officers

unethical prison officers

LoyalFans 8 months ago

johannesgaming - update #377 - prison of sissy 2 adam used the glory hole not to get a bj but to give - may 28, 2025

johannesgaming - update #377 - prison of sissy 2 adam used the glory hole not to get a bj but to give - may 28, 2025

PornBox 6 months ago

Break In the New Girl

Premium HD 32:02

Break In the New Girl

TransAngels 6 years ago

Sissy Punishment Room

Sissy Punishment Room

FapHouse 8 months ago

Anal Sex

FapHouse 10 months ago

Jesse and Steven Garcia

Premium 61% HD 47:31

Jesse and Steven Garcia

KinkTrans 18 years ago

You're going to futa jail MP4

HD 0:26 / 11:00

You're going to futa jail MP4

Clips4sale 11 months ago

You're going to futa jail

57% HD 0:10 / 11:01

You're going to futa jail

LoyalFans 11 months ago

Hunk Blowjob

FapHouse 9 months ago

Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell

HD 0:39 / 17:52

Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell

FapHouse 10 months ago

Nara offer her slave as a fuck toy for TS Alexia Duucan (1080 EN-sub)

56% HD 0:30 / 20:36

Nara offer her slave as a fuck toy for TS Alexia Duucan (1080 EN-sub)

Clips4sale 8 months 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

Hot anal trans sex prison house fantasies

Hot anal trans sex prison house fantasies

FapHouse 1 year ago

3d sexy dickgirl fucks hard a hot horny blonde in restraints in the sci-fi lab

Premium HD 13:37

3d sexy dickgirl fucks hard a hot horny blonde in restraints in the sci-fi lab

xnxxGold 4 years ago

Serving Your Ass to Her Cock to Spring Yourself From Jail

Serving Your Ass to Her Cock to Spring Yourself From Jail

C4S 2 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

XVideosRed 2 years 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

xnxxGold 3 months ago

Prison Thug Jacks off Huge Big Black Cock

Prison Thug Jacks off Huge Big Black Cock

FapHouse 3 months ago

Female alien in a prison gets fucked hard by a hot dickgirl

Female alien in a prison gets fucked hard by a hot dickgirl

FapHouse 2 months ago

Prisoner Gets Ass Fucked by Guard

Prisoner Gets Ass Fucked by Guard

FapHouse 15 hours ago

POV GIANTESS Alien Girl Fucking - FANTASY SPACE SEX - Femdom Fucks your Soul - 3D Hentai - Full HD MP4 1080p

POV GIANTESS Alien Girl Fucking - FANTASY SPACE SEX - Femdom Fucks your Soul - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

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

HD 0:39 / 46:36

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

FapHouse 2 years ago

Shemale prison guard exchanges hard cock anal with an inmate

Premium HD 28:25

Shemale prison guard exchanges hard cock anal with an inmate

XVideosRed 6 years ago

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

XVideosRed 1 year ago

A Demand for the Cure - Prison of Sissy

A Demand for the Cure - Prison of Sissy

FapHouse 4 months ago

Jailbird Gives His Mouth to Blonde Shemale Prison Guard and Ass to Strap-pn of Assistant District Attorney

Jailbird Gives His Mouth to Blonde Shemale Prison Guard and Ass to Strap-pn of Assistant District Attorney

FapHouse 4 months ago

My Cock Bwlojob

My Cock Bwlojob

FapHouse 4 months ago

Prison of Sissy 4 I Love to Suck Cock

Prison of Sissy 4 I Love to Suck Cock

FapHouse 6 months ago

Diaper Prisoner Orientation for Step-Daddy

Diaper Prisoner Orientation for Step-Daddy

Clips4sale 4 months ago

The Reformatory Part 2

64% 0:19 / 27:40

The Reformatory Part 2

Clips4sale 4 months ago

Vacsuit 1

Clips4sale 3 years ago

GIANTESS VORE Eating Man - GIANT FUTANARI DOMINATION - Hot Babe Jerking off a Huge Dick Devouring a Guy - 3D Hentai - Full HD MP4 1080p

GIANTESS VORE Eating Man - GIANT FUTANARI DOMINATION - Hot Babe Jerking off a Huge Dick Devouring a Guy - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

POV GIANTESS Handjob - GIANT Point of View Handjob - Hot Busty Babe Jerking off your dick - 3D Hentai - Full HD MP4 1080p

POV GIANTESS Handjob - GIANT Point of View Handjob - Hot Busty Babe Jerking off your dick - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

arched

Clips4sale 3 years ago

Johannesgaming - update #377 - Prison of Sissy 2 Adam used the glory hole not to get a bj but to give - May 28, 2025

Johannesgaming - update #377 - Prison of Sissy 2 Adam used the glory hole not to get a bj but to give - May 28, 2025

XVideosRed 6 months ago

Bigg Hunk

FapHouse 6 months ago

Johannesgaming - update #119 - Futa Dating Simulator 11 Ava is a prison bitch will she fuck you or will you fuck her - Jun 27, 2024

Premium HD 32:02

Johannesgaming - update #119 - Futa Dating Simulator 11 Ava is a prison bitch will she fuck you or will you fuck her - Jun 27, 2024

Sheer 1 year ago

You are a Prisoner to your Sissy Porn

HD 0:29 / 11:43

You are a Prisoner to your Sissy Porn

Clips4sale 6 months ago

Sissy Ladyboy Standing Anal in Prison

Premium HD 14:23

Sissy Ladyboy Standing Anal in Prison

Sheer 11 months ago

Still Me and My Landlord Son 5

Still Me and My Landlord Son 5

FapHouse 7 months ago

Hot 3d dickgirl fucks hard a sexy girl in the sci-fi confinement cell

Premium HD 19:12

Hot 3d dickgirl fucks hard a sexy girl in the sci-fi confinement cell

XVideosRed 3 years ago

COUNSELOR CARISSAS LEZDOM CRISIS PT1 *HD 720*

HD 0:29 / 11:02

COUNSELOR CARISSAS LEZDOM CRISIS PT1 *HD 720*

Clips4sale 1 year ago

MILF with Small Tits Ass Fucked and Cummed on Body by Two Big Black Cocks in Prison

HD 0:39 / 13:46

MILF with Small Tits Ass Fucked and Cummed on Body by Two Big Black Cocks in Prison

FapHouse 9 months ago

Sexy woman in latex catsuit bangs a pregnant college girl in prison

66% HD 0:39 / 11:02

Sexy woman in latex catsuit bangs a pregnant college girl in prison

FapHouse 4 years ago

Blonde transsexual prison inmate spends her days masturbating

Blonde transsexual prison inmate spends her days masturbating

XVideosRed 6 years ago

Megi gets ass whipping in a prison

Megi gets ass whipping in a prison

FapHouse 5 years ago

COUNSELOR CARISSAS LEZDOM CRISIS PT2 *HD 1080*

HD 0:30 / 16:37

COUNSELOR CARISSAS LEZDOM CRISIS PT2 *HD 1080*

Clips4sale 2 years ago

TRANSEROTICA Alura Jenson Sandwiched Between Foxxy and Zeb Atlas

Premium HD 32:13

TRANSEROTICA Alura Jenson Sandwiched Between Foxxy and Zeb Atlas

xnxxGold 5 years ago

Man Catcher - his permanent collaring *MOV*

HD 0:21 / 14:07

Man Catcher - his permanent collaring *MOV*

Clips4sale 1 year ago

Sissy Ladyboy Standing Anal in Prison

Premium HD 14:24

Sissy Ladyboy Standing Anal in Prison

xnxxGold 11 months ago

dickgirl ladyboy is fucking girl standing in her prison cell

55% HD 0:30 / 17:47

dickgirl ladyboy is fucking girl standing in her prison cell

PornBox 10 months ago

Girl Sucks Sissy Ladyboy Dick in Prison

Girl Sucks Sissy Ladyboy Dick in Prison

FapHouse 10 months ago

Nara offer her slave as a fuck toy for TS Alexia Duucan (1080 EN-sub)

HD 0:30 / 20:36

Nara offer her slave as a fuck toy for TS Alexia Duucan (1080 EN-sub)

Clips4sale 8 months ago

Sara Gets Let Out of Prison After Days with No Dick

Sara Gets Let Out of Prison After Days with No Dick

FapHouse 10 months ago

Paying My First Debt in Jail - Prison of Sissy

Paying My First Debt in Jail - Prison of Sissy

FapHouse 5 months ago

Shemale Fucks Girl Standing in Bondage Prison Sex

Premium HD 15:53

Shemale Fucks Girl Standing in Bondage Prison Sex

Sheer 10 months ago

Big Cock Belwojob

Big Cock Belwojob

FapHouse 9 months ago

BNWO Snowbunny Diaper Costume for the Party

4K 0:30 / 14:32

BNWO Snowbunny Diaper Costume for the Party

Clips4sale 2 months ago

Stepdaddy Eat My Cum

Stepdaddy Eat My Cum

FapHouse 1 month ago

TATTED HISPANIC JUST OUT OF PRISON FUCKS BLONDE CROSSDRESSER

Premium HD 3:00

TATTED HISPANIC JUST OUT OF PRISON FUCKS BLONDE CROSSDRESSER

xnxxGold 2 months ago

My Mistress In Denim

Premium HD 32:39

My Mistress In Denim

TransAngels 4 years ago

Johannesgaming - update #377 - Prison of Sissy 2 Adam used the glory hole not to get a bj but to give - May 28, 2025

Johannesgaming - update #377 - Prison of Sissy 2 Adam used the glory hole not to get a bj but to give - May 28, 2025

xnxxGold 6 months ago

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

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

FapHouse 3 months ago

Everyone Has a Plan - Prison of Sissy

61% HD 0:39 / 6:19

Everyone Has a Plan - Prison of Sissy

FapHouse 6 months ago

shemale standing fuck ladyboy prison sex

HD 0:30 / 14:13

shemale standing fuck ladyboy prison sex

PornBox 11 months ago

Bastinado and tickling (wmv)

Bastinado and tickling (wmv)

Clips4sale 3 years ago

black guy out of jail fucks tranny&#039_s tight hole

Premium HD 5:01

black guy out of jail fucks tranny&#039_s tight hole

XVideosRed 2 months ago

Young Brazilian Soldier Fucks Two Beautiful Prisoner Outside The Camp

Young Brazilian Soldier Fucks Two Beautiful Prisoner Outside The Camp

XVideosRed 3 years ago

Her Prisoner Part 18 - Her Sissy Slave Maid **MOV**

4K 0:50 / 10:23

Her Prisoner Part 18 - Her Sissy Slave Maid **MOV**

Clips4sale 2 years ago

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

Premium HD 16:34

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

XVideosRed 2 years ago

Trannie Visit Pt 2

66% 0:11 / 8:51

Trannie Visit Pt 2

Clips4sale 3 years ago

Moving her sissy maid from the concrete hole to the cage *MOV*

57% 4K 0:27 / 10:12

Moving her sissy maid from the concrete hole to the cage *MOV*

Clips4sale 1 year ago

NO SIN GOES UNPUNISHED 2 *HD 720*

HD 0:31 / 12:31

NO SIN GOES UNPUNISHED 2 *HD 720*

Clips4sale 1 year ago

Transsexual prison guard strips down to stroke her cock on her break

Transsexual prison guard strips down to stroke her cock on her break

XVideosRed 6 years ago

The show

Clips4sale 3 years ago

Shemale prison guard exchanges hard cock anal with an inmate

Premium HD 28:25

Shemale prison guard exchanges hard cock anal with an inmate

xnxxGold 3 years 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

The Interrogation

Premium 70% HD 36:30

The Interrogation

KinkTrans 17 years 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 11 months ago

Handjob

FapHouse 10 months ago

Trans Prison

HD 0:30 / 2:35:00

AEBN 7 years ago

Transsexual prison guard wants one of her inmates to fuck her tight ass

Premium HD 34:08

Transsexual prison guard wants one of her inmates to fuck her tight ass

XVideosRed 6 years ago

shemale prison

Premium HD 28:25

XVideosRed 6 years ago

stepmom visits virgin in prison pov

HD 0:11 / 10:08

stepmom visits virgin in prison pov

Clips4sale 3 years ago

Straight Guys Who Like Tranny Cock 5

HD 0:30 / 3:51:00

Straight Guys Who Like Tranny Cock 5

AEBN 20 years ago

Sexy prisoner girl gets ass fucked by a guard in prison

HD 0:39 / 22:18

Sexy prisoner girl gets ass fucked by a guard in prison

FapHouse 4 years ago

Amateur Boy Blowjob

Amateur Boy Blowjob

FapHouse 7 months ago

Big Cock Masturbation

Big Cock Masturbation

FapHouse 6 months ago

Humiliation From Rough Sex and Dominant

Humiliation From Rough Sex and Dominant

FapHouse 8 months ago

Big Ass

FapHouse 9 months ago

Cock Webcam

FapHouse 9 months ago

Sissy Ladyboy Standing Anal in Prison

55% HD 0:39 / 14:28

Sissy Ladyboy Standing Anal in Prison

FapHouse 11 months ago

Role-playing As a Prisoner

Role-playing As a Prisoner

Flirt4Free 2 years ago

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