Jail Videos - Trans (399)

Prison of Sissy 3 the Pr Manager Fucked

Prison of Sissy 3 the Pr Manager Fucked

FapHouse 1 week ago

Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina

Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina

FapHouse 4 days ago

Road Trip Day 4

51% HD 0:39 / 31:40

Road Trip Day 4

FapHouse 4 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 2 weeks ago

Cocked Behind Bars

48% HD 0:10 / 35:20

Cocked Behind Bars

LoyalFans 4 years ago

DISCIPLINARY ACTION

DISCIPLINARY ACTION

Clips4sale 9 months ago

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

58% 0:11 / 49:57

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

Trannie Visit Pt 2

Trannie Visit Pt 2

Clips4sale 2 years ago

Welcome to Prison, Bitch!!

65% 0:20 / 12:57

Welcome to Prison, Bitch!!

Clips4sale 6 months ago

FUTANARI BDSM BONDAGE Futa girl fucked by a Fucking Machine - Hot BDSM Slave - 3D Hentai - Full HD MP4 1080p

63% HD 0:11 / 10:10

FUTANARI BDSM BONDAGE Futa girl fucked by a Fucking Machine - Hot BDSM Slave - 3D Hentai - Full HD MP4 1080p

Clips4sale 1 year ago

Jesse and Steven Garcia

61% HD 2:03 / 47:31

Jesse and Steven Garcia

KinkTrans 17 years ago

You're going to futa jail

56% HD 0:10 / 11:01

You're going to futa jail

LoyalFans 5 months ago

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

44% HD 0:52 / 38:10

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

KinkTrans 11 years ago

Serving Your Ass to Her Cock to Spring Yourself From Jail

Serving Your Ass to Her Cock to Spring Yourself From Jail

Serving Your Ass to Her Cock to Spring Yourself from Jail

HD 0:42 / 40:31

Serving Your Ass to Her Cock to Spring Yourself from Jail

KinkTrans 11 years ago

Trans Prison

HD 0:30 / 2:35:00

AEBN 6 years ago

Road Trip day 4

39% 0:11 / 31:40

Road Trip day 4

FULL MOVIE A Prisoner in StepDaddys House

46% HD 0:30 / 1:09:16

FULL MOVIE A Prisoner in StepDaddys House

Clips4sale 2 months ago

T Smack Vs Puzziboi!

T Smack Vs Puzziboi!

Clips4sale 11 months ago

Cocked Behind Bars

HD 0:48 / 35:52

Cocked Behind Bars

TransAngels 7 years ago

Steven Sweat and Danielle Foxxx

58% HD 2:08 / 44:48

Steven Sweat and Danielle Foxxx

KinkTrans 18 years ago

Fucked By 2 Shemales

Fucked By 2 Shemales

Sex.com 5 months ago

Aspen Brooks Is Too Pretty For Jail!

60% HD 1:48 / 58:28

Aspen Brooks Is Too Pretty For Jail!

KinkTrans 6 years ago

Prison of Sissy 3 the Pr Manager Fucked

55% 0:39 / 11:09

Prison of Sissy 3 the Pr Manager Fucked

FapHouse 2 weeks ago

Hot anal trans sex prison house fantasies

53% HD 0:39 / 24:27

Hot anal trans sex prison house fantasies

FapHouse 3 years ago

Extreme Anal Fisting in the Swing Elbow Deep by @valentinarosa89, Rose and Prolapse @stretch_events

Extreme Anal Fisting in the Swing Elbow Deep by @valentinarosa89, Rose and Prolapse @stretch_events

FapHouse 7 months ago

Sex with the Prisoner

54% VR 1:30 / 50:45

Sex with the Prisoner

TSVirtualLovers 4 years ago

TS Natassia Dream & Robert Axel in The Prelude to "Super Soldier"

50% 0:11 / 32:45

TS Natassia Dream & Robert Axel in The Prelude to "Super Soldier"

Disciplinary Action

56% 4K 0:30 / 32:13

Disciplinary Action

Clips4sale 5 months ago

Released From Masculine Jail

49% 0:11 / 7:59

Released From Masculine Jail

Clips4sale 2 years ago

TS Mistress Stroka Fucking Part 2

55% 0:11 / 15:31

TS Mistress Stroka Fucking Part 2

Clips4sale 1 year ago

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

49% 0:11 / 45:39

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

PRISON TEMPTATION

66% HD 0:20 / 21:45

PRISON TEMPTATION

Clips4sale 1 year ago

Hung Shemales Yasmin Dornelles and Bruna Ferrari Use Their Burglars Holes

Hung Shemales Yasmin Dornelles and Bruna Ferrari Use Their Burglars Holes

Clips4sale 2 years ago

Prison Break Pegging Part 2

69% HD 0:11 / 5:45

Prison Break Pegging Part 2

Clips4sale 3 years 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 1 year ago

Sandra Gibbons - Trapped in Rubber (mp4 HD 1080)

Sandra Gibbons - Trapped in Rubber (mp4 HD 1080)

Clips4sale 3 months ago

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

66% 0:13 / 9:40

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

Clips4sale 5 months ago

Chastity Prisoner Anal Hooked and Vibed

57% 0:23 / 48:28

Chastity Prisoner Anal Hooked and Vibed

Clips4sale 3 months ago

TS Seduction: Steven Sweat and Danielle Foxxx

HD 0:30 / 44:00

TS Seduction: Steven Sweat and Danielle Foxxx

AEBN 8 years ago

The Horny Police Officer Is Back to Punish You!

66% HD 0:39 / 14:18

The Horny Police Officer Is Back to Punish You!

FapHouse 3 months ago

Prisoner fucked in his cell by Domme and hung trans, left oozing cum (4k version)

66% 4K 0:12 / 15:29

Prisoner fucked in his cell by Domme and hung trans, left oozing cum (4k version)

Clips4sale 1 year ago

Trans Domination

59% HD 0:10 / 12:30

Trans Domination

LoyalFans 1 month ago

Prison Temptation

56% 4K 0:30 / 21:45

Prison Temptation

Futanari 1 year ago

Man Catcher - transformation of her prisoner II *MOV*

HD 0:26 / 16:09

Man Catcher - transformation of her prisoner II *MOV*

Clips4sale 11 months ago

Cellmate

66% 4K 0:30 / 32:40

Futanari 5 months ago

DETAINED AND DRAINED *HD 1080*

HD 0:30 / 16:33

DETAINED AND DRAINED *HD 1080*

Clips4sale 1 year ago

PEGGING NURSES

66% HD 0:30 / 9:46

Clips4sale 3 years ago

* 854x480p * Sissy Closet Queer Caught Thieving Pantyhose - Mp4

49% 0:09 / 14:20

* 854x480p * Sissy Closet Queer Caught Thieving Pantyhose - Mp4

Clips4sale 9 months ago

Man Catcher - shackled sissy maid training *MOV*

66% 4K 0:25 / 10:26

Man Catcher - shackled sissy maid training *MOV*

Clips4sale 10 months ago

Avery Angel BJ Exchange

58% HD 0:11 / 17:06

Avery Angel BJ Exchange

Clips4sale 2 years ago

Sissies Belong In Chastity (HD MP4)

54% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 1 year ago

Sissy Ladyboy Standing Anal in Prison

55% HD 0:39 / 14:28

Sissy Ladyboy Standing Anal in Prison

FapHouse 5 months ago

Steven Sweat and Danielle Foxxx

50% 0:11 / 44:48

Steven Sweat and Danielle Foxxx

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

4K 0:50 / 10:23

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

Clips4sale 1 year ago

classy and submissive

classy and submissive

Clips4sale 3 months ago

You are a Prisoner to your Sissy Porn

HD 0:29 / 11:43

You are a Prisoner to your Sissy Porn

Clips4sale 1 week ago

Her Prisoner - sissy chained and left alone *wmv*

50% 4K 0:25 / 10:40

Her Prisoner - sissy chained and left alone *wmv*

Clips4sale 4 months ago

Sissies in Space 01: Processing The Prisoners

60% HD 0:32 / 17:14

Sissies in Space 01: Processing The Prisoners

Clips4sale 3 years ago

Police young colombian officer fucks a transvestite prisoner in the prison yard outdoors. Lots of bizarre videos on XVideos RED

Premium HD 5:53

Police young colombian officer fucks a transvestite prisoner in the prison yard outdoors. Lots of bizarre videos on XVideos RED

xnxxGold 2 years ago

Her Prisoner Part 24 - Sissy Training VII

63% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 1 year 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 5 months ago

T.S. Hookers 2

HD 0:30 / 1:36:00

AEBN 8 years ago

Dylan transvestites himself to satisfy transgressive sex

Dylan transvestites himself to satisfy transgressive sex

FapHouse 2 weeks ago

Policewoman with a Huge Cock Turns Her Prisoner Into a Dick Slut

58% HD 0:39 / 8:28

Policewoman with a Huge Cock Turns Her Prisoner Into a Dick Slut

FapHouse 4 months ago

Mitch West and Mia Isabella

HD 2:03 / 42:03

Mitch West and Mia Isabella

KinkTrans 17 years ago

arched

Clips4sale 2 years ago

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

4K 0:26 / 10:09

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

Clips4sale 5 months ago

Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina

Prisoner Kanisa Get Punishment From Officer Wei and Officer Reina

FapHouse 4 days ago

BNWO Prisoner Orientation Video

4K 0:26 / 12:53

BNWO Prisoner Orientation Video

Clips4sale 17 hours ago

Hot As Hell : Actors Who Have Played Satan

Premium 55% HD 15:20

Hot As Hell : Actors Who Have Played Satan

Mr. Man 3 years ago

Slut Milking (1080p)

47% HD 0:12 / 15:15

Slut Milking (1080p)

Clips4sale 7 months ago

Her Prisoner - sissy chained and left alone

4K 0:30 / 10:40

Her Prisoner - sissy chained and left alone

Clips4sale 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

FapHouse 2 weeks ago

Steven Sweat and Danielle Foxxx

60% HD 0:39 / 44:48

Steven Sweat and Danielle Foxxx

FapHouse 1 year ago

She-Male Strokers 52

66% HD 0:30 / 2:49:00

She-Male Strokers 52

AEBN 13 years ago

Her Prisoner Part 19 - Her Sissy Slave Maid II **MOV**

56% 4K 0:48 / 10:10

Her Prisoner Part 19 - Her Sissy Slave Maid II **MOV**

Clips4sale 1 year ago

Bastinado and tickling (720p)

Bastinado and tickling (720p)

Clips4sale 3 years ago

Gonna Make Love in This Club - Laela Knight Fucks a Line Jumper

56% 0:11 / 39:51

Gonna Make Love in This Club - Laela Knight Fucks a Line Jumper

Prisoner Put His Dick in the Transvestite Police Officer

HD 0:39 / 13:10

Prisoner Put His Dick in the Transvestite Police Officer

FapHouse 1 year ago

Feminization project prison pussy

38% HD 0:30 / 7:29

Feminization project prison pussy

Clips4sale 7 months 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

TS Seduction: Dorian and Jessica Host

HD 0:30 / 42:00

TS Seduction: Dorian and Jessica Host

AEBN 7 years ago

Suck your New StepDaddy a Prisoner in StepDaddys House Story

55% HD 0:28 / 16:24

Suck your New StepDaddy a Prisoner in StepDaddys House Story

Clips4sale 3 months ago

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

49% 4K 0:33 / 10:09

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

Clips4sale 1 year ago

Uninvited Slumber Party Guest Written by Kylie Gable Narrated by Shayla Aspasia

HD 0:30 / 35:37

Uninvited Slumber Party Guest Written by Kylie Gable Narrated by Shayla Aspasia

Clips4sale 10 months ago

Break In & Pay with Your Pussy: Ts Venus Lux teaches a rookie a Lesson

63% HD 0:10 / 28:38

Break In & Pay with Your Pussy: Ts Venus Lux teaches a rookie a Lesson

LoyalFans 3 years ago

Gonna Make Love in this Club - Laela Knight Fucks a Line Jumper

HD 0:53 / 39:52

Gonna Make Love in this Club - Laela Knight Fucks a Line Jumper

KinkTrans 10 years ago

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

HD 0:39 / 27:51

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

FapHouse 5 years ago

Sissy Punishment Room

Sissy Punishment Room

FapHouse 2 months ago

Caged Lady Meat! A Sexploitation Domination Extravaganza!

55% 0:11 / 23:40

Caged Lady Meat! A Sexploitation Domination Extravaganza!

Wonder Woman Busts Harley Quinn

55% HD 0:34 / 24:10

Wonder Woman Busts Harley Quinn

Clips4sale 3 years ago

Sophia Gets Her Asshole Double-Dicked

63% 4K 1:00 / 39:00

Sophia Gets Her Asshole Double-Dicked

DreamTranny 8 months ago

Trans Prison

HD 0:30 / 2:35:00

AEBN 6 years ago

Nyobi Khan and Rico

HD 0:39 / 59:46

Nyobi Khan and Rico

KinkTrans 17 years ago

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

HD 0:39 / 45:39

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

KinkTrans 12 years ago

Locked Up and Horned Up Part 1

HD 1:09 / 32:46

Locked Up and Horned Up Part 1

TransAngels 3 years 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

Her Prisoner Part 20 - Sissy Training Part III

4K 0:29 / 10:10

Her Prisoner Part 20 - Sissy Training Part III

Clips4sale 1 year ago

Hung Shemales Yasmin Dornelles and Bruna Ferrari Punish a Burglar DT635

Premium HD 39:08

Hung Shemales Yasmin Dornelles and Bruna Ferrari Punish a Burglar DT635

Sheer 1 year ago

Retribution Part 9

HD 0:31 / 14:29

Retribution Part 9

Clips4sale 1 year ago

Bang My Tranny Ass 3

HD 0:30 / 2:07:00

Bang My Tranny Ass 3

AEBN 15 years ago

Private Fox Is Hiding Launch Codes in Her Box

HD 0:39 / 40:15

Private Fox Is Hiding Launch Codes in Her Box

FapHouse 1 month ago

Her Prisoner Part 18 - Her Sissy Slave Maid

4K 0:45 / 10:23

Her Prisoner Part 18 - Her Sissy Slave Maid

Clips4sale 1 year ago

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

HD 0:39 / 46:30

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

FapHouse 1 year ago

beauty warrior at prison - 3d_animation

HD 0:30 / 20:21

beauty warrior at prison - 3d_animation

PornBox 4 months ago

Sandra Gibbons - Trannie Bound with Leather (mp4 HD)

Premium HD 8:07

Sandra Gibbons - Trannie Bound with Leather (mp4 HD)

Clips4sale 11 months ago

You're going to futa jail WMV

HD 0:26 / 11:00

You're going to futa jail WMV

Clips4sale 5 months ago

Police young colombian officer fucks a transvestite prisoner in the prison yard outdoors. Lots of bizarre videos on XVideos RED

Premium HD 5:53

Police young colombian officer fucks a transvestite prisoner in the prison yard outdoors. Lots of bizarre videos on XVideos RED

XVideosRed 2 years ago

Prisoner of the Matriarchy: Warrior Captured And Pegged

Prisoner of the Matriarchy: Warrior Captured And Pegged

Clips4sale 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 2 months 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

unethical prison officers

unethical prison officers

LoyalFans 2 months ago

A Prisoner to Diapers and Sissy Porn

HD 0:29 / 17:13

A Prisoner to Diapers and Sissy Porn

Clips4sale 1 week ago

imprisoned by The Sisterhood: breeding stock for feral futa

39% HD 0:10 / 15:01

imprisoned by The Sisterhood: breeding stock for feral futa

LoyalFans 5 months ago

Sissy School Punishment Room

56% HD 0:29 / 15:31

Sissy School Punishment Room

Clips4sale 2 months ago

3 tranny mistress with 2 prisoners

56% HD 0:39 / 25:56

3 tranny mistress with 2 prisoners

FapHouse 3 years ago

Female Mask Maid Goes to Prison

Female Mask Maid Goes to Prison

Clips4sale 3 years ago

Eating Pussy of a GIANTESS Busty Babe - GIANT Cunnilingus - 3D Hentai - Full HD MP4 1080p

66% HD 0:11 / 8:32

Eating Pussy of a GIANTESS Busty Babe - GIANT Cunnilingus - 3D Hentai - Full HD MP4 1080p

Clips4sale 2 years ago

The Interrogation

70% HD 0:39 / 36:30

The Interrogation

KinkTrans 16 years ago

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