Jail Videos - Trans (406)

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

49% HD 0:52 / 38:10

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

KinkTrans 12 years ago

Cellmate

58% 4K 0:30 / 32:40

Futanari 6 months ago

Prison Sissy Cock Sucker part 1

Prison Sissy Cock Sucker part 1

Clips4sale 4 years ago

Sissies Belong In Chastity (4KUHD MP4)

HD 0:30 / 15:17

Sissies Belong In Chastity (4KUHD MP4)

Clips4sale 1 year ago

Sissy School Punishment Room

58% HD 0:29 / 15:31

Sissy School Punishment Room

Clips4sale 3 months ago

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

62% 0:11 / 49:57

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

C4S 2 years ago

perverted futanari cop arranged hard anal sex and facefuck for a sexy prisoner (sims + anime hentai + sfm)

HD 5:00 / 22:01

perverted futanari cop arranged hard anal sex and facefuck for a sexy prisoner (sims + anime hentai + sfm)

PornBox 8 months ago

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

45% 0:11 / 32:45

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

C4S 2 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

Feminization project prison pussy

38% HD 0:30 / 7:29

Feminization project prison pussy

Clips4sale 9 months ago

Road Trip Day 4

52% HD 0:39 / 31:40

Road Trip Day 4

FapHouse 6 months ago

Road Trip day 4

40% 0:11 / 31:40

Road Trip day 4

Locked Up and Horned Up Part 1

62% HD 1:09 / 32:46

Locked Up and Horned Up Part 1

TransAngels 3 years ago

Locked Up and Horned Up Part 2

51% HD 1:08 / 31:54

Locked Up and Horned Up Part 2

TransAngels 3 years ago

Steven Sweat and Danielle Foxxx

60% HD 0:39 / 44:48

Steven Sweat and Danielle Foxxx

FapHouse 1 year ago

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

53% 0:11 / 39:51

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

Aspen Brooks Is Too Pretty For Jail!

61% HD 1:48 / 58:28

Aspen Brooks Is Too Pretty For Jail!

KinkTrans 6 years ago

TS Seduction: Dorian and Jessica Host

63% HD 0:30 / 42:00

TS Seduction: Dorian and Jessica Host

AEBN 8 years ago

Steven Sweat and Danielle Foxxx

58% HD 2:08 / 44:48

Steven Sweat and Danielle Foxxx

KinkTrans 18 years ago

The Reformatory Part 2

62% 0:19 / 27:40

The Reformatory Part 2

Clips4sale 2 weeks ago

DISCIPLINARY ACTION

56% 0:30 / 32:13

DISCIPLINARY ACTION

Clips4sale 11 months ago

Trannie Visit Pt 2

66% 0:11 / 8:51

Trannie Visit Pt 2

Clips4sale 2 years ago

Trans Prison

HD 0:30 / 2:35:00

AEBN 7 years ago

Steven Sweat and Danielle Foxxx

50% 0:11 / 44:48

Steven Sweat and Danielle Foxxx

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

64% 4K 0:12 / 15:29

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

Clips4sale 1 year ago

TS Seduction: Steven Sweat and Danielle Foxxx

HD 0:30 / 44:00

TS Seduction: Steven Sweat and Danielle Foxxx

AEBN 8 years ago

Sex with the Prisoner

52% VR 1:30 / 50:45

Sex with the Prisoner

TSVirtualLovers 4 years ago

BNWO Prisoner Orientation Video

59% 4K 0:26 / 12:53

BNWO Prisoner Orientation Video

Clips4sale 1 month ago

Avery Angel BJ Exchange

54% HD 0:11 / 17:06

Avery Angel BJ Exchange

Clips4sale 2 years ago

He Had Me Cumming

HD 1:10 / 24:17

He Had Me Cumming

TransAngels 1 year ago

Disciplinary Action

58% 4K 0:30 / 32:13

Disciplinary Action

Clips4sale 6 months ago

Prison Temptation

58% 4K 0:30 / 21:45

Prison Temptation

Futanari 1 year ago

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

62% HD 0:10 / 28:38

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

LoyalFans 3 years ago

Penetration, Your Honor!

HD 1:13 / 33:00

Penetration, Your Honor!

TransAngels 3 years ago

Sissies Belong In Chastity (HD MP4)

55% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 1 year ago

Prisoner of the Matriarchy: Warrior Captured And Pegged

57% 0:11 / 15:12

Prisoner of the Matriarchy: Warrior Captured And Pegged

Clips4sale 1 year ago

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

53% 0:09 / 14:20

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

Clips4sale 10 months ago

You are a Prisoner to your Sissy Porn

HD 0:29 / 11:43

You are a Prisoner to your Sissy Porn

Clips4sale 2 months ago

Sissies in Space 01: Processing The Prisoners

61% HD 0:32 / 17:14

Sissies in Space 01: Processing The Prisoners

Clips4sale 3 years ago

Welcome to Prison, Bitch!!

66% 0:20 / 12:57

Welcome to Prison, Bitch!!

Clips4sale 7 months ago

Slut Milking (1080p)

49% HD 0:12 / 15:15

Slut Milking (1080p)

Clips4sale 9 months ago

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

50% 0:11 / 45:39

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

C4S 2 years ago

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

50% 4K 0:33 / 10:09

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

Clips4sale 1 year ago

TS Seduction: Steven Sweat and Danielle Foxxx

HD 0:30 / 44:00

TS Seduction: Steven Sweat and Danielle Foxxx

AEBN 8 years ago

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

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

Clips4sale 9 months ago

Her Prisoner - sissy chained and left alone *wmv*

56% 4K 0:25 / 10:40

Her Prisoner - sissy chained and left alone *wmv*

Clips4sale 6 months ago

TS-Giantess escapes prison and grows and takes over the world!!!

48% 0:30 / 5:35

TS-Giantess escapes prison and grows and takes over the world!!!

Clips4sale 1 month 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

Bang My Tranny Ass 3

HD 0:30 / 2:07:00

Bang My Tranny Ass 3

AEBN 16 years ago

FULL MOVIE A Prisoner in StepDaddys House

47% HD 0:30 / 1:09:16

FULL MOVIE A Prisoner in StepDaddys House

Clips4sale 3 months ago

Nyobi Khan and Rico

HD 0:39 / 59:46

Nyobi Khan and Rico

KinkTrans 17 years ago

Trans Prison

HD 0:30 / 2:35:00

AEBN 7 years ago

Serving Your Ass to Her Cock to Spring Yourself from Jail

66% HD 0:42 / 40:31

Serving Your Ass to Her Cock to Spring Yourself from Jail

KinkTrans 11 years ago

Her Prisoner Part 24 - Sissy Training VII

64% 4K 0:51 / 10:40

Her Prisoner Part 24 - Sissy Training VII

Clips4sale 1 year 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

Angels Love Angels

HD 0:30 / 2:23:00

Angels Love Angels

AEBN 6 years ago

Sissies Belong In Chastity (SD MP4)

66% 4K 0:30 / 15:17

Sissies Belong In Chastity (SD MP4)

Clips4sale 1 year ago

Trans Prison

HD 0:30 / 2:35:00

AEBN 7 years ago

beauty warrior at prison - 3d_animation

HD 0:30 / 20:21

beauty warrior at prison - 3d_animation

PornBox 5 months ago

Locked Up and Horned Up Part 3

63% HD 1:13 / 39:50

Locked Up and Horned Up Part 3

TransAngels 3 years ago

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

61% 0:39 / 31:05

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

FapHouse 2 months 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 6 months ago

classy and submissive

49% 0:30 / 25:36

classy and submissive

Clips4sale 5 months ago

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

64% 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 2 years ago

Her Prisoner Part 23 - Sissy Training VI **wmv version**

63% 4K 0:45 / 10:09

Her Prisoner Part 23 - Sissy Training VI **wmv version**

Clips4sale 1 year ago

Dorian and Jessica Host

HD 1:58 / 42:58

Dorian and Jessica Host

KinkTrans 18 years ago

Her Prisoner Part 18 - Her Sissy Slave Maid

55% 4K 0:45 / 10:23

Her Prisoner Part 18 - Her Sissy Slave Maid

Clips4sale 1 year ago

The Horny Police Officer Is Back to Punish You!

65% HD 0:39 / 14:18

The Horny Police Officer Is Back to Punish You!

FapHouse 4 months ago

She-Male Strokers 52

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

She-Male Strokers 52

AEBN 13 years ago

DETAINED AND DRAINED *HD 1080*

HD 0:30 / 16:33

DETAINED AND DRAINED *HD 1080*

Clips4sale 1 year ago

Hot As Hell : Actors Who Have Played Satan

Premium 57% HD 15:20

Hot As Hell : Actors Who Have Played Satan

Mr.Man 3 years ago

TS Mistress Stroka Fucking Part 2

55% 0:11 / 15:31

TS Mistress Stroka Fucking Part 2

Clips4sale 1 year ago

You're the little whore that could! mp4

You're the little whore that could! mp4

Clips4sale 4 years ago

America's Next Top Tranny Season 1

64% HD 0:30 / 1:44:00

America's Next Top Tranny Season 1

AEBN 16 years ago

Female Mask Maid Goes to Prison

Female Mask Maid Goes to Prison

Clips4sale 3 years ago

La Cherry Spice Long, Hard, Inside

HD 0:39 / 37:59

La Cherry Spice Long, Hard, Inside

FapHouse 1 week 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

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

PRISON TEMPTATION

65% HD 0:20 / 21:45

PRISON TEMPTATION

Clips4sale 1 year ago

Banged Behind Bars

HD 0:40 / 19:10

Banged Behind Bars

TransAngels 1 year ago

Chastity Prisoner Anal Hooked and Vibed

57% 0:23 / 48:28

Chastity Prisoner Anal Hooked and Vibed

Clips4sale 5 months ago

WRONG HOUSE *HD 1080*

61% HD 0:33 / 14:14

WRONG HOUSE *HD 1080*

Clips4sale 1 year 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 1 week ago

Man Catcher - shackled sissy maid training *MOV*

64% 4K 0:25 / 10:26

Man Catcher - shackled sissy maid training *MOV*

Clips4sale 11 months ago

HONOR AMONG QUEENS

66% HD 0:10 / 24:59

HONOR AMONG QUEENS

LoyalFans 1 day ago

D Vikky Pegging and Anal Play Part 1

66% 0:15 / 6:46

D Vikky Pegging and Anal Play Part 1

Clips4sale 1 month 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 3 months 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 5 months 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

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 3 years ago

HONOR AMONG QUEENS (WMV FORMAT)

HONOR AMONG QUEENS (WMV FORMAT)

Clips4sale 1 week ago

Man Catcher - transformation of her prisoner II *MOV*

HD 0:26 / 16:09

Man Catcher - transformation of her prisoner II *MOV*

Clips4sale 1 year ago

Feminized Cosplay Prisoner (Turned Into a Booth Babe at the Gaming Convention)

57% 0:30 / 39:53

Feminized Cosplay Prisoner (Turned Into a Booth Babe at the Gaming Convention)

Clips4sale 9 months ago

Man Catcher - his permanent collaring *MOV*

HD 0:21 / 14:07

Man Catcher - his permanent collaring *MOV*

Clips4sale 1 year 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 3 years ago

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

65% 0:13 / 9:40

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

Clips4sale 6 months ago

You Are a Prisoner to Your Sissy Porn

HD 0:39 / 11:48

You Are a Prisoner to Your Sissy Porn

FapHouse 1 month ago

Laying On The Lam

66% HD 1:07 / 40:49

Laying On The Lam

TransAngels 3 years ago

Man Catcher - the punishment collar *MOV*

HD 0:22 / 11:30

Man Catcher - the punishment collar *MOV*

Clips4sale 1 year ago

Retribution Part 9

HD 0:31 / 14:29

Retribution Part 9

Clips4sale 1 year ago

Caged Lady Meat! A Sexploitation Domination Extravaganza!

55% 0:11 / 23:40

Caged Lady Meat! A Sexploitation Domination Extravaganza!

Her Prisoner Part 21 - Sissy Training IV **MOV**

55% 4K 0:41 / 10:09

Her Prisoner Part 21 - Sissy Training IV **MOV**

Clips4sale 1 year ago

Hot Prisoner Shemale ladyboy Cute BBW Blonde Booty Crossdresser Femboy

Premium HD 16:55

Hot Prisoner Shemale ladyboy Cute BBW Blonde Booty Crossdresser Femboy

xnxxGold 2 years ago

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

65% HD 0:11 / 8:32

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

Clips4sale 2 years ago

Trans Domination

58% HD 0:10 / 12:30

Trans Domination

LoyalFans 2 months ago

imprisoned by The Sisterhood: breeding stock for feral futa

43% HD 0:10 / 15:01

imprisoned by The Sisterhood: breeding stock for feral futa

LoyalFans 7 months ago

Road Trip day 4

HD 0:38 / 31:40

Road Trip day 4

KinkTrans 16 years ago

Street Walker Is Given A Break By A Hot TS Officer

HD 0:30 / 40:00

Street Walker Is Given A Break By A Hot TS Officer

AEBN 3 years ago

TRANSEROTICA Alura Jenson Sandwiched Between Foxxy and Zeb Atlas

Premium 63% HD 32:13

TRANSEROTICA Alura Jenson Sandwiched Between Foxxy and Zeb Atlas

XVideosRed 4 years ago

twink fucked by massive cock

twink fucked by massive cock

PornBox 2 years ago

Hunted and Caged Part 12 - Prisoner to sissy Transformation 6 with Anna List

4K 0:46 / 10:19

Hunted and Caged Part 12 - Prisoner to sissy Transformation 6 with Anna List

Clips4sale 1 year ago

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

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

Clips4sale 9 months ago

Wonder Woman Busts Harley Quinn

55% HD 0:34 / 24:10

Wonder Woman Busts Harley Quinn

Clips4sale 3 years ago

ARREST GONE AWRY PT 2 *HD 720*

HD 0:32 / 16:51

ARREST GONE AWRY PT 2 *HD 720*

Clips4sale 1 year ago

PEGGING NURSES

68% HD 0:30 / 9:46

Clips4sale 3 years ago

TRANNY TREK - Prisoner of the Cardassians

TRANNY TREK - Prisoner of the Cardassians

Clips4sale 4 years ago

THE PRISONERS

63% 0:14 / 11:35

Clips4sale 1 year ago

Princess Donna's Snatched & Kept New Sextoy Stefani Special

Premium 1:03:15

Princess Donna's Snatched & Kept New Sextoy Stefani Special

Released From Masculine Jail

45% 0:11 / 7:59

Released From Masculine Jail

Clips4sale 2 years 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

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406 results found

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