‘jail’ stories

Active tags
Active tags
jail 

Category

Diversion Pt. 03

Weekend getaway, interrupted and behind bars.

4.88
3.5k
1
0
1

The Naughty Nymph Ch. 06

Cassidy goes to jail, but only for a visit.

H
4.82
1.9k
5
5
6

Behind Bars

An impatient prisoner makes a deal with the prison guard.

4.8
1.4k
1
0
4

Women's Bondage Prison Pt. 18

Jill learns about her new home and training.

H
4.77
4.7k
1
1
7

Fresh Meat At The Prison Pt. 05

Jail break! The guys get out of prison and fuck.

H
4.73
4.4k
12
4
19

The Story of Valentine

Love & Faith are woven between a Priest and a convert.

H
4.71
30.1k
7
15
18
0

Fresh Meat At The Prison Pt. 04

Gavin and Rory put on a show for the prison warden.

H
4.71
6.9k
13
3
20

Elf Patty

He falls for his son's ex-girlfriend.

H
4.71
28.4k
36
34
91
0

Bottom Bunk Bitch Ch. 03

Brenda sinks further into feminization as a prison whore.

H
4.71
32.2k
38
5
45

Ex-Con Uncle was My First Pt. 02

Ex-Con Uncle and nephew get acquainted.

H
4.7
32.4k
85
13
116

Bottom Bunk Bitch Ch. 04

Brenda performs tricks for her master in the prison yard.

H
4.68
21.5k
31
10
36

Milking An Ex-Con

Twink takes advantage of sex-deprived parolee.

H
4.68
34.3k
48
6
87
0

Seduction at the Old Gaol Ch. 02

Belinda and James explore the gaol's torture devices.

H
4.66
29.8k
9
1
16

Shortening His Sentence

All he has to do is date the worst shemale inmate.

H
4.65
185.1k
249
20
313

Homecoming

After a long time away, childhood sweetheart returns.

HW
4.64
81.6k
70
13
82

Women's Bondage Reformatory School Pt. 03

Claire adjusts to her new home and compares it to prison.

H
4.64
16.1k
6
1
13

Seduction at the Old Gaol

Flirting, Seduction, Imprisonment on a visit to the Old Gaol.

H
4.63
35.5k
42
2
73

Women's Bondage Prison Pt. 17

Lucy wears her transport chains and has a new visitor.

H
4.63
6.1k
0
2
4

Women's Bondage Prison Pt. 11

Lucy learn more about her prison and serving hard time.

H
4.63
15.3k
8
1
12

Seduction at the Old Gaol Ch. 03

Belinda turns James into part of the gaol's exhibit.

H
4.62
17.6k
3
1
6

Fallout 02: Prime Suspect

A long-term affair has dire consequences.

H
4.62
191.7k
273
245
388

Soft Baby

Drunk-driving yuppie lives a new life in jail.

H
4.62
174.5k
90
20
111
0

Becoming His Prison Bitch Pt. 03

Lexi must choose between his freedom and Darian.

H
4.61
26.6k
34
5
45

Women's Bondage Prison Pt. 16

Lucy gets help from another inmate while being punished.

H
4.61
4.7k
3
0
5

Imprisoned by My Fantasy Ch. 05

I'm finally released from jail, but a new experience awaits.

H
4.61
38.5k
30
10
38

UCLA to Big D Ch. 11

Corrupt cop cuts deal to ensnare buddie's big-titted wife.

H
4.6
75.1k
34
7
57

The Storyteller

A writer finds himself in gaol in rather rough company.

H
4.6
11.5k
3
4
3
0

Bottom Bunk Bitch Ch. 02

Brendan continues his feminization as Brenda in prison.

H
4.6
34.2k
49
5
63

Prison Pet Pt. 03

Avette teaches Erica the wonders of anal sex.

H
4.6
67.5k
44
1
53

A Halloween Prisoner Pt. 02

Allison reveals what's in store for Prisoner Jennifer.

H
4.59
22.7k
14
5
22

Unusual, Butt Not Quite Cruel

An evil career criminal gets an unorthodox interrogation...

H
4.59
173.4k
67
13
81
0

Fresh Meat At The Prison Pt. 06

Teasing the parol officer.

H
4.59
4.2k
12
6
22

The Queen Inmate's Pet Ch. 01

A human guard starts working at an all-female alien prison.

H
4.59
78.3k
187
28
245
0

Women's Bondage Prison Pt. 15

Lucy and her fellow prisoners work hard in their cells.

H
4.59
9.8k
2
1
6

Uncle Joe's Adventure in Prison

Uncle Joe gets sent to prison and finds relief.

H
4.59
24.8k
28
4
59
0

Jessica's Change Management Ch. 24

Jessica is arrested and taken to the police station.

H
4.58
22.9k
6
4
16

Seduction at the Old Gaol Ch. 09

Belinda teases, fucks and leaves him locked in a box.

H
4.58
15.4k
3
0
9

Undercovers Pt. 02

Rookie Officer gets to work.

H
4.58
28.2k
21
7
25

Kelly Does Cabo

Sex, love and debauchery in Cabo san Lucas.

H
4.58
9.4k
7
1
17
0

Women's Bondage Prison Pt. 06

Lucy finds herself in another punishment cell.

H
4.57
20.9k
11
1
16

Imprisoned by My Fantasy Ch. 04

As the night ends, I have to choose; cumming or leaving?

H
4.57
42.1k
34
8
41

Jean - The Birth of Venus Ch. 11

The Electrified Gold Clit Band.

H
4.56
19.6k
7
0
13

Neighborly Gesture Ch. 02

Ben and Keisha get closer during a night of passion.

H
4.56
15.6k
4
0
7

Happy Endings

Desiree learns the tricks of the trade.

H
4.56
67.6k
17
4
21

The Inheritance

Cheating, Betrayal, Jail, Treasure and True Love.

H
4.56
136.9k
163
75
218
0

Locked Up Autumn Ch. 02

Morning sex for young woman before reporting to prison.

H
4.55
5.2k
0
1
1

Seduction at the Old Gaol Ch. 04

The lovers are locked in the cell for the night.

H
4.55
17.6k
1
1
4

Women's Bondage Prison Pt. 08

Lucy spends time in a training cell.

H
4.54
19.8k
4
2
10

Seduction at the Old Gaol Ch. 08

Incarceration and sex: life as a prisoner in Belinda's gaol.

H
4.54
14.9k
4
1
7

How High A Price - Anon

Susan's Choice - Sequel to Troubador's How High A Price

H
4.54
170.3k
202
232
306
0

Seduction at the Old Gaol Ch. 05

Belinda uses rivets to permanently lock his shackles.

H
4.54
20.4k
2
0
4

The Jail Bunny Ch. 02

Kelli's roleplay with her boyfriend continues.

H
4.54
3.5k
6
2
9

Prison Sissy Cuckboy Ch. 01

Beta bitch joins a gang as a sissy cuckboy.

H
4.54
32.7k
60
7
106
0

The Jail Bunny Ch. 04

Kellie finally gets fucked in her cell.

NEWH
4.54
2k
2
2
4

Women's Bondage Prison Pt. 10

Lucy had a pre-trial inspection.

H
4.53
14.3k
6
2
9

Prison Pet Pt. 06

Erica's story of submission comes to its conclusion.

H
4.53
55.5k
37
6
46

My Son, The New Man of the House

Husband goes to jail; sex-razed mother turns to her son.

H
4.53
863.7k
811
36
1.1k
0

Mom Gets Strip Searched Pt. 02

He watches cops abuse mom.

H
4.53
535.9k
305
0
369

Prison Time Ch. 02

KT makes a bad decision.

H
4.53
35k
21
11
23

Seduction at the Old Gaol Ch. 07

Infatuated with Belinda, James moves into his jail cell.

H
4.53
13.6k
1
1
3

Folsom Prison Blues

Jimmy's time is almost served and Katie is ready and waiting.

H
4.53
35.6k
7
7
9
0

Seduction at the Old Gaol Ch. 10

She unlocks James from the box, takes him to meet her family.

H
4.52
15.8k
4
0
8

Prison Time

Protecting Hayden turned into more than KT wanted.

H
4.52
83.8k
62
7
74

Prison Bitch

A pretty Boy gets sent to prison and becomes a bitch.

H
4.52
46.7k
47
0
97
0

Seduction at the Old Gaol Ch. 06

James is naked, handcuffed and taken advantage of by Kate.

H
4.52
22.5k
7
0
10

Women's Bondage Prison Pt. 12

Lucy goes on a prison inspection tour.

H
4.51
8.8k
3
0
13

Women's Bondage Prison Pt. 09

Lucy continues in her training cell.

H
4.51
19.4k
4
2
8

Women's Bondage Reformatory School Pt. 04

Claire serves time in detention.

H
4.51
15.9k
3
2
12

Detention Center FNG

Jillian finds love at the jail.

H
4.51
17.8k
18
5
27
0

Unauthorized Entry

Angie gets to live out her fantasy of getting arrested.

H
4.51
12.3k
7
2
16
0

Imprisoned by My Fantasy Ch. 03

After being arrested, I'm taken to jail in my hooker-wear.

H
4.5
53.6k
44
10
53

Women's Bondage Prison Pt. 01

Lucy learns who in this bondage prison will violate her.

H
4.5
17.9k
9
1
20

Women's Bondage Prison Pt. 02

Lucy progresses in her prison training

H
4.5
15.6k
6
0
14

Imprisoned by My Fantasy Ch. 02

We go forward with her plan to have me arrested as a hooker.

4.49
51.1k
46
11
51

Ex-Con Uncle was My First Pt. 01

Ex-Con Uncle and nephew get acquainted.

4.49
45.5k
81
6
133

The King's Harem Pt. 04

The King breeds Abrielle then deals with an intruder.

4.49
58.7k
41
4
70

Women's Bondage Prison Pt. 13

Lucy prepares and begins for prison exercise.

4.48
7.5k
1
0
6

Tooth and Claw

A prisoner gets her comeuppance from a domme...

4.47
19.7k
8
0
18
0

The New Republic

The Republic has a very different type of justice system.

4.47
14.4k
3
0
18
0

Women's Bondage Prison Pt. 07

Lucy works in the prison mill.

4.47
16.9k
6
1
9

Imprisoned by My Fantasy Ch. 01

A feminized cuckold's wife wants to fulfill his fantasy.

4.46
87.5k
87
6
134

Women's Bondage Prison Pt. 00

Lucy is arrested, transported, and booked into the prison.

4.46
39.9k
19
5
35

A Halloween Prisoner Pt. 06

While Jen goes through hell, we meet her male counterpart!

4.46
8.2k
4
3
7

Caught in a Spider's Web

Pretty girl's night in jail is a memorable one.

4.45
178.2k
63
10
91
0

Roxie & Erica: Blair's Victory Pt. 01

An alternate version of Prison Pet where Blair wins.

4.45
45.9k
23
3
35

Timmy's Prison Cavity Search Ch. 04

Timmy takes the HGH mutated prison daddy monster cock.

4.45
103.6k
57
4
80

Prison Pet Pt. 01

Erica draws Roxie's attention at all all-girl prison.

4.45
117.6k
145
5
209

Cobra Crew: Freeing Escobar Ch. 04

A new victim falls into the hands of the Cobra Crew.

4.45
41.3k
7
1
14

The Exhibitionist Pt. 03

The continuing story of a MILF exhibitionist.

4.44
48.7k
14
0
18

Locked Up Autumn

Young woman online the day before she reports to prison.

4.44
4.9k
2
3
10

Confrontation Ch. 05: Jaguar Nabbed

What happened to Elena's cousins? Is Jaguar surprised?

4.44
735
00
2
Active tags
Active tags
jail
Separate tags with commas. More info in the FAQ