‘jail’ stories

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jail 

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The Jail Bunny Ch. 04

Kellie finally gets fucked in her cell.

NEWH
4.54
1.8k
2
1
4

The Jail Bunny Ch. 03

Kellie gives a blowjob in her jail cell.

NEW
4.36
5.3k
9
5
14

Behind Bars (Gay)

An impatient prisoner makes a deal with the prison guard.

3.8
1.3k
1
0
2

Behind Bars

An impatient prisoner makes a deal with the prison guard.

4.8
1.4k
1
0
4

The Jail Bunny Ch. 02

Kelli's roleplay with her boyfriend continues.

H
4.54
3.5k
6
2
9

The Jail Bunny Ch. 01

Kellie gets to live her fantasy of going to jail.

4.41
4k
7
3
18

Fresh Meat At The Prison Pt. 06

Teasing the parol officer.

H
4.59
4.1k
12
6
22

The Naughty Nymph Ch. 06

Cassidy goes to jail, but only for a visit.

H
4.82
1.8k
5
5
6

Women's Bondage Prison Pt. 18

Jill learns about her new home and training.

H
4.77
4.7k
1
1
7

Bottom Bunk Bitch Ch. 05

Brenda is pimped out the sadistic prison guards.

4.43
9.1k
10
4
17

Women's Bondage Prison Pt. 17

Lucy wears her transport chains and has a new visitor.

H
4.63
6.1k
0
2
4

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

Prison Wife

Kaya takes a fresh approach to corrections.

4.04
9.7k
7
4
11
0

Elf Patty

He falls for his son's ex-girlfriend.

H
4.71
28.3k
36
34
91
0

Time Well Served

Three tales about incarceration.

3.95
14.5k
12
2
28
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

Women's Bondage Prison Pt. 16

Lucy gets help from another inmate while being punished.

H
4.61
4.7k
3
0
5

Confrontation Ch. 05: Jaguar Nabbed

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

4.44
734
00
2

Diversion Pt. 04

A weekend getaway, interrupted - crime and punishment.

4
1.9k
1
0
1

Diversion Pt. 03

Weekend getaway, interrupted and behind bars.

4.88
3.5k
1
0
1

Fatigue

Emotionally wrung-out.

3.56
27k
32
103
77
0

Swindled in Prison

I expected something different in prison.

4.36
14.3k
22
2
42
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

Women's Bondage Prison Pt. 14

Lucy earns time in another punishment cell.

4.42
11.1k
2
1
5

Women's Bondage Prison Pt. 13

Lucy prepares and begins for prison exercise.

4.48
7.5k
1
0
6

Careful What You Promise

I promised my future wife if her ex ever got out of jail...

2.25
34.8k
57
15
118
0

Prison Sissy Cuckboy Ch. 01

Beta bitch joins a gang as a sissy cuckboy.

H
4.54
32.7k
60
7
106
0

Attorney Client Privileges

Male attorney has steamy relationship with his new client.

4.23
6.3k
2
1
5
0

Bottom Bunk Bitch Ch. 04

Brenda performs tricks for her master in the prison yard.

H
4.68
21.5k
31
10
36

Women's Bondage Prison Pt. 12

Lucy goes on a prison inspection tour.

H
4.51
8.8k
3
0
13

Bottom Bunk Bitch Ch. 03

Brenda sinks further into feminization as a prison whore.

H
4.71
32.2k
38
5
45

Women's Bondage Prison Pt. 02.5

Lucy learns to be a better prisoner.

4.41
8.1k
3
1
7

Bottom Bunk Bitch Ch. 02

Brendan continues his feminization as Brenda in prison.

H
4.6
34.2k
49
5
63

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. 02

Lucy progresses in her prison training

H
4.5
15.6k
6
0
14

College Students Humiliated in Jail

Eric, Wes and Kyle are strip searched and deloused in jail.

3.89
15.6k
8
0
17

Day of Injustice

Ellen travels seeking her friend but wakes up in handcuffs.

4.12
13.3k
12
4
36
0

Interrupted.... and Resumed

Two SSBBWs make the best of a bad situation.

4.22
7.3k
9
1
13
0

Women's Bondage Prison Pt. 01

Lucy learns who in this bondage prison will violate her.

H
4.5
17.9k
9
1
20

Pegging Her Alpha Inmate

A female prison officer dominates a defiant hunky inmate.

4.33
25.1k
37
3
65
0

Locked Up Autumn Ch. 03

Young woman reports to prison and strip searched thoroughly.

4.4
15.6k
9
2
15

Women's Territorial Bondage Prison

A new prison for female jailbirds keeps inmates from escape.

4.44
15.6k
8
2
17
0

Kelly Does Cabo

Sex, love and debauchery in Cabo san Lucas.

H
4.58
9.4k
7
1
17
0

Locked Up Autumn Ch. 02

Morning sex for young woman before reporting to prison.

H
4.55
5.2k
0
1
1

Locked Up Autumn

Young woman online the day before she reports to prison.

4.44
4.9k
2
3
10

Dyker's Island Ch. 01-08

A look at life inside the worst women's prison in the US.

4.2
23.4k
27
10
66

Women's Bondage Prison Pt. 11

Lucy learn more about her prison and serving hard time.

H
4.63
15.3k
8
1
12

Women's Bondage Reformatory School Pt. 04

Claire serves time in detention.

H
4.51
15.9k
3
2
12

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. 10

Lucy had a pre-trial inspection.

H
4.53
14.3k
6
2
9

That Damn Tattoo

Submissive husband doesn't make it home.

4.2
7.9k
12
1
17
0

Women's Bondage Reformatory School Pt. 03

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

H
4.64
16k
6
1
13

A Halloween Prisoner Pt. 06

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

4.46
8.2k
4
3
7

Women's Bondage Reformatory School Pt. 01

A reformatory school where bondage is the main lesson.

4.39
36.2k
23
9
52

Women's Bondage Prison Pt. 09

Lucy continues in her training cell.

H
4.51
19.4k
4
2
8

One Week Left

Carrie has a romantic encounter with her cellmate.

3.81
8.2k
6
3
12
0

Women's Bondage Prison Pt. 08

Lucy spends time in a training cell.

H
4.54
19.8k
4
2
10

Women's Bondage Prison Pt. 07

Lucy works in the prison mill.

4.47
16.9k
6
1
9

Prison Bitch

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

H
4.52
46.7k
47
0
97
0

Women's Bondage Prison Pt. 00

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

4.46
39.9k
19
5
35

Women's Bondage Prison Pt. 06

Lucy finds herself in another punishment cell.

H
4.57
20.9k
11
1
16

Women's Bondage Prison Pt. 05

Lucy serves time in the public viewing cells.

4.36
21.8k
6
1
9

Women's Bondage Prison Pt. 04

Lucy find herself in a punishment cell.

4.41
32.5k
10
2
13

Women's Bondage Prison Pt. 03

Lucy's inspection leads her to a different chain gang.

4.4
24.4k
13
2
21

Women's Bondage Prison

A bondage theme prison tests Lucy and her fellow prisoners.

4.37
62.3k
46
3
96

Family Disrupted Pt. 01

Cuckolds beware: prisoners are coming for your hot wives!

3.83
67.2k
110
40
217

Midwest Mom Goes to Prison Pt. 01

A Mom Goes to Prison and experiences the intake process.

3.89
24.7k
13
10
23

Caribbean Reign Ch. 01-02

A sugarcane heiress is shipped off to her rival's plantation.

4.21
29.5k
20
5
84

Jail Bear

Two prisoners enjoy gay sex before lights out.

4.29
9.8k
5
1
8
0

Uncle Joe's Adventure in Prison

Uncle Joe gets sent to prison and finds relief.

H
4.59
24.8k
28
4
59
0

Bright Sky Beach Ch. 01

Heather and her friends spend a night in jail.

4.1
15.5k
13
3
31

Milking An Ex-Con

Twink takes advantage of sex-deprived parolee.

H
4.69
34.3k
48
6
87
0

Ex-Con Uncle was My First Pt. 02

Ex-Con Uncle and nephew get acquainted.

H
4.7
32.4k
85
13
116

Ex-Con Uncle was My First Pt. 01

Ex-Con Uncle and nephew get acquainted.

4.49
45.5k
81
6
133

Hormone Hannah

Pregnant Hannah would do anything for her husband.

4.19
33.9k
51
30
89
0

Unauthorized Entry

Angie gets to live out her fantasy of getting arrested.

H
4.51
12.3k
7
2
16
0

The Reunion Trap Ch. 01

Man recalls high school incident after 5-year reunion invite.

4.41
12.8k
24
6
43

Fallout 02: Prime Suspect

A long-term affair has dire consequences.

H
4.62
191.7k
273
245
388

A Halloween Prisoner Pt. 02

Allison reveals what's in store for Prisoner Jennifer.

H
4.59
22.7k
14
5
22

A Halloween Prisoner

Jennifer let her friend choose Halloween costumes. Big oops.

4.37
47.8k
58
9
107

Simon Says Revenge Ch. 02-04

The past comes back hard.

3.91
20.9k
8
15
20

Becoming a Repeat Offender

A "Mostly Straight" Married Man Goes to Jail.

0
17.2k
15
2
28
0

Simon Says Revenge Ch. 01

My version of an ending of Danielle's Revenge.

4.19
20.1k
15
9
34

Detention Center FNG

Jillian finds love at the jail.

H
4.51
17.8k
18
5
27
0

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

Jessica's Change Management Ch. 24

Jessica is arrested and taken to the police station.

H
4.58
22.9k
6
4
16

Raven's Valley Prison Ch. 03 - Final

Darius is taken to see "The Doctor" in this final chapter.

4.14
7.7k
6
0
9

Fiancée Gets Strip Searched

Virgin fiancée gets strip searched in a small town jail.

4.34
123.7k
84
18
161
0

Raven's Valley Prison Ch. 02

Connor has agreed to protect Darius, but the cost is high.

4.29
9.1k
6
0
9

Dicking Under the Influence

After too many wrong turns, she takes the wheel.

4.21
24.2k
31
3
49
0

Letter from a Jailed Husband

A wife gets a shocking letter from her incarcerated husband.

4.11
37.6k
47
7
65
0

Raven's Valley Prison

Darius is thrown into a medieval prison.

3.94
18.8k
11
2
21

Guilty, an Alternate Version

An alternate version of stev2244's original.

3.7
36.9k
48
41
64
0
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