‘jail’ stories

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jail 

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My Son, The New Man of the House

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

H
4.53
866.7k
814
36
1.1k
0

Jail Bird Dad

Dad has his way with daughter.

4.37
524.8k
532
48
647
0

Mom Gets Strip Searched Pt. 02

He watches cops abuse mom.

H
4.53
537.3k
305
0
369

Fallout 02: Prime Suspect

A long-term affair has dire consequences.

H
4.62
194.8k
276
247
392

Shortening His Sentence

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

H
4.65
185.6k
248
20
317

How High A Price - Anon

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

H
4.53
171.1k
203
233
309
0

Anger Management

I'm not really that bad, "Am I"

4.43
253.7k
202
147
275
0

The Queen Inmate's Pet Ch. 01

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

H
4.59
78.6k
190
28
248
0

A Bad Day At The Jail

Convict has fun with his new cellmate.

4.26
287.6k
170
11
195

The Inheritance

Cheating, Betrayal, Jail, Treasure and True Love.

H
4.56
137.4k
165
75
223
0

Shortening His Sentence Ch. 02

More shemale inmates enter the mix.

H
4.67
131.9k
148
33
171

Prison Pet Pt. 01

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

4.45
118.1k
145
5
210

A Bad Day At The Jail: Lesbian Version

Convict has fun with Her new cellmate.

4.13
332.4k
115
16
133

Family Disrupted Pt. 01

Cuckolds beware: prisoners are coming for your hot wives!

3.83
67.9k
111
40
220

Becoming His Prison Bitch

Lexus learns his place behind bars.

4.45
82.5k
110
10
159

Soft Baby

Drunk-driving yuppie lives a new life in jail.

H
4.63
174.8k
90
20
112
0

Imprisoned by My Fantasy Ch. 01

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

4.46
87.8k
88
6
136

Money, Sex, Wife & Daughter Ch. 01

Mike steals money and gives his wife and daughter as payback.

4.03
132.6k
88
5
139

Leanna

Stuck-up schoolgirl spends a night in jail.

4.15
133.8k
86
5
131

Ex-Con Uncle was My First Pt. 02

Ex-Con Uncle and nephew get acquainted.

H
4.7
32.8k
85
13
116

Fiancée Gets Strip Searched

Virgin fiancée gets strip searched in a small town jail.

4.34
124.8k
84
18
163
0

Wrongful Revenge Ch. 02 - FTDS

A wrongful revenge retaliation.

4.1
179.3k
82
129
137
0

Ex-Con Uncle was My First Pt. 01

Ex-Con Uncle and nephew get acquainted.

4.49
46.1k
82
6
135

Marriage On The Rocks

Wife's drinking paves the way for disaster.

3.96
233.5k
75
144
118
0

Conjugal Visit

Son has a conjugal visit, but doesn't know who with.

4.17
167k
73
13
94
0

Homecoming

After a long time away, childhood sweetheart returns.

HW
4.64
81.8k
70
13
82

It's All My Fault Ch. 02

After all thats happened she want to get her husband back.

4.08
200k
70
99
107
0

Jail Time Ch. 01

Caught and dominated by powerful black guys.

4.2
238.9k
69
11
97

Unusual, Butt Not Quite Cruel

An evil career criminal gets an unorthodox interrogation...

H
4.59
173.5k
68
13
84
0

Payback - Ten Fold and Then Some

Even a wimp has his limits.

4.28
201.5k
66
117
120
0

I'm not an Evil Man

What was her intent?

4.18
145.6k
66
65
87
0

Feeding Them to the Lions Ch. 01

Stranded coeds are picked up by busload of prisoners.

4.28
197.7k
65
9
105

Caught in a Spider's Web

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

4.45
178.5k
63
10
91
0

Prison Time

Protecting Hayden turned into more than KT wanted.

H
4.52
83.9k
62
7
74

21st Century Slave Ch. 01

Wife is jailed and punished in a far away place.

3.64
218k
62
6
84

A Ticket to Lust Ch. 02

Vicki bargains her way out of jail.

4.42
784.1k
62
0
70

Cock Sucking Jail Whore

He goes to jail to get gang banged.

4.12
235.4k
61
16
82
0

Prison Sissy Cuckboy Ch. 01

Beta bitch joins a gang as a sissy cuckboy.

H
4.53
34k
61
7
108
0

Run For Your Life

Man gets between a woman and her boyfriend, and suffers.

4.34
204.7k
59
113
80
0

A Halloween Prisoner

Jennifer let her friend choose Halloween costumes. Big oops.

4.39
48.1k
58
9
107

Careful What You Promise

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

2.26
35.8k
58
15
123
0

Timmy's Prison Cavity Search Ch. 04

Timmy takes the HGH mutated prison daddy monster cock.

4.45
103.9k
57
4
81

Addicted Ch. 02 - FTDS

Costly Addiction - my ending to CuckStudent's Addicted

4.33
125.6k
54
92
97
0

Those Who Cuckold Get Paid Back

Her horny admirers have plans for pretty wife.

4.06
139.8k
54
43
78

Sexy Cop Traffic Stop

Sexy brunette takes it up the ass to avoid a ticket and jail.

4.22
111.4k
52
6
69
0

The Toybox Ch. 01

Teen twink Noah is forced to suck his first dick in prison.

3.8
93k
51
1
70

Hormone Hannah

Pregnant Hannah would do anything for her husband.

4.2
34.1k
51
30
90
0

One Question Too Many

Investigative journalist Terri London wants an "inside look".

4.16
177k
50
19
72
0

Letter from a Jailed Husband

A wife gets a shocking letter from her incarcerated husband.

4.12
37.9k
49
7
67
0

Bottom Bunk Bitch Ch. 02

Brendan continues his feminization as Brenda in prison.

H
4.6
35.2k
49
5
63

Milking An Ex-Con

Twink takes advantage of sex-deprived parolee.

H
4.69
34.7k
49
6
88
0

Guilty, an Alternate Version

An alternate version of stev2244's original.

3.71
37.1k
48
41
64
0

TV News Babe in Jail

TV journalist goes to jail to earn ratings points.

3.14
252.5k
47
0
71
0

Timmy's Prison Cavity Search Ch. 02

Timmy is reunited with an old buddy from the streets.

4.27
66.3k
47
4
57

Hard Time in Prison Pt. 01

White boy Brad goes to prison.

4.19
64.2k
47
8
66
0

Imprisoned by My Fantasy Ch. 02

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

H
4.5
51.3k
47
11
52

Women's Bondage Prison

A bondage theme prison tests Lucy and her fellow prisoners.

4.37
63.3k
47
3
99

Serie Noire 01

The power outage that blacked out my life.

4.18
143.3k
47
75
70

Prison Bitch

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

H
4.52
47.6k
46
0
97
0

Jailed Cuckold & Bullied BETA Son

Jailed dad cuckolded by MILF stepmom & buddy's younger bro.

2.89
50.6k
46
18
84
0

Caught Masturbating in Prison

Guard catches her and discovers her love for cocksucking.

4.2
83.7k
46
4
60
0

Prison Pet Pt. 03

Avette teaches Erica the wonders of anal sex.

H
4.6
67.7k
44
1
53

Brought to Her Knees for Guard

Strip search leads to her sucking the guard off.

3.74
154.4k
44
7
62
0

Seduction at the Old Gaol

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

H
4.64
35.8k
44
2
76

Imprisoned by My Fantasy Ch. 03

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

H
4.5
53.7k
44
10
53

Uncle Finds a Worthy Task Pt. 01

BDSM, Incest, Golden Shower.

4.31
48.2k
42
9
51

Scarlett's DUI

Scarlett Johansson is arrested for drunk driving.

3.89
84.8k
42
1
52
0

The King's Harem Pt. 04

The King breeds Abrielle then deals with an intruder.

4.49
59.7k
41
4
71

Big Molly

He bribed the judge to send him to the women's penitentiary.

4.23
66.2k
41
4
53
0

Janie Goes to Jail

Janie accepts a dare that leads to trouble.

4.41
55.5k
40
1
60
0

Bottom Bunk Bitch Ch. 03

Brenda sinks further into feminization as a prison whore.

H
4.71
33.1k
39
5
47

Pegging Her Alpha Inmate

A female prison officer dominates a defiant hunky inmate.

4.33
25.5k
38
3
67
0

Prison Life Ch. 01

Steven goes from frat boy to Prison Bitch.

4.1
94.7k
38
12
67
0

Prison Pet Pt. 06

Erica's story of submission comes to its conclusion.

H
4.52
55.7k
37
6
46

Is That How You Saw It Matt?

There was a few things Matt left out of the story.

3.92
133.6k
36
58
56
0

Jail Time Ch. 02

A meeting on the street.

4.21
88.7k
36
7
42

Amy vs. The Strippers

Through a misunderstanding, Amy is locked in with strippers.

4.39
34.1k
36
9
62
0

Elf Patty

He falls for his son's ex-girlfriend.

H
4.72
29.2k
35
34
88
0

Imprisoned by My Fantasy Ch. 04

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

H
4.57
42.2k
34
8
41

Prison Pet Pt. 04

Erica faces her most difficult test yet: A night with Blair.

4.18
56.3k
34
7
42

UCLA to Big D Ch. 11

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

H
4.6
75.5k
34
7
57

Becoming His Prison Bitch Pt. 03

Lexi must choose between his freedom and Darian.

H
4.61
26.7k
34
5
45

Prison Pet Pt. 05

Erica's next teacher Toni has a shocking secret.

4.37
51.8k
32
9
38

Lord Oakes' Daughter Ch. 01

Cast out publicly whipped sold into servitude and ravished.

4.42
95.1k
32
0
69

Fatigue

Emotionally wrung-out.

3.56
27.6k
32
104
79
0

Hard Time

A jailhouse conversion of a different sort.

4.17
141k
32
7
46
0

Dicking Under the Influence

After too many wrong turns, she takes the wheel.

4.21
24.3k
31
3
49
0

Sarah's Prisoner

Stealing panties, masturbation, getting caught & doing time!

3.44
65.1k
31
10
45
0

Bottom Bunk Bitch Ch. 04

Brenda performs tricks for her master in the prison yard.

H
4.69
22.3k
31
10
36

Imprisoned by My Fantasy Ch. 05

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

H
4.61
38.7k
30
10
38

Spanked in Jail

Lauren's spanking while serving a jail sentence.

4.17
153.3k
29
9
40
0

Uncle Joe's Adventure in Prison

Uncle Joe gets sent to prison and finds relief.

H
4.59
25k
28
4
60
0

Dyker's Island Ch. 01-08

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

4.2
24k
28
10
70

JailBait

His first experience after prom night.

3.98
197.2k
27
8
41
0

Sex or Jail

A MILF has a choice during a hurricane.

3.83
40.4k
25
2
34
0

Nic(k)ed

A woman gets taken by her butch cellmate.

4.16
83k
25
5
31
0

The Reunion Trap Ch. 01

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

4.41
12.9k
24
6
45
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