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Women's Studies Ch. 15

The final chapter.

by Son_of_Battles in Transgender & Crossdressers 09/12/2019
HW
4.89
90k
155
126
182

Diversion Pt. 03

Weekend getaway, interrupted and behind bars.

by craraniz in BDSM 09/18/2023
4.88
3.6k
1
0
1

Behind Bars

An impatient prisoner makes a deal with the prison guard.

by QuotedBody7 in Sci-Fi & Fantasy 03/07/2024
4.83
2k
1
0
8

The Naughty Nymph Ch. 06

Cassidy goes to jail, but only for a visit.

by farbeyondourstars in Sci-Fi & Fantasy 02/20/2024
H
4.79
2.1k
5
6
6

The Jail Bunny Ch. 04

Kellie finally gets fucked in her cell.

by HandcuffedAngie in Erotic Couplings 03/26/2024
H
4.79
3.4k
2
2
5

Fresh Meat At The Prison Pt. 05

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

by SummerSammy in Gay Male 01/04/2024
H
4.78
4.8k
12
4
19

Women's Bondage Prison Pt. 18

Jill learns about her new home and training.

by palm09 in BDSM 02/11/2024
H
4.77
5.5k
1
1
7

Elf Patty

He falls for his son's ex-girlfriend.

by JimBob44 in Mature 12/04/2023
H
4.72
29.4k
34
34
89
0

The Story of Valentine

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

by RedHairedandFriendly in Romance 01/22/2007
H
4.71
30.2k
7
15
19
0

Bottom Bunk Bitch Ch. 03

Brenda sinks further into feminization as a prison whore.

by Elixurgurl in Transgender & Crossdressers 02/15/2023
H
4.71
33.2k
39
5
47

Ex-Con Uncle was My First Pt. 02

Ex-Con Uncle and nephew get acquainted.

by kwameselinsky in Incest/Taboo 08/13/2021
H
4.7
32.8k
85
13
116

Milking An Ex-Con

Twink takes advantage of sex-deprived parolee.

by kwameselinsky in Gay Male 08/16/2021
H
4.69
34.8k
49
6
88
0

The Long Road Back Ch. 13

The Trial.

by sexygirl76 in Non-Erotic 06/02/2008
H
4.69
11.4k
00
1

Bottom Bunk Bitch Ch. 04

Brenda performs tricks for her master in the prison yard.

by Elixurgurl in Transgender & Crossdressers 03/08/2023
H
4.69
22.3k
31
10
36

Fresh Meat At The Prison Pt. 04

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

by SummerSammy in Gay Male 11/25/2023
H
4.68
7.4k
14
3
21

Shortening His Sentence Ch. 02

More shemale inmates enter the mix.

by SugarandSalt in Transgender & Crossdressers 07/29/2012
H
4.67
132k
148
33
171

Seduction at the Old Gaol Ch. 02

Belinda and James explore the gaol's torture devices.

by AndreaJordan in BDSM 01/27/2017
H
4.66
30k
9
1
16

Shortening His Sentence

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

by SugarandSalt in Transgender & Crossdressers 06/15/2012
H
4.65
185.7k
248
20
317

Homecoming

After a long time away, childhood sweetheart returns.

by Darlantan in Romance 10/07/2006
HW
4.64
81.8k
70
13
82

Seduction at the Old Gaol

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

by AndreaJordan in BDSM 09/28/2016
H
4.64
35.8k
44
2
76

Women's Bondage Reformatory School Pt. 03

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

by palm09 in BDSM 03/29/2022
H
4.64
16.4k
6
1
13

Soft Baby

Drunk-driving yuppie lives a new life in jail.

by Littlemissblair in Lesbian Sex 04/10/2001
H
4.63
174.8k
90
20
112
0

Seduction at the Old Gaol Ch. 03

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

by AndreaJordan in BDSM 02/03/2017
H
4.63
17.8k
3
1
6

Women's Bondage Prison Pt. 11

Lucy learn more about her prison and serving hard time.

by palm09 in BDSM 08/06/2022
H
4.63
15.5k
8
1
12

Women's Bondage Prison Pt. 17

Lucy wears her transport chains and has a new visitor.

by palm09 in BDSM 01/23/2024
H
4.63
6.6k
0
2
4

Fallout 02: Prime Suspect

A long-term affair has dire consequences.

by saddletramp1956 in Loving Wives 01/27/2021
H
4.62
195.1k
277
248
393

Imprisoned by My Fantasy Ch. 05

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

by Jemina004 in Transgender & Crossdressers 03/04/2020
H
4.61
38.7k
30
10
38

Becoming His Prison Bitch Pt. 03

Lexi must choose between his freedom and Darian.

by LittleKay in Gay Male 11/21/2018
H
4.61
26.7k
34
5
45

Women's Bondage Prison Pt. 16

Lucy gets help from another inmate while being punished.

by palm09 in BDSM 11/24/2023
H
4.61
5k
3
0
5

Bottom Bunk Bitch Ch. 02

Brendan continues his feminization as Brenda in prison.

by Elixurgurl in Transgender & Crossdressers 01/23/2023
H
4.6
35.2k
49
5
63

Prison Pet Pt. 03

Avette teaches Erica the wonders of anal sex.

by GayTripper in NonConsent/Reluctance 08/29/2014
H
4.6
67.7k
44
1
53

The Storyteller

A writer finds himself in gaol in rather rough company.

by Talemaster in Sci-Fi & Fantasy 08/22/2012
H
4.6
11.6k
3
4
3
0

UCLA to Big D Ch. 11

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

by FifthEstate in NonConsent/Reluctance 06/23/2018
H
4.6
75.5k
34
7
57

Women's Bondage Prison Pt. 15

Lucy and her fellow prisoners work hard in their cells.

by palm09 in BDSM 08/14/2023
H
4.59
10k
2
1
6

A Halloween Prisoner Pt. 02

Allison reveals what's in store for Prisoner Jennifer.

by sfsdada in Fetish 06/16/2020
H
4.59
22.9k
14
5
22

The Queen Inmate's Pet Ch. 01

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

by Et2bruttus in Sci-Fi & Fantasy 01/29/2015
H
4.59
78.6k
189
28
247
0

Unusual, Butt Not Quite Cruel

An evil career criminal gets an unorthodox interrogation...

by boysetsfire in Anal 02/21/2007
H
4.59
173.5k
68
13
84
0

Uncle Joe's Adventure in Prison

Uncle Joe gets sent to prison and finds relief.

by kwameselinsky in Gay Male 09/07/2021
H
4.59
25k
28
4
60
0

Undercovers Pt. 02

Rookie Officer gets to work.

by Checkmate215 in Transgender & Crossdressers 02/12/2016
H
4.58
28.3k
21
7
25

Seduction at the Old Gaol Ch. 09

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

by AndreaJordan in BDSM 08/07/2017
H
4.58
15.5k
3
0
8

Jessica's Change Management Ch. 24

Jessica is arrested and taken to the police station.

by Cathartico in NonConsent/Reluctance 01/22/2020
H
4.58
23.1k
6
4
16

Kelly Does Cabo

Sex, love and debauchery in Cabo san Lucas.

by Shaglus_Ziegler in Erotic Couplings 09/13/2022
H
4.58
9.6k
7
1
17
0

Women's Bondage Prison Pt. 06

Lucy finds herself in another punishment cell.

by palm09 in BDSM 12/19/2021
H
4.57
21.2k
11
1
16

Imprisoned by My Fantasy Ch. 04

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

by Jemina004 in Transgender & Crossdressers 07/13/2017
H
4.57
42.2k
34
8
41

Neighborly Gesture Ch. 02

Ben and Keisha get closer during a night of passion.

by MrDlyte in Erotic Couplings 10/17/2015
H
4.56
15.7k
4
0
7

The Inheritance

Cheating, Betrayal, Jail, Treasure and True Love.

by Pultoy in Loving Wives 05/14/2012
H
4.56
137.5k
165
75
223
0

Jean - The Birth of Venus Ch. 11

The Electrified Gold Clit Band.

by loerics in NonConsent/Reluctance 07/20/2019
H
4.56
19.8k
7
0
13

Happy Endings

Desiree learns the tricks of the trade.

by desireethtttv in Transgender & Crossdressers 10/17/2012
H
4.56
67.7k
17
4
21

Seduction at the Old Gaol Ch. 04

The lovers are locked in the cell for the night.

by AndreaJordan in BDSM 02/13/2017
H
4.55
17.7k
1
1
4

Locked Up Autumn Ch. 02

Morning sex for young woman before reporting to prison.

by capecodshark314 in Fetish 08/21/2022
H
4.55
5.3k
0
1
2

Ex-Cellmate Looks Him Up

She's back for her bitch.

by SugarandSalt in Transgender & Crossdressers 10/16/2012
H
4.54
231k
294
16
365
0

Seduction at the Old Gaol Ch. 08

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

by AndreaJordan in BDSM 06/30/2017
H
4.54
15k
5
1
8

Women's Bondage Prison Pt. 08

Lucy spends time in a training cell.

by palm09 in BDSM 01/20/2022
H
4.54
20k
4
2
10

Seduction at the Old Gaol Ch. 05

Belinda uses rivets to permanently lock his shackles.

by AndreaJordan in BDSM 03/19/2017
H
4.54
20.5k
2
0
4

Folsom Prison Blues

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

by Selena_Kitt in Letters & Transcripts 12/04/2006
H
4.53
35.7k
7
7
9
0

Women's Bondage Prison Pt. 10

Lucy had a pre-trial inspection.

by palm09 in BDSM 05/16/2022
H
4.53
14.5k
6
2
9

My Son, The New Man of the House

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

by blackfen in Incest/Taboo 09/23/2010
H
4.53
867k
814
36
1.1k
0

How High A Price - Anon

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

by FinishTheDamnStory in Loving Wives 09/15/2013
H
4.53
171.1k
203
233
310
0

Seduction at the Old Gaol Ch. 07

Infatuated with Belinda, James moves into his jail cell.

by AndreaJordan in BDSM 06/26/2017
H
4.53
13.7k
1
1
3

Prison Time Ch. 02

KT makes a bad decision.

by sexyjcanplay in Gay Male 07/31/2011
H
4.53
35.1k
21
11
23

Prison Sissy Cuckboy Ch. 01

Beta bitch joins a gang as a sissy cuckboy.

by MiddleKoala in Transgender & Crossdressers 03/28/2023
H
4.53
34.1k
61
7
108
0

Mom Gets Strip Searched Pt. 02

He watches cops abuse mom.

by George VI in Incest/Taboo 12/23/2003
H
4.53
537.4k
305
0
369

Women's Bondage Reformatory School Pt. 04

Claire serves time in detention.

by palm09 in BDSM 07/13/2022
H
4.52
16.2k
3
2
13

Prison Time

Protecting Hayden turned into more than KT wanted.

by sexyjcanplay in Gay Male 07/08/2011
H
4.52
83.9k
62
7
74

Seduction at the Old Gaol Ch. 06

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

by AndreaJordan in BDSM 04/16/2017
H
4.52
22.6k
7
0
10

Roxie & Erica: Blair's Victory Pt. 02

Blair takes total control.

by GayTripper in NonConsent/Reluctance 08/06/2015
H
4.52
35.7k
16
5
22

Prison Bitch

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

by CollaredandLeashed in Gay Male 01/08/2022
H
4.52
47.7k
46
0
97
0

Prison Pet Pt. 06

Erica's story of submission comes to its conclusion.

by GayTripper in NonConsent/Reluctance 12/20/2014
H
4.52
55.7k
37
6
46

Detention Center FNG

Jillian finds love at the jail.

by IntrovertedDyke in Lesbian Sex 04/21/2020
H
4.52
17.9k
18
5
27
0

Women's Bondage Prison Pt. 09

Lucy continues in her training cell.

by palm09 in BDSM 02/20/2022
H
4.51
19.6k
4
2
8

Seduction at the Old Gaol Ch. 10

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

by AndreaJordan in BDSM 08/13/2017
H
4.51
15.9k
4
0
8

Women's Bondage Prison Pt. 01

Lucy learns who in this bondage prison will violate her.

by palm09 in BDSM 11/06/2022
H
4.51
18.4k
9
1
22

Women's Bondage Prison Pt. 12

Lucy goes on a prison inspection tour.

by palm09 in BDSM 02/22/2023
H
4.51
9k
3
0
13

Unauthorized Entry

Angie gets to live out her fantasy of getting arrested.

by HandcuffedAngie in Fetish 05/26/2021
H
4.51
12.6k
7
2
18
0

Imprisoned by My Fantasy Ch. 02

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

by Jemina004 in Transgender & Crossdressers 07/02/2017
H
4.5
51.3k
47
11
52

Women's Bondage Prison Pt. 02

Lucy progresses in her prison training

by palm09 in BDSM 12/30/2022
H
4.5
16k
6
0
14

The Jail Bunny Ch. 02

Kelli's roleplay with her boyfriend continues.

by HandcuffedAngie in Erotic Couplings 03/05/2024
H
4.5
4.4k
6
2
11

Imprisoned by My Fantasy Ch. 03

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

by Jemina004 in Transgender & Crossdressers 07/10/2017
H
4.5
53.8k
44
10
53

The King's Harem Pt. 04

The King breeds Abrielle then deals with an intruder.

by JeouxCheval in NonConsent/Reluctance 05/19/2022
4.49
59.8k
41
4
71

Ex-Con Uncle was My First Pt. 01

Ex-Con Uncle and nephew get acquainted.

by kwameselinsky in Gay Male 08/10/2021
4.49
46.1k
82
6
135

Women's Bondage Prison Pt. 13

Lucy prepares and begins for prison exercise.

by palm09 in BDSM 04/18/2023
4.48
7.7k
1
0
6

Tooth and Claw

A prisoner gets her comeuppance from a domme...

by AmethystMare in BDSM 09/30/2017
4.47
19.8k
8
0
18
0

Women's Bondage Prison Pt. 07

Lucy works in the prison mill.

by palm09 in BDSM 01/13/2022
4.47
17.1k
6
1
9

Jean - The Birth of Venus Ch. 06

Punishment for her Crimes.

by loerics in NonConsent/Reluctance 04/14/2019
4.47
16.1k
2
2
4

The New Republic

The Republic has a very different type of justice system.

by mish2mash in BDSM 01/17/2023
4.47
14.6k
3
0
18
0

Imprisoned by My Fantasy Ch. 01

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

by Jemina004 in Transgender & Crossdressers 06/30/2017
4.46
87.8k
88
6
136

Bottom Bunk Bitch Ch. 05

Brenda is pimped out the sadistic prison guards.

by Elixurgurl in Transgender & Crossdressers 01/29/2024
4.46
10.5k
10
5
17

Caught in a Spider's Web

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

by Kansas in Lesbian Sex 08/23/2005
4.45
178.6k
63
10
91
0

Prison Pet Pt. 01

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

by GayTripper in NonConsent/Reluctance 08/15/2014
4.45
118.1k
145
5
210

The Cuckold Diet Challenge Ch. 08

The End of the Story.

by FinishTheDamnStory in Loving Wives 10/08/2013
4.45
106.6k
85
255
117

Cobra Crew: Freeing Escobar Ch. 04

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

by hawaiisun in NonConsent/Reluctance 09/16/2012
4.45
41.3k
7
1
14

Timmy's Prison Cavity Search Ch. 04

Timmy takes the HGH mutated prison daddy monster cock.

by smutnut in NonConsent/Reluctance 09/16/2014
4.45
103.9k
57
4
81

Becoming His Prison Bitch

Lexus learns his place behind bars.

by LittleKay in NonConsent/Reluctance 11/12/2018
4.45
82.6k
110
10
159

Roxie & Erica: Blair's Victory Pt. 01

An alternate version of Prison Pet where Blair wins.

by GayTripper in NonConsent/Reluctance 07/25/2015
4.45
46.1k
23
3
36

The Jail Bunny Ch. 01

Kellie gets to live her fantasy of going to jail.

by HandcuffedAngie in Fetish 02/29/2024
4.45
5.3k
7
3
24

The Exhibitionist Pt. 03

The continuing story of a MILF exhibitionist.

by Dr. Bull in Exhibitionist & Voyeur 08/31/2010
4.44
48.8k
14
0
18

Confrontation Ch. 05: Jaguar Nabbed

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

by 1fastguy in Novels and Novellas 10/16/2023
4.44
790
00
2

Locked Up Autumn

Young woman online the day before she reports to prison.

by capecodshark314 in Fetish 08/19/2022
4.44
5k
2
3
10
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