Gay Prison Sex Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about gay sex in prison and jail or men used as prison bitch listed by date.

9.6
85 Votes

Turning Out Pretty Boy (ch. 9)

Story by Colton

21 Oct 2020 12576 Readers comments 38 Min Read

Sunshine's story of being turned out in prison concludes… As we dressed, I summoned the courage to apologize. “Sir, I’m really sorry about last night. I should have known better. I did know better. How can I make it up to you?” Jaxx frowned as if I were asking an absurd question. “You can’t, Sunshine. You’ll pay… later.” With that, he strode off.

Topics: Black Men, Rough Sex, Big Dick, Prison, Interracial, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, BBC, Domination, Blond

8.3
42 Votes

Gay in Prison, life behind the wall

Story by Stallaction

19 Oct 2020 5373 Readers comments 8 Min Read

An ongoing series about being gay and in prison. It's not Oz or Law & Order...this is the true side of being a gay inmate. Witness the journey of Kevin as he enters this new world and how he tries to adapt, survive, and thrive.

Topics: Black Men, Shower, Prison, Interracial, Love

9.4
49 Votes

Turning Out Pretty Boy (ch. 8)

Story by Colton

7 Oct 2020 9944 Readers comments 21 Min Read

Jaxx told me to expect to be passed around to other inmates and some of the guards. So I wasn’t all that surprised when it began to happen, particularly given that Aidan had started pimping me out on Friday nights. I’d been in the prison for maybe a month when Jaxx whored my holes to one of Black Godz for the first time...

Topics: Black Men, Rough Sex, Big Dick, Prison, Interracial, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, Domination, Blond

7.9
39 Votes

The jailhouse romance with a bratty inmate

Story by Stallaction

1 Oct 2020 2226 Readers comments 8 Min Read

Can you fall in love while in jail? "Gay for the stay" is one term used to describe how men form relationships behind bars. This story is about two young inmates who are figuring each other out. If you ever wondered how life in jail/prison is like, this is the unvarnished truth. PS: I still talk to Jack to this day.

Topics: Romance, Prison, Interracial, Sex, BBC, Love

9.5
62 Votes

Turning Out Pretty Boy (ch. 7)

Story by Colton

23 Sep 2020 10464 Readers comments 20 Min Read

Prison was tedious, but tolerable, as I spent my time reading and studying – something I never did much in school – working out and killing time in my job in the prison infirmary. Of course during a good chunk of that time my holes were filled with a dick. At first it was only Jaxx’s big black cock, but over time that changed, starting with the first Friday night I spent in gen pop.

Topics: Black Men, Rough Sex, Dildo, Big Dick, Prison, Interracial, Alpha Male, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, Domination, Blond

7.7
49 Votes

The Latin Connection

Story by Bert LaVey

14 Sep 2020 3576 Readers comments 4 Min Read

I'm in jail and the heat and tension is building up between me and the only other guy in the cell, a hot Latin guy who seems to have the hots for me, but...

Topics: Latin Men, Anal Sex, Big Dick, Prison

9.6
71 Votes

Turning Out Pretty Boy (ch. 6)

Story by Colton

9 Sep 2020 12825 Readers comments 19 Min Read

The guards retreated from the cell block. I’d been eagerly anticipating Jaxx buttfucking me once the lights went out, particularly after hearing Aidan gush about getting boned by Jamar, but Jaxx apparently wasn’t interested. Of course, my boi butt was sore after the Black God busted my cherry, so it could use a night off. But moments after the echoing footsteps died, he was next to my bed…

Topics: Black Men, Rough Sex, Big Dick, Prison, Interracial, Alpha Male, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, Domination, Blond

9.5
67 Votes

Turning Out Pretty Boy (ch. 5)

Story by Colton

2 Sep 2020 13597 Readers comments 28 Min Read

Jaxx tugged off his towel, exposed his amazing body. “You left your ass juices on my cock this morning, slut. You know what to do.” I’d never had a dude’s dick in my mouth and sucking a cock would be another first for me. I didn’t hesitate, although in the back of my mind I reasoned that if he really wanted his cock cleaned, he could easily turn on the shower. That obviously wasn’t ...

Topics: Black Men, Rough Sex, Big Dick, Prison, Interracial, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, Domination, Blond

8.8
67 Votes

Prison farm

Story by GayCumSluts

27 Aug 2020 12425 Readers comments 15 Min Read

Getting fucked by guards and criminals at the local prison farm.

Topics: Piss, Public Sex, Rough Sex, Dildo, Fisting, Prison, Cum Dump, BDSM, Fucking

9.6
103 Votes

Turning Out Pretty Boy (ch. 4)

Story by Colton

19 Aug 2020 19549 Readers comments 21 Min Read

Jaxx slowly pulled his big black cock from his pants. I almost swallowed the socks stuffed in my mouth. He had the biggest slab of meat between his legs that I’d ever seen, and it was still soft. He clutched it with one hand and swung it into the palm of his other hand, inches in front of my eyes, causing a loud, smacking sound. I was witnessing a weapon being prepared for battle.

Topics: Black Men, Rough Sex, Big Dick, Prison, Interracial, Alpha Male, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, BBC, Domination, Blond

9.1
93 Votes

Turning Out Pretty Boy (ch. 3)

Story by Colton

12 Aug 2020 41152 Readers comments 28 Min Read

It was bad enough that the prison guards uniformly hated me, and seemingly every inmate was intent on scoring my ass and turning me into a trophy fuck because of my teen-model looks, surfer blond hair and bubble butt. No, on top of that I had to fuckup. Not just a run-of-the-mill fuckup, either. Instead it was a disastrous one involving one of the prison's Black Godz. I was so screwed...

Topics: Black Men, Rough Sex, Big Dick, Prison, Interracial, Alpha Male, Cum Dump, Bareback, Boypussy, Bubble Butt, Master & Slave, Domination, Blond

9.1
86 Votes

Turning Out Pretty Boy (ch. 2)

Story by Colton

29 Jul 2020 17067 Readers comments 18 Min Read

Life in prison and being locked up in tight quarters was getting to me. I don't know which was worse - listening to my hayseed roommate Aidan rave about getting buttboned by one of the studs he called the Black Godz, or hearing him detail how my looks would make me a a prime target for a prison trophy fuck. The pressure was messing with my head.

Topics: Black Men, Rough Sex, Big Dick, Forced, Prison, Interracial, Alpha Male, Cum Dump, Bareback, Boypussy, Master & Slave, Domination, Blond, Spit Roasting

8.9
105 Votes

Turning Out Pretty Boy

Story by Colton

16 Jul 2020 34899 Readers comments 28 Min Read

I never expected to land in prison, only days after my 18th birthday, and be told by my cellmate that I'd be targeted by other inmates as a trophy fuck because of my surfer blond hair and pretty boy looks. His words echoed in my mind. "Inside you can fight, get fucked or climb a tree... and there ain't no trees."

Topics: Black Men, Rough Sex, Big Dick, Forced, Prison, Interracial, Alpha Male, Cum Dump, Bareback, Boypussy, Master & Slave, Domination, Submission, Blond, Control, Coming of Age, Spit Roasting, Cum Swallow

8.6
73 Votes

Raped by Rick (ch. 2)

Story by Sharkboy

21 Jun 2020 9816 Readers comments 27 Min Read

Held captive by Rick and his gang, Mark and I are fucked mercilessly over and over. When an opportunity arises, we attempt to escape - only to get caught! This time, we are edged while bound and gagged - but with a dangerous twist: the moment we cum, it will be the end of us: chocked to death! Will we escape, or give the cumshot of a lifetime?

Topics: Bondage, Big Dick, Group Sex, Forced, Prison, Edging, SM, Rape, Gangbang

9.0
45 Votes

Seeking Shelter

Story by JasonRiley

8 Jun 2020 3680 Readers comments 5 Min Read

A rainy day leaves me well and truely fucked, just when I thought it couldn’t get any worse I end up in prison, in more ways than one.

Topics: Public Sex, Chastity, Bondage, Dildo, Leather, Prison, Spit Roasting

8.9
501 Votes

Prison Prey

Story by Caliban

28 Apr 2020 11060 Readers comments 12 Min Read

Warden Harris gives Bruno a special thank you gift, when Nathan arrives in prison...

Topics: Latin Men, Anal Sex, Prison, Interracial, Oral & Blowjobs, Master & Slave

9.2
15 Votes

Prison Tales (ch. 12)

Story by Gazzaq

19 Apr 2020 2240 Readers comments 17 Min Read

Jake tells his Rugby Pal Dikran about his new Job and secrets are shared and they cross the line.

Topics: Arab, Anal Sex, Big Dick, Spanking, First Time, Prison, Virgin, Rugby Player

8.8
9 Votes

Prison Tales (ch. 11)

Story by Gazzaq

15 Apr 2020 1819 Readers comments 9 Min Read

Chapter 11 Prison Volunteers Interviews Jake Gets Fucked

Topics: Black Men, Anal Sex, First Time, Sloppy Hole, Prison, Role Play, Virgin

9.1
11 Votes

Prison Tales (ch. 10)

Story by Gazzaq

14 Apr 2020 2153 Readers comments 12 Min Read

Prison Volunteers Interviews Commence

Topics: Black Men, Arab, Anal Sex, DP, Dildo, Group Sex, Sloppy Hole, Prison, Creampie, Cum Dump, Role Play, Virgin, Oral & Blowjobs

9.0
17 Votes

My Papi (ch. 28)

Story by Nyguy

23 Mar 2020 2334 Readers comments 5 Min Read

My uncle's 23-year-old-white prison bitch got released and there was a reunion.

Topics: Anal Sex, Dildo, Prison, Uncle, Twink, Oral & Blowjobs, Master & Slave

9.1
18 Votes

My Papi (ch. 26)

Story by Nyguy

5 Jan 2020 2226 Readers comments 6 Min Read

"You can start by getting on your knees and I'll talk you through sucking my dick." My father and uncle helped me out with a young straight white guy who hired me to train him to be a prison bitch.

Topics: Black Men, Anal Sex, Prison, Uncle, Incest, Oral & Blowjobs

9.1
20 Votes

Prison Tales (ch. 9)

Story by Gazzaq

11 Nov 2019 6088 Readers comments 14 Min Read

Aaron and Anthony share a Cell and the Governor has special favour to ask

Topics: Group Sex, Sloppy Hole, Prison, Creampie, Cum Dump, Felching, Power Bottom, Bubble Butt, Blond

9.1
20 Votes

Prison Tales (ch. 7)

Story by Gazzaq

27 Oct 2019 2828 Readers comments 10 Min Read

First Time Prison Blond Bubble Butt's Officer Nick Browns Story   Officer Nick Browns Story continues

Topics: Anal Sex, Dildo, Big Dick, Group Sex, Prison, Bubble Butt, Blond

9.4
26 Votes

Prison Tales (ch. 5)

Story by Gazzaq

25 Oct 2019 4142 Readers comments 19 Min Read

James a First Time Prisoner meet Tyler whose Jealousy nearly ruins their Prison Relationship

Topics: Black Men, Latin Men, Anal Sex, Big Dick, Romance, Sloppy Hole, Prison, Relationship, Infidelity, Cum Dump, Boypussy, Virgin, Oral & Blowjobs

9.1
30 Votes

Caged (ch. 3)

Story by Stipa

18 Oct 2019 3080 Readers comments 24 Min Read

While Jonah is struggling with the aftermath of the events from the shower, Ashley on the out side of the Prison tries figure out how Jonah ended up in Prison in his Brothers place.

Topics: Anal Sex, Brothers, Prison, Interracial, Alpha Male

8.6
121 Votes

Caged

Story by Stipa

29 Sep 2019 14088 Readers comments 19 Min Read

Jonah get's in the Prison and needs protection which his cellmate offers.

Topics: Black Men, Anal Sex, Prison, Infidelity

9.0
38 Votes

Prison Tales (ch. 4)

Story by Gazzaq

20 Aug 2019 4820 Readers comments 14 Min Read

Aaron Settles in Nicely and has a Family Visit

Topics: Anal Sex, Big Dick, Group Sex, Sloppy Hole, Prison, Face Fuck, Cum Dump, Oral & Blowjobs

8.8
63 Votes

Prison Tales (ch. 3)

Story by Gazzaq

30 Jul 2019 6979 Readers comments 13 Min Read

Part 3 Aaron's Taken Again

Topics: Arab, Anal Sex, Big Dick, Group Sex, Prison, Oral & Blowjobs

9.0
72 Votes

Prison Tales (ch. 2)

Story by Gazzaq

27 Jul 2019 8634 Readers comments 8 Min Read

Aaron gets introduced to the pleasures that being Fucked Deep in the Ass can bring

Topics: Anal Sex, Rimming, Group Sex, Prison, Virgin, Oral & Blowjobs, Bubble Butt, Blond