124 Votes
Rael in the Bull Pen
A eighteen-year-old virgin named Rael takes to cock during his weekend stint in jail.
Topics: Anal Sex, DP, Big Dick, First Time, Prison, Slut, Interracial, Boypussy, Virgin, Big Balls, Spit, Deep Throat
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.
A eighteen-year-old virgin named Rael takes to cock during his weekend stint in jail.
Topics: Anal Sex, DP, Big Dick, First Time, Prison, Slut, Interracial, Boypussy, Virgin, Big Balls, Spit, Deep Throat
After nearly forty years in prison, Stanley Blue appears to be the ultimate white daddy top. In and out of prison, he forever longed to be fitted on black dick. Tonight is no different with a younger black top needing to build his confidence.
Topics: DP, Humiliation, Punishment, Prison, Daddy, Interracial, Cum, Grandpa, Age Difference, Degradation, Uncut
After Fatback collects Ralo’s submissive plaything as his sole property, Ralo is left to make do with his nineteen-year-old cellmate Bert. When his lover and fellow cellmate Alistair cuts a deal with Fatback, Ralo is handsomely rewarded with a familiar plaything.
Topics: Black Men, Arab, Group Sex, Prison, Interracial
The erotic exploits of Jack Ladd: prospector and occasional bushranger on the goldfields of Central Victoria, as recounted by himself for the edification and outrage of future generations.
Topics: Anal Sex, Prison, Historical
Cole and Justin's relationship is put to the test.
Topics: Anal Sex, Fiction, Prison, Jock, Twink, Oral & Blowjobs
Cole makes a deal with Warden Parsley.
Topics: Prison, Jock, Twink, Oral & Blowjobs
“Your work is excellent, but you’re leaving that job. You’re going to be turning tricks instead. You did it on the inside, you’ll do it on the outside. You’re still cute a boy and you’re a pro. Interested parties feel your time should be monetized, all will be explained to you…”
Topics: Group Sex, Prostitution, Humiliation, Prison, College, Interracial, Straight Sex, BBC, Rape, Degradation
Fictional Story. A prison ran by favoritism, corruption, and of course, violence. It seems to be a small price to pay for young Cole who desires early release.
Topics: Anal Sex, Forced, Prison, Twink, Oral & Blowjobs
Prison Island with illustrations. It will still be about the boys and the island, but it won't be an exact retelling. This time, I include illustrations I made to support the text.
Topics: Anal Sex, Forced, Prison, Cop, Creampie, Interracial, Twink, Illustrated
“Your dad wanted me to deal with you as I would with any other person we might have arrested, so shut up and comply, and you’ll be out of here soon enough, but continue this nonesense, and you’ll see how we handle disobedience in this precinct”
Topics: Prison, Cop, Twink
Major Collins gets ready for a meeting with Col. Ulrich about the test program. We learn more about Bootlicker.
Topics: Fiction, Prison, Military, Oral & Blowjobs
Scamming a so-called boss chick for my hot hung prison daddy
Topics: Black Men, Prison, Daddy, Power Bottom, BBC, Domination, Submission
Ryan wakes up after his preparation back in his cell and starts to understand exactly what the Facility is all about...
Topics: Piss, Chastity, Bondage, Abduction, Forced, Humiliation, Prison, Doctor, Degradation, BDSM, Control, Pain, Cock Cage
My stepfather shares me with his ex-prison buddy...
Topics: Anal Sex, Group Sex, Prison, Daddy, Felching
A feisty straight boy becomes a prison bitch...
Topics: Anal Sex, Prison, Oral & Blowjobs
What started out for me as hopefully a fun night out having some hot sex, turned out to be just that, but not how I would have planned it.
Topics: Anal Sex, Prison, Cum, Oral & Blowjobs, Gangbang
A sailor is incarcerated in the ship’s brig. Re-educated by motivated marines, he receives special attention and learns valuable lessons.
Topics: Anal Sex, CBT, Prison, Military, Oral & Blowjobs, Discipline, Gangbang, Control, Marine
TW: Noncon, abuse, suicide, psych ward Admission and orientation - Whynne is admitted to a criminal psych ward for noncompliance and assigned a sadistic doctor to manage his treatment.
Topics: Forced, Prison, Doctor, Mind Control, Master & Slave, Domination, Flogging, Intersex
Jamie was a simply jock, dominating me and fighting other thugs with his bare powerful feet
Topics: Wrestling, Prison, Feet, Jock, Domination
(Edited complete version) An interview turns intimate, and Chester Mansfield finds himself caught up in a rushing whirl of lust, sex and drugs with a handsome, horse-hung ass-pounder who turns his well-ordered world upside down
Topics: Black Men, Prison, Cop, Drugs, Infidelity, Bareback, BBC, Lust
1994 was the year Iwas sent to prison! Clean cut straight 29 yr old white guy. After spending time peter gazing in the showers for a few weeks I had noticed this black guy with a enormous flaccid cock. I often fascinated about being raped by black guys before actually getting to general population since you hear and see it in movies.
Topics: Black Men, Big Dick, Prison, Interracial, BBC
"Love from the past" - Beau and Jorell fly to San Quentin, where many secrets are revealed. While waiting in the limo for the two men to come back, LaShawn... deepens his acquaintance with Joshua, the hunky (and straight) jet pilot and limo driver. At the Cove, Wahkan is 'invited' to an event he dearly would like to miss.
Topics: Anal Sex, Fiction, Handjob, Romance, Prison, Twink, Age Difference, Love
Dwaine's even cockier, more dominant behind bars
Topics: Rough Sex, Prison, Smells, Oral & Blowjobs, Domination
20 year old prisoner Dwaine is: rough, cocky and handsome. He wants to own me.
Topics: Muscle, Masturbation, Prison, Smells, Lust, Body Worship
"Venture into the Unknown" - Barry finally faces his trial... with an unexpected outcome. The last night with Wade is heart-warming and cock-hardening at the same time. When he eventually goes back home, to the Cove, he will need all the sympathy and affection Kale can give him…
Topics: Anal Sex, Fiction, Straight Men, Romance, Prison, Virgin, Oral & Blowjobs, Age Difference, Love, Cum Denial
Nick Kennedy is sentenced to "The Scarlet Letter" - an intense punishment designed by the government to teach young men about the consequences of their actions.
Topics: CBT, Chastity, Humiliation, Prison, SM, Discipline, Degradation, BDSM, Shaved, Pain
That Interview Room was a closed set, a one-on-one challenge that Rashid and Captain Harding would play out this power game, with few rules and fluid roles that needed to be determined.
Topics: Prison, Cop, Interracial, Role Play, BDSM
"On Strike" - A quarrel explodes between Rick and his man Stewart and the boy goes on strike, refusing to perform his duties, both in the kitchen and in bedroom. In jail, a strong bond is forged between Barry and the straight young cellmate Wade, who in the end doesn’t back off when it comes to doing ‘something gay’ with his hero…
Topics: Anal Sex, Fiction, Straight Men, Romance, Prison, Virgin, Age Difference, Love
The inmates, now sentenced to be there for life, continue to be humiliated, degraded and used at the Labour Camp. Our narrator runs into someone he knows, which just makes things worse.
Topics: Piss, Anal Sex, Spanking, Humiliation, Prison, Bastinado, Fucking
Chris experiences more and more of the depravity and degradation of the labour camp - thrashed, drained and put to work, he learns about the horrors and pain of The Hole and learns a terrible thing about his own future
Topics: Piss, Anal Sex, Humiliation, Prison, Pain, Bastinado, Fucking