My brother Chris
By pervertedwriter 25 Dec 2025
Bill and Chris have been having anal adventures for years, but this is the first time Chris' cock will penetrate Bill as the perfect Christmas gift for both.
Gay Prolapse Fetish Stories
GayDemon's Stories: On this page you can find erotic fiction where you can read about men with prolapsed ass holes.
Uncle Carter (ch. 2)
By pervertedwriter 21 Dec 2025
Uncle Carter gets to buy Brendon some toys. They start to enlarge the young man's hole and reminisce of the years they lost. Carter decides to keep Brendon as his no mater what it costs.
Uncle Carter
By pervertedwriter 11 Dec 2025
Brendon is a twenty one years old young man who recently came out of the closet. He is sent to spend his summer with his beloved uncle Carter for guidance and mentoring. Carter, who was away for a couple for years, soon discover they both have more feelings for each other than they realized. (The story features extreme anal activities).
A.S.S (Anal Stretching Society) (ch. 7)
By pervertedwriter 10 Dec 2025
Nael takes Leon for a very joyfully anally destructive dinner at the beach. Leon is set on the path to desire and get used to his rougher journey.
A.S.S (Anal Stretching Society) (ch. 6)
By pervertedwriter 9 Dec 2025
Leon and Shiro have their first anal examination while still in the flight. They land on this quite unusual island where the Anal Stretching Society build a paradise for their members and the natives.
His Brother's Sleeve (ch. 2)
By SuddenAgency 24 Nov 2025
Two brothers share an off-campus apartment. What begins as late-night porn and forbidden glances explodes into a three-year obsession: Lucas relentlessly fists, stretches, and destroys Sam’s hole until it becomes a permanently prolapsed sleeve. From first raw fuck to total rectal eversion, their taboo love ends with Sam happily ruined forever.
His Brother's Sleeve
By SuddenAgency 23 Nov 2025
Two brothers share an off-campus apartment. What begins as late-night porn and forbidden glances explodes into a three-year obsession: Lucas relentlessly fists, stretches, and destroys Sam’s hole until it becomes a permanently prolapsed sleeve. From first raw fuck to total rectal eversion, their taboo love ends with Sam happily ruined forever.
A.S.S (Anal Stretching Society) (ch. 5)
By pervertedwriter 14 Nov 2025
Leon keeps his promise to go on the trip, but before they arrive on the private island owned by A.S.S. he meets Shiro and Hans. They go on a very special private jet trip commemorating with Taye for a bit and learning some very special lessons and feelings about anal destruction and brotherly support for sodomy addiction.
A.S.S (Anal Stretching Society) (ch. 4)
By pervertedwriter 7 Nov 2025
Leon wakes up from the ball getting to meet a couple of friends and to sign his contract to officially join the A.S.S.! He confirms his partnership, takes some stretching getting used to the his bright future as a complete anal submission and destruction. (This is a softer chapter, but we will have more extreme stuffing in the next chapters!)
Ivy League Math Papi (ch. 3)
By pervertedwriter 5 Nov 2025
Daniel gets a special surprise from Mateo as they finally get to enjoy each other's bodies in a private setting. A lot of anal perverted acts take place in this joyful destructive probable finale. (I probably won't write more about this couple as I have other stories to post. I can keep doing something with them if they're requested though).
Ivy League Math Papi (ch. 2)
By pervertedwriter 3 Nov 2025
Daniel goes to see Mr. Herrera at his home. He finds himself helping his teacher with a rather wet task.
Ivy League Math Papi
By pervertedwriter 2 Nov 2025
Daniel is a straight A student, but a new teacher causes his grades to go down. They find a solution for it amidst extra classes and tutoring. Daniel discovers Mr. Herrera's secret pictures and messages after his final text; both of them promise to try and meet in a more private setting.
A.S.S (Anal Stretching Society) (ch. 3)
By pervertedwriter 1 Nov 2025
Leon finds Nael and they have their first intimate night together. Despite insecurity, they share their pervertedness finding a deep connection in their love for anal destruction. (I need to ask you guys if you're enjoying the dirty verbal or if I should make it cleaner! Have fun with this more extreme one as requested!)
A.S.S (Anal Stretching Society) (ch. 2)
By pervertedwriter 27 Oct 2025
Leon goes to the Annual Sons of Sodomy Ball to search and find his partner. He meets Gabe, a mysterious black man and encounters Jake and Christian once more. Amidst their traditional dance, Leon finds a charming latino man. (Thanks a lot to the readers who are appreciating and liking my writing!)
A.S.S (Anal Stretching Society)
By pervertedwriter 26 Oct 2025
Lonely and craving connection, Leon discovers an invitation to the secretive A.S.S. (Anal Stretching Society), a group promising brotherhood. He's interviewed by partners Jake and Christian ending up in a test to join the organization. It's the beginning of his extreme anal adventure!
Endless (ch. 13)
By Sam Stefanik 14 Aug 2025
Marvin talked about Tom like some talk about Christ. In many ways, Tom was a Christ like figure for Marvin. Definitely a savior. Marvin still puts Tom's ashtray on the table every night even though he's been dead for centuries. Marvin stopped the story because it's gotten too difficult to tell. Seems like its time for an intermission. Enjoy!
Twink Fisting (ch. 5)
By Fabijan Fistonic 3 Jul 2025
Michael's boy pussy gets brutally wrecked and transformed
Abusive Sissification (ch. 3)
By Kavya sissy 7 May 2025
Me being abused raped and tortured by 8 men for 3 days with no limits and restrictions, Please read part 1 and 2 to know the continuity
Ultimate Anal Stretching Program (ch. 5)
By FFreak13 9 Mar 2025
Sorry for the delay, I wasn't sure where I wanted to take this chapter. It turned out to be more sweet and sensual than previous ones, describing the "spicy" aftercare Jason received after his extreme ass pounding. If that's not your style, don't worry - next chapter will be the usual hardcore anal stretching I know me and you love. Enjoy!
Ultimate Anal Stretching Program (ch. 4)
By FFreak13 17 Feb 2025
Sorry for the delay guys! I've been sick for quite some time, but now I'm finally ready to continue Jason's story. In this chapter our protagonist will test the limits of his mind and body and reach the first of many breakthroughs in his anal stretching journey. Enjoy!
Ultimate Anal Stretching Program (ch. 2)
By FFreak13 22 Jan 2025
In this chapter Jason meets Dr Chen and learns a bit about what he's about to endure during the program. Sorry if there's not enough actual anal stretching descriptions in this one, but I promise I'll kick it up a notch once Jason's training sessions start in chapter 3. Again, let me know in the comments what you think!
Ultimate Anal Stretching Program
By FFreak13 19 Jan 2025
There are a lot of stories here about fisting, but almost none describing the more advanced, extreme aspects of it. My story describes adventures of a young guy set on becoming the ultimate fisting bottom, ready to stretch his hole to unimaginable size and take anything (and I mean anything) up his ass. Multiple chapters planned!
The Kinksters are Alright (ch. 33)
By Alex Ryder 15 Nov 2024
Samuel growled with determination, his thrusts becoming even more powerful. He could feel his orgasm building, the tension coiling tighter and tighter within him. With one final, almighty push, he drove his arms deeper, feeling Jack's body shudder as he came, waves of pleasure crashing over him.
Twink Fisting
By Fabijan Fistonic 22 Oct 2024
A true story about the first time I fist fucked a man that I met at a gay nudist beach
Let them watch then let them gangbang me at the sauna
By Fabijan Fistonic 2 Oct 2024
Anon top at the Sauna fucks me in the chillout area.
Fisting at the Pool
By Baltcumcump 21 Sep 2024
While on vacation in an island in the Caribbean, I met a friend of Bobby’s who lived there. What an amazing experience!
Extreme BoyCunt Island (ch. 2)
By HugeBoyCunt 18 Aug 2023
The story contains scenes of BDSM, fisting, medical procedures, extreme modifications, incontinence, ultimate humiliation, helplessness, huge prolapse. The story tells the case of a guy who ended up on the island of an unknown billionaire, who eliminated an old competition called "the biggest hole".
Fisting Expedition in Rogers Park
By Bryce Manning 1 Apr 2021
Luke's massive hands have always been a struggle for the bottoms brazen enough to attempt them. He finally meets an insatiable guy who rises to the task.
Squat
By YesNow 23 Jan 2021
How my lover finally made me say yes!
Adventures in My Bareback Playroom
By YesNow 22 Dec 2020
This set of stories will try to capture the essence of some of my many adventures in a home playroom. I have had this playroom available to set up in my cellar for almost 15 years. The first man to visit me fucked me bareback. Since then, no condoms allowed. In the years up until the arrival of COVID, the room was in use on average 80 times a year - and all the while I was on the DL!
Trevor
By YesNow 24 Oct 2020
This is a story of a new beginning. An older man who only had sex with other older men meets a 20-year old. What this comes to changes the older man's life. It moves from an awkward, almost reluctant start to a conclusion I wish had been true.
Bikers
By Caliban 2 Apr 2020
JD's sexual boundaries dramatically expand, when he meets a bunch of butch bikers...
Fisted by the Rugby Team
By TallAndDoubled91 3 Sep 2018
A gym bunny takes on the Rugby team and lets them stretch his mancunt to new, unimaginable widths
Cage Fighter
By Caliban 19 Apr 2018
A cage fighter introduces me to extreme sex..