Gay Strap-On Dildo Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about men fucked with strap-on dildos.

Anal Ravaged by Uncle Jack and the Apple Farm (ch. 3)

By Mr.X 26 Apr 2026

Cassi finally gets expanded to take Uncle Jack's double fists past the elbows. Lots of strapons, dildos, and fuck-machines. More cum than an ocean. More surprises for Cassi on the path to meeting the other boys for their future band. Cassi begs to be given a rosebud--after all, he gave Uncle Jack a fisting like never before!

9.8 (20) 1323 34 Min Comments

Journey from bicurious to bicuckold slut for BBC (ch. 3)

By Bicuck4bbc 27 Mar 2026

The progression continues. The first time being ass fucked by a strapon and cock cravings it unleashed

7.4 (12) 851 5 Min Comments

Alpha & Omega (ch. 9)

By The Magic Wand 22 Feb 2026

This is a cut scene that was originally intended to be Chapter 9. In it, Jacob returns home to visit family. When he gets together with his ex-girlfriend, Mia, their reunion turns unexpectedly steamy, and she takes his new Omega abilities for a test drive. When her boyfriend comes home, he joins them in a hot threesome they'll never forget

9.2 (31) 2198 12 Min Comments

Mob Abduction

By BigJohnDoe 18 Dec 2025

After a date with a known daughter in the mafia, he wakes up in her sex room to be used in every pleasure imaginable...

7.5 (23) 2664 9 Min Comments

A Dildo in the Wash, Reels in the Twins (ch. 5)

By Mr.X 16 Dec 2025

Pete's head is spinning. He can't fathom the sex happening with these two Gorgeous Twink Twins and Adam. Some fears about the Twins' past and whether he is doing the right thing are put to rest as the Twins plead for adult Training and wish for their friends, once they are 18, to join. It will be the 25th Floor Private 18+ Gay Boys BDSM Sex Club!

9.6 (49) 1847 21 Min Comments

Femoby catfished by a Femdom and her Lover

By Sissyslutgurl69 11 Nov 2025

Feminized sissy gets tricked by an aggressive mean Femdom.

9.2 (18) 3857 54 Min Comments

Goth Twink Punk Breeding (ch. 7)

By Mr.X 23 Apr 2025

Yes I am back! Miss me? This one goes out to "The Donling"...I hope you enjoy it! This was a lot of fun researching and very fascinating. Yes, it is possible. Tyler and Mark cum for the 18th Birthday catch up Fuck & Fist Fest...see what goes up and down! So Cool!

9.9 (29) 2032 31 Min Comments

Swimming Pools and Sleepovers (ch. 5)

By Mr.X 6 Nov 2024

The five 18 year old Twinks and Doctor Parker have incredible ejaculations with the massive dildo toys, cocks cages, and of course, fists, hands and arms. Matt Fucks, the Dr... Garrett is led away for a private Threesome with Evans's Parents. Aaron, and the remaining go back to their 18 years old sleepover Twink TB-Pad fuck fest.

9.8 (28) 2927 20 Min Comments

Boy Bonding Cave Dungeon (ch. 38)

By Mr.X 3 Aug 2024

The 8 BBCD Collectives are BDSM ravaged by the Promenade orgy Twinks. Josh and Cathy has a surprise for ALL the boys. Dylan and his Mom will....

9.3 (19) 992 10 Min Comments

Boy Bonding Cave Dungeon (ch. 35)

By Mr.X 13 Jun 2024

The Boy Bonding Cave Dungeon Collective Erotica group decides to scratch one of the group fantasies off their wishlist. Anal lust and cum explosions erupt as the boys reveal their true wish of what they all want to do with other boys!

9.4 (24) 2197 20 Min Comments

Boy Bonding Cave Dungeon (ch. 14)

By Mr.X 12 Mar 2024

The pledge and initiation of 18-year-old Jordan transform the boy into the "Houseboy". Now, he is called Ginger-Jordy, Houseboy, and anal slut; slave in the House of Master Dylan, to serve the cum needs of the Masters of the BBCD Collective!

9.4 (40) 1598 37 Min Comments

Femboi Saves The World (ch. 8)

By Mr.X 4 Dec 2023

Finally, the uber ultimate group fisting cum. But more adventure awaits the group and the newfound God!

9.5 (34) 1291 36 Min Comments

The Hole (ch. 2)

By WantonOne247 9 Nov 2023

The morning after the furry fuckfest and discoveries

7.9 (14) 2992 7 Min Comments

The Hole

By WantonOne247 6 Nov 2023

Sam and Dean go to a furry convention in Vegas

9.0 (16) 5115 7 Min Comments

The Hole (ch. 3)

By WantonOne247 30 Oct 2023

waking up to the morning after to new experiences and a new future

8.8 (18) 3225 4 Min Comments

The Hole (ch. 2)

By WantonOne247 29 Oct 2023

Sam finally knows who his mystery fucker is and he couldn't be happier.

9.1 (14) 2782 4 Min Comments

wife mademe a pathetic sissy cocksucking slave

By BillyBoy 13 Sep 2023

my new wife wasn't what she seemed. she turned me into a sissy, then a strap-on fuck toy, then brought in men to fuck her while i watched, then men to fuck me while she watched. It's a long story, but I'm caught up here forever now.

8.2 (70) 13640 9 Min Comments

Caught and turned out (ch. 2)

By gary_4_u 7 Oct 2022

We met with Karen and Stan almost weekly now with Susan and Karen having us guys doing more and more together for their pleasure. It was usually just us sucking each other off then pleasuring them. But lately they started fucking us with strap on dildos. This was done either at home or with each other together.

8.9 (49) 6362 5 Min Comments

My Neighbor's Wife

By BillyBoy 11 Mar 2022

My neighbor's wife is crazy. She turned me into a cock loving sissy whore for her husband.

8.9 (78) 12313 7 Min Comments

The Couple

By BillyBoy 9 Mar 2022

Dave and his wife are swingers of sorts. They like to bring sissy guys in for her strap-on dildo fuck while he throat fucks them. She likes to watch him suck off other guys. She likes to watch him get fucked, too. It was a crazy weekend!

8.6 (17) 3661 8 Min Comments

What Happens In Vegas, Stays In Vegas

By Disbtm 5 Feb 2022

A tale about four young men and their trip to Las Vegas. A story of sex, sex and more sex. Straight, Gay, Bi, and more.

9.1 (16) 3407 18 Min Comments

What is a cockold? Now I think I know.

By BillyBoy 30 Sep 2021

My first wife was a bitch. She put me through hell. But the second one put me through something worse. Watching her boyfriend fuck her while I was bound and gagged and tied to a chiar in the bedroom. Maybe my third wife will be nice to me.

7.6 (17) 2225 7 Min Comments

Rising Again (ch. 3)

By Unknownanon 4 Jun 2021

Reminder to never hookup with a straight tweaked out guy who says he likes gay sex and is willing to share his stash with you.

8.4 (13) 2198 8 Min Comments

My wife watched as I got fucked by a big cock

By Bob Long 25 Sep 2020

This is the true story how my wife thought it was time I learned a lesson and this was her payback for the things I made her do and took for granted

8.9 (39) 24782 18 Min Comments

Something Different (ch. 15)

By RJC 7 Aug 2020

With that curved cock I knew he would be finding all my spots.

9.6 (43) 1363 5 Min Comments

I Love using Strap on Dildos

By bizarrebodymods 18 May 2018

I love using strap-ons and silicone cock sleeves, but this time I ended up getting one permanently.......

7.8 (35) 6362 6 Min Comments