Gay Pegging Stories

GayDemon's Stories: On this page you can find erotic fiction where you can read about Men getting fucked with a strap-on dildo listed by date.

9.2
34 Votes

The Secret of Skofield Island

Story by Randy Rogue

27 Feb 2024 1442 Readers comments 15 Min Read

What really goes on at Skofield Island? Why do the woman outnumber the men ten to one? And what are woman really doing to men behind closed doors? Find out in this quick sexually exciting read of how the fairer sex really wants to change the world, for the better.

Topics: Rough Sex, Poppers, Dildo, Bisexual, Blond, Ass Play, Spit, Pegging

9.3
15 Votes

My Evolving Transition

Story by Fatbottom1967

17 Dec 2023 1474 Readers comments 8 Min Read

Introduction: I had lived in a loft behind my mom’s subdivided house. Until I met my girlfriend, I didn’t know whether I was a Jack or a Jill or both, while also being a shy virgin. Here begins the journey.

Topics: Bisexual, Pegging

9.3
15 Votes

Training the Femboy (ch. 8)

Story by Arbseveninch

4 Dec 2023 1012 Readers comments 35 Min Read

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

Topics: Piss, Chastity, Dildo, Fisting, BDSM, Femboy, Pegging, Fuck Machine, Cum Eating

8.8
11 Votes

The Hole

Story by WantonOne247

6 Nov 2023 2637 Readers comments 7 Min Read

Sam and Dean go to a furry convention in Vegas

Topics: Anal Sex, Dildo, Transgender, Sci-Fi, Pegging, MTF, Body Modification, Furry

9.0
22 Votes

My Wife's New Tool

Story by Disbtm

31 Oct 2023 2760 Readers comments 6 Min Read

A very perverted, and sexually craved husband and wife wake to find she has grown a beautiful cock. They're not sure how, but they will have fun while it's here, and very hard. A fantasy I dreamed about over and over when I was married. Why can't she have a cock?

Topics: Piss, Anal Sex, Crossdressing, Drugs, Fantasy, Transformation, Oral & Blowjobs, Pegging, Fucking

8.7
12 Votes

The Hole (ch. 3)

Story by WantonOne247

30 Oct 2023 1636 Readers comments 3 Min Read

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

Topics: Piss, Dildo, Fisting, Transgender, Ass Play, Pegging, FTM

9.4
11 Votes

The Hole (ch. 2)

Story by WantonOne247

29 Oct 2023 1228 Readers comments 4 Min Read

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

Topics: Dildo, Transgender, Ass Play, Pegging, FTM

8.2
36 Votes

wife mademe a pathetic sissy cocksucking slave

Story by BillyBoy

13 Sep 2023 5678 Readers comments 9 Min Read

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.

Topics: Bondage, Sissy, Straight Sex, Domination, Pegging

9.2
50 Votes

Summer Scholastics

Story by LaetusBF

11 Mar 2023 6744 Readers comments 9 Min Read

A young man's fantasies become reality after a fateful run in with his Highschool English Teacher.

Topics: Piss, Teacher, Chub, Seduction, Bathhouse & Saunas, Age Difference, Ass Play, Uncut, Pegging

9.5
57 Votes

Old Man Henry

Story by Randy Rogue

1 Mar 2023 1648 Readers comments 10 Min Read

A perverted vampire story written with the help of a friend. I think it’s the most entertaining story I’ve written yet. You should dig it the most!

Topics: Rimming, Bisexual, Vampire, Horror, Pegging, Supernatural, Marine

8.7
21 Votes

For the Love of Big Black Cock

Story by Randy Rogue

30 Jan 2023 2663 Readers comments 16 Min Read

Story about a night when a white and black coworker get a visit from two horny woman.

Topics: Rough Sex, Rimming, Bisexual, Interracial, BBC, Raunchy, Pegging

9.0
62 Votes

My Neighbor's Wife

Story by BillyBoy

11 Mar 2022 7767 Readers comments 7 Min Read

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

Topics: Anal Sex, Dildo, Neighbour, Bisexual, Oral & Blowjobs, Pegging, Husband

7.6
23 Votes

Cockold. What is that?

Story by BillyBoy

22 Oct 2021 3606 Readers comments 6 Min Read

Cockold? I guess I shouldn't have asked. But she was already into it big time. It was too late for me. And it still is.

Topics: Bondage, Cuckold, Married, Pegging

8.3
17 Votes

I married a fat girl

Story by BillyBoy

8 Oct 2021 3543 Readers comments 5 Min Read

I only found out much later that she set me up to catch me in her undies and tricked me into becoming a sissy peg boy and later a slut for her x boyfriend who she was still fucking. I guess that is the whole story, actually!

Topics: Crossdressing, Bondage, Rimming, Straight Sex, Chub, Oral & Blowjobs, Married, Pegging, Tricked

7.5
16 Votes

What is a cockold? Now I think I know.

Story by BillyBoy

30 Sep 2021 1700 Readers comments 6 Min Read

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.

Topics: Crossdressing, Bondage, Dildo, Cuckold, Pegging

8.7
81 Votes

His Sister's Friend

Story by rocketboy

14 Aug 2021 6239 Readers comments 3 Min Read

Toby has a huge crush on his sister's friend and coworker, and a huge crush on his giant bulge. What he doesn't realize is that the "straight" guy he thinks he knows might actually be more open than he thought.

Topics: Straight Men, Big Dick, Jock, Gym, Pegging

7.3
12 Votes

Rising Again

Story by Unknownanon

1 Jun 2021 1720 Readers comments 5 Min Read

Some details/characters inspired by my own life experiences. Premise: Leon, my husband, leaves for a week for a party and I am left to my own devices. I resort back to my old ways. Will Leon ever find out?

Topics: Dildo, Bisexual, Infidelity, Hookups & Dates, Pegging, PNP, Fucking

9.5
39 Votes

Through his balls (ch. 9)

Story by Silent Thunder

5 Apr 2021 2355 Readers comments 10 Min Read

He came out of the bathroom and walked up to me. He put his hand on the side of my check and directed my face to his cock. I immediately took his soft cock into my mouth and started to suck him. I love feeling Sir grow in my mouth! All his glorious length and girth filling me up. I could feel my own dick straining in my hand! This is worse than a chastity cage!

Topics: Piss, CBT, Chastity, Bondage, Dildo, Oral & Blowjobs, Master & Slave, Age Difference, BDSM, Pegging

9.1
23 Votes

New Army Boi (ch. 3)

Story by BatorBoiPorn

9 Mar 2021 3609 Readers comments 11 Min Read

You wake up with the other recruits, most of them with tents pointing straight from their crotches, but none of you have time to deal with them. You turn onto your side, looking at your clothes. You rub the sleep from your eyes and as your vision focuses your stomach drops through you. On top of the pile is your key, snapped in half. Shit, you think.

Topics: Piss, Chastity, Dildo, Military, Edging, Pegging

9.1
10 Votes

Straight Man - Capital Asset (ch. 8)

Story by Luke

24 Nov 2020 900 Readers comments 11 Min Read

Dan returns home, at least it looks like home, and it looks like his wife. But its all so different!! Visitors, a lovely '89 and another man WTF!!

Topics: Straight Men, Master & Slave, Domination, Control, Pegging, Straight to Gay

8.9
29 Votes

My wife watched as I got fucked by a big cock

Story by Bob Long

25 Sep 2020 17976 Readers comments 17 Min Read

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

Topics: Anal Sex, Straight Men, Voyeurism, Punishment, Bisexual, Oral & Blowjobs, Cuckold, True Story, Pegging

9.0
24 Votes

Ghost Hunk

Story by Oddballs

11 Jul 2020 7002 Readers comments 29 Min Read

A horny ghost finds himself a handsome young man to possess. A well built jock of 26, Blake is in for the weirdest experience that he's never wanted to even screw with in a gay phantom that loves to get kinky and mess with a straight man like him. Antics get a bit whacky, as the ghost likes to play with his victims.

Topics: Anal Sex, Spanking, Masturbation, Humour, Ghosts, Horror, Control, Pegging

8.8
4 Votes

Turning the tables (ch. 3)

Story by naaru

6 Jun 2017 1667 Readers comments 7 Min Read

Vicky has Tyler and Jeremy at her mercy. Continuation of "Turning the Tables - Dirty Boys - Closet"

Topics: Anal Sex, Bisexual, Pegging, Boss

8.7
23 Votes

The Halfway Inn (ch. 2)

Story by Robert Furlong

8 Dec 2014 2023 Readers comments 42 Min Read

The conclusion of what happened during my hotel stopover with a younger colleague...

Topics: Rimming, Docking, Co-worker, Hotels, Pegging