Gay Diaper Dildo Stories

138 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Our Night Together Ch. 02

by HappyGerman on Aug 18, 2017
Gay Male

The next day dawned bright and early at 8 AM with my cell phone alarm chiming. I clicked it off and looked at the floor to see Allen, my new slave, lying there in a diaper. His cock was creating a bulge in it from his morning wood, and I salivated at the thought of it. I crawled over to him in my doubled up diaper (which I had soaked again during the night)...

Should Not Have Stopped

by pampersub on Aug 18, 2017
Gay Male

I had gotten a job in South New Jersey, not bad, right after law school. It took me awhile to clean out my old apartment so I did not get to leave on the road until Saturday morning. I was a little angry at myself for waiting so long, my plan was to get to a hotel on Friday night then check out the bar scene all Saturday and Sunday, pick a new place based...

Best (Fuck Buddy) Friends

by gregshaw on Aug 18, 2017
Gay Male

I met Chris out of college, playing a game of pick up basketball during lunch break at my first job. We were both the jock type, shared the same sense of humor & hit it off immediately. He was blonde, blue eyed from a long line of Norwegians, while I was black haired & green eyed from a wide mix of East Europeans & God knows what else. Despite this people th...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

Inside of You

by Cia81 on Sep 25, 2017
Gay Male

"Anyone can catch your eye, but it takes someone special to catch your heart." ~Author Unknown. * Jerret took a sip of his soda before he set it down. His fingers slid idly over the condensation on the glass as he stared around the restaurant at all of the happy couples. He was seated at a small table in the back, which was obviously not a prime date locat...

Toledo's Turn

by toddstop on Aug 18, 2017
Gay Male

Chapter 1 "Hey, Tol, get your ass moving! I need to get home." Uncle Dan's voice boomed from behind me like an old-time radio baseball announcer. I could just imagine him lugging the giant cooler he brought his lunch and snacks in as he headed for his truck. He'd seen me and knowing that I was caught, even though there was nothing to catch me at, I felt a b...

30-Days of House Arrest Ch. 01

by bjmichaels on Nov 27, 2017
Gay Male

Everyone wants me to admit I have a drinking problem. My lawyer said it is an important part of the plea agreement; my boss told me he'd keep my job open and I can return to work after my 30-day house arrest. Okay, sure, fine...sometimes I get a little hammered after work and on my day off but who doesn't? Anyway, I got into this mess because the cops said...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

It's Not as Secret as You Think

by datura48 on Mar 17, 2020
Gay Male

Warning: This story contains incest. Author's Note: This is an expansion and retelling of the previously posted story "Home Repairs." ***** Stephanie rolled her eyes listening to the boys tell their tales for the umpteenth time. Even though they got together just about every weekend, it was always the same thing and the same stories with them. However, de...

Turned Out on a Bet Ch. 03

by Coxswain on Sep 19, 2017
Gay Male

TURNED OUT ON A BET, PT. 3 In which the best-laid clans of men often go astray The Seventh-Inning Stretch How does the saying go?--The balls have reasons that reason itself knows not of? I was in a funk. Mess hall coffee tastes even worse when your head spins with an impossible scheme. It was a simple question, really: How do I stretch the asshole of an u...