Gay Diaper Punishment Stories

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Orientation
Length
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Infinite Scroll

Double Punishment

by Guy521 on Oct 8, 2019
Gay Male

Adam and Charlie sat silently outside the headmasters office, contemplating what was about to happen. Both young men had been caught fighting yet again, leaving Adam with a split lip and ripped shirt, and Charlie with a bruised eye. The sound of the headmaster's door opening signalled for the boys to enter. The Headmaster stood behind his desk looking less...

Shawn's Punishment Pt. 02

by Guy521 on Jul 31, 2019
Gay Male

Master led Shawn to the basement, a very familiar place to Shawn. It was here that he had been trained by his master, worshipped his master and been used countless times. Tonight he was here to be disciplined. He had been disciplined before, but Master had was incredibly angry. He was tired with Shawn's insolence and was ready to teach the young man his righ...

First Punishment

by kinkfiction on Jan 16, 2019
Gay Male

"You disappointed me, baby boy. I know you didn't mean to, and I'll forgive you. But first I need to show you the true extent of my unhappiness. You've been such a good boy up till now but I can't let you think that you can get away with this behavior. You disobeyed me when you went against my instructions. I get that you don't understand why it's such a big...

A Very Special School

by JASONSHOMOEROTICA on Aug 18, 2017
Gay Male

Moulton-Midmarsh Reform School Its Foundation, Rise and Demise An imaginary tale set in the early twentieth century By Jason Land ***** Chapter 1 My name is Martin Fairweather. I am professor and head of the History Department at the Fenwide University, one of those institutes of higher learning created in that push by the governments in the 1980s an...

Naughty Boy

by fantaseeboy on Sep 1, 2017
Gay Male

Not only did my mother have to accept the fact that her only son was gay, that was hard enough in itself! She'd always dreamed of having grandchildren and now that would never happen. No, in addition to that, my mother had to accept the fact that I'd fallen totally, head-over-heels in love with a man nearly her age! The first few times she met Sam, she looke...

The Ingram-Lewis Chronicles Pt. 02

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PATRICK INGRAM-LEWIS - OLIVER'S FATHER A Homoerotic Short Story By Jason Land FOREWORD Subsequent to publishing the first story in the chronicles of the Ingram-Lewis family, the present Headmaster of Rigby School, having read the first account, kindly gave me access to documents from the school archives which throw a somewhat different light on the scho...

The Ingram-Lewis Chronicles Pt. 06

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PART 6 - PATRICK'S FINAL TERM AT RIGBY ***** CHAPTER 1 Patrick Ingram-Lewis, the Head Boy had just returned to Rigby School after the Easter holidays. It was the last time he would be returning to the school at which he had been a pupil since the age of thirteen. At the end of this, his final term, he would be leaving the place for ever to start the next...

Shawn's Punishment

by Guy521 on May 15, 2019
Gay Male

Shawn stood in fear as his master examined his body. Master had shown up unannounced at his dorm room for an impromptu inspection of his boy. They didn't see each other much anymore, as both their lives had become so incredibly busy but Master would always show up at some point to keep Shawn in check. Master ran his calloused fingers over Shawn's rippling ab...

The Harrington School for Boys Ch. 03

by AgentK on Nov 27, 2017
Gay Male

It was around midnight on a Thursday night, and Graham Ainsley was sleeping soundly when suddenly he was startled awake by his bedroom door opening and a light turning on. He looked up to see the prefect, Reed Burgess, dragging his roommate Aidan by the arm. Aidan appeared to have been crying. Reed pushed him roughly towards the bed, giving him a scornful lo...

Spanking Mode with Danny

by alexcarr on Aug 18, 2017
Gay Male

Peter says:- I adore being spanked if it is especially giving pleasure to my spankee. It stings of course but there is a certain divisor when the hurt can be made pleasurable when you have an experienced spankee like I do in Sir. His real name is Danny but that is how I must address him when he sessions me. And when the hurt becomes intense, a little strok...