Gay Anal Punishment Stories

4,517 results
Orientation
Length
Source
Infinite Scroll

Naked Scott Ch. 05

by tattoo_dragon on May 12, 2020
Gay Male

Writer's note: this scenario contains extreme dominance and submission as well as master/slave role play. Just a heads up in case that is not your cup of tea. *** At eleven o'clock on Friday night, there was a knock at my door. My body jumped to attention. My cock started getting hard as I went to let him in. My hand was trembling slightly as I raised it...

Topless

by naughtygaywriter on Jan 16, 2019
Gay Male

I couldn't believe my luck. Against my better judgement, I went on a blind date. I was glad I did. He's smart, witty, sweet and fun. He's not bad to look at either. I'd have to thank Karen at work for introducing us. I had my reservations about meeting Philip, almost cancelling the date at the last minute. Since it had been awhile, and I was tired of spendin...

Cock-Sucker: Weekend Ch. 02

by tristantrotsky on Apr 3, 2019
Gay Male

Bearing No Relationship To The Jean-Luc Godard Film Of The Same Name... When we arrive at the Chateau, it takes my breath away. It's an amazing place of turrets and ivy-framed balconies, set in its own private grounds, like something from an exotic tourist brochure. Once there, Paul and I spend most of the time naked, obviously because that's the required...

A New Broom Sweeps Clean

by JASONSHOMOEROTICA on Aug 17, 2017
Gay Male

A Homoerotic Story By Jason Land FOREWORD This story covers a two year period in the life of one, Dr. Andrew Waterlow, a brilliant Oxford classist who turns to school teaching as a profession, but who who is finally appointed, aged only thirty, to a research professorship at the University of Oxford. Depending on context, he is variously referred to in t...

Winners and Losers Ch. 11

by bawdybloke on Sep 15, 2017
Gay Male

"What?" My trembling hand wiped my feverish brow. "I think I'm bisexual," I blurted out as she held me tightly. "I ..." "Love, tell me something I don't know!" "What! You knew?" My voice incredulous; hers flippant. "I sort of knew all along." Her fingers wrapped themselves around my hand and stroked it gently. "Been waiting for you to realise." "What?"...

Steve and Kyle

by JASONSHOMOEROTICA on Sep 5, 2018
Gay Male

CHAPTER 1 Kyle Sinclair, the main character -- let us call him the hero -- of this story, is a Chicagoan; active, young, muscular, sexually superbly equipped and totally gay. Kyle comes from a working class family living in the western suburbs of the city and has never paid much attention to learning anything at school, which, when he was eighteen he left r...

Jeff's Dirty Arcade Adventures Ch. 02

by occurious on Jun 1, 2020
Gay Male

This is a continuation of my first story, you don't have to read that one to enjoy this one but I encourage you to do so. * Driving home from the arcade I was praying that nobody would be home, I really looked worked over and even though I'm sure it was my imagination I could swear I smelled the cum leaking from my ass. Thankfully my prayers were answered...

The Lock Ch. 08: GAY

by theMasterBaiter on Apr 9, 2019
Gay Male

TRIGGER WARNINGS: Simulated Rape, Pain (1 drop blood), Male Bi/Gay, MaleDom, FemDom, Family (no incest), Consensual Non-Consent, and Sex Work (idealized) The only coercion is from a sense of duty to family. All over 18. Credits: Edited by the 'Erotic Confectioners. Many thanks to Onyx03, and Jasmine27 as well as others for editing this story. Note: Nine c...

The Toyboy Experiment Ch. 02

by cupbearer on Sep 19, 2017
Gay Male

TUESDAY We had lunch on his balcony, the two of us sitting there in shorts and shirts like a father and son on holiday. Then after we'd had a read and a brief snooze in the afternoon heat, he woke me by tapping me on my knee. I opened my eyes and he was leaning over me in his shorts, bare-chested, smiling. "Let's start," he said. I smiled back, nervous,...

Bootcamp Pt. 01: Initiation

by sexdonuts on Aug 8, 2018
Gay Male

I've always tried to look confident, self assured, masculine, and in charge but internally I've had a desire to submit for years. It all started when I was twenty, in college, and curious, and discovered kink. I remember finding a video of a man suspended by ropes and being tormented by a room of horny houseguests, and wishing I could be in his position. To...