Gay Chastity Sissy Stories

970 results
Orientation
Length
Source
Infinite Scroll

The Duplex Ch. 01

by TheCandyManCan13 on Sep 1, 2017
Gay Male

Chapter 1 - An Unexpected First My wife Eleanor and I (Peter) had been married for four years when the events I am about to describe to you took place. We were 25 years old and still madly in love, but we had started talking about expanding our sexual lifestyle outside of our own bedroom. I am of largely European descent, brown hair, 6'2 (1.89 meters) and 1...

A Matter Of Size Ch. 03

by quipogo on Sep 14, 2017
Gay Male

Hi, This is the third part of my story A matter of Size. I included a Prologue in which I summarize what happened in the other two chapters, so if you do not remember or simply you do not want to read those parts, you still will be able to follow the story. I hope you like it, thank you very much for reading it. ***** Prologue I kept telling myself, "how...

Exploring my Sexuality Ch. 03

by alexis19901 on Jul 6, 2020
Gay Male

I could have put this story in a number of categories but it consists a lot of gay sex so that's why I've picked it. It does contain some elements of taboo, group sex, crossdressing and gay sex. The other chapters do provide some of the back story. After my last meeting with Mark, I went back to my normal life. Going to work, college and seeing my girlfrie...

To Have a Sweetheart - David Ch. 02

by kaitslou on Sep 14, 2020
Gay Male

I woke up alone once again, but I guessed that it'd probably start being like that, an early bird and a night owl as we were, trying to accommodate the others habits. Rolling around in the bed I noticed Luke had folded up my clothes nicely from the pile I left them in, I was going to wear them anyway, what's the point? Oh well, what ever rocked his boat......

Floating World Bitten Peach Ch. 06

by KeithD on Dec 10, 2019
Gay Male

Deng Qiao, owner of all of the cotton mills within sight of Langshan Mountain—Wolf Hill—at the fringe of the Yangtze riverside town of Nantung, sighed as he wiggled his hips into the pillows and held his young consort's silken black-haired head in his lap. Ping, the singer musician, who Qiao had bought from the Cut Sleeve Nanleshijia—men's pleasure house—was...

The Paint Job Pt. 01

by Robert_Furlong on Nov 27, 2017
Gay Male

With the current fashion for newlyweds to have their wedding night nuptials committed to canvas, I have become familiar with sketching hesitant couples alongside their conjugal beds. Painting such tender moments presents a fascinating artistic challenge and I've developed a reputation for capturing the mood of the marital suite with discretion and sensitivit...

The Jackal House

by castlequill on Aug 30, 2017
Gay Male

When I was 18 years old, I was kidnapped. Except, it wasn't your typical kidnapping. There was no ransom call, no revenge plot, nothing. Nothing except a couple of seriously fucked up, twisted minds of some seriously fucked up, twisted psychopaths. It was the summer after I graduated high school. My best friend Lacy and I embarked on a 2 month backpacking...

Idolatria Ch. 05

by Asbel on Nov 18, 2019
Gay Male

Tannery. A place where animal hides are tanned; the workshop of a tanner. That didn't help. Tanning. The art or process by which a hide is tanned; a sound spanking. What? An article - Tanning (Leather) Spanking and leather. I felt like everything I found out about Levi just complicated things and made him harder to understand. I was waist-deep in rese...

A Tale of Two Cousins

by fantasyhunter2 on Aug 18, 2017
Gay Male

Authors Note: This story includes descriptions of both homosexual and heterosexual liaisons between first cousins. If you find either gay male sex or incest objectionable you should try another story. * It was March and I was on top of the world. I was in my second year of college and had finally adjusted to life outside the cocoon of growing up protected...

Salvation

by EroticMonster on Aug 18, 2017
Gay Male

I swallowed the warm sticky spunk and held onto Hassan's cock until it was flaccid. He sighed several times and remained motionless with his eyes closed. With gentle motions I rolled the softening meat around my mouth. Every so often his thigh twitched. "That was amazing." He whispered at last. I hummed into his groin. "I can't believe I let you do it again...