Gay Sissy Chastity Stories

970 results
Orientation
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Infinite Scroll

Progression Ch. 14: Befriended

by klapperz on Jul 3, 2018
Gay Male

Nathan woke up earlier than usual the next morning after a night of arousing dreams. He was eager to start work and see what the guys had in store for him. After his daily inspection with Kevin, they both made their way to Ryan and Jacks house. Once they arrived, Nathan stripped and made his way to the basement to begin his daily show. When he reached the...

Masturbate Fantasy #131

by writedoctor on Sep 14, 2017
Gay Male

Journal Entry January 21st Traveling through southern New Mexico. Mid 60's. Warm enough. Staying at a campground in a rustic log cabin. No frills. I like that. Decent Mexican food nearby. Community laundry and very sanitary facilities. Long hot shower sounds good. Wishing for a surprise guest. I confess journal, I have thought about him. Closing eyes. Rand...

Submitting To My Roommate... Ch. 02

by chriscili on Aug 18, 2017
Gay Male

The next morning I woke up and got out of bed. Chris had already gone to the shower so I went to my mirror to see what I looked like. I really shouldn’t have been surprised when I saw that my face was covered with dried cum. I grabbed my shower towel off a hook on the back of our door, used it to dry rub the cum off my cheeks and lips and then wrapped...

The Voice

by AltErik on Aug 18, 2017
Gay Male

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains explicit sexual and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself and locations I kn...

Nephew's Readjustment

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Cynthia's life had improved drastically in the past two years. Most people would consider getting a divorce at thirty years old pretty bad. A divorce due t...

The Chaste Boy and the Locksmith

by fantaseeboy on Oct 31, 2018
Gay Male

A little bell tinkled softly as the door closed behind me. A shiver shot up my spine as I stood there in that little shop waiting to be helped. For a brief moment, I thought about running out the door and living with my current predicament. Just as I was about to act on that impulse, an older man stepped from behind a curtain. He looked to be older than my f...

Progression Ch. 06: Confession

by klapperz on Mar 27, 2018
Gay Male

When Nathan arrived home and entered through the front door, he instantly heard Jeff shout out from the living room "So the lucky boy returns?" Nathan walked into the living room to join Jeff who was sat with Kevin who was playing on his phone. "So who was he? Anyone we know?" asked Kevin who glanced up from his phone. "What, I've stayed out all night bef...

LoveLocked: WokeWired

by adamlily1972 on Dec 9, 2017
Gay Male

Dear reader: A political satire of "woke" white people, particularly woke white women. Definitely not to everyone's taste. Intended to be humorous. Skip if offended by the notion of a white gal mind-controlling her white boyfriend to service a black dude. But quaff heartily if the idea gets you hot. Adam ********* SCENE 1 [Setting: A spacious but d...

Spanked and Buttfucked Asian Male

by asianspankee on Aug 30, 2017
Gay Male

I'm an Asian male, with slim and very smooth naturally hairless body, and average height. The story happened when I was in my twenties. I hope you enjoy reading it... Ever since a teenager I've always had a very strong, repressed desire to get fucked by another man. I think one reason is because my body is quite slender, and extremely smooth devoid of any b...

The Talent Scout

by eviltwin52 on Jun 5, 2019
Gay Male

The day I first met him was like any other day. Riding the Metro to work I was suddenly jostled out of my reverie by some one bumping into me from the back. Turning I found myself looking up at a ruggedly handsome man. His steely grey/blues seemed to pierce into my very being. I wanted to look away but was unable to do so. After a few seconds that seemed to...