Gay Sissy Bondage Stories

1,263 results
Orientation
Length
Source
Infinite Scroll

The Coffee Shop Pt. 03

by canadiancowboy on Sep 14, 2017
Gay Male

The Coffee Shop III: The Good, The Bad, And The Hypnotized Disclaimer. The following story, is a work of fiction. The characters portrayed within are a work of fiction as well, and any resemblance to any person, living or dead is a coincidence and unintentional. Copyright 1999. This story is the property of the author, Canadian Cowboy (formerly known as...

Little Jimmy Grows Up

by timmywells on Sep 14, 2017
Gay Male

In the interest of full disclosure I would like to mention that this story involves the following topics; rough, reluctant but consensual sex, anal sex, and both very dominant and completely submissive characters. This story takes place during the Summer of 1970 and involves a very shy, meek and socially awkward guy whose life is forever changed one day in...

Chase N' Justice

by Shy_Bottom69 on Sep 1, 2017
Gay Male

Standard disclaimer: This is a work of fiction. Warning: There are elements of non-consensual sex. The story takes place in Dixon County, South Carolina. Please, don't try to look it up you'll be disappointed, it doesn't exist. If you are desperate, there are enough clues in the story to figure out which county I'm patterning it after. Any similarities with...

The Boy in Makeup

by DavidPatrick on Sep 14, 2017
Gay Male

Chapter One Like the men who made suicide is in my genes. The temptation was too great for my great-grandfather, my grandfather, and my father, having lured all three to the other side. Theories abound as to why. No one knows for sure. I think it's because there was too much dissonance between who they really were and who they pretended to be. We all prete...

Out of Sorts

by hopelessdreamer on Sep 25, 2017
Gay Male

Feeling out of sorts not sure where my mind is tonight but it is not in a peaceful place. Why would it be I'm currently being tortured? Bound to a table with rope means an attempt at escape would be useless. I am useless. At first they asked simple questions: my name, birthday who my parents are? Then the questions got harder and I was punished for every wr...

Escape to Constantinople

by sr71plt on Aug 18, 2017
Gay Male

Chapter One: Kazan to Novorossiysk As soon as he had seen the truck convoy start to pull into the courtyard of the makeshift main building of the Imperial Military Academy, Pyotr dropped the weights he was working with in the exercise yard and loped down the slope and through the grove of trees that bordered one side of the river park on the rise above Kaza...

The Porn Star and the Prostitute

by ladyroxanne21 on Oct 12, 2020
Gay Male

Chapter One Dylan "Alright my lovelies! You know how much I hate to disappoint all my cherished viewers, but I haven't had a weekend off in months! So after I finish up here, you're just going to have to satisfy yourselves with watching my videos until I come back online. Sorry! I'll miss you all as much as you miss me, I promise!" The comments that poppe...

Office Confrontations Ch. 04

by fexcellent452 on Sep 14, 2017
Gay Male

(Finally the wait is over! I apologize for the months of disappointment, but I wanted to make this extra special – and I tend to ramble for pages on end, sorry! - and now I have accomplished that task! OC 4 is here to stay, and I hope it lives up to your expectations! As always, I love comments, questions, and interesting tidbits so express yourself~ Thank y...

Milk Cartons

by tehuti88 on Aug 18, 2017
Gay Male

WHAT I'M *NOT* LOOKING FOR IN COMMENTS/REVIEWS: *Critique/criticism of my writing style-I'm comfortable with my style (wordiness and all), so if you find it not to your liking, you're welome to try out something else. *Publication advice-I'm not trying to get published, so advice on how to make a piece publication worthy is not necessary. *Sarcasm or rude...

Dubious Desire

by thatkiwiguy on Sep 4, 2017
Gay Male

CONTENT WARNING Dubious Desires is a steamy romance containing coarse language and sex scenes that deal with themes of submission, reluctance and objectification. This story is NOT for the faint-hearted, but it is for those who like m/m stories with a taste of love, friendship, eroticism and dubious behavior that skirts the boundaries of right and wrong. *...