Gay Sissy Boi Stories

901 results
Orientation
Length
Source
Infinite Scroll

Rally Party

by gary_4_u on Aug 18, 2017
Gay Male

This story is a fantasy of what I would like to happen sometime. I hope you enjoy it. It's Saturday afternoon, August 6, 2011. I am in the Mangy Moose Salloon in Hill City, SD enjoying a cold beer after having ridden the 150 miles from my home in WY for the Sturgis Motorcycle Rally. I was waiting for some guys to show up that I had been messaging on Crai...

James Ch. 03: Surprise UPS Throat Fuck

by vanisland1983 on Sep 14, 2017
Gay Male

I would love to hear your input! Contact me through the contact tab on my profile. Chapter 3 of a young man being forced by a stalker. I would warn you about it, but then, that's why you came here to read it you naughty boy... ***** Things have been weird this week. A girl asked me out for a date but I declined. I'm not entirely sure why, she just didn...

Farm Boi Life Ch. 05

by Sungmehetu on Mar 13, 2018
Gay Male

This chapter contains urine ingestion, and torture. Chapter 5 David didn't seem to respond to me walking into the basement. He was in the half sleep that one can sometimes manage while hanging from your wrists. It was chilly in the basement, especially overnight, but sweat beaded his face. Trying to stay on your tiptoes all night would create cramps, but h...

Getting a Taste for Memphis Ch. 02

by hardryder75 on Sep 14, 2017
Gay Male

My summer sexcapade with Marcus continued all the summer long and into the fall. His continued denials of being gay or bi-sexual confounded me. Such statements especially confused me because he made them as I was sucking his cock or while I was getting my ass pounded by him. It finally occurred to me that such statements made him feel better and they confirm...

Judge Ordered Slavery Ch. 05

by Sungmehetu on Sep 26, 2017
Gay Male

Thank you for following Ryan, and thank you to the fans of Ryan. This chapter had two real instances in it. One was a pleasure to write about, the larger one was difficult to write about. Much was added for drama purposes. ***** I quickly figured out what I was in for. I lay on my stomach, my head forced back by a padded bar across my forehead. My arms wer...

First Meeting Ch. 02

by cutewht26mtoplsyou on Sep 14, 2017
Gay Male

*all references to characters, locations and events are fictional. Any similarities between this story and real life are purely coincidental* With my mouth and tongue occupied with your dripping cock, my mind begins to take in the details of my predicament. Here I am on my knees in front of you, my lips spread into a large O by the ring gag fastened around...

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...

Rimming and a Facial

by Dcijames on Sep 2, 2017
Gay Male

For about 10 yrs now, we have been closeted lovers. He was gay, I am closeted bi. I have a girlfriend but occasionally have free time to meet up with him, when both our schedules allow. He is mostly a top, and me a bottom. He is black and I am white. He has a nice 8+ inch cock, which I absolutely love sucking! We have done most of the sexual things two me...

My Neighbor Made Me Do It Ch. 05

by CapnSteelBoy on Sep 14, 2020
Gay Male

My Neighbor Made Me Do It Ch. 5 by: CapnSteelBoy --------------------------------------------------- Chapter 5 This is a continuing series, so starting here won't make a lot of sense. Author recommends starting from the beginning, if you haven't already done so! Waking up sore and tired from the day's activities, my nap was cut short by me trying to rol...

Bitch Boi Pt. 01

by Dreaded654 on Jun 1, 2020
Gay Male

I take a deep breath, barely believing what I'm about to do. The car is still running and I consider leaving, but know that I won't. I came this far. I'm here to stay. I grab the plastic bag in the passenger seat and look at the contents. It's a thin blue thong bathing suit. Not a man's thong (which somehow would make this better), but a bathing suit bottom...