Gay Sissy Cheerleader Stories

955 results
Orientation
Length
Source
Infinite Scroll

Taliban Concubine Ch. 03

by bjmichaels on Sep 14, 2017
Gay Male

My mouth was filled with warm, throbbing cock-flesh, but my gaze was trained on Sparkle-Eyes. I wasn't staring at him really; it was more surreptitious glances now and again. He was sitting a few feet away watching me suck his men's cocks with a bemused expression on his face, a wistful look in his eyes. That he was going to miss me when he handed me over...

Daddy Blue Pt. 01

by Ford2020 on Sep 14, 2017
Gay Male

When Charlie awoke that sunny day, he was feeling pretty good. He had no idea life was about to throw him the biggest curve ball anyone could imagine. The following is my first attempt at a multi-part story, and I hope that if you get through it or the following two parts, you will consider leaving me some feedback letting me know what you think. All comment...

Of All the Little Coffee Shops. . .

by EventualRain on Oct 3, 2018
Gay Male

'No , no, no,' I thought frantically 'Not today, not today of all days'. He was here, my french vanilla dream man. In all his gorgeous glory, he was here. And I was a mess, a literal hot mess. It was the hottest day of summer so far and the air conditioner had blown ten minutes after I arrived to start my shift at the coffee shop I co-owned with my best frie...

Field of Blooms: The Beginning Ch. 04

by CE300 on May 16, 2018
Gay Male

The moment you've all been waiting for, Chapter 4 of Field of Blooms: Walking the Halls. As always my stories are gay themed and contain gay sex, except this chapter. Yes, I know you all are crush that there isn't any sex in this chapter. This is a building block chapter that really helps develop the story, don't worry I will make up for the lack of sex in t...

My Fantasies Ch. 07

by bjmichaels on Apr 3, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** I'll Do You If You Do Me "Ohhhh Billy, this is...ohhh God...so wrong...we shouldn't be doing this..." I groaned. His hand moved faster and harder up-and-down my throbbing erection, and, yes...I did the same for him. I don't know what's wrong with me -- I'd never done...

Breaking The Arrangement

by Web Dazell on Sep 17, 2017
Gay Male

My name is Web Dazell and there's a little history to go with this story. I began writing The Arrangement/Breaking the Arrangement back in 2002, posting each chapter on the ASSTR and Nifty websites as they were completed. What is posted below are all of the completed chapters of both stories combined into one. Other than combining the completed chapters, th...

Teaming Up to Turn Them Out

by vikkihawe000 on Oct 8, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sexual situations. * After Kelly graduated from college, she desperately wanted to move to the city, but her mother was hesitant to send her only child to the big city even if she was 23. However, she finally relented after Kelly suggested she live with her Uncle Rod and his long term...

The Slave and His Master Ch. 11

by loveandlust28 on Jan 20, 2020
Gay Male

Hello My Beautiful Readers! This will be the final chapter of my little story, but don't you worry. I will be writing a little epilogue for our favorite couple that takes place seven years into the future. I sincerely hope everyone enjoyed "The Slave and His Master" as much as I enjoyed writing it! Please let me know in the comments if you would like me to...

Descent

by EroticMonster on Aug 18, 2017
Gay Male

The sequel to Contraction. ***** "Your future is with me now." With those six words I became Cody's boyfriend and he became my saviour. Jenny and I were over. Two years of an incredible sexual journey had ended with threats and recrimination. I had been thrown out of the house I had shared with her for almost the entire relationship, and a cloud of humil...

Falling for Matt

by icyblue on Sep 14, 2017
Gay Male

Normally I'd wake up regretfully, instantly turning over and trying to get back to sleep. Not today though. Today I was out of bed and on my feet practically before I had my eyes fully open. I felt giddy with excitement and could hardly wait for the day to get started. After a quick stretch and a glance out the window to make sure the weather suited my mood,...