Gay Chastity Milking Stories

1,806 results
Orientation
Length
Source
Infinite Scroll

Pandora Ch. 01

by Carizabeth on Sep 14, 2017
Gay Male

A few words of explanation to start off with. This story was originally written as a serial on my blog, and I've compressed about a quarter of it into this first installment. The nice part of that? No hideously long waits for the next part! It's the least I can do. The story itself is a spinoff of a previous story of mine posted on Literotica, entitled Bond...

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...

Danny Darling Ch. 05

by bjmichaels on Sep 14, 2017
Gay Male

"UNBUTTON YOUR SHIRT AND OPEN YOUR SLACKS, YOU LITTLE WORM!!" she screamed in my ear. I stood there stunned; frozen in place. I couldn't believe the abrupt change in Mrs. Nelson's demeanor. The normally sweet, good-natured woman had never made even the slightest derogatory comment to me, and she certainly never raised her voice when she reprimanded me for...

Opposites Attract

by Pelaam on Nov 12, 2019
Gay Male

I walk indolently towards my new temporary workplace. I do not *have* to work, but I am good at what I do and so I take on the occasional placement; this one in a large software company. I will be one of their internal IT specialists. The company has Sales, Finance, Customer Service, HR; a full complement of areas where a faulty PC could cause big problems....

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...

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...

Jocks of the South Pt. 10

by scottgoulding123 on Sep 14, 2017
Gay Male

Sorry for the major delay in this chapter! It was a difficult one to write and it ended up being much longer than I originally intended. Thank you to everyone for their patience and I hope you enjoy reading it! :) *** Easter Sunday Nick's week in California had been hell. He had to stay in his brother's apartment (which was old and gross), he'd gone witho...

Journey in Love

by bhart1 on Jul 24, 2018
Gay Male

Author's note: If you came here for a quick read then this is likely not your cup of tea. Sincere thanks to my friend and fellow author BaccusDelectous for his keen proofreading skills and valuable guidance in geographical/cultural accuracy. ***** According to my parents, they met at university in San Francisco and fell in love at first sight in 1982. Feel...

The Daughter's Boyfriend Pt. 04

by rimaday on Oct 8, 2019
Gay Male

Note to the reader: This story contains depictions of non-consent and reluctance as the lead character discovers his inner most desires. ***** I woke to the feel of Jackie's warm breath on my chest as she nestled into my shoulder. Her leg was draped across my pelvis. I was completely content and sexually drained. Her soft warm skin felt like heaven and I...

Stand for Love Ch. 14

by vanalas on Oct 2, 2017
Gay Male

Welcome to the 14th chapter of this story. I appreciate your time and your great love. I really hope this chapter will be interesting to you. Don't forget to drop your comments and rates at the end of this chapter. Happy reading... **** Adrian slowly opened the door leading to his room. He stood in the door way, his face looking straight but he couldn't se...