Gay Shemale Chastity Stories

340 results
Orientation
Length
Source
Infinite Scroll

Human Blowjob Machine

by Subkoksukr4u on Jul 17, 2019
Gay Male

"How many cocks you sucked off before this one?" she asked. Like I could talk right now. "Mmmmmmphhhh", I managed between gagging. "I betcha lost count long time ago, huh?" She laughed, knowing full well I had. Lisa had turned me into a human blowjob fucking machine. I was literally strapped down, head in a harness with a rod attached to a variable speed...

Deliver a Virgin

by sr71plt on Sep 14, 2017
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sexual situations. Most of the mounted escort riders gathered around their leader were watching the small band of infidels, led by Hugh d'Ibelin, as they rode out of the gate of the stronghold of Belvoir and moved to meet the forces of the Saracens and their allies on the hilltop overl...

Progression Ch. 05: Overnight

by klapperz on Mar 27, 2018
Gay Male

Nathan got showered, making sure to use his syringe only two times. He dried himself off and got changed into his leather locking pants. He put on some tracksuit pants and a t-shirt, before heading out the door almost running to Ryan and Jacks. Finally, he was standing outside their house knocking on the door. "Well aren't you eager?" said Ryan. Maybe it w...

Adam & Steve, Not Eve

by SEVERUSMAX on Sep 14, 2017
Gay Male

Eve Winters, known to her slaves and the BDSM community, as "Mistress Eve", was quite pleased with her success in controlling her slaves so far. She was especially satisfied with the power that she had over Adam, her husband. She married him to get legal title to half of his estate, which has considerable. She frequently fucked other men, and only allowed A...

Business Trip

by Diego99 on Jul 16, 2019
Gay Male

This is a true story of my 1st experience with another man while away on a business trip. Names only have been changed for privacy... *** I'm 32 years old married with kids and have been straight all my life - up to now. My curiosity about experiencing with other men started years ago because of watching porn. I was initially into lesbian porn, then threes...

Curiosity Brings a New Experience

by toddd0134 on Sep 15, 2017
Gay Male

This is the actual story of my first gay experience. The names have been changed, but everything else is as it happened. I hope you enjoy! ***** All my life, I'd always considered myself straight. Lots of girlfriends, lots of complements on my looks and plenty of opportunity to get naked with the "fairer" sex. Also, a healthy appetite for porn. It was pr...

Finding Out I Love Cock

by 54btmguy on Sep 14, 2017
Gay Male

This is my first story of how I learned I love cock and cum and how much of a slut I like being so although will be somewhat short but hope you enjoy it. ***** I was just out of the service and at 32 my divorce was finalized and I moved back to my hometown and enjoying my new freedom but even though I was out having a good time a couple nights a week I was...

Amazing

by Suavebollo on Jul 15, 2020
Gay Male

At 50, I was still lost as to who and what type of person I was. Being married most of my adult life, I was scared and hesitant to come out of the closet. No one and I mean no one would ever suspect me of being bi or gay, but here I was again, walking into Amazing Lingerie in Dallas. I used to visit bookstores to get my cock sucked, but sometime in my late...

My Inner Slut Ch. 06

by SlutAlexR on Oct 30, 2018
Gay Male

Daddy had been gone for a few days. He was away on a business trip. We communicated frequently, and he reminded me a few times that he had a surprise for me this coming Friday. So I waited anxiously for the end of the week. On Friday morning, I received a text: "Hello luv. I have been in contact with your Owner. We will pick you up at 6 tonight. But be ready...

Chase Becomes Chaste Ch. 04

by growing_interest on Aug 22, 2017
Gay Male

Chapter 4: Dogged Determination Synopsis: With his powers seemingly exhausted, our narrator recruits help to keep Chase in his place. **************** I awoke with a throbbing headache. I felt hungover. The sun shining in through the room's many windows strained my eyes. As much as I just wanted to stay in bed, eventually I pulled myself up so that I coul...