Gay Chastity Anal Stories

3,674 results
Orientation
Length
Source
Infinite Scroll

Enslaved by Myself Ch. 03

by Lausunaht on Sep 14, 2020
Gay Male

I was dreading what was about to happen. My master was going to hurt me badly to ensure I would never rebel. I knew this for certain because I would do exactly the same if the roles were reversed. I could only hope that my affection for myself was strong enough to limit the pain. He left me tied up alone for hours, I was thirsty as I didn't drink the whole n...

Eager Boy

by TwistedPanties on Mar 2, 2020
Gay Male

The ping on his phone startled him. "Text when here." He sat nervously in the back of his Uber, en route to meeting a new Dom for the first time. He had been daydreaming about their online conversations online that had started about three weeks prior. He recounted the naughty and perverted things he had shared, and his limits he had discussed, and even ha...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

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...

Temporarily Dickless

by AssWhisperer on Sep 14, 2017
Gay Male

[Warning: This is a very sexually dark story. Fisting, watersports, medplay, implied body modification, chastity. My thanks to Kenji De Sade for his encouraging me to write this story after a series of conversations about chastity.] How had I come to be here? I wondered as I floated in orgasmic bliss. It had started with my impulsively writing a guy on...

A Night at the Movie turned me Gay Pt. 02

by jamtby on Oct 12, 2020
Gay Male

Entering the room immediately caused my stomach to churn with excitement. Something about entering a place where strangers are in control and you anticipate being involved with sexual activities. The what, why, and how remained a mystery. This only added to the combination of nervousness and excitement. The woman with a strangely deep voice said, "Welcome...

Power Trip Ch. 05

by Wally_West on Sep 26, 2017
Gay Male

Colin stood in front of the toilet relieving himself through the opening at the tip of his chastity cage. He was growing used to its weight and presence, finding less discomfort from the device every day. He was happy it was Saturday and he didn't have to go to school; Colin wondered what his step-mother had in store for him, as their sexual activities were...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

Open in Reader

Guys' Retreat Pt. 01

by Cyanlot on Jan 20, 2020
Gay Male

Part 1: Going Away with the Guys "No!" Nicole was adamant. "You're not going, and that's final!" "But I have to," I said, trying not to sound like a whining teenager—or, worse, an impotent wimp. "We've been doing this every year since we were in college." "And what happened last year?! ..." She just let that hang in the air and I didn't really have a go...