Gay Chastity Roommate Stories

1,927 results
Orientation
Length
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Infinite Scroll

My Roommate's Toy Box Ch. 03

by brycemanning on Sep 14, 2020
Gay Male

As the hours ticked away that night, I steadily grew more worried that Alex might snap on me and freak out again at any moment. He'd showed me his biggest secrets, touched my dick, and busted twice, all the horniness temporarily drained out of both of us. I anxiously imagined him glancing over, realizing I was still naked, maybe looking down at my dick and r...

Amy Cuckold Brian Ch. 05

by CuckoldGuy on Sep 19, 2017
Gay Male

"Honey, while I was upstairs changing, I went into our bathroom and I saw your douche bag hanging there. Are you having any kind of a problem?" Asked Brian. Setting the dinner table, Amy replied, "No I'm not but let's talk about it later. Will you tell the kids that dinner is ready?" "Sure thing", replied Brian. Later that evening after the children were...

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...

Bobby Ch. 02

by skinnysailor on Jun 5, 2019
Gay Male

It had been several weeks since twenty six year old Bobby came to live with Mommy, Daddy and Kitten. He was fitting into the family. He and Kitten helped the servants. Unless dining with Mommy and Daddy they ate with the servants. Usually he and Kitten chose their own cloths, but today Mommy chose what she wanted them to wear. Kitten wore a long sleeve hig...

Guys' Retreat Pt. 06

by Cyanlot on Sep 14, 2020
Gay Male

Part 6: Brianna, Used and Abused The humiliating show I'd been forced to put on for Kent and Vince with the two dildos had had an effect. I suspected that it had aroused Kent but I was vividly aware of its effect on Vince. His cock was hard even before I'd gotten it in my mouth. When I'd freed it from his pants, it sprang up, eager to fill my mouth. Now, as...

Master Jakob and Seth Ch. 10

by and9993 on Aug 22, 2018
Gay Male

Chapter 10 - Dinner I brushed my teeth and got dressed, then took off my collar and put it in my pocket. It felt strange having clothes on over my plug and cage but I was eager to see where Master would take me. We got in the car and drove to a nearby restaurant. It turns out Master wanted just a night out with the two of us. We got seated and he began by...

Top Becomes a Daddy Bear's Boy Pt. 03

by DaddyBearChaser on Jul 6, 2020
Gay Male

Just as I opened the bathroom door, I heard Mike say, "Boy, make sure you sit down to take a piss. The last thing I need is you making a mess in there" before he began laughing to himself. "Fuck, I have to sit down like a girl to pee. At least Mike won't be watching the humiliating act," I thought to myself as I made my way to the toilet, bladder full of mo...

I Wanna Be Degraded Ch. 03

by 1077ad on Dec 25, 2019
Gay Male

Author's note: After a near-fatal hard-drive incident I was backing up some old files when I came across this. Somewhat to my surprise, this was abandoned in a nearly-finished state and then forgotten about. I mostly just had to spruce it up a little and give it an edit. I'm not sure that at this point, eight years (!) later, there's anyone looking for a con...

College Roommate Ch. 01

by married_but_curious on Sep 1, 2017
Gay Male

Late in the first semester of my freshman year at college, I decided I needed a new dorm roommate. It was almost impossible to study in the rowdy, hard-partying dorm I started out in -- I needed a quieter dorm, and a roommate without an electric guitar and a well-used bong. My Resident Assistant said this would be difficult, since all the dorm rooms in the m...

Another Beach, Another Stranger

by bybiguy on Aug 18, 2017
Gay Male

I was staying in a condo, sharing it with a co-worker during the summer of 1996. He had gone golfing and I wanted to work on my tan. I had brought various bathing suits with me, including several thongs. Thongs, especially on males, were not worn on the main beach, so I put on a gray thong and pulled on a pair of shorts over them. Taking my beach towel and a...