Gay Sissy Pussy Stories

5,146 results
Orientation
Length
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Full Sissy

by Nils Huim on Dec 24, 2017
Gay Male

Darren couldn't believe his luck. Couldn't believe this was his wife Joy's birthday present to him. It was by far the best—the most exotic and erotic anyway—he'd ever received, in 35 disappointing years. He thought about this as his self-announced "date" rolled a condom down his beautiful cock, and again, moments later, when he was penetrated by it. Darren...

Little Sex Toy Ch. 01

by keptsissy on Sep 26, 2017
Gay Male

Rough sex with a big strong man is something I'd always fantasized about. Ever since I can remember masturbating I'd think about being made to do things, dirty things for a man. I thought about being spanked, made to perform for a man, one that wasn't mean but very dominant, somewhat cruel and unusual but not terrifying. I had the fantasy in my head often....

It Could Be Worse Ch. 07

by eviltwin52 on Sep 14, 2017
Gay Male

We've been in service to blacks for 6 months now. Mom, my wife Cindy, and I have completely devoted ourselves to the pleasures of the Superior African race and Leon. The club where Leon has us working is a nice dinner club on the waterfront in S.W. Washington, DC. We work as greeters and servers with a few other white couples and single white women. All of...

Cocklust

by TerriC on Oct 6, 2020
Gay Male

I was horny the moment I woke up. My cock was hard as I showered and got ready for work. I slipped into a pair of blue nylon panties, something I usually only did on the weekend, and finished dressing for work. The drive in was crappy, traffic sucked, but it wasn't so bad while in my panties. Wearing them may have been a mistake though, I was semi hard when...

Discovering My Slut-Side Pt. 02

by i_like_it_like_that on Dec 10, 2018
Gay Male

With Danielle's fingers and mouth off my ass, I knew what was coming. Not being able to cum made me incredibly horny. I was ready for release and wanted Andrew's cock inside of my warm hole. I stared at his dick with a look of lust and got lost of the moment. I was brought back to reality by Andrew slapping my face with his veiny shaft. "You ready for this...

Gay Cave Escape

by Hypnodip on Mar 11, 2021
Gay

Drip! Drop! Drip! A staccato of water droplets add to a quiet and dark ambience. A nearby rock is dislodged, crashing with a large boom. You awake with a jump, chilled from the rock floor you were sprawled on. The room you're in is almost too dark to be traversed. You can see three ragged walls surrounding you, sprawling upward out of your limited night visi...

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Jail Time Ch. 02

by oralguy82 on Aug 18, 2017
Gay Male

Before, I had spent 2 weeks in the county jail and, I thought that was all done and gone, and would be forgotten. But about 4 months later, I was almost thinking how can I sign up for another 2 weeks. I felt humiliated about the experience, but so turned on too. More than once I had jerked off to the memory of that humiliation. A 25-year-old man thinking ab...

Simple Submission

by LoveIsUniversal on Apr 10, 2018
Gay Male

Heidi had a good life here in Southern California. At the age of forty-three, she had a good job and a lovely house. Living in the city of Arcadia was almost the equivalent of an island paradise. She had friendly neighbors who reminded her why she stayed in such a quiet and clean suburban community. They were good people, the kind that never overstayed their...

Rest Stop Management Pt. 04

by rimaday on Jun 3, 2019
Gay Male

Author's note: This story contains scenes of non-consensual or reluctant sex. I awoke to Big Daddy easing out the door and looked at the clock. It was just past midnight. I lay awake for a couple hours reliving the past few days, trying to figure out what it all meant. My marriage would never survive if my secrets got out. So much to lose and my mind kept...

House Rules Ch. 04

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Seven PRETTY PINK BOTTOMS The first step on my trip down that path happened one hot Sunday afternoon. I had just come out of my bedroom after spending a few hours in the pool. I was wearing a pair of loose fitting boxer shorts which hung low on my butt. I was drying my hair with a towel. Mr. Clemons was there to meet me in the hallway with that...