Gay Sissy Boy Stories

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Orientation
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Infinite Scroll

College Fund Ch. 07

by bjmichaels on Sep 14, 2017
Gay Male

"I want to be naked with you," I whined to Marty, "is there any night we can be together? Maybe spend the night in a motel?" I already knew the answer. His wife, Miriam, told me she will intentionally be out of town Friday night so I could lure her husband to the motel. It was simply a matter of Marty working up enough nerve to meet me in public instead of...

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...

Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...

The Boifriend Ch. 02

by AdmiralSquish on Jun 19, 2019
Gay Male

[pre-story]This story's not dead! I was a little stuck trying to figure out what to work on, and I got some comments recently asking for more M/M stuff, and then I got inspired and now here we are. Convenient that the first story to go public in pride month is M/M. Content Warnings: M/M, femboy, sissy, potentially offensive dirty talk Disclaimer: All chara...

Panties, Panties, Panties

by bjmichaels on Apr 3, 2019
Gay Male

Don't Call Me Pantyboy I couldn't believe my ears. I shouted at my roommate: "What are you saying? Are you accusing me of wearing women's panties? Are you saying I LIKE wearing women's panties? I wear MEN'S briefs -- and they're COTTON!!" He smirks and says, "You know, John, teenage girls wear red cotton panties too!" I am apoplectic. My face as red as...

Analyzed From The Bottom Up

by Cumfusion on Sep 14, 2017
Gay Male

We were losing power yet again and Jock was getting angry. His eyes were fiery and with his big arms stained with oil and diesel fuel he might have looked really threatening to anyone else. I hadn't had much time to get to know him. He was like you could say 'a good solid looking trucker'. I suppose, if I am to be perfectly honest, I had noticed his physique...

A Night at the Club

by keptsissy on Sep 16, 2017
Gay Male

"Did you make a mess in your panties? Let me see." I stand in front of him. He's seated at a table in the back of the bar. He smiles, a dirty ogle more accurately, toward the man seated to his right. He looks back at me, sees my nervous reaction. He shakes his head with a somewhat disgusted look on his face. He reaches out and takes the front of my short sh...

Hallowiener Pt. 03

by forummj on Jun 18, 2018
Gay Male

I yanked my cap down tightly and bowed my head. Hunching my shoulders forward I pulled my rucksack tight to my back and made a dart for the front doors. All my fellow students made their lazy way to class as the bell rang. I felt like they all knew what had happened last night, and I didn't just mean the party. I was nervous, almost scared that they knew. "I...

Tame Cocksucker

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. The idea for this story was suggested by donaldelliott11, with thanks. ***** "With this ring, I thee wed," Angelica said. With this yoke, I thee burden, Artie's mind echoed, just one moment forgetting the perks that came with marrying this fat, moody cow. Everything had moved so fast. Artie had the good fortune of working f...

The Birth of a Sissy Pt. 03

by sissymedic1426 on Sep 14, 2017
Gay Male

By my sophomore year of college I had performed well enough in the class room that I had earned a few scholarships. This meant that my folks were saving money while I was getting my learn on. It also meant that my dad had promised me that if I rode it out for one more year in the dorms that by my junior year I could move off campus. The thought of finally ha...