Gay White Sissy Stories

10,754 results
Orientation
Length
Source
Infinite Scroll

I Turned Myself Out Ch. 02

by drmweaver705 on Jun 9, 2020
Gay Male

"You worship cock," the sultry woman's voice on the video said. "You desire them in your mouth." I caressed my dick as I watched the latest CEI videos online With the kids away at college and my wife on a girl's long weekend away in distant New York City, it was time to lock the doors, turn off the lights, put the cell on silent mode, grab the lube and get...

Exploring a New Store

by TerriC on Nov 18, 2019
Gay Male

"I don't know how he did it, every day in those white tights." I thought to myself, as I pulled a pair of tights up my legs. The semi opaque white spandex stretched around my hardening cock. How the actor who played Robin, in the '66 Batman tv show, wore those tights without walking around hard all day, I'd never know. A wet spot forming on my tights as I sl...

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

A Very Big Man!

by keptsissy on Aug 30, 2017
Gay Male

Of the men I see regularly he's the biggest. Not just height and weight, his cock is huge, close to 11". And his cock is thicker than any other man I've ever seen. My ex-boyfriend introduced me to him at a party. He told me to go to the bedroom with him and 'be a good girl'. It was one of 'those' parties, all of us girly girl sissies on full display and on t...

Outed and Married

by keptsissy on Sep 26, 2017
Gay Male

He always threatened me with being exposed to my coworkers, to the world as the sissy I am to him. Usually it was part of what I thought was his dirty talk, sex talk. He'd tease me with it. He'd be deep inside of me, slow fucking me, talking dirty into my ear. Or he'd have me restrained and be masturbating me as part of 'my reward', as he called it, and woul...

Masturbate Fantasy #131

by writedoctor on Sep 14, 2017
Gay Male

Journal Entry January 21st Traveling through southern New Mexico. Mid 60's. Warm enough. Staying at a campground in a rustic log cabin. No frills. I like that. Decent Mexican food nearby. Community laundry and very sanitary facilities. Long hot shower sounds good. Wishing for a surprise guest. I confess journal, I have thought about him. Closing eyes. Rand...

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...

Gay Whore Pt. 02

by Bonemeal on Oct 12, 2017
Gay Male

I stumbled through the door that Ruthy the beautiful black woman had shown me. The music was sultry and sexy, the voices muted as dozens of people milled around in different states of undress. Beautiful women slipped between the crowd and some were roughly being fucked in front of us all. Others were giving blowjobs to the clientele. The room had comfort...

Owned:Fantasy Becomes Reality

by silkstockingslover on Sep 14, 2017
Gay Male

Note 1: This story was written and is dedicated to a true wannabe faggot-cuckold Dave. Note 2: A special thanks goes to Estragon for his copy editing work. 1. THE BEGINNING I blame Literotica. No seriously...if it wasn't for Literotica, none of this would have happened. Now in all fairness, some would argue it is my fault; as it was my own stupidity a...

A Boy, a Daddy and two Tuxedos

by ThomasStevenson on May 21, 2019
Gay Male

"That suit makes u a horny little lad, doesn't it?" It was another text from Mr Matthews. Thomas was out at a bar with his co-workers, and he'd just sent Mr Matthews a picture of what he was wearing: a fine navy pinstripe three piece suit with a bright pink and blue striped tie and a lavish pocket square spilling out of his breast pocket. So Thomas texted...