Gay Rubber Sissy Stories

2,274 results
Orientation
Length
Source
Infinite Scroll

Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (M+/M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job. In my second...

Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

Princess

by skinnysailor on Mar 2, 2020
Gay Male

I'm Dan. My lover, Rex, calls me 'Princess' as in his little fairy princess. He told me how tonight's date wanted me to dress. Very specific. Three inch strap on spike heels. An ankle length skirt. I chose my dusty blue wool one. A see through blouse. I'm wearing my pink one with the frill collar and cuffs. Panties, no bra. I put a little rouge on my nips....

Fixing the straights

by cdbaby on Dec 28, 2016
Gay

You wake up and prepare for your day, unaware that this would be the last day you would be considered straight. You shower as you did every morning and felt the water's warm touch as it cascaded over your skin. You could stay here forever if you could. But you need to start your day and the hot water would run out before long. You wash your hair, then the re...

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The Talent Scout

by eviltwin52 on Jun 5, 2019
Gay Male

The day I first met him was like any other day. Riding the Metro to work I was suddenly jostled out of my reverie by some one bumping into me from the back. Turning I found myself looking up at a ruggedly handsome man. His steely grey/blues seemed to pierce into my very being. I wanted to look away but was unable to do so. After a few seconds that seemed to...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

The Hanky Code Pt. 13

by His_fag_wife on Sep 14, 2017
Gay Male

His cock was back up to its huge level, it was all encompassing and felt as though it was running through my entire body a second spine for my body. He stood up and I expected more of the slamming squats, but it seemed Master S liked a varied gym session. His massive hands cupped my widely spread ass cheeks pulling them apart still further. He then did sho...

The Stranger

by WatchingAndWaiting on Aug 18, 2017
Gay Male

!29f_UseMyBf - I want you to slap him around good. don't hold back. make him cry. and don't let him cum, okay? it's all selfish. all about you. okay? hungBristol24 - yea - where is he? does he have flatmates or anything? !29f_UseMyBf - He's staying alone. The address is no. XX Graining Pl, BSXX XXJD. Just knock loudly, and when he asks who it is, say you'r...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...