Gay Rubber Sissy Stories

2,274 results
Orientation
Length
Source
Infinite Scroll

My Time in the Monastery

by brownmonkk on Aug 18, 2017
Gay Male

Brother / Sister/Slave, ("TML") November 1970 "Good loving & Good Scourging" The story of a MASTER and his slave! WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I always imagined having my "first time" with a sexy gal, but nonetheless my first sex was great! I often fantasize and...

PIXIE Sissy Stripper Ch. 02

by EROTICbearscribe on Dec 24, 2019
Gay Male

Sunlight played peekaboo through the blinds and woke Benji from the best sleep he'd ever known. He opened his eyes and breathed deeply. His eyes adjusted to the bright light and he looked around the strange bedroom he found himself in. He noticed a fuzzy pink sweater draped over the back of a chair in the corner of the room. There was also a pair of yello...

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

You are a Sissy Pt. 08: Future

by Roland15Rollin on Dec 30, 2019
Gay Male

Hello, sissy. Well, we have come to the end of our journey together, princess. We have explored every corner of your gay sissy mind and now we have come to the end. And what a journey that was. We learned so much, sissy. We learned about who and what you are. We learned about what you want. We learned about what you need. And we finally got rid of all of...

House Rules Ch. 05

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Nine BEYOND THE PINK DOOR For the next hour I explored the sissy wonderland which Daddy had created just for me. It was a bedroom fit for a sissy princess. I guess that was me now, Kitten, Daddy's sissy princess. There was a closet of pretty clothes and shoes. The large dressers were full of so many girly things my head was spinning. There was a...

Sissy Cuckold & The Old Bull Ch. 02

by DirtyDaddyHunter on Sep 19, 2017
Gay Male

"Now for your turn" leers the old bull, stroking the mushroomed head of his gnarled old cock. The old man starts to get hard again and grabs the husband's head. He slams his cock back in the husband's mouth, brutally facefucking him. "Is that what you want Sissy? To be Daddies pantied cocksucker? "The husband chokes and gags on this vile old man's big cock,...

Steve's First Gay Sex Ch. 01

by stevemike08066 on Dec 12, 2018
Gay Male

My name is Steve, and I recently turned homosexual, and I now serve a very tough, but fair Master who loves and let's me cum as much as needed. This is the story of how I was not only turned gay, but also submissive. I was having dinner with my girlfriend one night, and we're about to leave when I had to use the men's room. Now to describe myself, I'm 5'...

The Hanky Code Pt. 14

by His_fag_wife on Sep 14, 2017
Gay Male

The warmth of the sun hit me after such a long time in the dark and dirty recesses of Master S's world. The fact I was wearing heavy duty rubber panties and bra became all too apparent as I started to perspire, not that I could take my hoodie off in the area I was about to walk through and with what I was wearing under my shirt. I started to walk on my sti...

30-Days of House Arrest Ch. 02

by bjmichaels on Dec 4, 2017
Gay Male

It was hard to concentrate on washing the breakfast dishes and cleaning the kitchen. Mister G was in one of his playful moods and couldn't seem to keep his hands off me. He massaged my shoulders and back and occasionally a hand would slip beneath the waistband of my shorts and claim possession of a buttock, squeezing and pinching it. Needless to say, I wou...

Sissy Bottom Has a Nite Out Ch. 04

by lostsoul1974 on Sep 14, 2017
Gay Male

Well, following some completely depraved sexual exploits last weekend, I entered the workweek thoroughly satisfied! For those of you not following the series, (see my cocktales) my fuck buddy Eric and I had some really hot gay action at a local Theater, as well as a raunchy, fem-dom 3-some with my wife Toni at home where she showed me all over again why I...