Gay Sissy Cheerleader Stories

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BBC Cheerleader

by Alysonthecorruptedslut on Feb 10, 2020
Gay

// Hello, I'm glad you've taken an interest in my musings, I'll be updating this story as much as I can, but please be patient as I do have a busy personal life on the side. If there's any particular fetishes you'd like to see in her, send me a message and I'll see what sort of magic I can make. ~Alyson \\ You thought long and hard about how you were going t...

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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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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...

The Voice

by AltErik on Aug 18, 2017
Gay Male

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains explicit sexual and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself and locations I kn...

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...

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...

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...

Master Comes on Sunday

by Cap_N_PieSissy on Dec 9, 2019
Gay Male

My Master is much younger than I am, and it would be entirely accurate to describe him as a twink. Small, lithe without an ounce of body fat in him apart from a certain softness of his facial features, and packaged in soft, smooth hairless skin. He fully enjoys all the greatest blessings of youth, but there is a devil in him. He found me on the internet. I...

BBC: Like Son, Like Father

by silkstockingslover on Jul 9, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. Summary: Father catches son sucking BBC & gets very curious. Note 1: This is a NUDE DAY 2019 story so please vote. Note 2: All participants are at least 18-years-old. Note 3: Thanks to Tex Beethoven and Robert for editing this story I'd just gotten home from work and was in the k...

Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...