Gay Sissy Brother Stories

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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...

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...

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...

From Brother to Bitch Ch. 02

by Mixedwritings1993 on Aug 29, 2017
Gay Male

James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares. He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling...

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...

My Sissy Roommate

by Kent100 on Sep 14, 2017
Gay Male

Disclaimer: I enjoy writing these stories, both for your entertainment and mine. This story involves, gay sex, non-consensual sex and bi-racial sex. If this offends you, read no further. Like most writers, I do appreciate your comments and votes. Thank you. * It was 1996, my first year at college and my first time so far away from my home, my family and my...

Coming Home: Davis Brothers Ch. 04

by robcub32 on Sep 25, 2017
Gay Male

"Fuck!" Brandon slumped back with a groan. "God damn, you know how to suck cock." Lonnie raised his head from Brandon's lap and made a show of swallowing the remainder of Brandon's load. "I love sucking you." "That fucking mouth of yours is gonna give me a fucking heart attack." Lonnie snickered, then planted a kiss on the end of Brandon's cock. He let i...

Coming Home: Davis Brothers Ch. 02

by robcub32 on Sep 25, 2017
Gay Male

"Ugh. Be quiet," Benji moaned as he slapped his hand on the buzzing alarm clock. He rolled over and snuggled up to the warmth of Ben's side. He scratched his fingers through the thick auburn colored fur in the middle of Ben's chest. "I wish I had the day off with you." Ben sniffed and cleared his voice, still gruff from sleep. "Well, you're important now, M...

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...

You are a Sissy Pt. 05: Master

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, sissy. Welcome back, princess. Welcome back to our journey through your sissy mind. You will always come back because I am what you want. I am what you need. You need my soothing voice. You need to hear my voice telling you what a fucking faggot you are. You need my voice telling you what a faggot you have always been. That makes you so happy. You...