Gay Master Sissy Stories

3,801 results
Orientation
Length
Source
Infinite Scroll

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...

House Rules Ch. 08

by EROTICbearscribe on Aug 12, 2019
Gay Male

READERS: The story of Kitten is beginning to cross boundaries into other genres. Just as Kitten has changed and evolved, so is his story changing and evolving. ***** Chapter 14 SEDUCED AND SISSIFIED "What's this, let's see. Oh I feel sexy
. What's come over me? Oh, here it comes again. Oh I feel released. Bad times deceased
My confidence has increased. R...

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...

House Rules Ch. 06

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Eleven WORK TO DO & BUTTERFLY KISSES I fixed breakfast the morning for the both of us. I was wearing pink hipster panties with the word SASSY across the seat and a white cami with pink trim which showed my flat belly. The material was lightweight and tight against my lean torso. You could clearly see my nipples which were as pointy as gumdrops. My...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...

A Submissive at Heart Ch. 04

by hotbottom1 on Sep 2, 2017
Gay Male

Introduction First off I wanted to comment that I am sorry for the long delay between chapter 3 and 4. Life has been busy and while it was important for me to conclude this story I have not had a lot of time as of late. I will say this will be the second last chapter in my crazy adventure that I call my life. I will endeavour to write the 5th and final inst...

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...

That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

Bottomed Out Ch. 02

by capresque on Sep 14, 2017
Gay Male

When I awoke, it was dark, but I couldn't tell what time it was. For a moment I couldn't remember what had happened and why my whole body was sore and sticky with fluids. I felt my arms and legs being released from the ropes holding me spread eagle on the bed. I was shoved off the bed onto the hard floor. With one slap on my ass I was reminded of all that ha...