Gay Sissy Boi Stories

901 results
Orientation
Length
Source
Infinite Scroll

My Inner Slut

by SlutAlexR on Oct 9, 2018
Gay Male

So lets start from the beginning: I've been married for 12 years. Don't get me wrong: i love Bridget. We have our ups and downs, like every couple. But I do love her. However, sex life isn't what it used to be. And for about a year now, I have been having these recurring cravings to be with men. I don't know where this comes from, or if it will go away. But...

Backdoor Man Ch. 05

by SEVERUSMAX on Sep 16, 2017
Gay Male

We were startled into standing up as we heard Sherry and Sanjay re-enter the dining room/kitchen area, the somewhat dazed and enchanted delivery guy now being bent over the table, as Sherry winked at me and strapped on her dildo with her thigh harness. She lubed it up and spread Sanjay's now smooth cheeks to add some lube to his sphincter before she began wo...

My Neighbor Made Me Do It Ch. 04

by CapnSteelBoy on Sep 14, 2020
Gay Male

My Neighbor Made Me Do It -- Ch. 4 by: CapnSteelBoy Author's note: I hope you're enjoying this series, this chapter sees our boi taking things along his path of self improvement! Please comment if you have the time, as reading your reactions excites me into writing more things! Or drop me a line to let me know how much you love/hate this stuff! Cheers!...

The C&s Club Pt. 04

by yukonnights on Oct 19, 2020
Gay Male

We both sleep late, when I finally come back to life the first thing I'm fully aware of is Shannon's warm body snuggled close to mine. The night was cool and the open window makes snuggling even nicer. I lay there, not wanting to lose this experience of waking up to such soft warmth next to me. As my thoughts drift, last night replays in my mind — he actuall...

First Meeting Ch. 01

by cutewht26mtoplsyou on Sep 14, 2017
Gay Male

*all references to characters, locations and events are fictional. Any similarities between this story and real life are purely coincidental* Today is finally the day and I'm so excited! Daddy is finally going to visit! He's coming all this way just to give me what I crave and I couldn't feel luckier. His instructions were simple: "dress slutty. Charge th...

There Was Something About Him Pt. 02

by eviltwin52 on Sep 14, 2020
Gay Male

My young man takes me deeper into the lifestyle. I lay with dannie in my bed. My head rested on his small chest and I was teasing his nipple. "Tell me about the nipple ring dannie." "It was a gift from my Daddy. Like the tattoo on my neck that you haven't mentioned but I know you've seen it." "You're right, I have seen it. I'm not 100% sure what it means...

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...

My Coming Out Party

by eviltwin52 on Jun 1, 2020
Gay Male

I knew this day would arrive eventually. My wife and Mother insisted on it. Many times they'd sit and talk about me as though I wasn't there giving them pedicures. Pedicures. It's not as easy as it sounds. Cindy, my wife decided that I needed to get some skills and literally took me to the local community college and enrolled me in a class that trained gir...

Keeping Count

by isadore on Jun 26, 2019
Gay Male

It had been a while since I had been at the spa and I wanted to make an impression. I had contacted a few tops and had told them of my idea of putting on a show and they, collectively, agreed. So here I was making a 2.5-hour drive so that I could get my groove on! While I had parked my car and walked across the street, I imbibed in a bit of a joint and by t...

A Hotel Seduction Ch. 02

by Dormrat on Sep 16, 2017
Gay Male

I woke up quietly to the soothing feeling of a soft back massage. Large strong fingers kneading my stiff shoulders and neck. The masseur must have felt me stir because the massaging slowed and I felt warm breath on my neck. "Good morning, stud" was whispered in my ear. Suddenly flashes of last night started rushing through my brain. A run-away river of ima...