Gay Sissy Feminization Stories

761 results
Orientation
Length
Source
Infinite Scroll

Beauty and the Beast Pt. 03

by Suzzique on Jun 3, 2019
Gay Male

"Well, well!" said Daddy in a tone of mock surprise, "Your Uncle Ted has made it here after all. And for once he's timed it just right." "You promised," I cried out, on the edge of tears again. "I lied, you dumb sissy. I lied." He laughed. "Cut the jokes, Jack. Give me the bitch. I've come a long way to get my cock up the little slut. I want her now." "...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

Hallowiener Pt. 03

by forummj on Jun 18, 2018
Gay Male

I yanked my cap down tightly and bowed my head. Hunching my shoulders forward I pulled my rucksack tight to my back and made a dart for the front doors. All my fellow students made their lazy way to class as the bell rang. I felt like they all knew what had happened last night, and I didn't just mean the party. I was nervous, almost scared that they knew. "I...

Uncle Marty Pt. 02

by Marty Fisher on Dec 23, 2019
Gay Male

This is a spinoff of my Brotherly Love series where my brother's son discovers his uncle's special talents...Part 2 *** I never thought "tomorrow" would arrive, but it did, and I woke up with my small penis tenting my panties thinking about what I was going to do today. Rose was sound asleep next to me as I thought about what had transpired between my brot...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

Special Inducements

by bjmichaels on May 1, 2018
Gay Male

I was reluctant, but my ex-boyfriend Brian talked me into going to his younger brothers graduation pool party. We were sitting in my car in the parking lot of the liquor store. He had bought two kegs of beer and I helped load them in the car. "Why should I torture myself staring at all those eighteen year-old hard bodies?" I jokingly asked him. "Because yo...

How Did This Happen to Me?

by bjmichaels on Dec 12, 2018
Gay Male

I live in a very expensive condo in one of the most exclusive and prestigious buildings in town. Most of my neighbors are very wealthy retirees. They generally purchase their condo's with cash. I have a five-year plan where my condo will not only be paid off in full, but I will also have a net worth in seven-figures -- yes, you heard me right -- I am thirty...

Off the Grid

by puzziboi on Jan 22, 2020
Gay Male

There sat a cabin. Small. Sturdy. Well-built. A short hike off the Appalachian Trail. Just two-and-a-half miles from the nearest town. The owner was a man in his mid-fifties with gray-green eyes, a dusting of frosty hair on his head, and a full, untamed white beard that covered much of face and came down to his upper chest. The man had two dogs - both mutts....

Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

Finally

by yesplease8 on Sep 25, 2017
Gay Male

I have been happily married for over 10 years. My wife and I are sexually adventurous and open-minded. We have always openly shared fantasies. My wife always makes an effort to realize all of our fantasies. My wife, Anne, is a beautiful woman who takes very good care of herself. She is a natural blonde with natural 36 D tits and firm, muscular legs. Out in p...