Gay Sissy Teen Stories

1,459 results
Orientation
Length
Source
Infinite Scroll

My White Boy Sissy Pt. 01

by wolf_hunt on Feb 25, 2019
Gay Male

This is part 1 of an ongoing series. It's just an intro with only a blow job scene. In future chapters there will be more including forced feminization, anal, humiliation and much much more. Hope you enjoy my story. All characters involved in sex are 18 or older. This is from the perspective of a black teenager as he turns a sissy nerd into his bitch. ****...

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...

Outed and Married

by keptsissy on Sep 26, 2017
Gay Male

He always threatened me with being exposed to my coworkers, to the world as the sissy I am to him. Usually it was part of what I thought was his dirty talk, sex talk. He'd tease me with it. He'd be deep inside of me, slow fucking me, talking dirty into my ear. Or he'd have me restrained and be masturbating me as part of 'my reward', as he called it, and woul...

Masturbate Fantasy #131

by writedoctor on Sep 14, 2017
Gay Male

Journal Entry January 21st Traveling through southern New Mexico. Mid 60's. Warm enough. Staying at a campground in a rustic log cabin. No frills. I like that. Decent Mexican food nearby. Community laundry and very sanitary facilities. Long hot shower sounds good. Wishing for a surprise guest. I confess journal, I have thought about him. Closing eyes. Rand...

Submitting To My Roommate... Ch. 02

by chriscili on Aug 18, 2017
Gay Male

The next morning I woke up and got out of bed. Chris had already gone to the shower so I went to my mirror to see what I looked like. I really shouldn’t have been surprised when I saw that my face was covered with dried cum. I grabbed my shower towel off a hook on the back of our door, used it to dry rub the cum off my cheeks and lips and then wrapped...

Nephew's Readjustment Pt. 10

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed. Please be aware that that chapter may be considered more intense and negative. ***** That evening was di...

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...

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...

Submissive Sissy for 'Her' Man

by keptsissy on Sep 28, 2020
Gay Male

He toys with the lace ruffles on my panties. His fingers move over the ruffles and up and down the crack of my butt. I flick my tongue over the hole of his erection and then take it deeply into my mouth, holding it at the base straight up. His eyes are closed as he lays naked on the bed, his huge hard cock sticking up off of him. I start to pump, start to ma...

LoveLocked: WokeWired

by adamlily1972 on Dec 9, 2017
Gay Male

Dear reader: A political satire of "woke" white people, particularly woke white women. Definitely not to everyone's taste. Intended to be humorous. Skip if offended by the notion of a white gal mind-controlling her white boyfriend to service a black dude. But quaff heartily if the idea gets you hot. Adam ********* SCENE 1 [Setting: A spacious but d...