Penis Shrinking Gay Stories

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Orientation
Length
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Infinite Scroll

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

Transfer - Brook and Nikita Ch. 03

by SaraChrist on Jun 19, 2018
Transsexuals & Crossdressers

Brook looked back at Nikita with puzzled look. "Um, Nikita while I appreciate that, and I would really like to, I'm spend. You really burned me out." Brook said, pointing to her now flaccid penis that was connected to a trail of cum. Nikita however, took one look at Brook's little buddy, turned her head back and gave Brook a massive grin. Peeling herself o...

The Scarlet Affair Ch. 01

by GallopingStyx on Aug 18, 2017
First Time

Authors Note: All characters in this story are at least 18 years old. The two main characters, Aiden and Scarlet, are both 18 years old and seniors in high school. Chapter 1 - Initiation Aiden walked past a floor length mirror in his house on the way out to school. He was a senior in Kempton High. The reflection he saw was a chosen one. Long black pants t...

Lonely Man Becomes a Sissy

by rebeldoll on Sep 12, 2017
Transsexuals & Crossdressers

I am a 28-year-old male. I'm single and live alone. I work days and usually sit at home at nights and watch movies, and talk online. I do small buying and selling on Ebay for extra cash that I stash away for a rainy day. So most of my time is spent online. I use to be into rock music a lot and have had long hair since I was a teenager. I some how lucked out...

A Trip To The Cum Clinic

by hodownnuzv on Mar 6, 2018
Fetish

"How old are you?" She asked. "Thirty," I said. She stood beside me, her glazed eyes dragged over a checklist that she had put next to where I was laying on the examination table while she snapped on a pair of black latex gloves that were two sizes too small. The paper sat against the side of my bare ribcage and the gentle poke it gave me when she put it d...

Blooming Ch. 01

by Antin0my on Sep 28, 2020
Sci-Fi & Fantasy

The first people to Bloom were college kids. All around the world, 18-22 year olds trying to figure out their future would very quickly have it decided for them, whether they liked it or not. The process of Blooming did not discriminate: male, female, non-binary, lesbian, gay, transgender, pretty, ugly. The only unifying factor was age. No one older than 22...

A Curious, Sexy Dream

by Beejayne on Sep 16, 2017
Sci-Fi & Fantasy

Joan heard the alarm and raised her head. "It's okay honey, that's me. Remember I'm flying to L.A. this morning." Oh thank God, she thought, I can sleep in. It was Rick who had to get up. She'd love to get up and get his breakfast, just like on television, but all he'd eat was cold cereal and toast and coffee anyway. She fell back to sleep. "But don't for...

My Friend Ashley Ch. 06

by jealouscuck on Aug 6, 2019
Transgender & Crossdressers

The evening after Ashley and I showered together, she suggested that we start exploring herbal supplements. It came from her complimenting me on my girlish ways and didn't I wish I had breasts like hers. It progressed to the point that I admitted that I would love to have breasts. After hearing that, she told me about her limited research into the subject. I...

My Real Life Crossdressing Experience

by TammyPanty on Sep 13, 2017
Transsexuals & Crossdressers

I have dressed in lingerie since the age of six. For as long as I can remember I have been fascinated with the idea of being a girl, and many times I wished I was one. As I grew older and moved out on my own I began to buy my own lingerie and learn how to apply makeup. I have had my makeup professionally applied and when I looked in the mirror with my wig on...

A Conference Affair

by SimonAndLara on Apr 13, 2020
Erotic Couplings

Lara and Simon first met at a conference in the late 1990s, when Simon was starting out as an assistant professor and Lara was finishing her PhD. Twenty years later, they were still good friends and saw each other often. They lived in different cities but had stayed in the same field of research. They often ran into each other at conferences and worked toget...