Gay School Stories

116,911 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Becoming CD Mistress Raven's Slut Ch. 02

by Vodka_Jim on Dec 10, 2018
Transgender & Crossdressers

Author's Note: I took some inspiration for this next chapter from some of the comments, both public and private, that I had to the first chapter. In doing so, I've written about things (e.g. forced cross-dressing) that I've never personally experienced. Most of my writing is based on things that I've experienced and that I think I can relate. So, if I've mis...

Chrysalis of Kirsten Ch. 03

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

Ignite

by Inthemood4three on Oct 19, 2020
Group Sex

This was the first time my husband Todd and I were on vacation without our kids in tow. We were staying at a nice beach resort in the Bahamas. It was gorgeous, calm, and relaxing. After two days of doing nothing but swimming and shopping, we met a nice couple about our same age, mid to late forties: Mike and Jen. They were from the west side of Florida, whil...

If the Shoe Fits: A Shoe Fetish Story

by silkstockingslover on Nov 16, 2020
Fetish

If the Shoe Fits: A Shoe Fetish Story Summary: Shoe obsession leads to submissive sexual exploration. Note 1: This is dedicated to Kevin, who requested this fantasy. Note 2: Thanks to Tex Beethoven for editing this story. If the Shoe Fits: A Shoe Fetish Story There are two things I love to do every day: work out and jerk off... although it's usually...

Praying for Rain Ch. 02

by DeadSince2001 on Sep 19, 2017
Mature

Kelly and I slept peacefully and my internal clock had a rare morning of malfunction, letting me sleep until 7am. When I awoke, Kelly was still soundly asleep curled up in a ball facing my chest with one of my arms draped across her body. I removed my arm and rolled back slightly so I could look at her and I was struck by how young she looked at that moment....

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

Church Dad

by pghpa on Sep 12, 2017
Erotic Couplings

Anyone who knows me at all knows that I love having sex with married men, particularly if they've not cheated on their wives before. Nothing tells me I'm sexier or more desirable than to have a man want me so badly that he'll break his marital vows, betray his wife's love and trust, and break one of the Ten Commandments just to experience sex ONCE with me. R...

When Marriage Cools: Casey

by IraBumblefield on Sep 13, 2017
Loving Wives

The universe was unfolding according to plan. Every choice I made in my life seemed to be the right one. I was known as 'Lucky Les'... little did I know, that would soon change to 'Luckless'. -- The love of my life was my 35 year old wife Casey, 5'7", 130 pounds, all woman. She taught math and Phys Ed in a neighborhood high school, the latter subject being...

Surprised AF

by loerics on Jun 26, 2018
First Time

No one under 18 engages in sexual acts. This is my first time writing in the Literotica First Time category. This is my entry in the National Nude Day (July 14) Contest. If you like the story, please vote. If you don't, please give me feedback. * I was eagerly pounding my hard cock into my girlfriend's warm wet pussy when she announced, "Josh, I invited...

The Joke

by magmaman on Sep 15, 2017
Loving Wives

{This one has cheating in it, sort of. So if you will be outraged, I don't care.} +++ "How come you never gave me one?" Marie asked me out of the clear blue sky. She was sitting looking at her laptop, we had it hooked up in a wireless flood off of our main system. My ears perked up, she had a teasing tone in her voice I had not heard for awhile. "Gave you...