Crossdressing School Stories

105,936 results
Orientation
Length
Source
Infinite Scroll

The Corner Office Ch. 05

by tom6432 on Sep 14, 2017
BDSM

Chapter V -The previous weekend (This is a fantasy containing spanking and humiliation. If you do not enjoy reading this type of story please do not read it. Thank you to my editor you know who you are.) ------- I was in the dining room of my 45 year old administrative assistants' house waiting to pick up some documents that I needed for work on Monday....

Anal Sex Enhances Your Life

by Samuelx on Sep 12, 2017
Anal

Howdy, folks. My name is Marcus Jean Richmond. I'm a student at Dixon University in Raynham, Massachusetts. Life these days simply couldn't be better. We have a good crop of students this year. The school has eleven thousand students, and it's evenly split between the sexes for the first time in ages. A balanced ratio is something most colleges and universit...

I Am Jack's Life Ch. 10

by Finis on Sep 13, 2017
Novels and Novellas

Author's note and acknowledgements This story has sat on my hard drive for four years now. I wrote it, all twenty chapters and 95,000 words of it in eight days of a frenzied, near trance-like state, sitting on my couch with my wife's laptop. She would occasionally have to remind me to eat. When the dust settled, and I looked up, I realized a couple of...

Dousing the Fireworks

by lesliejones on Sep 26, 2017
Fetish

I have this thing about peeing, both me and other women. I sit in the stall in the ladies room and I hear another woman come into the next one. She rucks up her skirt and I hear the rustle as she manages to yank down her panties and let fly As that first splash hits the water I get a flash of excitement right through me but I quietly massage myself down ther...

My Standard of Beauty: Black Women

by Samuelx on Sep 13, 2017
First Time

I love the Black woman’s natural beauty. It is simply the best in the world. Kelvin Jean-Pierre is the name. A big and tall young Black man of Haitian descent living in the town of Nepean, Province of Ontario. I recently graduated from Algonquin College, where I majored in Business Administration. I transferred to Carleton University and hope to get into the...

Welcome to the Cum Factory Ch. 2

by UforMe on Sep 19, 2017
Erotic Couplings

"Chris, that was the sexiest thing I've ever seen," Tracy sighed, as she continued to rub her hands through the puddles of cum Chris had just created all over her. She reached a cum-drenched hand up and slid her fingers slowly into her mouth, closing her eyes as she savored his taste. "And you taste great!" she said. She looked down. "I can not believe you'r...

The Veronica Story Pt. 05

by jfbreak on Oct 13, 2017
Loving Wives

--Part Five - He is Me -- Over the next month I found that I was leaving my house a few minutes earlier each day that I stopped in for coffee just so I could have a few extra minutes in discussions. I didn't want to arrive too early because I knew that Jonah didn't leave until about seven. I was thinking, if I could get to the apartment within a few minutes...

Hyperspermia Pt. 01 Ch. 01

by novella_champ on Jul 3, 2018
Novels and Novellas

This is module one, chapter one. This is going to be a novella of sorts. The intent is to have 3 modules total covering different times in our main characters life. While it is feasible to read any of these independently, this is a carryover story, so reading them in order is beneficial. Module one, our main character, Stanley, is a senior in high school....

Beth's Family Ch. 01

by Jack1107 on Nov 19, 2018
Mature

Jack and Beth had just had a fantastic session. They had been fucking for over two and a half hours, and Beth had had multiple orgasms. She looked beautiful as they finished their wine. They had met eighteen months earlier on a dating site. Jack would be fifty later this year. Beth was seventy-four but looked in her early sixties. Initially, they had flirted...

Library Fantasy: ALT Ending

by shortblondecutie on Mar 6, 2018
Erotic Couplings

**Everyone in this story is over the age of 18** ***** I walk up the steps of the two story library, the back of my school girl skirt flipping up with each step. We agreed to meet here, our perverted minds needing satisfaction. I walk in and scan the area, seeing where you are at. I check my phone and see that you tell me to go upstairs, to the archive sec...