Crossdressing School Stories

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The Valentine's Teddy Bear

by PostScriptor on Sep 13, 2017
Loving Wives

The small group of young women were sitting around the table in the company lunch room chatting, an everyday occurrence. An observer would see them laughing and talking, enjoying the time before they returned to their respective desks, in their various departments. Alice, a slim redhead in her mid-twenties, turned to the woman directly across from her, and...

Oral Exchange At School

by culo_hombre69 on Sep 14, 2017
Letters & Transcripts

I can't believe the day I just had! I love reading the stories on this site, but never in a million years did I think I'd have a story to tell! So I'm a maintenance/custodial worker at a local high school here in Arizona, OK? I started a few weeks ago. Soon after I started, I met the Music teacher there when I got a call for a repair of her desk. Her name i...

Wylder Sisters

by succa4luv on Sep 16, 2017
Exhibitionist & Voyeur

All characters participating in intercourse are 18 years old and/or older. ***** My name is Hannah. I'm the middle sister in a set of triplets. Savannah is the eldest, and Juliannah the youngest. We all were creamy fair skinned women with variations of green eyes and long thick brown hair. We grew up in a 4 bedroom 3 bathroom house on Arlington road in...

The School Hike Ch. 01

by Tiger1978 on Aug 28, 2017
Group Sex

I was just about ready to trust myself again. It had taken time but I was just about over Adam. He'd been my first – my first guy that is – and the whole thing had been risky. I was his 34 year old teacher, and he my 18 year old student. I could have lost my job, and it would've been pointless telling people that he'd seduced me not vice versa. My career wou...

The Podiatrist

by anaflowerchild on Aug 18, 2017
Fetish

He was up to his neck in loans, $100,00 to be exact, when he graduated Podiatry school. He had been there for four years and was well schooled in surgery math and chemistry. So he shared an office on 9th Avenue with another young fledgling. Business was slow for a while until his partner, with computer skills put up a wonderful web site, bringing patients in...

Fantasy

by mpknight on Sep 16, 2017
Toys & Masturbation

This is a note from Mark to Linda in which he describes a couple of his masturbatory experiences. My dearest Linda, In your note you described how you masturbated when you finally had a room of your own. It struck a responsive chord in my memory taking me back to my early 20's. I began acting out my fantasies in my bedroom, at night, with all of the lights...

My First Time with Tammy

by Reminiscing on Sep 3, 2017
Erotic Couplings

*** I will begin with a little about myself dear reader. I am now a happily married man with all the responsibilities that entails. However once upon a time I was young and fancy free as they say in the classics. So although I love my wife dearly I do enjoy reminiscing the golden days of yore. All the tales you find me submitting here are true and recalled a...

Lessons in Biology Ch. 01

by GuyJD on Sep 12, 2017
Interracial Love

So far, a month has gone by and thanks to Mark, Ebony's grades have gone up in nearly all of her classes. The coach has already told her that she has made the cheerleading squad and that she will be given her first practice in another week. Why shouldn't she become a cheerleader for her high school? She has a great body of 36C-24-36, beautiful black hair dow...

Walking Through Shadows

by Silver_ink on Sep 15, 2017
Sci-Fi & Fantasy

Master Orlaigh lifted his eyes from the papers on his desk and looked out of his study window. For some reason, he was struggling to concentrate this afternoon. As chief mage to the court of King Taral Shadowbane, Orlaigh was tasked with many things. Lately, his main concern had been the school for nobles that the King had put him in charge of. For too lon...

Of Black Men And Time Travel

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

My beautiful wife lies besides me after a night of passionate lovemaking. Her name is Lasouda. And she is the Queen of the Bagayobo people of Mali, deep within the motherland of Africa. Anyone looking at her would see a six-foot-tall, dark-skinned young Black woman in her twenties. And that's fine because that's what they are meant to see. If only they knew...