Crossdressing School Stories

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Infinite Scroll

Running into a High School Mistake

by MissLit on Mar 6, 2018
Erotic Couplings

***This story will be written in several parts. Also, this fictional narrative has a slow start! If a fast paced story is more your style I suggest you don't read this one! Thank you!*** 1 "Excuse you! What are you doing?" I asked while I was rushing down the stairs to my old bedroom. My heart was racing as I saw his hands flipping the pages through my di...

Sarah's Birthday Party

by sarahsmith1989 on Sep 12, 2017
Group Sex

It had been quite awhile since I entered university. Things in my life had become much more tame. I really liked receiving high grades in school and so I ended up spending large amounts of my time in university studying. Since I spent so much time with my nose in a book, I had very little left over for boys, as a result I was single. I pretty much looked th...

All Right I'll Do It

by LaurenWestley on Sep 12, 2017
Transsexuals & Crossdressers

(Authoress note: of course all disclaimers are still in place regarding characters etc., except for one small truth since so many readers asked me to answer this question. Most of the things I write about I did at some point in my life. Perhaps they were not with as many people but at least one person was there. And they were absolutely not done in the order...

Tender Love Hurts Ch. 02

by ImmortalRomance on Sep 13, 2017
Erotic Couplings

Jade Connely had gone with Alicia's sister Brook to see a movie. They had watched "Nightmare on Elm Street Part Two." After the movie was over, the girls walked over to the Malt Shoppe on 31st Street to have dishes of strawberry ice cream and nachos. Just then Erik Daniels came in with a couple of his buddies. Jade saw him enter out of the corner of her eye...

Picture Window

by Archer2050 on Sep 12, 2017
Exhibitionist & Voyeur

John was the typical high school loser, and he knew it. There were a variety of reasons for his lack of popularity, but he knew insufficient confidence was at the top of his list. He was a little less than average height, scrawny, and as far as he was concerned, not particularly handsome. He had friends—other high school losers—and they were all guys. Becaus...

The Note Home Ch. 01

by lesliejones on Sep 14, 2017
Fetish

[All characters in this story are 18 years old or older. Readers offended by descriptions of bodily functions should not read further.] Once more, with love to Megs The worst thing about everything that was happening was that I was an 18-year-old high school girl but my English teacher still sent notes home to my mother. I had asked Miss Steele why she sti...

Telepathic Twins

by dave728 on Sep 4, 2017
Group Sex

When I was in college, I lived in one of those big houses that had a bunch of apartments in it. The two girls who lived across the hall from me (Ronnie and Bonnie) were sisters, and as an added bonus, they were twins. They weren't dazzling beautiful or anything, but they were very nice girls, and I'd probably categorize them as average in looks. Pleasant to...

A Perfect Match Ch. 10

by OneWhoAdores on Sep 14, 2017
BDSM

Part Eighteen: The First Year True to her word the next day Meryn took Jeremy out and they bought a very comfortable folding futon for him to use at her bedside. Their new sleeping arrangement was only one of several things that changed over the next several months. The first also occurred on that first day, when she asked him to stop referring to her as Mi...

Lessons from Sadie Ch. 02

by Rex Siter on Sep 12, 2017
First Time

After that first session with Sadie I couldn't wait for our next meeting. She had promised more. "So much more," in that tone of voice that had my eagerly worked member twitching all over again. At school I was bursting to recount my good fortune to the guys but I had promised Sadie that I wouldn't. Strangely, everyone, including some girls commented on how...

Tabitha, the Naughty Nurse

by LustScribe on Sep 11, 2017
Erotic Couplings

As 18-year-old Aaron Sandmurst waited in the school nurse's office, sitting in his chair with nothing to do but wonder why she had called him over there. Fireside High School's baseball game was one hour away and he had to get ready, which meant that he cannot afford to be late today. However, the school nurse's assistant gave him a note saying that the prin...