Crossdressing School Stories

105,936 results
Orientation
Length
Source
Infinite Scroll

Sharon Goes Back to School Ch. 11

by RogueAlan on Sep 19, 2017
Interracial Love

original story: Scipio story continuation by RogueAlan Author's Note: Though mentioned above & at the end of the last chapter, I am still getting questions about Chapters 1 through 3. Nick Scipio created Sharon, & has graciously let me run with her. The first three chapters are his, & are on LitErotica under his handle, Scipio555. While you're there, be su...

Nicky Strom-the Peeping Tom

by fmcchris on Sep 14, 2017
Exhibitionist & Voyeur

(Author's Note: My thanks to Allan, one of my very best fans, for supplying me with the wonderful idea for this story!) Hi, my name is Julia Strom. I am nineteen years old and a Scorpio. That's supposed to make me automatically sensitive, secretive, powerful, and most importantly, hyper sexy. But I don't believe all that astrological crap and neither shou...

The Book of David Ch. 03

by bluedragonauthor on Sep 12, 2017
Erotic Couplings

*** -- CHAPTER 3: Delayed Arrival -- *** PRE-COLLEGE (September 1998) "That's right, baby! Grab my tits! Squeeze them! Fuck, yeah, I love your hands on me! Don't ever stop touching me! Fuck, fuck, FUCK! I'm cumming!!!" Doggy-style had become a favorite position for Ellie and me. Personally, I kinda liked it better when she was on top, riding me cowgirl...

Chloe's Story Ch. 01

by MandyM1 on Sep 16, 2017
Novels and Novellas

The Dilemma As the tattooist's needle pierced my delicate skin and the painful process of inscribing the company logo above my bare pussy proceeded, I began to think again of all the chaos I'd recently caused. Derrick's bankruptcy and impending incarceration, the rapes of Carla and Amber, and the anguish that awaits my husband. I knew too what awaits me, th...

Peaks and Valleys

by Saxon_Hart on Sep 19, 2017
Loving Wives

This is my entry into the Legends' day post. I want to thank Blackrandl1958 for asking me along on this venture and for her fine job of editing this piece. Oh and Congrats Randi. I also need to thank Naoko Smith for her help on some of the content of this story. To someone special I need to say, S'agapo Moro Mou. * In addition to being a round heeled slut...

Was It Ever True?

by BlBones on Sep 17, 2017
Loving Wives

I don't know any way to tell the story without first telling you about me. I am Cliff Chandler. In high school, I was looked on as a geek or nerd. My wife of just a little over two years Beverly, Bev, on the other hand, was the head cheerleader, prom queen, homecoming queen, etc. her senior year. Yeah, I know, seems kind of weird doesn't it? While in schoo...

Making Choices

by blackrandl1958 on Oct 30, 2018
Loving Wives

Thanks to my team. They are: Girlinthemoon, Norafares, Hal, Pixel the Cat, and GeorgeAnderson. Harddaysknight is my mentor and gives me critical review. SBrooks103x also gives me a pre-post read. My thanks to you all. Just a light-hearted fun tale. If you're looking for death-vengeance, it is not here. If you just want a story I had fun writing and hope yo...

Single Again Ch. 11

by WhatIKnow on Sep 14, 2017
Romance

As I pull onto the highway towards home I try to call Summer. I'm a bit surprised I haven't heard from her since she left but figure she's just busy with her family. I begin thinking of what our reunion is going to be like next week. I can imagine her tight body against mine, the taste of her lips, the feel of her small breasts. I start to get a bit aroused...

The Seed of Onan Ch. 02

by Silverstag on Sep 13, 2017
Mature

Several weeks had passed since my next-door neighbor, the matronly and very religious Mrs. Packer had discovered me masturbating and, quoting much scriptural chapter and verse, provided what she called 'an appropriate vessel' to receive my seed. Her parting suggestion that the next time I needed to spill my seed I look for an 'appropriate vessel' was much on...

Those Eyes

by dreamsofbirds on Sep 25, 2017
NonHuman

This is my first submission to the site. All comments are welcome... -Santana- I paused at the library doors and stared up at the sun. It was particularly blinding that day but I barely squinted as I stared straight into its brightness. I thought back to another day like this one, a day where the sun was blinding and the air was muggy and humid. I was 17...