Crossdressing School Stories

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Orientation
Length
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Infinite Scroll

Caught Red Handed Pt. 02

by phoenixcinders on Mar 16, 2020
Transgender & Crossdressers

You guys have voted, here are the results. A story where readers get to vote on what happens next. You guys picked the plot and you guys decided on what will happen. All characters engaged in sex are of the age of 18 or older. *** I spent all last night cleaning up the gymnasium, most of it was a blur. When I finally got home, I had to listen to a lecture...

Wanda Chi-Town Aftermath

by Pugzilla on Jan 29, 2020
Group Sex

This takes place after Chi-Town Tuck In Wanda stared at the used condoms in her hotel bathroom trash cans. She was trying desperately to piece the previous night together through the drunken fog. She knew it was bad but she couldn't believe it was this bad. She could remember sucking off the baseball player and letting the school administrators fondle and s...

My Senior Year Ch. 02: Courtney

by burnt_caramel on Jan 20, 2020
First Time

As I mentioned in chapter one, my time with Maya in the computer lab was not my first sexual encounter. That honour went to Courtney. Courtney epitomised grace and beauty, and I had loved her since I set eyes on her at the start of secondary school. She had always been physically more mature than other girls, and at eighteen was tall and slender, with perfe...

A Summer of Tight Fits Pt. 01

by Ralle99 on Aug 6, 2019
Group Sex

Editor's note: this story contains scenes of incest or incest content. ***** *All characters in this story are over 18 years old. *** Tom grudgingly agreed to accompany his father, stepmother, and stepsister, Karen, to pick up her college roommate, Amber, at the Amtrak station two hours away, having been promised a good meal at his favorite Italian resta...

Summer School Pt. 02 Ch. 07

by LilithDeVil on Dec 3, 2018
Novels and Novellas

Hello you naughty girls and boys! So Tom has arrived for his first class and he has already been rubbing and kissing Felicia's feet. He has also been instructed to lick her feet and this is a first for Tom, but surely he will have many more firsts before this summer is over. Having completed his first lesson, Tom has been left to study his Spanish. Felicia,...

Sarah Smiles Orientation week

by smilingsarah on Dec 3, 2019
Exhibitionist & Voyeur

Sarah spent the last night at home attacking her husband. She wanted to leave him well received as she was going to be away for weeks at a time. He would only be able to see her during the holiday. Eating breakfast she got serious and wanted to ensure that he was okay with this plan of hers to turn herself into a super slut. The look in his eyes gave her to...

Daughter's Wedding

by tejmjm55 on Jan 21, 2020
Loving Wives

April 2004, Allen Richards was sitting in his apartment going over his daughter's wedding plans. His ex-wife and daughter along with a wedding planner had planned a very elaborate wedding. He followed the plan known as "Triple S" (sit down, shut-up and shell out). As a devoted father, he was happy to do it. Allen grew up in rural South Carolina. He was the...

Work, Play or Both?

by FlirtandTease on Jun 9, 2020
Erotic Couplings

The Headmaster announced, "We'll have a new graduate student working in the office starting this week. Hopefully they'll be more of a help than a hindrance." Gwen had to roll her eyes. She knew exactly what the headmaster meant. These student teachers meant well, but answering questions all day made the day twice as long. It was quite a surprise when she me...

The Parking Lot Ch. 02

by LatexSolarBeef on Jul 13, 2020
Transgender & Crossdressers

I thought of Val when I went home and the next day. I felt bad that she had to express her sexuality by blowing horny young landscapers in the parking lot of a bar. The Jersey Shore is a beautiful place, but family-oriented and traditional. It's a summer resort area. Once you go over the bridge from the barrier island, it is small towns and becomes quite ru...

Just Look at Me Now Ch. 04

by GFfan on Jul 15, 2020
Transgender & Crossdressers

Let's see... where was I at the end of chapter three? Oh yes: seated on a footrest wearing lingerie and my pink collar, with my eyes adjusting to the bright light now that my blindfold had been removed—and adjusting to the sight of Jude's strap-on in front of my face. "Have you ever given another guy head?" Jude asked. "No, never!" "How about getting a bl...