Crossdressing School Stories

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A New Year, A New Perspective

by Oryks on Sep 14, 2017
First Time

This is story is written from half truth. The other half is made up, mostly for literary reasoning. Reading a story with complete truth is not always the most entertaining (at least, not if it's my life.) However, I will be staying within the realm of the possible and not too far from the truth where ever it is wholly entertaining. This is my first story of...

First Time Nudist

by WuLiMaster on Sep 13, 2017
First Time

I was on a business trip to Sydney, Australia and looking through a guide book to see what I could do during my time off. I had already walked across the Sydney Harbour Bridge, toured the Opera House and taken the ferry to Manley but the thing that caught my eye Sunday morning was the nude beach at Lady Bay. As a teen, I had avoided school showers. I was th...

End of School Party

by blndEE on Sep 13, 2017
Group Sex

It was the last day of school of our senior year. We decided to head to the beach and party to calm our nerves before our graduation tomorrow. Seven of us crammed into Toms VW Bug. Tom and Dave sat in the front, and Chris, Lisa, Shane, Bryce, and I sat in the back. It was quite a tight squeeze. I ended up sitting on Bryce’s lap, and Lisa sat on Shane’s. I ha...

Erotic Math

by WestVaCouple on Sep 12, 2017
Erotic Couplings

Why didn't I study harder in high school. Then maybe I wouldn't be taking these remedial math classes in the summer. I mean, I just graduated and I am supposed to be out partying with my friends before we all leave for college. But instead, I work at the pool in the morning, go to class in the afternoon, and do my assignments at night. It's just not right....

The Jamie Reunion

by pneruda21 on Sep 16, 2017
Novels and Novellas

It's Saturday night. Two of my best friends and I are passing around a flask filled with bourbon as we drive in to the historic part of Endicott. You know the exact moment that you're in the historic district because you feel the car beneath you adjust from smooth gravel to the gray cobblestone, which lines every bit of the 10 block strip of this part of tow...

Young High School Football Coach

by jamisonh213 on Sep 12, 2017
Erotic Couplings

Note: This story will be written from two points of view. Lily is a hot wife that has been given permission to roam by her husband. Jonathan is the young coach giving his account of the events. ***** Lily: About five years ago I was working as a nurse at a rural hospital. One of my female co-workers was getting married. The gals at work decided to have a...

Summer Project

by Vitalsigns on Sep 13, 2017
Erotic Couplings

School was out and Bobby didn't have a girlfriend. He would start college in the fall but it was going to be a long summer. He had a job painting houses during the week. His friends all had dates on the weekends. That left him out. He had to do something to occupy himself. He went to the book store. He wasn't looking for good literature. He just wanted some...

Waiting for Abby

by nitewriter34 on Sep 17, 2017
Loving Wives

My first submission and truly inspired by my favourite author "silkstockinglyslover', I'm open to all your comments and reviews. Do feel free to let me know if I should ever write anymore or just be a satisfied reader. ***** I parked outside the elementary school and turned off my engines. It was drizzling and cold outside. I looked my phone to see if I ha...

Heidi Beside The River

by Sandman8314 on Sep 2, 2017
Erotic Couplings

Just where the long trailing branches of a graceful weeping willow tree overhung the path beside the water, I paused to enjoy the view and the cool of the willow shade. I sensed a movement beside me. It was a girl. "Hi, Jack," she said. "You all alone down here?" "Yeah, I, ah...,"I stammered. "I seen you at school." I had seen her a few times on the coll...

Rendezvous with Destiny

by Rebelicious on Sep 13, 2017
Erotic Couplings

Destiny grew up like any other typical girl on her block. Her father was a banker and her mother was a homemaker. Both seemed very happy, but as we all know, looks can be deceiving. One afternoon Destiny walked into her house after a long day at school expecting to find the usual, her mother on the phone or cleaning something around the house. But this day...