Shemale School Stories

106,125 results
Orientation
Length
Source
Infinite Scroll

Kelsey's World Ch. 15

by riverboy on Sep 25, 2017
Group Sex

Brie and Charity loved teaching at the elementary school. They were only a week in, but both felt comfortable, like they were meant to be there. There had been a lot of turnover in faculty over the last few years, mostly due to retirements, so a fairly large portion of the staff was younger people, including two young men. Justin taught fourth grade, and Ad...

Sweet Little Danielle - Football

by TheSparkZone on Sep 18, 2017
Exhibitionist & Voyeur

My cheerleader friend, Vicki, is one of the best looking and most popular girls in our high school. I, on the other hand, have always been a member of the nerd herd or geek freaks. It's not that I'm unattractive. I just have a high grade-point-average and the guys I hang out with would rather write a computer program than pass around a football. However, I...

Island for Dickgirls: Health Class

by YKN4949 on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This story is one in a series of inter-related stories regarding women with penises. The stories will be related but will not be true sequels. That means you can read one "Island for Dickgirls" story and never read another, read them in any order, or (hopefully) read them all. To aid readers, I will include the same "introduction" section in e...

Innocence Lost

by jmcox261 on Apr 3, 2019
Interracial Love

Maurice Smith knew to count his lucky stars everyday. It all started when he married his pretty blonde wife, Miriam, twenty years ago. It seemed to Maurice that his lovely blonde wife got even prettier and prettier each and every day. He enjoyed looking at her as well as watching the reaction from other men. You see, Miriam seemed to have an innocence about...

La Rubia Gringa

by ReedRichards on Jun 26, 2019
Loving Wives

Not my usual by any means; this is a tale of revenge, and more revenge. There is some sex in it. As usual, the place names are real, but the characters are entirely fictitious, and any resemblance to any actual person, living, dead or undead, is entirely coincidental. No one under 18 is depicted in this story. *************************** How many years d...

Dad's Lost Bet

by thehumpman on Sep 19, 2017
Mature

Everyone is over eighteen in case anyone did not know. * Once again it's football season and as usual I had all my friends over to watch the game on our satellite television. They did not come for just the games, they also enjoyed being around my mother. My mother looked good for her age, at thirty seven years old and all of my friends never failed to com...

Oh My! Ch. 01

by pactrvl08 on Sep 12, 2017
Erotic Couplings

Julia Redmon lived in New York City with her mother in a one bedroom loft. Her mother moved them out there from a small town in Alabama when she was 12 years old. Her mother wanted Julia to get a better education and better opportunities later in life and thought New York was the best place to provide that. Mrs. Redmon, Julia's mother, had saved up enough...

The Fluffer

by swingerjoe on Sep 19, 2017
Group Sex

For every skill that exists, there is someone who is better at that particular skill than everyone else in the world. It is simply a matter of logic. Whether it is sprinting one hundred meters, hurling a baseball sixty feet, driving an automobile, or even eating hot dogs, someone, right now, is the best in the world at that particular skill. This is the stor...

Suburban Underbelly Ch. 01

by fastandsloppy on Sep 14, 2017
Group Sex

Dear prospective reader; this is a four part group sex tale that also contains other flavors of sexual perversion. It is a work of fiction and is meant to be entertaining rather than enlightening or socially responsible. I will post the chapters 2 -- 3 days apart. All characters are at least eighteen. *** It was about three fifteen on a hot Friday afterno...

The Fifteen Year Awakening

by exjock on Sep 17, 2017
Loving Wives

Many thanks for an unbelievable degree of help from WestVACouple Who edited and made numerous suggestions to liven the tale and make it more readable and much more erotically vivid. ********************** Ellen and I were married in our sophomore year of College. We had dated throughout High School and ended up going to the same university with identical P...