Boarding School Stories

107,279 results
Orientation
Length
Source
Infinite Scroll

Can You Have Too Much Sex?

by ainu on Sep 15, 2017
First Time

Society says that being promiscuous is wrong. Fucking a lot of guys is bad. Well, to heck with society. I love to fuck. I love cocks. Pricks. Penises, whatever anyone wants to call them. I'd be unhappy if I didn't. So who am I hurting? Society's rules are to protect females, I'm sure. But having me not have sex with a guy isn't protecting me, it's wronging m...

Restless Ch. 01

by OrionRyter on Sep 15, 2017
Non-Erotic

I was inside my car on day, sitting in the back, waiting for the day to pass, so the night, cool and soothing, would come about decently. I was on the run you see, from a crime most people now-a-days would call stupid and rather ill thought out for someone like myself, a straight-A student at Jasmine High, the north side school of the city Winchester's Peak....

Tom and Paul and Julie

by scheherazade215 on Sep 1, 2017
Group Sex

The doorbell rang. Excusing herself from her guest, Julie rose to answer the door. She was a little perplexed. She rarely got unannounced visitors, and now she had two. It was a cold and rainy night, and Julie couldn't imagine who would be knocking on her door. When she opened it, she got a shock. "Hello." The man before her said. "Tom!" Julie exclaimed as...

High School Reunion

by Patwolf77 on Sep 12, 2017
Erotic Couplings

Just a few weeks ago, I went to my ten year HS Reunion. I went there to be with old friends and show up old enemies with my high paying job, impressive cars and nice clothes. The night was pretty tame for a while, with the usual small talk and such. That was until I ran into the lust of my high school years: Christine. I can't begin to describe to you how mu...

Confessions of a Red Hot Red Head

by red_hot_redhead_confessor on Sep 13, 2017
Erotic Couplings

Entry Two: Mr. Pain. Dear readers: First, I would like to answer some comments left on my last story. Yes, that is how the events naturally occurred. Of course, I omitted random events and facts in the effort of flow, but yes, I was a 22-year-old virgin when I met C. I also hated every single thing about myself. I have no idea where these notions came fr...

My Adventures with Schoolboys.

by ARGEE on Dec 24, 2019
Loving Wives

My name is Stephanie and I am 37 years old. I am married to Stephen who is a very understanding husband. We have only one child, our son Chad who has just turned 18 years. Stephen and I married when I was 18 (Stephen was 22) and the reason we married so quickly was simply I was pregnant with Chad! I had had lots of boyfriends when I was at college and had be...

The Path to Happiness Pt. 05

by brendachaplin2000 on Oct 8, 2019
Transgender & Crossdressers

Today was the day, I will be leaving this town today forever. I now identify myself as a girl, this town is a reminder I was born as a boy. After today I can finally walk free without fear of being outed buy some idiot who knows my past. I had an early alarm call at 6.30am, I showered and shaved and dressed in my underwear, school blouse, and skirt. Next I...

Wesworld: Candy's Interview

by gaildaniels84 on Dec 25, 2019
Transgender & Crossdressers

This story is inspired by a series of captions done by Wes Mantooth over on his blog. Wes has been gone for several years and I'm a huge fan of his work so my intent is to use several of his stories and characters as jumping off places to create a larger world. *** Cameron once again ran his hands down the front of his pants, trying surreptitiously to wipe...

Spring Break with The Sisters Ch. 01

by ejxxx on Mar 17, 2020
First Time

This is my first story, so open to any feedback. This is the first of a series, and it starts a little slow and helps set up some backstory on the characters. Hopefully it will all pay off in later chapters. _________ I gripped the steering wheel impatiently, willing the car to pick up speed without actually pressing down on the gas. The sun, which hung lo...

A Cape Cod Night

by AnOceanLight on Jul 14, 2020
Erotic Couplings

AS each year passed since high school graduation the thrill that summer once entertained subsided. Friendships that seemed indestructible, crumbled from the passing of time and where it had once been comfortable to proclaim to have all the answers now maturity's humbling touch left only questions. Three years removed from high school did not really appear to...