Sissy High School Stories

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Woodstock Era Memories

by louienohio on Sep 12, 2017
Non-Erotic

There were many other high school friends, guys and gals. These guys were not on the football team and the gals were not cheerleaders. One friend was Pat, an Italian kid like myself, he was from Grandview. Of my high school guy friends, Pat was the most involved, successfully involved, in the rock and roll music scene. Pat was a talented bass guitar player,...

How Did This Happen?

by ComfortablyCold on Sep 12, 2017
Erotic Couplings

How did this happen? Jacqueline and I had been best friends since our sophomore year in high school. Our relationship had started simply enough – I saw her; I was attracted to her; I wanted to talk to her. It was her cute features that did it for me, I guess. Jackie was shorter than I – a rarity in and of itself. She was about 5’1 with small breasts and long...

Graduation Day

by Ewriter111 on Dec 25, 2019
Interracial Love

I had just turned 18 in December and I was college bound. I should have been at my high school graduation this June summers day and instead I was in a vacant classroom with a janitor named TJ trying to deep throat his monster black cock. I guess I began celebrating early. It seems since a maintenance worker named Sylvester found out I turned 18 in December,...

Hockey Girls Chronicles Ch. 01

by JETitFuck on Jul 27, 2020
Erotic Couplings

I had transferred into a new high school mid-way through senior year as my parents had moved into the town for work commitments. On the first day of school, I was told that there were a few more students who were transferring in as well, alleviating my concerns and soothing my nerves. While I was sitting nervously in the general office, two beautiful girls...

June

by rmlooker on Sep 11, 2017
Fetish

June first appeared in My First Blind Date, Ch.3. Sexual content. * When June was 10 years old, she fell from a school yard gym and broke her back and spine at T5. When she hit, there was a metal tube on the ground that supported the apparatus and her back hit on this tube. A few weeks after the injury a spinal fusion was done in the area of T4 to T6. Jun...

The Four Years: Year One Ch. 08

by The_Dork_Knight on Sep 16, 2017
Novels and Novellas

The week of midterms came and went. It was amazing how easy the tests actually were, especially since all my teachers made them sound like grueling torture. Every night after the last test of the day was done, Rosa and I would celebrate by fucking half the night away. We even started to go at it on Thursday during lunch in my room, but we were interrupted b...

Mrs Henderson's New Job

by carmenlee on Sep 13, 2017
Exhibitionist & Voyeur

Chapter 1 It was a bright, sunny day as Charlotte Henderson drove up the driveway that led to St Jude's School for Troubled Young Men. It was an imposing, official-looking building; it housed between five hundred and eight hundred and fifty men between the ages of eighteen and twenty-one, all of whom had been in some trouble with the law. St Jude's was a la...

Muslim Lesbian Nerd Diary

by Samuelx on Sep 15, 2017
Interracial Love

Ah, the life of a young brown Muslim woman living in the City of Ottawa, Ontario. My name is Choukri Ali, and I was born in the neighborhood of Vanier to a Somali Muslim father, Ahmed Ali, and a Pakistani mother, Amina Khan. I'm used to people looking at me and my family. You don't see a lot of African Muslim men with South Asian wives, so my parents and I g...

Class Reunion

by John_Spivey1966 on Sep 13, 2017
Erotic Couplings

The invitation for my 10 year high school reunion was stuck to the fridge and I felt it mocking me each time I saw it there. Just divorced after a horrid two year marriage the last thing I wanted to do was go to a reunion to talk to people I didn't give a shit about 10 years ago and cared even less for now. Plus how do you answer the inevitable questions of...

Two Old Friends

by Baldguy72 on Sep 13, 2017
Romance

I had always had a thing for Tracy ever since we met in 8th grade. She was a very cute girl back then and was built in all the right places. She used to really give me a hard time and I was so stupid that I never realized that she liked me too. We ended up at the same high school and would see each other quite often in the halls. I would usually just smile...