Small Penis School Stories

274,707 results
Orientation
Length
Source
Infinite Scroll

Watching Jenna

by MadQuill on Sep 12, 2017
Transsexuals & Crossdressers

Please remember this is a copyrighted work and all legal disclaimers apply. I hope that the story isn't affect by the grammar errors. I'm sure there are some errors and I do care. Thank you for your comments. Scene One It had begun many years ago. This feeling that I was different. Being smaller than most of the other kids in school was just one is...

James - 10 Years After Pt. 01

by doubledigit on Sep 26, 2017
Exhibitionist & Voyeur

Sergeant James Doyle entered the Captain's office. Already inside, in addition to Captain Jones was a woman he didn't recognize. "Doyle," said the captain to his sergeant, this is Mrs... "Ms", corrected the woman. "This is Ms. Duncan." James saw a woman, probably around 40 years old, with a good figure. She had high-piled hair that reminded him of a 1960...

Cottage 69 Ch. 03

by Wayne_Richardson on Sep 11, 2018
First Time

This story is entirely fictitious; enjoy. ***** On Monday morning the rumour spread like a bush-fire through the Cedar Hill high school; especially among the boys. "Have you heard? A junior boy claims to have seen up Miss Lambert's dress last Friday. He said she wasn't wearing any panty and her pussy was bald!" Frances (Fanny) Lambert and Janette (Jan) Pr...

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

The New Playmate

by MaxSebastian on Oct 8, 2019
Erotic Couplings

1 When his father got engaged, it was a bit of a relief for Jonathan. Dad had been miserable for years after Jonathan’s mother had died three weeks before his thirteenth birthday. Now he seemed to be back to a vague semblance of his former self. Jonathan was glad - his Dad had been through a lot. Jonathan had, of course, met Dad's fiancée a few times when...

Mrs. Swanson's Boarding House Ch. 02

by 0ra11yfix8ed on Sep 25, 2017
Exhibitionist & Voyeur

Miss Bridgeway led Carl out of the parlor and down the hall to the kitchen using his penis as a joy stick of sorts. "Did you enjoy your first session with Mrs. Swanson?" Carl had just been masturbated by one of the founding Sisters of The Sisterhood a group of progressive women who advocated CFNM as a way of controlling the sexual urges of men, young men in...

The Order

by ladyredmuff on Sep 14, 2017
BDSM

Chapter 1 At the headquarters of The Order of Saint Ishmael, situated in a picturesque castle in Austria, the Grand Council was holding their first, official bi-monthly meeting. Thirteen people, all dressed in long robes with deep hoods, hiding their faces, were seated around a huge and highly polished table. The Order of Saint Ishmael, a latter-day club...

Lucille and Mrs. Miller Pt. 03

by MaryGrangerx on Sep 19, 2017
Fetish

This story is total fantasy and has no relationship to real life or experience. There is no under-age sex or cruelty. ***** You have probably read my husband's account of his conversation with young Brian and our later discussions concerning the situation. Everything he related is absolutely true but inevitably we both had slightly different versions of ev...

A New Me...

by teencdgirly22 on Sep 25, 2017
Transsexuals & Crossdressers

This story is completely true. I hope you enjoy it because I have been dying to write it for almost 4 years now! Hi, my name is Ashley. At the time of writing this story I am a 24 year old crossdresser living full time as a woman. It wasn't always like this however...so let me tell you about how it all began. Chapter 1: The beginning, and going out. Fla...

Corona Widow(s)

by Danman45 on Oct 6, 2020
Group Sex

Corona Widows It started with a phone call while I was parking my car outside the Home Depot. A weak but familiar voice at the other end called out: "Nick, you old rascal -- are you there?" "Hi Mick -- thought by now you would have died from boredom as a paper pusher!" It was one of my very good friends whom I had had many years of working with as a fore...