School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Amy & Beth Get an Education

by walterio on Sep 26, 2017
Group Sex

INTRODUCTION Amy Snyder was thrilled when she learned from the head mistress that her uncle would be picking her up on Friday afternoon. Her uncle Richard had arranged with the school to let Amy spend the weekend with him and his employer William Russell at Mr. Russell's estate. Best of all was that Amy was allowed to bring her roommate Beth Hopper along fo...

Me and My Uncle Ch. 01

by jack_straw on Sep 12, 2017
Novels and Novellas

I guess you could say that I'm a survivor. Looking back on it, it's a wonder that I did survive, considering what I went through for the first 22 years of my life. I have survived losing my father before I was 2-years-old. I've survived being dragged all over the country by my alcoholic, drug-addicted prostitute mother. I survived being sexually molested b...

School of Futas Ch. 04

by FutaMonster on Mar 12, 2019
Transgender & Crossdressers

Author note: Here is the fourth part of this series. Just a word of warning: it can get a little bleak at times and the first part of this chapter does have more than a hint of Non-Con/Reluctance to it which is why I tried to make the second half more light-hearted. I hope it doesn't put too many people off but every story needs a villain or two and things c...

Daughter's Initiation into Lust

by silkstockingslover on Nov 18, 2019
Illustrated

Summary: Cheerleader, principal and daughter learn about true obedience. WARNING: This is a story that includes sex in church, misused biblical quotes and a Minister who misuses his clerical authority to sleep with high school students, married women and his own daughter... if such things offend you please don't read. (Also, scripture is constantly misus...

And The Horse You Rode In On

by TexasFarmBoy on Sep 18, 2017
Novels and Novellas

Year One Gerald Murphy was screwed and he knew it. He preferred to be called Gerald but for some reason, most people including his now ex-wife and former boss called him Jerry. He went with the flow but it still rankled him sometimes. But what people called him was the least of his worries. His primary concern was what a 35 year old man was going to do afte...

The New Swim Team Pt. 01

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this story in late 2015. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever happened in real life. All the names, places, or events living or dead are purely coincidental. ***** Part 1~ Meeting the Team. During the summer of 204...

High School: Zero to Hero Ch. 07

by yoursilentknight on Sep 25, 2017
Group Sex

As always it is recommended that you have read the prolog and pervious chapters up until this point. While the action is hot and heavy this is just one chapter out of a series. High School - Chapter Seven: Championship level antics The New Years party was a major success. Justin and Will were welcome members in our trusted circle and the girls were eager t...

A Ruined Life Ch. 01

by MSTarot on Sep 19, 2017
Romance

A single conversation, overheard one night when I should have been asleep, was the absolute ruin of my life. I had drunk far too many glasses of tea with dinner and got up to go to the bathroom sometime after midnight. As I passed mom and dad's room I heard them arguing. That they were doing that this late at night caught my attention more than anything. T...

The Preacher's Daughter Ch. 3

by Hcstuds on Sep 15, 2017
Mature

Billy and Lucy had taken their time with her return trip to Johnson City. While they had not actually stopped at a motel, they had made brief stops along the road. When they arrived at the parsonage, church was still in session. He helped her take her things into the house and they kissed passionately. He reluctantly left her and went over to the church. He...

Friendships Ch. 02

by Troughton1963 on Oct 14, 2017
Non-Erotic

Thanks, Tigerssman for helping with this story. * One night, while relaxing at a party a gentleman posed a question to Molly, "Molly, how is Daisy doing?" "She is doing great, something great just happened to her." Another friend asked, "How long has it been since you talked to Daisy, Molly?" "It has been over two weeks, a long time for us." The first...