Boarding School Stories

107,279 results
Orientation
Length
Source
Infinite Scroll

Finger on Sex Business Ch. 01

by EgmontOriginals on Sep 15, 2017
Novels and Novellas

Britt Eagles was teetering on becoming a real slut by the time she was eighteen. * Reeking of sex one evening (she'd been active in the steamed-up parked car of the 30-plus driver), she'd kindly invited her date in for refreshments when was about to drop her off outside her home because he looked so exhausted. Her parents initially ignored them as they w...

Transformed

by jlaliberte on Apr 27, 2020
Amateur

(Note from the author: So I did not expect this to take off as much as it has, but it has been great. If you like it please consider leaving a like it lets me know that people actually like what they are reading and I will continue. Two things people are asking: Yes, I will be fleshing out the different paths but it takes a while. Second, if there is anythin...

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The Engagement

by Gentlemen8p on Dec 29, 2019
Romance

Prologue On a cold Christmas day war broke out, both sides evenly matched, a snow-coated garden their battlefield and snowballs their weapons. The conflict began when the sound of children yelling erupted, the first strike was thrown by Victor a tall boy wearing an expressive coat and a smug smile of superiority on his charming face. His hands protected from...

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Identity Crisis 01

by BabyDreamer on Sep 15, 2017
Transsexuals & Crossdressers

I would like to thank Kriskrossedup for helping me to edit the following story. - My name is Victor Janice and I am eighteen years old. I have never been very manly, always keeping a slim and child-like form. Along with my name, my body simply made me the center of all the kids' jokes. My last name is very awkward and feminine, which has brought me troub...

The Diary of Jewel Delacroix Ch. 22

by BJGoodhead on Jan 20, 2020
Transgender & Crossdressers

The following contains themes of forced feminization, reluctance, non-consent, and other adult topics, so before we begin here are the usual disclaimers. This is porn, you must be over 18 to read this. If not, go away and come back when you are old enough. If you are old enough and this style of erotica isn't to your liking, then go find some erotica that is...

Scottish Boarding School Ch. 01

by HollyRed on Sep 13, 2017
BDSM

It was a shock to be packed off to boarding school- especially at the age of eighteen. I thought my school days were over but due to a very damming report card I was not free just yet. I had enjoyed the last two years of my A'levels a bit too much. Party followed party and my results showed this. I may have learnt how to tease a man's cock up to greet me but...

Sheerview Heights

by swxtchelijah on Apr 20, 2019
Amateur

_Disclaimer this is my first ever Chyoa story I hope you enjoy!- - - - - - _ It was a Sunday, a beautiful Sunday at that and where was I. Stuck inside touring this new ‘prestigious’ boarding school alongside my step-mom and step sister. My real father was fed up with my trouble making and gave me an ultimatum, work or go to military school. Luckily my step-m...

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Dear Father

by Miasorrow on Sep 16, 2017
Letters & Transcripts

Dear Father, or should I call you Sir? Most people around you do. I was five when mother died. Her smile and the warmth of her body were the last things I remember of her. I have an image of you laughing as I was nestling on her lap. After her death I was forbidden to talk about her and was deprived of my chance to grieve for my mother. I know she must h...

Life of Angela Ch. 02

by Alfamann on Sep 26, 2017
Exhibitionist & Voyeur

Fortunately, or unfortunately, I am not really sure, I never did have to make the decision as an eighteen year as to whether I would show my brothers more of my pussy. Shortly after my parents were involved in a motor vehicle accident, which fortunately they survived but my Mum was going to be in hospital for a period of months as she had sustained a number...

Hello Again

by EgmontGrigor2018 on May 2, 2018
Romance

Chapter 1 Resting on the sofa with thoughts tumbling through her mind, Di Stewart realized that she might be close to being in love with Hugo Salter. That surprised her because while she periodically thought of him, Hugo had disappeared from her life with little more than just the one kiss passing between them whereas some males she'd been associated with...