Sissy Schoolgirl Stories

13,642 results
Orientation
Length
Source
Infinite Scroll

A Sissy Saga Ch. 16

by Snurge on Sep 15, 2017
Novels and Novellas

It was after supper, but the evening sun still shone through the lofty windows of the gymnasium to catch dust particles floated weightlessly in its slanting streams of light. A naked young man who promoted the delicate aura of a fragile girl stood fumbling over his words before the seated figure of Miss Twist, groping helplessly for an excuse to explain the...

A BDSM Sissy finds Daddy Ch. 01

by Secret_sissy712 on Jul 13, 2020
Transgender & Crossdressers

As I walked back to my van after finishing up the apartment complex two men pulled up in a van and park a few spaces away. As I open my door and I take my tool belt off my shirt rides up just enough for them to get a sneak peak at the red satin thong panties popping out the top of my jeans. The fact that they do is no mistake. I wear them high and the jeans...

A Sissy Saga Ch. 06

by Snurge on Sep 15, 2017
Novels and Novellas

The following day was Sunday. Margaret Pardoe never resented being duty-tutor on a Sunday, it was the only day of the week without any kind of formal lessons and she was only responsible for overseeing the pantywaists when they strolled outside in the grounds. That said, much of the time she could idle away in the headmistress's study in pretence of monitori...

The Path to Happiness Pt. 04

by brendachaplin2000 on Oct 8, 2019
Transgender & Crossdressers

After couple of days I had settled in to Roger's spare room. I cleaned and cooked for my room and board, not that I was a great cook, but I could warm up food without burning it. I was living full time as Brenda now. My last outing as Brian came when I went to my Store job and quit. I had only worked there a few weeks but the manager wished me well when I t...

Stepsister's Surprise

by PantyWarmer on Sep 12, 2017
Transsexuals & Crossdressers

I was twenty when my father re-married. My mother walked out on us when I was six and Dad was always right there for me. Fourteen years raising me all by himself, sacrificing his own personal needs and desires and now that I was grown it was his turn. I believed that and I was happy when he found Jane. ‘His Jane,’ I would say making a spoof on Tarzan. Jane...

Aztec Art - The Path to Submission Ch. 05

by Sputnik57 on Dec 23, 2017
BDSM

Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

My First Time as a Sissy Ch. 02

by SissyTara on Sep 13, 2017
Transsexuals & Crossdressers

This story is about my journey to being fucked as a sissy for the first time. Part One should be read first. ***** When Raoul left after I had given him the first blowjob I had ever given I was feeling confused. I knew that I had enjoyed it but, didn't know how I felt about having to do it again as he had promised I would have to. I guess I wasn't going to...

Slave Ch. 01

by slaveheathen on Sep 25, 2017
Fetish

My name is slave. Of course, that's not my real name, but for the story I plan to tell, it will do. For the record, I'm a bisexual submissive male. There are few who know this fact. Common enough story there, I suppose. Truth is, my family and friends could never accept my lifestyle, so that part of myself stays safely locked away. But behind closed doors....