School Sissy Stories

109,522 results
Orientation
Length
Source
Infinite Scroll

Proud To Be A Sissy Ch. 03

by Kary_M on Sep 11, 2017
Transsexuals & Crossdressers

I woke Monday morning actually looking forward to what the day may hold and feeling good about myself. I felt like I was a different person and as I thought about it realized that in a few ways I was. I laid in bed thinking I did have a little better understanding of my sexuality now that was so confusing just a week before. For a long time now I have known...

Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...

Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

A Sissy Saga Ch. 12

by Snurge on Sep 15, 2017
Novels and Novellas

Poppy returned to the dormitory much earlier than had been planned. Most of the students at the Grange were in special detention and occupied in doing things in preparation for Open Day, but he was no longer a proper pupil and for a while that afternoon he was a free agent. He was feeling active and restless, but he arrived to find the room occupied by the...

Jock Princess Ch. 01

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

I'm Alex. And I got to admit that life's been kinda good. Cake actually. I'm a jock, left winger hockey player and all through high school it's done me pretty well. My family owns a good business in town actually a few of them. Grand dad on mom's side had a dairy farm and actually did okay, Mom's a registered nurse, my dad owns a big hardware store and ad...

Pantsed Again

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Lori ensured I was always appropriately dressed by picking out my sissy girlie things for me everyday; school girl, cotton, bikini panties with support to make my bum round, my padded training bra with built-in forms and knee socks; all white. Lori selected high heeled Mary Janes for me to wear around the house. When I was allowed out or had to go to work,...

Life With Miss Ida Ch. 02

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

When I woke the next day, Saturday – late as it was due to the long evening earlier – I started playing everything over in my mind again and kept coming up with the same result – there was nothing that suggested to me that Ida would not welcome Georgia into this relationship – she never once turned me off, nor seemed turned off by how I was dressed. She didn...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...