Sissy College Stories

78,474 results
Orientation
Length
Source
Infinite Scroll

Sissy_World 01

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

The sun beat down on the land of Washington D.C. of the United States of America. Normally, it was cooler in the spring months, but no one in the area around the White House was going to be cool. No, they were too tightly gathered together for them not to be hot. The occasion? The inauguration of President Jessica Phoenix. Thousands upon thousands of peo...

Mother Dear Pt. 12

by keptsissy on Sep 14, 2017
Fetish

My white frilly lace panties delicately pulled down passed my stocking tops, so as to not crimp the lace, dangle from my ankles. The twelve inch small chain that holds my ankles and the thin steel cuffs locked to it rests on the carpeted floor, the panties rest on top of it and cover the tops of my 3" spike heel pumps. My small but erect penis exposed in fro...

High Society Sissy

by beyondkink on Sep 11, 2017
Transsexuals & Crossdressers

I guess I can say I was one of the lucky ones. Fresh out of an ivy league school with a degree we were met with two different tales. "Sorry, you're over qualified," they said. Or we would hear, "We're looking for someone with more experience." An alum that I had befriend however was able to land me a waiter position in a posh New York country club that ca...

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

Once Upon a Laundry Ch. 03

by thekestrelkid on Aug 20, 2018
Transsexuals & Crossdressers

It had been three days since David had had his first three-way, and dressed as a woman no less! He had relived it over and over in his mind's eye, and masturbated to it every day. It was hard for him to concentrate at work and he even bought a few items to help him feel more feminine. Lipstick, mascara, make-up, nylons, panties and a training bra. Every nigh...

Journey into Feminization Ch. 01

by KneelingNancy on Jul 14, 2020
BDSM

***Chapter 01 - The Beginning Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.). During my chil...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Taking Mom's Place

by Sissy_Sammi_ on Jan 31, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** *All characters are 18+ years old. This is the first entry to this story, so if you like it I can continue it. ***** Jack walked back into his old room with his suitcases in tow and couldn't help but feel the shame and sadness that lingered there. He knew that his father was ex...

Introspection

by Sissy_Sammi_ on Jun 19, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** *All characters are 18+ years old ***** Jimmy was born into a small family in Colorado. His mother was a beautiful woman named Dianne, and his father was a gruff working man named Thomas. If only kids could have been given a choice to be born, Jimmy would have chosen otherwise. He...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...