Sissy And College And Training Stories

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Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

Sissy College Ch. 01

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All characters 18 and above. This series will eventually be filled with all the raunch you desire, but I like a little foreplay first. So sit down, slip down your panties, and enjoy! I love your comments! Chapter 1: Mathematics Welcome to Chester College: An exclusive all-boys Sixth Form College catering to talented young men from across the country aged...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

Cockland Island Pt. 01

by Sissyhalo1 on Oct 8, 2019
Transgender & Crossdressers

It’s actually called Huntington Island. And it’s been around a long time and most of us in the area didn’t know much about it except they brought in guests and stuff by sea plane and set out for a lot of food and deliveries. I mean it was a mystery and not around town. Most people worked there from town ended up staying there because it was this private re...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Cheap Sissy Whore To Call Girl Ch. 03

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

My first few days at the hospital wasn't the typical hospital stay. I'd get fucked by everyone who worked there. Most of the time I was too dazed to realize what was happening but there was always a cock or a pussy that needed attention. The doctors would come in during their breaks to ass fuck me. The nurses would make me lick their pussies clean. I didn't...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...