dressing up stories and histories

My Sissy Life

Chapter 1: Sadistic Roommate

My first college roommate was a psycho killer whose skin and hair had an unnatural yellow and brownish color to them. The other guys in the dorm, the drunken fools, the ones who harassed me for studying, lived off beer and pretzels. I didn't fit in. I did...

The following story is fiction and bears no connection to real events.

I was in Billy's arms, both of us naked and wearing only our bras, garter belts and stockings. We pressed against each other enjoying the feeling of our bodies so close together. Surprisingly our cocks were again hard as they ru...

After Vana left the house I put her shoes back in her room and hung the soiled dress back in her closet.

Returning to the living room I settled onto the sofa sleeper still wearing the pink panties my aunt told me to wear shopping the next morning.

Taking the wet panties my aunt had left me and the...

CHAPTER 1

I fell in love at the age of eighteen. We both did, but it took ages for us to understand it. Her name is Denise, but always known as Dennie. Mine is Roy.

She was in the next room when I arrived at university. We introduced ourselves, and she said "By the way, I'm a lesbian, so don't get...

My first meetup was in some woodland near my home. I'd got chatting with another crossdresser online. Eventually, talk of meeting up happened and we agreed to meet that evening in a location that we both knew.

The excitement was building as I put my outfit on. As I fastened the basque, I couldn't b...

In nothing but my cousins panties, my little hard on pushed out against the precum soaked panty fabric. Almost like a guiding beacon my little pecker pointed my way down the hall as I could feel my excitement building with every step forward I took!

On my way to the garage, I noticed the door to my...

Author's notes: All characters are 18+.

This was previously published in the Interracial category under a different title, which meant a lot of the intended audience might miss the story. So... take two.

Similar stories: 'Fishnets / French Maid', 'First Time With Black Best Friend'

******

I nerv...

ODE ON A GRECIAN TURN

By Katharine Sexkitten

By anyone's standards, he was an exemplary man, inside and out.

Tall, and handsome, fit, and gregarious.

Appealing to those he met, with his open vitality and his natural enthusiastic curiosity about everything and everyone, he had an honest care and ...

Having been the youngest of my family I looked up to my sisters who were twins and two years older that me. My Brother was ten years older and very much into sports and very macho I was the opposite very skinny and grew my hair long mainly to take after my sisters but the excuse I gave was the image...

Ladies' Night

by Kris Cherita

Chapter 3

WARNING: Unlike most of my stories, this one features gay male sex scenes as well as femdom and feminization. I don't usually write bisexual male smut, but a few scenes occurred to me and the only way to stop thinking about them and write something else was...

MY WINNING STREAK

By Katharine Sexkitten

"Kid," he said, "if it wasn't for bad luck, you'd have no luck at all."

And he was right.

Not about the 'kid' part, since I was thirty-two at the time, but he was my boss, and older, and he'd always called me that. And he was indeed old, not so much in ag...

Maid Games, Pt 15

(Cross-dressing, FFm, sissy, DS, FLR, maid, corset, chastity, consensual, reluctant, feminization)

By ChangeYourPassword ------------------- Ms. Kendra Grey

Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not f...

Chapter 63

While Jake was mortified and incredibly nervous about this whole thing, he had to admit that Rebecca was very sweet and sympathetic. "Relax sweetie, you have nothing to be embarrassed about, in fact I think you look incredibly cute. Now let me just get to work and I'll make you look as p...

I install car stereos for a living, which mostly means I spend my days lying on my back in the footwell of somebody's pickup truck with a flashlight in my teeth, trying to get a wire through a hole that the factory never meant to have a wire in it. I'm good at it. I'm patient, I don't mind tight spa...

Earphones in place to block out the noise, I was asleep almost before my flight home reached cruising altitude.

As I slept, a dream came to me that made the in-flight entertainment system superfluous.

I stood in the elevator lobby of the convention hotel, halfway to the top floor, facing the catwa...

The next 2 weeks bled together in haze of indoctrination, use and submission.

Monday: Mary's text at 8 AM. Come over. Mike just left for work. Sheila was at their house by 8:45, the French maid uniform under a trench coat, her heels clicking on the welcome mat. Mary opened the door in a silk robe, ...

From Ashton, "Ashley" is born. The true story of how I became a crossdresser. if you haven't read chapter one, please read it first.

Chapter 2

Friday, and the school pep rally is in full swing. It's homecoming and as we always do, we are playing our rival. Sitting with the rest of my team, Sam and...

Cops and Robbers

How Laura became my girlfriend, I'll never figure out. She was a strong, take charge person. She decided when we went out, where we went or what we did. She had a hot looking body with a nice big set of tits and long strong legs. Me, I was three inches shorter than her five ten sta...

We pick the story up a year or so later, and a fair bit has changed. Steph and I were no longer an item, as she was in a placement year and I was in Year 2. We were still good friends, FWBs, and I had taken on her apartment lease, as that meant when she came back to University, she could pick it up ...

HIS LITTLE SECRET

Chapter Two: The Secret Behind the Door

There are two things I've learned about men.

The first is that they rarely tell you everything.

The second is that the things they try hardest to hide are often the things they fear you'll judge them for.

I didn't know which category Dan...

I'll start with a little backstory about my relationship with Ashley.

Very early in life, I realized I was submissive and had strong fantasies about hardcore femdom.

We entered our relationship as an FLR and have built on that foundation to become what we are today. My wife embraced the dominant r...

TENDERNESS

By Katharine Sexkitten

What have I done?

The wind was howling, whipping at my face. My longish hair was blown all over the place. Most people would worry about how it looked, I suppose. But I didn't care about things like that. Certainly not now. I never had, really. The sun was fully ...

THE BRANDYWINE ESTATES SCRABBLE CLUB

By Katharine Sexkitten

The chair made me invisible.

They couldn't see me, and I couldn't see them.

It only took me a few seconds to realize it, which was long enough to also understand that whatever was going on, it was surely meant to be in private.

There w...

Greetings good people this is a fantasy about Stephen and Sandra.

I hope you enjoy it, if it is not your thing just move along, find something that is.

Are lead couple had been together a while and as things often do in the bedroom had become monotonous predictable. Once maybe twice a month, if th...

I could see the guy who'd knocked on my door through the peephole, bathed in the garish hallway lighting.

Wearing an ill-fitting black suit jacket and striped tie the man looked to be in his fifties or older, a short and squat brown human with a bulky chest and a couple of chins and a hat that look...

DESPERATE MEASURES

By Katharine Sexkitten

It's fury.

It's indescribable fury.

It's literally hell on earth.

There is no beast on the planet more brutal or unforgiving or unpredictable than a forest fire. It has no conscience, and no empathy. It destroys everything in its path, and it choses whe...

I moaned softly as I stroked my cock. The femboy on my laptop screen moaned too, much louder than me, as he got plowed from behind. His dress was hiked up to expose his bussy to the muscular, big-dicked top.

My own dress, really just a babydoll nightie, was also hiked up slightly so I could jerk of...

I've always had a thing for women's lingerie that started when I'd play hide and seek using the clothing racks in department stores while my mother shopped.

The store displays dressed in the newest, sexiest lingerie outfits with garters and stockings, clothing items that you just don't see everyday...

I am not sure why I am the way I am but, not having a father figure and growing up in a house with three women could have something to do with it. I am addicted to women's clothes, I love the look, the feel, and I love dressing up. We lived not too far from a truck stop near the interstate, and I wo...

Small Note: Apologies for the delay. Had too many life problems to keep working on part two. Here it is in its form and I abandon the previous cadence for the sake of eroticisms. Please feel free to share your thoughts and opinions in comments below. Thank you for reading and have a beautiful day!

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