dressing up stories and histories

Steph doesn't sleep that night. She tries, but the footage keeps looping in her head: the way Jamal held Annie's chin, the way Derek filmed everything, the sound of her own voice in the background--so clinical, so certain, like a scientist vivisecting a pet. In the moment, it had been easy to narrate, to direct, to escalate....

My name is Gemmahh, well, it was Richard not too long ago. I was quite slender, not very muscular except for my long legs. I had swum all through school and college, so my legs were well-toned, my wife would even joke that I had better pins than she did. Yes, my wife, I was a happily married 20-something man....

He wakes up with his mouth dry and a chemical taste on the back of his tongue, the way hangovers always start: not with a bang but with a slow, spreading poison.
The last thing he remembers is Steph straddling him, her voice low and sticky in his ear, and Derek laughing from the other side of the room as they compared notes on how many times they'd made him cry. The humiliation should be old by now, but his body always finds a new way to keep the edge fresh. He's still wearing the breastplate, the silico...

Confessions of a Sissy Crossdresser


Prologue: When I was young, I'd place ads in Craigslist looking for men who liked sissy crossdressers. I lived out my wildest fantasies a hundred times over. This is the story of some of those nights.

Eros Adult Video was a few miles from downtown in a warehouse district. A freight line, overrun by weeds, lies nearby. Train noises came from somewhere in the far distance. Men got out of cars and trucks, shuffled across the parking lot, their shoes scuffin...

It took about one hour for Derek to reply. It took Steph four minutes more to escalate the entire game.
Andrew was naked, freshly showered, with a towel wrapped around his waist and the marks from last night's restraints still faintly banded on his wrists. He was contemplating, with the grim focus of a death row inmate, how to word a follow-up to Derek's "You're a legend. Tell me when and where," when the apartment intercom warbled....

Andrew doesn't remember the walk from the mall to the parking lot. He does remember the way Steph's fingers kept tightening around his elbow every time someone glanced at them, and the way her eyes flicked to her phone, then to him, as if she were already scripting the next scene.
Now he's in the passenger seat of her car--a compact imported thing, beige leather so clean it feels like an art installation. The new perfume from Victoria's Secret hangs in the air, fighting for supremacy with the vague, ling...

"Can I help you, Miss?"
"It's mister, Mister!" Some detective! "I'm here to talk to Lt. Johnson. I just graduated from my High School Police Auxiliary and I want to work undercover--to clean up our streets."
"Oh, you do, do you? What's your name--uh, Mister?"
"Babicock. Bunni Babicock."
"Oh. OH! Oh, yeah. Lt. Johnson said to put you right to work. Undercover, in vice. On Martin Luther King, Jr. Street & Grand Boulevard. That's a real hot-spot. Maybe you can take down Jerome Slick or "Big J" Jama...

Once again a big thank you to Tania Tulle for her guidance and editing skills. I don't know what I would do without my friend and mentor.
If you haven't read any of her great stories, get going! You won't regret it, they are all fantastic!
I've spent most of my life hiding a secret fetish--or should I say, an obsession. I'm not complaining; my life has been fine. I had a decent job, a lovely wife, and two great kids....

All characters are over 18
I let in a sharp inhale as I felt the blunt tip of the dildo enter me. I closed my eyes as I slid down the rubber shaft and imagined myself riding someone, anyone. I picked up speed and rocked my hips, my erection hardening, I began to stroke myself, spearing my ass down on the molded penis. I started to moan, my thoughts showing me as a lithe, well toned woman, chestnut hair in loose curls bouncing on my shoulders as I got fucked by my imaginary man. I shuddered as I came, my ...

Three weeks is a long time to live as a punchline. Andrew had not expected to survive it.
He had learned quickly that Steph's threats were always instructional, never idle.
The morning after the cage-and-plug incident, he'd tried to imagine a scenario in which she lost interest or forgot about him--a vacation, maybe, or the slow entropy of her attention span. But Steph's attention was bottomless. Within forty-eight hours, she had established a schedule: daily check-ins, mandatory photo documentation o...

Chapter 44
Luckily for him lunch ended up being the worst part of his day as not a lot happened for the remainder of it. Still he spent a lot of his afternoon classes just trying to get over what had happened at lunch, constantly going over it in his head. Spending lunch with the girls and their questions had been embarrassing, but by far the thing which bothered him most was the run in with Tom and what he had said. It was hard to process just how far he had fallen in the eyes of his team, his ex friend...

It begins the same as every humiliation: with the sick fizz of anticipation, then the bleak certainty of having no out. For Andrew, the morning after Steph's "proposal" is a time for bargaining--coffee first, then a plaintive, half-joking, "You were serious about the mall?" over the top of his mug, as if perhaps she'd reconsider in the daylight. But Steph is never more herself than when the world is watching, and as she stands in his kitchen, pouring herself a thumb of cold-pressed juice, it's clear there's...

Meeting The Family
Hello! My name is Dylan. I'm 21 years old, and I live in a small town in southern Ontario with my Mom and Dad. Growing up as an only child, I was always close with my parents, specifically my Mom. I didn't have many friends, and I was always excluded at school. I never had the opportunity to play sports; though my tiny build wouldn't have helped me in sports all that much anyways. Despite feeling alone, or excluded; my Mom and Dad always loved me, and tried their hardest to provide for...

Andrew doesn’t know how long he spends in the chemical afterglow of defeat, heart battering away inside the terry-cloth cocoon Steph’s left him in. The room is quieter than it’s been in years, as if even the city has put down its arms and is just waiting to see what happens next. He sits at the edge of his unmade bed, robe cinched to the first notch, and wonders whether this is what rock bottom is supposed to look like: two bruises from a bikini string, the sticky aftertaste of shame, and Steph on the other...

Sweet Dreams are Made of These Ch 05
"But Jennifer..." I started to protest going out alone which wouldn't have been so bad if my clothes weren't so revealing.
My girlfriend had set me up to be dressed as a slut maid and clean our house. Meanwhile, she had told my soccer teammate Ted that it would be okay for him to drop something off for me. All dressed and made up, he didn't recognize me at all when I answered the door. In fact, he tried to have his way with me....

All characters are above 18. Warning some use of derogatory words.
"Robin! Son, where's my 12 pack?" My dad asked when he woke up the next morning. He's been having alcoholic tendencies along with sex withdrawals like the rest of us. I was in the sissy hypno choke hold. I remembered the passionate or rather animalistic romping we had just last night on the couch. After my father came inside my ass, he went upstairs to bed and passed out til today. Leaving me to my own thoughts. My feelings were conflicte...

"Die With A Smile" played on repeat through my stereo as I swayed in front of my living room window, a glass of wine in my hand and tears streaming down my face. Tonight was the night and I had dressed for the occasion even though no one would be there to see it. Tonight, I had opted to wear an emerald green, knee length, wrap skirt over a matching satin bra and panty set. On my legs were my favorite pair of thigh-high stockings and my favorite Black, patent leather, ankle strap pumps. On my head, my Afro w...

"So what king of slut are you?" I tried to act surprised at the question, but as he moved closer towards me and his hand gripped my ass, we both knew he could feel the suspender belt I was wearing under my jeans....
....
So once again, here I am. Straight, married, boring(ish) guy, travelling to another city with work. On the first night I always try to have a social free evening, eat, sleep (ok usually I dress up in my lingerie and play with myself watching porn first) but tonight I was feeling unusu...

This is purely a fantasy not a real story and nobody is real in this story. If my spelling or grammar is bad I apologise. I am just trying to add to this great story site. So please refrain from making negative comments and low marks. If you don't like the story just read others on this great site. But for the ones who enjoy my stories thank you....

I hummed to myself walking home from work, feeling lighter in my life than ever before. The past six weeks, each time agreeing to become a sissy doll for this mysterious group, chipping away at so many worries I had previously held onto. I kept my nails longer than usual, covered in some pretty light pink polish I had found. I kept my eyelashes a bit curled, darkened and more prominent. And I kept my clothes far more femme than before, no longer afraid to let Rory seep into my other aspects of life....

I have mixed emotions about revealing parts of my past but I'm sure there are others like me.
I spent a majority of my working life in construction helping to build the city of Las Vegas also known as Sin City.
Building single family and multi family dwellings in every corner of town had its advantages developing and discovering new parts of the city. My travels for work introduced me to new to me strip clubs and adult stores not counting thrift stores along with countless street walkers ranging from ...

There is a particular flavor to a June evening in the city, especially when the sun has slunk down and the lights inside start to war with the lingering blue of dusk. Andrew's apartment, two stories above an arterial cross-street, has a way of trapping that moment and holding it hostage: the walls painted the color of cigarettes and snow, a single amber lamp illuminating the living room in warm, indistinct pools. Out on the balcony, the city's hum is less traffic than weather, a white noise that smooths the...

He had been nervous as they headed down to the spa and the couples massage that Thea had booked for them. What would they think of his denuded form? He was smooth as silk on his legs and the masseuse would surely notice?
Thea had calmed him in her own unique way. First she started to make out with him until he felt short of breath. A well proven distraction from his small panic attacks....

My soccer team teammate, Ted had caught me dressed en femme but amazingly didn't recognize me at all. I told him I was Jacqueline there to clean the house. I was so convincing that if I let him, he would have had his way with me. I couldn't blame him since I taunted and teased him with my ass. I had to stop and tell him I was from a house cleaning company and that he would need to get me from them....

Karan (22): Sweet, kind-hearted, respectful. He adores Rekha bhabhi (Sister-in-law) -- she's like his elder sister, mother, and best friend. He's a student, soft, not arrogant -- just a bit lost, sheltered by love.
Rekha (32): Dignified, elegant, widowed young woman. She is Karan's bhabhi (Sister-in-law) and she raised Karan like her own. Protective yet playful, she teases him, but her love is maternal, deep, and unconditional....

It's now 12 years since I was placed in protective custody as I was a witness for the prosecution in a high court case. Back then, I was a 21 year old normal guy. I didn't get up to much and not had a large friend group, actually, I had no friends really, I would just hop from job to job to pay for my needs....

This will be at least a two part story, possibly longer. Enjoy!
Finding yourself has become about an unabashedly cliche concept in our modern parlance. It's the perfect cop out to relieve oneself from any preexisting obligation. But, this story uses this to our protagonists' advantage.
But enough ten-dollar-word stuffed preambles....

"I'll be there in a few minutes," the text alert read.
Melody would be meeting her new Daddy for the first time, and she knew what was expected of her. She will be dressed in her schoolgirl outfit, white stockings, black heels, pigtail wig, and secured in her chastity cage. Daddy made it clear that she should not be wearing panties today. She was on her knees, back straight, and facing the door....

It happened so fast and so unintentional. I had revealed my "life" to Deb before Claire had a chance to tell her. If Deb left for home, there'd be hell to pay for certain.
Claire started to say something as I did too. Deb held up a hand in each of our directions and said "Stop. I had most of it figured out before Brad went to bed."...

Summertime
I started dating a girl over a year ago who was nice at first, but I was losing interest. She was getting fat and starting to be a pain in the ass. I decided to let her go and find a good dating site. I joined one and set up my profile with pictures and waited. My headline read, "Seeking Love, Lust and Trust". I began getting a few messages from some of the woman but none I was interested in....