dressing up stories and histories

It is every crossdresser's dream to find a girlfriend who is really into helping him and sharing with him the joy of being a girl. I was lucky enough to find just such a girl. We had only been dating for about a month when we decided to live together. And it was only about another month before I opened up to her about my love of wearing beautiful lingerie and dresses, and using make-up and wigs to complete my look. Her reaction to my revelation surprised and delighted me....

You look so pretty.
Such a simple phrase, yet it almost seemed like mind control when it was used on me. My dear friend Shawna had found out years ago, wanting to play more with my feminine side, that using those four words absolutely melted me into agreement. I tried to fight it, to protest, to summon the courage to finally resist hearing them, but to no avail. One phrase, and I was hers....

The summer after I graduated from high school was a hot one. You would think that first summer after escaping from school would be carefree and fun for me. But it wasn't great because I was underemployed and worried about my future. I couldn't afford to go to university. My parents split up a few years ago and between them they couldn't afford to foot the bill and there was no way I could earn enough doing odd jobs. To make matters worse most of my friends were away at sports camps or family vacations and I...

The characters in this story are of legal age and all fictional, I reserve all rights of copying this fictional story.
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Hello everyone, I hope you enjoy this short story.
Standing at the alter, waiting on my beautiful bride. looking as she starts down the isle and towards her future husband I can't believe how stunning she looks in that white dress and with that sexy smile on her face as she slowly makes her way up to the pastor and myself, my future bride smiles and gives me that littl...

Sweet Dreams are Made of These Ch 06
"That was your soccer buddy, Jerry." Jennifer informed me as she hung up the phone. "He heard from Ted about Jacqueline and wants to hire her to work at his poker night."
I stood there stunned as my girlfriend had decided to hire me out as a sexy, slut maid to my friends and soccer pals. Ted had come unexpectedly and found me dressed up cleaning the house. He didn't recognized me at all or at least didn't seem to recognize me. Maybe it was my big, G-cup boobs that ...

Steph woke to the sound of a phone alarm and a tongue so foul it felt furred. The apartment had an aftertaste, a chemical sour of latex and disinfectant and, if she was honest, something more feral beneath. She blinked up at the ceiling and let the pounding in her skull tick through the night's events: the parade, the eggs, the aftermath in the bathroom, where Jamal had laughed so hard he nearly pissed himself (and then actually did, onto the ruined skirt Annie had left in the tub)....

I was looking out the front window when Crystal pulled into the driveway. I walked out onto the porch before she could get out of the car.
"Wow," she said as I walked to the passenger side. "I guess you're ready to see this place."
"Don't see any reason to put it off," I said as I got into the car. "Where's Maddy?"...

The morning after the public live stream and the mother goose challenge began with two things: a parched tongue, and the memory of having laid a full clutch of eggs on a public park bench. Both were impossible to ignore, and neither was helped by the kitchen's ruined state--the stink of latex, the feathers trampled into the tile, the gold eggs rattling in a grocery bag by the sink. Steph was up, hair tied back, making espresso and answering texts one-handed. She didn't say good morning....

I published this story and took it back, but I'm republishing again. If you enjoy it please do let me know so I feel confident enough to do the same with the following parts.
This is a fictional story that I have combined with some of my own personal experiences. Everyone is over 20.
A rainy day in the winter we were heading to my friend David's house to work on a project for college. We have known each other for a year and a half and had shared a lot of good bonding moments together and become really...

The next morning, the world was still spinning. The eggs were gone, but the chat--Jamal's favorite word now, "the chat"--was alive, carnivorous, hungry for more.
Annie didn't sleep, not really; she drifted on a tide of shame and adrenaline, alternating between hours of staring at the ceiling and hours of scrolling through the anonymous DMs that filtered into the sissy stream's tip jar. She was famous now, in the exact way she'd once spent years online praying she'd never be....

Alex and Casey had done things in the bedroom, that others would say are taboo, before. But tonight, Casey was going to make sure things were different. Casey has been trying to build up the courage to fully take control for the past couple years. She knows her husband has Femdom fantasy and he has been open to sharing them with her. In fact, they have done a number of those things in the bedroom but almost always at Alex's lead. They have used a strap-on and a cage before, but it usually is because Alex ta...

"Now you'll want to pair some very sheer, nude pantyhose with that little black dress and these black suede pumps, Stephanie sweetheart." Van dispensed fashion advice while applying her makeup in front of her vanity desk mirror.
"But my legs haven't gotten enough sun yet. Won't that clash with the black?" I may have gotten quickly used to being Stephanie but I still was a little bit shy, especially considering Van's boss and playmate was a true fashionista....

The morning after, Steph woke in a tangle of sheets, skin sticky and over-sensitive, mouth still haunted by the memory of salt. Her first thought was to roll over and find Annie, maybe pull her close, feel the tremor in her chest and apologize for whatever was left to be sorry for. But Annie wasn't there. The only sound in the apartment was the air conditioner's distant wheeze, and Steph's own pulse, sharp as a metronome....

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....

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....

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...

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...

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...