dressing up stories and histories

"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....

This is an absolute work of fiction. The places mentioned are real, but any characters in the story are made up and are not meant to resemble anyone in real life. Any coincidence is purely that. With that, I hope you enjoy the story and please leave feedback, whether good or bad, so I can use it to improve for the next one. Thank you and love to you all....

It has been so long since we last saw each other. Our lives continue on their separate paths, and it is months, sometimes, years before we get the chance to meet again. I have been looking forward to this day for so long and now it is finally here. The anticipation is making me tremble already as I look around my very luxurious hotel bedroom, well worth the extra cost for this extra special occasion. I need to get ready, hardly daring to believe that you will be here in just over an hour. I don't want to di...

Veronica Vol. 1: The Table
A caged sissy is invited to serve ten men under the watchful eye of Beverly, the woman who remade her. Powdered. Plugged. Presented. And perfectly polite.
by Miles Vane
This story is told from Veronica's perspective. If she speaks to you -- if you want more of her, her world, and her weekend -- look out for future stories in this arc. You can call her Veronica Vane. She likes that....

John was my very first gay lover. I wrote a story about our first time together you can find on my page titled 'Big John'. To briefly recap, I was a 50-year-old, recently divorced man in Florida who decided to explore my life long repressed gay side and met 63-year-old John through a 'silver foxes' gay dating web site. He had a similar back story and had never had gay sex before either. We had been lovers for 3 years when I had to move back to California to settle an estate. John was also going to move back...

This confession is the third chapter of a follow up series to my earlier series "College Crossdressing Confessions." I suggest you read the first two chapters of this series and the entire earlier series so that your will understand the context of my confessions. I would like to thank Ken Nitsua for his editing assistance....

I sat down at the computer, slightly nervous and giggling as I opened up my notifications, knowing there would be something left for me. Routine and consistent, in the year that I'd known her, Mistress Katrina hadn't slipped up once. An online Domme, at first starting off as some fun, light play between us, holding keys, sending cute random tasks for me to complete, but it had blossomed into her full and total control over my clit....

CHAPTER 1
It was a picture of a pretty young woman smiling in a cheeky way. She was wearing lovely lace panties with a bar across her boobs giving the size and style of the contents of the packet.
I kept it in my drawer with the panties, so that each morning she would be smiling up at me as if to say "You naughty old man!"...

The 'Girl' in the Bathroom (MM) Pt. 03


Disclaimer this story is purely fictional and all characters are over 18.

When we-and by we I mean I-finished up under the bleachers, I saw my friend Kelly was sitting down on the turf field, so I went to join her. "I saw you and Jack Warren heading under the bleachers together," she said. I just giggled at her comment. "But I thought he was straight?" she responded, asking the obvious question....

Chapter 15
The tormenting massage seemed to go on just about forever in Victor's eyes as Jeremy took his sweet time massaging his butt for half an hour. While he had to reluctantly admit that the massage did relax his muscles, that was about it as it wasn't a relaxing massage at all. It was nerve wrecking, making him more tense than he had ever been, the groping assault of Jeremy's over eager hands, combined with the position and worst of all the throbbing cock poking into his stomach without mercy was d...

Sweet Dreams are Made of These Ch 03
With the new breast forms that Jennifer got me, we needed to shop for new clothes to fit me. Except, I thought it would be on line verse at the mall. Jennifer did my make-up and a wig. The transition was amazing. I think I even got a couple of looks from a number of husbands and a lot of leers from their wives. The fact that my already very short skirt kept creeping over my stocking tops and garter clips probably was the reason....

"Oh, god! That feels so good, baby! Don't stop! Please, don't stop!" Randall moaned as he looked down at his sissy fuck buddy who was on her knees sucking his cock. Lyla was a beautiful and very sexy sissy that Randall had been hooking up with for about two months and he could not get enough of her. She was slim with a big round ass that Randall would worship with his mouth every chance that he got. His tongue would move over every inch of her asshole until it was wet from his saliva....

The powder blue abaya flapped in the humid wind as I made my way through the bustling streets of Manhattan, a covered girl walking elegantly, submissively, through the crowds of tourists and deranged homeless people that occasionally assault you, especially when you are a Muslim woman, and therefore an easy, fragile target....

It had been several months since I moved away from that small town and it had been so stressful moving to a more populated city but it was an opportunity to meet and hang out with more people.
Believe me... I had become really good at dressing up and fantasizing about meeting new people but I was becoming more and more restless from not having a regular thing with someone....

The moment my Amazon delivery arrived, my heart started pounding with excitement. I was barely nineteen, and my mother was away for the weekend with her boyfriend, leaving me home alone. The parcels were a collection of personal items I'd bought with my birthday money, items that would turn me into the girl I longed to be....

What an experience I had. First I just want to say that trying to drive a car wearing high heels and a full blown wedding gown with huge skirts was damn near impossible. Just getting in the car was an adventure. Not just because of the unmanageable and ungainly dress but also I was still terrified of being seen and recognized....

Prologue:
"So, it's agreed then, in order to determine if lesser males can be made to serve a far greater purpose in society, we should implement the beta testing protocols immediately." The tall slender and well endowed woman at the head of the table in the boardroom asked her assembled colleagues....

******************
Hey, I'm back. Some themes to expect in this one: feminization, chastity, humiliation, degradation, pegging, ffm, and a very loving wife.
If you don't like these things, you may not like this story. Otherwise, carry on.
******************
I guess it all started the night of the annual summer party. My work was known for throwing quite an event each year. My wife, Sandy, and I were in the car outside the retreat center. She rubbed her hand against my crotch, causing my cock to ...