dressing up stories and histories

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....

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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.
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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 ...

My experiments with crossdressing and indulging my pantyhose fetish were becoming unsustainable if I was to continue raiding my mum's undergarments and dresses. I was begging to be caught that summer. On top of that, my parents had begun to badger me about my plans now that I had left high school. I graduated with a 3.0 gpa but just wasn't motivated. Beyond my circle of role playing game buddies, I had no friends. My latest girlfriend had already moved out of her parents and was getting ready to attend univ...

All characters are over eighteen and all references to past sex happened between consenting adults. Enjoy.
My name is Peter and I was a colossal disappointment to my father. Thats a profound understatement.
My father's name is Paul Vittore. Now that's Pauly to his friends and family but to everyone else it's Don Vittore....

My girlfriend Nancy and I had been together about eight months and she had moved in with me after the first two months when I came across a video she had made with her former boyfriend, Charlie. It was a sex tape and it graphically showed the two of them, fully nude, having intercourse which was preceded by Nancy putting Charlie's enormous erection into her mouth. Charlie was not circumcised and when Nancy pulled the foreskin of his cock down he had a huge red helmet to his cock. Nancy's blow job of Charlie...

Walking through the afternoon heat to the condo, I saw right away that Ron's car wasn't in the drive, so I let myself in with the key he'd given me that morning. It had already been a long day rehearsing music and marching. And, the mix of emotions were bubbling inside me at the imminent possibility of Ron being home, and the increasing uncertainties about what happens in our next confrontation. But the house seemed quiet. Where was Uncle Ron....

I was showing Mrs. Annalise Anderson around the estate property when she took the initiative and probed my mouth with her tongue. She stripped off my clothes and revealed the camisole and panties I wore beneath my male clothes. Surprised at first, she then basically attacked me. She fucked me hard until I came inside her pussy....

What A thrilling time I was having at Aunt Mary's place. On my very first day she caught me wearing a maids dress while pretending to suck off one of her sewing dummies and for my trouble, I got her strapon straight up my ass. I also got to wear any dress she had laying around that seemed to fit me as well as any other female clothing....

I spent the evening in my bedroom watching porn on my computer. Normally I never watched porn at home or on my smartphone because mom was always barging in without knocking and checking my phone but since she decided to go shopping and I had just been fucked in my ass, I decided to risk it.
I immediately started with gay crossdressers and quickly moved on towards diaper porn and found a huge selection of porn and stories about beta males in diapers getting fucked by powerful men....

Editor's note: this fictional work contains scenes of completely fictional incest or fictional incest content.
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All characters are above 18. Warning some use of derogatory words.
"Robin! get me a beer please." my Dad shouted from the living room. I was in my room trying out some new lingerie and gender neutral clothes. I had on my lacy light blue thong and matching B cup bra with a pair of short booty shorts that were definitely a girls clothing option and topped off with a graphic t-shirt of ...

Not even one full semester and I was flunking out of college. I knew this was gonna happen. I was never good in school and barely maintained a "C" average. I hated sports too. No reason to think I would do well at college but my parents had insisted.
They had money and even though I could only get into a state school, they were proud....

Dear Reader, a couple of things. First, you should probably read the first two installments of this series to get some background into the characters. Second, this chapter is a story about cross dressing, pegging and lots of male on male contact. If this offends you, don't read it, duh. There will be a lot of sex, both straight and bisexual, mf, mfm, mm, fmf, etc. And, evidently there will be at least another chapter. I had planned on our main character going further in his bi-sexual journey, but I ran out ...

John looked down at his hard cock which was dripping so much precum. It was long, thick, and a vein running up the length of it which was throbbing. He smiled as he wrapped his right hand around his cock.
"MMmmmm! Fuck me!" The volume was up on John's laptop so he clearly heard the very sexy sissy as she rode the man's cock. She was moaning with her eyes closed now and her tiny cock was in a pink cage....