dressing up stories and histories

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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 an...

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 pre...

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...

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 u...

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...

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 ...

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 ...

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 immedi...

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 i...

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 b...

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 an...

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 a...

Please enjoy part two of Casting Couch. Suggestions of what you would like to see are appreciated.
Brent constantly adjusted himself in the pleather seats of his 2009 Lancer. He couldn't find a comfortable position if his life depended on it. Was it from the thong constantly riding up? No. Was it fr...

I was sat on the sofa day dreaming. It had been a long time since I had been tied up and I was craving being bound and gagged and helplessly at someone's mercy. My attempts to meet someone hadn't gone anywhere. Lots of people that enjoyed the idea of talking about it, but didn't have the know how or...

Izzy was a punk rock chick with short, spiky, bleach-blonde hair, crooked teeth and tattoos that were far more badass and threatening than my own. She had a tough demeanor but she also had a great sense of humor. She was my kinda chick, for sure. Plus, in my humble opinion, she was hot as fuck. She ...

Standing in my office looking out over the city, I slipped my hand into my pants and began to rub my swollen lace covered cock. My phone beeping brought me out of my trance, licking the pre come from my fingers and checked my message, "30 minutes be ready bitch," my hands began to shake as I strippe...

Hello all!~ This is a mostly accurate story of how I started my sissy journey. Any and all feedback would be appreciated. Thank you for taking the time to read my story!~
The day started off like any other for Grayson as he relaxed after a day of college classes in his dorm. The door to his bedroom ...

This is just a short fantasy to help all you sissies out there get off.
I was just finishing up jacking off in my bedroom. Today's cum rag was a pretty pair of panties I had bought from The Goodwill store. I loved shopping at thrift stores for girly jackoff material. I never wore the stuff, I just l...

This is a followup to "Belle of the Boutique."
It was a great job. My eyes had been opened to a whole new world of sex and sissiness and my ass had been opened up as well. I used t o think of girly dresses as a worthless waste of time and money fit for bimbos and sluts. Now I actually have dreams ab...

(everyone is over 18)
My husband is the most pathetic faggot I ever had the displeasure of marrying, I mean don't get me wrong he's a very accomplished therapist and very dedicated to his work; so, he should know the ins and outs of what a female needs, right? Well for as smart as he is he's pretty ...

I used to hate diapers, not all diapers just the ones I had to wear growing up. I wore diapers my entire life because of a very weak bladder, In fact I had never really grown out of them like most normal boys.
And boy did I get teased for it.
All through school mom insisted that I participate in phy...