dressing up stories and histories

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.
*****
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....

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 from the butt plug? A little. Mostly, it was from the spanking and thrice the hard anal sex he endured from Carmen and Colby....

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 the willingness to take it from chat to reality....

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 didn't have an over abundance of tits or ass like Delilah but she had a really nice figure, a slight tan, a British accent and not to mention, she was a total slut and a pervert, like me and Delilah....

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 stripped off my suit and shoes and stepped into the pair of high heels beside me. Sitting at my desk I secured my long blonde wig to my head and applied some makeup. Standing my pulse quickened as I waited....

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 firmly shut as he laid back in his bed, scrolling on his phone looking to roleplay with. His eyes scanned over low effort post after low effort post but eventually stopped. The name "BBWsweetie19" popped out a...

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 liked squirting my cum all over it....

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 about being a bimbo and a slut in a pretty dress....

(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 fucking dumb, our wedding night was the worst night of my life; I couldn't even feel his small dick going into my pussy. He was crying because he was saying how good it felt or some shit, I don't know, meanwhi...

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 phys ed like all the other kids so my diapers were always on display. At least mom allowed me to wear pullups on days when I had to go to the gym instead of my normal diapers that crinkled when I walked....