Smutty Sissy Stories

7,210 results
Orientation
Length
Source
Infinite Scroll

A Cross Dressers First Time

by webbyhose on Sep 13, 2017
Transsexuals & Crossdressers

I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour. Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet...

A Body Re-awakened Ch. 02

by Fluffybunny2020 on Oct 6, 2020
Exhibitionist & Voyeur

A body reawakened: the watcher It might be helpful to read my first short story of the same name to get some context for this one. Jack was on a high. Fifty lengths of the pool and he felt great. As a researcher in the university he often needed to find a way to release pent up energy. His job was tedious at times, but necessary to work his way up the lad...

The Art of Writing Smut

by Boxlicker101 on Sep 14, 2017
How To

Writing smut, like any other kind of writing, takes a certain amount of skill and knowledge. Some writing skills are not required, such as establishing characters or plot development, because the only thing the dedicated readers of smut care about is graphic sex, and the more detailed it is, the better. Character is less important than the sizes of his cock...

My Big Fat Pornographic Wedding

by GratefulFred on Sep 1, 2017
Humor & Satire

(C) - GratefulFred I still remember the day when my papa was giving me a lift to school with my buddy Jimmy. “Jimmy, did you know that most words in English have a root in Pornish? Give me a word. Any word will do,” said papa who once again embarrassed me as usual. “How about “Frosty the Snowman” Mr. Cockinpussypuss” Jimmy asked. “Yes…Frosty is like Frig...

The Library

by mrguitarmn on Sep 13, 2017
Exhibitionist & Voyeur

One Late night while studying in the library. Jack wandered around in the basement where all the bookshelves that slid together were. He slid some together so that no one would bother him. It was finals week and he knew no one would be in his section seeing how it was already close to midnight. It was Saturday and most of his friends from the music departmen...

Legend Of Echo

by KourtneyB on Jun 29, 2019
Fantasy

Before the adventure begins, a quick description of the star of the show, Echo: An 18 year old human woman. Her lithe, 5'5" body is topped with shoulder-length shiny Raven hair. Her back and chest have the fairly easy job or supporting a pair of perky B-cup boobs with small areolas and very sensitive nipples. Past the slight but pleasant curve of her hi...

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Blowback

by dreadknots on Jun 18, 2018
Transsexuals & Crossdressers

Another story! This one is a sorta reversal of a typical mind control scenario, where the slighted nerd ensnares the stuck up bitch. What happens when it backfires and turns a horny guy into a sissy sextoy? Lewd shit, obviously. *** Chloe flicked through the tabs on her laptop's browser, skipping between links and trying to polish up her history paper. Thi...

Gardner's World

by Trudydoes on Oct 31, 2018
Group Sex

"They're here." Shouted Jane up the stairs to her husband Charlie. "Ok, be down in sec." Came the muffled reply, through the closed bedroom door. There were three of them; a couple of young lads in their late teens or early twenties, and a bloke of about mid-thirties who was clearly in charge. He introduced himself as Mick. They were here to landscape t...

A Mother's Sonnet - Audio Version

by mejau71 on Nov 2, 2020
Audio

Disclaimer: This audio is made by an adult FOR adults, and it's purely fantasy. All characters are fictional and are 18 years and older. The slow gentle burn of a Mother's love that embodies the allure and romanticism you've always craved. Give in as your mother takes you through an aural kaleidoscope of forbidden delight that all men madly crave. Not a qu...

Fantaria

by Crazyman69 on Apr 17, 2020
Fantasy

Fantaria is a large blue planet, filled with all kinds of creatures: the dragons of the mountains, the monsters in the dark forests of each country, and many more. Take an adventure dear reader through several mystic and wonderous lands! From the deserts of Savagia, to the lush forests of the Teracotan empire, to the vast dungeons of bandits and Lords in the...

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