Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Let's Go to the Movies Pt. 01

by coquette_redux on Mar 2, 2020
BDSM

God, this plug is so fucking heavy. She shifted in her seat for the 300th time since climbing into the passenger seat. She'd already been wearing it for half an hour and she could only be grateful that he hadn't tasked her to do something like grocery shopping with the plug the plug in...again. But sitting on it for this long wasn't much more comfortable....

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Best So Far

by Dari2sltg on Feb 7, 2018
Erotic Couplings

It's almost like a dream being here on the Island. Making it even more like a dream, he's here beside me. To just be able to turn and see his tawny hair shining in the hot August sun, his bare chest bronzing easily in this sweltering heat, his hand lazily trailing along my thigh as we laid there, on the bow of his boat. Thirty seven months, it's been since...

A Sissy Saga Ch. 09

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam Hancock arose in the morning alone but feeling joyous and revitalised. But when her early toilet had been done her smile faded, and she frowned. On the dressing table lay the fat envelope she'd received that morning from the lawyers employed by Lady Diana. It enclosed a letter that was dreadfully succinct. '... Our client as brought to our attention...

The Mad Musings of a Mal-contented

by alan509 on Sep 16, 2017
Sci-Fi & Fantasy

The one-eyed prophet Changoparati, mutely miming his prognostications of doom to the blind, while in pursuit of the pleasures of the flesh and pondering the imponderable aspects of the face of God, who, he thinks he might of seen one day out of the corner of his eye, crossing the street with a aardvark on a leash. I'm simply wasting time while being tempora...

Bimbo! Ch. 02

by DDDDave on Dec 23, 2019
Erotic Couplings

Big Tits, Big Dicks and Fantasy Fucking (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) [ Author's note: We don't get paid for writing these stories so sometime the follow up doesn't get done as fast as I might like. And I am aware that I play games with the names of my characters. I'm heavily into PUNishm...

Getting Down & Physical Ch. 2

by Andrew Ryan on Sep 14, 2017
Group Sex

Chapter Two: Busted! However, Juan's reverie was rather unceremoniously interrupted. Juan heard a knock at the door and without waiting for him to respond, Nurse Presley barged into the room saying, "Okay, Juan. Let's take you first." However, when she opened the door, she saw Juan sitting on the bench, holding his erect penis, which appeared to be as vola...

Bimbo!

by DDDDave on Mar 6, 2018
Erotic Couplings

Big Tits, Big Dicks and Fantasy Fucking (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) (o )( o) "Ralph, come in here a moment. will you?" Mom wasn't really asking. She was telling me. But that was the way she always spoke to me. Bossy and dictatorial behind a phony smile. "Sit down, please. I have some news. You...

Social Networking Ch. 02

by buntsingle1 on Sep 13, 2017
Erotic Couplings

After reading the reviews of my massage of Marie on my wife's Facebook site I was feeling on top of the world. I had just spent an hour massaging one of Heather's best friends in a most intimate way and every one of my wife's friends had proclaimed me the best husband in the world. Apparently, all of the women's husbands really sucked at pleasing their wives...