First Time Sissy Stories

351,143 results
Orientation
Length
Source
Infinite Scroll

Stageside

by MaxiMounds on Sep 16, 2017
Group Sex

Sometimes the most exciting part of my strip show happens in the dressing room after the lights go down... Kisses, Maxi ------------------------------------------ It was the last show of the night and the crowd was thin so I noticed her first. She was sitting stageside with her husband? boyfriend? It didn't matter. As the first song of my show blared ove...

Buns

by Violette on Sep 16, 2017
Anal

This was supposed to be our night, and once again, he fucks it up. Never mind the fact that he's had to watch his back at his job because of recent layoffs, check in on his parents once a week or that on my one day off I got stuck watching after his brother's kids. After two weeks of careful plotting, planning and step classes (to look toned and tasty in my...

Second Opinion

by Ann Douglas on Dec 25, 2017
Mature

It was the last big party of the summer, and with few exceptions, all the guests agreed that it was the best they'd had in four years at Boulder Ridge High School. Technically, their days at Boulder Ridge had ended some six weeks before with graduation, but the numerous parties that had begun with prom night had delayed their final parting until tonight. Com...

In the Darkness

by hentaiboy69 on Sep 16, 2017
Sci-Fi & Fantasy

A.D. 999. In the ancient Continent of Drakoonia, fear for the announced end of the world had taken control in every corner and the same had happened in the small Kingdom of Lombrady. King Lockhard died defending the borders of his realm from the neighboring Kingdom of Swabia and afterwards, taking his place was the pregnant Queen, according to the royal law....

It's Raining Men Pt. 01

by blondechristine2012 on Dec 12, 2018
Erotic Couplings

"Fucking useless men," I said. "Yes they can be." "I have had it up to here with them," I replied touching the top of my blonde hair. "Yes it did sound like that." "You obviously heard us in the garden." "It was rather difficult to avoid Chris." "Yes, I am sorry." "Don't be silly." "Anyway it's kind of you to invite me round." "Not at all that's wha...

Rob and Katie Ch. 01

by writergeek on Jul 3, 2018
Romance

Thank you to the readers of my past stories for taking time to leave ratings and comments. Both are appreciated. I thought that I'd add some variety to my collection and present you with a tale of two college students who rekindle their romance which leads to some fiery passion. As always, your feedback encourages me to continue writing and to improve the qu...

Heather in the Highlands Pt. 03

by ShelleyWingco on Sep 17, 2017
BDSM

Chapter 1. He had to check. To see whether the ghosts had done their magic or not. Only James had felt guilty at not having told Heather that he'd made imprints of the keys before tossing the originals down the vent. That'd had been the worst part of the whole thing for him. The symbolism of throwing those keys away thus imprisoning her for all time. So no...

Bad Penny Ch. 06

by MVPrimetime on Sep 19, 2017
Group Sex

I was woken by the sensation of a soft wet mouth on my cock. Penny was sucking me gently. In my flaccid state she could take all of it inside her, and swirl around it with her agile tongue. It didn't stay flaccid for long. I threw back the duvet and looked down at her. Her face was hidden beneath the mass of curly dark hair, but I could see her bare should...

A 'Swinging' Door Opens

by oldfogey on Sep 13, 2017
Loving Wives

This is the first of a series of true stories detailing how I turned my wife from her rigidly moralistic background to a woman who became one-half of a swinging couple who enjoyed sex as much as anyone ever has. It explains how I slowly managed to convert her from the straight-laced lovely I married to a woman who could trip a man and beat him to the floor....

The Naked Stipulation Ch. 04

by macbuzz on Aug 29, 2017
Exhibitionist & Voyeur

Moving day arrived and the workday dragged slowly. I could finally wait no longer and decided to close the gallery early and drive over to my new home. Just as I was preparing leave, Jules showed up. “Hey DK, I thought I would see were you worked,” she said. “Jules, I’m glad to see you. I was just getting ready to go. “Great,” she said. “I can’t thank...