Sissy First Stories

313,352 results
Orientation
Length
Source
Infinite Scroll

Mimi: A Bedtime Story

by mimaster on Sep 16, 2017
Toys & Masturbation

Mimi came home, more stressed than when she'd gotten home the first time. Work had been stressful enough...the long days and tenuous tasks that came with working as a legal assistant at a lawyer's office had drained on her. She felt the job was rewarding in its own way. And she loved her boss. But all the work she did was behind the scenes. She never got to...

You Were with Me All the While Ch. 01

by chryseme on Sep 13, 2017
Erotic Couplings

After an extremely contentious and miserable 15-year marriage, I wasted little time getting an online dating subscription so that I could safely sample the fruits of the dating world—and perhaps start a relationship that would eventually turn into satisfying and mutual love. I needed to be loved. I really needed it. And I had so much to give a kind, secure,...

Becky Ch. 01

by Many Feathers on Sep 15, 2017
Toys & Masturbation

Author's note: This is to be a series of short stories centered around two main characters. Becky and William, her father. It is a story about a woman who for numerous reasons as I'll later explain, has been sheltered by an overbearing mother, and a father who allowed it to occur and who allowed himself to be equally bullied by his wife. The mother dies, th...

Amy's First Day At Work

by patuk54 on Sep 1, 2017
First Time

It was Amy's first day at the hospital, having finished college and passed with flying colours her mum and dad had really high hopes for her future. So did Amy, although her father is a consultant now at Amy's hospital he insisted she start at the bottom of the ladder and hopefully work her way upwards to wherever her ambition takes her. Morning in the Lay...

Christian Linda in London

by Longstretch on Sep 18, 2017
First Time

"You guys like the smell of salt air too?" "I do, but Mary is from Kansas City, so this is new to her." "Hi Mary. I'm Peter. And you're —" looking at the first girl. "Linda. I'm from Chicago." The student cruise around the world was sailing by the Statue of Liberty. Less than an hour into the four-month trip, I was trolling for a girl. The "Welcome Aboar...

Desires & Disorders Ch. 01

by PerilEyes on Aug 18, 2017
Fetish

I love Cyndi, I really do. When we hooked up a good five years ago, I knew she was the one. One of the things that drew me to her was how driven she was. Cyndi always knew what she wanted and always had a plan in mind. She took her professional life VERY seriously. When I met her in our final years of university, Cyndi knew that she wanted to take her histor...

The Diffident Muse

by Maccar on Sep 13, 2017
Erotic Couplings

Paula Tate sits reclined on the navy blue chaise lounge. Her legs are stretched out together in front of her, the left ankle just resting on the right, her hands loosely clasped across her stomach. Remaining perfectly still, only her hazel eyes move from time to time, scanning the room she has sat in so often before. It is a large, double-height space, with...

The Girl from the North Country

by Frankenstein1962 on Dec 9, 2019
Mature

It was a sad departure, but one that never the less had to be made. I was leaving the mental safety of a home and area that I had known for years. Lake Murray just outside of Columbia S.C. was always going to be a bittersweet memory. Too many good times to recount, but lately, a little more often than not, the bad memories outweighed the good ones. So, wit...

I'm Having Your Baby, Boy! Ch. 02

by dutchpantyraider on Mar 18, 2020
Group Sex

AUTHOR'S NOTE This story is entirely fiction. The category is group sex, but could just as well have been Exhibitionist & Voyeur. All depicted persons having sex are at least 18 years or over. Please note that the term 'girl' does not define the person being under age, but merely indicates her being a woman up to her mid-twenties. Enjoy your Literotica! --...

The Neighbors Ch. 01

by gsac305 on Oct 5, 2020
Group Sex

Wendy and Bill had moved into our complex about 6 months previously. They were a young couple that had moved from rural Oregon to the "big" city. Our town was certainly no major metropolis but compared to where they grew up it may as well have been New York City. Bill was 23 and managing a local auto parts store and taking some business classes online. Wendy...