First Time Sissy Stories

351,143 results
Orientation
Length
Source
Infinite Scroll

Fun with Cindi

by DougnCindi on Sep 14, 2017
Loving Wives

From our fist date I realized what a sexual woman Cindi was. We were both divorced and in our 30's so neither of us were hesitant about acting on our mutual attraction. Our first official date was a lunch in which we talked at length about how we had both seen each other before and always been attracted to each other. Two days later Cindi came to my house to...

A Correspondence with Sharon Ch. 26

by rivertown_rat on Sep 14, 2017
Letters & Transcripts

Part 26: It's Gang Bang time! This is the continuation of an email correspondence I had with a woman named Sharon Alderson. If you have not read the previous parts I suggest you go back and read from the beginning to get the full background. This conversation includes elements of wife swapping/sharing, incest, and group sex. If you don't approve of these be...

Wives of The Commander Ch. 04

by MTL17 on Nov 21, 2017
Celebrities & Fan Fiction

Disclaimer: I do not own The 100. I do not make any money from the writing of this story. ***** Raven Reyes found herself in a very familiar position, stuck in the middle of her wives. Sadly it was one of the few times that she wasn't getting fucked in the process, but that would come soon enough. And so would she, she thought with a smile. Which quickly...

Capri an Isle of Love

by walterio on Sep 16, 2017
Group Sex

INTRODUCTION This story contains sex involving heterosexuals, homosexuals, bi-sexuality and incest. It is a little bit long however it is based on true experiences and I believe you will find it worth reading. THE STORY I was in an Isle of Capri Hotel lying on my back with my hard cock buried in the pussy of a mature woman. She had my friend Paolo's cock...

The Making of a DomiNOT!

by dominot on Sep 17, 2017
BDSM

My husband wants to be dominated. By me. Well, it would be a scary prospect in itself, and it surely would break up a marriage or two. Mine is already breaking. We are hanging by a thread here. And one of our biggest problems is sex. Lack of it. I am a slut. Really. I am still, for all intents and purposes, a closeted sub. I had a medical fetish before...

Working for a Living Ch. 06

by call_me_dana on Sep 14, 2017
Transsexuals & Crossdressers

I slid out of the old Ford truck driver's side door. Surprisingly, my legs felt a bit shaky as my feet hit the concrete driveway of the Malibu mansion. I nervously straightened my cut-off shorts as I walked around the truck. She was waiting by the tailgate with a big smile on her face. "Wow Jaime! You are beautiful!" We had lost track after high school but I...

Married Guy New Experience Ch. 06

by Marriedandneedingmore on Sep 19, 2017
BDSM

This is the next part of my first story. I hope you have read the previous parts to understand how I have got to where I am now. In this part Olivia, my wife, is introduced so the story is from her side, also later Jim, my Master, is introduced. As usual I welcome any comments or suggestions. Still unsure what is the right category!! Up to now it has been...

Sara's First Pussy

by Inspirinious on Sep 14, 2017
Erotic Couplings

AUTHOR'S NOTE: While this is a work of fiction, it is largely based upon actual events. The names and some details have been changed to protect the identities of the people involved. +++++++++++++++++ KARLA: "Hey girl. How's you?" SARA: "I got big news." KARLA: "What?" SARA: "Last night I ate my first pussy!" KARLA: "WTF????" SARA: "I had my first, gi...

The Limousine

by [email protected] on Sep 16, 2017
Romance

Although Carla had been out with Joel several times, this was the first time he had been mysterious about where they were going. She had only known him for a few weeks, but already she knew he was someone special. As a matter of fact, she had just finished speaking with her best friend, MD, on the phone and told her just that. "When he is with me, he makes...

The Four Freshmen Ch. 01

by Jason_NYC on Sep 14, 2017
Exhibitionist & Voyeur

Part I: Donna They weren't exactly international supermodels. Mary, Patty, Barbara and Donna were Freshman roommates making the best of an overcrowded dorm. I met Donna at a mixer the first week of classes. Within an hour we were naked. Donna was eager and willing, but still very much a virgin. Some guys would have charged ahead. I couldn't. Not with a gi...