Sissy Stockings Stories

45,315 results
Orientation
Length
Source
Infinite Scroll

A Dress Up Party with the Girls

by bigrusker on Sep 12, 2017
Group Sex

I stood there in the mirror, contemplating what I was about it do. Do you have what it takes to do this? I asked myself. At this point, it didn't really matter. I could hear the four giggling girls downstairs and despite only having arrived a few minutes ago I knew they had started the party quite a while ago and had already had a fair amount of wine. But t...

The Short Skirt

by babswalker on Sep 25, 2017
Mature

After my rather drunken night, I was a little apprehensive about going down to breakfast and seeing James the young waiter or Henri the barmen, with whom hubby Tom had shared me the previous night. All sorts of thoughts went through my mind - that it would be all over the hotel, that having had a bit of fun with an older woman they would treat me as a bit of...

Olivia's Revenge

by OliviaFantasy on Sep 13, 2017
Erotic Couplings

This is not a multi-part story but it might have a sequel if people thought it could. It is my first on literotica so I hope you like it. ***** Olivia sat down at her desk stunned. Moments before she had expected to be given a promotion and made director. But she watched her boss name Sharon to the job. She liked Sharon, she was nice enough. But Sharon was...

Consent Ch. 03-04

by sublocked on Sep 18, 2017
Transsexuals & Crossdressers

Author's Notes: (1) This is fiction. (2) Nonetheless, the pull of fantasies can be extreme. Never underestimate where it can take you. (3) These are broken characters. In the real world, one would be dead, the other in jail. (4) It is best to read chapters 1 and 2 to understand how Jack met Mistress Joan. (5) My apologies to those that want to get thei...

Replaying the Old Magic Ch. 02

by Learningfast on Sep 13, 2017
Fetish

The next few days and evenings were a whirl of feminine preparation for Josie. A new pair of shiny black shoes with 5-inch stiletto heels and new fully-fashioned stockings with beautiful seams. Trimming her pubic hair; waxing her legs and underarms at the salon; doing her hair differently; practice in applying new make-up; lacquering her finger and toe nails...

The Bartender

by mmmmassager on Sep 13, 2017
Erotic Couplings

The following is a running fantasy of mine that I wanted to see if I could put to words at my first attempt at erotic stories. A bit of feedback would be greatly appreciated. It is a little long winded, but I think it's worthwhile. The air was heavy and damp. The basement cellar of this old hotel was stifling in the heat, but the respite of the cool room...

I Remember Bethany Ch. 03

by rondori on Sep 16, 2017
Interracial Love

(In which Beth goes to the Brown Palace, samples foreign customs and has a trip around the world.) * My wife, Adele, had taken the girls back to St. Louis for Christmas with her Mother and I wisely worked my schedule so that I was the only rehab specialist available for the Holidays and I sadly could not go to visit my in laws. Since my wife was not home...

Workplace Witch

by GoldRogue on Nov 25, 2017
Mature

Jeff shook his head and muttered to himself as he drove behind the sedan with a fake bloody arm hanging out of the trunk, "Well it's almost over," he thought as some costumed co-workers ran laughing across the parking lot as freed autumn leaves blew in the breeze around them. He parked his car and grabbed his lunch bag, "Just have to get through this day and...

Waiting for My Turn

by RiverRhode on Jul 3, 2018
Loving Wives

I couldn't believe it had been just a few months earlier that I first revealed to my wife that I really wanted to watch her have sex with another man. It's not like we had never talked about it. I mean, we had even had a threesome with a gay friend of ours years earlier, but that was really more for me than it was for her, even if she had a good time, too. I...

Conquring Jules Pt. 05

by Longe on Nov 1, 2017
Mature

My mind was still replaying Jules milking my prostate when I woke the following morning. Since I came harder than I ever remember, I decided she could do it anytime she wanted. I needed to make sure she knew the only thing going in my ass would be her well lubed finger. I dressed and prepared to head out to the gym. When I stepped into our kitchen, I was su...