Mature Women First Time Wearing Stockings Stories

353,852 results
Orientation
Length
Source
Infinite Scroll

Connie

by csmsmith on Aug 19, 2017
Exhibitionist & Voyeur

My name is Connie. Bob was the man that took my cherry when I was 17 and in High School. That happened in the back seat of his Father's car out by the lake. I had been out with a few boys before Bob but none of them got too far with me. My first real puppy love, though, was Terry. I let him play with my sweet young breasts and he was the first boy to touch...

A Joyful Irony

by trigudis on Oct 31, 2018
Romance

Life is full of the unforeseen—twists and turns and ironies that crop up when we least expect it. What happened to me recently underscores the point. First, let me take you back, way back to the late fall of 1965 at a place called the Baltimore Civic Center and a rock group called the Rolling Stones. The Stones were on their second American tour that Novemb...

Together, Forever! Ch. 03

by simply_cyn on Sep 16, 2017
Mature

It turned out that Colin was everything Victoria had hoped and more. He was warm, very approachable, a flirt and every bit as handsome as he was on film, even more so. He looked a lot younger than his age of twenty-three, probably around nineteen or twenty. She was still a little concerned about how he treated the young girl he had been talking to before Vic...

Walking my Dog Ch. 02

by MaeWestFan on Sep 13, 2017
Loving Wives

You can always count on Bob to be on schedule. Sunday afternoon 3 o'clock he was kissing me goodbye. 3:05, I was in a scented bubble bath shaving my legs, with a glass of white Zinfandel at hand. Like a young girl preparing for her date with the captain of the football team. Everything had to be perfect. Once out and dried, putting on a thigh length lace che...

Unforeseen Changes Pt. 01

by adler666 on Jul 9, 2019
Sci-Fi & Fantasy

How a Couple found their Inner Selves Our story is just beginning, but already involves a lot of surprises. It does involve magic of alien technology and wishes, finding the real you, even if that state isn't what you thought it was. ******************* It all started like a typical fall Saturday morning. We had cruised out from our city neighborhood to...

Professor Choi

by wanting2bfreed on Aug 6, 2019
First Time

This is purely fiction any correlation to real people is completely happenstance. Warning This story contains depictions of coerced male on male oral intercourse. The misquote Austin Powers if this is not your bag baby, do not read it. It was a warm early spring Friday. I was attending a math class in my third semester at a prestigious private western Univ...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

Graduation Present

by Cram213 on Jul 2, 2019
First Time

My name is Marc, and I had just graduated high school without having ever done anything with a member of the opposite sex. And not for a lack of desire -- I was 100% straight and just as horny as the next 18-year old male, but more a victim of circumstance. I had been kind of quiet and self-conscious in middle school, and thus had never really built any lon...

The "Dresssmaker"

by Classygloves on Sep 18, 2017
Transsexuals & Crossdressers

I was all excited. The emerald green satin evening gown that I had purchased on Bay was just delivered. I had been planning for months to dress up and attend the gala ball at Fantasia Fair, an event held every year at Provincetown, Massachusetts for transgendered persons and cross dressers. I nervously opened the package and hurriedly undressed to try on thi...

Role Playing is Such "Hard" Work

by statestreet on Sep 13, 2017
Erotic Couplings

My partner and I often enhance sex through role-playing. Sometimes one of us has a fantasy that just has to be satisfied and other times we'll kind of fall into a "game" and see where it leads. Both of us enjoy acting out our roles, especially when they are opposite to our normal personalities. I am a senior executive for a large candy company. Last week we...