Highheels Stories

39 results
Orientation
Length
Source
Infinite Scroll

A Weekend in the Big Apple

by Spankx on Sep 1, 2017
Group Sex

It was my first trip to New York. I had heard all about how small-town girls like me should be very careful if they ventured into the Big Apple. But I was ready for anything. When I say everything, I mean absolutely everything. I was looking for a wild sexual encounter. I had been fantasizing for months about slipping away for an erotic weekend. My boyfrien...

Burning Bridges

by sereneone4u on Sep 14, 2017
Erotic Couplings

I am wearing a black wrap dress and have on black highheels, matching panties and bra...all black. I have on a long strand of Mikimoto pearls and matching stud earrings...I wore my auburn hair down and my lips are Chanel Red. You have on slacks and a long sleeved dress shirt, shiny dress shoes and a long coat...it is Autumn, my favorite season and the air i...

Closing Time

by spandexman on Sep 13, 2017
Fetish

It was a better than average day at the Riding Shop, but it was Black Friday. The store had been on Main Street for nine months and had barely hung on. In spite of being a small city not far from a few horse farms and the country club where there were horse stables and riding lessons for teenagers, the store that specialized in riding boots, jodhpurs, breech...

Stella

by spandexman on Sep 13, 2017
Fetish

When I was a kid my best friend Tony's mother was the woman of my erotic dreams! Stella Winters was a 5'7", Barbie doll faced gorgeous, MILF, with big almond shaped hazel-green eyes, thick just below her shoulders curly fiery-red hair, and a very overripe 36HH-24-38 hourglass figure that everyone in town took notice of. Since my parents were friendly with th...

Watch Me Play with Myself

by DarkScorpio666 on Dec 13, 2017
Exhibitionist & Voyeur

He booked the room, but I made the rules. Before we met up, I made sure that he would be tied down to a chair in the corner of the room. He got to watch, and I got to play. I came out of the shower and got dressed in a sexy white lace bra and panty set that hugged all the right curves, exposing lots but gently hiding some spots as well. I took off the blin...

Das erste Mal...Reizstrom

by Kassert5 on Sep 17, 2017
BDSM

Meine erste Geschichte, daher seid bitte etwas nachsichtig ;) Kleiner Hinweis: Reizstrom ist kein Spielzeug, falls so etwas für derartige Praktiken angewandt wird, unbedingt bezüglich der Sicherheitshinweise informieren!!! Und nun viel Spaß beim Lesen. Wir befinden uns im Schlafzimmer. Ich habe Dir befohlen, Dich nackt auszuziehen, und mit geschlossenen A...

Biker Bitch Ch. 09

by MicheleNylons on Jan 6, 2018
Transsexuals & Crossdressers

Chapter Nine: Fuck the Trans Cooze! Cassie sat behind a desk in a stark interview room at the Los Angeles County Jail. ATF do not have their own detention facilities; they use Federal penitentiaries and often borrow local law enforcement facilities to temporally incarcerate suspects and interrogate them. She had been freed of her cuffs and her clutch purs...

Biker Bitch Ch. 03

by MicheleNylons on Dec 25, 2017
Transsexuals & Crossdressers

Chapter Three: Super Glide Natalie Styles wore her usual uniform of tight-fitting navy blue business suit, cream silk blouse, heavy black mascara, bright-red lipstick, ultra-sheer pantyhose and Christian Louboutin high heels. "So here's the deal. We've made you into half a girl. You have the tits. The rest comes later if you cooperate and get us what we wa...

Biker Bitch Ch. 02

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter Two: Caught With Consequences Cameron Rivers' first memory of feeling different to everyone else was when he was eight years old. The other boys liked to play with bikes and toy trucks and toy cars but he much preferred his younger sister's Barbie. But even then he was smart enough not to say so. He used the excuse that he had to play with her becau...

Finishing School For Ladies Ch. 05

by MicheleNylons on Oct 9, 2017
Transsexuals & Crossdressers

Chapter Five - Revenge Is Mine The following weekend was Easter and the school was closing for the four day holiday. On the Wednesday night Emily and Valerie slept together in Valerie's room. Emily locked her door and put a do not disturb sign on the doorknob and padded across to Valerie's room and locked the door behind her. The girls slept in satin knick...