Babysitter Stockings Stories

43,783 results
Orientation
Length
Source
Infinite Scroll

Boi Toy

by Jamie_in_dresses on Sep 13, 2017
Transsexuals & Crossdressers

They met me off the train late in the afternoon. Their welcome was warm and friendly. I was exhausted from travelling and spent the evening in wonder as we first had drinks with friends of theirs at one home then all went out to eat at a restaurant, then back to another friends home for more drinks. It was a warm evening and the drinks I had, combined with t...

Bedroom Business Ch. 01

by Clansmansco on Sep 13, 2017
Erotic Couplings

After years of being a housewife and part-time nurse, my wife Julie got a job with a medical sales company and enjoyed a new lease of life! In her job she visits various businesses and uses her 'charms' to generate sales and her 'charms' certainly do help - only 37, a pretty face, sexy size 10, long dark hair, fantastic legs and naturally flirtatious, espec...

My Favourite Fantasy

by LauraJayne on Sep 2, 2017
Transsexuals & Crossdressers

God! I have so many as yet unfulfilled; it's difficult to know which one to pick. Do I go down and dirty here? Or do I choose something a little more commonplace? I am reluctant to share my favourite fantasy, partly because it is based on real events from my life as Laura and partly because it says something about me that I probably wouldn't want people to...

Mr. Plumber

by Notsurecurious on Sep 15, 2017
Transsexuals & Crossdressers

I was a little nervous; I couldn't wait for him to arrive so the waiting would be over. I had arrived a couple hours early, so I had time to get ready. I took a long hot shower, and shaved everywhere; my pits, legs, ass, around my cock, even my chest hair. I didn't have a hair on my body when I got done. I got out and moisturized all of my skin with a soften...

The Storage Bin Ch. 02

by gg9510 on Sep 16, 2017
Transsexuals & Crossdressers

I opened the door to Bob's truck. It was so big I had to carefully place my high heeled shoe on his side step to ease my entry into his cab. Once in there, I had to pull my skirt back down, as it had ridden up over the top of my stockings and garters. Finally, I sat back and as I did, I started saying, "I believe you have something for me?" I looked over a...

Tami Monroe Substitute Teacher

by 123z on Sep 17, 2017
Celebrities & Fan Fiction

Note- First in a proposed series with one of my favourite AVN inductees Tami Monroe as an former pornstar trying to earn an honest buck. ***** Tami Monroe paced the classroom with her cell phone clamped to her ear. "Come on Luke, pick up, pick up!" Her four inch heels clattered on the hard floor as she walked around her desk, her long mane of blonde curl...

The Employment Interview

by seeker666 on Sep 17, 2017
BDSM

He thought the interview had gone well so far. He really needed this job and knock on wood, he thought he'd done about as well as he ever had in a one on one interview. And this despite the fact that he had spent the entire time forcing himself not to check out the woman interviewing him. He had always been attracted to older women and truth be told, women...

Going Down?

by Fifi73 on Sep 25, 2017
Romance

Lucy woke up that morning all fresh, as she had been having a fantastic dream. She was being taken roughly by a stranger in the park near work without her consent, much to her delight. It had felt so realistic although it was just a dream as this faceless man had forced himself into her from behind, shoving her hard against one of the trees (which she passed...

Diary of a Cross-dresser Ch. 01

by Adikon79 on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on my own personal experiences and any comparison or similarity to anyone else's story, experiences, or copyrighted material is purely coincidental. This story contains adult material and language and should only be read by those legally permitted to do so. The story within is the copyrighted material of the author and should not be redis...

Babette in K-Town

by Babette_Boisjoli on Sep 16, 2017
Transsexuals & Crossdressers

I'm in an alley, on the west side of Chicago. There is no mattress or anything, but I have a towel to kneel on. My pimp is lining up men. They are lining up to fuck my face. They are looking at me, drinking, smoking, laughing. I can overhear comments about this "fuckin white ho" and "them nice big titties". They are right. I do look like a fucking whore. I...