Pencil Skirt Stories

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The Bad Secretary

by Mr_Tamarind on Sep 14, 2017
Fetish

Linda had worked as my Personal Assistant for over a year now, I had thought myself exceptionally lucky when I first had her assigned to me and she had proved herself invaluable time and time again; not only was she bright, organised and very hard working but she had a fantastic memory for details. Within a couple of weeks of starting to work for me she had...

Jenna at Big Tit School Ch. 01

by siliconejelly on Sep 13, 2017
BDSM

Jenna was so hot. She needed to touch herself. Her tits were enourmous, like beach balls with very defined puffy areolas sitting out from her boobs like ping pong balls. But she was at Big Tit School, so she couldn't just stick her hands down her pants and fist fuck herself like she desperately wanted to. Big Tit School was not exactly school. Jenna was a...

The pencil.

by o2baPrince on Sep 24, 2019
Toys & Masturbation

I worked in an attorney’s office where three men shared a secretarial pool of three women. The men and secretaries would usually pair up and my team mate was in her early twenties, about 8 years younger than I. Being a very slow typist, I spent my day drafting letters in longhand to owners and subcontractors, submit them to my team mate who would type them u...

Booth Chronicles: Story of Desire

by SXY_Hot_Mamma on Sep 16, 2017
Novels and Novellas

You slide a dollar in, getting excited. You unzip your pants and pull them down, sitting back down on the stool. You slide another dollar in the machine, your heart starts pumping. The last time you saw her, she was amazing. It had been your birthday and a friend had gotten you into the bar as a present. She danced on the floor, shaking her ass in a school...

Her Doll Ch. 01

by WickedDoll on Sep 16, 2017
Transsexuals & Crossdressers

'What would you like, girls?' Quietly amused, I smiled at Samantha who eagerly gave our drink order as we settled into a corner booth at one of his favorite alternative lifestyle bars. Or should I say her. No difference. Sam was Samantha during the weekend and I was accepting of his chosen uniqueness. As long time friends, I knew it pleased him when he was...

Slut! Wife Needs a Hard Cock Ch. 06

by NeilMc123 on Sep 26, 2017
Loving Wives

I had decided to make contact with an ex-boyfriend called Steve. Steve and I were quite the item back in the day. Steve was the first guy I shaved my pussy for, the first guy to fuck my ass and the first guy to introduce me to the delights of lingerie and role play. He was blessed with a good 9 inches of hard veiny cock and boy did he know how to use it....

A Shameful Shopping Trip

by chrissiebee on Sep 12, 2017
Exhibitionist & Voyeur

Sir (as he likes to be known) messaged me and set me a little task to complete. Something very simple, but with a twist. Damn him but he knows me inside out and can tweak my every whim. All I had to do was dress and go out shopping - something I love to do - but this was shopping with a difference. Just thinking about it made me wet - and that was only in th...

Masturbating to a Woman in Heels

by Sexybeast8899 on Aug 28, 2018
Fetish

About two years ago I placed an ad on Craigslist. The ad was placed in the casual encounters section. The ad was asking if someone would let me masturbate in front of them. I asked in the ad that the woman be willing to wear high heels and let me look at their legs while I masturbate. I'm an attractive man. I'm about 6'1". I have a good body. I'm fit and I...

My Secretary with the Bald Pussy

by o2baPrince on Nov 7, 2017
First Time

I worked in an office where 3 guys shared a 3 woman secretarial pool. The guys couldn't type (I am very slow!) so I spent my day drafting letters to owners and subcontractors, they would get typed up and returned usually with a post it note about something that didn't make sense to them, and this went on for a year or two. So the guys and the secretaries usu...

I Dream of Revenge on My Bitch Boss

by Mr_Tamarind on Sep 2, 2017
Fetish

I was in the office, watching you every day, masturbating about you each night, wanking myself silently in the toilets at work, clenching my teeth as I made myself cum thinking about you strutting about in that tight pencil skirt with those amazing heels and how much I wanted you. You had used me and abused me for years now, forcing me to serve you in your o...