Pencil Skirt Stories

117,393 results
Orientation
Length
Source
Infinite Scroll

Kinky Boots & Leather Suits Ch. 02

by mshsrfc on Sep 25, 2017
Fetish

Back to tonight, Dorothy went into the bathroom and had a quick flannel wash, making sure there was little steam, as her beehive hairstyle would fall. Once dry, she got dressed again in a bedroom bra and short corset, this was done as quickly as she could, but she was hampered by her 1” long nails, and she had to be very careful as Dave got so angry if she...

Nymphomania Clinic Ch. 03

by Rassendyll on Sep 14, 2017
BDSM

To recap: our hero is the male assistant in the State Nymphomania Clinic. Today he faces his hardest test. * The four of them gathered in Head Nurse Colferne's study. She in her uniform of tiny miniskirt, white high heeled shoes, white stockings exposing a foot of thigh, lace top pulled down to just above the nipples of her breasts. She tapped a pencil. H...

The Nerd Princess

by milkshake123 on Aug 19, 2017
Exhibitionist & Voyeur

This is a true story. A story I experienced it for myself. It's about my upskirt fetish and why I crazy about it. ***** I was 26 years old just graduate from master degree. Working everyday seemed hard enough for someone but for me it wasn't. I found a night program of in one university. I interested an applied for it. It was an exciting idea because this...

Student with Gill Ch. 02

by JohnRayn on Sep 12, 2017
Erotic Couplings

Me and Gill are in the kitchen cooking. I'm in my usual jeans and t-shirt combination while she is wearing one of my shirts over her white vest top and some tight jeans. It's all going well until I drop some pasta sauce on my t-shirt. "Oh, Jon, that's going to have to go in the wash now, take it off." "I've got messy hands though." "Ok, come here," I walk...

Train of Tempted Thoughts

by SandieQUK on Sep 14, 2017
Erotic Couplings

The first class diner car was less than half empty after the train crawled away from the station, emptied by commuters resigned to other forms of transport, but John remained. He knew he was going to be late but he had phoned ahead and been told 'as and when you arrive', and the Times crossword was as engrossing as ever so he welcomed the extra time. Over t...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Taking Care of Business

by CheekyCherry on Sep 12, 2017
Anal

It's hot and humid. You sit at work with your shirt halfway unbuttoned while your co-worker is detained with a slashed tire. I find my way to your room, slinking down the hall in my one-size-too-small grey pencil skirt and dark plum sky high heels and a low cut v-neck white tee. For a few moments, I stand in the doorway and watch a droplet of sweat roll down...

That Pesky Pencil Skirt

by wayneavl on Aug 24, 2020
Transgender & Crossdressers

That Pesky Pencil Skirt I consider myself bi sexual. Most people who call themselves bi actually prefers sex with one sex over the other. For me, it's all about the attraction. Male or female, it doesn't matter. On a recent Saturday morning, I was jogging through my neighborhood. I noticed one of my neighbors, about 5 doors down, standing at the back of he...

CEI Office Coffee!

by depositdutchess on Nov 22, 2017
BDSM

Jack was always late for work. He hated his Boss, the Big Bitch as he liked to call her, with big tits who wore tight pencil skirts. She always got what she wanted, especially from Jack, an average loser working a full time office job and catering to her needs all day. Jack knew if he was late again he was fucked. He usually stopped at Starbucks to get them...

Keeping a Job

by Secret_Passion2018 on Mar 27, 2018
BDSM

Jo knew she was in trouble from the tone of his voice when he called her into his office. She had been excited to get this job. After a few years out from work with her kids she was now excited to get back to it and had taken several secretary courses in an evening. She had been surprised to get this job - especially after how cold her boss had seemed durin...