Up Skirt Stories

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Orientation
Length
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Infinite Scroll

Magic Dress Pt. 03

by SlightlyRude on Feb 11, 2019
Transgender & Crossdressers

I had been wearing dresses at home for quite a while now, with my wife's encouragement. The first one I tried was very special and we called it The Dress. It just made me happy. On Wednesdays I was sucked off while wearing it. On Fridays I dress up as Sexy Sally and fuck her. On Saturdays, for her entertainment not mine, she would dress me in various outfits...

A Birthday Present Goes Awry

by sexygirl76 on Sep 13, 2017
Group Sex

28 year old Anthony was led by the guard to the visitor's room. He knew he had a visitor but didn't know who it was. Since it was his birthday, he figured it was probably his parents. For the past five years he had been behind bars for a crime he didn't remember committing, and his parents always threw him a party on his birthday. Anthony was spending 15 ye...

The Dressing Room

by Sean Matthews on Sep 14, 2017
Exhibitionist & Voyeur

"Dammit. I am going to get Sean to notice me!" With that thought, Sara launched her plan to seduce her extremely shy co-worker. They met while working at a major department store. She had been eyeing the security guard as he made his rounds past her station in the lingerie department. While he would make polite conversation, her attempts to move the convers...

Finishing School - Staff - Mr. & Mrs. Ellis

by DonBrown on Jul 3, 2018
BDSM

Welcome back to Calder House, the place Ladies are finished and below stair girls are whipped into service. The staff are also dealt with harshly should they step out of line by Mr. and Mrs. Broadwood who ruled the staff as well as the inmates with the strap. The only difference was the staff were whipped in private for any indiscreet actions, private bei...

Neighborhood Survey

by wishful1 on Sep 12, 2017
Erotic Couplings

9:30 a.m. My third day home, on vacation, nowhere to go. Dressed in sweat pants and tee shirt and nothing else. Nearly a month since the last time I fucked and wondering who I could call and see. The doorbell rings. I open it. It's a girl. Actually, it's a young woman with a brief case and a clipboard. She's in her early twenties, I guess. She stands about f...

Marilyn's Family Values

by BrettLynn on Sep 12, 2017
Transsexuals & Crossdressers

Here's the third part out of my bizarre mind. Now we get to learn a bit more about our heroine Marilyn. Plus, there's still the requisite sex and a little bit of intrigue thrown into the mix. Plus, this won't come out as rushed as the last two...I hope. My damn background as an editorial writer rushing to meet deadlines is, albeit slightly, mucking up my wor...

Nightshift at Judy's Ch. 1

by Dancing Sprite on Sep 12, 2017
Anal

"You won't do it!" Wendy said, convinced that he was bluffing. Dave glanced over his shoulder to make sure the only customer in Judy's SuperBurgers was really the person he thought she was. "Yes, I will!" he assured her, grinning from ear to ear. "No way!" Wendy insisted. "Sure I'll do it!" "Then what are you waiting for?" "Let her finish her meal. It w...

A Look in the Mirror

by smithjon1919 on Sep 18, 2017
Anal

Phoenix summers feel as though they were meant to set the skin on fire, so it only made sense to drink one cold beer after another while we sat outside on our hotel patio. I was away on training for a two week stint, so my wife decided to come out for a visit over the weekend that divided my training weeks. The banter in conversation was typical of colleagu...

Pam and Mark

by markledeux on Apr 10, 2018
Loving Wives

Let me tell you about some marvellous adventures I had with a boyfriend of mine about 12 years ago. But first, a bit about me. Well, me as I was then. I was married (not anymore, I won't bore you with that story here), 5'6", slim, dark, brown eyes, long dark tightly curled hair, slim face with big brown eyes and a prominent narrow sexy nose. I have small b...

Detention

by jansen_jan on Dec 16, 2017
Mature

This is a fucking nightmare... I am supposed to concentrate during class, and here's this woman prancing around the room in a pencil skirt and stockings. My high school days had gone by without much trouble until a few weeks ago. I had a best buddy, there was a girl having the hots for me ... Good grades, et cetera On the day our economy teacher Mr Stockton...