Upskirt Stories

348 results
Orientation
Length
Source
Infinite Scroll

Braddock's Tavern

by johnnieblue44 on Sep 14, 2017
Erotic Couplings

It's frustrating working with a co-worker that you're just dying to fuck, especially when your own girlfriend works for the same company, too. Fortunately, Steph Jenkins came up with a creative way of circumventing some sticky issues, and my cock and I remain forever grateful. This true story, from many years ago, is a way of expressing such gratitude. Bette...

E.D. Donahey: Legs War Ch. 3

by Foxfan69 on Sep 16, 2017
Celebrities & Fan Fiction

As I stood in front of the two beautiful, sexy, blondes; my mind was in a whirl. I could not believe that my wildest sexual fantasy was about to come true. Here I was; buck naked; in front of E. D. Donahey and Dr. Georgia Whitkin. My rigid cock was at attention; ready for action. "Are you ready to begin, Greg?" E.D. asked me this as she and the lovely Dr. W...

Dining at the Y

by JRob on Sep 13, 2017
Loving Wives

My wife Jennifer works at a local hospital as a nurse. The pressure is high and the days long as the hospital has suffered through some cutbacks. Every so often the nurses, mostly women, break the tension with a little naughty talk. Out of the ears of the supervisor and the patients, of course, but little digs about their love life or midnight escapades. S...

My Golf Exhibition(ism)

by HarleyFatboy1 on Sep 14, 2017
Illustrated

We still had young children at home, which greatly inhibited my ability to show off. I was in my early 30's and had that female in her 30's mentality of wanting to show that I still had it. (I guess being in my early 40's hasn't changed this mentality one bit. In fact, I may be getting worse.) We had an older neighbor who would spend her summer weekends in...

Robin's Birthday Celebration day Pt. 02

by MKarpenter on Feb 4, 2020
Transgender & Crossdressers

I felt a strange sensation as I began to woke up. It wasn't a hangover from all that tequila from last night this was instead a great feeling that no other morning has given me. Morning's sunshine had pierced through the window and illuminated the hotel room. All I could see was a blur of colours as my eyes took a while to adjust what I was seeing. The pictu...

My Girlfriend Wants to Build a Harem

by CandidBandit on Dec 7, 2017
Romance

It was a Sunday evening during winter break. A light dusting of snow was falling outside the window, while inside a heater was keeping the group warm and toasty. A soft murmuring could be heard as a quiet conversation was taking place. Maeda Hiroshi was laying on the room's sole bed, quietly thinking to himself. He felt very warm and relaxed despite the cold...

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Care for a Game of Pool?

by Shinzon on Sep 14, 2017
Erotic Couplings

"How about a game of nine-ball?" Justin asked. Melanie didn't particularly care about playing pool; however, Justin's invitation was simply too good to pass up. In her mischievous mind, it presented the perfect opportunity to tease. Teasing was something she thoroughly enjoyed, and she especially loved it when her actions caused him to cross the line. A d...

Abducted Ch. 02

by HarleyFatboy1 on Sep 12, 2017
Chain Stories

Chapter 2 -- The Handling of Elizabeth It was business, but this part of it was quite pleasant business. I take the ends of the length of rope. I hold them together, and straighten out the rope, until it has a loop in the middle. I pull the loose ends through the loop, forming a kind of slipknot. The slipknot goes around both of her ankles. I pull the kno...

Cancelled Date Night Ch. 03

by kinglem on Sep 16, 2017
Transsexuals & Crossdressers

Sarah's tongue made sensuous swirls around Dave's mouth while Colleen's did something similar around his cock. Dave was in heaven, a few negging doubts about Collen still crept around his mind but he had never experienced such pleasure so he didn't linger too long on them. Sarah seemed to sense he was getting close to finishing before he realised himself....

Sticking to the Script

by LaurelAspen on Apr 9, 2019
BDSM

Trudy sits at a high stool, enjoying the view across the Thames towards St Pauls. Self-consciously tugs down her skirt; not a night-clubbing out on the pull mini, but shorter than usual. Dangles a shoe in manner guaranteed to set any foot fetishist's pulse racing; what appear to be hyper-expensive Louboutins are in reality 30 quid knock-offs from a Walthamst...