Upskirt Stories

348 results
Orientation
Length
Source
Infinite Scroll

Conversations 04

by SleeperyJim on Apr 23, 2019
Loving Wives

This work is copyright to the author. All characters are over 18 -- and even if they look younger, they are way over 18. Like 25. I'm writing a series of short stories on the same theme -- that conversation between a man and wife when one of them has been caught cheating. How it turns out kinda depends on my mood at the time of writing. Sometimes they are f...

Onsen Onna (Hot Spring Lady)

by dior11 on Sep 26, 2017
Fetish

Part I – the meeting Onsen bathing is one of the highlights of any trip to Japan. Add meeting an intriguing woman for a memorable experience! There are onsen (hot springs) everywhere in Japan, literally hundreds of places with naturally heated water that comfort millions of Japanese who go on meccas for the best onsenburo (hot spring bath) experiences. Wee...

Senior Tour

by dispatcher59 on Sep 19, 2017
Mature

Susie was the ideal tour director-always cheerful, always on top of things, and cute as a button. Slender with light brown frosted hair, I guessed she was in her early 50's. She was friendly, always with a hand on your arm as she talked to you, though not overtly flirty. She was the coordinator for our local bank's travel group, a group that catered primaril...

The Trade Show Pt. 08: Boobs First

by GeorgiaD on Oct 7, 2019
Transgender & Crossdressers

I welcome feedback so please, if you would like to comment, feel free. Be kind though! ***** As I rode Cindy's shaft, enjoying varying my position to both enhance her and my own feelings, my mind drifted, dreaming of what lay ahead for Georgia, and how I would handle transitioning at work. Immediately, of course, doubts crept in and I was jolted back to r...

Sex-Ed for Dummies - Lesson 05

by Slyguy1313 on Apr 17, 2019
Celebrities & Fan Fiction

Disclaimer: This is a work of fiction. It is not real! It did not/will not happen in real life and should not be mistaken as such. Lesson #5: Anal Starring Bryce Dallas Howard & Camila Cabello Codes: Cons, MF, MFF, Anal, Masturbation, Oral ***** "Hello and welcome back to another episode of Sex-Ed For Dummies!" The announcer yelled, his voice deep and...

Roommate's Girlfriend

by FolleLeone on Mar 2, 2020
Group Sex

Mark was my roommate for one year in college. We didn't get along well. Nothing bad, but our personalities just didn't mesh. Tonight he had his new girlfriend, Kate, over, though I hadn't seen her as I was in bed trying to sleep. I'm not great at falling asleep. It often takes me an hour or more, so if I got up to greet her or anything like that, I'd be up f...

The Red Bracelet

by MrIllusion on Sep 14, 2017
Exhibitionist & Voyeur

Note: this is a somewhat long and slowly developing story. Everything started when I woke up on a later autumn day with a strange idea in my head. Well actually it started the first time I saw Bianca a couple of years ago, when she was a work colleague of my then girlfriend. I met her a few times at work parties and even though I quickly noticed that she w...

Customer Friendly Ch. 03

by dispatcher59 on May 22, 2018
Mature

Susie and I continued to see each other, though our meetings were sporadic, as she was busy running the dealership, and of course, she had to work our time together around her husband. She would come by when she was heading to my area or beyond, and we'd get together for what was usually a mid day rendezvous. Most of the time, I'd fuck her with a condom, sin...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Jane's New BFF Ch. 05

by heavenlyKK on Nov 25, 2017
Exhibitionist & Voyeur

"I still don't know why you didn't have me play the swim coach," Pete said. "I would have been perfect for the role." "Well Pete, it's like this," replied Jane, "the swim coach is gonna get a Japanese dick rammed up his ass." Jane was on her own for this video, and she was feeling the heat. Monica was still on holiday, although she texted to say she'd be...