Upskirts Stories

51 results
Orientation
Length
Source
Infinite Scroll

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...

Donkey Boy William Ch. 09

by heavenlyKK on Sep 25, 2017
Exhibitionist & Voyeur

Jane came out of the bathroom clad in a white bra and yellow, patterned panties. "Come on, let's go," she said, looking into the mirror, applying the final touches to her hair. William stirred, but didn't move. "Come on, time to get up." Jane went over to the bed and threw the blanket off of him. "Holy cow, you are up...Woodie-alert!" William smiled. "How...

Who Wanna Be a Bimbo? Ch. 03

by mattpantyhose on Jul 4, 2018
Celebrities & Fan Fiction

This story is based on a game "Who Wanna Be a Bimbo" created by Dahakma. I would also like to thank one of my readers whose few ideas have been used in this episode. After the story was done I came up with an idea for an alternative route. Somewhere in the middle there is a fork on the road. The second version as well as the epilogue are at the end, after...

Academy of Sexual Studies Ch. 01

by daveball500 on Sep 13, 2017
Group Sex

As I took off my clothes behind the screens I wondered if it had been a good idea to turn up for the medical after all, I knew from the job application and the interview process that this post at the Academy would involve sexual situations, but there I was, not ten minutes after arriving being told to undress by my new boss who was barely half my age. AND M...

Belated Honeymoon Vacation

by rockpaperscissor8 on Sep 12, 2017
Loving Wives

Note: This is another on the same theme of cuckold stories where the husband is a cuckold perv and the wife takes things to her own liking. Sometimes I've been frustrated with comments made by anonymous commenters who just don't get the genre of cuckolding, inject their own conservative puritanical opinion and I have to ask myself, then why the heck are the...

Jane's New BFF Ch. 08

by heavenlyKK on Nov 25, 2017
Exhibitionist & Voyeur

They were in the retro dress shop - Jane, Arlene and Connie, because the trip to Japan was a business trip, and Donkey Productions would pay for a new wardrobe. "If you don't like it we'll go somewhere else," Jane said to Connie, who had expressed skepticism. But she saw a dress in her size that looked cute, so she decided to try it on, and all three of the...

Life of Koh Ch. 02

by heavenlyKK on Jun 9, 2020
Exhibitionist & Voyeur

In the span of forty-eight hours Koh had ten orgasms. Nine took place in the privacy of his new bedroom. The uncertainty of his situation was stressful for the young man, and he knew no better stress reducer than to think erotic thoughts and have his right hand tug on his pecker. Jane didn't seem to care whether he whacked or not and, unlike Marlow, she didn...

Life of Koh Ch. 04

by heavenlyKK on Jun 15, 2020
Exhibitionist & Voyeur

Three young men frolicked by the swimming pool. Sammy was one hundred percent straight, hetero all the way; he liked girls although, admittedly, he hadn't much experience with them. He was hoping though that this would change, now that he was in la la land. Jason was about ninety-eight percent straight. He liked females, but his brother was gay, so he wasn't...

Donkey Boy William Ch. 08

by heavenlyKK on Sep 25, 2017
Exhibitionist & Voyeur

Jane came out of the bathroom clad in a white bra and yellow, patterned panties. "Come on, let's go," she said, looking into the mirror, applying the final touches to her hair. William stirred, but didn't move. "Come on, time to get up." Jane went over to the bed and threw the blanket off of him. "Holy cow, you are up...Woodie-alert!" William smiled. "How...

Connie Takes Charge Ch. 03

by heavenlyKK on Dec 24, 2017
Exhibitionist & Voyeur

It was only four words, but to the recipient of the message it was as poignant and powerful as if it had been four thousand. Connie's marriage was just two weeks away, but the world didn't stop turning, William still woke with morning wood, and he still longed for the classy lady who aroused emotions in him he didn't know he had. He was consumed with her; h...