Naughty Story During My Sex Challenge Stories

357,318 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Stocking Sperm Challenge Ch. 02

by wordyone on May 7, 2019
Fetish

The second part of the story of the Stocking Sperm Challenge will make better sense if the reader is familiar with the original story. * Naturally, Ruby was enjoying telling April every saucy detail about what she had just put me through at my first and failed attempt at the Stocking Sperm Challenge and the history of my unsanctioned meddling with her inti...

Night Flight

by rockparker on Jun 1, 2020
Exhibitionist & Voyeur

Night Flight This story is a work of fiction based in fact. It is written for entertainment and the sexual enjoyment of the readers. All characters are 18 or over. Thank you, Mags, for your excellent proofing skills. You're the best! This story is dedicated to the young couple on Southwest Flight 1924. *** It had been an incredibly long week, and sudden...

Husband's Humped after Honeymoon

by nautius on Sep 12, 2017
BDSM

This is a sequel to the story "Husband's Humped on Honeymoon"; while this is a stand-alone story, you would appreciate it better if you read that story first, right here on literotica. Also, to respond to a common question that we've been asked -- Yes, this is all real, and not a figment of our imagination!!! *** It had been a really busy Friday at work,...

The Challenge

by bigtddybr on Sep 19, 2017
Loving Wives

This is an adult story about wife sharing. If you don't want to or don't like reading about such lifestyles, then I suggest you close this and move along to something else. This story is fictional, purely a fantasy. It is an adult story full of eroticism and sex. As it is my story, I choose the line of reasoning and scenarios involved. This is a fantasy an...

Fun on LIRR

by alexfun on Sep 17, 2017
Loving Wives

I shared a fun story here previously about a 24 hour overnight rail trip a few months ago. This was a much shorter trip but as much fun and in a way more erotic. This was about 6 years ago when we were living on Long Island and I was getting the LIRR into Manhattan 3 or 4 days a week, working the other days from home. Getting to the city for an early start...

Stocking Sperm Challenge

by wordyone on Jan 1, 2019
Fetish

My sister Dorene was on the phone asking me if I could accommodate her friend Ruby during the Summer holidays. "She's a really delightful woman, generous and easy going, I wouldn't ask you otherwise," said Dorene. Ruby was studying theatre and dance and had to attend a six-week contemporary dance course at the local university. I was certain that my girlf...

On the Job Story Challenge 2020

by Literotica on Jan 21, 2020
Loving Wives

It's back! It's the 2nd Annual On The Job Author Challenge Here's more from organizer HeyAll: It's one of the most common fantasies in the world. That co-worker you see everyday. Maybe your boss. Maybe your subordinate. Or you're out and about and you see someone diligently at work, or headed to work. The whole package is more exciting with their su...

My Exhibitionist Experience Ch. 03

by eksiber11 on Oct 6, 2020
Exhibitionist & Voyeur

Continuing from chapter 02, from all of my exhibitionism, my favorite from all of those activities is skinny dipping. I don't know how it started, it just this idea of swimming naked appeared in my mind and when I tried it once, that feeling of nothing attached to your body in a pool feels like freedom. My very first time of swimming naked happened when I o...

Debre's Swan Song

by The Swan on Sep 1, 2017
Group Sex

I first met Miki O’Malley in a creative writing course my junior year of college. She was everything I wasn’t. I was a quiet average looking female student who was not involved in any activities other than getting a degree. Miki was strikingly beautiful. She told me her name meant flower stalk in Japanese. Miki’s father was Irish and her mother Japanese. The...

The Tattoo Convention Ch. 01

by chloedeboncourt on Sep 13, 2017
BDSM

She was waiting bound to a pole. Her back was arched, her long black hair flowing over her shoulders and hiding her piercing green eyes. Her hands were handcuffed and tied to the pole at such a low level that she was forced to bow down. Her derriere was suspended in the air, held up by a silky linen wrapped tightly around her waist and fixed in the ceiling....