Caught Jacking Off Stories

338,674 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

The Handjob From My Roommate

by Canicumonyoubaby on Sep 25, 2017
Erotic Couplings

I was feeling horny today. It had been awhile since I last jacked off. I had just taken a shower, and while I was washing my dick, I began thinking of my ex-girlfriend. I was remembering how sexy she was, how perfectly my dick felt in her pussy, and how warm & wet it was. I remembered how I used to cum in her mouth and on her face so often, and how much it...

She's Gonna Tell My Wife Ch. 01

by w14apweal on Sep 13, 2017
Exhibitionist & Voyeur

My name is Chris. I am a happily married man. I have a gorgeous wife. Her name is Sherry, we have a great sex life and couldn't ask for more. Well, actually... I COULD ask for more. See, my wife was a virgin when we married and she is not very adventurous or interested in new things. She raves about my abilities in bed and says I completely fulfill her. I kn...

She's Watching...

by mlsdog on Sep 12, 2017
Exhibitionist & Voyeur

OK... About 99 years ago...well more like 20 years ago I dated and later lived with a wonderfully sexy woman named Joanne. In retrospect she had to be the most sexual woman I have ever been with. Truly a great appetite for passion and genuine sense of adventure sexually speaking. One night she comes home after parting with her girlfriends and having a cute...

Exploring

by softride on Sep 14, 2017
First Time

Many years ago, way before the internet, near the end of high school a new kid, Tony, moved in just down the street from me. We had both already turned 18 - I had been held back a year due to illness when I was little and he because his father had worked oversees and schools couldn't figure out what grade he should go into. We quickly became friends, though...

The Knot Hole

by toddystime on Sep 16, 2017
Exhibitionist & Voyeur

Pearl was masturbating again. I'd watched her do it so many times that I knew from the way her fingers moved that she was close to an orgasm. I had a lot of pictures of her on that towel draped lounge chair— diddling herself as her husband did yard work around her. Pearl didn't seem to care he was there, even making him stop to fetch water or something fro...

Could It Happen Again?

by mumblegooseegg on Sep 17, 2017
Loving Wives

This story is dedicated to those readers who liked "It Has Only Happened Once," a previous story of mine, and especially those who documented their positive feedback: RyeandGingerAyle, bruce22, johnnyjay85, HappyWife85, Grayhair61 and Bill (via email). Thank you, all of you! Here is a happy sequel to the saddish ending to that story, with my wife Linda losin...

Camping with Chris

by FunKelly on Aug 18, 2017
First Time

This is about my first time with Chris. This was the summer after my senior year of high school. Bored with our summer jobs, my best friend Billy and I decided to go camping one weekend. By the time Saturday rolled around, the number had grown to 6 guys. Saturday afternoon, we loaded up our tents and sleeping bags and went out to some property my parents had...

Punished for Jacking Off

by Anal Slave on Sep 12, 2017
Fetish

It all started one morning when my wife came home early from work and caught me jacking off. She had stood at the door watching me stroke my cock and playing with my balls, I don't know how long she had been standing there. All I know is that I had just shot off a load of cum and was licking it off my hand when I noticed her standing there. To my surprise s...

Introducing my Wife

by movie_fan1969 on Jan 5, 2018
Loving Wives

As my wife and I were fooling around last night, I asked her if she would answer a naughty question. We really get off when we "talk dirty". She was jacking my cock while using one of her vibrators on it. It feels really good when she holds the vibrator on the underside of my head while she slowly masturbates the shaft. We were high (hey, we live in a sta...

Mom's Friend Margie

by mustanger7up on Sep 12, 2017
Mature

I’ve known Margie White and her family since I was 4, she has been my mother’s best friend forever it seems. I had a crush on her that wouldn’t end, she has great big tits and a large ass, and it doesn’t even bother me that her belly bulged out. She always had a smile for me and on open ear to listen to anything I had to say. I would go over to her house to...