Caught Jacking Off Stories

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80-year-old Neighbor Ch. 05

by shoguy on Sep 19, 2017
Mature

On the bed, curled up in a ball and now drinking a bottle of scotch straight from the bottle, Brad could not believe what he had just heard from his wife and that was that she had also fucked his own father. "Oh god, I knew that you could see right through me," I groaned as he stretched me out and tunneled into me. "I like how naughty you really are Sara,"...

Keeping Score

by KathyRobert on Sep 11, 2017
Loving Wives

When my wife, Kathy, and I were dating there was a thing going on called 'One Upmanship.' The idea was that if you could outsmart or embarrass someone, you were 'one up' on them. I haven't heard the term in a long time, but back then Kathy and I made a game of it and even kept score. At first I was way ahead... "I went on a date last night." "What?" No way...

Maid's Help

by strokin31301 on Sep 12, 2017
Exhibitionist & Voyeur

Let me start by saying how much I love to jack off, but not just jack off but to get caught doing and being humiliated is such a turn on for me. So as I check into a room at a local hotel I asked for a ground floor one so I could start my plan on getting caught. First I wrote a note to put on the outside of my door saying "Be Right Back" and taped it just a...

James Just Turned 18

by IJustMight31312 on May 11, 2020
Mature

I was next door with Brenda getting things ready for her son James's 18th birthday party. The family had lived next door for five years and their son was the age of my youngest. They had become friends and both Brenda and her husband Chris had become friends of mine. Brenda was especially excited to be moving James to the bonus room over the garage. This wo...

Spite Sex Ch. 01

by Stoney Beach on Sep 1, 2017
Exhibitionist & Voyeur

I'd been going to Hippie Hollow for some time, and I'd seen a lot of different things happen. Most of the things in this story happened in the past, the park has changed, and I don't feel it would be something you'd be anywhere nearly as likely to see today. I really liked the situations where I was able to get involved or at least watch the goings on. But l...

Old & Divorced

by Jaywesal on Sep 1, 2017
Group Sex

Sometimes life really sucks! Fifty-four years old, married thirty years, and then zap! It’s all over. My wife, now ex-wife, decides that she wants someone younger, fifteen fucking years younger. As I mentioned I’m fifty-four; bald; salt and pepper beard (as well as my chest and around my dick); six-foot and about one sixty-five in weight. I’m still in pretty...

Our Masturbation Adventures Ch. 1

by KathyStroke on Sep 25, 2017
Exhibitionist & Voyeur

My name is Heather, I’m 23. I’m involved with a much older man. His name is David and he just turned 47. David is a pilot for a major airline - a DC10 captain. I have been seeing David for about six months. What I love about David is that he is such a pervert! Some would consider our relationship is pretty strange. We don’t fuck, we masturbate. Oh, I have f...

Jack's Diary Confessions Pt. 01

by justsomeusername on Jan 20, 2020
First Time

This story is fictional. This story contains strong language but isn't meant to offend anyone. I intend to make this into a series and possibly write a similar story about another character. Enjoy! * 3.1.2020 20.08 Diary. I turned 18 today. I didn't have a big party or anything just ate some cake my mom had made the night before and caught a movie with m...

First Pt. 02 of 03

by sex4every1 on Jan 22, 2019
First Time

Thanks to Iris_Untangled for editing. You're amazing! ***** That Friday night, Amber picked me up at my place. As soon as I laid eyes on her, I was a goner; my cock was an iron bar before I had even said hello. She wore a short, black dress, sleeveless with a sultry open back, and black suede lace-up heels. My god, she looked hot! Although she was a bit e...

One Adult Video Store

by Rigid1 on Jan 16, 2019
Loving Wives

This whole event started rather innocently. My wife had called me to say her and Sherri had been shopping and were hungry so they were stopping to grab a bite and they asked me if I wanted to join them. Surprisingly they had grown to be best buds through all of this and I could not have been happier. I had clearly benefited from this friendship and the girl...