Jacking Off Stories

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Orientation
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Infinite Scroll

My First Transsexual

by iser21 on Sep 16, 2017
Transsexuals & Crossdressers

When did it all start. After the first few times with my best friend (Ed), I thought I would try another guy. That went well. By the time I was in my second year of college I knew I was Bi. Being Bi, I think is better then being just gay. You can have men or women. I had had about 6 different guys in college. And about 5 woman. They all knew I was Bi. By my...

Giantess on the Subway Ch. 02

by kathryn94 on Dec 25, 2017
Fetish

Jake stared up at her towering figure in disbelief. He didn't know what to do. She extended her left arm out. Just before she managed to grab him, he ducked away. "You can't just run away. I haven't had enough fun yet." She said, walking towards him. He continued backing up. She began to get impatient and moved towards him more quickly. Her throbbing cock n...

Caught at a Peep Show Ch. 01

by Anal Slave on Sep 13, 2017
Fetish

It was a Friday night and I got home and cleaned up. I was going to a new XXX booth/ peepshow in town. My wife asked me where I was going and I told her I was going to play poker with the guys. I jumped in the car and drove off, I pulled into the parking lot and sat in the car for a minute and looked around. I looked in the side mirror and saw my wife pull...

Peeping by the Pool

by Boxlicker101 on Sep 11, 2017
Exhibitionist & Voyeur

After dropping out of high school at the age of 18, Ryan had nothing better to do than hang out, peeping through the fence that separated his families property from the neighbor's back yard. The best thing about peeping was the neighbor herself, a tall, voluptuous woman in her forties. He knew her name was Marian and she was divorced, lived by herself in the...

How I Finally Opened Up

by WayneGibbous on Sep 14, 2017
Loving Wives

Chapter 1 John and I have been married seventeen years and they've been, I think, better than average. We certainly have loved each other and gotten along quite well. There have been adjustments and points where we disagree, like in every marriage, I'm sure, but we've generally worked through them. One long-standing difference was sex. Now, before you thin...

A Study Session Gone Wrong Ch. 02

by author522 on Sep 16, 2017
Fetish

I woke up Saturday morning and knew instantly that I had no choice but to go back to Shelby's house. I couldn't risk the humiliation the video and pictures would bring, and Shelby could complain, saying I refused to help with the project. So I treated the day normally and then left for Shelby's house a little before two. When I got there, Melissa opened the...

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...

Mavis Dracula Returns to Glory

by BuffysInsta on Dec 9, 2019
Celebrities & Fan Fiction

Hey Diary. It's me, Mavis again. Just wanted to record my second glory hole experience because I had so much fun last time! So, let's get to it. I arrived at the glory hole shortly after 11 p.m. I was dressed in a slight black dress with black shoes and white socks. I had on white panties and a little necklace that dropped down to my cleavage. I wasn't hidi...

Jim and Micki: A Love Affair Pt. 02

by luvdr on Aug 31, 2017
Group Sex

Micki whispered in Jim's ear, "Jim, do you want to fuck my ass?" When she offered me her tight little ass, my cock immediately began to stiffen. I took Micki by the hand and lead her to the big chair next to the sofa, where Bill her husband was eating my wife Kay. Kay was sitting on Bill's face and jacking his dick, licking and sucking between moans of ecs...

AdDICKed Cuck Ch. 02

by Anal Slave on Sep 11, 2017
Fetish

Linda my mother-in-law came out of the closet. Her pussy soaking wet, she reached over and grabbed the strap-on dildo. She put it on and told her daughter to get up on the bed in doggie position. My wife obeyed and Linda mounted her from behind and fucked her like a champ. I am watching my wife getting fucked by her mother with a strap-on. I'm jacking my co...