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Stories | 2016

Lesson Review w/ my Sex Ed Teacher (m/F)

Background: I have always had an interest in older women, but it wasn't until I turned 18 that I felt like I could pursue my fantasies. At my school there is a program where Seniors can assistant teach a health class to Sophomores. It counted as a gym class and it was good for college so I decided why not. I was assigned a teacher who was fairly new at teaching health, she was the school's dance teacher and thought that it would be fun to teach health too. She was about 5' 6" with black hair and was about 48.

A [m]id week a[f]fair

We met for lunch in a dark, Italian restaurant, tucked away in a booth in the back. We killed a bottle of cabernet and picked at our food. Too busy talking about our frustrations, wondering how we got here. How our marriages disintegrated to glorified roommates. We laughed and flirted as if we were teenagers, as if the real world didn't exist beyond the front door. We basked in the unfamiliar feeling of being desired.

Then he asked, "Where to next?"

A [F]riend of a friends [M]other.

Found this subreddit about a week ago and once I did, I knew I had to sign up to tell some of my stories. First a little about me. Names Jake, I'm 27, 6"1' and just as guys like to say to make it sound like we're not the conceded bastards we really are, "I've been told that I'm a pretty good looking guy" I love it when people say that, it's like they're saying Am I handsome? I don't know. I'm just repeating what other people say.

Getting rough

Moved from /sex A little preface before my experience I'm a 19M in college have been with about 10 girls most have only been 1 nighters as I really don't have an interest in any more after being hurt in my first and only relationship while in highschool by my girlfriend of around 1 year. I lost my virginity to this girl and she was my first for just about everything except kissing, but alas this post is not about her as she is not deserving of a post. Who is deserving is the girl I met last week.

(M)y business (t)rip surprise

This happened not long ago on a quick business trip one state over. I was developing a contract with a vendor in Woonsocket RI and instead of driving the 1.5hr trip each way two days in a row, I decided to just get a hotel room in Providence. The first day of negotiations went so well that the 2nd day was to be more or less just signing the contract. Which meant I could go out and check out a bar or two and celebrate a job well done. I took my time getting ready, had a few pregame drinks that lead me to go out with a goal: get laid.

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