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My Affair: The Beginning

I’ve known Rachel for quite some time. We met via a group of social media enthusiasts back in 2007 when Tweet-Ups were still a thing. She and my wife hit it off pretty well and soon we were hanging out with Rachel and her husband quite a bit. They’re about our age, a little younger. Rachel is a grad student. Her husband works in IT. She’s very cute, in fact she looks a bit like my ex-girlfriend Laura (see my previous stories for some info on her).

[M]Fucking the girl from high school finally

Read till the end its a long story but its 100% true!!

In high school I was kind of the nerdy type punker skater boy.. Girls didn't pay too much attention to me although I was really funny so I'd get my share of pussy here and there. Anyway there was a girl that all my friends and me wanted to fuck so bad..we will call her.. Kenna. I only knew her through a friend in my class that I pestered to give me her phone number and surprisingly she entertained me even though she would never consider me as I considered her. Nothing ever happened.

I had my best [FMF] today with a frisky chick and a guy who can really fuck.

Let’s just start with the fact that my pussy is really sore right now. I’m just sitting here in my black bra and polka dot panties, on my couch in my living room with my laptop on my lap and my pussy is throbbing. The good kind of sore where you know you got what was coming to you.

Here is how it all started.

Giving in to my [mm]

The following took place a little over ten years ago while still in college.

While I have and currently identify as straight, I had fantisized about submitting to another man for years and finally worked up the courage to post an ad. Of all the replies, this guy felt like the least threatening. He seemed nice, a little chubby, but he wore it well.

We were both a little nervous when he came over, I offered him a beer to help break the tension. We bsed a little bit, mostly about photography, when he suddenly cut in,

[M/f] skipped school today and hooked up with my boss

A little back story: 18/f about to be done with school. I have a fwb and my best friend that her and I occasionally mess around but nothing committed. Her and I work together and have been best friends since 4th grade. We have a notebook that has sex acts we want to do, with a ton of different variations, if its been done yet, and how it was and who it was with. Sex with a man 5-10 years older was on the list.

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