[MF] On a rooftop in Manhattan

*Quick intro note: I’m a handsome, vaguely articulate, well-educated, married and generally successful 39 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.*
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Caroline and I met, very briefly, smoking a cigarette outside of a bar on Bleecker Street. She was on her way out, I was on my way in, and she asked for a cigarette. She was tall, blonde, and beautiful in a way that was immediately intimidating. I’d imagine that she could count on a single hand the number of times she hadn’t been the prettiest person in any given room. You might expect a person like that to be entitled, bitchy, and cold. And you’d be right.

[M]y perfect little sub’s [F]irst time with another woman

*Quick intro note: I’m a handsome, vaguely articulate, well-educated, married and generally successful 39 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.*

Annika and I met on a dating app and quickly realized we were neighbors. In New York, you’re neighbors with a lot of people, but Annika and I weren’t neighbors in the sense that we both lived in the East Village with 700,000 others. We lived about 30 yards apart. From my rooftop, I could see into her living room window. 

It’s easy to date in New York, and with dating apps, you could have drinks or dinner with a new person nightly if you had the desire. And while I wasn’t quite doing that, I also wasn’t far from it. So the reality is that I don’t remember much about our first date, except that we were lazy and went to the only restaurant between our apartments, and that she wore a very low cut shirt. Lower cut that you’re thinking right now. In retrospect, it’s obvious she was trying to signal something, but I missed it at the time. 

[MF] On display on a Manhattan rooftop

Quick intro note: I’m a handsome, vaguely articulate, well-educated, married and generally successful 39 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.

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Caroline and I met, very briefly, smoking a cigarette outside of a bar on Bleecker Street. She was on her way out, I was on my way in, and she asked for a cigarette. She was tall, blonde, and truly beautiful, in a way that was immediately intimidating. I’d imagine that she could count on a single hand the number of times she hadn’t been the prettiest person in any given room. You might expect a person like that to be entitled, bitchy, and cold. And in this case, you’d be right.

[MFF] The time I fucked my ex in front of my lesbian friend.

*Quick intro note: I’m a handsome, vaguely articulate, well-educated and generally successful 38 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.*

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I’ve fucked a lot of women in my life. Almost certainly more than is healthy. If I could only fuck one more it would be Sarah. 

It was immediately tangible the moment we met. Whatever it is that causes sexual attraction — the hundreds of thousands of psychological, genetic, and cultural inputs, pheromones, fate, whatever — aligned, and kicked off an intense six month love affair. I didn’t get fired from my job during that period, so I must have gone to work. But if pressed, I don’t think I could describe a single thing from that stretch of time that doesn’t involve fucking Sarah. 

There are a dozen stories I could tell about Sarah. But my favorite was fucking her in front of my friend Melissa. 

[MF] What happened when I followed Julia off of the train.

*Quick disclaimer: this story involves two consenting adults, but does involve some consensual non-consent play. Don’t read on if that’s not a good thing for you to read.*

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*Also, quick intro note: I’m a handsome, vaguely articulate, well-educated and generally successful 38 year-old, pervert. I have a long history of dirtiness, and there’s something about the year and a half of basic confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.*

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This is another story about [Julia](https://www.reddit.com/r/gonewildstories/comments/lohn7k/mf_perfect_strangers_in_a_movie_theater/).

We fucked off and on for a decade or so. Not regularly, but we’d find our way to each other at least a few times a year. It always started with an email from Julia that would simply say “hi”.

[MMF] — Bi-Cuckold play with a couple

For people that have never lived here, it’s hard to fully grasp, but there are pockets of New York City that feel like small towns. Despite hundreds of thousands of people passing through those pockets regularly, you end up finding your regular spots — and the regulars at those spots become people you know pretty quickly. There was a bar like that for me, years ago, in Williamsburg. It wasn’t a particularly popular one, but had friendly bartenders who poured generously, kept packs of communal cigarettes behind the bar, and did a very good job of convincing the assholes who had just begun to infiltrate Williamsburg that they weren’t particularly welcome there. 

During the years I lived in Williamsburg, if I had nothing better to do on a given night, I was usually at the bar there, reading, or watching Jeopardy and bullshitting with other regulars. Maria was one of those regulars. 

[MF] Perfect strangers in a movie theater.

There was a moment in time when Craigslist was a perfectly valid way to meet otherwise normal, but kinky people. This was before dozens of online dating sites popped up, and back when the big ones still carried a bit of stigma. It’s probably hard for people who have always had Tinder around to imagine, but back then, a whole lot of people were embarrassed by the idea of online dating. So to have dirty, casual sex, people used more anonymous means like Craigslist.

In her post, Julia described the fantasy she wanted to live out. She’d be going to a matinee showing of a movie that had been in theaters for months, and thus was likely to be sparsely attended. She’d arrive first, pick a secluded seat, and then send a text message to a pre-selected stranger describing where she was sitting. He’d come into the theater 20 minutes into the movie, lights low, and sit down next to her. From there, nothing was off limits.

[MM] In which a 22 year old me is surprised to find just how curious he is.

*Quick intro note: I’m a handsome, vaguely articulate, well-educated and generally successful 38 year-old, pervert. I have a long history of dirtiness, and there’s something about the last 11(!) months of confinement that has had me reminiscing about my past and some of my hottest experiences. I’ve decided I’m going to start chronicling them here, to keep them from disappearing altogether. Let me know if they’re enjoyable and feel free to say hello. I like penpals.*

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I don’t, honestly, remember the first time I found myself curious about another man. I was always open sexually and have always enjoyed mining the dirtier corners of my mind and seeing what I found. But by and large, I’m straight and always have been. And that’s what made what happened with James such a surprise.

This was back in college, sometime during the summer that I turned 22. I spent that summer house-sitting for a professor of mine. He spent his summers up in Vermont, and would always have a few grad students crash at his place while he was away. I was the only undergrad.