Cheating with the boss’ secretary [mf]

*Disclaimer: If you want to judge me in this story for cheating or anything else, please send me a detailed direct message explaining your issues. (That way you can waste your time and I can laugh while I ignore it.) In all seriousness, I was in a weird place at this time in my life, had a drinking problem, and as a result did a lot of bad, destructive, unkind and risky things. I’ve since cleaned up my life (for the most part) and have tried my best to be a better person and make amends. And as you’ll see in this story, I experienced at least a little bit of karma as a result of this incident anyway. Anyway, here goes.*

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This is a story about loneliness, desperation, bad decisions, and karma. But it’s a story of, objectively, one of the more erotic experiences of my life. So I thought I’d share it here.

At the time this story happened, I was in my mid-20’s and working at a small startup company in New York City. My job was in marketing and general operations, but it was small enough that everybody knew each other, even across departments. And, as happens often in startups, we developed a nice camaraderie with each other over time.

Answered a craigslist ad from a guy willing to suck off straight guys, got more than I bargained for [MM]

*NOTE: I posted this story once before years ago on a different account. But I deleted that account and have since made a new one. I want to tell this and a few other stories and figure I should do it all from one account.*

I should preface this story by saying that I am straight, generally, and had never been with a guy before this story. This was a few years ago, when I was 24, living in New York City and dating a girl long-distance.

My girlfriend and I had been together for a few years, since college, but an amazing opportunity took her to another city for two years. I found myself on the Greyhound a lot and, when I wasn’t with her, often sexually frustrated–especially as I saw all my friends living it up as single guys in their twenties in NYC.