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Hooking Up With the Big Boss

In my late 20s, I spent a year or so working for a consumer electronics retailer in the IT department. The company was a complete mess and my boss was almost never around. There was very little work to do at any given time. Shockingly, the company owners' seemed to be OK with all of this. I had expected the job to come to an end sooner or later with no real pay off when I had an encounter with one of the owners.

At this time I'm 28 going on 29 and he is 53. I'd never really talked to him much and knew very little about him, other than rumors he went bi after his divorce, which only went around the office because of a friend of his ex-wife working in our warehouse. One day, I'm in the break room grabbing an afternoon cup of coffee, bored out of my mind as usual, when he walks in and says hi to me. I was a bit surprised as it was maybe the second time he's spoken to me in the year I'd been there, but I say hi back. He's all smiles and we start up some small talk. I end up telling him I'm a bit bored at work and hardly see my manager, so he askes if I'd like to help him with a project. It starts out innocent enough - he puts me in an office adjacent to his and has me manually backing up several old PCs for him - so far its better than my usual job. A couple of days after receiving this new task, he asks if I can stay later than usual one night to help finish a server migration project. I agree and end up staying several hours past my usual time off at which point he asks if he can buy me a drink to say thanks for staying late.

We end up driving together in his very nice Audi and go to a bar at this Marie Calendar's restaurant of all places where a basketball game is playing on the TV and he orders us drinks, assuming I like scotch. We start drinking and the small talk starts, he asks if I'm liking things better now, and I say yes. Finally, he asks if I have a wife - I say no. He asks 'girlfriend'? I say no. Then he says - 'good looking guy like you, I'm really surprised'. I decide to trust him and replied, "well, I'm actually gay." It was like that was all it took to set off a spark. The way he looked at me after I said that made me feel like he wanted me then and there and I looked him up and down feeling lust overcome me.

Not five minutes later we were back in his Audi headed to his place as I'm leaned over the center console with my hands and head in his lap frantically trying to get his penis out as if it's gonna save my life. As I free it from his jeans I see its not only sexy, its big too, and I start kissing the head real wet and deep, sucking it into my mouth as it begins to pulse into a hard-on. Something about this guy is just driving me wild now - aside from the nice big cock of course. Its his smell, his hot older body, his smooth sweet voice. I really give it to him, unleashing my entire knowledge and experience in cock sucking as he moans and grunts, still driving us up the freeway towards his place. We don't even make it to his exit before he starts to cum hard in my mouth. I keep sucking on him as heavy generous cum spurts coat my tongue and throat, swallowing deep as his orgasm finishes. I suck and lick the tip clean and put his cock away in his jeans before sitting back up.

He glances at me speechless with a look as if to say, "where the fuck did you just come from". I laugh. We get to his place. He has another drink and we make out in his bedroom before he goes down on me, sucks the cum right out of my cock, eats my ass, and fucks me so deep and hard I cum a second time all over my stomach while I take his second load deep in my ass. We fall asleep together and he takes me back to my place early the next morning, and then to work.

Back at work the next day, he was super professional, treating me like a subordinate and like nothing at all had happened. Then over a period of several days he disappeared into meetings and I rarely saw him, resorting back to my job of boredom. Then out of the blue almost a week later he appeared at my desk one evening as I was about to leave. "Drinks and my place again?" he simply asked.

Unfortunately for him, the company went out of business months later and I moved on from him and the failed job, but not before having several more hot sessions with him over all most three months. More to come on those ;)


I liked all that, down to him not pestering you, giving you special treatment etc and then getting down and dirty for sex. My only experience with a boss ended after he fucked me a few times. I was pretty young and green and went along with the line of "I'll get you a better job", in reality he was only using my body as a cum dump. Not that I minded, I did learn a few new positions and at that stage it was really all about sex!

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