Caught my boss sucking cock and joined them to wank off to the show

Submitted by David in London

I think I should begin this by making clear that I’m really not proud of myself for how my first wank buddy experience happened. I don’t think it puts me in a good light, but you have to understand that this was a long time ago and I was a desperate young man just trying to get my foot on the ladder.

I was 26 and it was my first real job, the first time I’d gone for something I really wanted. Before that it was all warehouse work, construction gigs and occasional small office jobs that never worked out. I applied to be a client manager for a fast growing marketing company in central London, I definitely wasn’t qualified and the boss was right not to offer me the job, but he was apparently impressed with me enough to offer an assistant position. It was half the money, but it got me in the door and there were real opportunities to work my way up.

Everything was going pretty well.

About six months into the job I started noticing something weird. Occasionally I would work late and be the last one in the office, apart from the boss, and I would see a guy coming in while I was leaving.

I don’t know how long the climax lasted but at one moment all three of us were cumming, it was all pretty quick and well timed. My boss’ cock was pumping a thick white load all over the guy’s bearded face, his cock was splashing watery semen up his abs and chest, and I was erupting a pretty big mess over his torso too.

Most people wouldn’t think anything of it but he looked out of place. He looked like he’d just come from the gym, vest top and shorts with a bag on his shoulder. I knew he wasn’t one of the cleaners because they didn’t turn up until the middle of the night.

I know you’re probably thinking I should have worked all this out faster, but I was clearly a bit of a moron when it came to this shit. My boss was a 35-year-old married man and the thought of him cheating on his (drop dead gorgeous) wife never even crossed my mind. Ironically, I only found out a year later that my girlfriend thought I was cheating on her during this time. I was giving her excuses about why I was late home so often and she was convinced that I was sleeping around when what I was really doing was trying to get dirt on my boss to give me an advantage.

So, I hatched my shameful plan. Again, I’m not proud of this, but I was a young man who apparently thought he was involved in the cliche world of New York business from the 80’s where everyone stabs everyone else in the back whenever they get the chance.

It was probably week of waiting and “staking out” the office before I saw the guy walking in again. I followed, paced around in the toilets for a few minutes panicking about the whole situation, then I went toward his office where I milled about in the corridor.

I peered through the little glass window beside his office door and caught them in the act. The gym-going guy was now sitting in one of the bucket chairs in front of my boss’ desk, naked, with his pretty big cock being gobbled by my boss, who was kneeling on the floor between his thighs wanking himself off while he sucked it.

My plan to walk in and catch them fell apart quickly. If I’m honest about it I probably didn’t have it in me to blackmail anyone and I don’t really know if I would have been able to go through with something like that. Instead of getting dirt on him and using it, I found myself spying on them like a pervert.

Remember, this was my first experience of anything like this. Apart from watching a few 90’s TV shows of the time this kind of thing wasn’t on my radar. Obviously I knew guys did stuff, but it was pretty cut and dry in my mind; you’re either gay or straight, and if you’re gay you like anal with guys and hook up with men in toilets, life is tragic and you die young. Straight married men don’t do these kinds of things and if they do then they’re in the closet.

That’s just how things were seen back then, at least that was my experience of it.

I was pretty certain of who I was then. Nevertheless here I was watching my boss sucking a guy’s cock in his office and I was getting hard.

I got my dick out of my trousers and started wanking. I think I was on a kind of autopilot by this point. I watched my boss stand up move forward and start rubbing his cock against the other guy’s dick, wanking them both at the same time. The gym guy (you’ve probably guessed I never found out his name) was just sitting there letting him play with it to start with, then my boss moved further up and the guy moved forward to start sucking him too.

That’s when my boss saw me and I ducked out of the way, too late of course. I peered back through the glass and my boss was smiling and motioning for me to come in.

The whole plan about catching him and using the information had been forgotten. I walked into the office and approached slowly with my dick in my hand while my boss humped his cock in and out of the guy’s bearded face. The other guy noticed me but he didn’t seem bothered by my being there.

That was it for the next fifteen minutes or so. I kept my distance and just watched. I didn’t think about it much I was just enjoying the show while these two men sucked, licked and wanked each other. I knew I liked the look of their cocks, but who doesn’t like looking at a good dick? My boss had about 6 inches with a good pair of nuts on him and the other guy had a very thick and long shaft with a slightly pointed tip and he leaked a lot of precum.

For the more curious guys who want to know about me I was a fit guy then (not too bad for my age now either, actually), I’ve got just over 7 inches with low hangers and a little extra foreskin that guys like playing with.

So back to the office… Apart from a lot of looking and admiring while I stroked myself they were apparently happy for me to just be there watching. I think the other guy motioned for me to come closer and get sucked at one point but I didn’t move.

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I watched them playing with their cocks and wondered if they might start fucking but they didn’t, it was all about the dick. I’m glad they didn’t fuck, and I don’t think they ever did. I guess they were not too different from how I am now when it comes to masturbation and (occasionally) oral. This concept was totally alien to me at the time but I get it all now, of course.

When things were getting closer to a finish I was probably about five feet away from them just stroking my cock and watching. My boss was feeding the guy his dick and the gym dude was wanking himself off and I watched my boss pull his dick out of the guy’s mouth and start cumming in his mouth and over his face. The gym guy immediately started cumming too. My cock had been ready to unload for a few minutes and I instinctively stepped forward on the other side of the guy and started cumming. I think I might have only done that because I didn’t know what else to do with my load and they were both making a mess all over him so it automatically seemed like the thing to do.

I don’t know how long the climax lasted but at one moment all three of us were cumming, it was all pretty quick and well timed. My boss’ cock was pumping a thick white load all over the guy’s bearded face, his cock was splashing watery semen up his abs and chest, and I was splashing a pretty big mess over his torso too.

By that point it was the most erotically charged experience of my life. I didn’t understand a bit of it and it freaked me the fuck out. I shoved my cock back into my trousers and almost ran out of there. I was so freaked out by it that I hit the button for the lift and then decided it was taking too long so I went down the stairs, almost falling because my legs were shaking so much, just to get out of sight as quickly as I could.

I must have scared the security guard I almost ran past on my way out.

So that was my first experience of wanking with other guys. It’s not much like the experiences I’ve read here so I thought I should share it and maybe it will give a few readers a good stiffy to play with.

A lot has happened since then. I had a few more wanks watching them after that and it became a thing. I started wanking with my boss during the day and wanked him off for the first time. I got a promotion but I was assured these things were entirely unrelated. I got married, started a family, got divorced. I still meet up with my old boss about once every few months and we have a good wank. I started meeting other guys for wanks around London when the internet became a proper thing and I got into the “scene” so to speak.

I hope readers enjoyed my experience. If I get the time I’ll write about the first mutual masturbation experience I had with my boss too and maybe some of the other highlights of my wanking career!

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