My Anal Boss

A True Story

At that time I was 39 and he was mid-60s. He controlled a small empire that he ran mostly hands-on and I felt fortunate that he took a shine to me and spared me the intimidation and tyranny he dealt to others. I wouldn’t say he was overly nice, but he was fair and pleasant. Business-like. Professional. Aloof. But there was something intangible there. I could feel it.

I was just a consultant. He’d hired me based on a word of mouth recommendation. I’d assumed that was for my professional skills, but perhaps there was more to it than that. I’d seen his eyes straying to check out my bum in my tight jeans, and I recognised the way he positioned me to spend more time with him one-on-one. So after working back one night to finish some important projects with him, I deliberately put myself in harms way and he obliged without hesitation.

We kissed awkwardly, it was just a formality, the way you do with a stranger in a club or a one night stand. He struggled at my jeans belt, first thing to get my pants down then to cup my cheeks and part them to circle his finger at the entrance to my clutchy pussy and roll his finger inside me with a weakening of my knees to accommodate. There wasn’t any real need to discuss it, we both knew where it was going and took it straight there.

It all started to fall into place when I emancipated this glorious 8-ish inch cock from his chinos, my eyes widened as I got my first solid glimpse at the slightly bowed tool and enthusiastically sucked in into my mouth, filling me to gag as he held his crotch against my face. My arse flared in anticipation as I squatted at his feet and inhaled nothing but our thick mature cock down my throat. I sucked his cock as it got harder and thicker in my mouth, thinking what a stroke of good fortune this was becoming with every millimetre that big dick swelled for me.

He wasn't much for foreplay tho. It was all business. He was measured and controlled, where I was nervous and a little frenzied. That first time he fucked me spit-lube raw there in the office and his pleasingly thick cock didn’t even get in my line of sight as I was pivoted and penetrated on the spot and he wrestled his way into my hole, breaking traction long enough to slip and grind away a few minutes slapping his crotch and balls against my round white bum before unloading with a frustrated cry into my depths. I just looked back over my shoulder at him panting and smirked as he gathered himself and I felt his sperm slowly leaking out down the back of my thigh. It was succinct – professional – purposeful, hot and horny.

There was no aftercare. It was maybe a kiss, maybe not, rough oral, bareback anal, an arse stretched and full of cum and then he'd dump me cold like it was time to change the subject completely. He'd discuss business while I was getting dressed! It was a reset then go again the next week.

This scenario, or similar, was how we rolled for the next few meetings. The work would be completed, to a high standard I might add with pride, then it was close the laptops and time for his wonderful cock to find its way inside me at both ends. My time there went fast. It was only a few weeks but he must’ve fucked me half a dozen times and when I I moved on to the next job he left a cock-sized hole in my life.

So fast forward 10 years. Here I am purely by coincidence at an outer suburban shopping centre in Adelaide, somewhere I’ve only come to because I had a meeting in the area, and would never ordinarily be here. And here of all places, out of context, and out of the blue, I recognised him by his sideways smile and the way he raised his eyebrows at me. Here he was “the big boss” still with that air of charisma albeit now rounder, balder and greyer than before. He slightly waddled toward me, and he still fired an instant hormone surge in me and as he approached.

We chatted, he was very complimentary, I felt his eyes burning holes in my clothing thru those expensive sunglasses of his. None of that intensity had been lost, it was like stepping out of one moment in time and back in again at almost the same moment. I felt awkward and boyish. He made me laugh inappropriately loud at the same old jokes and one liners I’d heard all those years ago. He had that afect on me. I was attracted to him. I can't deny that.

He's semi retired now. So he asked me to come back for a quick look at his “weekender” which was apparently nearby. What the hell, I thought! Of course I did. I cancelled my afternoon meetings, flicked my phone to silent and followed him in that big old Mercedes Benz a few minutes down the road and into a semi-secluded block off the main road and parked out the front of the upmarket modern beach-style home. “You look like you need a drink”.

We sat up on the verandah overlooking a small lush yard and drank a couple of cold beers. After the small talk, he told me how he’d often thought about me over the years, and wondered why I hadnt been in touch. I was flattered and felt slightly guilty. He made me feel like I’d been something special when I’d just assumed I was another notch on his office chair. Shielded from neighbours by rows of large trees, courageous with the news that his wife was staying back in town, I took off my pants and straddled his lap on the verandah in his big cane chair and slapped my lips on his. He cupped my bum that same way he had and I rolled forward onto him so he had a good full grope of my bottom. We needed to go inside!

With the luxury of time not afforded us previously, I was able to give the boss the attention he wanted and, frankly he deserved. We both stripped naked and I gave him a proper blowjob, sucking his delectable cock hard and lavishly licking and mouthing his balls and treating him to an entusuastic rimming, which had his penis at 90degrees upright attention! His cock was a work of art, I hadn't romanced it in my mind in fact i'd undersold it. He smelled good his balls were perfect and full. His cock was so clean and perfect and that bow made it distinct and incredibly rideable.

My tongue probed his tangy arsehole and he positioned me to reciprocate, and the moment his mouth sucked on my pussy I almost collapsed on top of him. He licked, fingered and probed at my hot cunt, tugged at my now hardening dick and verballed me like I was his whore. Just naturally without the need to tell me, I mounted him gently and sunk his rigid cock bareback into my pussy and began to ride him with our tongues kissing and naked bodies pressed together.

His cock inside me was like a therapy. I think he felt the same about my hole. We both oohed and aahed and winced to avoid cumming too soon. It was like a lost piece of the puzzle, that fitted together perfectly. My arse swallowed him up. It felt like he grew another inch inside my depths and I threw my head back t wriggle onto him fully. I wanted all of him as deep inmate as I could take, Nothing left behind. His cock slipped freeley into me and my hard dick slapped at his belly as I rode. I arched my back and sat right up on his dick, allowing him to hold my ribs and work eevery last millimetre of his mature tool in my box. I couldn’t help but laugh, even if it somewhat detracted from the moment, out of pleasure and a staisfaction of this return to our relationship. Power imbalance? Well at least for a moment there I was in control!

He told me he was going to destroy my arsehole. It made my balls draw up with excitement. He positioned himself behind me on all fours, taking a moment to spread my bum cheeks and admire my pink gapey hole, commenting on the size of my pussy and how he’d always known I was a “well fucked cunt”. I mean, he touched a nerve there because I’ve always tried to be selective on who fucks me, but the numbers add up over time and lets be honest, I let this guy fuck me for three and half weeks then he disappeared from his life, so how could he have any other opinion of me than “slut”.

And that’s exactly what he thought. He commented on how much of a slut I was to let him fuck me in his office back when. How could I let a man his age bareback fuck me and cum in my arsehole, then let him go home to his wife and family. How did I just pull up my pants with his cum oozing out my pussy and act like nothing happened after he’d fucked me and how did I keep a straight face working with other staff in that environment. Legitimate questions really! I'd never really looked at it from his perspective. Maybe I was the perpetrator? Seemed legitimate as he thrust his cock into me from behind and i pushed back against him, being him to fuck me harder and loving his glorious mature dick inside me.

He fucked away at me doggy style and I felt his sweat dripping onto me. His cock was twitching and I thought he must be close, so I rolled around and lifted my knees so I could see his face as he finished off. Sure enough moments after he leaned back and grunted as his cum flooded my pussy in spluttering spurts that felt like a hose had come untangled in my arsehole. I tried to kiss him and he pushed me away. He let me suck his cock clean and I fingered his cum into my arse hoping to lure him into a second round, or at least to give me some more attention. But he was done. "Thats still a hot cunt you have" he muttered as we gathered ourselves "my wife might come soon so you better go". And with that he left me the room and me to get dressed.

Back to business.

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