Masturbating With My Boss

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My boss and I masturbated each other twice a week...

 

I got a part time job making deliveries for a print shop that catered to businesses downtown. By the time I returned from my deliveries, the printers had left, and only the boss was still there, in an office overlooking the shop.



Most days I ended my shift by jacking off in the toilet, something the boss seemed to condone by stocking the bathroom with Playboys and Hustlers. My sessions did not escape the bosses notice, and one day he called me up to his office, and after a few words asked if I enjoyed the magazines in the bathroom. When I told him I did, I'm sure I must have blushed! He was a very suave gentleman, though, and was totally unflustered. In fact, he asked if I wanted to see some more pictures, special ones, and he pulled from a cabinet a stack of photos.



In those days, 'hard porn' was difficult to come by, but here was a stack of amazing pictures of pussies, blow-jobs, fucking and cocks that completely stunned me. We started flipping through them, and I was more and more excited and speechless. I felt like the first time my little friend and I stole a magazine and looked at it together, our penises tingling as we breathlessly uttered 'wow'. My friend and I lost little time in dropping our pants together and masturbating, a ritual we repeated many times over the next years.



And so when my boss unzipped his trousers and pulled out his cock, I followed him and soon had a raging, dripping erection. My eyes were glued on the pictures on his desk; his were on me, and he was clearly more and more turned on by watching me, and I felt embarrassment at his lust, and excitement such as I'd never felt before.



When I finally dared look at his cock, it was hugely proud of his trousers, long, thick and dark, with a wad of black curly hair hiding his ball sack. I'd never seen a grown man's erection before, and I couldn't look away. The boss flipped through a few more pictures, and then stopped. His hand, which had idly held his erection, grabbed his cock and displayed it for me.



He reached over and took my hand from around my cock, and put it on his own, and then began stroking me. His hands were soft and manicured, with a large gold wedding band, and they took hold of my cock firmly, possessing it. I can only describe the feeling of his hand as one of lust, pure lust pouring into my over-excited cock so strongly that, in a matter of seconds it seemed, my thighs were quivering and I was shooting gobs of cum onto the sleeves of his suit!



I'd let go of his cock, and after I calmed a little, he took my hand and curled my fingers around his shaft. 'Does my cock feel good?' he asked? He unbuckled his pants and let them fall, exposing his enormous balls, which he fondled as I awkwardly stroked him, and he urged me on. Gradually, I relaxed, and began long, regular strokes, which he followed with his hips, moaning-softly at first, and then uncontrollably, and obscenely telling me to fuck his cock and make him cum.



And boy, did he ever cum! His legs buckled and he shot huge wads of cum that covered my jeans and dripped to the floor. I looked down and felt ashamed and embarrassed, and quickly ran down through the shop to the toilet, where I tried to wipe the cum off my clothes before going outside. I wanted to race outside, but he was standing at the toilet door when I opened it.



He smiled. 'Come upstairs, and I'll dry your jeans.' I followed him and sat in his chair while he disappeared into his private bath and returned with a hair dryer, and told me to take off my pants. I was excited and scared and, trembling again, pulled off my pants and watched him drying my jeans. Once they were fairly dry, he playfully pointed the hot air at my cock, and took my balls in his hand and held them up to 'dry'. I was quickly erect again, and this time, flushed with the hot air, he gently stroked me over and over until my cock with dripping with precum as he squeezed the tip between his fingers. I never wanted him to stop stroking me-it was the most awesome feeling! Then, out of control, I began fucking his hand, faster and harder, his smooth, smooth fingers squeezing me hard, and the most amazing, long, strong orgasm overcame my whole body!



Well, what can I say? For the next year I pretended to my classmates that I had a job, two afternoons a week, in the City. In fact, I did get a regular paycheck-and an awesome payoff for cock play with my boss. Sometimes I felt guilt and shame, but more often, just lust, pure lust.

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