Standard disclaimer: this story is a very over the top work of fantasy, and it contains extreme humiliation, blackmail, and unsafe sex practices. Enjoy!
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The first two days after my gym experience had left me limping painfully with each step. I still met Cliff for personal training sessions in just a jockstrap, but luckily I had not been ball-busted again by Hal and his friends. And outside of a couple of teasing text messages, photos of his huge hairy balls or a close-up of his purple cock head, I was left alone by Mel too.
Three days later and I was at work when my boss Steve Kennedy breezed into my office without announcing himself, startling me when he spoke from behind.
"So who's the lucky young lady?"
He sat his big ass on my desk, spreading his suit pants open, his crotch inches from my face. I couldn't help but look at his bulge - I had never noticed the sizable contents of his trousers before.
"Or man?" He suggested, raising his eyebrow quizzically. I sputtered something, completely flustered.
"None of my business. But I can tell that you've been having some fun." He laughed.
"No Sir, it's not like that, I was just sick, and..." As I trailed off he continued.
"Son I can tell when a man's aroused. You've got ants in your pants. You're distracted. And your little pecker's hard in your trousers about 24/7 by the looks of it." Kennedy said laughing, pointing at my crotch. It was clearly tented. Again I sputtered feebly, unable to explain my boner. I lowered my head as he cracked up with laughter - I can't believe I was hard in front of him. Was I hard because of him? He then patted my shoulder reassuringly.
"Like I said, none of my business. But just make sure to separate work and fun, OK son?" He advised me, his heavy hand continuing to massage my shoulder as I looked up at him.
"Yes Sir." I took in Steven Franklin Kennedy, the head partner at my firm and my direct supervisor. He was far more put together than Mel but still, both men were about the same age, somewhere in their 60s, both men had wide hips, big bellies and domineering attitudes. Now that I thought of it, Steven had always been just as touchy-feely as Mel. Shoulder pats, grabbing my hips or waist, encouraging pats on the backside - he had often remarked that he saw himself as a coach and me as one of his players.
He stood from my desk, keeping his left hand on my shoulder. He then leaned down, and put his right hand on my stomach, holding me lightly, and brought his mouth to my ear, whispering.
"And if the little thing won't go down by itself, just go to the men's room and wack it off in the stall. No shame in that either, just don't make a mess." My face bloomed anew at this suggestion. He brought his face close to mine, looking at me intently.
"Yeah?" He asked, demanding an answer.
"Yes Sir." I croaked out nervously. Was I agreeing that I would not let my newly invigorated sex life distract from my responsibilities? Or did he want me to agree to masturbate in the bathroom at work?
"Attaboy." He slapped my shoulder once more and left me sitting there beet red and hard as a rock in my chair.
I had hoped that this would be the last time I ever discussed my masturbatory habits with my boss, but I should have known based on the recent trajectory of my life that I would have no such luck
"Petey, you, uh, taking care of business?" He asked, making a wrist pump gesture, grinning and winking at me lewdly. It was the universal "jerk off" symbol.
"Uh yes Sir." I said.
"Good. Make sure of it. As many times as necessary. I know how you young fellows are." He smiled, slapping my shoulders. He walked way then called back.
"Remember, there's no shame in taking matters in to your own hands!" He said, way too loudly from across the hall, making the jerk-off motion with his hand again.
Later that afternoon he grabbed my hips as I passed him in the hall. I let him detain me as he lightly pushed me against the wall, stepping in close.
"Petey, how's it hanging? It better be hanging, son. If the little soldier's standing straight up, for Christ's sake go take care of it, boy." He ordered, chuckling, gesturing with his pointer finger up and down in my face to mimic my flaccid versus erect penis.
"So what is it boy, hanging or standing up straight?" He raised his eyebrows, waiting for an answer, his left hand still holding on to my hip.
"It's hanging Sir. Just hanging." I whispered, my voice hoarse.
"Good boy." He praised, patting my butt upon releasing me from the inappropriate interrogation.