Rag Time Businessman

First, let me introduce myself. My name is Jack Anderson, I'm bi, single, 52, and work for a major corporate outfit in lower Manhattan. I've been just about where I started on the job for the past 30 years, but, hell, with perks like mine, I ain't complaining! I work under two superiors, one male, and one female.

My boss is Mr. Craig Whitehead, a tall, broad-shouldered, divorced bi daddy in his mid-60s. Shit, does this silver-haired fucker look hot in a suit! My supervisor is Ms. Carla Randall. She's hot bitch looks like a fuckin' Penthouse centerfold, dolled up in conservative office clothes. I've been under these two hot-to-fuckin'-trot superiors for years now......I HAVE to obey them.....NO EXCEPTIONS...THEY are the BOSS...and I have no fuckin' problem with that! The other day was a typical hot office romp for us. It was well after hours, and, I knew throughout the day that Mr. Whitehead and Ms. Randall had BIG plans for me after work.

It was obvious that Ms. Randall was pretty bitchy that day, so, I knew right off the bat it was "ragtime" again! and, every time I saw Mr. Whitehead, he give my round corporate butt a discreet swat and whisper: "Your ass is MINE, later, Anderson!" and, of course, I was FORBIDDEN to go to the men's room for a quick wank, so, as you might expect, my hairy balls were churning like mad by the time 5PM rolled around.

So, here we were again, all three of us, in Mr. Whitehead's big, luxurious office, with its dark wood paneling and hounds-and-foxes paintings on the walls. "CLEANUP TIME, ANDERSON!" Ms. Randall barked, and, without saying a word, I got her skirt and panties down to her spike heels. Sure enough, there was some smears of blood surrounding her hairy pussy, and, I saw the string of a tampon dangling so fucking invitingly from between those succulent cunt lips.


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Still on one knee, I eagerly pulled the blood-soaked tampon out of Ms. Randall's steaming twat. Shit, did it look good!!

Then, Mr. Whitehead's big, hairy hands grabbed a handful of my thinning hair, and pulled my head back, my eager mouth opened wide in anticipation. "Here, cocksucker", Whitehead growled, "pretend it's my fat dick all covered in that hot red stuff!" Now, if your a straight or bi guy into tampon/menstrual sex, shit, you'd PAY to be in my place. I started off by sucking Ms. Randall's well-soaked tampon, really getting off on that fucking raunchy taste that made my huge cock throb even more in my pinstriped suit pants. All this while, Mr. Whitehead squeezed and kneaded the huge bulge behind the fly of his expensive suit trousers, really enjoying the depraved corporate action before his bifocaled eyes. Then, without saying anything to me, Mr. Whitehead unzipped his fly, and reaching into to his custom-tailored suit trousers, pulled out his huge, throbbing ten-incher. All he had to do is fist it several times and he growled deep in his bull-like throat as he blasted a huge,creamy load all over Ms. Randall's bloody, gaping, hairy pussy.

Then, Mr. Whitehead's broad paws forced my head down between my sexy supervisor's nylon stockinged thighs, and I just started lapping up that hot, steamy, raunchy mixture of hot corporate jizz with fresh menstrual juices. It wasn't long before my lean face and bifocals were smeared in blood and cum, which dripped down onto my shirtfront and tie. My tongue eagerly went to down, diving ever deeper into this sexy corporate bitch's hot, bloody snatch. Then, I felt Mr. Whitehead's big hands pull my head away, all red-smeared and sticky, while Ms. Randall got up on the desk, her sexy legs spread, her red-dripping twat leaking all over the accounting forms on Mr. Whitehead's desk. "EAT THAT FUCKIN' BLOODY CUNT, COCKSUCKER!" Mr. Whitehead snarled, but, before I could comply, he ordered me to drop my suit pants and shorts. as soon as I slid the suspenders from my narrow shoulders, and shoved my pinstriped trousers and striped boxers down to my gartered argyle socks and wingtips, I saw that Mr. Whitehead had reached into his desk drawer and pulled out his big, thick wooden paddle, the one drilled with beveled holes.

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Then, without being told, I went back to work eating out Ms. Randall's hairy, bloody cunt while Mr. Whitehead, after having rolled back his sleeves, proceeded to assault my meaty, sexy little businessman's butt like a raving madman.

SMACK! SMACK! SMACK! SMACK! SMACK! Judging by the all-out assault my poor white-collar rump was getting, it was obvious that my hunky suited daddy of a boss had a LOT of pent-up stream to let off!!! SMACK! SMACK! SMACK! SMACK! Again and again, Mr. Whitehead brought that big bruiser of a paddle down across my flaming, quivering ass, but my moans and yelps were stifled, as I had my face still buried down between Ms. Randall's silky legs, tongue-cleaning her hot, rag-time pussy. "NOW, SHITHEAD," my hot, suited, 60-something boss barked, "LET'S SEE YOU ACT LIKE THE FUCKIN' MAN YOU'RE SUPPOSED TO BE AND FUCK THAT BLOODY PUSSY RAW!" Again, before I could reply, he chuckled: "...yeah, really love fucking a nice, red piece of white-collar man-ass!! NUTHIN' like it, my little cock-suckin' friend!"

Now, as my hairy nuts churned and my thick nine-incher drooled lube even more, I just took hold of that massive fuckrod and jammed into right into Ms. Randall's steaming, bloody pussy. Shit! what a fuckin' feeling! Her awesome cunt muscles worked over the massive length of my pounding businessman's cock, and, it wasn't too long before her cunt was really ooozing again, her blood and pussy juices mingling, coating my raving cock and my hairy, cum-boiling nuts.

Then, I felt Mr. Whitehead pry my red, welted buns apart, and my cock throbbed as his big, thick tongue started really drilling my hairy asshole, really getting it primed. As I continued to fuck the bloody hell (literally!) out of Ms. Randall's straming, red-oozing pussy, I gritted my teeth and gasped as I felt Mr. Whitehead's thick shaft splay my tight chute, and I groaned deep in my throat as this brawny horny executive fucker just brutally slammed his huge Wall St. wang into my hot, tight, sweaty butt, his big hairy hands grabbing onto my shoulders, giving the royal executive-level fucking that I NEEDED and CRAVED!

His big, hairy balls slapped against my blistered buns, and the teeth of his open zipper nipped my tender ass globes, driving me nuts! Too soon, all too soon, my balls tightened and I knew there was know holding back.

Roughly squeezing Ms. Randall's big boobs through her silk blouse, I let loose with a loud, animal-like growl that, I'm sure, could have been heard up in Times Square! My huge cock blasted jet after jet of thick, hot, Wall Street spunk deep inside Ms. Randall's bloody cunt, as Mr. Whitehead continued raping my impaled ass with his big white collar hammer. As I shot my hot, pent-up load, my ass muscles flexed like mad, really doing an A-1 job on my boss's pounding, divorced daddy dick.

"FUUCCKKKKKKKK", Mr. Whitehead snarled, roughly spanking my sore, flaming ass with one of those big paws, "YEAHHH, FUCKIN' RAPIN' YOUR HOT WHITE COLLAR ASS, BOY!" I felt that huge executive dick explode up my ass, hot gobs of thick executive spooge deep between my well-toasted buns.

When finally, we started to come down off her highs, I pulled my blood-soaked dick out of Ms. Randall's well-fucked hole, and then, as she started fingering herself, Mr. Whitehead got down on his knees and started sucking like a maniac on my blood and cream-covered dick. Shit, this broad-shouldered daddy REALLY had a knack for sucking a cock, let me tell you! As my bloody dick started to harden again, Ms. Randall bent me over just enough, so that she could start humping my red, raw ass. She reached around and pinched my stiff nipples through my sweaty shirt, as she angrily ground her blood and sperm-dripping pussy against my round, meaty ass. When she orgasmed, I could actually feel the intensity, and then her hot pussy juice and a fresh flow of blood splattered all over my aching ass, the hot mess running down my legs, dripping down into my gartered socks.

By this time, I was rock-hard again, and I grabbed Mr. Whitehead's big, handsome, square-jawed head tightly, as my big nuts exploded a second time, and my bloody dick flooded his cock-hungry mouth with scalding blasts of my white-collar jizz.

So much jizz flooded his mouth, it dribbled out of his mouth, dribbling down his chin, staining his expensive shirt front and silk power tie. I looked at the clock, and then remember something. It was a FRIDAY evening.......and our hot corporate weekend had just begun.

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written by spankthose
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