Picky, Picky

by Habu

3 Mar 2008 727 readers Score 7.5 (4 votes) PDF Mobi ePub Txt


The young man's hand was trembling as he handed the creamy vellum envelope embossed with the FGCC crest over to the older man. Edward Winslow held the younger man's finger between his and the underside of the envelope for an extra couple of seconds before taking the envelope and placing it carefully on the top of the cigarette table beside him. He puffed on his cigar and smiled a satisfied smile to himself. He wanted Bill Brewster to tremble at the thought of handing over that envelope. It was final nail in this particular coffin.

Bill Brewster shifted nervously in his crackled-leather Chippendale lounge chair in the dim corner of the First Gentlemen's Covenant Club smoking room and moved his slender, finely manicured hands together in a tented position, his fingertips centering between his patrician-shaped nose and his full, dry lips. He was doing all he could do to control the trembling of his hands, and he didn't want Winslow to see the trepidation his face surely revealed. He wasn't looking directly at his boss at First Families Securities, but Edward Winslow was looking directly at him and was smiling, clearly enjoying not just the young man's resignation but also his discomfort.

A tall, fine-figured Hispanic in a smartly tailored black silk uniform materialized at the side of Winslow's chair and set down a snifter of port. In withdrawing his hand, he barely brushed Winslow's hand with his. The senior partner of First Families Securities, the son of a son of a son going back to the arrival of the Mayflower on America's shores - the very prize that qualified Winslow for membership in the Beacon Hill First Gentlemen's Covenant Club - twitched his hand back, almost as if he'd been shot, and sent the port in his glass into a brief tempest.

'Damn Mexicans,' Winslow muttered, as the servant moved silently behind the two chairs and, appearing at Bill Brewster's elbow, quietly slid the second snifter of port on the cigarette table beside the younger man.

'The old club's going to the damn Mexicans,' Winslow continued to mutter. 'At least the darkies they had in here before knew to wear gloves.'

Bill Brewster picked up the snifter and moved it toward his mouth. But his hand was trembling so hard that he had to take the crystal vessel in his other hand as well to hold it steady. He took a gulp from the glass - quite out of character for a son of a son of a son, who had equal rights to FGCC membership to those Winslow had. But these were circumstances he'd never faced before.

It wasn't until this evening that Winslow had fully believed Brewster would actually go through with it. The room key in that vellum envelope lying beside Winslow's snifter settled that question.

Winslow snapped his fingers and the liveried attendant appeared at his side.

'Casa Blanca Jeroboam. No two. Now.'

The servant vanished in search of the cigar humidor behind the long bar.

Winslow looked back over at Brewster, who was breathing heavily, obviously trying to contain himself. This had been a campaign of his for nearly a year. When Winslow had offered the younger man the broker's position, he had made it clear the extent to which Brewster was to show his gratitude. Brewster was a natural for the firm and looked the part perfectly, but he had majored in partying and tennis at Harvard, where only his name had stood him in good stead, and he normally could not have expected to have been given a position in the firm, despite his lineage.

The attendant reappeared, and Winslow snatched one of the cigars from him and motioned with an irritation usually reserved for the slow of mind for the other one to be placed on top of the vellum envelope. He hissed his disapproval that the Mexican had handled the cigars; they should have been delivered on a white linen napkin.

'No training whatsoever,' Winslow muttered. 'Can't train a Mexican. Heh, William?'

'Ye . . . yes, Edward, that's . . . that's right.' Brewster was obviously uncomfortable, but it wasn't about Winslow's berating of the servant, because he added the unnecessary. 'Training would be a waste. He'll be slipping back across the border as soon as he's made a few bucks.'

'Next time on a napkin, Jose,' Winslow hissed.

'Yes, sir,' the servant said, his eyes downcast, as he backed into the shadows.

'You know his name?' Brewster asked, the tone of his voice revealing how incredulous he thought the idea that Winslow would take that much notice of one of 'them.'

'They're all called Jose, aren't they?' Winslow said. And they both laughed, although Brewster's laugh was edged with a bit of hysteria.

'So, are you sure?' Winslow said, fingering the vellum envelope. 'I've heard that Fenton and Felton are hiring.'

'Yes, I'm sure,' Brewster responded in a small voice. The mention of Fenton and Felton, a decidedly plebian firm, was pregnant with meaning.

'You'll have to ask for it,' Winslow said. 'I'll not force it.'

'Yes, thank you, sir. I understand,' Brewster said. 'But you will . . . we can . . . you know, what we agreed on.'

'Yes,' Winslow whispered sotto voce, his voice laced with exasperation. 'If you have a blindfold, you can use it. And I have restraints. If it's easier for you, we can do that if it makes you feel less guilty.'

'Light,' Winslow said in a louder voice like the flick of a whip. He snapped his fingers as he said it, and the Hispanic attendant materialized from the shadows and lit Winslow's cigar for him. And then he faded away as quietly as he had appeared.

'Well, you'd best be going up,' Winslow turned to Brewster and said. 'I'll be up shortly. I don't care if the lights are off and you are blindfolded. You are going to enjoy it, so don't look so glum.'

'Yes, sir,' Brewster muttered in misery. He gulped down his port and moved unsteadily toward the door and to the elevator.

Nice ass, Winslow thought, as he watched the young man move away. Good looker, nicely muscled and trim. Just the way I like 'em. And young men of his pedigree are hard to come by. As only America can produce through generations of residence.

Winslow closed his eyes and let his head loll back into the enfolding leather of the Chippendale chair and dreamed of fucking the very presentable and finely familied William Brewster. A year's campaign but all worth it. After a brief reverie of taking the young man from several positions, Winslow realized his cigar had gone out. He snapped his fingers.

'Light.'

Nothing happened. Winslow's eyes shot open and he looked to his left, where the Hispanic attendant should be standing. No one was there, but Winslow's empty snifter had been cleared away. No servant, though, and Winslow's cigar had gone out.

'Damn wetback,' Winslow muttered. 'Probably already half way back across the border. Probably an illegal too. The club standards have gone to shit.'

He leaned over and smashed the ash end of the cigar in a crystal ashtray, and, while struggling up out of the mothering clutches of the deep armchair, took up the second cigar, put it in his shirt pocket, and took up the precious vellum envelope.

While waiting for the ancient elevator to clank its way back to the public room floor, he opened the envelope and took the key out.

612, he thought. I didn't know the club even had six floors. Must be in the attic. I wonder who Brewster ticked off at reception when he checked in.

* * *

Bill Brewster was naked and lying on his belly on the silk sheet covering the double bed in the middle of the club guest bedroom. He lay in the dark, his eyes covered with a blindfold, his eyelids held tightly shut, and his breathing ragged and his body twitching at what was about to happen.

He heard the key in the lock, and he almost whimpered in uncertainty and fear as he sensed more than saw the brief invasion of light from the hallway before the door was clicked shut and subtle sound of the rustling of shed clothing reached his alert hearing.

This was his future. He'd made a deal with the devil. He'd been told that Winslow was cruel but that he didn't sustain interest. A couple of months, not more, and he'd move on to other quarry. And then Brewster's future would be made. He'd just have to steel himself. His ancestors had taken the risk and grabbed for the gold ring when they'd sailed for the New World on the Mayflower. At least Winslow had the right pedigree. Brewster could still hold his head up after this. Just some pain and private humiliation and then his future would be made.

Brewster lurched and made a little yipping sound as he felt strong callused hands taking his wrists and tying them together and then forcing them over his head and tying them off at the headboard.

Such strong hands. A little surprising, the strength, but Winslow bragged incessantly about his garden and how he worked it himself. Brewster shivered a bit. Strong hands. Would that mean other strengths as well?

Those callused hands were running all over his body as he lay stretched out on his belly. He was trembling and trying to think of anything else but what was happening - what was happening at last after nearly a year of putting it off. If he'd let Winslow bed him as soon as the employment deal was set, it would be all over now. It would be done and Winslow would probably already have moved on to fresh tail. No use crying over that now. Just bear it. Pretend to be somewhere else altogether.

But pretending to be elsewhere was becoming increasingly difficult. Those hands were tantalizing. No woman had done this to him, had taken the time to put him into a mood. Pleasurable. He had to admit that it was pleasurable. He was beginning to calm down, and he caught himself sighing.

Hands were on his hips, lifting them, signaling that he was to go up on his knees. He started to rise, and a large hand palmed him between the shoulder blades and showed that only his hips were to go up, that his chest and cheek were to stay flat on the sheet. His arms, trapped above his head were beginning to go numb and to tingle. But the skin of the small of his back and his butt cheeks was tingling too. This was a different tingle, though, brought about by the movement of lips and tongue on his body.

Brewster moaned as a hand came between his spread thighs and took possession of his dick. He hadn't realized it, but he was hard. A flash of embarrassment shot through him. Winslow's attentions had made him go hard. Letting yourself be fucked by a man was one thing, but your body showing that it was enjoying the attention was quite another. He gulped and whimpered as the stroking began. Then he didn't quite manage to swallow a yelp when the bulb of his dick felt the lips open over it. A tongue was flicking his piss slit as the lips slid farther over his throbbing dick. Fingers were probing his balls and pulling on his sacks. Brewster let a deep moan escape his lips.

He was supremely embarrassed, but he couldn't help himself. It had seemed like an eternity of sucking, but it had been mere minutes before he creamed himself from the close attention paid to his dick. His knees were trembling and he couldn't feel his arms at all, but he certainly could feel the pounding of his heart against the bed sheet.

Brewster twitched and he gulped hard as the lips and tongues moved from his spent dick and started to rim his ass. He was moving to the rhythm of the attention he was receiving. His chest was sliding back and forth on the sheet and he was slowly rotating his hips back and forth as his hole was being loosened and softened. He groaned and moaned.

The trembling in his thighs increased as he felt the cool lubricant of the probing fingers that replaced the lips and tongue at his rim. He was being forced open by those fingers, which worked their way deeper and deeper, stretching him, preparing him.

He was panting and moaning, his attention so focused on those probing fingers, that he only barely heard the hoarse whisper.

'What?' he whimpered.

'Do you have something to ask?' The voice was deep, throaty. Very quiet, but intense.

'What?'

'Ask me for it.'

'What? Oh. Please, yes, please.'

'Please what?'

'Please . . . do . . . it . . . Ohh!' The nub of a forefinger had planted itself solidly on Brewster's prostate and he felt like he was going to jack off again, although he was just beginning to recover a hard on.

'Do what?' the voice hissed.

'Fuck me. Fuck me. Oh, please do it. Nowww!'

He had been prepared so slowly and methodically that he was completely caught by surprise at the swift brutality with which the fingers disappeared and big hands grabbed him by the hips and a thick, hard cock thrust inside him.

Brewster cried out, and groaned and begged and writhed under the firm grip of the furious assault. His crying for relief seemed only to excite his master, who pumped hard and dug deep. Brewster had no idea that Winslow had such strength and length and width and stamina in him.

It seemed to go on forever. When Brewster's knees could take it no longer and he collapsed fully on the sheet, his rider followed him, stretched full length on top of him and sucked on his neck as he thrust and thrust and thrust inside him.

Brewster was totally exhausted after his master's spouting and drifting off into a semiconscious state when he felt the restraints being loosened at the head of the bed and his wrists unbound, and he didn't stir again until well past dawn. And, of course, he awoke finally to an otherwise empty room.

Room Number 612 did, indeed, seem to be in the hotel's attic, Edward Winslow observed, as he exited the elevator and moved down the dimly lit hallway. And it definitely was in need of redecoration. Winslow had no idea that the FGCC had permitted its guest floors to go so seedy. He'd have to talk to Richard Warren about this.

After looking both ways down the hall to ensure he wasn't being observed, he turned the key to room 612, slipped inside, and shut the door behind him with a quiet click. He stood there inside the door, in the darkness, waiting for his eyes to adjust. He was breathing heavily, and his cock was already stirring, in anticipation of what he had campaigned for for nearly a year. He could hear the nervous breathing of his prey as well. Brewster had wanted to be taken while bound and blindfolded to assuage the guilt, but Winslow had been more than happy with this plan. Brewster's nervousness and fear fed the rising of Winslow's cock. He loved to dominate - in everything. That Bill had such a nice ass. Winslow could hardly wait.

His eyes were beginning to adjust. He could make out the outline of the bed and of a wooden arm chair off to the side. He extracted the leather restraints from his jacket pocket and took a step toward the bed.

'Ooff' He hadn't seen the fist coming at him from out of the darkness. It hit him midsection and sent him, doubled up on the threadbare carpeting on the floor. He was immobilized by the surprise and the pain in his midsection.

He didn't manage to even begin to struggle as he was stripped of his dinner jacket and lifted and thrown into the wooden arm chair, which rocked dangerously backward, kept from crashing back only by the hulking figure who had moved to behind the chair.

Winslow's arms were brutally jerked to behind the chair, and he heard the handcuffs snapping together. His own leather restraints were used to bind his chest to the chair back. And Winslow had only begun to regain his breath and presence of mind - to let out a scream of indignation - when tape was slapped over his mouth. Then he was blindfolded and totally under control.

The door clicked shut and he was alone. He was alone, bound to the chair, for hours, it seemed. Winslow seethed the whole time. What the fuck was Brewster up to? He couldn't just leave him here. The maids would be by in the morning and let him loose, and then he'd ream Brewster to within an inch of his life. So, he didn't want to be fucked. He would regret it. His future was toast. He might have cleared out before Winslow got free, but he'd pursue the bastard to the ends of the earth and make his life miserable. He'd ruin the fucker. He'd find a way to fuck him and then to ruin him.

Winslow had nearly nodded off, his inability to put his hundred-ways punishment of William Brewster into immediate effect, worn down by his spewing of bile within the restraints of the tape over his mouth, when he heard the door click open again.

He heard the movement in the room. The rustling of clothes. Then he felt the hands at his belt buckle. He struggled against the restraints as his pants were unzipped. His head snapped to the side as he was backhanded on the right cheek. And while he was immobilized, stunned by that, he felt his trousers and briefs being stripped off. His butt cheeks were cold against the wood of the chair bottom.

Winslow felt the cigar being taken out of his shirt pocket, and he barely had time to wonder about that before strong arms grabbed him under his knees, pulled his back down the chair slats, spread his legs, and hooked them over the arms of the chair.

Something cold was at his asshole, which puckered right up at the sudden attention it was getting.

The cigar. He was being probed by the Casa Blanca Jeroboam! God, what a sacrilege. The waste of an expensive cigar.

His ass was being worked well, though, and Winslow found himself moaning and groaning behind the taped mouth. That Brewster. What an actor, pretending that this frightened him. Winslow felt himself go harder than he ever had done before. This wasn't so bad.

The cigar was withdrawn and strong hands were under his knees again, lifting his hips up even farther out the chair. He heard the heavy breathing and the shared strain, as a big, thick cock started to work its way into his hole.

Winslow's pelvis was being swung back and forth and to the sides as the cock drove its way up into him. Both of them were huffing and puffing.

Winslow's assessment of Brewster skyrocketed. Boy that young man had balls. Worthy of his Mayflower ancestry. Worthy of being moved up faster at First Families Securities. It had been a risk, but Brewster had played it perfectly. Winslow was loving this fuck.

The fuck went on and on. It was a cruel fuck, an expert taking. Winslow shot off twice during the taking. He felt twenty years younger. This was far better an idea than the one he'd had - although he'd get his shot too.

A true American First Families performance. Pure-blooded American. Deep, thick, complete taking. Yessss!

Winslow was totally exhausted when it was over. He felt the handcuffs snap off and his bounds undone, and he just collapsed back into the chair, trying to pull himself together. When he reached up and pulled the blindfold off, he saw the light of rushing dawn filtering in through the dormer window. He was alone in the room. He painfully, stiffly raised himself from the chair and hobbled over to the cracked porcelain sink in the corner of the room. Using a threadbare washcloth, he cleaned himself as best he could and hobbled back to the chair; picked his briefs, trousers, and jacket off the floor; and put himself back together. It took him several minutes to smooth out all of the wrinkles, but he wasn't about to walk through the halls of the FGCC without looking exactly like what he was - a pure-blood descendent of the original Mayflower first families of the New World. Pure American down through the centuries. Protectors of all that was patrician Bostonian against the encroaching world of the dirty, impure immigrants.

When he was what he wanted to project, he left the room and went to the elevator. It had been a stupendous gamble on Brewster's part. But it had pleased Winslow. It had been years since he'd come twice in a single fucking. He'd be fucking Brewster, of course, but he had a whole new respect for the man. He certainly had balls.

Winslow didn't even acknowledge the presence of the Hispanic attendant who proceeded him out of the front entrance and flagged down a taxi for him. But after Winslow stiffly folded himself into the back seat of the cab and had made a sour remark about the immigrants who were driving the service cars those days, the attendant rose to his full height and flipped the departing taxi the bird. Flashing a big grin, he slowly pulled a moist and pungent Casa Blanca Jeroboam cigar out of his shirt pocket, lit it, and walked slowly back into the entrance to the world of the First Gentlemen's Covenant Club.

by Habu

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