Loading...Roy Sharpe felt like his life was turning around, after having gone through a rough patch. Roy had gotten married a couple of years ago, and right after he made Mindy his bride, he lost his job as the economy tanked.
Now newly employed, Roy felt like a man once more. As a representative for a winery in the Finger Lakes region, Roy was hired to work all of the wine tastings and festivals in Eastern New York and New England, pouring samples and extolling the virtues of the products he was pushing.
The couple that owned the vineyard, Claude and Carly Persaud, had taken Roy under their wing and seemed to be quite fond of him, always telling him how pleased they were to find a young man so eager and willing to bust his butt for their company.
Although Roy had gone out on his own for a few shows, Claude told his young protege that he was going to go with Roy when he was going to work a few major wine festivals in the Saratoga Springs area in mid-September.
“It’s close enough so I don’t feel guilty leaving for a couple of days,” Claude said when he told Roy of his plans. “If Carly needs me I can get back here within a few hours. Plus, I want to see how you work. You’ve been getting so many favorable comments about your presentation that I’ve got to see you for myself.”
Since Roy liked Claude a lot, and looked up to his boss a great deal – not only physically but for his wealth of knowledge about wines in general – Roy welcomed the companionship. It was tough always being in strange cities, far away from his wife and alone. Having Claude with him would not only be a learning experience, Roy figured, but it would also help him cement his position in the firm.
*********
“Like they say,” the man said. “You only rent it.”
Roy had certainly noticed the man who had sidled up next to him at the trough urinal in the men’s room at Gaffney’s, the bar that Roy had been drinking at with his boss after the first wine tasting at the nearby performing arts center had ended.
Despite trying to ignore the person as he did his own business, Roy realized that old habits die hard as he found himself powerless to stop his eyes from drifting over as the man beside him relieved himself. The torrent of urine splattered noisily in the metal basin, but what Roy was looking at was the source of the spray.
The man had pulled out his manhood and after pulling and stretching it a couple of times, let it go after he began urinating. So captivated was Roy at the size of the man’s cock that hung unsupported while the owner put his hands on the wall in front of him, that Roy hadn’t noticed who it belonged to until he heard the deep bass voice of his employer resonate in the small bathroom.
“Uh – yeah, that’s right,” Roy mumbled, glancing up and feeling relieved when he saw that Claude was staring straight ahead, apparently unaware that Roy had been looking at his cock. Roy wiggled his dick and tucked in back in his pants quickly, turning and washing his hands before exiting the room and returning to the table in the outdoor garden that they had been drinking at.
“That was close,” Roy whispered to himself as he went back and drained his rum and coke.
Claude was working his way through the crowd to get back to their table, and Roy couldn’t help but look at his employer differently now. Funny after seeing another guy’s private parts, Roy always looked at the man differently, he mused, still not believing what he had seen.
His employer was a big man indeed, Roy realized, figuring him to be about 6’4″ and a fairly solid 225 pounds or so. It only figured that he would be big all over, but after getting a look at Claude like that, Roy knew that he would never forget what he had seen.
Even now, working his way through the crowded patio, Roy found himself picturing the middle-aged man naked, and hating himself for his weakness. Ever since he had been married, Roy had managed to keep these desires out of his mind, but now after an innocent glance, it was all coming back.
“Get a grip,” Roy muttered to himself as Claude eased himself into the chair across from him, unable to keep from imagining that gigantic cock of his hidden under the clothing.
What would he have told Mindy if his employer caught him gawking at his penis and decided that he didn’t want some queer working with him? Not that Roy considered himself gay, of course. His wife didn’t know about his weakness. Hell, Mindy had been so innocent and naive when they met, that she had thought that giving a blow job had meant actually blowing on his dick. What would she say if Claude had caught him looking at his private parts like that?
“Sorry, babe. I got fired for staring at my boss while he was taking a leak,” Roy imagined himself saying to his wife. “Yeah, it was a great job, but I’ve got this thing about big cocks, and Claude’s was a whopper, so I stared at it and got canned.”
No, that wouldn’t do, Roy realized, so when Claude suggested they get back to the hotel so they would be ready for another long day tomorrow, he happily agreed.
“Yeah, I’ve had plenty enough to drink today,” Roy told Claude as they walked up the street to the Hilton where they were staying.
**********
“Feel free to use the shower first,” Claude told Roy after they got back to the room they were sharing. “I’ve got to call Carly and see how things are back at the homestead.”
Roy nodded and took his things into the bathroom, closing and locking the door behind himself before stripping down. Standing in front of the toilet, Roy looked over at the full length mirror on the back of the door.
Mimicking the way Claude had been at the bar’s urinal, Roy pulled on his dick a couple of times before he let go and stood there posing while letting his pee go.
“How come they always do that?” Roy whispered to himself as he looked at his reflection, before answering his own question. “Because they can.”
Roy knew that you never saw guys built like himself standing there in public, brazenly flaunting their stuff. It was always the well endowed guys who stood there with their hands on their hips and showed the world what they had, and why not? Roy had seen his share of well hung guys in his life, but Claude’s was something else altogether.
Even Roy had to chuckle when he looked at himself, imagining what Claude would have thought if he had seen him just now in that pose and had gotten a glimpse of his tiny dick. He looked like Pee Wee Herman, for crying out loud.
In the shower, the warm spray felt refreshing, and after a minute or so, Roy noticed that he had been lathering himself very thoroughly in one particular area, causing his dick to become erect.
“Might as well do it now,” Roy mumbled, setting down the soap and grabbing his dick between his thumb and index finger, because he knew he could never get to sleep feeling like this.
Roy stroked his dick, which had blossomed to its full five inches rapidly, while imagining being in bed with Mindy, but the image didn’t take, because no matter how hard he tried, Roy kept seeing Claude.
How big was Claude when he got hard? Roy couldn’t keep himself from wondering as he worked his hand up and down his slippery organ. From what he had seen of it flaccid, when erect it would have to be an even more impressive sight. Having met Carly, Claude’s wife, who was a petite woman much like his own Mindy, Roy shuddered when he thought of the gigantic Claude mounting her with that prodigious organ in an aroused state.
Who knows, Roy thought. Claude’s an old guy – probably in his early 50’s. Maybe he couldn’t even get it up anymore, Roy theorized momentarily, before dismissing the notion. Bullshit. Claude was all man. Roy could spot that a mile away. That confident demeanor of his employer let the whole world know that he was a real man’s man and not some wimp.
For instance, Claude would never be standing in a hotel room shower like he was; jacking off while fantasizing about another guys cock, dreaming about kneeling in front of him and skinning back the foreskin on that massive organ and taking it into his mouth, and letting him grab his head and skull-fuck him until he came, bathing his throat with a tsunami of cum.
Roy found himself leaning against the shower wall as his cum spat onto the tiles, and after he stopped shaking he made sure that there was no evidence of his self-abuse before stepping out and drying off, before getting his pajamas on.
***********
When Roy emerged from the bathroom Claude was on the phone, talking to his wife. His boss was naked except for a towel tied around his waist. Luckily Claude had his back to him, so Roy went over to the bed closest to the wall and slipped under the covers.
Claude’s legs were long and fairly smooth, which was a definite contrast to his upper torso. Claude had a thick coat of hair on his chest, black sprinkled with a little gray, and even had some hair on his back.
He was in good shape for a guy his age, Roy noted. A bit thick around the middle, but his shoulders were broad and muscular, and his arms were well defined and solid, with faint traces of an old tattoo on his bicep barely visible through the hair that covered it.
Roy closed his eyes as Claude ended his call, ashamed of himself for what he was thinking. There he was, a 24 year old married man, checking out a man twice his age. A man, no less! If Claude knew what was going on in his head he would think he was gay or something.
On the other side of that bathroom door, Roy heard the shower being turned on. Claude was stepping behind the curtain now, letting the spray rain over his body. Because he was so tall Claude probably had to stoop down to get his head wet, and Roy imagined that the big man was probably cramped in that tiny stall.
Mr. Loomis had been tall too, Roy reflected. Probably just as tall as Claude, even if he wasn’t as burly looking. He was the scout master who had taken Roy on a special hike to a secluded lake in the mountains.
“To get away from the kids,” Mr. Loomis had said. “Give us men a chance to be alone. Maybe we’ll discover something new and exciting.”
Roy remembered how scared he was when Mr. Loomis had suggested they skinny dip at the desolate lake, and when he saw Mr. Loomis naked Roy tried to get out of disrobing as well.
“We’re both men,” Mr. Loomis said when he saw Roy staring at his private parts with his mouth open and his eyes bulging, and after Ross had gotten naked he remembered how nice the older man had been.
“No reason to be ashamed of yourself,” Mr. Loomis had said, his eyes sparkling as he watched Roy strip down. “You’re quite a handsome young man.”
“Your dick is so big,” Roy remembered saying, not believing the size of the penis that swayed so lazily between the man’s legs, and while it had been impressive, in retrospect it wasn’t all that extraordinary. Nothing like Claude’s, that was for sure.
“That’s not very important, you know. Oh heck, you’ll probably be as big as I am some day – probably bigger,” Mr. Loomis had assured him.
That hadn’t happened, of course, Roy knew, but it didn’t really matter during that special summer. Mr. Loomis was patient and caring, and loved him in every way possible, teaching Roy the pleasures that only two men can share.
There had been other men after Mr. Loomis, and not all of them so nice, but Roy found himself helpless to resist when they came on to him, and come on to him they did. It was like Roy had a sign on his back announcing how easy he was.
When he had met Mindy, Roy had found a way out of that life. Mindy liked him, and he liked Mindy as well. She wasn’t demanding, and because she had lived such a sheltered life she didn’t really have anybody to compare Roy with, and that comforted him a great deal.
The thump that accompanied Claude turning off the shower jolted Ross out of his reminiscing, and he threw the sheet up over his head and closed his eyes and tried to get to sleep.
The door of the bathroom opened up a moment later, and Roy found himself unable to resist squinting from his vantage point as his employer made a dramatic entrance into the room, the steam from the bathroom billowing behind Claude as he strode into the room.
Claude was toweling what little hair remained on his head, fearlessly walking into the room fully exposed. Roy gasped when he saw Claude naked, because that glimpse of Claude’s penis in the men’s room was only a hint at how incredibly well-endowed Claude was.
What Roy noticed first was that Claude had apparently removed the pubic hair from the perimeter of the base of his cock. Roy himself had done that a few times, when Mindy had complained that his pubic hair would get stuck between her teeth, but there was no way any mouth could get near the base of Claude’s member for that to happen.
The stump might be a better word to describe the base of Claude’s penis, because while his cock became somewhat normal in thickness as it tapered down to the glans, the girth of the stump of his cock was stunning, with the sinewy roots and veins disappearing along the way to the tip.
The impression of the ridge of the bulbous glans was visible through the foreskin, which was long and completely shrouded the head of his manhood, depriving Roy of a glimpse of it, but Roy had seen enough.
When Claude turned toward the dresser, Roy took the opportunity to quietly turn toward the wall and try once again to drop off, although his dick was so hard that Roy knew that he would be heading to the bathroom to relieve himself as soon as Claude fell asleep.
**********
Roy wasn’t sure whether he had fallen asleep or not, but when the cool air hit his back, his eyes popped wide open. The sheet had been pulled down, and then the bed shook, as if a 6’4″ 200-plus pound man had just climbed onto the queen-size mattress along with him.
Roy felt his heart begin to race out of control as the bed wobbled with the inching over of his employer until the warmth of Claude’s torso was against his protege’s backside.
“You’re so tense,” Roy heard Claude whispered huskily into his ear. “Relax.”
“Mr. Persaud?” Roy began to say, but Claude cut him off.
“Claude,” the older man said, correcting Ross as his hand came up to the younger man’s shoulder and slid around. “We aren’t working now.”
“Claude. You’re – we’re married men,” Roy protested as he felt Claude’s fingers undoing the top buttons of his pajama top, and Roy shivered when Clause’s hand slip inside of the shirt.
“I know we’re wearing rings,” Claude said, her long, plump fingers sliding over the young man’s smooth chest and finding his nipple, tweaking the small bud while he nuzzled into Roy’s neck. “We both also know that it’s all for show. I know what you really want.”
“Please,” Roy whimpered, feeling his nipple prick up in response to Claude’s touch.
“I guess your wife doesn’t know about you yet,” Claude said. “She will in time. They usually find out. My Carly knows – hell, when we interviewed you she told me what kind of guy you were just by talking to you. She’s got a sixth sense about things like that. You can’t keep it a secret forever. Matter-of-fact, I was just telling her about you when you were in the shower.”
Roy made a choking sound as Claude’s fingers deftly undid the rest of the buttons on his pajama top, and Claude chuckled at Ross and his terrified reaction.
“I told Carly that I showed you my cock in the bathroom of that pub. Told her that she was right about you, and that when you looked over at my cock you practically got whiplash. She suspected you liked dick the first time she met you.”
“I didn’t mean to look,” Roy protested. “It was just a…”
“You wanted to look,” Claude said. “Although I did love you trying not to. That really turned me on. And you liked what you saw, didn’t you?”
“Claude,” Roy whined, cringing when he felt the pulling at the top of his pajama bottom, and the clicking sound when the snap opened echoed in the room.
“Let’s see what you were trying so hard to hide back there in that men’s room,” Claude said softly, opening the folds of the pajamas and letting his fingers slide down Roy’s lower stomach. “Mmmm… you’ve only got a little hair down there, don’t you? Do you shave down there? No? It feels so silky and soft.”
Roy groaned as he felt Claude’s hand toying with his pubic hair, pulling and twirling the modest tuft of curls while his body shuddered. Ross felt his dick shriveling up and trying to retreat into his body the closer Claude got to it.
“You’re not scared, are you?” Claude said softly, continuing to tease the area around Roy’s dick without going any lower. “Do you want me to stop?
Just say the word and I will.”
“I didn’t think so,” Claude continued after a long moment of silence, and with agonizing slowness, his hand left the nest of pubic hair and went lower.
Roy whimpered when he felt Claude’s fingers on his dick, a sharp contrast to the purring or growling noise his employer made after he found what he was looking for.
“Found a peanut,” Claude said with a snort when his fingers got hold of the shriveled dick his hand had been seeking.
“Mmmm… nice,” Claude sighed, sinking his teeth gently into the earlobe he had been whispering toward and leaning into the shivering body of his employee. “Don’t be scared. I like what I’m holding. Let’s get you situated.”
Roy felt Claude’s hand on his shoulder, pulling him onto his back. His pajama bottoms were being tugged lower and then Claude’s fingers were holding his dick again, pulling on it in an attempt to get him hard.
“Relax,” Claude suggested, and in the semi-darkness he saw the young man had his eyes closed and a pained expression on his face.
The older man moved onto his knees, his objective clear. His mouth took in the modest stem, bringing his mouth up and down hard on the toadstool while his undulating fingers rolled Roy’s nuts around.
Claude felt the dick in his mouth begin to lengthen and thicken, slowly at first and then surging when his tongue began to work on it as he sucked on it passionately. The older man was pleased when he took his mouth away for a second to see what he had done, and the sight of little monolith straining for the ceiling made him smile.
Claude cupped the rigid dick in his palm and pulled it up toward the owner’s belly as his face swooped down. Taking first one nut, and then the other in his mouth, Claude rolled the little nuggets in his mouth individually before opening wide and taking in the entire sac.
Roy squirmed around as his nuts churned around in Claude’s mouth, pulling at the sheets while looking down at his employer practically inhaling his scrotum. Their eyes met in the murky light, and when they did Claude’s head came up from between Roy’s thighs.
“I know what you want,” Claude said, letting go of Ross and moving up to the head of the bed on his knees, the hand that had been holding Ross now on his own manhood, pulling on the elongated cock and bringing it up to the face of his protege. “Here you go.”
Claude’s fingers peeled back the foreskin, exposing the bell-shaped glans that had a reddish brown hue a few shades lighter than the dusky hue of the rest of the organ. Claude rubbed the tip against the lips of the younger man until they parted.
“That’s it,” Claude sighed as Roy took the head of his member into his mouth, the younger man’s eyes widening as Claude eased more of his dick in. “That’s my boy. That’s my little cocksucker.”
*******
Roy tried not to gag as Claude coaxed more of his enormous organ into the younger man’s mouth, Claude chuckling as he felt his protege’s reluctance disappear as soon as his cock met Roy’s lips.
“That’s it, Roy boy,” Claude said, pulling his member out from between the eager lips and dropping it on the younger man’s forehead and offering him his balls. “Work my nuts too.”
Claude rode his employee’s face as if it was a saddle, grinding his hips as he straddled Roy’s face. Roy had cupped Claude’s ass with his hands and squeezed his buttocks while he eagerly suckled on the meaty orbs.
In the dim light, Claude could see the picture of his employee’s wife on the night stand next to the bed. She was a plain looking woman, and Claude wondered what she would think if she could see her husband now.
Already Claude was thinking of the possibilities. He had met Mindy Sharpe already, and discovered that she had been as meek and timid as her husband. That stereotypical librarian type really turned Claude on, and Claude felt his cock begin to stiffen, partly as a result of his employee’s efforts as well as his fantasizing about fucking Roy in the ass while the prim and proper Mrs. Sharpe watched in horror.
**********
Claude was on his back, watching Roy work feverishly at his hip, his mouth going up and down Claude’s stiff cock while his hand worked on the part he couldn’t fit in his mouth. Claude’s hand was down between Roy’s legs, squeezing his little nut sac in between sending a finger into his employee’s ass.
Roy had already cum a few minutes earlier, a result of jerking himself off while Claude was straddling his face and force-feeding him cock, and his dick was hard again while continuing to go down on his employer.
His jaws ached as a result of having to accommodate the size of Claude’s cock for what had to be over 15 minutes so far, but Roy was so excited that he hardly noticed the discomfort. Roy wanted Claude to cum. He yearned to feel the hot spunk that was going to spray his throat, and when he felt the surge going through the shaft and heard Claude groan, he got his wish.
Roy choked a bit when the first blast went sailing into his throat, but he kept sucking as Claude continued to erupt. His cum was hot and plentiful, and as the spurts turned into dribbling, Roy savored the tart and musky flavor as Claude’s cock began to deflate at last.
“You’re good,” Claude sighed as he pulled Roy’s mouth off of his cock. “Damn good. We’re going to have a great weekend, you and me.”
Roy let Claude embrace him, the warmth of his employer’s hairy chest comforting him, and then Claude crawled out of Roy’s bed and over to his own.
Why? Roy kept asking himself that question as he stared at the ceiling, listening to Claude’s breathing begin to get slower and deeper as he fell asleep. Why did he have to look at Claude in the men’s room? All of this would have been avoided. Instead, he found himself being drawn right back into his old ways.
********
Over an hour later and Roy was still wide awake. They had a busy day ahead of them tomorrow and Roy knew that he needed to be sharp and on his toes, but he couldn’t stop thinking about the man in the other bed.
Silently, Roy rolled out of his bed and walked toward the bathroom to get a drink. He would have made it too, if it were not for the fact that Claude was sprawled on his back in his bed, and the sheet had slid down to his knees. Having had his eyes open all night, Roy could see everything all too clearly.
There it was, Roy thought as he stared at the cock he had suckled on earlier in the evening. Now as limp as a dishrag, the long bronze tool hung over towards Claude’s hip, while between his splayed thighs, his over-sized nut sac dangled almost down to the bedding.
Roy bumped into the casing of the door, which brought him out of daze. Closing the bathroom door behind him, Roy went about the difficult task of peeing with a throbbing erection, having to pull his toy cannon down hard so that he hit the target accurately.
After washing his hands, Roy glanced at the little travel satchel that Claude had left in the bathroom. Nothing remarkable, for the most part. The usual things were there like a razor and deodorant, but what caught Roy’s eye and made him shudder was the enormous tube of Anal-Glide in the bag.
“Omigod”, Roy gasped as he shied away from the satchel as if it were radioactive.
The thought of that gigantic cock, which had stretched Roy’s mouth out so far that his jaws still ached, trying to penetrate him anally, made his heart skip a beat.
He had taken other men that way, and a couple of them rather well endowed, but nothing to compare with Claude. To think that his employer had brought that lubricant, and actually expected to use it on him in that way, was frightening to Roy.
Yet when Roy emerged from the bathroom, his dick was still hard, and when he passed by his employer and saw that Claude had rolled over onto his side in bed, he found himself easing into the bed next to him.
Claude’s body was so warm, and his back was so hairy, that Roy really wanted to cuddle up next to him. What would Claude say? The more Roy thought about it, the more he found himself drawn closer to his employer, until his chest was against Claude’s furry back.
Roy’s heart was racing, and when he felt the tip of his dick graze the crack of Claude’s ass, it went into overdrive as Roy fantasized about the possibilities. Not about actually putting his dick in Claude’s ass, because his stem would never reach far enough between his beefy buttocks to achieve penetration.
The only time Roy had actually been able to have a man anally, the other guy had been even skinnier than he was. No, Roy wasn’t thinking about the actual act, but was wondering what it would feel like to just slip his dick in between Claude’s ass cheeks. They were so soft and full.
Please don’t wake up, Roy kept thinking, as Claude moved slightly upon contact. Claude’s body had moved so that he was almost inviting Roy to do it, and when Roy eased closer to his employer, his dick slipped right between his buttocks.
Roy had to bite his lip to keep from cumming. The crevice was so warm, and the head of Roy’s was so sensitive that he could feel the hairs that grew between Claude’s butt cheeks. Then, just as quickly as they had parted, Claude’s ass clenched, squeezing Roy’s dick between the fleshy pillows.
“Oh!” Roy cried out, realizing that Claude was awake.
Claude reached back and grabbed Roy’s hand, bringing it around to his crotch. Roy’s hand grasped onto Claude’s cock, which was so limp it was like holding jello, and as Roy milked the colossal organ he felt his orgasm racing through him.
Claude’s husky laughter accompanied Roy’s cumming, as his young protege’s dick spurted wildly into the crack of his ass, and Claude’s vise-like grip on Roy’s dick did not let go until he went limp and it fell out.
“Sorry,” Roy said softly.
“You liked that, didn’t you?” Claude asked, and when Roy admitted he had, Claude chuckled.
“Good. Now take care of the mess.”
“Yes sir,” Roy said, but Claude stopped him when he started to go get a towel.
“Not that way,” Claude told Roy.
**********
Roy knelt behind Claude as the hulking figure got up on his knees, exposing his semen filled ass crack and the dangling cock and balls that swung lazily between Claude’s thighs.
Roy had tasted his own spunk before, but never like this. Now he was being told to service his boss – to clean the mess he made. Even in the dim light Roy could see the load that he had unleashed all over the hairy crevice.
His cum tasted rank as it mixed with the musky aroma of Claude’s bottom, but Roy went as the milky mess with a passion. His tongue swabbed up and down the crack, while Claude moaned his approval and spread his legs wider.
“That’s it,” Claude groaned. “Get your tongue way back in there. Get the ring. Work that tongue around the knot. Milk me while you’re licking my asshole.”
Obediently, Roy’s hands reached under and started kneading Claude’s balls while he pushed his face deeper into the crack of his employer’s ass and pulled on his dick. Roy stretched Claude’s flaccid hose as hard as he could, yanking on the rubbery cock with both hands now while his tongue and jaws throbbed with pain.
Soon Roy was just pushing his face up and down while he kept his tongue out, swabbing Claude’s anus as best he could while praying for him to cum, even though he wasn’t even hard yet. Finally, just as Roy was about to say he couldn’t do it anymore, he felt a surge go through Claude’s semi-turgid manhood, and then his employer let out a loud groan.
Seconds later, Roy felt Claude go limp again in his hands, and as he pulled his face out from between Claude’s buttocks, Roy could see the stringy thread of cum dangling from inside the crinkled foreskin and down to the bedding, where a small pool of semen rested.
“Good boy,” Claude said, climbing out of the soiled bed and over to Roy’s former one. “Let’s get some sleep. Tomorrow’s a big day.”
Roy watched Claude’s hulking figure move over to the other bed and pull the sheet over himself while turning his back to him. Roy was still on all fours, his tongue and jaw hurting so bad, but as he looked down at the semen Claude had deposited on the sheet, he couldn’t resist bending down.
Roy’s mouth took in the still-warm seed, and after his tongue got most of the rest of it, Roy eased down into the damp bedding and pulled the sheet over himself, savoring the nectar in his mouth as breathed in deeply as the aroma of the bed’s former occupant filled his head.
***
Roy woke up first in the morning, showering again and getting dressed quietly so that he could go down to the hotel’s hospitality suite for some complimentary breakfast. Roy stayed down there for over an hour, not wanting to go back up to the room. Too much temptation there.
Claude appeared around 8, looking refreshed and happy. He nodded toward Roy before getting a cup of coffee and a couple of pastries and going his employee at his table.
“Early riser, I see,” Claude said, holding the danish in his meaty paw and looking around the room at the other diners. “I was too, if you know what I mean. Woke up with a raging hard-on. Too bad you weren’t there. I’ll bet you could have taken the edge off for me.”
Roy felt his neck burn as his boss spoke too loudly for his liking, but Roy said nothing and stared at his coffee, and before too long Claude told Roy it was time to go over and set up.
The day went by in a blur. There was an even bigger crowd today than yesterday, and it seemed to Roy that he didn’t stop moving and talking all day. If it wasn’t for Claude being in the cramped space behind the table with him, he might have been able to take his mind off of things.
The problem was that in that restricted area, there was no way to avoid contact with each other, since they were constantly reaching around to get to things. The physical contact seemed innocent enough to the customers, and much of it was, but Roy came to realize that much of it was instigated by Claude.
The more Roy thought about it, it seemed that yesterday Claude had been always brushing up against him as well, but yesterday afternoon things were different. Roy hadn’t known the way Claude was back then, so all of the back slapping and shoulder squeezing were just harmless camaraderie.
“They really like the Riesling, don’t they? Claude remarked as the event wore down and they began to clean up and break down their display.
“Uh yeah,” Roy said. “We were lucky we didn’t run out until the very end.”
“Keep them happy and keep them wanting more,” Claude said, his meaty hand kneading Roy’s shoulder. “Right? You seem tense today, Roy boy. Maybe you need a massage.”
“No, I’m okay,” Roy said as he rolled up the drapery that had lined the table.
“I figure we’ll go have a nice dinner somewhere in town, and then head back to the room early,” Claude thought aloud. “Dinner at seven and then back to the room. I’ve been looking forward to tonight all day, haven’t you Roy?”
“Um – kinda worn out,” Roy said nervously.
“You’ll get your second wind,” Claude assured his employee. “I’m sure of it. Just curious – are you a screamer?”
“A screamer?”
“Yeah. Are you the kind of guy that does a lot of squealing when you take it up the ass, or are you the type that just grunts?” Claude asked, opening the trunk of the car so that Roy could toss the stuff in. “There’s no wrong answer.”
Roy didn’t reply, and instead just got in the passenger side of the car and let Claude pick the restaurant. Roy was taken to a funky little place called Hattie’s that served what had to be the best fried chicken Roy had ever tasted, but his mind was elsewhere, and Claude was no help.
“How do you like it usually, Roy? Rough?” Claude asked as he devoured a piece of pecan pie.
“Mr. Persaud,” Roy said, trying not to make his voice whine like it had a tendency to do when he was embarrassed or nervous, and as he looked around the cramped and filled dining room Roy thought that everyone could hear his boss speaking.
“Nobody’s listening to us,” Claude said, waving his hand at the surrounding diners. “They’re all busy trying to get laid themselves later. You and I – we don’t have to worry. We know what’s going to happen after dinner, don’t we?”
He was right, Roy thought. When they got back to the hotel room his employer was going to have his way with him. Claude was going to do whatever he wanted to him, and when he was ready he was going to take him anally. It was already decided. Roy had no choice.
As the two of them walked through Congress Park before heading back to their hotel, Claude called his wife on his cell phone. After briefly chatting, Roy was shocked when his boss handed him the phone.
“Hello Roy,” said the chipper voice back at the winery.
“Hello Mrs. Persaud,” Roy said nervously.
“Carly,” his co-employer corrected. “We should be on a first name basis – especially now. Are you boys having fun?”
“Uh – yes Mrs. – Carly,” Roy mumbled. We really moved a lot of Riesling. In fact all of the whites went over really well.”
“That’s good to hear, Roy,” Mrs. Persaud said softly. “I’m very glad you’re taking care of my husband so well. He’s told me what a great time he had with you last night, and after what he told me he’s planning to do to you tonight – well, let’s just say that I wish I could be there to see it.”
Roy almost dropped the phone when he heard what Claude’s wife said, and when he looked over at his boss Claude’s wicked grin let him know that while he couldn’t hear what his wife was saying, he had the gist of the conversation.
“Roy?” Are you still there?”
“Uh – yes,” Roy mumbled, jumping when Claude’s meaty hand clamped down hard on his thigh briefly.
“You see, I have company of my own right now,” Carly Persaud said. “She’s in the bathroom right now but she should be out any… wait – here she is now. I’m sure she would like to speak to you. Here.”
Roy heard the phone being passed and then the familiar voice of his wife came through.
“Honey?” the meek little voice squeaked.
“Mindy? What are you doing there?” Roy asked.
“Carly called me up because she knew I would be all by myself this weekend, and when she invited me over I decided to go,” Mindy said.
“But how did you get there?” Roy asked, knowing that Mindy couldn’t drive.
“Carly sent a car for me,” Mindy chirped. “I’m going to spend the night. They have such a beautiful house. I just had a glass of Gurr…”
“Gurtzweiler,” Roy said.
“That’s it,” Mindy giggled. “And we’re going to have dinner now, and after that we’re going to go into their hot tub.”
“Mindy?” Roy said, the connection breaking up as he tried to desperately figure out what was going on.
Mindy getting taken over to the Persaud’s house, and spending the night with Claude’s wife? What was going on? And Mindy was so modest she didn’t even own a bathing suit.
“Breaking up honey,” Mindy said. “Have fun. I’ll see you tomorrow.”
“So tell me what’s going on back at the old homestead,” Claude said, taking the phone from a stunned Roy and putting it away.
“Mindy. She’s at your house, with your wife.”
“I know.”
“They’re going to have dinner and then going into the hot tub,” a bewildered Roy mumbled.
“And then what?”
“That’s all she said.”
“Well, maybe little Mindy doesn’t know what’s going to happen after the hot tub,” Claude said with a chuckle. “Or in the hot tub. But I know.”
“Your wife? Mindy?” Roy said before breaking up with laughter despite his nervousness. “My Mindy? Claude, you don’t know Mindy.”
The very thought of his prudish bride doing anything with another person – especially a woman – was so absurd that Roy had to laugh.
“And you, my friend, don’t know Carly,” Claude said, his beefy hand coming down on Roy’s shoulder and practically lifting him up with him as he rose. “I suspect that in a little while – maybe 9 or 9:30 – your blushing bride will be in my bed with Carly, doing things that would make your little dick spurt if you saw it.”
“Insane,” Roy said.
“We’ll find out tomorrow morning, won’t we?” Claude concluded. “Enough about them. The rest of the night belongs to us.”
***
Roy was on his hands and knees while Claude walked around the bed to get to his suitcase, his cock swinging in front of him like an elephant’s trunk. On the sheets below Roy was the cum that had spurted out of his now-limp dick, the result of Claude’s fingers probing him.
First one of his boss’s fingers, and then the second was forced in. It was the third digit that had made Roy cum without a hand being laid on his member.
“You’ve got a tight asshole, Roy,” Claude remarked, waving a purple toy in front of his face before climbing onto the bed behind Roy. “This will help loosen you up for me.”
The feel of the vibrator against his anus, the end of it undulating around along with the whirring noise, made Roy shiver, and when Claude pushed the tip of it inside of him, he let out a loud groan.
“That’s it, Roy” Claude said. “You like that up your ass, don’t you?”
“Too big,” Roy grunted. “Tearing me up.”
It felt like the twisting vibrator was like a cement mixer inside of him, churning and undulating slowly while Roy’s body did the same thing.
“Nonsense,” Claude said. “I’m sure you’ve had cocks that big up there before. You like the big cocks, don’t you Roy?”
Claude pushed the vibrator a little farther into Roy’s rectum and left it there, climbing off of the bed and coming around to the head of the bed before getting on next to Roy’s beet-red face.
“I asked you if you liked the big cocks, Roy,” Claude said, waving his flaccid tool in Roy’s face and slapping him playfully on the cheek with it.
“Why are you doing this?” Roy whined, the crinkled ridge of Claude’s foreskin inches away from his mouth.
“Because I like it,” Claude explained. “Because you like it too. That’s why you’re here.”
“No. I need – need my job.”
“Job?” Claude said, glancing down at the vibrator still working away unattended in his employee’s ass. “This has nothing to do with your job. You’re good – real good. You’ve got real marketing skills. You’re on all fours, with a vibrator rammed up your ass, getting ready for me to fuck you hard, because you want to.”
“No,” Roy cried.
“If you don’t want this, say the word,” Claude said, wiggling his dick as he spoke. “Say, Claude, I don’t want this. Say it and I’ll be over in the other bed asleep in ten minutes and we’ll pretend none of this ever happened. You’ll have your job – hell, I’m giving you a raise regardless. Just say the word. Say stop.”
Roy looked up at Claude who knelt before him, and said nothing for over a minute. Finally, Roy’s mouth opened, but not a word came out. Instead, Roy’s lips parted as Claude brought his massive penis up to him, retracting the foreskin to reveal the plum-sized head of his member.
“You give great head, Roy,” Claude said as he watched his organ slide into Roy’s mouth. “You know how to handle a big one alright. Imagine how good this is going to feel up your ass soon.”
Roy’s eyes bulged as his lips went down the dusky shaft as far as they could before the tip of it hit his throat. Claude’s cock looked like a tree trunk where Roy’s lips could not reach, with the veins like roots around the shaved base of his manhood.
“Ever had ten inches inside you before, Roy?” Claude asked, taking his cock out of Roy’s mouth and leaning so that his balls slapped against Roy’s face.
“No,” Roy whimpered, licking the pendulous ball sac and the underside of the cock above them.
“Is it going to be too big for you?”
“No,” Roy gasped before taking the bloated head of Claude’s cock back in his mouth and eagerly sucking on it.
“Good,” Claude said, his fist working around the part of his cock that Roy’s mouth could not reach. “I’m hard. It’s time.”
***
“Want to see your face our first time,” Claude explained after putting his young protege on his back, with a pillow under the base of his spine elevating Roy’s ass for Claude’s pleasure. “I want to watch your expression when you feel my cock go inside of you.”
Claude kept rubbing lubricant all over his swollen organ while looking down at Roy. Roy’s slim, almost hairless body was glistening with sweat already, his tiny dick hard and curled back up to his tummy with the little wrinkled nut sac danging helplessly below.
Roy’s puckered ring was oozing with lube as well, and was still a bit opened up from the work the vibrator had done, but Claude knew that it was still going to be a tight fit. How many times had he gotten to this point only to have the guy chicken out, or simply not be able to take him?
More times than not, Claude sadly mused, but Roy was going to be different. He could feel it, and when he climbed between Roy’s thighs, which Roy himself was holding wide open for him with his hands, Claude knew that he never wanted anyone more.
Claude let out a moan as he pushed the head of his cock into that tiny orifice. Roy would have screamed, were it not for the handkerchief that was stuffed in his mouth, but even with that, the squealing sound Roy made was plenty loud.
“Yeah!” Claude grunted as he pushed more of his cock into Roy, whose face was so strained and distorted that he was unrecognizable, and the tears that streamed out of the corners of his eyes were real, but he took it like a man.
Claude moved half of his cock in and out of Roy’s ass with a gentleness that surprised both of them. Claude wanted this to last, so he took it slow, because he had wanted to cum the second his cock entered Roy’s hot cavity.
Claude’s eyes left Roy’s, which were rolled back into his skull, and traveled down his lithe frame. On Roy’s belly, ropes of cum had been sprayed, and the cum was in the little nest of pubic hair as well, the result of Roy cumming at some point.
This sight was too much for Claude, and when he could fight it no more he gave in, easing as far into Roy’s ass as he could as letting go. Roy could feel the warmth of Claude’s seed as it filled his bowels, and when he looked up and saw the hulking figure above him, sweat raining down from his body and onto him, he could see the ecstasy on his boss’s face as he came.
Claude let out a long exhale before leaning down and kissing Roy’s forehead and getting back up on his knees. He pulled his limp cock out of Roy’s cavity, grinning when he saw the gaping hole that remained, big enough to drop a golf ball into.
“Let me help you,” Claude said when Roy tried to get to his feet, and he wrapped his arm around his wobbly-legged young employee and helped him into the bathroom.
They peed together at the toilet, the two streams crossing as they tinkled from the two wildly different dicks, and after they were done Roy put his arms around Claude, hugging the furry giant tightly.
“That was really good,” Roy said. “Thank you.”
“Let’s take a shower,” Claude suggested.
The shower was a tight squeeze for the two men, but it helped Roy stay on his feet as Claude soaped his body, By the time Claude was done washing his very sore anus, Roy had regained a little of his strength, enough so that he was able to lather up his boss.
Before Claude moved under the spray, Roy ran his hands up and down Claude’s muscular arms, and Claude cooperated when Roy lifted his arm, holding his hand behind his neck as Roy leaned forward and buried his face into his mentor’s unwashed armpit.
Roy licked and chewed the spray of hair under Claude’s arm, savoring the taste and scent of his manly musk, his tongue lapping at the fur throughly before going over to Claude’s other armpit. Roy felt his dick get hard as his senses were overwhelmed by Claude’s manliness which oozed out of his pores.
Roy’s soapy hands reluctantly scrubbed Claude’s armpits clean and then worked the foam into his hairy chest, and although it hurt to kneel, Roy managed to scrub his employer’s cock and balls in between giving his genitals a lot of love and affection.
“You want it again, don’t you?” Claude asked Roy as they dried each other off outside the stall.
“Don’t know if I can,” Roy confessed, looking at the cock his towel was drying, and even in the flaccid state the dusky brown organ looked imposing. “I’m really sore.”
“You can do it,” Claude said, spreading his legs so Roy could work the towel around his balls. “Look at your dick – how hard it is just thinking about it.”
Even with their great differences in height, Claude’s cock hung down right around Roy’s crotch, and Claude smiled when Roy put his boner against his cock and rubbed them together, the young man’s pale stem dwarfed by his uncut tool. It was as if Roy was turned on by the outrageous differences in the sizes of their cocks, almost as excited as Claude was himself.
“This time, I won’t be so nice to you,” Claude warned, his breath in Roy’s ear. “After I get you ready, I’m going to take you from behind. I’m going to mount you like an animal, and fuck you until you beg for mercy.”
“You like hearing that, don’t you?” Claude hissed, watching Roy’s chest begin to heave as he rubbed the heads of their cocks together, the acorn head of Roy’s dick mostly hidden under Claude’s foreskin. “You want me to grab your hair and shove your face into the mattress. You want me to grab your nuts in my hand like a vise. You want… ahhh!!!”
Claude looked down at Roy’s dick spurting cum all over his cock, the milky ropes of seed spraying all over his brownish organ until Roy was spent.
“You’ve cum three times already tonight, and I haven’t even touched you yet,” Claude said with admiration. “That little pecker sure has got a lot of spunk. Now let’s get back into bed and get busy again.”
***
Roy’s eyes winced at the bright sunlight that streamed through the open window of the hotel room, and the sound of Claude talking on the phone brought him back to reality. he was in a hotel room in Saratoga Springs, and his body ached from head to toe, particularly his anus.
Roy’s tender orifice seemed like it was on fire, and it felt like he still had Claude’s cock inside of him. The second time had been unreal. Claude did exactly what he had told him he would do.
Claude was savage and relentless. He had mounted him just as he said he would, and there was little of the tenderness of their first coupling. Claude was brutal, his cock impaling Roy hard and deep. Claude started thrusting fast from the start, and then went into overdrive, his cock working like a jackhammer into Roy’s rectum while he crouched over him like a predator.
Roy could not stop the tears anymore than he could stop himself from ejaculating wildly when Claude had reached around and yanked at his dick with all of his might, and when Claude finally came himself, filling his bowels with his hot cum, Roy’s only regret that it hadn’t lasted longer than the 15 minutes or so it did.
“What time is it?” Roy asked, wincing when he tried to get up on his elbow.
“Eight, sleepy head,” Claude said, throwing the sheet off of Roy and laughing. “Is that thing always hard?”
Roy looked down at his morning wood and shrugged, finally crawling out of the bed and waddling over to the bathroom while Claude laughed.
“Looks like you just got off a horse.”
“Never be able to walk right again,” Roy mumbled as he took a leak under his employer’s watchful eye.
“I was just comparing notes with Carly,” Claude said. “Told her that I nailed the sweetest, tightest ass in the world, and she told me about her and Mindy. Carly is crazy about your little lady.”
“Claude, I know you’re just trying to get a rise out of me,” Roy said as he washed his hands and
went to get dressed. “Mindy would never…”
“Let’s see,” Claude said. “After dinner, they went into the hot tub, and before long Carly’s hands were all over your wife. She said that she was surprised how easy Mindy was. It was almost as if she had been hoping for it.”
The thought of Mrs. Persaud and Mindy was far-fetched, but Roy found it arousing in a way. Carly Persaud was an attractive woman with a nice figure for a middle aged woman, and Roy thought seeing that blonde naked wouldn’t be hard to take, but Mindy with her? She wouldn’t even look at X-rated movies.
“Right,” Roy said sarcastically.
“Don’t believe me?” Claude said. “Let’s see, Mindy has dimples on her butt, and she had the cutest little titties. Carly said that it was the first time she had made love to a girl with smaller breasts than hers, and Carly’s are really small. She said Mindy’s tits are about the size of lemons – all nipple almost – and when she lays on her back they almost disappear. Looks like a boy that way. Bet you like that.”
Roy stopped getting dressed and stared at his boss, not believing what he was hearing, but the description was spot on and it didn’t stop there.
“That little church mouse is a tiger in the sack too, according to Carly,” Claude continued. “For such a meek girl, she turns into an animal between the sheets. Big bush on her too. Carly loves that untrimmed jungle of Mindy’s.”
“How in the world?” Roy asked, the room spinning as his mind tried to comprehend all of this.
“And all that hair under her arms?” Claude said. “Mindy told Carly that it was you that insisted she not shave her armpits. Mindy was embarrassed about it until Carly told her that she loved it. Reminded her of that intern we had at the winery one summer from Paris. It makes Mindy look more androgynous, and that probably helps you get it up when you see her laying there all hairy with those little swells for titties.”
“Don’t act offended,” Claude said, pointing at the bulge in Roy’s underwear before Roy yanked his trousers up. “You love the thought.”
“Did Mrs. – I mean Carly, tell Mindy about you and me?”
“No, if you want to tell her, that’s up to you for now,” Claude said. “And Mindy doesn’t know that you know about her, so you can handle that however you want.”
“It’s all so – too much to take in at once.”
“Just think of how much more interesting your life has become this weekend,” Claude said. Last weekend you were a closet gay living with a closet lesbian.”
“Mindy’s not gay.”
“You were her first guy, but she had several female lovers growing up,” Claude said. “Probably just like you, she got married to avoid the stigma. You two love each other, but like Carly and me, you’re more like sisters and brothers than lovers.”
Was it true, Roy wondered, and tried to think of a time when he ever felt with Mindy like he had over the last couple of nights with Claude, and couldn’t.
“In time, it all will come out,” Claude concluded. “You two will tell each other your secrets, and will be open about it all, just like we are. Eventually, maybe all four of us will get together. Just imagine the possibilities.”
“You mean…”
“Think about it. The two girls watching us, and us watching them go at it. Imagine your Mindy getting drilled by Carly with her strap-on, like she did last night, and then having your wife watch me fuck you in the ass.”
“I don’t know if I could,” Roy admitted.
“And then there’s you with Carly,” Claude continued. “I told her about how cute your little dick was, and she was dying to try it out. As for your Mindy, I have to admit the prospect of sticking my cock into that furry little twat really turns me on. Can you picture that?”
Roy winced when he thought about Claude trying to put his huge cock into poor little Mindy, and Claude slapped him on the shoulder before grabbing the luggage.
“Plenty of time for that,” Claude said. “Time to get back home.”
***
“Tell me all about your trip, honey,” Mindy chirped as Roy hobbled into the house. “What’s wrong?”
“Just tired, and I was on my feet a lot,” Roy lied, his sore anus throbbing as he moved. “It was really a good trip. I got to know Claude really well.”
“He seems like a nice man, and Carly – well, I think she’s great. She so smart and everything. I think we’re going to be great friends.”
“Funny you would get along that well with her,” Roy opined, “Seeing like she’s old enough to be your mother.”
“But she doesn’t act it,” Mindy said. “She’s fun and really nice, and she said that Claude really thinks you’re great. I’m so glad that you two are hitting it off. You finding this job came at the right time for us.”
***
Roy turned off the bathroom light and went into the bedroom, and was startled to see Mindy on her back in the bed, stark naked and smiling at him with her hands behind her head.
“What’s gotten into you?” Roy said, not used to seeing his usually modest wife openly displaying herself like this.
“You, hopefully,” Mindy said, giggling like a schoolgirl. “Unless you’re too tired.”
Roy was tired and sore, but as he shrugged off his pajamas, his dick was hard. He could see the tiny tell-tale signs on Mindy. Signs that she had really been busy last night, and things that he wouldn’t have noticed if he hadn’t known.
Tiny marks around her neck, and a little fingernail scrape on her thigh. Thinking about Claude’s wife with her face in that wild jungle of brown hair between Mindy’s legs made his cock twitch with delight.
Claude was right. He had never noticed it before, or maybe he had and refused to acknowledge it, but on her back, Mindy looked a lot like a guy. Mindy’s virtually flat chest and the thick tufts of hair that filled the hollows of her armpits excited him, and always had.
“Carly invited me to stay over at their place next weekend,” Mindy said as Roy climbed into bed with her. “Claude is going to make the trip to New York City with you, if you didn’t know that already, so that way I won’t be alone. Okay?”
“Sure,” Roy said, and as Mindy gently stroked his stiff dick, he imagined what it would be like.
Roy imagined Mindy staring in awe at Claude’s gigantic organ, and could almost see her trembling hand reaching out to touch something so unlike anything she had ever seen before.
Roy pictured Mindy getting Claude hard and covering Claude’s cock with lubricant – maybe even helping to put Claude’s cock into his ass herself, and then Mindy watching with Carly as Claude drilled him into the bedding like a feral beast.
It was only a fantasy – for now – but it was enough to keep Roy hard as he moved his dick into Mindy’s wet pussy and began humping wildly.
“Oh, Roy!” Mindy yelped, and as they thrust their bodies into each other, Roy couldn’t help wondering what Mindy was thinking.
Was Mindy fantasizing about Carly, or thinking only of him? What was he thinking of – WHO was he thinking of as he lowered his face under Mindy’s arm and nuzzled at the thick jungle of hair while his wife squealed with delight?
Roy knew the answer to that. The two of them would have to talk, eventually. Claude had been right about that, just like he had been right about everything else so far.