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Consider this a sequel AND a prequel to Grandpa and the Nanny; you don’t need to read it to appreciate this – this one is set in 1999, during Norm and Pepper’s marriage, and details Will and Pepper’s continued affair.
Though he was in his late 50’s, Will Peters didn’t feel like he was aging particularly fast. Even though he was now alone, his wife having divorced him the previous year, he didn’t feel particularly alone. Maybe it was because he was living with his father Jack, to help the old man in his later years, or maybe it was the fact that his sex life was better than ever, with a bevy of gorgeous young women at his beck and call? Deciding to spend his newly divorced life in a series of casual relationships, Will found himself frequently dating women half his age. Hell, he started this habit even before he was divorced.
That was why his wife had left; having decided to surprise Will at his office one afternoon, she was shocked to find him getting his cock sucked off by two of his office secretaries and a particularly fine piece called “Pepper”. It’s good that his wife didn’t recognise the busty ginger beauty being chin deep in Will’s cock at the moment; but had she seen it was Pepper, her 25 year old son’s wife, sucking her husband off, she likely would have nearly fainted on the spot.
But Pepper was worth the risk. These secretaries were something else too, of course, having been the subject of Will’s long infatuation, with each having the tall, slender frame of a supermodel, their matching blonde hair and similar figures having earned them the nickname “the twins”. But the Twins were called that not only because they looked so similar; though tall and slender, Debbie, 21, and Suzanne, 24, had incredible c and d cup tits that were the envy of the office. On more than a few occasions, Will noticed half the office stop when one of the twins dropped some paper or stapler or something, with every straight man in the room vying for a glimpse at their tight asses, or for their blouse to reveal just a hint of their beautiful cleavage.
Though the Twins were a one in a million pairing, Will’s ginger daughter-in-law was irresistible. Her bright red hair, tiny frame and freckled skin drove him wild with every thought, and watching her cup her 32F breasts around his cock was still as exciting now as the first time she had fucked him with her massive tits. With the body of Charlotte McKinney, Pepper would have been the lust of any man of any decade, and she could have had any man. Though Will’s affair with Pepper started back when she was only 18, their passionate affair never lost its’ energy, despite the fact that it had been 7 years, and she had been married to his son for 4 years now. The 25 year old vixen still looked as tight and busty as the first day he had met her, and she loved to show it off to the men in the family.
Will would learn years later that his son Norm was suspicious of his wife’s affairs, but back in 1999, he was convinced he and Pepper were being perfectly discreet at their sordid affair. That is, until his wife decided to pop in after lunch one day. As Pepper works in a building near to Will’s office, he would often drive her into work in the morning, which acted as a perfect cover for their affair.
Usually it would only be a blowjob in the parking lot, or he would finger her as he drove along the highway, but that day Pepper had a different idea; she asked to come by his office to grab a coffee, since her office’s machine was broken, but managed to sneak into Will’s office without him noticing before he could get there to surprise him with a “gift”. Christmas was only a few weeks away, so she had sneaked in a special costume for her sugar-daddy in her bag…Stripping down in her father-in-law’s office, Pepper seductively leaned against his desk, dressed in an overtly sexy “Christmas Elf” costume. The flared green short skirt tied with a tight corset-top showed off her impossibly tight waist and shapely legs, but the much-too-tight corset top seemed tailor made to show off her chest. With the tight bustier on, the busty beauty’s frame was exaggerated by its’ tight form as she waited for his arrival, with her massive 32f tits nearly spilling out of their confining top.
Pepper heard Will’s voice approach, but then felt her blood freeze when she heard two female voices with him. Before she could do anything, Will and two gorgeous blonde women opened the door, to reveal Will’s daughter-in-law dressed in her sexy elf costume. Will dropped his notes and slammed the door behind him, forgetting that Debbie and Suzanne were with him, as he was supposed to be giving them some training.
Suffice to say, the awkward encounter of Will and these three women in his office somehow turned to laughter as everyone saw the absurdity of it all. But soon enough, that laughter turned to something else entirely.
When the Twins found out about Will and Pepper’s sordid relationship, they were noticeably turned on. Debbie’s hand escort kartal drifted to Pepper’s stocking-clad legs, while Suzanne sidled up next to Will. His arm instinctively wrapped around her waist. Before he knew it, his mouth was over hers, while the statuesque blonde reached for his erection through the fabric of his slacks.
Making his way to his desk chair, Will sat down, with Suzanne sliding down his body, her hands firmly placed on his hardening cock. On her knees, the model-esque beauty gently bit his cock through the fabric of his pants before biting his fly and pulling it down. Her hands massaging his thighs, she nuzzled his large cock through his boxers before reaching up and taking him in her hands. Massaging his member, she pulled him out of his boxers before taking as much of his length into her mouth as she could.
The demure beauty who Will had lusted for for so long was now feverishly and expertly sucking him off. He absent-mindedly reached down and fondled her d-cup tits as she worked his shaft. Pepper and Debbie at this point were watching Suzanne, each biting their lips and feeling very turned on at the site of the 24 year old secretary sucking off old Will.
Being so distracted by Suzanne, Will had completely forgotten about Pepper’s absurd costume, her massive tits hoisted up to her chin in the tight bustier of her red and green top. But at the sight of her as Pepper and Debbie kneeled on either side of Suzanne, Will felt like he could cum immediately. But the girls weren’t done with him yet, with Suzanne pulling away from Will’s cock for a minute, and aimed it at Pepper, passing the blowjob duties onto Will’s daughter-in-law. Pepper took up the mantle eagerly, immediately diving into deep-throating Will’s long member, as Debbie and Suzanne began to make out, still positioned at Will’s knees.
He felt oddly proud at the sight of these young vixens in a lustful daze at his knees, and instinctively said “Take out your tits, all of you,” in a commanding voice. Without breaking pace from sucking him off, Pepper popped her tits out of the tight cups of her costume. Suzanne and Debbie giggled, each wearing professional button-up blouses. Pulling away from their kiss, each girl unbuttoned their partners shirt, revealing conservative bras hiding their surprisingly large tits.
Before long though, the girls were back in their embrace, their large tits now pressed together as their tongues swirled in lust. Suzanne, not forgetting Will, reached over and massaged his thigh as she sucked on Debbie’s lips.
Pepper’s feverish blowjob was bringing Will near to cumming, but in a weird pause as she pulled away to jerk him to finish, Will felt the weirdest feeling of love for this girl. He knew it was wrong, and though it started as pure animal lust, the fact that wherever he went with her, these sorts of absurd and fun sexual madness would just erupt around them (this wasn’t their first time with a couple other girls joining in) made him feel more alive than he ever had before.
Looking in his eyes as she jerked him off, Pepper seemed to almost know what he was thinking, whispering “I love you too..” Will cupped her cheek in his hand as she slowed her pace, before they leaned in for a passionate kiss. As they pulled away, he heard her whisper “I want your baby…”
Will was shocked – not by what she said, but the fact that he felt himself get harder at the thought of knocking up his redheaded mistress. Plunging her mouth over his cum as he finally felt like he was going to cum, the group was rudely interrupted at this point by Will’s wife.
With a shocked look on her face as she watched three topless twenty-somethings kneeling in front of her husband, dozens of emotions flooded over her face in a moment as she stood and watched a shocked Will. Pepper didn’t seem to even notice, as she continued sucking, craving the taste of Will’s thick cum. At this point, Will’s wife was just watching as Will tried to stand, but was held in place by the redheaded beauty bringing him to the edge. As his eyes crossed and jizz sprayed into the back of Pepper’s mouth, Will’s wife looked shocked for a moment, before spinning on the spot and slamming the door behind her.
But Will’s body was too far gone at this point, and his eyes crossed as hot jizz flooded Pepper’s mouth. His trademark cumblast was in full force, and Pepper got a devilish idea, pulling her mouth off of his cock and aiming his spurting fountain at Suzanne and Debbie. The girls, though having felt incredibly awkward a moment ago as Will’s wife silently stared daggers at them, lost that reservation as Will’s cum splattered onto them. Turning to face his huge cock, Debbie’s 32C chest was coated by a huge blast of his cum, while some stray shots managed to land on her and Suzanne’s open mouths.
Even Will was surprised at the volume of this blast – he knew most women were shocked at how much men in his family could cum (Pepper had confided in Will that both Norm and Jack, maltepe escort Will’s Father, came nearly as much as Will – though he wouldn’t admit it, Will was secretly turned on by the fact that this young beauty was a cumslut for three generations of his family), but he soaked the girls to the point that it looked like they had been the focus of a bukkake scene.
But after he sunk back into his seat, his balls drained and his partners cleaning the cum from each others faces, the reality sunk into Will that his marriage just ended. But then he looked back down at Pepper, and thought about her comment, and felt his cock twinging again at the thought of being a free man again.
As Suzanne and Debbie licked the cum from each others’ bodies, Will heard a knock at the door, and before he could put himself away, another one of the office CEO’s opened the door. Steve, Will’s co-workers, froze when he saw the scene, as the three beauties looked up at him, still coated in Will’s cum. Steve just looked over the scene, got a cocky grin on his face before speaking,
“Damn Will, you got Debbie AND Suzanne? And here I thought last Thursday was special for the three of us, girls…” He winked as Suzanne and Debbie blushed, as Will realised these little tarts must have been making the rounds at the office. Suffice to say, he took a mental note to give them a raise.
Steve sidled out, giving Will and the girls some privacy. Before long, Will was hardening again, as Pepper sat on his lap, both watching the Twins break out in a full-on make-out session, their bodies glistening with cum as they massaged each others’ exposed tits while passionately swapping spit.
Before long, Pepper looked Will in the eyes and silently positioned herself over his cock. In a risky move, she elected to forgo panties with this costume, knowing they’d only hinder Will. Positioning herself over his fully erect cock, Pepper silently slid down his length, taking his girth with an audible sigh of pleasure.
But this wasn’t meant to be a gentle fuck. Pepper wanted Will’s cum deep inside, and they were both too turned on for foreplay. Within a few pumps, Pepper was bobbing up and down on his cock in a feverish pace, her curly red hair and massive tits were bouncing in the air with each pound. Holding her by the ass and standing up, Will positioned her tight ass on the edge of his desk and began pounding her, hard. It was as though he finally felt free, knowing his wife was fully aware of his cheating, but Will was fully giving it to his 25 year old daughter-in-law/mistress/cumslut, and before long felt another cumblast welling inside. Pushing himself deep inside her tight pussy, he unloaded a huge cumshot inside her, filling her up with his warm, sticky jizz.
Wrapping her arms around Will’s neck as he unloaded deep inside her, Pepper’s huge breasts were pressed against his chest as he felt her cum from the force of his jizz, quivering in pleasure as she leaned into his body, his thick member still deep inside.
“Maybe that did it…” Will whispered,
“If not, we’ll just have to try again…” Pepper replied.
As Will sat back down, Pepper still leaning against the desk, he closed his eyes and leaned back, feeling physically drained. But before long, a new tongue found its’ way to his cock, as Debbie sat up to clean up his sticky member.
Will knew he wasn’t going to cum again, with his cock staying at half-mast as the perky 19 year old blonde licked his length and sucked on the head. He couldn’t tell if she was trying to get him hard to fuck her, or just loved the taste of his jizz, but either way, he leaned back and enjoyed her wet mouth, as Suzanne and Pepper coalesced against the desk, the two beauties melting into each others arms in a tender embrace as they watched Debbie lick Will clean.
“Can you get hard for me again?” Debbie innocently asked as she held his cock in one hand.
“I’m trying my best, but I might need a break hun. I’m not as young as you!” She grinned, and replied
“Well, I’ll just keep trying to change that…” As she continued to gently massage his spent cock.
Suffice to say, she eventually won him over. But the story of Will’s affair with Debbie was far from over.
When Will got home, his wife was gone without as much as a note. He only ever heard from her through her lawyers after that day, as she quickly severed all ties, in spite of their 25 year marriage. But he knew he was at fault, and was compliant with all aspects of the divorce.
He truly had loved his wife, but the passion had fallen away in recent years. Somehow, he convinced himself she had to have been having an affair too; still a beauty at 45, Will fell for her sophisticated elegance. But the passion had left, and now Will was alone in his big house, just before Christmas.
Knowing his father was coming to stay for the holidays brightened his mood a bit, although he knew that that his fathers’ age of 86, Will might be playing caretaker to pendik escort bayan the old man for the holidays. Little did he know how wrong he would be.
Jack, Will’s father, came by the week before Christmas, and before long was asking about Pepper. After Jack and Pepper fucked in her change room as she got ready for the wedding to Norm four years ago, she had never left his mind. Pepper, always having had a weird place in her heart for old men, loved his passionate groping of her massive rack, and, moreso, loved his monstrous cock. So whenever Jack came by to “visit his grandson”, she
would inevitably end the night with him cumming in or on her in some way. She knew Will was fine with it – though she loved playing with Jack, she loved Will most, more than her husband arguably.
She would never admit it to her husband, but compared to his father and grandfather, Norm was a shrimp, and she craved the meat Jack and Will had to offer.
On the Friday before Christmas, Norm and Pepper came by to visit by surprise; Will and Jack were more than thrilled to see Pepper, but Will knew that Norm was only coming by to ask for a favour. He tended to do this.
After some light banter and teasing of Will about his recent divorce (Norm seemed to be taking his parents’ divorce very well), Norm got down to brass tacks. He had been given the responsibility of organising his office Christmas party, but had forgotten until the last minute. The party was the next night, and he hadn’t hired a Santa. He explained that a couple interns agreed to play the part of Santa’s helpers and take the pictures, but he couldn’t think of a better Santa replacement.
“So Dad,” Norm said in a pleading voice to Will, “Would you consider playing Santa?” It’s just for a few hours, and I know how great you are with kids – and after that, there’s free drinks at the party, and you’re more than welcome to stay.”
“What about your grandfather? I can’t leave him alone all day while I go and party.” Will was trying to think of any reason to skip this damn party. Play Santa? He wondered if he had let himself go a little too far, if people thought he looked like St. Nick.
“Grandpa can come along too, I’m sure he’d have a great time too,” Norm was desperate, and figured his grandfather couldn’t do any harm. Little did he know, his wife perked up at mention of Jack coming along. She had been craving his thick cock, and loved the thought of keeping their naughty affair going in somewhere as public as her husband’s office. Jack eyed her over as he sat in on the conversation. The old dog knew he was going to have Pepper on his cock by the end of the night, and he couldn’t help but grin.
“See! Grandpa already looks happy to come!” Norm said, noticing the smile on Jack’s face.
“Oh, I’ll definitely be happy to come!” He replied, glancing over at Pepper in the process. Will almost rolled his eyes at Jack’s cheesy line, fully well knowing that his little mistress would be sucking Jack off that night. But Norm was completely oblivious, just continuing to talk to Will.
Pepper bit her lip seductively at Jack without Norm noticing, and he got a devilish idea. Standing up, with his half-chub distinctly noticeable through his slacks, Jack excused himself to go make a drink in the kitchen, looking straight into Pepper’s eyes as he said it.
The kitchen looked on to the living room, with a bar between the two. Jack walked over to the bar, with Norm’s back facing him, and started to get the blender out. Taking the hint, Pepper excused herself to use the bathroom just as Jack started the blender. Without Norm noticing, Pepper slipped behind the bar, immediately onto her knee at Jack’s feet. Norm was the only person who was completely oblivious, with Will hardly believing what he was about to see.
From Will’s perspective, he could only see his father standing behind the bar, using the blender for much too long. But his expression said it all, as his eyes crossed from the blowjob he was likely receiving. Behind the bar, Pepper had quickly pulled open Jack’s drawers and swallowed his cock, taking it as deep as her little mouth could handle. It clearly had been a while since Jack had cum, since he started to rapidly facefuck his grandson’s wife, thrusting hard against her open and eager mouth. Her thick red lips were driving him wild, and soon he was thrusting so hard, the back of her head was lightly knocking on the cupboard. Completely unaware at this point, Jack was nearly cross eyed as he pounded her. Norm, about to turn to look for the source of the noticeable banging, was distracted by Will.
“Our washer has been acting it, I put a load in earlier.”
“I’m about to put a load in myself!” Jack responded, clearly out of breath. Norm didn’t notice, and turned to continue talking with Will.
As Will and Norm talked about the party, Jack was getting close to finishing. He never could last long with Pepper, especially when she wore tops like the one she currently had on, a overly tight black v-neck band t-shirt, her gorgeous cleavage plainly on display. She knew the shirt was a few sizes too small for her 32f breasts, but she loved the looks men would give as each movement threatened to burst the shirt at its’ seams.
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