This goes back a few years. Dan had completed his junior year in college, and was supposed to work for his father's investment firm in the Loop during the summer months. However, upon returning to Chicago from the West Coast, he pleaded with his father to give him the summer off, arguing that it was his last summer while still a college student. Even though this stupid argument begged the question – so what? – Dan prevailed. As such, he spent the summer drinking every night, and playing golf or lounging by various friends' pools all day.
It had been an eventful summer sexually. He and his friends typically spent their evenings in the bars downtown or in Highwood, a small town a few towns north of Winnetka known for its restaurant and (less so) bar scene. Being a normal college kid with normal sexual appetites, Dan had mounted his fair share of like-minded college women that summer.
But it went a little further than that. Having been converted the previous fall by Belinda Marcus into the pleasures and treasures an older woman can provide, Dan followed this obsession wherever it led him.
And in the early weeks of his summer break, it led him to Stacy Thomason, or rather back to Stacy Thomason.
Keith Thomason was a man that Dan had known since he was a child. Mr. Thomason and Dan's father were not partners per se, but they did partner up on a lot of investment deals and, over the years, their relationship turned social. While growing up, Dan recalled that Mr. Thomason and his wife at any given moment (he went through wives like people with incontinent bowel syndrome went through toilet paper) often spent Easter with his family. Similarly, his parents often vacationed with Mr. Thomason and his wife de jour.
During this particular summer (and for a few summers before it), Mr. Thomason's wife was Stacy. Like all Mr. Thomason's wives before her, she was considerably younger than his fifty-eight. Dan guessed that she was in her late thirties.
Stacy also mimicked Mr. Thomason's previous wives in stature and appearance, which is to say she resembled a Barbie doll, only not as tall. She stood a slight 5'6". Being one of the "ladies that lunch," she spent plenty of time at the East Bank Club (when she was in the city) or in the gym her husband had built in their Oak Brook home. Her legs were long and lean, her arms sinewy without being overly muscular. Her tummy was flat despite strong muscles honed through her daily exercise regimen.
Her narrow hips and trim waist gave light to the fact that she had never borne children. Stacy had spent her twenties and early thirties as a single woman, and had been (by her own admission) promiscuous to the point of being slutty. She had never settled down and thus had never given birth. But married now to Mr. Thomason, her desire for motherhood was strong indeed. Nonetheless, he already had three grown children and, at his stage in life, was not inclined to add another. With time, Stacy had thus abandoned her yearning for children in exchange for the comfortable life that Mr. Thomason could certainly provide her.
Dan first became acquainted with Stacy the previous summer when the Thomason's had invited his parents on their fifty-foot cabin cruiser for a party. Before going out that night, Dan had joined his parents on the boat, moored at Monroe Harbor, where he was introduced to Stacy for the first time.
She had come onto the rear deck from the cabin wearing what Dan considered an inappropriately short skirt that exposed her tan, lightly muscled legs. His mom later told him that it was simply a wrap covering her bikini bottom. A tight pink tank top hung on her torso, stretching across modest breasts. Short, dirty blonde hair highlighted a freshly scrubbed, girl-next-door face bearing high cheek bones, a pixie nose, lively bright blue eyes, and full lips. Except for a slight splash of pink color across her lips, her face was completely devoid of make-up. Dan had remained on the boat for only an hour or so, just long enough to down a beer and two, and then left to meet some friends in Lincoln Park.
Dan saw the Thomason's on a few more occasions over the next few months. Two weekends before he was to return to Los Angeles for his junior year, his parents were again invited to the Thomason's boat. Dan rode downtwon with them and planned to spend an hour or so visiting with the Thomason's before meeting up with some friends. When they stepped aboard the boat, Mr. Thomason was on the back deck with two other couples, drinking margaritas. He poured glasses for Dan's parents, but Dan declined, opting for a beer instead.
Mr. Thomason directed him to the galley refrigerator. Alone, Dan entered the cabin and moved toward the steps leading to the galley and the berths. When he reached the bottom of the steps, he found Stacy bent at the waist, grabbing a Coke from the refrigerator. She turned and stood straight when she heard Dan coming.
Dan barely recognized her. He wouldn't have thought that possible, given the fact that he had seen her five or six times over the previous two or three months. Yet there he stood, clearly confounded. Stacy had let her hair grow out (which he had noticed without much thought over the summer); it now reached two or three inches below her shoulders, still blonde but somehow . . . more blonde, brassy even. Her lips, full before, appeared even more so now; the previous faint smear of pink had been replaced by a glimmering red lushness.
The most alarming changes, however, were bolted to her chest. Gone were the moderate bumps that had previously adorned the woman's torso. In their place Dan found two massive breasts barely contained in – threatening, in fact, to spill over – a black bikini top. 'Sorry, Dan,' she had said sheepishly. 'I was just about to change into something decent.' And she disappeared forward to one of the berths at the front of the boat.
After Dan went back to the West Coast, he gave Stacy very little thought. Certainly, she had a delectable body, but she was fifteen or twenty years his senior, and was in any event married to one of his dad's good friends. But his encounter with Belinda Marcus changed those thought processes. Throughout his junior year, he became enthralled – obsessed maybe – with older women, and even more so with those that arrived with big diamond rings.
While Dan continued waiting tables at the World Café in Santa Monica, he continually scoped the tables for these wealthy wives, trying to determine from their style of dress and mannerisms whether he could bed them. On a few occasions – too few, in his own mind – he was successful. And as he grew more confident, his thoughts returned more and more to Stacy, the delicious little woman that had transformed herself the previous summer into the caricature of a trophy wife.
When Dan returned to Chicago for the holidays, it happened. A few days before Christmas, he met his dad at the East Bank Club for a game of squash and lunch. After lunch, they showered in the club's locker room and his dad, in a rush to make a meeting, left before him. Dan, leaving ten minutes or so later, saw Stacy sitting at a table picking at a salad. He paused, but ultimately approached her to say hello.
An hour later, Stacy Thomason was on her hands and knees on a bed at the Whitehall Hotel, her clothes strewn about the room. Her long red nails, gleaming in the bright light offered by a bedside lamp, tightly gripped a pillow, turning her knuckles white. Her artificially inflated tits – 38DD he later discovered – swayed to and fro beneath her torso, the thick nipples dragging across the 400-count bedsheet, rubbing them raw. Lightly made-up eyelids, screwed shut in sexual bliss, hid her bright blue eyes. Her mouth, bordered in the same bright red that first had stunned him the previous summer, hung agape. Grunts and groans escaped her slender throat, and foul language emphasizing her depravity tumbled across her lips.
Behind her, Dan was on his knees. One of his big hands was obscured by the long, platinum locks that were wrapped around it as he pulled her back onto him. Jutting from his waist, his thick cock skewered in and out of the married woman's permanently bald cunt. Copious amounts of fluid dripped between the two sweaty bodies as Stacy convulsed through her first of four orgasms that afternoon. Moments later, as the underside of Dan's cock slid forcefully along the edge of her pubic bone, coaxing scalding cum from his achy balls, only Stacy's adherence to the pill prevented an untimely (and embarrassing) pregnancy.
Three hours later, the two departed the hotel separately, leaving behind a bed from which the sheets had been ripped, towels dripping from the shower curtain rod, and the unmistakable stench of mixed sweat, vaginal fluid and semen.
Dan hooked up with Stacy two more times during that holiday vacation. When he came home for Easter, he told his parents that his flight wasn't to arrive until Friday afternoon. In truth, his plane touched down at O'Hare International Airport on Thursday afternoon. After making his way through the terminal, he descended to the basement and purposefully strode beneath the arrival and departure lanes to the O'Hare Hilton. Having already checked the voicemail on his mobile phone, he ascended the elevator directly to Room 954.
A few moments after he knocked on the door, Stacy pulled it open, her long, red fingernails curling around the edge of the door, the ostentatious diamond on her ring finger sparkling in the pale light cast throughout the hallway. 'God, I need your young cock,' she moaned as she kissed him hard on the mouth.
Her wet, pink tongue slithered between Dan's lips and her inflated tits smooshed against his chest. Before he had the chance to drop his bag, Stacy had fished his thickening cock from his pants and had wrapped her slutty red lips around the shaft, her lip gloss leaving a stain around the girth of him.
So it was that during the summer after his junior year Dan found himself the object of a married woman's affections. A few nights a week, he plied his charms in the bars of Highwood (he even checked out Hunter's once, looking for Mrs. Morgan) or Lincoln Park or Bucktown. But Stacy Thomason became his real obsession.
The last weekend in June, just before the July Fourth holiday, the Thomason's invited Dan's family to their home for a barbeque. Apparently, Mr. Thomason threw this party every year, inviting business associates, clients, and key employees. It was his way of saying thank you, and also of preserving good relations with clients.
Dan drove down to Oak Brook with his parents. With Dan at the wheel, his dad directed him off Interstate 88 toward the old Midwest Club. They were checked through the security gate and wound their way through the neighborhood to the Thomason's manor. A valet in front of the house offered to park the car, and Dan followed his parents into the house, the conditioned air a Godsend on this hot June afternoon.
A butler, hired to service the guests, directed them to the backyard where the party was being held. Dan sent his parents on their way, and stopped at the bathroom to relieve himself. When he stepped onto the back porch, the chatter of seventy or so people assaulted his ears and he inhaled the pungent scent of freshly cut grass. Getting his priorities straight, he first found the bar and got a bottle of Amstel Light. Taking a sip, he looked around for Mr. Thomason, and found him standing in a small circle of friends near a spit that had been towed in to roast the pig. Dan made his way over, and Mr. Thomason saw him approach.
"Dan! Great to see you," he lit up, extending his hand. "Glad you could make it."
"Glad you invited me, Mr. Thomason," Dan responded, pumping the older man's hand.
"Of course. Wouldn't be the same without you. Here, let me introduce you to these jokers. Gentlemen, this is Will's kid, Dan. Dan, this is Bob, Wayne, Stan and Rick." Dan shook hands with them all. "From right to left, they are my partner, a client of ours who has become a great friend, our attorney, and Rick here is one of my top guys. Been with me for years."
"Pleasure to meet you all," Dan said, shaking the last hand. As the men's conversation returned to business, Dan bowed out and found his parents. After being introduced – or reintroduced in some cases – to a handful of people, Dan wandered around the back yard for a while. He stopped by the spit to take a look; there weren't many pig roasts in Winnetka or Los Angeles. A few buffet tables were set up nearby, with a dozen or so round tables beyond that for dining purposes. 'Quite a spread,' Dan thought to himself, eyeing a small stage set up on the far side of the dining tables.
Sipping a fresh beer, he walked the hundred or so feet from the spit to a large flagstone veranda that surrounded the large, shaped pool; kids were splashing each other as two men in black pants, white shirts and bow ties attempted to erect a volleyball net across the width of the pool. He circled around the diving board just as a little brat did a cannonball into the deep end.
About fifty yards behind the pool was a guest house. Manicured lawn and landscaping separated the pool from the guest house, with a cobblestone path connecting them. The guest house itself was surrounded by tall oak trees, a small patio giving access to a sliding door that led inside. Dan continued to wander around the backyard. As he circled back around to another bar – this one located near the pool – and grabbed another beer, Dan saw Stacy giving directions to one of the waitstaff. When the young man scurried off with her instructions, she returned her attention to the coterie of women that she had been talking with.
Dan stood by the bar, observing her. She was dressed respectably today. A baby blue sundress hung just above her soft knees, adequately covering the inflated tit-flesh that had been installed on her otherwise trim torso. Gucci slides with open fronts covered her feet, exposing her sexy manicured toes. He watched as she took a sip of what appeared to be a mixture of vodka and lemonade; even from this distance, the bright red lipstick smeared on the rim stood out. Casually, she reached up and brushed the brassy hair from her face, the four-carat diamond mounted to her left hand sparkling in the sunlight.
"Keith's wife's a hottie, huh?" The voice startled Dan and brought him out of his reverie. He looked toward the voice and found Rick, one of Mr. Thomason's "top guys," standing next to him, scotch-and-soda in hand.
"Mmm," Dan dissembled. "Yeah, I guess. I never really noticed."
Rick scoffed at him before downing the rest of his drink in one gulp. "Bullshit, kid." He interrupted himself to burp, ordered another scotch from the bartender, and then continued. "Look at that fuckin' body. Jesus, what I would do to that." Clearly, Rick was drunk. Dan was not wise in the way of corporate politics, but he didn't think it was too smart to talk that way about your boss's wife.
"Uh, don't you work for Keith?"
"Yeah, what of it? Doesn't mean I can't notice that his wife is a little sexpot."
'A sexpot?' Dan thought to himself. 'Does this guy come from the middle ages, or what?'
Out loud, he mumbled, "No, I guess not."
"Besides, nothing would ever happen. She's too frigid. Believe me," he slurred, "I've tried to get into that bitch's pants and I always get shot down."
'What a fuckin' idiot,' Dan thought. 'Frigid, my ass. I've been in those pants half-a-dozen times.' What he said was, "Hmm. Well, I need another drink. See you around."
A little while later, Dan was talking to his parents and a group of his dad's business associates when Stacy found them. Dan's dad gave her a warm hug, and his mom planted a friendly kiss on Stacy's cheek. "Hi, Mrs. Thomason," Dan intoned when she turned toward him.
"Hi, sweetie." Stacy leaned into Dan and gave him a friendly hug, but whispered in his ear, "I love when you call me Mrs. Thomason." Her rose-tinted perfume wafted in his nostrils as she pulled back, and his cock twitched in his pants. "So," she smiled to the group, "I hope everyone brought their bathing suits. It's a fabulous day, and we've got the volleyball net set up in the pool."
Most of the crowd laughed and a slightly overweight man responded, "I don't think you want to see me in a bathing suit, jumping up and down."
With grace, Stacy laughed. "Don't be silly. You'll have fun. How about you, Dan? Bring a bathing suit?"
"I didn't." Dan took a pull from the bottle.
"Well, we have extra bathing suits inside. I'll get you one if you want to play."
"I might take you up on that," Dan responded, wandering off for a new beer.
The afternoon wore on, and the sun began to set. As it was about to disappear over the tops of the ancient oaks surrounding the property, a loud clanging sound emanated from around the spit and dinner was served. Dan, now in his bathing suit and a t-shirt, moved toward the buffet tables and, after filling a plate, found a table with his parents. The pool, previously occupied by volleyball players, emptied as everyone gathered for dinner.
As people finished eating, they got up from their tables and congregated around the stage, socializing and waiting for the band to begin. One of Mr. Thomason's employees – a younger guy – ran around recruiting people for another game of volleyball. Dan took him up on his offer, and jogged across the backyard to the pool and jumped in. A group of eight played a few games in the pool as the sun set completely, casting the backyard in darkness, illuminated only by the lights of the pool and the glow from the stage.
As the game died out, Dan remained in the pool with a few of the men who had played, including Rick. They all sipped at their drinks, dutifully topped off now and again by helpful waitstaff, and Dan listened to them talk about business or their golf games. After a while, the lights in the pool dimmed and then extinguished, and Stacy appeared at the edge of the pool, still in her sexy but conservative sundress.
"You guys gonna stay in there all night?" she asked with a bright smile. "The party's moved over there," she said, throwing a manicured thumb over her shoulder at the throng of people gathered around the tables and near the stage where the band was getting ready to play.
"Why don't you come in, Stacy?" Rick asked her, a leer in his voice.
"I don't think so, Rick. I'm entertaining," she responded somewhat sourly.
"That's what I mean," he slurred. "Get your ass in here and entertain us." Some of the guys in the pool looked at each other nervously.
"Don't be rude, Rick," she spat. "Why don't you get out of the pool and go find your little wifey?"
The other men began to move away and get out of the pool, but Dan stayed behind. "What's wrong, Stacy?" he inquired with a smile that only she could see. "Just throw on a bathing suit and join us for a while."
Stacy remained silent, considering. She looked over the backyard at all the partygoers, some still eating, others with full drinks in their hands, all waiting for the band to start. The waitstaff was doing their job without Stacy having to ride them. She shrugged her shoulders. "Okay. Let me go in and change."
When Stacy sauntered off toward the house, Rick turned to Dan. "What the fuck? I ask, and she says no and gets snotty. Some little punk like you asks and now she's inside changing? Fuckin' slut."
"Don't complain, Rick. You wanted her in the pool, and she's going to be in the pool," Dan explained. "Besides, I thought you said you never got into her pants."
Rick looked at him. "Yeah, so what?" he mumbled, or slurred, Dan couldn't really tell.
"So if even YOU can't fuck her, she must not be a slut." If Rick hadn't been so drunk, he would have easily detected the sarcasm dripping from Dan's voice.