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.
