North Shore Ass Whore

Dan spent last weekend up at his parents' house in the suburbs. It was one of those dead weekends. Many of his friends were out of town, working, or too tired to go out. On Friday before he left, he called Steve Morgan's cell phone again in one last ditch effort to try to get something going, but was greeted only by voicemail. He hung up without leaving a message, threw some clothes in a backpack, and drove up to his parents'.

They were surprised to see him lounging on their couch in the television room when they returned from a dinner party later that evening, but were nonetheless thrilled at the prospect of having their baby boy home for the weekend. Dan joined his parents Saturday for breakfast and helped his mom around the yard with what was left of the morning. When he checked his voicemail around lunchtime, Steve had called.

"What's up? It's Steve. Got your first message and saw you called again. Sorry for not getting back to you. I'm up in the 'burbs this weekend. My parents are having an engagement party for Kari and her fiancé tomorrow, so I came up this morning to hang out with them. I'll give you a call next week."

"Hmph," Dan said to himself, deleting the message. Before he and his dad left for the club for golf and a few drinks, he tried Steve again.

"Hello?"

"Steve?"

"Yeah. Dan. What's goin' on?"

"Same as you, my friend. I'm in Winnetka for the weekend."

Steve laughed. "How funny. What are you up here for?"

"Nothing goin' on downtown, so I got out for the weekend."

"Yeah, I thought it was going to be kind of a dead weekend, so I came up today instead of tomorrow just to hang out."

"Let's grab a few drinks later. I'm going to the club with my dad in a little bit. Why don't you meet us there around seven or so."

"Well, I'm having dinner with my parents tonight. We're just going over to Hackney's, the one on Lake. Why don't you meet us over there after the club? We'll have dinner with my parents and maybe go to Meier's for a few drinks." Dan paused.

He hadn't seen Mrs. Morgan since their coupling in that suite at the Ritz so many months ago. He recalled the event vividly: the parting of the sexy top to reveal her artificially inflated tits; the smoothness of her shaved cunt as the wine bottle slipped between the folds of her lips; her red lips wrapped around his thick cock, saliva dripping down the shaft.

Absently, Dan reached for and readjusted his thickening cock. "Um."

"Come on! It won't be that bad. My parents are pretty cool. Mom's mellowed out a lot," Steven chided him.

"I know," Dan responded defensively. "It's not that. I just don't want to intrude on a family thing."

"Don't be ridiculous. It's just me and my parents. Kari and Jake won't be there, and Betsy doesn't get in until tomorrow morning. We'll be there around seven, maybe seven-thirty. See ya there," Steve finished, clicking off.

Dan stood there a minute, holding his Blackberry. More images raced through his brain. She bent over the bed, his cock thrusting into her from behind; her bald cunt lowering itself onto his shaft, each inch disappearing into her slowly; her blond hair spread out on the comforter, his cock squished between her saline-injected tits, her manicured nails and wedding and engagement rings just inches from his leaking cock.

But this could be awkward. How would Mrs. Morgan react when he appeared at Hackney's. Would she be embarrassed? Sheepish? Or would she play it off with her typical bitchiness? Probably the latter. 'This could be fun,' Dan thought to himself. He shrugged internally, and then bounded up the steps to his old bedroom, rummaged through his closet for clothes appropriate for the club, and changed.

* * *

Outside the club, Dan gave his dad a quick hug before jumping in his car. "Say hi to the Morgans for your mother and me, and be safe. If you drink too much, give us a call. One of us will come and get you."

"No problem, Dad. You guys have fun tonight. I'll probably be late, so I'll see you in the morning." Dan turned the key in the BMW's ignition, backed out of the parking space, and drove up to Lake Street, then over the Edens Expressway to Hackney's. He was running a little late; it was almost eight when he pulled into the parking lot. He saw the Morgans' Range Rover and pulled into an open stall two spaces down.

Entering the restaurant, he quickly found them in one of the side rooms; they and another couple were the only patrons in that room. As he approached the table, Mr. Morgan rose, extending his hand.

"Good to see you, Dan," he said heartily, vigorously pumping Dan's hand. Mr. Morgan was a tall, well-built man, graying at the temples. His grip was firm and confident. His cheeks were a little red, hinting at the fact that he had already downed a few cocktails.

"You, too, Mr. Morgan. It's been a while, huh?" he said, circling the table toward Mrs. Morgan. He flashed an innocent smile her way. She returned it with a fake one.

"Too long, kid," he heard behind him. "You oughta come see us more often."

"Hi, Mrs. Morgan," Dan said with a broad smile. "You look fantastic as ever."

"Thank you, Dan," she responded. The sarcasm dripped from her tongue, or so he thought. Perhaps he was just reading into things, knowing the things about her he knew, knowing that her husband and son didn't know them.

After giving her a chaste hug, but one that lingered just a little longer than necessary, Dan sat, his back to the wall. Steve sat across from him, Mr. Morgan to his left, Mrs. Morgan to his right.

"Let's get the waiter over here and get you a drink," Steve suggested, turning around and signaling the waiter. When he appeared, Dan ordered a drink and the Morgans began placing their dinner order. Dan added a simple cheeseburger to the order.

The Morgans and Dan engaged in small talk for a while, waiting for their meals, getting caught up with each other. How's work? Same old, same old. Any girlfriends? Here and there. How are your parents doing? Great; they asked me to say hello. That sort of thing. Though careful not to stare too long in Mrs. Morgan's direction, Dan could not help but drink in her beauty.

Throughout their conversation, she twirled a wineglass between her slender elegant fingers, tipped with a French manicure. Given the summer months, her lean, tanned and slightly freckled arms were bare to the conditioned air. Her blonde tresses were pulled back into a tight ponytail, revealing teardrop-shaped platinum earrings dangling from her earlobes. Dan had never seen her hair pulled back in such a manner, but liked it; it highlighted the high cheek bones and sensuous jaw line of her face. Her baby blue eyes danced from her husband to her son to her son's best friend as the conversation flowed, pausing more often than not on the young man seated to her left.

"Don't you agree, Donna?" she heard her husband ask.

"I'm sorry, honey. What did you say?" Mrs. Morgan raised her wineglass to her shiny red-stained lips. As she did, her wedding rings caught the light of the restaurant, sparkling in spite of the dimness.

"It's great to have all the kids home for the weekend, don't you agree?"

"Of course, honey," she responded, setting her empty wineglass on the table, lipstick smeared along the side of the rim closest to her. "It doesn't happen often enough, what with Betsy living in San Francisco now."

When their meals arrived, conversation was reduced to a minimum as the Morgans and their guest cleared their plates. Occasionally, Dan cast a sideways glance toward Mrs. Morgan, trying to be discreet but almost groaning in his throat. The top two buttons of her white cotton oxford blouse hinted at a respectable cleavage within, the fabric stretched tautly across her huge tits. Though it would require him to stare too long to confirm it, Dan thought he detected the slightest suggestion of thick nipples pressing through her bra, almost tenting the blouse. He shifted his legs in an effort to relieve his discomfort.

When Mrs. Morgan finished her meal, she began to rise. "Excuse me for a moment, gentlemen," she pleaded and walked from the table toward the rear of the restaurant.

"Women are incredible," Mr. Morgan intoned once she was out of earshot, taking a long pull from his scotch and soda. "If I had to go to the bathroom, I'd say, 'Excuse me, I gotta go to the bathroom.' But not women. They simply say 'Excuse me.'"

Both Steve and Dan chuckled at his observation, but Dan barely paid attention. Over the top of his glass, he watched Mrs. Morgan as she strode away from them. A conservative khaki skirt that stopped three-quarters down her thighs, swooshing slightly back and forth as she moved, hid her tight little bottom. Tan, lithe legs extended from beneath the skirt, ending in a pair of Prada slingback heels.

She soon returned amidst talk of the Cubs and the White Sox and the coming football season. The table ordered another round of drinks as their light conversation continued. When the drinks arrived, Mr. Morgan took another large gulp. He must have downed four or five drinks in Dan's presence, and that didn't count the two or three he probably had before Dan even arrived.

"I have to go the bathroom," he announced, standing up.

Mrs. Morgan merely rolled her eyes. "Thanks for the update, honey," she said, teasing him. "Where else would you disappear to?"

"I'll join you, Dad," Steve said, following his father to the bathroom.

When they were gone, Dan cleared his throat. "So," he began confidently. "How've you been, Mrs. Morgan?" His eyes bore into hers as the older woman brought her wineglass to her shiny full lips. He could see wariness, uncertainty, there.

Swallowing the thick, red liquid, she responded, "Lovely, Dan. I've been lovely." She paused, twirling the stem of the glass in her manicured fingers. She ignored him, her eyes focused on her fidgeting hands.

"Tell me, Mrs. Morgan, did you end up getting your asshole stretched that night?"

Dan's brazen tongue caused her to jump. She looked behind her to see if the couple sitting nearby had heard him; thankfully, they had left sometime during the Morgans' meal, leaving them alone in the room. When her gaze returned to the impetuous young man seated to her left, they were on fire. "Watch your mouth, Dan. Don't think for a minute that what happened gives you the right to disrespect me like that."

As she took another drink from her glass, Dan looked at her quizzically. "Disrespect you? I don't disrespect you, Mrs. Morgan," he said genuinely. He leaned forward, his right hand reaching beneath the table for her left, which rested in her lap. "Not at all. I respected you when you let me suck on your big fake tits."

Dan's hand found hers beneath the table. When their skin touched, Mrs. Morgan pulled back, the diamond of her engagement ring scraping along his palm.

"I respected you," Dan continued, "when you were sitting in my lap with a wine bottle shoved in your cunt."

"Fuck you, young man," she spat, the malevolence obvious in her eyes.

"Yes, I respected you then, too." He glanced toward the main part of the restaurant. Mr. Morgan and Steve had finished in the bathroom and sat at the bar, the father smoking a cigarette. Dan again reached for Mrs. Morgan's hand under the table, gripping it tightly, feeling the four-carat diamond press against his palm, her long nails bite into his skin. She resisted, but it was a weak effort.

"I respected you when you had my cock trapped between those things," he continued with a nod at the married woman's chest. "But you know when I really respected you, Mrs. Morgan?"

She turned her head from him, breaking eye contact, and didn't respond. She took another nervous sip of her wine, her eyes floating toward the ceiling as though she were praying that Dan would go away.

"Well, let me tell you. I respected you the most when you were bouncing around on my lap with my fingers in your hole while I was talking to your son on the phone."

"You are SUCH an asshole," she hissed through gritted teeth.

"You didn't think I was an asshole the last time I saw you."

Her sparkling blue eyes were softer now, but by no means loving. "That shouldn't have happened, Dan, and you being here like this is awkward. And then for you to sit here and say the things you just said?" She paused and shook her head, again looking to the ceiling. Her voice was barely audible: "Fucking asshole."

"You enjoyed it, though, didn't you Mrs. Morgan? Fucking me? Fucking someone so much younger than you? Your son's best friend, no less?"

Mrs. Morgan again looked at Dan, and then cast a glance toward the bar. Her husband was smoking another cigarette, her son beside him, as they sipped their cocktails, laughing at something the bartender had said.

"I'm going to fuck you again, Mrs. Morgan. You can be sure of that."

"Stop, Dan."

Dan paused, considering. "Tell you what. Steve and I are going to Meier's for a few drinks after dinner. I'll drop him off, and then come back later."

Mrs. Morgan shook her head, her ponytail swinging back and forth, but remained silent.

"Mrs. Morgan, I am going to fuck you in your own house, with your husband and son sleeping upstairs." As the wicked words spilled from his lips, Mrs. Morgan's eyes shifted back and forth between her family at the bar and this insolent young man whose hand was lightly rubbing her inner thigh.

Before she could respond, Mr. Morgan and Steve got up from the bar. Dan quickly withdrew his fingers from between Mrs. Morgan's thighs, instantly missing their warmth, their silky smoothness. She tried valiantly to hide her anxiety as they rejoined Dan and her at the table.

"Whaddya say, honey? Should we get the bill and head home?"

Mrs. Morgan simply nodded and her husband signaled the waiter for the check. "Come on. I'll take care of the bill, and meet you guys outside."

While Mr. Morgan waited for the check, Mrs. Morgan, Steve and Dan walked from Hackney's and across the parking lot toward their cars. As they approached, she dug in her purse for the keys to the Range Rover. "Damn," she muttered.

"What's wrong, Mom?" Steve asked, stopping beside the SUV. Dan continued to his car, parked on the other side of the Range Rover.

"I think I left my keys inside. Would you be a sweetie and go see if they're there?"

"Sure, Mom," Steve responded, trotting back to the restaurant, leaving his degenerate mother with his equally depraved best friend.

Mrs. Morgan slowly came around the front of the Range Rover, putting it between the restaurant and Dan's car. He stood at his open door, one foot resting on the door sill. Her heels clacking on the tarmac of the parking lot, Mrs. Morgan strode to where Dan was standing and stopped, her augmented tits just inches from the top of his muscular stomach.

She looked over her shoulder through the tinted windows of the Range Rover to make sure no one could see them. When she turned back to Dan, she placed one manicured hand behind his head and pulled him down to her, their lips meeting and mashing, her tongue darting between his lips and into his mouth. She cupped her free hand and rubbed Dan's growing cock through his pants.

She pulled back after a few seconds, releasing his cock, and put a manicured finger to his lips, wiping the remnants of her lip gloss from him. "Get him drunk. Have him back by midnight," she whispered. "You come back at one. I will fuck you like none of your little girlfriends ever has."

She again looked over her shoulder to see her husband and son coming across the parking lot. She moved away from Dan, the long, shiny nails of one hand tracing down his heaving chest, giving a slight tug at his belt buckle, and called out, "I found them, Steve."

"Good, 'cause I didn't," Dan heard, trying to catch his breath as he sat in his driver's seat. The Range Rover beeped twice as Mrs. Morgan hit the remote and climbed into the passenger seat, her skirt rising to expose more of her long, lean legs. She shot Dan a lust-filled glance as Steve came around the back of the cars and got in beside Dan.

* * *

Dan pulled into the Morgans' driveway at almost exactly midnight. Fifty yards in, it forked, the right fork leading to a courtyard in front of the Morgans' mansion, the left leading off to the side towards a detached coach house that the Morgans had converted into a four-car garage. Dan took the right fork to deposit Steve in front of the massive oak doors fronting the manor.

Getting Steve out of the bar had been no easy task. "Come on, just one more, then we'll go," he had complained.

Dan was having none of it. "Let's go, shithead. You'll thank me in the morning." He finally convinced Steve that his mother would be rather upset if he appeared at his sister's engagement party with a raging hangover.

Steve got out of the car with a promise to call the next week. Dan turned his car around in the courtyard and slowly made his way back toward town to the only open convenience store. He was, of course, stalling, as he had an hour to kill. After buying a Gatorade, he drove around for a while, ultimately ending up back near the Morgans' house.

He couldn't park on the street at this time of night without the police writing him a ticket, so he doused his lights and pulled into the driveway. He slowly rolled up the pea-gravel path and took the left fork, which led him back toward the old coach house-cum-garage. He circled around the side of the manor, following the driveway, and came to a stop underneath an ancient oak tree. Silently, he opened his door and exited the car, shutting the door behind him with only a barely audible click.

Being familiar with the Morgans' property, Dan easily made his way in the dark to a flagstone path that led from the driveway and through the back yard. It wound between the manor, landscaping and a swimming pool, ending in a large veranda littered with tables, chairs and lounges. Dan weaved between those obstacles before coming to a stop before double French doors, one of which was slightly ajar.

He slowly pushed the door open, cringing as he waited for a hinge to squeak. Hearing nothing, he pushed the door open further, stepped through, and found himself standing at one end of the Morgans' gourmet kitchen. Before he could move further into the house, Mrs. Morgan appeared in a doorway at the far end of the kitchen, her luscious body silhouetted against the light streaming in from the television room.

"You're late," she whispered, flicking a dimmer switch, turning the kitchen's overhead lights on low. She was still dressed as she had been at Hackney's, though her blouse was now untucked.

"Sorry. I--," Dan began before she interrupted him.

"Sshh. Not so loud." She crooked a finger at him, beckoning him toward her. As Dan approached, she moved aside, letting him pass into the television room. Her scent – Bulgari? – caught his olfactory attention as he brushed against the lovely woman's warm body.

Dan stopped short upon entering the room. Sprawled on the couch, snoring, was Mr. Morgan. The opening theme to M*A*S*H sounded from the plasma television mounted on the wall opposite the couch. Dan turned back to Mrs. Morgan and mouthed, "What the fuck?"

She waved him back into the kitchen and when they were out of sight of the television room, she turned back to him. Placing both hands, palms open, against his broad chest, Mrs. Morgan leaned into him and whispered in his ear. "Don't worry. He's passed out. He'll be there all night."

Dan's cock stirred as Mrs. Morgan's hot breath caressed his neck and inner ear. Her perfume wafted through his nostrils. He shuddered at the heat that flowed from the palms of her hands and through his shirt. He slipped a hand to her hip and pressed her against the kitchen counter, burying his face in her neck.