tagMatureNorth Shore Whore

North Shore Whore

byISawYourMommy©

One Saturday afternoon in September 2004, Dan was lying on his couch watching college football when his phone rang. A friend of his from work was on the other end. "Dan, this is Scott, what's up?"

"Just watching the end of the USC game. What are you doing?"

"I've been in the office all day and need to meet Lauren for dinner at 8 or so. Wanna grab a few drinks with me before."

"Mmm, sure. I'm supposed to meet a few friends later. Mind if I have 'em meet us?"

"Not at all. Why don't you meet me at Gibson's? We're having dinner at Hugo's." Hugo's Frog Bar was right behind Gibson's.

"Sure. Give me half-an-hour or so. I need jump in the shower and then grab a cab. Should be down there by 6:30 or so."

"See you there." Dan got up from the couch, took a shower, and hailed a cab to Gibson's. Gibson's was located in what has become known as the Viagra Triangle. It, and many of the bars and restaurants near it, was frequented by forty-something's looking for love. Or sex, whatever was convenient. Gibson's was particularly renowned for catering to older men looking for younger women, and older women for younger men.

As the cab neared Gibson's, Dan called one of his friends that he was supposed to meet that night, but got his voicemail. "Steve, this is Dan. I'm meeting a friend from work at Gibson's for a few drinks. Meet me there at around 7:30 or so. Oh, and call Jeff and let him know. See you later." Dan folded his phone as the cab pulled up to the curb in front of Gibson's.

Scott already had a high table, drink in hand, when Dan entered. "Long day at the office?" Dan said, taking a seat.

"Not really. I just went in for a few hours."

When a waitress appeared, Dan ordered a Stoli and tonic. "What do you have going on?" he asked Scott when the waitress left.

"Nothing much. I just have a big report due in New York Monday morning, and I wanted to take a last look before I e.mailed it over."

Dan and Scott spent the next half-an-hour or so talking about office gossip, complaining about high-maintenance clients, and people-watching. Even though it was still early, the Gibson's regulars (or at least Dan assumed they were regulars) were all present, staking out their turf. It was comical to watch, really.

Dan was about to respond to something Scott had said when something – someone – caught his eye. At one end of the bar, he saw Donna Morgan. He had known Mrs. Morgan for upwards of ten years. He and her son, Steve, went to high school together and had run with the same crowd. They still did; in fact, Dan had just left a voicemail message for her son. The Morgans lived down the street from Dan's family in Winnetka, and he and Steve had been best friends in junior high and high school. They drifted apart some during college, but still maintained a very close friendship.

Their friendship when they were younger had been such that Steve sometimes accompanied Dan's family to their house in Beaver Creek, and Dan on occasion traveled to Naples, Florida with the Morgan family. Dan had always found Mrs. Morgan extremely beautiful, in the trophy wife sort of way, but she was a complete bitch, cold and aloof. She acted as though everything was a bother to her, like she was way above everyone surrounding her. When he and Steve were growing up, she couldn't be bothered to drive them to the mall or pick them up from football practice. The PTA? Forget it; not in a million years. She'd rather be shopping on Oak Street and downing bottles of wine with her friends at Tavern-on-Rush or Bistro 110.

Part of that was her upbringing; her father had been a top personal injury attorney in Chicago. Rumor had it that her trust, which she received when she turned twenty-five, was in the eight-figures. Another part was her husband. Mrs. Morgan was clearly a trophy wife. Dan didn't really know her age, but with Steve being her son, and based on how good she looked, he guessed she was in her mid-forties. Mr. Morgan, on the other hand, was in his late-fifties, at best. He was in venture capital, and provided very well for the family.

At the end of the day, being born into money and then marrying it all over had given Mrs. Morgan a serious superiority complex. Dan remembers that when they were growing up, she would barely acknowledge Steve's friends when they were around the house. She would breeze in after shopping all day, and march through the house, bags in hand, with barely a hello. Given their financial security, the Morgans had full-time help; in Dan's view, Mrs. Morgan did not treat them very well, but instead ordered them around with a distinct lack of respect and compassion. All in all, Mrs. Morgan was a fucking cunt.

Despite this, she was absolutely stunning; no one could rightly deny that. Looking at her across the bar, Dan estimated her height at five-feet-eight-or-nine inches. She had long, dirty blonde hair that flowed over her shoulders and hung a few inches past. Dan cannot recall ever seeing her hair in anything so pedestrian as a ponytail; rather, it looked like she went to stylist every day, and that night was no exception. As rude as she typically was, Mrs. Morgan usually kept her eyes averted from anything as bothersome as Steve's friends, so Dan could not really recall ever seeing any magic or brightness in them, and only knew that they were a shade of blue. This night was a little different; he could see life there. She was enjoying herself.

The small crowd between Dan and Mrs. Morgan parted, giving him a more complete view of her. 'Wow,' he thought. He had to revise her estimate of her height, because she was in three-inch open-toed heels crafted in black patent leather; her toenails gleamed with red polish. As his eyes traveled up her lean, lightly muscled legs – one straight and the other cocked at the knee – he noticed no telltale signs of stockings or pantyhose.

A tasteful black skirt hung from her trim waist, falling two or three inches above her knees. A white knit top clung to her upper body. It was sleeveless, and had a button in front to keep the two sides together. Dan had never seen a top like this, and didn't know what to call it. Whatever it was, it exposed a large part of her flat, tanned stomach. The button – there was only one – joined the lapels at her breast line. It must have been a strong button; Dan had never noticed before, but Mrs. Morgan's breasts were quite large, a large C-cup or a small D-cup, at least. He could see her nipples tenting the fabric. A large diamond pendant hung from her neck and fell between her cleavage. When she turned away from him for a moment to order another drink, Dan was treated to a tight little ass hiding beneath that skirt.

When her drink arrived, Mrs. Morgan brought the low-ball, now filled with a brownish liquid, to her red-painted lips just as Dan turned back to Steve. He saw her French-manicured nails gripping the glass, and her wedding rings sparkled in the faint light of the bar. "Yeah," he said, answering Steve. "I worked on that account for a few months about two years ago, before I got pulled back to Chicago. Not fun. The client wants miracles, and thinks it can happen overnight."

As their conversation continued, Dan's eyes strayed back to Mrs. Morgan. He was alarmed to see her staring at him, her drink paused right before her lips. Dan thought he could see the color drain from her deeply tanned cheeks. After a moment, she appeared to regain her composure, and put her drink to her lips, placing it back on the bar after taking a strong pull.. She leaned over to the person she was talking to, placing a hand on his arm, and walked away from the bar towards the main entrance. As she did so, she beckoned for Dan to follow, crooking a manicured finger at him.

"Gimme a minute, Steve, I've gotta say hi to someone." Dan met her at the main entrance. "Mrs. Morgan, so good to see you," he said with mock sincerity, holding out his hand. He really did hate her. He would kiss some of his friends' moms on the cheek when seeing them, but not Mrs. Morgan. You'd probably get slapped for messing up her make up.

"You, too, Dan," she responded with the same artificiality, taking the offered hand. Rather than continuing, she just stared at him.

"What can I do for you, Mrs. Morgan? You summoned me over here." Sarcasm dripped from his voice.

"I . . . I didn't want you saying anything . . . to Steve, I mean. Well, er, anyone, for that matter." The usual confidence was missing. Dan knew what was going on: Mrs. Morgan was on the prowl. Needless to say, this surprised him. He couldn't image this bitch being friendly enough so that anyone would want to deal with her. And despite her beautiful face and sexy body, he had never really imagined her having sex. Her holier-than-thou attitude – which is to say 'bitchy attitude' – did not inspire such thoughts.

"What do you mean, 'say anything'? You're here having a drink. What's there to say?" Before she could respond, Dan continued to play with her, looking around the bar area of the restaurant. "Where's Mr. Morgan? I'd like to say hello to him. It's been at least six months since I've seen him."

"He's not here. He's traveling this weekend," she said, too quickly. "I came downtown to do some shopping, and then met some girlfriends for a few drinks before I go home."

"Girlfriends?" Dan inquired, continuing the game and looking around the space where Mrs. Morgan had been standing. "I don't see any 'girlfriends.' Just that guy you were talking to." Dan nodded his head towards a kid about his age – mid-twenties or so – dressed up for a night on the town in black pants and a silk shirt. 'Probably a trader,' Dan thought. 'What a fuckin' shithead.'

"They're not here yet. They're coming soon."

Dan returned his gaze to Mrs. Morgan. "Really? I'm sorry, Mrs. Morgan. I thought you said you 'met' some girlfriends here. 'Met,' of course, implies past tense, something that has already occurred. Not something that is going to occur in the future."

Mrs. Morgan just stared at him. He could almost feel her hatred of him for intruding on her like this. "I meant I came here to meet them." She paused. "They're not here yet. They will be soon. In the future." She was mocking him. What a fucking bitch.

"Well, enjoy your evening, Mrs. Morgan." As he began to walk back towards Steve, he turned. "Hey, when they get here, why don't you introduce me? Maybe they know my mom, too." Dan smirked and walked away. He knew there were no girlfriends; Mrs. Morgan had to be squirming now. "Sorry about that, Steve. A friend's mom I haven't seen in a while."

Dan watched as Mrs. Morgan made her way back to the bar. Unfortunately for her, Trader Boy had found another mark. She grabbed her drink and took a long pull from it. He expected her to leave then, to find a new hunting ground, but she didn't. She resumed her pose against the bar, but faced away from Dan. 'Does she think that if she can't see me, I can't see her? Wouldn't surprise me, she's so self-centered.'

Dan pulled out his cell phone and dialed Steve, again getting his voicemail. "Hey, it's me again. Cancel those last plans. I've gotta run home for a few minutes after this. Why don't we meet at North Side in Bucktown around 9:00 or so? Call me and let me know. Call Jeff, too." The last thing Dan wanted was for Steve to walk in here and see his mom playing the role of cougar. He hung up his phone and he and Scott resumed their conversation. As 8:00 approached, Steve paid the tab and got up to leave. Dan did, too, taking a last glance towards Mrs. Morgan. She saw him in a mirror behind the bar, and turned to look at him, and then again beckoned him with a long, manicured finger.

"Steve, I'm gonna say goodbye to this lady. I'll see you Monday, huh?"

"You bet."

"Say hi to Lauren for me."

This time, Dan joined Mrs. Morgan at the bar. "Care to join me for a drink?" she asked.

"While you wait for your friends, you mean?"

"Yes, while I wait for my friends. That's what I mean." She sure was confrontational, especially for a married woman found in a bar with a twenty-something on her arm.

"Well, I can't stay long. I'm meeting Jeff and Steve in a little bit. You know Steve, your son?" She flagged the bartender and ordered two of what she was drinking, single barrel bourbon.

"Of course. Don't be an ass."

"Sorry. Just wanted to make sure. It's like I've never seen you before, so I guess I'm just making sure I have all the facts straight."

Mrs. Morgan again just stared at him, not responding. After a minute, she placed her hand on Dan's arm. Dan looked down to see her long fingers rubbing his skin, her diamond rings shining in the bar's light. Past her hand, her tanned stomach was exposed to his gaze. Dan felt his cock stir in his pants. "It's getting crowded in here, Dan. Why don't we go somewhere quieter and talk?"

Dan raised an eyebrow. "Quieter, Mrs. Morgan? Or more private?"

Mrs. Morgan paused before answering. "More private," she whispered, squeezing Dan's arm for emphasis.

"What's the plan here, Mrs. Morgan. I catch you on the prowl, and now you'll buy my silence? Is that it?"

"No, that's not it. Not at all. I'm not buying anything, except a drink for you."

"Well, let's think about this. You're at a bar here in the Viagra Triangle without your husband, who is traveling. You're talking to this young guy, laughing and flirting, touching him. You see me and go absolutely pale. You then tell me that you're meeting your girlfriends here, but you want to leave with me and go somewhere private – even though you're meeting your friends here. Sounds like you're trying to buy my silence, Mrs. Morgan. And, by the way, Steve was supposed to meet me here, but I called him a few minutes ago and told him I'd meet he and Jeff somewhere else in a little bit."

Mrs. Morgan's eyes went wide at this, and were then cast downward. She could not imagine the shame if her son had seen her here, hitting on a young man the same age as him. "That would have been embarrassing," she muttered.

"I'm sure. So, do I have it right, Mrs. Morgan," Dan asked, as she continued to stroke his arm with her long nails.

She now dropped the pretense. "In part. The only part you have wrong is my trying to buy your silence. I didn't suggest somewhere quieter – more private – to buy your silence," she said, dropping her voice. She leaned in to his ear. "I want somewhere more private where I can fuck the shit out of you." Her hot breath in his ear and her filthy mouth sent Dan's blood flooding his cock. "I came downtown tonight to find a no-strings fuck with a young cock. You fit the bill. Ready?" she finished, moving away from his ear.

Dan lifted his glass to his mouth, and took a pull of the bourbon into his mouth. He gazed around the bar, thinking, and set his glass down. He then took Mrs. Morgan's hand in his, leading her from Gibson's. "Is my condo private enough? It's only a fifteen minute cab ride."

"Probably. But the Ritz is only a five minute cab ride. I have a suite there." As they exited Gibson's the doorman offered to hail a cab for them, and they stood on the curb waiting. "Dan, do you remember Christina?"

"Steve's old girlfriend?" Mrs. Morgan nodded. "Of course. They dated for a while in high school and during our freshman year at college. She and I went to school together."

"What do you know about her?"

"Enough. Why?"

"Why did she and Steve break up?" Dan had the feeling that Mrs. Morgan knew the answer to these questions, but was asking them for a purpose.

"She cheated on him. You know that. Listen, Christina's a slut. Or she was. Maybe still is, I don't know. I haven't seen her in a few years. Last I heard, she was in South Beach. I'm the reason they broke up. Well, not the reason, but during our freshman year, the first semester we were there, she hooked up with two or three different guys a week. It was ridiculous. She and Steve were still dating. I told her to stop or I'd tell Steve. She said she would, but nothing changed, so I told him. That's when they broke up. She never had a boyfriend in college after that. She just slept with a new guy or two every week. She's got to be the biggest whore Winnetka ever produced."

"I doubt that," Mrs. Morgan replied matter-of-factly.

"You don't know Christina then."

"Well, you don't know me."

Dan didn't know what to make of that, when a cab pulled up for them. He held the driver's side door for Mrs. Morgan and let her in, going around to get in the other side. He slid in as Mrs. Morgan directed the driver to the Ritz-Carlton behind Water Tower Place.

"What's that mean?"

She didn't even pretend to not understand. Her hand floated across the seat to Dan, causing him to shudder as her nails lightly raked his thigh through his pants. "It means that I'm much sluttier than Christina, that's what it means," she said, sidling over to him.

"That's . . . that's ridiculous. I've never heard of anyone messing around with you. I hadn't even thought it was possible."

"Of course you never heard anything like that. I don't fuck my neighbors, Dan. I'm not stupid." Mrs. Morgan continued to stroke Dan's thigh, but her hand strayed further and further towards his crotch with each upward movement. "I drive out to places like Fox Lake and go to Wokini's. Or Hunter's in Highwood. Sometimes, I'll go to the Two Two Lounge or Toby's Tavern in North Chicago."

Dan's eyes opened wide. "North Chicago?" he muttered in complete shock.

"Hmm-mmm."

"A real equal opportunity woman, aren't you?"

"Woman?" she asked rhetorically as her fingers finally found the thickening length of Dan's shaft as it grew down his pants leg. "Mmmm, very nice," she interruputed herself. Whispering in Dan's ear, she continued, "Equal opportunity whore is probably more accurate. White, black, brown, yellow. I don't care, as long as they're a rough fuck, and only if they're young. I love young cock."

"Never would . . . have occurred . . . to me," Dan managed to get out, his breath ragged now from Mrs. Morgan's manipulation of his cock.

Mrs. Morgan could feel the heat of Dan's cock through his pants as the cab pulled under the Ritz's portico. "The last time I was here, two weeks ago in fact, I received very disapproving looks from the doormen and the concierge," she said with a smirk, getting out of the cab.

"Why's that?" Dan said as he followed her out of the cab, adjusting his cock to a more comfortable position.

After they made their way through the revolving doors, Mrs. Morgan leaned into him and whispered, "It seems they didn't like me bringing the twenty-year-old busboy from Hugo's back here." Dan's heart skipped a beat.

Exiting the elevator, Mrs. Morgan strutted across the lobby, imperial as ever, to the concierge's desk and ordered a bottle of wine to be brought up to her suite. She and Dan then boarded an elevator to the twentieth floor. When the doors swooshed shut, and they were alone, Mrs. Morgan leaned into Dan.

"This is going to be fun," she giggled, one of her hands gripping Dan's belt buckle and pulling him towards her, the other wrapping around the back of his head. "I've never fucked one of Steve's friends before." Mrs. Morgan pulled Dan's face towards her own, her shiny red lips parting to allow her hot, pink tongue to escape. Then their lips touched, and Mrs. Morgan's tongue slipped into her son's best friend's mouth, probing. Dan was quick to respond; he let Mrs. Morgan's tongue find his as he placed on hand on her trim hip, pulling her closer to him. Their lips – and bodies – parted as the doors of the elevator opened on the twentieth floor.

They entered the suite and Mrs. Morgan began turning on lights throughout the suite. "Make yourself comfortable, Dan. I'll join you in a second." Dan took a seat on the couch in the living room. A moment later, Mrs. Morgan entered the living room again, strutting toward him with her sexy, trim hips swaying. She joined him on the couch, tucking a leg underneath her, and turned toward him and began to speak. "So, Daniel . . . ." A knock on the door interrupted her. "Be a dear and get that, wouldn't you?"

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