The Cougar Chronicles 04 - Jenny

Jennifer Mann - "Jenny" for short - was one very busy woman. As the first female head of a major stock trading company, she had her work cut out for her in more ways than one. The job itself was stressful enough, but when combined with the never-ending fight to prove to the "good old boys" on Wall Street that she was just as good - if not better - at her job than any of them could ever hope to be, at times it became almost too much to bear. She had been fighting this fight for her entire professional life, all twenty-five years of it, and it seemed that the older she got the harder it was to take sometimes. Turning 50 this year hadn't helped any, either; it only made things worse at times. And whenever it got that bad, Jenny made it a point to get away from work for a while, as far away from it as she could, to just relax and unwind.

And it had gotten that bad earlier this week. The stock market had tanked with more bad news from Washington, D.C about the federal deficit and the ongoing failure of Congress to pass a budget yet again, so she had investors screaming at her in dismay from all points on the compass. After soothing all of the fears of her clients, which took the better part of the week, when Friday morning came around she figured it was time to take care of herself. She could feel it building up inside her and knew that it was time to get away, so she picked up her phone and pressed the button to ring her secretary.

"Yes, Miss Mann?" her secretary said.

"Debbie, would you be a dear, please, and call "The Windjammer" and make a reservation for me? I'll be arriving tomorrow afternoon by car and will be staying for a week," Jenny said. "The Windjammer" was her favorite beach resort hotel, and it was her favorite "getaway" spot whenever she felt the need to get away - like now.

"Yes, ma'am," Debbie said.

"Thank you, Debbie!" Jenny said, then hung up. Fifteen minutes later Debbie called back to confirm that the reservation was made.

"There was a little bit of trouble with the short-notice at first, but as soon as I told them who the reservation was for they were only too glad to take care of it!" Debbie said, and Jenny could tell by her tone of voice that she was smiling. "You have your usual room, the Admiral's Suite on the top floor, seaside. And the manager said that there will be a bottle of Dom Perignon in a chiller waiting for you in the room when you arrive."

"Thank you, Debbie, you're the best!" Jenny said, chuckling to herself just a bit. 'Sometimes it's good to be the queen!' she thought to herself.

"You're welcome, Miss Mann, enjoy your vacation!" Debbie said, then hung up.

After hanging up the phone Jenny got up from behind her desk, taking her purse out of the bottom drawer of her desk and then walking over to the coat rack and picking up her suit coat. She put the purse down on the floor as she slipped the coat on, then picked it up again and headed for her private entrance.

"If I'm going to spend the next week at the beach, then I need some new bathing suits!" she said out loud to herself as she opened the door and walked out of the office.

At a little after four o'clock in the afternoon the next day Jenny pulled her red Camaro convertible into the drive of the hotel and parked in front of the entrance doors. She always enjoyed road trips, and knowing that her destination this time was her favorite beach resort hotel had made the long trip all that much more enjoyable. She got out of the car and walked through the doors into the lobby, the ocean breeze blowing her blonde hair around her face for a moment. She checked in at the front desk, then gave her car keys to the valet so he could park her car and then bring her bags up to her room.

She had never seen this valet before, but then that wasn't too unusual considering how often staff changed at these hotels. Still, this one was something else to see - tall, lean, with what appeared to be a pretty good build beneath his white shirt and black vest, a shock of dark brown hair that was so dark it was almost black, and a chiseled face. When he smiled at her she noticed near-perfect teeth, and when he walked towards her car she noticed quite a tight little butt beneath his black dress slacks.

'My, isn't he something!' she thought to herself. 'He can drive my car any day of the week and twice on Sunday!'

Then she headed for the elevator and went up to her room to freshen up a bit and relax for a while before going out to get something to eat. She opened the door to her room and the first thing she saw sitting on the dresser was a chiller with a bottle of Dom sitting it it, just as promised. She smiled and tapped the cork of the bottle as she went past on her way out to the balcony, and once there she opened the balcony doors and stepped out to enjoy the view. The weather was perfect, as usual, and the view was stunning, also as usual. She lifted her face up to the ocean breeze and closed her eyes, smiling at the sensation of the breeze on her face, the sound of the ocean, and the smell of the beach.

'This is my favorite place in the whole world!' she thought to herself, and her smile widened.

The knock on her door snapped her back to reality, and with a sigh she turned and walked back through the room and opened the door. The valet was there with her bags, so she let him in to bring them inside. She noticed the name "Paul" on his name tag as he walked past to set the bags down on the floor at the foot of the bed, then turned to face her before leaving.

"Will there be anything else, Miss Mann?" Paul asked, smiling at her.

"Thank you, Paul, no," she said, walking over to him and handing him his tip, returning his smile. As she looked at him close-up she saw he had the prettiest gray eyes she'd ever seen, so clear and deep that she felt she could easily get lost in them. "And please, call me 'Jenny,' " she added, making his smile broaden just a bit.

"Enjoy your stay, Jenny, and please don't hesitate to call me if there's anything you need," he said, quickly tucking the bill into his pants pocket without looking at it.

"Thanks again, Paul, I most certainly will!" Jenny said, and was then treated to another view of his butt as he walked out of the room.

'He's a real pro,' she thought to herself as she headed for the bathroom to wash her face. 'He never looked at the size of the bill I gave him, yet he still said what he did and sounded like he meant it. Yes, this one is a real pro!'

"And that could be a problem," she said out loud as she turned on the water.

After washing her face and changing her shirt, Jenny left the room and went down to the lobby to retrieve her car. To her dismay Paul was gone; looking at her watch she saw that it was just after five PM, so she figured that Paul was off for the day. A little disappointed, she smiled at the valet who held the door to her Camaro open for her - a skinny kid with red hair who couldn't hold a candle to Paul - and then got in, putting the car in gear as the door closed and then driving away. She drove to "The Gull Reef Club," her favorite place to eat while at the beach. They had the best shrimp in the whole world there, and that's exactly what she had.

The meal was excellent as usual, but all through the meal Jenny found her thoughts drifting back to Paul, the valet from the hotel. She didn't know what it was, but there was something about him that touched her, spoke to her, made her...well, tingle in all the right places. And that didn't happen too often - even less since she became successful - so when it did happen she paid attention to it.

"I guess I'm just going to have to seduce him!" she said softly to herself, smiling over her glass as she took a sip of her wine. The prospect brightened up her entire evening, and she slept soundly that night.

She awoke fairly early the next day, Sunday, and was intent on doing nothing except laying out on the beach and getting a tan. That was one of her favorite ways to relax, and as soon as she had showered she opened up her suitcase and got out one of the new bathing suits she had bought on Friday. It was a bikini, of course, and was a little risque for someone her age - at least, that's what most people would have thought. But then, she never really gave a damn about what most people thought to begin with. She had bought three suits on Friday, and this one was white. She cut the tags off of it and then dropped it on the bed before walking over to the full-length mirror on the bathroom door. She stopped in front of the mirror and looked at her nude body, placing her hands on her hips and turning from side to side. She was pleased with what she saw.

Jenny made it a point to take care of herself and stay in shape, and it showed. She was a little more than 5'7" tall and weighed in at 140 pounds, which wasn't bad considering she had just turned 50. Her legs were toned and shapely, no signs of varicose veins at all, and led up to a firm, rounded ass that would compare to any 20-year-old's - well, almost any. Her stomach was taut and flat, her waist narrow where it was supposed to be, and the "landing strip" of blonde pubic hair on her pubic mound was closely trimmed above her smooth-shaven outer lips. Moving her eyes up her body to her bust line, she was pleased to see that her breasts still showed very little sign of sag. Considering that she wore a 36D bra and her breasts were very full and heavy, she was surprised that they didn't sag any more than they did. But she wasn't complaining, by any means! She had never been married and had never had children, and she knew that was the main reason her breasts didn't sag and that she was able to stay in the shape she did. A woman's body changed after childbirth, and that was something that she never wanted to go through. She slid her hands up under her big breasts and lifted them in her hands, feeling their weight as she hefted them. Her breasts were capped with silver-dollar sized areolas and pert nipples that were slightly smaller than a pencil eraser, but grew to nearly twice their size when she was aroused. She squeezed her breasts in her hands and then pulled on both nipples, watching the areolas crinkle and the nipples grow quickly at her touch. She couldn't help but imagine how this would feel when it was Paul's fingers pulling on them, and the thought only made her nipples grow harder.

She walked back over to where she had dropped the bikini and put it on, returning to the mirror to see how she looked. She smiled when she saw her reflection, very pleased with what she saw. She was certain she could give any 20-year-old girl a run for her money, any day of the week.

"Not bad for an old broad!" she said out loud, laughing. "I just hope Paul thinks so, too!" Then she picked up her beach towel, wrapped it around her hips like a sarong, picked up her beach bag with her suntan lotion, radio, and assorted other "beach" items, and headed for the beach.

Jenny spent the entire day at the beach, relaxing on the sand and working on her tan, taking an occasional break to swim in the ocean and cool off. The only other time she left the beach was to hit one of the ocean-front restaurants for lunch, and when she finally had her fill of sun and sand - for today, anyway - it was close to four o'clock in the afternoon. As the shadows of the hotels on the beach front behind her got longer and began to creep up and encroach on the sunny part of the beach, Jenny packed up her stuff and shook the sand out of her towel before wrapping it around her hips once again. Then she picked up her bag and headed for the hotel, looking forward to taking a shower and then going out for some more seafood. It only took her a few moments to reach her hotel, and when she opened the door and stepped into the chilly air inside the hotel, she felt her body tremble and her nipples harden. When she walked around the corner to the main lobby to get on the elevator, she felt her nipples get even harder.

There was Paul, standing at the door to the hotel, holding it open and handing a set of keys to a stately woman who was walking out. Paul followed her to the Lincoln waiting in the driveway, opening the door for her as she entered and closing it when she got in. Jenny saw the woman give him a tip, which Paul once again pocketed without even glancing at it. Then he turned to walk back into the hotel, spotting Jenny who had come to a standstill in the center of the lobby. As soon as he saw her he flashed her a big smile with his near-perfect teeth, and Jenny felt a twinge that started at her nipples and ran through her whole body, stopping at her clit.

"Good afternoon, Jenny," Paul said, walking over to her, still flashing that smile of his. Jenny smiled back and tried not to act like a schoolgirl with a crush on the teacher.

"Good afternoon, Paul," she replied, returning his smile. If he noticed her attire, specifically her hard nipples that were about to tear through the fabric of her bikini top, he was doing a very good job of hiding it.

"How was your day on the beach?" he asked, sounding genuinely interested and not just making small talk.

"Wonderful!" Jenny replied. "The beach is my favorite place in the whole world, and when I retire I may just move down here!"

"So now it's a shower and then dinner, right?" he asked, standing in front of her with his hands behind his back, always the professional.

"Yes, it is," Jenny replied. She had a quick flash in her head of the two of them in the shower, and she felt her pussy begin to moisten at the thought. "I love seafood, and I have a mad craving for it today!"

"If I may, I'd like to recommend a restaurant for you," he replied. "It's on the outskirts of town, just on the edge of the tourist section, and it's called 'The Gull Reef Club..." Jenny broke in before he had a chance to go any further.

"Yes, I know it well! It's my favorite restaurant, and I always eat there whenever I'm at the beach!" she said, smiling up at him. 'Nice to know we have something in common!' she thought to herself.

"They have the best shrimp!" Paul said, and Jenny nodded in agreement.

"Yes, they do, absolutely fabulous!"

"Well, then, don't let me hold you up any more," he said, stepping back a pace. "Please, enjoy your dinner and tell me all about it when I see you next!" he said, and Jenny was sure he meant it.

"Why, how sweet! Thank you, Paul, I most certainly will!" she said, then turned to walk towards the elevator. She didn't know if he stood there and watched her ass wiggle as she walked away, but she doubted it as that would have been unprofessional - and from what she'd seen so far, he was anything but unprofessional. When she got to the elevator and pushed the 'up' button, she turned around and looked back at the lobby. Paul was gone, and when the doors opened she stepped inside, a little disappointed, and pushed the button for her floor. The doors closed and as the elevator started up, she let out a sigh and spoke out loud to her reflection in the highly-polished chrome doors.

"I am going to have you, Paul, one way or the other!"

The meal at The Gull Reef Club was fabulous as usual, making up for Jenny not seeing Paul again when she came downstairs to get her car. It was after five by then and Paul's shift had ended, so he had left. She had chosen her outfit in hopes of running into him again, selecting a pair of white shorts that fit her like a second skin and a lime green halter top that showed a generous amount of cleavage. Since she didn't want any panty lines she was wearing a white thong under the shorts, and completed her outfit with a pair of sandals and a small purse on a thin strap.

But he wasn't there, and Jenny felt like it had all gone to waste. He was all Jenny could think about during the meal; she was determined to get him into bed, but she was at a loss on how to do it. She was going to have to break through that professional armor he was cloaked in, and she had no idea how. She had hoped to see him in the restaurant, hoping against hope that it would happen, but she wasn't surprised when it didn't.

It was full dark by the time she pulled her Camaro into the drive of the hotel, giving the keys to the same skinny kid as the night before. Instead of going up to her room and stewing over Paul, she headed for the boardwalk. She felt like walking on the boardwalk for a bit, maybe wandering down into the now-cool sand of the dark beach, before going up to her room. It was Saturday night and the boardwalk was jumping, the ocean side cafes and clubs doing a brisk business, the boardwalk itself filled with people. She walked down the boardwalk for a short distance, then stopped and turned to lean on the railing and look out over the ocean. The moon was just starting to rise, casting its light on the ocean's surface, the sounds of the breaking waves soothing to her ears. She lost herself in the view and the sounds, relaxing and enjoying it all.

"Beautiful, isn't it?" Paul said from behind her. Her eyes flew open and she grinned in pleasant surprise, catching and composing herself before she turned to face him. He was wearing a red polo shirt that fit him very snugly, showing off his physique, and a pair of khaki slacks that also fit him very well. On his feet were a pair of well-worn leather boat shoes, and she noticed that he wore them without socks. His outfit made her tingle again, and she felt her nipples begin to harden as he smiled at her with those incredibly white teeth.

"Yes, it is," she said, looking up at him to see him smiling at her again. 'And I hope you enjoyed the view of my ass, too, because I wore these shorts just for you!' she thought to herself. "I just love the beach at night! I mean, I love it during the day, too, but the night holds a special kind of attraction for me," she said, trying to explain how she felt and feeling like she wasn't doing a very good job.

"I know just what you mean," Paul replied, slipping his hands into his pockets as he looked over her shoulder at the dark ocean and the rising moon. "It's a special kind of serenity that you feel more than see," he explained, and Jenny felt her pussy begin to moisten as she watched his dark hair blowing in the ocean breeze. "The moon shining down on the surface of the ocean, the breeze coming off of the water, the sound of the waves crashing onto the beach, it's all just so...so..."

"Seductive," Jenny finished for him, looking up at him and meeting his eyes as he looked down at her. She held her breath for a moment as his expression didn't change, hoping that her decision to just go for it had not been a wrong one. She felt a wave of relief wash over her as his gaze softened and the corners of his mouth turned up in a smile as he looked back at her.

"Seductive, yes," he said, looking deep into her eyes and nodding slightly. "Just like you, Jenny," he continued, "seductive."

"I was afraid you wouldn't notice," she said, feeling her nipples harden and her juices begin to flow. She saw his eyes flick down to her breasts for a moment, and she knew that he had seen her nipples harden as well.

"I noticed you from the moment I first saw you," he said, his smile growing a bit. "It's hard not to notice you, Jenny. You have such an air of confidence about you, and you're so beautiful that any man would have to be blind not to notice you," he said, pausing for a moment before continuing. "And he'd have to be crazy not to want you as well."

Jenny felt her heart skip a beat at this, and her eyes widened a bit with surprise and delight. She looked into his eyes as she replied.

"And do you want me, Paul?" she asked softly.

"Yes, Jenny, I do," he replied, nodding slightly, never taking his eyes off of hers. "Very much!"