Paula's Discovery Pt. 09

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Paula and Joni graduate to cougar night.
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Part 9 of the 9 part series

Updated 06/09/2023
Created 11/28/2018
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Paula and Joni graduate to "Cougar Night." Part 9 in the "Paula's Discovery" series.

Penny set a late brunch time of 11 allowing the girls to sleep in.

When Paula's phone alarm chirped at 10, she noticed a text from Tom.

"HOPE U HAD A GOOD TIME LAST NIGHT AND RAISED LOST OF $$$$." "LOOKING FORWARD TO SEEING U TOMORROW NIGHT."

Paula was still not sure exactly how she felt when she thought of Tom. She knew she still loved him and didn't want that part of her life to change but she was also enjoying the new experiences. She felt lucky that he supported her adventure but hoped there would be no adverse effects.

As Paula finished the light make-up job she heard the knock on the connecting door and opened it to see Sheila in her warm-ups; the now-standard breakfast uniform of The Club. Paula grabbed her jacket, slipped it on over her sports bra and grabbed her key card.

Both ladies were refreshed by a good night's sleep and the late wake-up. As the elevator descended to the ground floor neither spoke but the knowing smiles indicated they were both thinking of the activities of the previous evening. Paula smiled when she thought that if someone told her two months ago that she would have had an experience like that she would discount them as a lunatic.

Surprisingly, Penny and Anne were already seated at a large table with mimosa's and a small plate of fruit and yogurt. They smiled as they greeted Paula and Sheila. Penny waved to the young waitress and pointed to the two ladies and to the mimosa glass in front of her. The girl smiled, nodded and headed to the bar. Paula and Sheila walked to the buffet, made some light choices and when they returned to the table, they found mimosa's at their places. As they took their seats, Marge and Joni joined them and the waitress headed back to the bar.

This girls enjoyed breakfast, surprised at how hungry they were and then realized the empty seat at the table. As if reading each other's minds, Penny offered that Jane and Rob had seemed to get along well the previous evening and the girls smiled and wondered as one.

Almost on cue Jane appeared. Although smiling and animated Paula noticed she did look a bit tired and was moving a little more deliberately than normal. The attentive waitress noticed the new arrival and had a mimosa for Jane almost before she sat down.

Penny took charge and raised her glass. The girls responded in kind and Penny offered a toast.

"To a record-breaking fundraiser and some new shared experiences."

The girls toasted each other around the table.

Turning to Paula and Joni, Penny said, "We have certainly enjoyed your company this weekend and I hope you have enjoyed ours."

Joni nodded with uncharacteristic energy and the girls laughed, hoping that what they had apparently unleashed in Joni would have positive consequences.

Penny continued, "Despite the fun, the weekend's activities were designed to give you confidence in yourselves and to help you enjoy your sensuality." "We all feel that a lady has the right to pursue her pleasure but societal conditioning has not given us the comfort and skills that may require."

"We have one final exercise for you if you are still willing to accept the challenge." Penny said, part statement and part question.

Paula and Joni looked around the table and then nodded enthusiastically at Penny.

"Tonight is cougar night." "Each of you must choose a younger man and,..how should I say..,,ensure that all your needs are met for the rest of the evening," Penny said.

Paula knew there was a rite of passage for the group but when Penny spelled out the evening's activity Paula had a flood of different emotions. Amazingly, her first thought was not of the risk to her marriage. Although Tom could not have known the specifics he had encouraged her to enjoy the weekend and she had to admit the previous days had been very liberating and exciting. Her moment of doubt was instead whether she could fulfill the night's objective to the satisfaction of Penny and the others.

In short, was she up to the challenge?

Joni looked at Paula with a look of bewilderment but as Paula smiled, so did Joni and in that instant they traded energy that would get them through the night.

Penny continued, "We, as always, are focused on your safety and this hotel was not chosen at random." "Some large corporations, use this hotel for their employees who are in town for training or conferences and other organizations use the hotel and its conference rooms for training and seminars."

"This week Bob has a class of new sales personnel, all young and predominantly male and this week there is also a medical seminar and some corporate entities are holding new-hire training." "That should provide ample opportunities and a diverse selection for you," Penny said with a sly smile.

"Sheila and Marge and I will be in the bar to make sure you are safe and I have retained the service of a trusted bodyguard who will be available at a moment's notice." "Please provide an extra key to your rooms so that he can assist if you text or call my phone," Penny explained.

Paula wondered if the service of Penny's friend had ever been needed but felt comfort in knowing that she would be protected and more importantly, that The Club had taken her safety very seriously.

Penny looked at Paula and then at Joni to gauge their response.

To the surprise of the group Joni spoke first.

"Why must we choose younger men and how much younger should they be?" she asked.

There were smiles around the table as the others knew what was coming.

"In reverse order, we expect the men to be at least ten years younger...although we don't require you to check driver's licenses for birth dates," she smiled.

"As to why, there are two main reasons," Penny began. "The natural order is for women to be pursued by older men." "We have discovered it is more empowering and liberating to prove that we are capable of attracting men whom we might naturally think would not be interested in an older women."

"The second reason is that younger men are....," Penny paused for the girls to complete her sentence.

"Young, hung and full of cum!"

Penny smiled and explained further, "Part of the intent of the night is for you to have the experience of being completely satisfied with both the type and quantity of the young man's service." "Since this is a purely physical and erotic encounter we want you to experience complete fulfillment."

To Paula's surprise, Anne spoke up. "Choose wisely girls." "If you have ever seen a man with characteristics you find intriguing and wondered what it would be like to be with him, tonight is your chance to explore."

The girls returned to their plates and soon small talk and teasing about the previous night's activities flowed. Although no one asked specifically, everyone still wondered about Jane's evening but no one, including Marge asked.

After second trips to the buffet and a quick sampling of the dessert table Penny provided more details. The group would meet again at 5 for an early light dinner at a casual restaurant a block away. After dinner they would dress for the evening and be in the bar by 8 when the "meet and greet" events of the hotel guests would be over and the Skybar would begin to fill. Paula and Joni were to enter separately and find seats at the bar without acknowledging that they were acquainted. Sheila and Marge would be nearby and ready to intervene if needed to rescue the ladies from unwanted "hard chargers" who may be in the room.

One surprise detail, their outfits for the evening had been chosen by the girls in the Club and prepared by Anne's assistant. When they returned from dinner she would arrive at their rooms with everything they needed for the evening along with the make-up artist from the night before.

Sheila suggested that they get in a little exercise and Paula had to admit stretching out and occupying her mind for an hour or so would be a welcome break. They excused themselves and walked toward the elevator.

Paula selected a pair of bright blue tights and pulled a pair of loose black shorts on over them. She layered a black tank top over the white sports bra. As she looked at herself in the mirror she heard the knock at the adjoining door and Sheila stepped in. She wore a pair of black leggings with similar loose shorts over her hips. She too had a sports bra with a layered tank top over but the look was different as the sports bra was filled to capacity and lifted and displayed her "girls" to advantage.

Sheila smiled and said, "I have to wear shorts to cover my big ass, but why do you wear them?" she asked with a smirk.

Paula retorted, "I could say the same thing about your tank top and your great tits."

Sheila pondered the comment for a moment and then pulled the tank top over her head, looked at Paula and asked, "Happy now?"

Paula laughed and turned toward the door but Sheila grabbed her arm and said, "If this is how we're going to play this game, then you've got to lose the shorts."

Paula felt herself blush but this weekend had been one first after another so she slid the shorts down, let them fall around her ankles and stepped out of them.

She smiled at Sheila and opened the door.

Paula felt a little uncomfortable knowing that the tights molded to her butt and left nothing to the imagination but she felt confident and excited. She thought about the evening ahead and wondered if she could live up to the challenge.

As Paula and Sheila stepped off the elevator on the 10th floor, they saw that the workout facility had a nice view of the city. Paula liked to have some source of distraction as she used a bike or treadmill. The attendant handed them towels as the girls flashed their room keys and Paula was pleased to see the facility was not crowded at mid-day on Sunday. Paula and Sheila paused and looked around the room just as a young man entered the room. He was about 5'11" and Paula guessed late 20's. Short blonde hair, and although he wore loose workout gear she saw that he had a tight, swimmer's build.

He politely checked in with the young attendant and the girls both noticed the cute pert attendant move quickly to "flirt mode", but he seemed a little shy and intent on his workout mission. He stepped past Sheila with a polite nod and smile and as he turned toward the workout machines Sheila noticed that he stopped as he saw Paula's shapely butt. Sheila smiled and decided she might have some entertainment now that she had categorized him as an "ass man."

"Too bad," Sheila thought to herself, "nice body and I haven't had enough fun yet this weekend."

Paula didn't notice and stepped onto a treadmill along the windows, hung her towel over the handrails and looked at the control panel. It was a type similar to the ones at her gym and she felt right at home. Sheila faked a look at her phone and watched as the young man covertly chose a weight machine behind Paula and began his workout.....both of them enjoying the views. Sheila chose a bike, off to the side of the room where she could watch the only action in the room...so far.

As Paula settled into her routine, she noticed someone on a weight machine, reflected in the glass behind her. It was difficult to see much detail but he appeared to be younger and very fit.

Paula smiled as she mentally repeated their club "motto", "Young, hung and full of cum."

After about fifteen minutes of an easy jog pace, Paula saw Sheila move to the machine next to hers. As Sheila started the machine and began a walking pace, Paula noticed a big grin on Sheila's face.

"Do you know you have an admirer?" Sheila offered.

"What do you mean," Paula responded.

"There were lots of other machines available but he picked the one behind you,' Sheila explained barely containing her glee.

"Is he cute?" Paula asked, playing along.

"Very nice," Sheila said emphatically, "and from what I could see during his workout, very well endowed."

"You know what Penny would say," Sheila reminded with a smirk.

Paula felt her skin flush but found that she enjoyed the thought of her ass getting attention from a young man, maybe tonight would be better than she thought?

As the treadmill program entered the cool down phase, Paula felt invigorated and began to wonder what she would do as she stepped off the machine. Should she pretend that she didn't notice him or should she challenge him?

Paula grabbed the handrails as the machine stopped and reached for the towel. She held the towel to her face and neck and stepped off the side away from Sheila. As if she could sense Paula's dilemma Sheila smiled and nodded her head back toward the young man.

Paula turned and stood for a moment facing toward the young man as she dried off with the towel and decided to acknowledge his presence and see what reaction she got. As she began to walk past him he was finishing a "rep" and sat up, straddling the bench. Paula smiled at him and was surprised that he blushed and seemed shy as he returned her smile, perhaps wondering if she had been aware of his covert admiration. This ruined the mental image she had of a leering young man focused on her butt. Still, he chose this machine instead of several others so she amended her mental profile of him as a discrete, professional-type.

Paula liked that type.

Paula picked up a bottle of water from the chiller and allowed herself to relax and refresh. She was now behind the young man and it was her turn to enjoy the view. Although there were other young men in the workout room, he seemed to be by himself and was concentrating on his routine. Paula watched in fascination as he worked his leg muscles and as his thighs flexed she could see what looked like a very tight, muscled butt inside the loose shorts.

Paula liked that type too.

As Paula sat, deciding whether to do a light workout on the weight machine or simply continue to enjoy the view of what was now several good-looking men in the room as she waited for Sheila to finish, two 30-something men walked past her to the water cooler.

"Did you see the rack on that Milf on the treadmill," one quietly said to his buddy.

"I sure did," his buddy responded. "My mind kept hoping she'd fall out of that sports bra."

Paula was pleased that she now had something to tease Sheila about.

As Paula told Sheila about the conversation she overheard, Sheila said, "Just because you and Joni are the focus of the weekend doesn't mean you're the only ones who can have fun." "It's nice to know I can turn some young heads."

The girls spent the rest of the afternoon napping and relaxing and then began to get ready for dinner. After showers they put on the uniform of the day which was casual slacks and tops and comfortable shoes. Somehow, Paula knew the evening's attire would not include flat shoes. Dinner was the fun easy exchange of friends who were now comfortable with each other. Sheila had too much fun telling about Paula's admirer in the gym and Sheila told of the overheard conversation as a badge of honor. Paula looked at Joni from time to time and sensed some nervousness but since she would be lying to say she didn't have some doubts of her own, she tried not to let the conversation turn in that direction.

After dessert, Penny asked for the extra room keys from Paula and Joni and gave the girls phone and text instructions in case one of their guests got a little out of hand. Penny said there had never been a problem and as long as she was involved there never would be!

Paula and Sheila returned to their rooms and opened the connecting door. As Sheila laid out her ensemble for the evening, Paula felt a little awkward not having any decisions to make for herself but with a sly smile Sheila assured her that everything would be arranged for her.

At 7, there was a knock at the door and Heather, the makeup artist from the previous evening arrived and quickly had Paula sitting at her desk chair with a drape to protect her warm up suit from any make up smears. When Paula saw herself in the mirror she was stunned and pleased. Her look for the evening was much sexier than "business' makeup but not quite as far as the look from "Slut Night." The look would be one of an office professional out for an after work drink but still be extreme enough to give her the feeling of playing a role rather than being herself. Red lipstick but with a little of the smoky-eyed sensuality of the previous evening. As Heather packed up her bag, there was another knock at the door and Sheila opened the door. Anne and her assistant were there with shopping bags and a hanging bag. Paula's pulse quickened as she wondered what they had for her.

The three conspirators were enjoying the drama as Paula stood and they made a great show of laying things on the bed. There was a shoe box and a smaller bag with the logo of the lingerie shop they had visited earlier in the weekend. With flourish, Anne opened the zipper on the bag and withdrew a beautiful, finely tailored, pin-striped suit. Paula instantly felt relieved that she would be wearing something she was comfortable with but then she noticed the sly smiles on the faces of Anne and Sheila. It took Paula a moment to notice but the skirt was a little shorter than she was used to seeing.

No, the skirt was a lot shorter than she was used to seeing.

Paula's heart rate increased.

Anne couldn't resist and said, "Marge suggested this as something you can use again when you need to make a stronger argument for a client with a weak case."

Feeling suddenly very self-conscious, Paula was glad when Anne said, "We'll leave you to get dressed." "We have another delivery to make and we need to be upstairs in less than an hour."

They gathered up the other bags they left by Paula's door and headed down the hall. Sheila smiled and said, "I'll be next door getting ready."

Now alone, Paula, opened the lingerie bag and saw beautiful black silk and nylon. There was a lacy bra, her exact size of course, two sheer black stockings a garter belt. Looking for panties, she saw only tiny triangles of lace with silk behind and with the thinnest of black straps. Tom enjoyed seeing Paula in sexy lingerie and regularly bought her presents from a local shop but even he had never picked anything this revealing. Paula laughed at herself as she was suddenly glad she had chosen the "almost nothing" trim at the spa.

Quickly stripping off the warm-up suit, Paula stepped into what would serve as panties for the evening then slipped on the bra and fastened the small hooks in the back. It of course fit perfectly since Anne knew their sizes. She wrapped the belt around her waist and sat to slide the expensive stockings up her long legs. She stood to adjust the straps of the garters and felt the sexy feeling that always overtook her when she put on erotic lingerie.

Paula picked up the suit and removed a gray silk blouse that was on the hangar inside the suit blazer. It felt exquisite as she pulled it on over her shoulders. She felt it move over her breasts as they were pushed up with the tiny bra and she felt warmth throughout her body and felt her nipples respond.

Paula hesitantly picked up the tiny skirt, unzipped it and stepped into it. When she was how far up her legs it was hemmed, she suddenly had doubts as to whether she could go out in public in it. As she zipped it closed and fastened the single button at the side she walked to the mirror. Paula realized she would need to pull the garters up a bit shorter but even then almost any movement would expose the tops of the stockings.

It occurred to her that in the next few hours she would be removing everything she just put on and she felt an uneasy thrill when she reminded herself she had no idea who would be with her when she did.