The payment from Leslie's last job hit her bank account as June turned into July. Leslie now had more than enough money to get her through the month. She had also ordered a new item online which she hoped would be delivered in a discreet package: a twelve-inch silicon dildo, which she intended to use to practice deep-throating. She knew she wouldn’t get used to it right away, but she was determined to try to work on her gag reflex when she could.
Leslie’s phone then rang, and she looked at the display. It was Stephanie.
“Hello, this is Leslie,” she answered.
“Leslie, this is Stephanie, Mr. Henderson's assistant.”
“Yep, I remember,” Leslie cheerfully replied.
“Mr. Henderson requests that you meet him this Thursday, July 4th at 8 p.m. This event will likely go late, probably past midnight, so he is also offering you the option of spending the night if you wish. Pre-hour starts at 7 p.m.”
“Oh. Uh, I suppose that depends on how late it will go. Do you have an idea?”
“Unknown but it is likely that it will end quite late. Or early, depending on how you look at it,” Stephanie explained.
“Okay, I’ll think about whether I want to do that. Thanks,” Leslie answered.
“I’ll see you there!” Stephanie cheerfully concluded before hanging up.
Leslie wondered what this event was about. It must be some Independence Day celebration, given it was on July 4th, but what exactly was it going to entail?
However, a complication arose the next day when Leslie’s friend Tiff called her and invited her to watch the fireworks in town the night of the 4th.
“Ah, I’m sorry. I already have other plans that night,” Leslie tried to explain with as little explanation as she could get away with.
“Other plans?” Tiff replied with a little laugh. “With who? Wait. Don’t tell me. Is it a guy?”
“Something like that,” Leslie tentatively answered. She figured that the answer wasn’t exactly incorrect.
Tiff giggled. “Well, you’ll have to tell me about it later. Anyway, we need to get back together again soon with everyone. It’s been a while!”
“Yeah, it has been. We should see if we can find a time for it,” Leslie sighed, relieved that she got past the issue without any lengthy explanation.
“Alright, I’ll see you later then,” Tiff chirped before ending the phone call.
Leslie leaned back into her seat. While she didn’t reveal the real reason she wasn’t available, she now had to come up with something to tell Tiff and perhaps her other friends later. Maybe she had a date but he called it off at the last minute? That would allow her not to have to give any details about a date that never happened, but they might still wonder why she wouldn’t have just called them to hang out with them afterward anyway. She was going to have to figure something out, and she didn’t like that she might have to lie to her friends to satisfy their questions.
Thursday came and Leslie once again arrived an hour before her pre-hour even started to give her enough time to get ready, swapping her clothes for her usual choker and sandals with nothing in-between. Soon after the hour started at seven, Scarlet strode into the makeup room, wearing her usual work uniform.
“Hey, Leslie! Need any help?” she helpfully asked.
“Oh, if you wouldn’t mind,” Leslie answered, flashing a smile back at her. "Do you have any idea what's going on tonight?"
Scarlet shrugged. "I don't know, but I'm supposed to be ready to do a lot of cocktail mixing, so I'm guessing there are going be quite a few guests."
A lot of guests? Leslie pondered as she continued to glam herself up. So far she had only entertained Jacob and one other guest, and their pet. She wondered just how many guests would be there that night, and if any of them would have pets of their own.
Scarlet helped Leslie apply her makeup to her back and other areas that were awkward to reach, before touching up her own.
"I guess I'll be seeing a lot of you tonight," Scarlet grinned as she put away her and Leslie's makeup applicators. "I might even be working outside. There is an outdoor bar and kitchen that Mr. Henderson will sometimes use for larger gatherings."
Leslie hadn't had the time to notice just how expansive the outdoor patio area was. Her one time being there was her trial job, and that had largely been confined to a smaller corner of the patio.
"Well, I guess I'll see. It's about time I go to the entrance to meet our guests," Leslie softly sighed. Entertaining an unknown number of guests was starting to make her nervous again.
She walked down the hallway from the staff room to the entrance, where the doorman was, as usual, standing at the ready. Jacob soon arrived, wearing a beige suit and a smoky-blue tie.
"Lovely as always, Leslie," Jacob greeted, giving her a soft kiss on the cheek. "Tonight is a bit of a special occasion. It's a bit of a tradition for me to invite some friends and business partners for the 4th of July. None of them are pet owners, but they are of course aware that I am. For the first part of the evening, you'll mostly be serving and entertaining our guests, and then we'll see where things go from there."
"Understood, sir," Leslie breathed out. She hadn't been this nervous since her trial job. Both of her jobs to this point had felt quite a bit more relaxed and casual, but this one had an air of seriousness, at least on her part, even if the men she was entertaining might have a more casual connection to each other.
The doorman opened the door and Leslie and Jacob walked outside. It was still rather hot and humid out, and Leslie was rather glad there was a slight breeze blowing to cool herself off. Sometimes being nude had its advantages. Soon enough, the first car arrived.
Stepping out of the car was a taller, slightly plump man wearing a navy polo and white trousers, with greying brown hair, blue eyes, and slightly tanned skin. Leslie felt that he was probably about ten or fifteen years older than Jacob—maybe in his late fifties.
"Jacob, how have you been!" the man stepped up and forcefully shook Jacob's hand.
Jacob returned the greeting with gusto. "Charles, it's always a pleasure."
"Well, I always have to check out the home I sold you, don't I?" Charles boomed with laughter. "I take it you are still enjoying it."
"Thoroughly," Jacob confirmed.
Charles' attention then turned toward Leslie. "And who do we have here? I wasn't aware that you had hired someone new to replace Emily." He stuck out his hand for Leslie to shake. She shook it, the man giving her a beaming smile as she did. He could see his eyes look her up and down, but they didn't linger. Perhaps just an assessment of Jacob's new employee.
"Charles, this is Leslie. And yes, she has taken up Emily's previous position as you already guessed. She just started, what? Maybe a month ago?" Jacob remarked, looking at Leslie for confirmation.
"Uh, two weeks, sir," Leslie kindly corrected him.
"Two weeks? It already feels longer than that. I guess it just shows what an impression you've already made," Jacob added, grinning over at her. "Anyway, Leslie, this is Charles Andrews. As you might have guessed from his previous comment, he is a real estate developer. He is the one who sold me this house many years ago."
"Ah, nice to meet you, Mr. Andrews," Leslie nodded.
Jacob and Charles continued to converse when the next pair of cars arrived. A man of Indian descent exited the first, aged somewhere between Jacob and Charles. He was dressed in a lightweight blazer over a light blue shirt and a matching pair of slacks. He was closer to Jacob's height, with salt and pepper, closely cropped hair, and striking brown eyes, over which he wore a pair of thin-rimmed glasses.
Out of the second car stepped another man, a couple of inches taller than the first, wearing tailored chinos and a lavender dress shirt. He appeared to be approximately the same age as Jacob, with blonde hair, green eyes, an athletic build, and a neatly trimmed beard. Leslie thought that he may qualify as "sexy."
The two men greeted each other before walking toward the entrance to greet Jacob and Charles. As before, there was a round of introductions, Jacob having to introduce Leslie to the men as each of them had been accustomed to her predecessor, with Leslie learning that the two newest guests were named Raj Patel and Johnathan Chambers.
The guests continued to chat amongst themselves as Jacob and Leslie continued to greet additional guests.
There was Gregory Easton, another taller man with broad shoulders, steel-grey eyes, and grey hair who appeared to be more of a friend than a business associate of Jacob's.
Then there was David Lerner, the youngest guest of the group, in his late thirties or early forties. He had a lean frame with curly brown hair, brown eyes, olive skin, and almost a playful demeanor.
Next was Thomas Blake. He was the shortest man in the group but made up for it with his imposing presence otherwise. He had slicked-back brown hair and hazel eyes which Leslie found to be piercing almost to the point of being disconcerting.
Leslie started to wonder just how many people she would be entertaining when the next guest arrived: Victor Moretti. Leslie could immediately tell he was a bit of a character, with a stylish and florid suit and animated hand gestures, gleefully greeting her with kisses on both cheeks. He was rather stocky—Leslie almost wondered if he had a past as a football player or something similar—with grey hair and brown eyes.
Following Victor was the only woman in the group. Eleanor Price had flowing auburn hair and green eyes and wore an elegant emerald-colored sleeveless jumpsuit. She seemed to have a charm Leslie wished she could replicate.
The final guest was Henry Caldwell. He appeared to be the quietest and most calculating member of the group. He wore perhaps the most straightforward outfit: a simple white dress shirt and blue slacks. He had light brown hair that was beginning to grey and brown eyes.
Leslie's heart was beating. She was feeling a bit overwhelmed. She was glad she wasn't the center of attention—at least not yet—but her mind was racing over how she would interact with all of these guests.
Once it appeared that everyone had introduced themselves to each other, Jacob spoke up.
"It appears it is time we go back and make ourselves comfortable," he announced. The other guests made sounds of agreement. Jacob then led the assembled group through the house and back out toward the patio. Leslie followed along in a position that she felt the most comfortable. She couldn't follow in her customary position directly behind Jacob as guests were currently walking there.
Leslie walked onto the patio and immediately started to assess just how big it was. There was the small area she had sat before, with a smaller set of chairs and a table. Jacob led his guests to another area of the patio which included a rather large sofa that made an "L" around a fire pit. There were also a few other areas to sit and relax as well, including another couch that was in front of a large television. Finally, Leslie spotted the outdoor kitchen and bar, where she spotted the chef, Mr. Cheng, and Scarlet.
Leslie stood at attention while everyone got settled. Jacob, the last standing, walked over to Leslie, putting his hand on her shoulder.
"As you've already seen, I have a new young woman to help me entertain you all tonight. I know Emily was a beloved member of this household for several years, but she has decided to move on to greener pastures. Leslie here will be taking whatever orders you have, so feel free to let her know if you need anything. I am confident that she will do as good a job and be as good of company as Emily has been."
The assembled group applauded Jacob's kind words, causing Leslie to slightly blush.
"With that, can I get everyone's drink orders to start the night?" she inquired, stepping forward.
"I'll have a classic Manhattan," Jacob ordered as he took a seat in the middle of the couch.
Leslie then went around the sofa and got everyone's orders, trying to remember them all. It didn't help that one person ordered whatever beer they had that was cold while someone else said to surprise them.
Leslie walked over to the bar where Scarlet was smiling and relayed everyone's orders.
"A bunch of classics, huh?" Scarlet laughed as she started preparing the drinks. "Maybe I can at least do something adventurous for the one who asked to surprise them."
Leslie let out a nervous sigh and looked over her shoulder at the group. No one seemed to be lingering their gaze her way, and she was rather happy about it. She appeared to be more like a decoration than someone to leer over. On the one hand, Leslie was uncertain how to feel about the fact that they perhaps saw her that way. On the other hand, she was rather happy about it. She'd rather have them treat her like that rather than a piece of meat, which was the likely alternative.
"You're doing great! Don't worry," Scarlet smiled as she started assembling the drinks on a tray, seemingly sensing Leslie's nervousness over the situation.
"Yeah, hopefully. I guess I knew that a job like this would happen eventually. I just ... wasn't exactly mentally prepared for it yet, though," Leslie admitted.
"Just be yourself and you'll be fine," Scarlet reassured her as she put the final cocktail on the tray.
Leslie picked up the tray, heavy with drinks, and she was immediately reminded of her old waitressing days. Of course, she wasn't nude when she worked that old job.
She handed the drinks out to everyone. Before she could put the tray away, Victor raised the sangria he had ordered and raised it. "To our lovely hostess for the evening!" he toasted, eliciting a round of agreement from everyone else. Once again, Leslie couldn't help but blush as she returned the tray to the bar.
When Leslie returned, Jacob beckoned her to sit between himself and Johnathan, the man she had immediately thought was rather sexy when he arrived. She felt her heart flutter for a moment but promptly took a seat between them, trying to remain in a "proper" position with her legs together and back straight, acutely aware she was a naked woman sitting between two well-dressed and powerful men.
"Leslie, this is Johnathan Chambers. He's an investment banker up from New York who has graciously agreed to join us for the evening." Jacob introduced the guest a bit more thoroughly than he had earlier when guests were arriving fast and furiously.
"Nice to meet you, Mr. Chambers," Leslie smiled at him and nodded.
"Please, it's Johnathan," the man replied, putting his hand up as if to signal "stop" with the formalities. "And it is pleasant to meet such a lovely young lady as yourself, Leslie. I'm honored that you could grace us with your presence tonight," he grinned, his response oozing with charm.
"I'm—I'm happy to be of service," Leslie fumbled out, feeling a bit flustered by his compliments.
Johnathan gave a knowing look as if he sensed Leslie's trepidation. "So, Leslie, how have you liked this job so far? You said you've been at it for, what? Two weeks you said?"
Leslie let out a nervous sigh. "Uh, yeah. It's been ... quite the experience so far."
Jonathan had a grin on his face, his green eyes sparkled with curiosity. "Quite the experience, you say? That could mean a lot of things," he teased.
Leslie let out a small laugh. "Well, it’s not your average nine-to-five, that's for certain," she replied, her tone playful but guarded.
Johnathan let out a slight chuckle. "I would imagine not."
Jacob chuckled on her other side, crossing one leg over the other. "Leslie’s been adjusting admirably," he said with a hint of pride. "She’s quick on her feet and has a knack for making everyone feel at ease—qualities that are invaluable at gatherings like this."
Leslie glanced over at Jacob, a faint blush creeping back. "Thank you, sir," she murmured softly.
"Getting such an endorsement from Jacob here is quite the accomplishment, especially for someone so new to the job," Johnathan smirked, "though I imagine it takes more than just poise to manage a group like us," he added, gesturing subtly toward the other guests, who were chatting and laughing among themselves.
She nodded at him in agreement, starting to feel slightly more at ease as the conversation continued. "It helps that everyone here treats me as, well, normal." It was her first formal acknowledgment of her unique situation.
Jonathan raised his glass slightly in acknowledgment. "Glad to hear we’re not making things too difficult for you. Though I suspect you could handle just about anything."
Leslie felt flush and another flutter. Johnathan's charm was overflowing, and it was hard not to feel a connection, especially given that she also found him quite attractive. She almost blurted out "Like you?" in response but quickly thought better of it.
"Leslie has already exceeded my expectations given her time in this position," Jacob added, causing Leslie to blush even harder.
"You're too kind, sir," she answered, glancing back towards Jacob.
"I'm only telling it as it is," Jacob smiled back at her. He then looked at Johnathan. "So what is the latest project you've been working on in New York?"
Johnathan's eyes lit up even more than they already were. "I've been working on an initiative to revitalize an old industrial area into a mixed-use development. Housing, offices, green spaces—it’s been an interesting challenge."
"Oh, that sounds interesting," Leslie admitted. She wasn't entirely sure what all of that work entailed, but she did find it legitimately interesting. "That sounds like a lot of work."
Johnathan let out a chuckle. "Trust me, it is. Nothing is harder than getting old businessmen and city officials to cut through red tape to change an area that has been a blight for a hundred years and turn it into something new and exciting."
"You seem like someone who can handle anyone you need to," Leslie grinned, getting more engrossed in the conversation.
"Oh, what makes you say that?" Johnathan smirked at her, noticing that she had perhaps unintentionally started to flirt.
Leslie once again found herself flustered. "Oh, uh, I just mean that you seem like someone who can convince just about anyone to your side," she tried to explain. She wasn't exactly sure how he would take what she just said.
Johnathan chuckled. "I see. And you, how do you keep so composed in a gathering full of people like this? Being new to this, I can't imagine how nerve-wracking it must be to cater to a bunch of fancy business types."
The question caught her off guard, and she paused for a moment before answering. "I think it’s about focusing on the moment," she remarked. "That kind of helps with the nerves a bit."
Jonathan raised his glass again, this time in a smaller, more personal toast. "To staying composed under pressure," he said, his gaze holding hers for a few beats longer than necessary.
"Here, here," Jacob returned the toast. "Speaking of catering, Leslie, I believe our appetizers are nearly finished."
Leslie looked over at the outdoor kitchen and saw Mr. Cheng starting to plate some food. "Oh yes, of course, my apologies," she replied, quickly getting up.
Jacob chuckled. "None needed."
Leslie checked to see if anyone else needed a refill of their refreshments, before returning to the kitchen and bar.
Scarlet grinned at her once she arrived. "You seemed to get rather engrossed with that one fellow."
Leslie looked over her shoulder at Johnathan and Jacob talking, Johnathan glancing her way now and then, before looking back toward Scarlet. "Uh yeah, he's, uh, interesting."
"Interesting, huh?" Scarlet smirked as she started fixing the couple of drinks that the guests had asked for.
"Appetizers are up," Mr. Cheng then announced, setting three plates on a tray for Leslie to take over. "Oysters on the half shell, tuna tartare, and caviar blinis."
"Uh, thank you," Leslie said softly, eliciting a slight nod from the chef before he continued working on the next course.
Scarlet then placed the new drinks she had made on the tray around the plates. "Knock 'em dead," she encouraged.
Leslie returned with the tray, handing out the drinks to those who requested them, and relayed the list of appetizers. She took the tray around, allowing the guests to select which appetizers they wanted, before setting the plates down on a table near one end of the sofa.
Leslie then spent the next hour or so alternating between talking with guests and getting drinks and additional courses from the kitchen and bar. It was sometimes a job keeping up with the needs of all the guests, but she still occasionally found time to sit and converse with several of them.
At one point she approached a small group of guests sitting around one of the tables. She recognized one of the men from earlier—Victor, the older, flamboyant businessman with salt-and-pepper hair. He welcomed her warmly as she arrived, and she returned the gesture, her smile soft but polite.
“More wine for you, Mr. Moretti?” she asked, motioning at his half-empty glass.
Victor nodded. “Please, Leslie. And don’t be shy—sit with us for a moment,” he suggested, gesturing to the vacant seat beside him.
"Uh, I'd be happy to once I return with your refill," she slightly smiled. She returned to the bar to get a new glass of wine and carried it over to Victor, handing it to him, before sitting down in a chair next to him.
“How’s the evening treating you so far?” Victor inquired with a smile.
“It’s been ... busy,” Leslie admitted, trying to keep up her proper posture. "Everyone has been so gracious. It’s been a bit of a whirlwind, but I’m enjoying it."
Victor chuckled softly. "I imagine it can be overwhelming, especially with such a ... diverse group of personalities. Jacob does know how to assemble a crowd, doesn’t he?"
"Uh, yeah. I haven't had to cater to a group this large since my days as a waitress," Leslie admitted, looking around at the guests.
"Ah, so this must be old hat to you," remarked one of the guests sitting with Victor—David, the youngest of the guests.
Leslie turned to face him. "Yeah, although I was used to wearing clothes when I did it before," Leslie chuckled.
The group let out a laugh. Victor responded this time. "Yes, the job you are in is certainly ... unusual. But you are performing it with remarkable grace. A gathering like this requires a lot of attention to detail. Jacob knows that, which is why he has you here." His voice lowered slightly as if he were letting her in on a secret. "And I must say, you’ve done an excellent job of keeping everything running smoothly."
"Th-Thank you," Leslie's face reddened at the compliment.
"May I ask what led you to take this posting?" the third member of the group and the only female guest, Eleanor, inquired.
"Well, to be honest, the main reason was money. I'd guess that is the main reason why anyone takes it," Leslie admitted.
"Yes, but why this job? It's not like other jobs don't provide income," Eleanor further prodded.
"Well, yes. Part of it was wanting to keep the house I'm at now and stuff. It was going to be tough to work other jobs and still be able to keep everything. But I guess another part of it was I wanted to do something different. I didn't think of doing this, to begin with, and I guess I was skeptical about how much I would like it even after I applied. But I guess I've found that I'm enjoying this job after my first couple of appointments."
Leslie hoped her answer made a lick of sense, considering she felt like she started to ramble by the end, or that it answered the question.
"Interesting. I feel like Emily—the woman who worked in your position before you—was very similar. I remember when she first started. She was as nervous and unsure as you are about it. But she grew into the position brilliantly. I'm sure you'll do the same," Eleanor smiled.
"I hope so too," Leslie nodded. She then saw one of the other guests raise his hand to get her attention. "I guess I need to get back to work. Thanks for the chat," Leslie excused herself as she stood up, nodding at the trio.
"It was our pleasure," Victor replied, raising his glass of wine.
Leslie once again gathered a couple of drink orders, before fetching the final dinner courses of the night: grilled lobster tails, filet Mignon skewers, and seared scallops. She went around, allowing all the guests to take what they wanted.
At this point in the night, Leslie had started feeling more at ease. She had gotten involved in small conversations with most of the guests at one point or another and felt she was just another person at the party to some extent, despite her job of going back and forth refilling drinks and serving food.
As the sun set and the clock ticked toward 10 p.m., Jacob stood up and addressed the gathering.
"Good evening, everyone. I hope all of you have had an enjoyable evening so far," he started. The guests made sounds of approval or raised glasses of their drinks in agreement. "As you are aware, we get an excellent view of one of the 4th of July fireworks shows from here, and, per my watch, it looks like it is just about time for them to begin."
Leslie walked over to the gathering of guests and looked up at the sky to await the show. The first firework flittered into the air above the treeline and exploded in a shower of brilliant red. Another firework soon followed, bursting into a bright blue. Fireworks continued shooting in the air, eliciting "oohs" and "ahhs" from the assembled guests. Leslie enjoyed the show, happy for the brief respite before the next part of the night, whatever it brought.
The show continued for a good twenty minutes or so, finally concluding in a grand finale where multiple fireworks all exploded together in quick succession, a constant stream of popping and lights that filled the sky.
Finally, once the show appeared to be over, everyone let out a round of applause.
"I think they outdid themselves this year," Thomas cheered as he gave a standing ovation to the show.
"Does anyone need anything else from the bar?" Leslie asked, stepping in front of the group. A couple of guests asked for additional drinks, which Leslie walked over to the bar to fetch. Meanwhile, Dr. Cheng was putting the finishing touches on dessert for the night: an assortment of mini-cheesecakes.
"How are things going?" Scarlet asked as she made up the latest round of drink orders.
"Not too bad. It's gone better than I guess I would have expected it to with this group," she admitted.
"Not that I interact with them very often, but I find that most of Mr. Henderson's guests are very well-behaved. I guess those that are not aren't invited back," Scarlet remarked.
"Yeah, I guess. It's still strange to be hanging out with so many people naked and feel, well, at least not like I'm freaking out," Leslie laughed.
"I get it," Scarlet chuckled. "You'll get used to it, I'm sure. In no time you'll be hanging out with wealthy businessmen like it's second nature."
"If you say so," Leslie laughed with a little bit of doubt. "I'm not sure I'll fully get used to doing this."
With that, she took the drinks and dessert over to the guests and distributed them once again.
Jacob then stood up again. "Now that the first part of the evening is complete, I think we get to the next part. What does everyone think of playing some charades?"
"Sounds like an excellent idea," Raj agreed, added by agreement of several other guests.
"Excellent. What I propose we do is we split up into two teams. Our lovely Leslie here will be our performer for the night. One team will give her a prompt for the other team to try to guess. Whatever group gets the most points wins."
Leslie immediately started feeling anxious again. Performing charades in front of everyone? What if they gave her near-impossible to act out prompts? What if she was just bad at doing them? She barely noticed that everyone had formed into two teams: Charles, Raj, Johnathan, Thomas, and Eleanor on one team and Gregory, David, Victor, Henry, and Jacob on the second team.
She was soon snapped out of her stupor by Jacob talking once again.
"Leslie, if you will, team one will give you your first prompt," he suggested, motioning over to Charles' team.
Leslie nervously walked over and leaned over as Charles whispered the first prompt into her ear: going fishing.
Leslie nodded in understanding and let out a sigh of relief. She had gotten a pretty easy one to start. She stood in front of the group of assembled guests and briefly considered what she would do.
She then put one leg in front of the other, bent her back, and started making a motion with her hands as if she cast a fishing line and then started reeling it in.
“Fishing!” shouted David, grinning from ear to ear. “You’re catching a fish!”
"That's right." Leslie nodded in his direction.
"Alright, so that's one point to team one. Now it's our turn to give a prompt," Jacob noted. Leslie walked over to Jacob to get the prompt she was to perform next. Jacob leaned in close and whispered with a playful grin, “Your next prompt: a striptease.”
Leslie blinked and her cheeks flushed slightly, but she composed herself quickly, nodding in understanding. She stepped back to the center of the patio, letting out a soft sigh. She then went through her head about how she might perform this prompt. If this was going to be the tone of the game, she might as well embrace it.
The group quieted, their attention fixated on her as she began. Leslie slowly slid her hands up her body, pretending to pull down invisible straps from her shoulders. She then did a sexy walk before pretending to unbutton a non-existent shirt, flinging it aside dramatically. She then knelt as she removed her pretend pair of shorts, kicking them away.
The first team murmured as they considered what the prompt was while the second team knowingly watched. “A striptease!” Johnathan finally shouted, his deep voice booming over the chatter.
"Correct!" Leslie remarked, flashing him a smile. "I think whoever guesses should give me the next prompt," she then suggested, to the approval of everyone. She then walked over to Johnathan to get his prompt.
He smirked before whispering in her ear: "Giving someone a lap dance."
Leslie blushed again as she nodded and walked back out to the open patio. She only had an idea in her head of what a lap dance even looked like. How would she "perform" it in the open air?
She moved to try to show that there was a chair there. She then turned and started lowering herself, as if she were rubbing her butt against a person in the chair, rolling her shoulders and flinging her hair seductively. She turned around and acted as if she was straddling the figure in the chair, her hand holding onto the back of it. She leaned forward, acting like she was leaning into the figure.
"You're giving a lap dance," Henry then called out, to applause from the first team.
"That one was a bit tricky," Leslie admitted, as she walked over to Henry to get her next prompt.
"Washing a car seductively," Henry soon whispered into her ear.
Leslie nodded in acknowledgment and returned to center stage. She hoped this one would be pretty easy. She bent over, as if she was grabbing a sponge from a bucket, and twisted it as if to wring the water out. She then stood up, took a couple of steps over, and leaned over as she started wiping her hands as if she were washing the hood of a car with the sponge.
“A sexy car wash!” Charles shouted, laughing.
Leslie grinned and gave him a small bow. "You got it," she said, before walking over to get her next prompt.
"I want you to do a risque photoshoot," Charles whispered into her ear.
Leslie nodded with a smile and returned in front of the group. She decided to do a pose and stood there smiling as if she were waiting for the photographer to take photos. She then changed positions and did the same thing, making sure to give the guests she was performing in front of a good show while she was at it.
It took a while for the people on the second team to figure it out, but finally, Jacob spoke up. "A sexy photoshoot?"
"Close enough," Leslie laughed. "I wasn't sure if you were gonna get that one or not."
As the night went on, the game continued to escalate in its playful and risqué nature. Each prompt drew more laughter and applause, and Leslie found herself having fun despite her earlier nerves. She was having fun performing for her audience, figuring out ways to perform the sometimes tricky prompts.
By the time midnight rolled around, Jacob declared the game to be complete.
"That was an excellent game if I may say so myself. Leslie, you did a marvelous job!" he complimented, leading a round of applause, which caused Leslie to blush again.
"Hey, hey!" Victor cheered, raising his nearly finished glass of wine.
"I think you've done such a good job, you deserve to pick how to entertain us to complete the evening," Jacob continued.
This suggestion took Leslie aback a bit. He was letting her decide what to do? A series of thoughts ran through her head. She wanted to do something erotic, but just how erotic should she get? Should she dance? Maybe playfully feed some of the guests something like strawberries? She was trying to decide.
That's when her eyes met with Johnathan's again, and she got a slight smirk on her face. She looked around and saw the small bench she had used during her trial job there. She picked it up and set it down where she had been standing in front of everyone.
"Alright," she smirked, "how about we spice things up a bit?"
The group murmured in intrigue as Leslie turned toward Johnathan. She had been drawn to him all night and decided that she should take advantage of that attraction while she had the chance.
“Johnathan,” she called, gesturing to the chair. “Why don’t you join me on the bench?”
Johnathan’s grin widened as he stood, the other guests whistled at him and teased him. “How could I decline an offer like that?” he teased, as he took her hand and walked over to the bench before taking a seat.
Leslie kneeled over him from behind and lightly rubbed her butt up against him. She immediately felt flush, giving him an actual lap dance in front of an audience. But that is what she was here for—to entertain guests—and she felt she might as well have fun while she was at it.
She tried to be captivating without appearing too sleazy. She wanted to portray that she was having fun and was doing this because she wanted to, not because it was "just a job." Johnathan, who kept his hands away at first, eventually put them on her waist as she slowly ground into him. Leslie bit her lip as she felt the train engine that was her passion picked up steam and she wasn't sure she was going to be able to stop it.
She turned around and straddled him, eliciting some whoops from the watching guests. She continued to grind herself into his groin and she could feel him starting to get hard through his slacks. She wrapped her arms around his neck and looked into those handsome, green eyes that she had found so alluring all evening. She didn't care at this point that he was nearly twice her age. She thought he was sexy, and she wanted him.
"You're definitely something, Leslie," he grinned towards her as she continued to work, his eyes taking in every curve on her body as he started to slowly move his hands up her torso. "You've made this a night to remember."
"It's not over yet," Leslie breathed out a sigh. She was full-on grinding her pussy and clit against his hard cock through his trousers, and leaned in, pressing herself against his chest. She then put her mouth right next to his ear and whispered. "I so want to fuck you right now."
"So do I," he whispered back.
Leslie's heart fluttered and she felt a chill run through her. "Are you sure? In front of everyone?" she whispered back.
He let out a soft chuckle. "You're here to entertain them. Why not give them a real show."
This was all the encouragement Leslie needed. She pulled away from Johnathan, his slacks smeared with her wetness where she had been grinding against him. She unfastened his pants and then looked up at him. "If I may?" she inquired as she grinned at him.
Realizing what she was asking, he lifted himself off the bench just enough to allow her to pull his slacks and boxers down, drawing a new round of whoops and hollers from the guests. Leslie leaned over and took his cock into her mouth, massaging his balls with one of her hands. She twisted and twirled her tongue around him and could hear him let out a soft moan as she did so. She knew she had him. She wanted him. And nothing and no one was going to stop her.
She then slowly pulled her mouth away, dragging her tongue out of her mouth, sliding it up against Johnathan's cock until the tip of her tongue reached his head, where she slid her tongue around him one more time before standing up and straddling him again. She sat on his lap, his cock pressed against her pussy and clit as she started grinding him again, letting out a soft moan while she put her hands around his shoulders. She felt herself get hotter as she could feel her clit rub against his shaft.
She looked into his eyes again, silently asking if he was ready. The look he flashed in return gave her his answer.
She raised herself and took a hold of his cock, then slowly lowered herself down on top of him. She cooed as he filled her up before they started moving their hips together. She leaned into him, shifting her position to find the best angle for him to hit the erogenous zones inside of her, and to allow her clit to grind against him as they moved.
His hands moved up and down her torso. He occasionally squeezed her breasts and nipples, before sliding his hands back down to her hips and moving them back up. Leslie could tell the watching crowd was utterly captivated by their performance. She was giving them what they wanted, and she was making sure she enjoyed every second of it as well.
She could feel the tingle and heat inside of her build as he continued to slide in and out of her, keeping up a good but not overly intense rhythm. She grasped his shoulders and leaned into him, gasping softly as his cock continued to rub against her most sensitive areas.
This sex was different than any she had ever had. Sex with past boyfriends was romantic and intimate. Her session with Zachary had been wild and lustful, but this was something different—her attraction to Johnathan made it feel more meaningful than just a fling, but it still had the edge of a moment of passion. Leslie had never had a one-night stand before starting this job, and she wondered if this might be the feelings one had when engaging in one.
Her heartbeat increased and she felt ever hotter. Everything around her closed off and it was just her and Johnathan embracing and having a moment. She let out a sharp breath as her body tightened. She leaned into him harder, letting out a more audible moan as the orgasm shuddered through her. Johnathan also let out a soft moan, perhaps a response to her vagina squeezing itself around him. Her orgasm wasn't the most intense she ever had, but it felt like it lasted longer. A sustained moment of pure ecstasy as she embraced him, hoping this feeling would never end.
Finally, it let go and she had to keep from collapsing onto his chest. She suddenly became aware of the warm summer breeze blowing over her sweaty back as they continued to work.
"I'm close," he whispered into her ear not too long after.
"It's okay," Leslie breathed back, Johnathan nodding in understanding.
He thrust into her one last time and let out a moan as he shot two, three, four loads of cum deep inside of her. Leslie grasped onto him as he did so, a feeling of immense satisfaction filling her.
She was soon brought back to her senses as she heard more cheering and hollering from the assembled guests. She looked in their direction and found most of them giving a standing ovation. She felt a bit flush but then felt a sense of pride. This is what she was here for: to entertain, and boy did she put on a show.
Johnathan brushed away Leslie's hair from her face, causing her to look back at him.
"That ... was incredible, Leslie. Thank you," he said warmly. It wasn't a look of conquest or a brag but of genuine appreciation.
This made Leslie blush even harder. "No, thank you," she smiled back, before leaning forward and gently kissing him.
She then extracted herself from him and stood up, a stream of their combined juices running down her leg. She then glanced over and noticed Scarlet grinning at her from the outside bar, also applauding.
Johnathan put himself back into his pants and adjusted his clothes. He then stood up and took Leslie's hand and raised it in the air. "To Leslie, our host!" he announced, leading to another round of applause and cheers with glasses, which caused another round of blushing by Leslie. She almost felt lightheaded with the events of the night still racing through her head.
The next several minutes felt like a blur to her. Jacob thanked everyone for coming, and they in turn thanked him for his hospitality. Everyone then made their way back through the house and back outside the front door as valets started bringing the guest's cars around.
Several of the guests complimented Leslie on a lovely evening on their way out, and she politely thanked them.
"Once again, thank you for the unforgettable evening," Johnathan remarked as he bid her farewell.
Leslie thought she felt her stomach do a flip. "Uh, yeah, you too," is all she could manage to get out, and she immediately felt like kicking herself for not saying something better. He just grinned at her before getting into his car.
Soon all the guests were gone, leaving only Jacob and Leslie. She had unconsciously wrapped her arms around herself, not from being cold, but from a futile attempt to contain the emotions swirling inside of her.
"How are you feeling?" Jacob asked, causing Leslie to jump. Her mind was elsewhere and suddenly being addressed surprised her. "Sorry, I didn't mean to surprise you," he quickly added.
"Huh? Oh, no, it's okay. Um. I feel ... good? I had fun tonight. And Johnathan ..."
Jacob let out a grin. "You definitely made his night, that's for sure. I was surprised. I felt like you two might have a connection there, but I wasn't expecting that. I doubt he was either," he laughed.
"Me neither, honestly," Leslie mused. "But once I started ... I knew I wanted him. I had to."
Jacob chuckled. "I think we could all tell you two were, well, connected by more than just a desire to have fun. There was a spark there, and that made it all the better. I'm still impressed though. You've grown so much in so little time."
Leslie felt a strange bit of embarrassed pride. "Believe me, it feels like a whirlwind for me as well. But what I've come to realize more and more is ... this is me. I just never knew it. I guess I was afraid to explore it. But now that I've started, I want to see what else I'm capable of."
Jacob leaned over and gave her a gentle kiss on the cheek. "I'm sure you'll have plenty of opportunities. However, having said that, you should probably consider getting some rest. Talk to Stephanie when you're ready. We've made a room available for you to stay the night. I don't want you driving back in the middle of the night, especially after all of that."
Leslie nodded. "Thank you, sir."
Leslie made her way to the showers and stepped in one, turning the water on a bit hotter than usual. She could still feel her heart beating. She knew this night was only a fling. Would she ever see him again? Maybe. But that wasn't for her to decide. She didn't even know if he already had someone in his life, although if he did, he certainly didn't object to what they did. Besides, he was twice her age. Even if by some wild chance a thing with him was possible, it probably wasn't realistic.
"Hey, mind if I join?" a voice asked from the other side of the curtain. Leslie poked her head out and saw Scarlet standing there naked, except for the towel she was holding in front of her.
"Uh, no, uh, come in, I guess."
Leslie stepped aside as Scarlet put her towel on a rack and stepped in. "Sorry, I just wanted to chat," she added, slightly blushing. "You were ... incredible tonight."
"Uh, thanks. I guess I didn't consider that you were still there," Leslie answered with a somewhat awkward chuckle.
"You were going like no one was watching. You looked so into it, and so did he. It was almost like watching art somehow," Scarlet smiled as she started to soap herself up next to Leslie. "I—I kind of admire you for it. I definitely couldn't do something like that."
Leslie let out a little laugh. "Are you sure? A month ago, I would have said the same thing and yet here I am." She let out a sigh as she also continued to shower herself. "If I had told month-ago me what I did tonight, she would have told me I was crazy. And maybe I am. But if this is crazy, then I guess I like being crazy."
"You handle everything with such confidence. I think that is what allows you to do all of that. I could tell that about you from when I first met you," Scarlet continued, blushing slightly. "Nothing seems to bother you."
"Oh, I'm not sure about that. Maybe I'm just good at hiding it. When I started here, I was unsure about, well, everything," Leslie laughed. "But thank you for the kind words. It means a lot."
"Uh, you're welcome," Scarlet nodded. "Anytime you need a boost."
The pair continued chatting about the night and working for Mr. Henderson in general before Leslie turned the water off and the pair walked back into the locker room, putting their street clothes back on.
"Are you staying the night too?" Leslie inquired, glancing over at Scarlet as she slipped her shoes on.
"Ah, no. Mr. Henderson offered, but I have work—another job—tomorrow so I should get back home."
"Oh, I see. Then I guess I'll see you around then!" Leslie replied and waved goodbye.
"Ah, yeah. Later," Scarlet answered with a slight blush, waving in return.
As Scarlet exited out one of the doors that went out to the staff parking lot, Leslie couldn't shake a certain feeling. Had Scarlet been flirting with her? The compliments, the blushing—she couldn't help but feel like Scarlet was trying to find a reason to spend time with her. Leslie gave herself a slight smile thinking about the prospect as she found Stephanie waiting for her in the main staff room.
"Let me show you to your room," Stephanie smiled, motioning Leslie towards one of the doors exiting the staff area.
"Thank you," Leslie acknowledged, nodding in return.
Leslie expected Stephanie to perhaps make small talk about the night as they walked, but she didn't. She simply led Leslie up a set of stairs to an exquisitely carved dark wood door.
"If you need anything, you know my number," Stephanie remarked before opening the door for Leslie.
"Uh, thank you, I will," Leslie nodded before stepping inside.
What the fuck? That was the initial thought in her head as she stepped inside.
"Have a good evening," Stephanie mentioned as she started to pull the door.
"Uh, yeah, you too," Leslie answered, turning around just in time before she closed the door. She then looked back at the room.
There was a large window that gave a view of the surrounding wilderness outside, the city—Leslie's college town—lit up in the distance. There was a full sofa and a couple of other seats set in front of a large TV that Leslie figured had to be sixty or seventy inches. Behind the couch was a queen bed made with several blankets and pillows. She knew she shouldn't have been surprised about how extravagant the room was, but she still felt like she wasn't worthy of such accommodation.
She looked over at a clock on a table next to the bed. Nearly two o'clock. The adrenaline from the night was still making her feel alert, but she knew that wasn't going to last for much longer. She pulled the top cover off the bed and hopped in.
She ran through the night's events in her head. She felt her body start to crash as the late hour caught up with her. Strangely, the audience and her expectation to entertain had perhaps made her bolder than she otherwise would have been. She never would have thought to even approach a man like Johnathan, much less fuck him like that, normally. But the expectation of entertainment provided the perfect excuse to let go of her inhibitions and fear and allowed her to go for it. Maybe it would only be a one-time thing, but if it was, she was glad it was a memorable one. As thoughts of the night's events once again swirled through her head, she fell asleep.
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It was nearly noon by the time Leslie woke up, the sun lighting up her room. She slipped out of bed and yawned. She went to the bathroom in the attached room before going downstairs.
"Ah, Mr. Henderson apologizes, but he had to leave for work," Stephanie spoke up upon seeing her. "He did want me to relay to you once again that he thought you were exemplary last night. Also, Mr. Chambers, the gentleman you—entertained—last night has left you a $1000 tip. We will make sure to include it in your payment."
Leslie felt like her chin might hit the floor. "A—a thousand-dollar tip?" she asked, making sure that she had heard correctly.
"That is correct. 'To thank the lovely Leslie for an incredible evening' I believe was the message he relayed with it."
"Uh, well, I wish there was a way to thank him for that," Leslie stuttered, somewhat at a loss for words.
"I'm sure he is aware of how much you appreciate it," Stephanie remarked with a slight smile. "Would you like us to prepare you some lunch before you go?"
"Huh? Oh, no, I couldn't ask you for that. I'll grab something on my way back," Leslie answered with her head in a new daze.
"Very well. We will wire you your payment shortly. I'll let you know when your next appointment with Mr. Henderson is."
"Th-thank you," Leslie replied with a nod.
With that she walked out to her car, her head still spinning. Come Saturday, the deposit hit her bank account. With the tip, it was pretty much enough to cover an entire month's worth of expenses, and she was still only in the first week. She still thought back fondly on her night with Johnathan but also looked forward to what might be next.