"The Inside Man" (A Chapter From THSHC)

[CutiePie1997]

"The Inside Man"

A Chapter From
"The High School Hookers Club"

Closed to FireyIce


NOTE TO THE READERS:
This thread begins at a point in the timeline
later than that at which the Main IC Thread is now.
You have two choices:
One, begin reading this thread now, or...
Two, wait until the Main IC's time line catches up to this thread,
at which time I will post a link that will bring you back here.
That way, you can read the threads
in time line order.​

Pamela Dryer: profile, image, and her dress, with which she is wearing a sheer white shawl that still shows off her bosom well.


Pamela was not thrilled with the situation at hand! She'd come to the lounge of the Virken -- a beautiful, elegant, and expensive downtown hotel -- to meet a prospective client of her new business, playfully referred to as The High School Hookers Club. That prospective client, however, turned out to be a principal from Harrison High College Preparatory School ... the school at which the nearly-19 year old was still a student.

She was about to turn around and walk out, abandoning the meeting and possible future income she's earn from Mister Satoshi, when she remembered why she was here. Pamela had been facing the possibility of having to move out of the Malibu beach house that had been her home since she was in her early teens. The home owner and benevolent patriarch to Pamela, Harvey, was relocating to Naples with his wife, Brigitte, who had been born in Italy and still had family there. She had demanded that Harvey net some cash from the beautiful estate, which meant either selling it or leasing it to one of the many beach house rental companies popular along the Californian coast line.

Either way, Pamela had been looking at relocating as well. That was until Pamela -- a well paid escort -- made a deal to pay Harvey the requested rent of $4,000 a month by expanding her business. And in a very short amount of time, Pamela had accumulated a handful of class mates into the Club. She was still a long way from paying the rent on the beach house, but Pamela was feeling good about her direction. At least, she had been until she walked into the lounge and saw Mister Satoshi.

Pamela had protected herself from such potentially embarrassing and career ending meet-and-greets via a two part policy on taking new clients. First, all new clients had to be referred by current clients. This gave Pamela the opportunity to vet the prospective John. She did thorough online searches of them, looking for any indication that they were law enforcement or any other sort of security or privacy concern; then, if they were a local business type, even dropped into their place of employment to take a quick look around and ensure further that they were who they said there were.

(She'd once discovered that a prospective John was actually an online journalist eager to do a story on underage prostitution. Pamela had had to disappoint him, first by having the existing client -- who was no longer a client due to his indiscretion -- tell the journalist that Pamela wasn't available for new clients; and second, by pointing out that all her girls were of age, therefore she had nothing to contribute to his article in the first place.)

The second part of her protection policy was that the referring client told the prospective client never to bring up money. The future John was warned that if he and Pamela got into an explicit conversation about erotic situations -- fantasies he wished to fulfill, for example -- and money was mentioned, she would simply stand and walk away, never to be seen by him again.

It wasn't the second part of the policy that was disturbing Pamela at this point, of course. It was the first. The referring client had given her a name, description, and place of employment of his horny friend, and Pamela had, of course, checked the prospective John out. But ... the man she'd checked out wasn't this man, her Principal. So ... someone had lied. One of the two clients had fibbed for one reason or another.

Again, Pamela could simply turn away and walk out of the lounge. Mister Satoshi hadn't seen her yet, and even if he had it wouldn't have meant anything to him. The two had never even formally met. He hadn't been at Harrison long, and Pamela hadn't been sent to the Principal's office since she was, what ... 15 years old?

She knew it was better just to walk away. But Pamela needed two things: she needed to know how this had happened; and she needed Mister Satoshi's money. She was making much more money that she had been as just an escort, but she was still a long ways from paying the four grand a month to keep Harvey or -- more specifically -- Brigitte happy.

She drew a deep breath, let it out slowly, then made her way slowly through the rather dark lounge to Mister Satoshi's booth. She hesitated near the table as he looked up and asked with a wide smile as she offered a hand, "Mister Johnson...? I'm Pamela."

 

[FireyIce]

Juston Satoshi: Image

Juston had been waiting for a little bit as he sat at the table in the Virken’s very elegant dining lounge. The lighting was pretty well for such an elegant place. It allowed for a more private-based tone, however, still allowed the room to be seen. He had already checked in for the night and had his bag taken up to the room. This meeting was very beneficial as he had already planned on being out of his house for the night. He had recently had his family visit and was having someone work on cleaning his place, so the prospect of having some “company” for the night was a win-win in his mind.

He heard the footsteps of Pamela approach as he closed his email on his phone and turned it off; setting it on the table so she would be able to see the screen fade to black. As she extended her hand he stood up and took it, kissing it gently as he moved over and helped her sit down. “It’s Juston, actually,” he pointed out without wanting to sound disrespectful. “It’s nice to meet you, Pamela,” Juston said as he sat back down. “I hope you didn’t have any problems getting here or finding this place,” he added as he looked and studied her face, admiring her beauty.

“None at all,” she had replied as she looked back at him.

It wasn’t very long before the server had come over after seeing Pamela arrive. Once she did she asked if they needed anything to drink. Juston didn’t even bother looking at the wine list as he had already glanced over it beforehand. “I’ll have a glass of red wine from Spain,” he mentioned to the server. “And for you, Pamela?” he asked inquisitively for the server.

“I will have a white wine,” Pamela replied as she finished looking over the choices. She had also seen the expression on the Server’s face as she looked in her purse and pulled out her ID. She could see the expression on Juston’s face as well as the server looked it over and handed it back.

The small exchange between the server and Pamela brought a bit of relief to his conscious. For all he knew, she was at least old enough to drink. The idea that she would be a minor had been very quickly diminished. “You look very lovely tonight, Pamela,” he complimented to her as he tried to make some small talk, not wanting to bring up anything for later until after they had left and headed upstairs. There had been only two other times he had hired an escort, so he was familiar with the customs and courtesies that went with them. “Have you been in California all of your life?” Juston inquired wanting to know a little bit about her past.

“Thank you very much,” Pamela said with a wide smile. “You look pretty handsome yourself,” she replied, looking over his three piece suit that he was wearing. Though he could have arrived straight from work, he still made the decision to go and get changed into something a bit more elegant for tonight.

This night was something that was long overdue. Since his promotion towards the end of the last school year, he was keeping busy and, until recently, he had just broken up with his girlfriend a few months ago. He had wanted some intimacy of late and once he heard Gerald, one of the members of the country club he went to, had mentioned how the lobbyist who was in town a while back, got a glimpse of Pamela, Juston was curious. Luckily, he was able to get the number and have this meeting set up, though it seemed to be a very complex way. He figured with Gerald being a politician’s aide, it shouldn’t be a surprise.

 

[CutiePie1997]

Pamela had sat across a booth table with a lot of men during her time as a prostitute ... or escort as was more applicable until she made the decision whether or not to get naked with a client. It wasn't a requirement, of course. There had been times in the past when she chose not to have sex with the man meeting her. Sometimes, things just didn't click; and other times, she'd sensed an issue -- even a danger -- that she'd preferred to avoid.

Of course, Pamela should have avoided this just as soon as she recognized the administrator from Harrison High. But, Pamela was eager to learn just how she'd come to be sitting across from her school's principal when she thought she'd be sitting across from a political insider from the State Capital.

As they chatted, Pamela found herself studying Juston in the same way she studied all of her prospective clients. After a rough, abusive childhood, several months living on the streets, and then suddenly finding herself living on a Malibu estate surrounded by rich people whose money she could easily get if she only found a way, Pamela had become very good at reading people. And there was definitely a lot to be read in Juston's expressions and body language. She profiled him as being lonely but not desperate; as seeking new experiences though not necessarily being an seeker of great adventures; and ... something else that she couldn't quite put her finger on until she began to ask her standard questions.

"So, tell me how you know Gerald?"

Juston answered as he would, after which Pamela asked, "And ... what did Gerald tell you about me ... about what you could expect tonight?"

This was where Pamela often learned a lot, not only about the prospective client but about the client who had referred him as well. Sometimes the referrer gave very intimate and graphic details of what Pamela could offer the referred. And other times, the only information that had been passed was There's a woman you should meet if you want to have a good time.

Tonight, of course, Pamela was more interested in why she'd been given a fake name, profession, and background for Mister Jameson Johnson and not Juston Satoshi. She let the principal tell her what he wanted, then came to the conclusion that Juston had not been the primary behind the ruse being perpetrated.

"You are not who I was told you were," Pamela said very politely and softly. She watched the reaction in his expression, then continued, "I suspect that our friend Gerald ... with whom I will have some words about this at a later date, was more eager to see you have a..."

Pamela hesitated a moment, picking her words. A good time, of course, implied imminent sex. And though she didn't know Juston had a room upstairs already, it wouldn't have mattered to her at this point because she was still in the escort not prostitute frame of mind. So she continued, "Have a nice evening ... than to protect me from potential ... problems."

Still profiling Juston's expressions and body language, Pamela was getting the distinct impression that the man had no idea of what she was speaking. She said, "Our friend Gerald said your name was Jameson Johnson ... that you were, like he is, a lobbyist from Sacramento ... and that you were in town for a meet and greet with a local State Congressman ... as well as a meet and greet with me."

She cocked her head a bit, smiling politely before asking, "So ... since we both know that that isn't true ... why don't you tell me who you actually are ... what you do for a living ... and what you're hoping to get from your time with me tonight."

From your time with me tonight. As Pamela listened to Juston's response, she thought about that part of her question. She hadn't actually come here tonight to fuck a Jameson Johnson. She actually had another of the Club members on standby, awaiting the word that her appointment was a go. But after seeing that the client-to-be was a school administrator, Pamela was concerned about setting Juston up with a student who -- unlike with Pamela -- he might recognize.

No, if this appointment went ahead ... Pamela would be the one servicing the principal tonight.

If...!

 

[FireyIce]

Juston listened to Pamela as she asked a few questions. He saw she was looking him over. Not being 100% sure why, he figured it was to see if there was something she should be concerned about. As she was asking the questions, the server came back with their drinks. Juston picked up his glass and sniffed it before taking a small sip. He did think it was strange that she had been expecting someone else who he wasn’t. He figured the initial introduction with calling him Mister Johnson was just to make sure she was who he was waiting for.

Once he was done with his sip, he set the glass down and cleared his throat a little bit before answering her first question. “I am a member of a country club in town and I’ve seen Gerald a few times, nothing major. Until recently I didn’t even really knew what he did. I just knew it was something descents enough in order to be able to afford a membership.” He watched as Pamela took a drink of her wine. “Well, the other day he was in the sauna with a couple of us and mentioned how he helped, working as an aide-slash-advisor to political individuals, set up the meeting between you and the lobbyist. Though he described you, it wasn’t well enough. Though I was curious and we talked for a bit after and I gave him my name and number and told him to see if he could help arrange this,” Juston started to glance at the menu as the server came by to check on them.

Once the server was gone, he thought about what Pamela had inquired on what to expect. “This isn’t my first rodeo, so to speak, so I didn’t ask for any details. I didn’t want him to say anything that could be viewed as being arbitrary or misleading so, I think the goal for the night would just be viewed as one simple term: companionship.”

Juston was a bit surprised, and he knew that he was showing it, when she mentioned that the information she had received had been highly misleading. He was wondering in his mind on how such a difference could have occurred. He tried to make sure he was remaining calm without wanting to have a scene or anything happen if he didn’t give a very plausible reason as to why this had occurred. “I do apologize for the miscommunication of information. As far as I can think he might have been looking at someone else’s contact information when calling you?” he suggested as he started go rub his chin. He could tell that the “date” wasn’t going as smoothly as either of them was hoping. At least he knew he wasn’t the source of this debacle.

“My apologies,” he said as he started to realize that she had asked about his real name and work. “My name is Juston Satoshi. I work in the education field in more of an administrator role than teaching role,” he answered not wanting to give away the fact that he was a principal. Or for what school for that matter. Though she may not be a student, she may still know people who went to Harrison Prep. The last thing that he needed was a nice big scandal and to explain this to the board. “As far as what I want for tonight, like I said earlier, would be companionship,” he answered truthfully. “My ex and I broke up a while back and work has been fairly hectic, so I figured I could use some ‘me’ time tonight and have someone to enjoy the evening with. Whether it ends up being just drinks and a nice dinner or something more in my room that I have for the night, can depend on how things go,” Juston said with a slight grin. “I’m sorry I’m not who you were expecting – and I would be lying if I didn’t say that I wouldn’t love to be a-fly-on-the-wall for your conversation with Gerald – but if you want to end things, I would fully understand.”

He waited patiently for a response from Pamela to see if she was going to cancel the rest of the night or if she felt that he was being honest and sincere. While he was waiting he had looked at what he was going to get for his meal. “I would like you to know,” he started to say in hopes that she would still be willing to stay with him for the night, “That I have nothing to gain by lying to you. You seem like a very smart lady and I know that I would be suffering multiple consequences if I was lying, Pamela.” He thought that this would help solidify his reasoning to her.

 

[CutiePie1997]

As she listened to Juston's answers, Pamela concluded that he was being very sincere: about how the misunderstanding had occurred, about who he was, though he left out details he didn't know she knew; and about how he wanted to spend the evening in her company. Of course, the latter hadn't been in question. Few men who saw Pamela dressed as she was and got a chance to sit and talk with her a bit did not at some point yearn to be with her in that most intimate and erotic of ways.

"So, tell me, Juston ... education?" Pamela said with a friendly smile, wanting a change in subject. She sipped at her wine, continuing, "Teaching, how rewarding ... to know you are imparting a life time of knowledge to young students."

Pamela wasn't expecting more details about his specific position. It was already obvious Juston didn't want her to know which school employed him or even the position he filled. But they chatted for several minutes about the general field, during which Pamela implied -- also without great detail -- that she was a sophomore at one of the local State Universities, majoring in business.

By the time a lull in the conversation arrived, Pamela had already made her decision. She smiled to Juston and asked with a flirtatious tone, "So ... did I understand that you have a room?"

The expression on her face couldn't be misunderstood...

 

[FireyIce]

He watched, noting how elegantly she was acting. Small things, such as how she held the wine glass, to how she continued to look at him during her sips. There was no doubt, whether she was just acting or not, that she was giving him her full attention. He listened to her bring the conversation back to education. “Yes,” he started to say, “I went to school and studied back out east. I taught in Brooklyn for a few years before coming out here.” He, too, took a sip of wine before continuing the conversation, “My parents came here from China, worked hard and taught me to work hard and learn a lot. I’ve always been good at teaching and helping, so it felt natural for me to take that career path,” he admitted.

That was the catalyst for the conversation for a while as they talked and ate. As such, he figured the lack of details about her studying in college were for safety precautions. Perhaps they were a ruse, to help feign interest; however, he didn’t mind at all. It wasn’t until they were eating when the mentioning of the room came up. “Yes,” he said as he finished his meal, “I did get a room here. Just to clarify, like I said earlier, I staying here was going to happen regardless since it’s my small vacation away from a small vacation. I didn’t want you to think it was for a single sole purpose,” he said with a slight grin after seeing her expression. “Would you like to see it?” he inquired with his grin already knowing the answer.

“I would love to,” replied Pamela as she took another few sips of her wine. Both of them had consumed a decent enough amount; however, nothing to where either of them would have been drunk.

Once the server came by, Juston had requested to have the meal and drinks added onto his bill for the room. He gave the keycard so that it could be swiped onto his bill. Once the server returned with it, he thanked them with a generous tip and stood up. As he did, he walked over to Pamela and offered his hand. “Shall we?” he asked as he helped her up. It was a small trip to the elevators, though it felt longer. Once they got in, he selected the level and waited as the elevator took them to the floor.

As they got out, he escorted her to the room, entered the keycard and heard the metallic click as the door became opened. Once inside, he watched as she took in the view of the room. It wasn’t a penthouse or suite, though it was close to it. The thing he learned about the Virken is that the rooms acted as if they were on a class system with the top being the fanciest. Though it was several floors down, it was fairly exquisite. “It looks very lovely,” he heard Pamela say as she let go of him and looked around a bit, drinking it all in.

After taking his jacket and vest off, he undid his tie and tossed it with the other two items. Then he walked over towards Pamela, admiring her beauty with the room. It looked like it had definitely fit with her clothing style. Hell, he wasn’t even sure if she had been this high up. For all he knew she had been on the top floor. As he got closer, he stopped near her and lightly placed his fingertips on her chin, slowly turning it to where she could see him in a closer setting. In that moment, everything felt right to Juston, as he leaned in and kissed her gently on the lips. He could feel her lips pressing against hers as his other hand moved onto her side and slowly slid down towards the small of her back, pulling her closer to him. Once the kiss broke, he looked deeply into her eyes. “One of us is here on business and the other is here on pleasure,” he pointed out, “But I think we can both have some fun,” Juston added as his hand on her chin moved down to the other one as he grabbed her tight butt. As he pulled her closer, there was no doubt that his erection that was starting to form was going to be misread.

 

[CutiePie1997]

It was a nice room, better than most in the city and even better than most in this hotel. But it wasn't the penthouse, which -- about which Juston was wondering -- Pamela had in fact been in ... twice.

She spent the first minute or two admiring the space and the view, then turned to stand before the tall windows behind which the spectacular bright lights of the cityscape contrasted with the now black sky. She knew that the sight of her like this caused men to stiffen with eagerness. As he neared her, Pamela untied her shawl, dropping it to a nearby chair.

Their first kiss was soft and loving, as if the first between real lovers. Pamela smiled, pleased. She loved kissing, yet there had been many clients whose mouth her lips had never touched. Kissing could be a very personal thing, part of what Pamela called the Girlfriend Experience. Some men didn't want the Experience: they wanted to get their cock sucked, then dunked into a tight, young pussy, maybe even into an even tighter anus. If they wanted to kiss, they'd go home to the little wife who didn't do all those other nasty things anymore, if they'd ever done it at all.

As she felt Juston's hand slip to her back, she pressed her lips harder to his, parting them for a bit of passion. He pulled her closer, telling her...

"One of us is here on business and the other is here on pleasure ... But I think we can both have some fun."

As Juston pulled their bodies together, Pamela felt his erection pressing against her lower belly. She smiled, kissed him again, then whispered romantically, "No one's here on business tonight, Juston. You paid for me for my company in the restaurant ... for drinks and dinner ... good conversation. I gave you that. Our business ... is over."

That was, essentially, true. Pamela had never once guaranteed sex to a client. And while most if not all of them had expected it, most if all had also known that if she chose not to suck or fuck them, that was entirely her choice. Legally, she was an escort. Her guarantee was polite, even romantic and intimate companionship ... not sex. But, of course, how many men would be content after paying $300 for companionship for dinner and drinks, right? Particularly after having to also pay for that dinner and those drinks?

Pamela was a realist, though. How many referrals would she get if she chose to engage in sex less frequently? She'd often found it ironic that while most girls her age were trying to avoid a reputation of being easy, Pamela thrived quite literally on having just such a rep'.

Pamela pulled from Juston's arms, backing away slowly. In her four inch heels, her hips demonstrated a little extra swing which got her an ogle as she also ogled Juston. With a devilish smirk as she added, "I didn't come up here for money..."

She turned, facing the floor to ceiling glass that looked out onto the sparkling city as she said over her shoulder, "I came up here for the same reasons you did."

As she leaned forward and pressed her splayed fingers against the glass, Pamela suggested about her dress, "This thing's a bit tight. Maybe you could help me out of it...?"

 

[FireyIce]

Juston watched as Pamela broke away from their kiss and his grip. “Well, I’m glad that we have a mutual understanding of what we’re doing up here,” he told her with a sly smile. He watched as she slowly swayed her body over towards the window. As he watched her take in the view, he slowly made his way closer as well. Just like her he was also taking in the view as well as a better view of Pamela’s body.

There was a slight smile as she mentioned that her dress was feeling tight on her. “It would be my pleasure to help you out of it,” he said with some enthusiasm while still taking his time to get over to the window. Once he got over towards her, he moved his hands onto her hips at first, leaning down and gently kissing Pamela on the neck. With the companionship she had provided him tonight, especially with the miscommunication from earlier with her getting the wrong information, he wanted to make sure she was well taken care of.

Juston slowly moved one hand slowly up her side, feeling the soft fabric on his fingers as he made his way to the top of her dress. After a few seconds, his fingers found the zipper which he took his time slowly unzipping it. As the dress started to peel away, he noticed the back of the black bra. As the dress continued to come unzipped, Juston saw the matching panties that Pamela was wearing. Once there was no more room for the zipper to unravel anything else, he gently grabbed her hands, his fingers intertwining with hers for a few moments as he leaned back in to kiss her again. As they kissed this time, he slowly started to turn her around so she was now facing him.

After a moment of making out, he moved his hands back up and started to pull her dress down as their kiss broke, exposing her in just her strapless bra and panties. “You look even prettier with your dress off,” he mentioned as he took his time admiring more of her body. As he took her hand, he helped her step over the dress on the floor and slowly led her to the bed. As he started to lay her down gently, he took the opportunity to feel more of her exposed skin, feeling how smooth and silky it was as he stood up and began to unbutton his shirt while looking down at her. He moved his hands down and undid his pants, sliding them down before getting into bed with her, making sure that they were both in at least their undergarments as he held her closer, feeling her body resting against his.

 

[CutiePie1997]

Pamela may have been working, but she was enjoying herself as well. Juston's hands caressed over her body in a way that sent a chill up her spine, causing Pamela to giggle.

On the bed and parting her thighs, Pamela wrapped her ankles around behind Juston's thighs and pulled him to her. She was in her Girlfriend Experience mode, meaning Juston's experience for the night would be indistinguishable from that he would get from an established lover dedicated to his pleasure and satisfaction. Their kisses were passionate, erotic ... as her hands played over his body as his had over hers.

Eventually, with the feel of his firm cock pressing against her panties, Pamela whispered, "I want to make you happy, Juston." She kissed him again with open lips, flicking the tip of her tongue at his, as she asked, "What can I do to make you happy?"

She kissed him again, then smirked devilishly as she added, "Anything ... to make you happy."

 

[FireyIce]

Juston listened to Pamela’s giggles as he caressed her body. He continued to kiss her on the lips, chin, neck, wherever the desire was. He smiled a bit as she pulled his body closer to hers. As their hands felt each other’s bodies, he knew this was going to be a very wonderful night for both of them.

It wasn’t until Juston heard her ask what she was able to do to make him happy. “Well, first of all,” he said between kisses as his harder cock was pressing against her panties, “I think we’re both still over-dressed.” Juston moved his hands up her back and found the clasp to the strapless bra. Within a few seconds, it was already undone and he laid her down on her back as he slowly peeled it off, taking his time with exposing her lovely, perky breasts.

Juston sat up and started to move his hands onto her gorgeous breasts, feeling them, caressing them. He was smiling more as he felt his hands continue to play with them for a moment before moving them lower. He felt her smooth skin, her flat stomach as his hands started to reach the sides of her panties. As he looped his fingers around them, he pulled them down, again, taking his time to reveal her very bare pussy. “I think it’s pretty clear what you can do to make me happy,” he added as he finished pulling the panties off and tossed them to the side with the bra.

Once he spent a few moments looking at the lovely lady lying naked in front of him, he leaned over and gently grabbed her hands moving them to his boxers. “I want you to suck my cock before it fills you up,” he told her as he felt her hands pull his boxers down, exposing his member.