"The High School Hookers Club" (open, sort of)

[CutiePie1997]

"This woman won't be looking for commitment," Pamela told him confidently. "To be honest, she needs arm candy probably as much as you do. If you think you could commit to accompanying her to an occasional office party at her place of employment..."

They chatted a bit more about the woman being contemplated as Tyler's fake girlfriend, reassuring one another that it would be very casual. Pamela pulled out her cell phone, tapped and swiped, then turned it toward the man who had rocked her world the previous evening...

"Her name is Charlotte, but I call her Charlie," Pamela continued. "She used to be a lingerie model but is now a fashion designer. That's one of her dresses. I'll text her about what we've discussed. I'm sure she'll be tickled pink to meet you."

They finished their coffees, shared their last thoughts on the wonderful night they'd had together, and -- after Pamela told Tyler she had a busy weekend ahead of her, without giving him details -- they parted ways.



Monday after last bell:

Pamela waited in the hall outside Tyler's classroom until the last of the students seemed to have departed. She made her way through the door, just in time to nearly collide with Rose Hanford...

Pamela donned a surprised expression, saying politely, "Oh! Sorry, Rose. How are you?"

The other teen's expression was one of annoyance. She glared at Pamela for a moment, then only said as she pushed by, "Excuse you."

Pamela watched the blonde strut quickly down the hallway, checking out her beautiful figure. She smiled as she thought I could make a fortune off you. She turned back into the room to find Tyler at his desk rounding up the weekend's assignments. She waited until she caught his eye, then entered slowly, letting her hips sway a bit more than naturally as she greeted, "Hey, Teach."

Pamela waited until she was at his desk to casually look back to the door for eavesdroppers, then tell him in almost a whisper, "I very much enjoyed Friday night ... and ... I can't wait to do it again."

After he'd made his reply, she donned a slightly disappointed expression telling Tyler, "Unfortunately, it might be a while. I've got a pretty full schedule the next week or so."

Again she paused, then continued, "Good news for you, however. I called Charlie, and she would like to meet you ... dinner and drinks maybe ... at least drinks. I sent her a phone pic of you from last year's yearbook, and I could--"

She glanced again at the door before looking back to him and saying even more softly, "And I could hear her pussy begin leaking."

Pamela laughed loudly, knowing how inappropriate and nasty the comment had been. She told him, "More good news. I've got a client who wants a threesome." She smiled broadly, then laughed again. "No, not with you and a girl, but with two girls. I've got the girls already, but ... well ... there's a bit of a problem. One's a lesbian whose hasn't been with a man since she first lost her virginity ... and the other's ... I can't believe I'm saying this ... the other one's a virgin, at least with guys. But ... they both want to do this. It's good money, and they need it. But I can't very well put them with a man whose used to professionals, what with them being what they are and what they aren't ... so ... I was thinking maybe you might want to do a little teaching."

As she'd been talking, Pamela had pulled out her phone again, tapped and swiped, and turned it to him. "I think you know Julie and Kimberly..."

Pamela knew Tyler should. The two Baker cousins had just left his classroom five minutes earlier. She told him quickly, "No, they don't know you are part of all this. They only know that I know a guy who knows a guy who likes young'uns ... and might like to spend some time with them. If they ask me later if I knew it was you..."

She feigned an overly shocked expression, slapping her hands to her cheeks as her mouth and eyes opened wide, then returned to a devilish smirk, saying, "I'll play dumb."

She pocketed her phone, gave him the details on how they had appointments with her gynecologist for testing and pregnancy prevention discussions on Wednesday. "They'll be ready by this weekend. So ... interested?"

 

[XXXHacker]

As Pamela came into his classroom clearly wanting to talk business, he was annoyed that Pamela was already risking him being discovered by talking to him in class. "Pamela, I had a great time, too, but I would very much appreciate it if we didn't discuss this at school. You don't know who could listen in on us."

When he heard about Charli, he was a little relieved, as he at least soon could have an alibi. While he did find Charli attractive, he had struggled with the thought of effectively having a fuck buddy, as if she would mind that he preferred women younger than her, but when Pamela stroked his ego, he figured the least he could do was entertain her for one date and see how it went.

But before he could respond, Pamela was already talking about the Baker twins. He was concerned about more of his student fucking their teacher. He looked at his watch, and said, "I'm late for a meeting with the head coach, going to give him my resignation. Talk to me on Wednesday after these tests had been done." Tyler started to walk out of the room, but suddenly stopped and turned around. "OFF Campus."

Tyler then proceeded to meet with the head football coach and offer his resignation as the Offensive alive coach. The head coach accepted, admitting that with his son joining the staff, it was going to be awkward between the son and Tyler, so this was probably for the best. The head coach did say he was happy with Tyler's work and would give a recommendation if Tyler decided to leave Harrison High. Tyler told him he hadn't made any decisions yet, and was going to sit next year out, finish the school year at Harrison, and decide what he wanted to do after he had time to reflect.

 

[CutiePie1997]

Monday:

"OFF Campus."

Pamela shrugged and said as Tyler turned to leave, "Fine ... off campus."

He was correct, of course. The classroom was probably not the right setting for discussing the future of their blossoming prostitution ring...



Thursday:

And blossoming it was!

Pamela wouldn't be able to get together with Tyler on Wednesday, explaining that she'd see him soon and -- if it still suited him -- the Baker Cousins would as well. She found enough time to drop by his class room on Friday and give him a note with his date plans for that night with Charli.

By then, Pamel's business was already on its way. The Baker Cousins had passed their physicals and arranged for their birth control; Lilly had had a second date with a second John; and -- even more surprising -- Pamela had found yet another girl who was ready to make some money with her body. Only this one was anything but a seasoned amateur looking to go professional.

Maria Sanchez was like no other girl Pamela had ever known, and for so very many reasons. The 19 year old had already received her High School diploma, yet -- with an Athletics Department Scholarship -- had remained at Harrison High for another year to complete the part time College Prep Program. Maria was or had once been a member of the school's cheer squad, dance team, and drama department, the latter of which, among other things, had resulted in her singing some pretty saucy songs in some very saucy outfits at the annual talent show. The girl had been causing the male student body -- bodies! -- to get all hot and bothered for years ... and yet she was still a virgin!

But, that was all about to change.

Lilly came to Pamela on Tuesday with some incredible news and a great idea. The latter teen hadn't been too hip on the idea at the time, yet here she was now with Lilly and Maria. She sat across from the beautiful Latina in a local coffee shop and, after nearly half an hour of casual chit chat highlighted by nervous energy, Pamela asked point blank, "So, Lilly tells me you want to auction off your virginity?"

Maria blushed and looked down, obviously embarrassed before chuckling nervously and answering in a soft tone, "Makes sense, I think."

Pamela asked with all seriousness, "Why does it make sense?"

"The boys at Harrison ... and some of the boys from my sister's college, too, have been trying for years to get me out of my clothes," she answered, continuing, "And some of them have spent a lot of money trying. Dates in fancy restaurants, or what they thought were fancy. Concerts, jewelry. One guy from a Frat invited me to Ensenada for the weekend. His folks have a time share there."

"All you had to do was sleep with him," Pamela said with a matter of fact tone. And after Maria nodded, Pamela asked, "Was this before or after he realized you were a virgin?"

"After," she said, smiling broadly and blushing again. She explained that they were getting too comfortable in his car when she told him she couldn't and hadn't, and over the next couple of dates and dozens of calls and texts, he'd asked her to go to Baja. She finished explaining his claim with a doubtful tone, "Where he would teach me the ways of love."

The other two girls laughed along with Maria. Although Pamela and Lilly had each lost their virginity to men who had known what they were doing with a woman, it wasn't always true for others of their gender. Oh, the stories Pamela had heard of first times. They just made her cringe, imagining all of that awkward petting and slopping kissing and pained intrusions.

"Why come to me?" Pamela asked. She already knew the answer -- Pamela had discussed Lilly's earlier conversation with the beautiful darker skinned girl -- but she wanted to hear Maria say it aloud. "What do you think I can do for you?"

"Lilly says you might know a way to do this without me having to put my name and face all over the internet," Maria answered, the concern obvious in her voice. "And ... how do-- how does the bidding work? I mean, it's not like I can parade around at the Livestock Auction down on Taylor Avenue while some guy does that fast talking, bid taking."

Pamela thought about it for a moment, then told Maria, "I can make this happen."

"Really?" Maria asked, her tone hopeful for the first time. "How?"

"Let me worry about that," the madam-to-be reassured her. "The only person who will know who you are is the person who places the highest bid."

"And what if he tells all of his buddies that--"

Pamela cut the girl off, contemplating her recent hiring of Muscle as she reassured Maria, "I have that covered. He's going to want to brag to his buddies ... and he will ... but, he won't know your name ... and you'll never see him after it's over. I promise you."

The three girls looked around between one another, each of their minds filling with the potential -- and excitement -- of this latest adventure. Pamela continued, "I have an OBGYN I want you to go see. I'll make an appointment."

They discussed health and safety for a moment, then after a long moment of awkward silence, Maria asked, "So ... is there anything I should do ... you know ... to prepare myself. Practice, I mean ... like with a--"

"No!" Pamela cut in, pointing a chastising finger at Maria just as she had with Lilly days earlier before that teen's date with John Hanford. "The highest bidder is buying innocence and naiveté ... and a hole he can't hardly get his cock into."

Maria laughed suddenly, shocked at the other 19 year old's crude statement. Even Lilly laughed, reassuring Maria that she was going to have to get used to Pamela's forwardness when it came to such issues. Pamela clarified, "If you go sticking toys where they don't belong ... he's gonna know, or think someone's beat him to you."

They discussed Maria's shaving routine, with Pamela telling her that that was permissible, then the Latina thanked the two and wandered away, looking back over her shoulder with an expression that was part gratitude, part embarrassment.

"How much do you think you can get for her?" Lilly asked, clarifying, "For popping her cherry, I mean."

"I don't know," Pamela asked honestly, rising to depart. "Most men pay for experience, so ... I have no idea ... at all. But ... I'm eager to find out."



Friday:

Charli was sitting in a small booth along the wall of a downtown hotel's lounge when she looked up to see Tyler entering. Her stomach turned over at the sight of the man, whose image on Pamela's phone hadn't done him justice. She tried not to ogle his form as he found her and headed her way ... but that was simply impossible. The man was simply delicious, and while they were here to meet for drinks and familiarity, Charli had decided by the time he got to the table that if his personality was half as nice as his bod', she was getting naked, sweaty, and loud with Tyler before the sun came up.

(OOC: This portion of the story -- the date between Charli and Tyler -- continues in a new thread called "Uck-fay Uddy-bays". If you don't know Pig Latin, I'm sure you'll figure the title out.)

 

[XXXHacker]

Monday afternoon:

Tyler sat at a table inside a coffee shop near Pamela's estate. He had received a text from Pamela on Saturday, but he didn't get a chance to read it until Sunday morning, after Charli had spent the whole weekend 'getting to know him.' He responded to Pamela's text as Charli slept soundly in the early morning next to him, wearing only one of his old football jerseys, and his cum pouring out of her pussy from all of the weekend's activities.

As Tyler sat there waiting for Pamela, he was thinking back to Pamela's offer. He had realized that this was the first time he thought about a woman other than Charli all weekend. But as Pamela walked in, he couldn't hide his shit-eating grin on his face and said, "Well, you were right."

 

[CutiePie1997]

"Then, you had a good time," Pamela asked as she sat, sharing the same devilish smile on Tyler's face. Honestly, she had had her doubts. Older people like Tyler and Charli with sexual histories like theirs could sometimes be hard to match up with others with similarly active pasts. The expectations were simply too high at times. Pamela had thought of the two often over the weekend, wondering how the blind date had turned out, only to finally receive a text from Charli last night that simply said Thank you my friend. She gestured to the barista, who nodded back and began on the teen's regular coffee drink. Then, with feigned confidence, Pamela said to Tyler, "I knew you'd like her."

She listened to Tyler report what he was willing to share, then asked, "So, the providing one another with arm candy thing...? That's settled, then?"

They chatted a bit, then -- after the barista had delivered Pamela's drink -- turned to business.

"The Baker Cousins..." Pamela began. "There's gonna be a bit of a delay there. Couple of weeks at least."

She went on to explain -- but only vaguely -- that the choice of pregnancy prevention for the two teens was still being settled. She smiled devilishly, looked about herself for eavesdroppers, then said quietly, "It's gonna be shocking enough taking on your big cock, without fearing getting knocked up."

Pamela explained that she preferred not to rely on condoms alone for pregnancy prevention. Then, a thought came to her. "Of course ... if you thought you could get naked with the Cousins with out fucking them..."

She lifted her coffee to her lips, looking over the rim as she waited for Tyler's response.

 

[XXXHacker]

As the Baker cousins came up, Tyler was once again reminded why Pamela wanted to talk, about her prostitution ring with his students. Listening to what she had to say about pregnancy prevention, he chimed in. "Well, I'm going to be just as concerned. I think Charli will be able to help as my alibi, but no alibi can handle a paternity test showing you're the father of the baby growing in one of your students." When she mentioned getting naked without fucking them, he replied, "What are you thinking?"

 

[CutiePie1997]

Pamela agreed with Tyler about the potential pregnancy threat, reassuring him that she would never put him or the girls in a situation where they weren't adequately protected. Oh sure, a male cumming inside a female always carried the potential for an uh oh situation. But Pamela was a safety first kind of girl, and she wasn't going to let one of her girls, their protector, or their madam get into such a situation without ample precautions ... and options.

"What are you thinking?"

...Tyler asked when she wondered about whether he could spend an evening naked with two sexy teenagers without putting his dick into one of their pussies.

"Remember back in your high school days," she began in a reminiscent tone, "when you were just finally getting a new girl friend out of her clothes for the first time ... but, because it was the first time for one of you ... maybe both of you ... she wasn't on the pill and you hadn't thought to bring a condom? And as much as you wanted ... even begged her to take a chance, because every one knows you can't get pregnant the first time, right...?"

Pamela laughed loudly, wondering how in this day and age young lovers could still believe so many things that were so untrue about sex. A pair of patrons passed by the booth, making Pamela pause before continuing, "So, here you are, naked together and burnin' up with lust ... and--" She hesitated, checked for eavesdroppers, then continued in almost a whisper, "And you don't dare fuck her. So ... what do you do?"

She sat back, lifted her coffee mug to her lips, then said, "That's what I'm thinking." She sipped, then continued, "Do what you can. Do what you want. Do what ever they want. Just don't fuck'em."

A laugh escaped from a nearby booth, causing Pamela to lean out and look for the person from which it had come. She herself chuckled at seeing the unexpected but familiar face. She turned back to Tyler and -- gesturing him to leave -- whispered, "You might want to split."

Pamela picked up her mug, stood, and curled around to sit at the booth behind her, still facing Tyler's direction. She eyed him for a moment, then said to her new booth mate, "What're you doing here?"

 

[XXXHacker]

Tyler was listening to everything he heard Pamela was saying. Putting together what she was asking, he was about to make the point that what she was asking was impossible. He was not a boy, he's a man, there's no easing a man into sex and holding off because of not being on birth control. If you get him going, his cock will end up in a pussy, there will be no denying him. Either find him a pussy he can stuff his cock into, or wait until the Baker cousins are able to take his cock in their near virgin holes.

But he never got a chance to say that because of Pamela's attention being led to the other person in the booth next to them. Tyler had already paid for his coffee, so when Pamela shifted her attention, he got up and left, not looking back to see who it was, for fear of getting recognized.

 

[CutiePie1997]

For those of you following our story, my post above continues at the following thread, "Blondes Have More Fun", which I will write with CarnivalBarker until a male "John" begins writing there. Please, subscribe and enjoy.

 

[CutiePie1997]

Friday evening:

It had been an interesting couple of weeks for Pamela. In less than two weeks actually, she'd learned she was going to lose her home, then made a deal to keep it that would result in her branching out from being a prostitute to being a madam; she'd found a new lover in one Tyler Boggs, Harrison High teacher and coach; she'd then subsequently set up said teacher and coach with a friend of hers, Charli, with whom Tyler had had one helluva weekend; she'd aided her friend Lilly in having her first paid "date" with a John -- coincidentally actually named John -- and then hired the girl on as her first contract employee (aka hooker); she'd attracted yet another school mate, Chelsea, into the business, with Chelsea's first day of work planned for tomorrow's barbeque at the Malibu beach house; and -- right now at this very moment -- she was in the hotel lounge of yet another elegant downtown hotel, sitting across from THSHC'S latest potential client, one Jason Hawthorne, who had been referred to Pamela by one of her long time regulars, Charles Thompson.

They'd been chit chatting about this and that for more than thirty minutes, the typical fare for acceptance as a client, before -- with a low volume and playful tone -- Pamela got graphic with, "Chuck tells me you have an interest in being with two girls ... together ... a little menage a toi."

 

[Lustful_Intentions]

By the time Pamela reached her provocative question, Jason was already at ease with her, and not terribly taken aback by the query. They'd been chatting away at a high-top two-seater at the far end of the room for nearly 30 minutes, with Pamela deftly moving from small talk about what Jason did (not that the girl didn't already know) with subtle questions designed to ensure his discretion.

He nearly bristled at those particular questions. As the youngest member of a family that, for three generations had been helping some of the town's wealthiest buy and sell real estate in and around the area, his family knew very deep and interesting things about many of the town's most powerful people. And when Pamela described some of the types of girls in her employ, he knew there was a non-zero chance that some of the girls were members of the very families Jason's had represented in real estate transactions for over 50 years.

Still, he admired the young girl's pluck, much as Mr. Thompson, the town Treasurer and a big booster of the Harrison football program, said would be the case. The older man had only mentioned Pamela to him after Jason delivered some final closing documents for the Treasurer's new beach condo and remarked how he expected that Mr. Thompson would really enjoy the views-a conversation that would devolve into discussing the best places to ogle nubile coeds at the shore.

And so, to Pamela's question, Jason turned his green-eyed gaze to the ground for a minute, fingers toying with the stirrer in his drink.

"Well, yes, Pamela, I admit, I was curious if...two girls was a thing you could provide." Before she could respond further, he gave a small wave of his hand "And yes, I know-it'll cost me. I rather wouldn't expect a two for one, at least, not one of the caliber of girl I'd want if I'm going to spend the money. Certainly, it would be my preference that the girls are previously acquainted, if for no other reason than their own comfort. If that helps them," He looked up now, locking a green eyed gaze with her, "Put on a bit of a show, then all the better. But, not a requirement. I trust that you know how to handle something like this."

 

[CutiePie1997]

Pamela did have the two girls for the job, of course, but it was only because of a total fluke in Pamela's recruitment efforts. After Lilly's lack first attempt at prostitution with one John Hanford -- sexually satisfying but professionally lacking -- Pamela had set the 18 year old wanna-be hooker with a couple of her regulars, who -- with Pamela's additional guidance -- had trained her in the difference between being a girl friend and an escort. Ironically, the result was what Pamela called the Girlfriend Experience, simply defined as making the client feel as though they are with an actual girl friend who cares only for their sexual needs, not for their wallet.

Lilly's growth over just those four dates had been spectacular. But the trust test was going to be sending her back for a second date with Mister Hanford, a Malibu beach neighbor of Pamela and the father of Rose, a Harrison High classmate of both teen escorts. If John signed off on Lilly's transformation, then Pamela knew the girl would become a big money maker for her.

So how did Lilly tie into her current sit down, meet and greet with the man sitting before her? It had been Lilly who had recruited the Baker Cousins into The High School Hookers Club, much to Pamela's chagrin. The two blood relatives -- who had been one another's lovers since long before even a liberal society would have approved -- had decided that it was time to give men a try. Lilly had delved into a long conversation with the cousins -- that pushed every so slowly toward convincing the girls that they should try to get something more than just a new experience and, with luck, some new pleasures.

"What do you mean?" the 18 year old Kimberly had asked.

"Money," Lilly had said without hesitation. Then as the two girls just stared in surprise, she added, "Most men would pay a lot of money to be with two sexy young women like yourselves ... add to that that your not just two girls but two lesbians!"

The reaction to Lilly letting it be known that she knew the two cousins were one another's lovers was greatly different. Julie looked angry and offended, an outgrowth of her belief that her involvement with her own relative had been a secret, even to Lilly who was Kimberly's best friend. Kimberly, however, blushed a fiery red and glanced away, embarrassed. She'd told Lilly what she and her cousin had been doing for years during a night of passion between Kimberly and Lilly, something that was still unknown to Julie, who had always been very jealous of her cousin's friendships with other females.

Lilly had continued on without regard to the cousins' reactions, "Guys drool over the idea of being with lesbians. I'm serious! I don't have to tell you that. How many guys at Harrison had tried to get one or the other of you together with another girl before? I know for a fact that Big Bob Templeton tried to get the two of you to go to his hotel room after last year's prom."

The three of them had discussed the concept of charging a guy for fucking them, with the cousins not yet understanding that Lilly herself had recently had her first paid appointment with a john named John. Finally, when the very persuasive Lilly got them onboard, she hooked them up -- to their continuing surprise -- with Pamela Dryer, who then arranged testing and birth control for them. And now, here was Pamela arranging for their inaugural appointment.

Jason continued his answer to Pamela, adding the detail of...

"Certainly, it would be my preference that the girls are previously acquainted, if for no other reason than their own comfort. If that helps them ... Put on a bit of a show, then all the better. But, not a requirement. I trust that you know how to handle something like this."

Pamela smiled a bit, happy with the way this was unfolding. So far, her new business venture had gone very well, far better than expectations. She told Jason, "The two young ladies I have in mind are perfect. Actually ... they're better than perfect."

She glanced around to ensure no eavesdroppers, then continued, "They are lesbians..." She explained that one of them had given her virginity to a boy long ago yet had not been with a man since; and that the other had never been with a male and, in fact, had only been with one other female beyond the long relationship she'd had with her current partner, "Her cousin."

She saw the effect of the word cousin on Jason, and continued, "The two girls I have in mind for you are biological cousins. Is that a problem? The incest angle, I mean?"


(OOC: This interaction between Pamela and Jason -- and eventually Jason and the Baker Cousins -- continues here with a repeat of this post as the start of a new thread: http://forum.literotica.com/showthread.php?t=1381588)