Chapter 12: Rules of Engagement

The five young women sat at an outside table at a nice restaurant in downtown Sarasota named Maurice’s: Edie, Kat, Amber, and their new friends Crystal and Melody. They were more upscale than the restaurant, and their looks and demeanor captivated the attention of everyone that walked by. Each of the girls had ordered a salad. There was some talk about the summer jobs that the latter two girls had taken: Crystal as a part-time waitress during the dinner shift at TGIFridays restaurant, and Melody as a clerk and stockgirl in Heaven – a woman’s clothing boutique.

After they were served, Melody introduced the main subject for discussion. “Thanks for meeting with us. We’ve done a lot of thinking and studying about becoming escorts. In our online research we came across the website for Sensations Escort Service, and we recognized the three of you. Well, we recognized Kat first because we’d met last semester in class, but then we realized at the party that you Edie and you Amber were also part of the business.

“We think we know what’s involved, and we’d like to work in the same business. I don’t know whether you’re hiring or how that would work, but we talked at the party when we figured out who you were and decided to approach you.”

Kat said, “You do know what an escort does and what the other names are for what we do?”

Crystal and Melody nodded.

Crystal quietly said, “Yes. Lots of sex, and we’d basically become high-end prostitutes or call girls.”

“The job is illegal. You could be arrested, get a police record, and possibly contract an STD if you weren’t careful. Part of the job is glamorous, and part isn’t. We’re in a clinic getting tested at least once a month. We are very guarded in who we do business with, being aware of possible sting operations, and we watch what we’re saying so we are never soliciting.”

“You could teach us?” Melody said eagerly. “We’re fast learners. We both have very high GPAs.”

Amber volunteered, “You need to ratchet up your sex appeal several levels. Being college girls helps, but you need a much higher level of sophistication about yourselves: your ability to carry on deep discussions, your awareness of what’s going on in the world as well as locally, how you dress, and how you speak – nothing is less of a put-off than carrying your college-speak into a date.”

Kat added, “On top of that you need to be ready for just about anything of a sexual nature, and I mean ANYTHING.” She laughed, “Every perversion man can think of will sooner or later present itself to you in this line of work. Think kinky. Think Fifty Shades of Grey on steroids. You have to be able to say ‘No,’ manage your client or clients, and not be afraid to run out the door and never look back.”

Edie said, “You will most likely need to lie to your families about what you do for work. The odds of meeting any guys that will be interested in long-term relationships with you are slim to none, although each of us seems to have found one.”

Crystal said, “But you make good money, right? We saw you three arrive in a little sports car.”

Kat laughed, “Oh, the money makes it all worthwhile, at least for me. Yeah, it’s typically one or two thousand a ‘date,’ and maybe four to six for a weekend away somewhere. Edie is about to leave on a five week ‘assignment’ where she’ll bring home around eighty-thousand and maybe more.”

“Holy fuck, sweet Jesus,” Melody muttered.

The girls talked more and more about some of the downsides and then about some of their offsetting experiences: the private jets, the nights sitting in a private box at the opera or ballet, the businessmen they met, rubbing elbows with people in Washington and elsewhere that ran the country and the economy, and on and on. Kat went into more detail about the sex she’d both enjoyed and put up with since they’d started. Amber talked about a couple of close calls they’d had with the law, but had fortunately deflected.

Crystal said, “I love it all, and I think we can contend with the downsides you mentioned. I admit to never having done girl-on-girl sex though, but the idea doesn’t repel me in the least.” She glanced at Melody who was nodding in agreement and added, “Maybe we should fix that this afternoon.”

Melody look surprised, but agreed, “Oh, that sounds like a nice idea.”

Crystal looked at each of the established women, “How can we start?”

Amber said to Kat and Edie, “You know when I leave, there’ll be some customers that need servicing. I’m sure there will be time conflicts with your schedules. We could try them out.”

Kat said firmly, “I don’t want employees. I want associates and colleagues just the way we are with each other.”

Amber said, “If we get some photographs, we could add them to the website and see whether they generate any calls on their own too. I recall there was a lot of interest in college girls by some of the businessmen we met.”

Kat turned to the pair of newbies, “I’d say you’re in. I guess the right term is that we’ll sponsor you and co-market with you. Occasionally, it sounds like we will recommend you to one of our marks, especially when we have a conflict of some kind. This’ll be a trial to start with, and if we’re compatible and this is working we’ll continue. Of course, you can opt out at any time if you change your minds.”

Crystal and Melody jumped up and down in their chairs. “Oh, yes. Yes. We’re so excited. This is a turning point in our lives for the better.”

“Just remember we warned you about all the downsides we could think of. They’re very real.” Kat reached over a shook Melody’s hand and then Crystal’s.

The discussion shifted again to more practical matters. Edie and Amber detailed the need for about thirty or forty photographs of each girl, ranging from pin-up poses to very college-like and even reflective poses. Kat gave each girl a list of mandatory clothing they each needed, even talking about which thrift shops they could visit to find some of the items at this stage in their work when they had no money.

Edie tutored them a little on first night jitters and how to get over them. As it turned out neither Crystal nor Melody was very experienced sexually.

Kat got Brad on the phone a few days later as they planned their weekend. “Hey, Stud. Want some new pussy?” She briefly told him about Crystal and Melody.

Brad laughed, “Hell, yes. I’m always up for some F-F-M action. If either one is as naïve as you say, we could have some fun introducing them to the ways of the world.”

Kat chuckled, “I’ll set something up. Mind spending the extra money?”

“Not a bit. Sounds like fun. I’ll arrive Friday evening and we can do dinner together. You map it out for us and tell me what role you want me to play.”

Kat didn’t tell Crystal much, only that she had a request from a regular mark for two girls for the evening. They would be meeting at the Westin Hotel, dine, maybe dance, and then have some other fun. She told her that she’d make some money, but not an outrageous amount. Crystal explained as how she knew this was a trial and she’d do whatever was required of her and take whatever she got. Kat talked about a large purse and a RON or Remain Over Night kit, and a few other practical items to avoid embarrassment the day after. In this case, the ‘date’ was from Friday night to Sunday dinner when Brad would have to fly home to Boston.

Kat met Crystal at the hotel. She greeted the pretty blonde haired girl in the posh lobby as though she was seeing a long-lost friend for the first time in years, even holding and hugging her new friend as they did polite female kisses. Kat checked her over.

Crystal was dressed very nicely in four-inch open toed heels, a full knee-length skirt, a wide belt around her svelte middle, and a silk blouse that allowed her lacy brassiere to be seen through the semi-transparent fabric. She carried a large shoulder bag as a purse as she’d been instructed.

As Kat looked Crystal over, she could tell she’d conditioned her long hair so that it positively glowed, plus she’d gotten a manicure and pedicure with glossy and sexy red polish. She wore a pearl necklace, several rings on her fingers and beautiful broach.

Crystal looked as nervous as a long-tailed cat in a room full of rocking chairs. If anybody had come up behind her and said ‘Boo’ she’d have jumped right up to the tall ceiling and held on.

Kat tried to calm her new friend, “Crystal, calm down. You’re twitching. The idea is to help calm and be a restorative force for your ‘date,’ not the other way around. If you’re this nervous, you won’t have good orgasms, and that’s something I know Brad likes to be sure you have. He’s a nice guy. He’s not going to eat you up and spit you out, well, unless you want him to.” She laughed hoping the humor might be contagious.

Kat suddenly added, “If you’re having second thoughts about this line of work, now is the time to scoot. No harm. No foul.”

Crystal said in a nervous voice, ‘Oh, no, it’s not that at all. I’m committed. I’m as nervous that you’re here as I am that Brad will show up any minute. I’m sure he’s nice and all that. I’m sure I’ll calm down after we start to eat or something. I’m...”

“Ladies,” Brad’s voice said from besides them, “what a pleasure to see you again, Kat; and I guess this is the wonderful Crystal that you raved to me about.” He kissed Kat and gave a polite hug to Crystal, complementing her on her dress.

The three had a leisurely meal, and Brad did just what Kat had asked him to do; he flirted incessantly with Crystal and she gradually relaxed and lost the worst case of jitters that Kat had seen that year. She participated in some of the teasing, but generally tried to make the ‘date’ about Crystal and Brad. She knew she’d get payback later and have some sexy fun in the process.

Dinner took about ninety minutes. Brad then suggested we go up to the rooftop lounge to dance a little. Kat had clued Crystal into the possibility, and she responded just as Kat had prompted that she just loved to dance. There was a nice jazz trio playing some very danceable music. Kat gave Crystal a nudge and she joined Brad on the dance floor while she ordered some drinks. Kat saw the two of them cuddle right up together as he put the make on her.

Oddly, Kat didn’t feel jealous or worried. Crystal was younger and very pretty, but Kat trusted her own looks, demeanor, personality, and intellect. Besides, she decided that all that stuff didn’t begin to equal the real thing that Brad and her had together – ‘chemistry.’

Just as the drinks arrived, so did a not-so-secret admirer from the bar area. “Excuse me, but you seem to be the odd man out in your trio. Would you care to dance? I promise I don’t have two left feet.”

The man asking Kat was in his late forties, had a smile that would make his orthodontist proud, and looked lean and tan as though he’d spent considerable time outside.

Kat smiled, “I would like that, and you name is?”

“Mark Hanley, at your service.”

“Well, I’m Kat, and I’m a marketing consultant that lives in town over near the university.”

Mark took her hand and escorted the sharply dressed escort to the dance floor. Kat thought they made quiet a handsome couple. As they assumed the more formal dance position he said, “And I’m the tennis pro at the Bath and Racquet Club. I was here with visiting friends for dinner, but they retired early and I thought I would see what the lounge in this place was like for future reference. As you may know, this place is relatively new.”

After a slow dance and a fast dance, Mark led Kat back to my table. She extended an invitation for him to join them since he was alone. Kat was being adaptive in what was going on, and thought this might be a good way for Crystal to see how to deal with an unusual but very pleasant situation.

Crystal and Brad returned to the table too, and Kat made introductions to her new friend. She watched Crystal and while she obviously had some questions she wanted to ask her about the protocol of having someone else suddenly join them unexpectedly, she just played along and followed Kat’s lead.

Kat hinted to Brad in an aside that she wanted to dance with him, and soon they were on the dance floor. She watched as Mark asked Crystal to dance, and she graciously accepted and they moved to dance a little away from them among a dozen other couples.

Brad asked, “How well do you know Mark?”

“Not well at all. We just met. A few words between us, that’s all. Never saw him before. As you heard him repeat to all of us, he’s the tennis pro at the local upscale bath and tennis resort here in town. Other than some niceties that’s all I know.”

“Is he trying to get lucky?” Brad teased. “If he is, I support his goal.”

“Maybe, but I’m more interested in facilitating you and Crystal so that she gets some ‘on the bed’ experience in her new career from a skilled lover who’ll turn her every which way but loose. I have some designs on her pussy too, but only after you’ve filled it with man juice.”

“Well, if you want to seduce your new friend, I don’t mind. I like the guy. We could do a foursome in my suite. You already know I like group sex.”

“I’m not too sure, yet. Like me, he’s local. Almost all of our clients at Sensations have been from out of town.”

“Think about it. It’s a big city.”

“What if he pursues Crystal or me for dates? He mentioned he was divorced.”

“Up to you. Test whether he believes that ‘no’ means ‘no’.”

Kat pondered how to do that, deciding that the best way might be a less subtle test.

A few dances later Brad and Kat sat down; Mark and Crystal quickly joined them. Kat could tell that Crystal had a few questions, so she suggested a trip to the ladies room. The two girls excused themselves.

As soon as they were in the restroom, Crystal said, “What’s with Mark Hanley? What should I do? We do? He’s very nice but he’s not paying like Brad is? What’s protocol here?” She was nervous all over again.

Kat laughed as she pulled out her iPhone, “Well, first we make sure Mr. Hanley is who he says he is. A few seconds later, She showed Crystal the screen on her phone. “Yes, Mark is the tennis pro at the Bath and Racquet Club, so at least we know he’s not with the vice squad or something similar. A quick read of his bio and I see that he’s accomplished many laudatory deeds in tennis. He’s played at Queens, Forest Hills, and Wimbledon too for several years earlier in his career, and has a long list of awards and places he’s won various matches. Since he hasn’t mentioned any of that, I would say that makes him somewhat modest.”

Crystal ventured, “Well, I kind of like the man. He’s a great dancer – a good lead, but I think he’s older than my father.”

Kat laughed, “He’s older than my father too, and in this line of work you’ll find that almost all of your customers will be older men. If you want Joe College you’ve decided on the wrong profession. They want to get laid after a piece of pizza and a beer.”

Crystal allowed, “If I liked Joe College I wouldn’t be here; as they say, ‘been there, done that, got the t-shirt, and sold the movie rights’. I got a little sick of their sophomoric attempts at seduction and then their lack of knowledge or willingness about how to please a girl.”

“Shall we see if Mr. Mark Hanley knows how to please a girl? I suspect he’s quite the player, and I don’t mean just tennis.” She looked into Crystal’s eyes and posed, “Are you willing to get fucked by two different men tonight, because I am?”

Crystal suddenly looked a little shocked. “Errr, yeah,” she stammered. “When you say it that way, it took me by surprise. Yes. I like Brad and Mark. Not only that, but ... well, they’ve both made me wet between my legs and hornier than I’ve been in ages. Part of it is knowing that this is my first escort job. I’ve never worried about so much stuff before a date before: perfect dress, perfect shoes, perfect lingerie, perfect makeup, hair style, nails, and then all the right stuff in my shoulder bag for just-in-case situations. I’ve never done this level of preparation for a date, even my graduation prom.”

Back at the table, Kat asked Mark, “What’s you love life been like since you got divorced?”

Mark shook his head, “I’ve had a couple of long-term relationships, but when I was on the circuit I was traveling so much it just didn’t seem wise. To tell the truth, I’ve always wanted to play the field and not have a pretty lady sitting in some town like this one biding her time until I got back from a two-month tour. I’d have been a pretty poor dad too not being around that much.”