Adelle's Girls: Cleo

I'm trying something a little different here with a series of loosely connected stories focusing on different interconnected characters. I hope you guys enjoy, and remember comments and votes are appreciated.

"Yes sir, Dianne will be there at nine pm sharp," Cleo said, marking the appointment in her calendar.

"Fantastic. I look forward to it," the man on the other end said, a smile in his voice. "Thank you so much dear."

"You're welcome, sir. We hope you enjoy your night," Cleo said, hanging up. Checking the schedule for the night, she could see it was shaping up to be pretty busy. Fridays were generally busy, but this was exceptional even for them. "Busy night," she said to Adelle.

"Oh?" the older woman asked, looking up from her own bookkeeping.

"Uh-hm," Cleo said, pulling up the main calendar page. "Eleven dates, plus three doubles and that party at Verve... Yeah, I think we actually have everyone out tonight," Cleo said, double checking just to be sure. "That's a first for me."

"It's probably all the snow," the older woman replied in her clipped British accent. "If you're forced to stay in, might as well stay in fucking, hm?" Cleo blushed and laughed, and Adelle allowed a small smile at the younger girl's embarrassment. "I remember during that big blizzard two years ago, as soon as the weather reports started coming in we were booked solid."

"Snow's good for business then," Cleo noted, returning to her business mode. Adelle watched the younger girl closely for a moment, remembering hiring the girl four months previous.

~~~~~~~~~~~~~~~

"So, Ms. Miller, may I call you Cleo?" Adelle had asked, hoping to put the girl at ease.

"Please do," Cleo said, pushing her glasses up on her nose.

"So Erica has told you about our business here," Adelle stated simply. "What do you think?"

"Well, she didn't tell me at first, but I had sort of figured it out," Cleo explained.

"Really?" Adelle asked, surprised. "How do you know Erica, exactly?"

"I've been rooming with her for almost six months now, but before that I was a friend of a friend. I was looking to move closer to work, and she had an open room, so... It's been working pretty well."

"And how did you figure out that Erica was a call girl?" Adelle asked, amused when the younger girl blushed. Imagine if I had used the word whore, Adelle thought.

"Well... Her schedule was odd, and although she never talked or complained about work, she always seemed to have money. And she would talk about 'dates,' but I knew she didn't have a boyfriend. And the way she would dress for these dates was sometimes a little, well, whorish. So a couple weeks ago I just asked her, and she admitted it."

"Were you disgusted? Shocked? Titillated?"

"Maybe at first, but... I mean, she's never gotten hurt or anything, and she seemed to enjoy the dates, most times. Once we started talking about it, she made it seem a little glamorous, actually."

That'll pass, Adelle thought. "Glamorous how?"

"Oh, I don't know... Dashing men paying thousands of dollars for her companionship, y'know... I could see it was a bit of an ego boost for her, for the girl," Cleo explained. "I mean, I don't think it's for me, but I don't look down on her or anything for it. I mean, she's getting her master's degree, I'm not going to judge her on how she's paying for it."

"I see," Adelle said, appraising the young woman. She was quite pretty, even if she didn't know how to show it off. Long dark hair, pulled back into a simple ponytail, her pale skin unadorned with make up. Her delicate features, coupled with her glasses, gave her the look of a librarian, and her drab clothing did little to indicate at her body. Luckily I'm not hiring her to work with clients. "What did Erica tell you about the job?"

"Well, she said that you needed an assistant, someone to answer the phone, book the dates, keep everything straight. And, I mean, that's pretty much what I do now, so she thought I could..."

"If that's what you do now, why change? Whatever your current job's shortcomings, it's still legal," Adelle countered.

Cleo shrugged. "My current job is a deader than dead dead end. My boss is an ungrateful, foolish, demanding pig, and I'm sick of watching his back and covering for him. And, well..." Cleo foundered, not wanting to look foolish.

"What?" Adelle asked, leaning closer.

"I thought... I thought it would be a bit of an adventure. Exciting," Cleo said quietly, looking down. "I know it's stupid, I'd only be answering phones, but..."

"It's alright," Adelle said, placing a hand on the younger woman's knee. She liked this young woman, her resume more than qualified her, and Erica's recommendation weighed heavily in her favor. "The job's yours if you want it, but you should know: I can be a bit of a demanding bitch myself." Adelle quoted a figure that made Cleo's eyes widen, and with a handshake the job was hers.

~~~~~~~~~~~~~~~~~~~

Cleo snatched up the phone on the first ring. She hoped it wasn't another client, as she'd already had to turn down two for want of any available girls. "Adelle's, how may I help you?"

"Cleo? Oh thank fuck. It's Sheila."

"Hi... What's wrong? You sound like death."

"I don't know, but I'm definitely sick... I've got a hundred and two fever and I'm shitting a goddamn fountain," Sheila groaned.

"Sheila, Christ, that's disgusting."

"I'm sorry, I'm just a fuckin' mess. Is Adelle there? I was hoping I'd get better before my date, but I'm just getting worse, ugh..."

"Adelle's right here," Cleo said as Adelle returned from the front room. "It's Sheila, she sounds really sick."

"Oh hell," Adelle said, taking the phone. "Sheila? How are you feeling... That good. Sheila, dear, is there any chance that you'll be able to rally for tonight, because I don't know if we even have anyone in reserve... Ugh, lovely imagery dear, thank you." Adelle quickly checked the night's bookings, flagging Sheila's date and reading the relevant information. "Hm. Well we'll see what we can do here. Hm? No, no of course not. Stay warm, drink lots of fluids, and for god's sake never tell me about the state of your bowels ever again. Yes dear, please feel better. Bye." Adelle hung up.

"Well?" Cleo asked, looking at the date's details. Mr. Dunn had booked Sheila for the whole night three weeks ago, so she knew Adelle would be loathe to cancel it.

"Well I think we need to try and find someone to fill in for Sheila, clearly. And we have, oh, only two hours to do it." Cleo was worried that Adelle would say that.

"Adelle... We're already using some of our back-up girls as it is. I mean, I could call Danielle, but-"

"I told you to burn that slut's file," Adelle said bluntly. Danielle had broken a cardinal rule of Adelle's: she tried to snake clients and go independent. All she had managed to do was get sacked and lose the access she was hoping to use. Adelle was a great boss, but Cleo quickly learned that you didn't want to cross her.

Adelle looked closely at that calendar pages, saw that Cleo was right: They were already stretched to the breaking point, and she just plain didn't have any other girls to send. As she turned to tell Cleo to call Mr. Dunn, she considered the young lady again. Cleo had come a long way in the four months since she started working for Adelle. At Adelle's gentle urging, Cleo had started dressing better and doing her hair a little differently. Her hair was now in a stylish French braid, accenting her long neck and delicate features. Her clothing no longer hid her body, but took advantage of it, displaying her slim figure to excellent effect. Well, Adelle thought, it's worth a shot.

"Cleo... Perhaps..."

Cleo glanced up and saw the look on her boss's face and quickly deduced her thoughts. "No. No. No way. No. Absolutely out of the question!"

"Dear, you know I wouldn't ask if it wasn't an emergency, but-"

"But nothing!" Cleo said, flustered. "I'm not one of your girls, Adelle. You'll just have to call Mr. Dunn and cancel the date! I won't do it. I won't."

Adelle's eyes narrowed. She knew the young woman who called what Erica did "glamorous" would have at least some curiosity about it. She decided a different tack was needed.

"Mr. Dunn is a long time client, and I would hate to disappoint him so," she began, taking a seat at her desk and pulling up his client records. "He travels a great deal for business, but he finds himself in New York for a few days each month. He stays at the Waldorf and has a date with us whenever he's in town. I understand that he is quite generous, both in bed and out of it."

Cleo glared at her employer. She knew what Adelle was doing. "Oh really?"

"Quite. His desires are rather tame, compared to some of our other clients. But while tame, they are substantial. I understand he's quite the charmer. He would be a good client, if someone was having their first job."

"Fascinating," Cleo said, hoping Adelle would drop it. Unknown to Adelle, she had pulled up the same information on her screen. Adelle kept extensive records on her clients, which helped her to meet and anticipate their desires. Cleo could see that Mr. Dunn had never gotten anything but glowing comments from the girls assigned to him. She saw that three of the girls had indicated he had a proclivity for anal sex, but nothing too extreme. All of the girls gave him a star, indicating that they'd enjoy a repeat booking. This was in fact Sheila's fourth date with him. "Besides, I couldn't pass for one of your girls. He'd feel short changed."

"Cleo," Adelle said, and the force of her voice made Cleo look to the older woman. "Don't short change yourself, please. You are a striking young woman, and any one of these old codgers would gladly pay to get between your thighs." Cleo blushed at the compliment, and Adelle's eyes narrowed. Almost got her, she thought. "I'll give you the full fee if you do it. Plus a ten percent bonus, for sacrificing so nobly in the service of the house."

Cleo's eyes widened. The full fee alone was almost five grand, plus a bonus. Hold on girl, she said to herself, are you really ready to fuck a man for money? Well, a darker part of her mind snickered, it's not like you're fucking anybody for free either. Cleo straightened imperceptibly.

"Alright, I'll do it," she said with authority. She glanced down at her clothes. "But I think I need to change." Cleo went to the walk-in closet where she knew Adelle kept some spare clothes for emergencies like this, and went about finding something sexy to wear.

"I'll help you in a second, but first I have to call the client," she said, picking up the phone.

"Hello?" asked an older sounding voice, deep and rich.

"Good evening Mr. Dunn, how are you. This is Adelle, and I'm sorry to tell you there's been a problem with your appointment this evening."

"Ah, the mysterious Adelle," Mr. Dunn replied, "it's nice to finally speak to you. But there's a problem? Nothing serious I hope."

"Unfortunately, Sheila has fallen ill and will be unable to make it."

"Oh I see," Mr. Dunn replied, his displeasure evident. "Well that is disappointing. Is there anything that can be done?"

"In fact, there is," Adelle said, knowing that she could make the client's night if she played this right. "I have a new girl, you see, and I had been hoping to find the right gentleman to introduce her to the business." Mr. Dunn laughed on the other end of the line.

"Oh I'm sure," he chuckled.

"I'm quite serious, Mr. Dunn," Adelle said solemnly. "Cleo is filling in tonight, and I'm glad that a gentleman of your caliber will be her first client." Mr. Dunn's laughter died off, and Adelle knew that his cock just got a little harder.

"Very well... The original booking was for nine o'clock, will Cleo be able to make it in time?" Just as he asked, Cleo emerged from the closet wearing a black cocktail dress. The dress' built in bodice thrust her tits up, creating some lovely cleavage, and Cleo's slim legs looked fantastic with her black high heels. She had let her hair down, her lovely auburn curls tickling her shoulders.

"Yes sir, she may even be early. Thank you for being so understanding," Adelle said as she hung up. "You look lovely dear. Knickers?"

"I ditched the bra and, uh, I was wearing a cute little thong anyway, so..."

"That's fine. Are you... groomed?"

"I'm not bald if that's what you're asking. But it's not a jungle or anything." Cleo said, blushing. She went to the mirror and put on some quick make up. "Um, so is there anything I should... Like what about kissing? I thought hookers don't kiss."

"You aren't a hooker, you're a call girl," Adelle explained, stepping closer. "And kissing... I've heard it said that kissing is too intimate, but I must say I find that a bit silly. If you're going to let a man put his cock in your ass, you can let him put his tongue in your mouth." Cleo gawked at her, and Adelle waved her hand. "Just an example. But if he wants to kiss, kiss him. But what you do with your ass is up to you."

Cleo had to laugh a little. "So um, oral and uh, the usual then," she said, finishing up her lipstick. "I can't believe I'm doing this. I'm shaking like a damn leaf."

"You look lovely dear," Adelle said, smiling fondly at her newest charge. Cleo had also grabbed a small clutch, and quickly transferred her wallet and keys to the small bag.

"I can't believe I'm doing this," Cleo said, shaking her head as she headed to the door.

"Cleo," Adelle said sternly, going to her desk. She grabbed something out of a drawer and went back to the young woman. "Just relax and be yourself. The money has already been taken care of, so you don't have to worry about that. Don't let him tie you up and don't let him take any pictures of you. And if he does anything to hurt you," she handed Cleo what she grabbed from her desk: a can of pepper spray, "I want you to empty this in his face, kick him in the balls and get the hell out of there. Your safety is the only thing that really matters to me. Understood?"

"Yes ma'am. I can't believe I'm doing this."

"Relax, dear," Adelle said, fixing the younger girl's hair a bit, "you'll have fun, don't worry."

~~~~~~~~~~~~~~~

Cleo arrived at the 17th floor at the Waldorf-Astoria about an hour later, a little early for her "date." She stopped at a hallway mirror, and checked her makeup and hair. She had put on a deeper red lipstick then she would typically wear, as well as darker eye shadow and mascara. The overall effect made her look sexy, almost predatory. She shifted her breasts in her dress, noticed that her nipples were already quite hard. Okay, so maybe I'm not absolutely dreading this, she thought to herself.

"Fuck it, he'll appreciate me being early," she muttered, heading down the hall to Mr. Dunn's room. Taking a deep breath, she cleared her mind and focused on the job at hand. She knocked quietly on the door and waited.

"Good evening my dear," Mr. Dunn said as he opened the door. "You must be Cleo. Please, come in." Mr. Dunn was older, in his mid-40s, with salt and pepper hair. He was tall and broad, with a flat belly and strong legs, and Cleo was very pleased to see that he wasn't a corpulent old beast.

"Thank you," she said entering the hotel room. She jumped a bit when the door closed behind her, but forced herself to relax. The room was opulent, a large suite with a nice view of the snow shrouded city. She noticed a bottle of wine and some cheese and crackers on the coffee table, the TV was quietly playing a news channel. Turning around, she was surprised to find Mr. Dunn so close behind her. Even though he was barefoot and she wore heels, he still towered above her.

"Can I take your coat?" Mr. Dunn asked, helping Cleo remove the heavy coat and hanging it in his closet. He watched the young girl, was pleased with what he saw. She was slim and willowy, with a pretty face and piercing hazel eyes. He could tell she was nervous, and wondered if Adelle perhaps hadn't been bullshitting him. "Would you like something to drink?"

"Yes please," Cleo said, maybe a little too quickly. Mr. Dunn smiled and poured two glasses of wine, placing one in her tiny hand.

"To new beginnings, Cleo," he said, tinking his glass with hers.

"Indeed," she said, smiling. She gulped about half the glass down quickly, hoping to calm her nerves, and Mr. Dunn noticed.

"Adelle wasn't kidding, was she? You've never done this before?"

"No sir..."

"Andrew, please."

"Andrew. She wasn't, lying that is. I'm the booker, I just answer the phones and stuff. We were absolutely slammed with reservations tonight, and Sheila got sick at the last minute and I... Well, I volunteered," she finished, taking another sip of her wine. "I'm sorry to disappoint you. I know I'm not what you exp-"

"Stop right there," Andrew said, stepping closer, a hand moving to her side. "I will never be disappointed when a beautiful young woman comes to my room. Never." Cleo smiled at the compliment. "Did you have a chance to enjoy the snow today?" Andrew asked, moving to the couch.

"Not really. Like I said, it was very busy today," she said, joining him on the couch. On a whim, she placed her legs across his thighs. "Adelle says that snow like this makes people want to stay in and fu-uh, use our services."

"Ah, that is definitely true," Andrew chuckled, putting his wine down and removing Cleo's shoes, revealing her dainty feet. "My meetings ended early, so I was able to go to Central Park and walk around in the snow. I grew up around here, but I spend a lot of time in Texas and Florida."

"Eesh, sorry to hear that," Cleo said, immediately regretting the joke, but Andrew laughed.

"Right. And no snow to speak of. I really miss it, I find," Andrew said absently, now rubbing her feet. "So I walked around in a blizzard for a few hours this afternoon."

"Sounds nice enough. Cold, though." She was enjoying the foot rub. His hands were big and strong, but he was surprisingly gentle.

"It's not so bad. Keep moving and you hardly notice it," Andrew said as his hands slid from her feet to her calves, feeling the smooth skin.

"I grew up in California, where we didn't really have seasons at all. Then I went to college in Michigan. There're only two seasons there: winter and other."

Andrew smiled. "So New York?"

"You get all four here, as big as they can get. Hundred degrees in the summer, ten below in the winter, but the nicest spring and fall." Cleo laughed quietly. "Talking about the weather is so exciting."

"Quite," Andrew said, chuckling. "What did you study?"

"History and classic literature," she said. Off of his look, she shrugged. "I know. I'm a highly sought after commodity with those useful, highly applicable degrees."

Andrew shrugged. "I minored in history. Nothing fascinates me more than how we all ended up here. Look," he said, picking up an enormous book. "My light reading, Gotham. An exhaustive history of New York city, from the Native Americans to the modern era."

"I read that when he won the Pulitzer," Cleo said, nodding. "But you majored in... Finance? Business?"

"Law," Andrew conceded, sipping his wine. "I work in M&A now. Mergers and-"

"I know what it means," Cleo said, smiling slightly. "Are you with a firm or..."

"I'm a bit of a hired gun, actually. I really just come to New York to network and keep my name out there."

"It's always about networking, isn't it? I hate that," she said as she finished off her wine.

"It is that," he said quietly, watching her slim throat as she swallowed her wine. He and Cleo locked eyes, he noticed her lovely lips, their red vivid against her pale skin. "I'd rather like to kiss you, you know."

Cleo smiled, placed her glass on the table. He pulled her close to him, enfolding her in his big arms. The kiss slow at first, gentle sucking pecks at each other's lips. Cleo surprised him when she was the aggressor, her tongue pushing into his mouth, her hand going to his hair and pulling him against her. Andrew's hands slid down her thighs, cupping her firm butt in his hands, lifting her onto his lap. Cleo could feel his hard cock against her ass, squirmed down against it.