Jennifer Tests Her Wings

The door opened and Mr. 9 a.m. turned out to be in his mid twenties, and if Jenn's judgment was at all accurate, was totally in love with himself. Jennifer had only had sex with one person in her life, but she immediately suspected that this guy would be a step down from the previous evening. Weird. Two days ago she would have suspected that when it came to sex, 20-something would always trump 50-something, but now she wasn't so sure.

"Well, come in. Charlie said you were hot and I'm glad the old bastard's problems don't extend to his eyes." He turned around and headed for the bed. "You're supposed to be my wake-up treat so hurry up and get naked before I wake up."

Jennifer just stood by the door. "I think we need to get the money thing ironed out first, don't you?"

"Get in bed, baby. I'm sure not going anywhere!"

"I know, baby, it's just that I don't want any distractions while we're having a really good time."

"All right, all right!" He reached for his pants. "Five hundred bucks, you'd better be worth it.

"Trust me darling." She put the bills in her bag, dropped to her knees and opened the hotel robe he was wearing.

As Jenn undressed she pondered over her situation. It made no sense to her that she could be on her knees sucking the cock of a total stranger who she had taken an instant dislike to...and getting wet. There was no way that this objectionable arrogant man could be turning her on so. The inescapable conclusion was that it was the situation, the act of selling herself, that was causing her pussy to throb.

She pushed down hard, taking his tool deep down her throat for the first time. Her head began to bob as the John dug his fingers into her hair. She realized that she didn't know his name and was indifferent to that fact. She also came to the realization that deep-throating him wasn't going to help scratch the itch in her pussy so she pushed him onto his back on the bed and climbed on top of him.

The john groaned as Jennifer grabbed his tool and inserted him into her. As she began to ride him her mind was torn between her two goals; on the one hand she wanted to get herself off, but she also wanted to get the john off so she could get out of there. She twisted her hips and choreographed her movements so as to provide as much stimulation to the head of his cock as she could. She tried a little verbal stimulation to push him closer. "Oh my God, I'm coming! That's it, that's the spot, ohmygod you're terrific! That's it baby!!"

Jennifer thought to herself, 'Funny how things work out, here I am trying to get this guy all excited and I wind up getting myself offffffff.......' Her orgasm shook her completely. She felt the john cumming and that only added to her pleasure. She leaned forward, crushing her breasts against his chest as she nibbled his earlobe.

"Baby, you're the best!

Mind if I take a quick shower?" She grabbed her purse and dashed into the bathroom.

After the shower, as Jennifer started to get dressed the john was still lying in the same spot as when she had left. He hiked himself up on his elbows.

"You probably never had itthat good before, huh girlie? You probably should be tipping me but because I'm such a nice guy I'm going to give you the best tip you've ever gotten!" He walked over to the phone and dialed. "Mr. Harrison? I'll send her down now? Great, I'm sure you'll both have a great time...Right, see you at dinner."

I booked you a couple of guys from my company's division headquarters. They want to tag-team you up in 1204."

"Thanks but I don't know, I have an appointment this evening and I was going to get some rest and do some shopping this afternoon."

"Where were you going to rest?"

Jennifer laughed. "I hadn't worked that out yet."

"I'll tell you what. You go take care of my friends and I'll tell the front desk I'm going to be a late checkout. I'll be on a flight to Kansas City at 11 AM and you can keep the room until 5 PM."

"Two at once, huh? This'll be a first, but I guess the last 24 hours contains a lot of firsts! First time sex and first trick, those sort of stand out!"

"First time sex? You mean you were a virgin last night?"

Jenn looked sheepish. "Yeah! I traded my cherry for a room."

The john looked impressed. "Wow, the ultimate pragmatist!

So what do you say, will you take care of my friends?"

Jennifer sighed. "Starting on Tuesday I'll be returning to my ordinary life as a high school student finishing up her last year before going off to college. Until then I elected to try playing at being an upscale whore. If I really had to depend on this for a living, I wouldn't be turning down new business, so why not?

What'd you say, 1204?"

"That's it! Thanks, honey." He pushed an additional hundred in her hand along with the keycard to the room.

----

The two district managers had paid her well and Jennifer was done and on her own by one o'clock. She got the names of a couple of shops in midtown from a woman in the hotel and bought herself two designer knockoffs for $700. She had never spent that much for outfits before and by the time she had added shoes and outrageously yummy lingerie to her pile of purchases, she had spent more than half of the $2,800 she had earned in the last day. The superlatives kept piling up; most expensive outfits, first crotch-less underwear, first pair of designer shoes...she was having a ball. She picked up a few toiletries from her bag at the station and dropped off some of her new acquisitions. She then headed back to the trick's room. Allowing for time to get ready for herdate that evening, she left word for a wake-up call which allowed her a 45 minute nap.

Checkout time was 5 o'clock, so by 5:01 she was dressed for the evening and headed down the hall. She wasn't supposed to meet Charlie until 11 o'clock so Jenn decided to treat herself to a nice dinner instead of her usual trip to the closest Burger King. There was a steakhouse just off 7th Avenue her Dad had mentioned as a favorite hangout of Yankee baseball players, so she made a stop at the hotel bookstore and grabbed a cab to the restaurant.

The maitre d' had a single table back by the service hallway but after he took one look at Jennifer he knew he wanted to display her for a while. He sent her to the bar while he was "readying" a more suitable table for her on the railing of the high visibility second floor peninsula.

A gentleman quickly vacated his seat at the bar for her and bought Jenn a ginger ale. He went back to talking with his friends so she pulled out her book and began to entertain herself. She hadn't reached the second page before a voice interrupted her.

"What's an SPS?"

Jennifer looked up into the gorgeous eyes of a man in his late 20's with dark brown hair. She smiled. "They're Small Polyped Stony Corals. They're the kind that traditionally ripped the bottoms out of ships causing guys like you to drown. I breed them."

He leaned in closer. "Is that the end you have in store for me?"

"Not necessarily. I'm just giving fair warning to all those who unnecessarily interrupt my reading."

He took a sip of his drink and as he replaced the glass on the bar he brushed her forearm with the back of his hand. "And what about necessary interruptions?"

"Oh, you think you have one of those?"

He had moved in as close to Jennifer as he could get without becoming threatening. "Definitely! In fact, unless you already have a dinner date, I have the two words that will guarantee me a seat at your table, as well as possibly a place in your heart."

Jennifer was really enjoying this. "Really! I didn't know that there were two such words, much less that you'd have them!

What, pray tell, are they?"

His face was right in front of hers as he said, "Acropora humilis."

Jennifer's head pulled back and her face adopted a puzzled look. "I beg your pardon?"

"The cover photograph...on your book. Acropora humilis is the species of coral in that cover shot. I'm more of a Birdsnest fan myself. I've got a 180 that's a sea of Screaming Greens if you'd like a good sized frag."

Jennifer just stared at him for all of five or six seconds before flagging the bartender. Another thing her father had taught her was to learn and retain the names of service people. "Jeremy when you get a chance, would you please let Roy know that my single has just become a deuce as Mister...?"

Her new found coral keeper responded. "Leaback, Jimmy Leaback."

Jennifer nodded without taking her eyes off him, "As Mr. Leaback will be joining me."

The bartender responded "Jimmy's table has been waiting for him for 15 minutes, Jennifer, it's ready any time you are."

After they were seated at the point table Jennifer said, "Is now the point at which you embarrass me by telling me you're a Yankee who's been up for two seasons and I just didn't register on the name?"

"No, but I've got two clients who meet that description."

Jenn smiled, "Oh, a sports agent."

"Is that a good thing or bad?"

"A job's a job. To me the key's whether you do it well or poorly. Are you a good agent?"

Jimmy shook his head. "Oh god, is this going to be one of those 'money or happiness' talks?"

Jennifer kept looking at his eyes, "Not it all. I don't start with the presupposition that the two are mutually exclusive. I was just asking if you were proud of your body of work?"

Jimmy leaned back and it was his turn to look Jennifer straight in the eyes. "Yes, I am and I've never told that to anyone before because it's never been asked. Yours is a question which should be asked much more often, I think."

Jenn smiled warmly. "Me too!"

Dinner went very well. Jenn was really enjoying herself with this new man but finally said to Jimmy, "I'm having a great time. Areally great time but I think now's a good time to mention that no matter how much I'd like it not to be true, I've got to turn into a pumpkin in 35 minutes."

Jimmy grinned, "Got to get home before hubby finds out?"

"I'm not married and you probably already knew it. It's just that I've got an 11 o'clock appointment and I don't take such things casually."

"Okay, I can accept that. I'm busy through the rest of the weekend, can I see you Tuesday evening?"

Jennifer winced. "Probably, but I'm meeting an old friend and you'd have to put up with two giggling idiots remembering high school days."

"Wouldn't I be kind of a third wheel?"

"I don't know! I do know that I'm interested in you and that Carrie used to be interested in anyone wearing pants. Who knows, you might wind up with two girls trying to outdo each other in their efforts to impress you!"

"How can I say no to that?"

"Only if you have a strong sense of self-preservation! My parents used to say that they always slept fairly soundly when I was outexcept when I was with Carrie. On those nights they never closed their eyes." Jenn grinned sheepishly. "She was my catalyst and the resulting brew usually meant trouble!"

Jimmy smiled. "I'll take my chances. Let me get a check and I'll drive you to your next appointment."

"Your car is here?"

"It makes no sense whatsoever to use a car in the city which is why I always do." The waiter came over. "Add forty for Jeremy and a hundred for yourself and put it on my account, will you?"

"Sure enough Mr. Leaback."

When they got to the street the valet was already waiting at the curb next to a red Ferrari. The car was turning quite a few heads. She mentioned it to Jimmy.

"Bullshit! It's you that's turning all the heads. The car's simply a nice accessory."

Jenn did a mock curtsey just before she got in.

----

He pulled up in front of the hotel. Jimmy said, "I understand you have obligations but I kind of wish we were pulling up to a club where we could go dancing instead."

Jenn reached over and kissed him a quick peck on his cheek. "I appreciate your understanding and all, but I wish this was the front of your apartment building." He followed her peck with a more aggressive one. She wished she could spend her night with him instead of fucking Charlie, whoever Charlie is! Oh well!

Jennifer walked straight through the lobby as if she were heading for the hotel restaurant but after she was out of the line of sight of the front desk she turned a corner and headed to the bank of elevators. She thought it made sense to learn how to keep as low a profile as possible if she intended to fuck every guest in the hotel. She boarded the elevator on her way to room 716.

Jennifer knew that she'd encounter some difficult situations if she pursued this line of work (or 'hobby' as she liked to think of it), but most of the problems she'd anticipated involved dealing withdifficult johns. She was prepared for johns who were rude, abusive, or had poor personal hygiene, but she was completely unprepared for Charlie.

Charlie was polite, courteous, and considerate, in short he treated her like a lady from the moment she entered his room. He had already put her money in one of the hotel envelopes so she wouldn't be reminded of her status in their relationship. The way he spoke, the colloquiums he used, his mannerisms, even the way he tossed his head to flip errant hair out of his eyes, everything about him seemed to instantly set her at ease, but the idea of having him touch her seemed repulsive to her.

It made no sense to her. Shereally liked Charlie but was having a huge degree of difficulty getting into the frame of mind to become intimate with him. Then, as Charlie was getting them some wine to drink, he tossed a comment over his shoulder aimed at her and she figured it out. She started laughing and Charlie gave her a puzzled look. "What's so funny?"

"Oh Charlie, I just realized something and it struck me as being hilarious. Ever since I set foot in your room I felt totally comfortable. I don't know that anyone has ever made me feelso at home so quickly, but for some strange reason I was having trouble getting into the mood for our evening's fun and games.

Then it just struck me. You're my father! Your general appearance, mannerisms, mode of speech, sense of humor, they're all identical. That explains my being totally at ease with you, but it also explains why I felt funny about the concept of getting naked in front of you."

"I guess that means that either I've got to start acting differently or you have to start getting into the concept of incest."

Jennifer walked over to Charlie and put her arms around him. "Don't you dare act differently"! She kissed him with quite a bit of tongue. "Not that I know what the problem was I'm sure I'll be fine. Either that or as you say..." She placed his hand on her breast. "I'll just have to get used to fucking dear old Dad!"

Jennifer pushed Charlie onto his back on the bed and began to strip. She'd seen enough movies with strippers in them that her moves were pretty good. Charlie certainly seemed to approve as she shed her red dress revealing her new $400 lingerie. His eyes were glued to her every movement. Jenn unhooked her bra and leaned over him letting her nipples graze his lips. As he began to take each one, in turn, between his teeth his hands went to her panties. While his left hand explored her clit beneath its hood his right hand worked the panties down her legs.

While Charlie worked on her, Jenn undressed him. After she pulled his pants to the floor she dropped to her knees and started licking the head of his cock. It didn't take Charlie long before he had rolled Jenn over onto her back and started fucking her.

Then it was over. He kissed her before rolling over. "That was great, honey. I can't wait for my wake-up encore."

Jennifer's legs were still spread and her breathing had not yet returned to normal when she heard the measured sounds from the pillow next to her. He was asleep. Jenn looked at her watch and realized that it wasn't even an hour since she had walked in the door to this room. She quietly slipped out of the bed and headed for the bathroom to finish getting herself off. She smiled as she thought, 'Mom smiles all too often in the morning for Dad to be this quick. At least that's one major difference between Charlie and him!'

Between Jenn's trip to the bathroom and six thirty the following morning Charlie seemed to discover the closet in which he had hidden all the energy he hadn't had the previous evening. Charlie started caressing her and Jenn awoke to the delightful sensation of his head buried between her legs. By the time she was aware of what was going on she was half way toward her first orgasm of the day.

When she came Jennifer could feel herself squirting into Charlie's mouth yet he only increased the pace of his mauling her clit with his tongue. Without removing his tongue he slipped two fingers into her. She thrashed from side to side, her hands rapidly shifting from grabbing Charlie's hair, then her own nipples, her mouth, her own hair, all as wave after wave crashed over her. Jennifer grabbed a pillow and screamed into it as her heels dug into Charlie's shoulder blades, giving her the leverage to drive her cunt into his mouth.

Charlie flipped her over and as he kneeled between her legs he grabbed her hips and entered her doggie style. Jenn continued to scream into the pillow as his balls slapped into her exposed clit.

After two more in what seemed to Jenn like an endless string of orgasms, Charlie removed his cock and started rubbing its head against her anus. Jenn froze. This was one act she had always thought to be on heroff limits list but Charlie had her in such a state of arousal that all she finally thought to herself was 'okay, another first!' It felt like Charlie had grown to baseball bat proportions as his cock entered her virgin ass. After entering her he paused to let her get accustomed to his size. It was Jennifer who finally began the first movement as she began to slam her butt back against Charlie.

----

Jennifer awoke spooning in Charlie's arms. She liked it there. She thought back to the previous evening and smiled to herself when she remembered her disappointment in his earlier performance. She realized she was wearing the same grin she'd frequently seen on her mother's face all those mornings. Maybe there were more similarities between Charlie and her dad than she had thought!

He spoke to her. "At last you're awake."

"I'm awake."

"I've been watching you for over an hour. You're quite lovely as you sleep."

"What time is it?"

"Around eleven, are you in a hurry to get somewhere?"

"Not at all. It's just that I thought you had a ten o'clock appointment."

"I did. I took the chance of waking you up and called in, I think 'indisposed' was the word I used." He chuckled. "It was particularly noteworthy as I was the featured speaker!"

"Will you get in any trouble over it?"

"Doubtful, since I own the company. My assistant is working on rescheduling my talk for one of the other meetings. Ben Roberts is the head of one of my branch offices."

Jennifer rolled over in his arms and kissed his chin. "Oh! So I'm entertaining the big boss!"

"And doing an excellent job I might add.

Want to go out and get some brunch?"

"I'd love to but all I have to wear is the dress I had on last night."

"Ben said you were just moving around until your friend comes home on Tuesday. Where are your things?"

Jennifer adopted an embarrassed look. "Checked at Penn Station."

"Not to make this sound too much likePretty Woman, but why don't I hire you until Tuesday morning? Then you can keep your things here."

"How much would you pay me?"

"Oh, let's see, 48 hours or so, at $75 an hour would be $3,600 but since I'd want you to be exclusive to me, oh let's say $100 an hour. How about 4,800 dollars?"

"Done! Also not to sound too much like the movie but I would have done it for half that." She kissed his nose.