Jennifer Tests Her Wings

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Reefkeeper
Reefkeeper
142 Followers

"So it's my turn to say that I enjoyed last night so much that I would have paid double!" He squeezed her ass as he shook his face between her breasts. "But you'd better get up so we can feed ourselves. There's a shop in the hotel where you can pick up an outfit for brunch. After we've eaten you can go to Penn Station to retrieve your things while I hit a meeting."

Jenn jumped out of bed. "Sounds like a plan!"

----

Charlie took her to a place on the west side that served a champagne brunch and overlooked the river. Jennifer wanted a Mimosa with her brunch so she dug out a fake I.D. Carrie had given her for her eighteenth birthday but the waiter never asked to see it. She was mildly disappointed.

"So have you decided yet where you want to go to college?"

"It's not set in stone yet but I've been accepted into Cornell's Veterinary School and I've had my heart set on getting my DVM since I was about eight!

And you have a Real Estate Company!"

"Yes, we're about the biggest independent in the state of Alabama. Speaking of that, since you're my newest employee and I can't spend all day doing what I'd most like to do with you, here's my secretary's card. While I'm in the meeting this afternoon I want you to liaise with her and work out the best time for me to give my little talk. I definitely want it to happen before I leave for home."

Jenn put the card in her purse. "This is a nice restaurant. Have you ever been fucked in its men's room before?"

Charlie smiled. "No and I'm not going to be now. Missing one meeting is spontaneous and fun loving but missing two is irresponsible.

Here's my corporate plastic. Buy yourself two outfits for you to wear to dinner both this evening and tomorrow."

"Okay boss man!"

----

Jennifer hit it off with Charlie's secretary immediately. The woman's name was Nancy and Jenn suspected that Nancy's job interview had once gone something like hers. As the girls quickly discovered the problem with getting all of Charlie's employees at a meeting so he could address them revolved around prior commitments to other meetings. They divided the list of employees in half and agreed to follow up with each other in three hours.

The first thing Jenn wanted to do was make sure everyone was feeling safe about her. She composed an e-mail to her dad.

Hi! Just a quick note to let you know everything's okay. We were in the city yesterday and ate at Del Frisco's. Didn't meet any Yankees but did meet a sports agent, do they count? Everyone's keeping me busy.

I suppose it's time to say that youmight have been right. I might have been getting in over my head with that crowd at the beach.

Anyway, love,

Jennifer

She sent it from her Blackberry and then proceeded to start calling her list of employees of Taylor Made Realty. There were a few grumblings from some of them but virtually all of them allowed themselves to be coerced into canceling prior commitments and attending Charlie Taylor's talk. When she called Nancy it turned out that she'd had identical results. Each had one holdout that claimed it was too late to change his plans.

Jennifer said to Nancy, "Give me your guy's name. Maybe these two might need some face to face convincing."

"The name I'm showing is Rawlings in room 782 and I'll text you the cell number. It's in my Storm downstairs but darlin', I think you're wasting your time with this hard nose."

"It can't hurt if I try. Did you say you had a Blackberry Storm? How do you like it?"

Nancy gushed. "I love it. It even makes little clicking sounds so you know you've hit the key hard enough."

"I might upgrade mine. Anyway, I'll start working on my guy and I'll look for your text with Rawlings number."

Jenn headed down the hall for the bank of elevators where she took one down to the fourth floor and knocked on the door. A man in his late 30's answered.

She decided a new name was called for. "Hi, I'm Jennifer Tate and Mr. Taylor wanted me to see if there was anything I could do to convince you to change your plans and attend his meeting tomorrow afternoon. If I can convince you, then he'd have 100% participation."

The guy looked frustrated but Jenn also noticed that his eyes hardly ever left her tits. That was a good start! "Look, what was it Jennifer? As I already told the other young woman who called earlier, Charlie's talk was supposed to be this morning and I had it scheduled. My entire day tomorrow is pretty crowded."

Jennifer moved invery close to him. "Look, I promised Mr. Taylor that everyone would be there." She rubbed the lapels of his jacket. "Isn't thereanything I can do to convince you to make thisone tiny little accommodation? I can be a pretty good convincer!"

Forty-five minutes later Jennifer ran her tongue across her teeth as she rode the elevator back to her room. She wanted to brush her teeth before heading for the seventh floor to take on Rawlings since it felt like they were still coated in cum.

The message light was blinking is the room. There was one message on the room phone from Charlie. She called him. "What's up Boss?"

"How are you and Nancy making out?"

"We've got commitments from everyone but one remaining holdout. I'm on my way to the last person's room to do a little arm-twisting as soon as I hang up the phone. Don't worry Bossman, my goal is 100% participation."

"Meet me in the cocktail lounge at around seven?"

"Great! The only thing which might slow me up is that last holdout but I'll be there."

"Then be away and go quickly."

Jennifer knocked on the door to room 782. It was answered by a fairly attractive woman in her early forties. "Hello, I'm Jennifer Tate and I was looking for Mr. Rawlings."

The woman smiled, "He's dead, I think, at least I hope! I would have killed him myself if I'd had the balls!"

She sighed, "So I divorced him instead. Since he could therefore be of no possible interest to you, who are you really looking for?"

Jennifer's head was reeling but she forged on. "I was looking for a Group Manager in the employ of Taylor Made Realty."

The woman backed up and gestured for Jenn to come in. "Then, my dear, you've come to the right room.

Can I interest you in a glass of Merlot?"

Jennifer's radar told her that turning down the wine would be a mistake. "Thank you. I'm sorry for assuming that the Rawlings I was looking for was a man. I should know better."

The woman waved her hand in a dismissive gesture. "Don't worry about it. I'm not going to go all feminist on you Jennifer, I'm Gloria."

She handed Jenn the glass. "What's up?"

Jenn took a sip. "I work for Charlie Taylor and I came here to talk you into changing your plans and coming to his presentation tomorrow."

Gloria just smiled. "Actually I was looking forward to hearing Charlie pontificate..." She tilted her head and continued to stare at Jennifer. "Then he blew us all off. You wouldn't happen to know why he did that, would you Jennifer?"

Jenn was absolutely sure that Gloria already knew the answer to her question. Jenn was operating on instinct now. "Yes I do, Gloria. His head was otherwise occupied between my legs eating my pussy."

The silence was palpable. It went on for almost 20 seconds before Gloria started laughing. Jennifer tried to maintain her composure but lost it fairly soon and was soon laughing as hard as Gloria was.

"Okay, Honey, that's about the best excuse for Old Charlie canceling out as I could imagine! I'm actually jealous. Okay I'll be at his meeting tomorrow on one condition."

It was Jennifer's turn to tilt her head and smile.

Gloria laughed. "No, no, no! As much fun as that might be, what my condition is is that you tell me how Old Charlie convinced a hot little ingénue-type like you to climb into his bed."

Jennifer shook her head. "It's been my experience that most guys like to talk about their conquests. Why don't you ask him?"

"That came out of a book, Jennifer. Guys only brag like that among their buddies. I'd have no shot getting that kind of information out of him. On the other hand, it's been my experience that just about the only way to keep women from talking about sex is to muzzle them."

The silence went on a little longer and then Jennifer spoke. "He paid me a thousand dollars."

"I thought as much. May I hire you right now?"

"I'm still on Mr. Taylor's payroll, actually. I do think, however, that it would be within the scope of my employment to thank you for attending tomorrow's meeting." She walked over and sat on the sofa next to Gloria. As the older woman was about to kiss her Jennifer felt compelled to say, "I thought I should let you know I've never done this before, you know, with a woman."

Gloria said, "Oh goody, a virgin!" And then began to devour her. Jennifer's clothes were tossed over the back of the sofa in no time and just as Gloria was about to go down on her she thought better of it and led her to the bed. As Jenn was helping Gloria undress she was counting; Ben, Mister 9AM, the twofer, Charlie, the blowjob, and Gloria made seven. She'd was having sex with herseventh stranger for money. She figured that somewhere in the last 36 hours she'd long since crossed the line and was now a professional prostitute.

By the time Jenn got to the cocktail lounge it was 7:45. Charlie already had a bit of a buzz. "Do you mind if I pay my check and we go straight to the table? If I have anything more to drink before food I won't be any good to you later."

She leaned in and kissed his cheek. "That's fine. I'm sorry I'm late but I was still working on your meeting."

He signaled the bartender and signed the bar check. In the dining room as he held her chair for her he asked, "And were your efforts successful?"

As she placed the napkin in her lap Jen proudly said, "I have commitments from 100% of your people to be there tomorrow."

"That pleases me. Who was the last holdout who took extra convincing?"

"Gloria Rawlings."

Charlie laughed. "Gloria, I'll bet she took a lot of reallyspecial convincing!

How was that?"

Jennifer half closed her eyes and tilted her head back as she said, "Nice, she puts a lot of attention into seeing to her partner's pleasure." She shook her head. "Nice, but I still prefer men."

Charlie reached into his pocket. "I'm pleased with the job the two of you did. I've already checked in with Nancy and she confirmed that you really did it right. You impressed her and most people don't!"

"She seems really nice." Jennifer paused before adding, "I also got the impression that she might have some experience with bedding the boss; at least she certainly acted like she knew I was!"

Charlie smiled, "She and I have had some fun times over the last couple of years but she's engaged now and although her boyfriend has never come out and said anything specific, she thinks he might suspect there was something going on between us.

This time last year she would have accompanied me on this trip but these days we confine our games to a bed in the model home of a community we're selling." He pushed the envelope he had taken from his pocket toward her across the table.

"There's an airline ticket in there for the noon flight out of Kennedy headed for Birmingham. When you get there a car will pick you up and take you to the office.

Nancy has some contracts you need to get signed."

Jennifer asked, "Birmingham? I thought I was your New York toy."

"You're an employee and as such you work where I need you. You have a problem with flying?"

"No, Boss."

"Good. After you're done, fly right back. I can hardly wait to get my hands on that body of yours."

----

"I was thinking." Nancy placed her hand on top of Jennifer's in the back of the limo. "You and I need to get to know each other and Charlie really needs these contracts signed today...why don't we tag-team this guy?

I'll bet we get his signature in no time flat!" Nancy reached into her purse and pulled out a metal embossing stamp. "I even brought my Notary Seal!"

Jenn leaned over and kissed Nancy full on the lips as she thrust her tongue into the girl's mouth.

When the kiss broke Nancy said, "I take it that's a 'yes'!"

Jenn sat back in her seat. "Sure! Sounds like a good idea to me!

So how did you meet Charlie?"

Nancy chuckled. "I was eighteen and a friend told me about a modeling job she had just landed at the boat show. Three hundred dollars to just stand around and look pretty. I asked if she could get them to hire me too. She did and they did.

There were five of us working for this yacht broker and on the last day of the show he asked us if we wanted another day's work. He had three hot prospects interested in buying yachts and he wanted to take them for a weekend sail off the coast of Florida. He wanted three of us to come on the sail and be 'nice' to the prospects. I immediately said I wasn't interested. I got offended that he would think of us as being whores but my friend asked how much the weekend paid. When he answered $1,200 for each girl Connie accepted and convinced me to do it too! Charlie was one of the prospects who went on the sail."

Nancy started rummaging around in her purse. "He wound up buying a boat, too!

You got any Tic-Tacs or anything like that? I think my breath is foul."

"Oh I don't know, you tasted pretty good to me."

"Oh boy, I think Charlie found himself a really horny little wench to replace me!"

Jenn said, "Oh, I'm not replacing you, I'm just a temp!"

Nancy smiled, "So you say now!"

----

The two girls were shown into the offices of Ray Waldorf, owner of a successful electronics firm. He said, "So what's new, Nancy?"

Nancy sat on the corner of the desk and leaned so as to show as much cleavage as possible. "Nothing too much, Ray. Charlie just wanted me to get this contract for the Cole property signed."

"Iknew they'd come back with a better offer! How much?"

Nancy shook her head, "Ray, Charlie told you that the two million seven was as low as they'd go and you knew that's a great place for the money!

Sign the contracts, Ray, so I can give you your signing bonus."

Ray sat back in his chair. "Signing bonus?"

Nancy said, "Ray meet Jennifer, Jennifer, Ray.

Charlie went to his localTeens 'R' Us and got her as an extra special present. I thought you and I could share her this afternoon if that's all right with you."

She turned to face Jennifer. "Jenn, take your shirt and bra off so Ray can see his present better." Without saying a word Jennifer stared into Ray's eyes and removed her shirt and bra, placing them on one of the client chairs.

"Now Jennifer go over and let Ray have a taste of your lovely nipples.

Oh! Why don't you take this contract with you? You can sign for the company and I'll notarize both your signatures and we can get down to having a little party!"

Jenn put the contract on the desk, open to the first page needing Ray's signature and unbuttoned her skirt, pushing it to the floor. She took the pen and signed on the line next to Ray's. She said, "While I'm signing these would you mind removing my panties? No sense wasting time, is there?"

As Jenn and the client were signing, Nancy had just completed undressing and came over with her notary stamp.

Ray seemed mesmerized by what seemed a sea of breasts surrounding him. "Istill think I could have gotten that property for 2.6 but what the Hell!" He grabbed Nancy's tits and began sucking. Jenn had unbuckled his belt and was pulling his pants and underwear off as her lips eagerly gobbled up his cock. She felt Nancy's hand reach between her legs and seek out her clit.

----

Jennifer was awakened Tuesday morning by the sensation of Charlie sucking at her breast. She wrapped both arms about his head and tenderly kissed the bald spot on the top of it. She had thoroughly enjoyed her long weekend in New York but she also looked forward to seeing Carrie again.

She had some feeling of urgency so she pulled Charlie on top of her and guided him into her. "Oh Charlie, that feels so good! I'm really going to miss this."

She had come to the city pretty much inexperienced and subsequently had quite a lot of sex but she absolutelyknew that she was now making love for the first time. She wasn't quite sure what set it apart, but she liked it, shereally liked it!

Both Jennifer and her father had had the attitude that when the two of them hooked up Connie was somehow going to corrupt Jennifer. Maybe that still might happen.

On the other hand it might just work out the other way around! Jennifer grinned and wrapped her arms tightly around Charlie's head and shoulders. She kissed him hard as he drove her toward her orgasm.

Reefkeeper
Reefkeeper
142 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
james3363james3363almost 12 years ago
The best. By far.

I have been a very longtime lit member and can easily sat that parts 1 and 2 of this story are the best I have ever read.

ReefkeeperReefkeeperover 15 years agoAuthor
Author's reply

You're 100% right! It was always my intention to do a follow-up story with Jenn, Carrie, Charlie and Jimmy. In fact, I had the second part already blocked out but was afraid that if I just added it to this story it would get too long.

Thanks for the words of encouragement.

AnonymousAnonymousover 15 years ago
Good

Good story, but it does need finishing. Maybe turn it into a series.

doctor2longdoctor2longover 15 years ago
Pretty good start....

You need another page to bring Carrie into the story and to wrap things up with the Sports agent. Even if you write another chapter later, this one needed to at least indicate something about those two characters that you introduced earlier.

Oldman-PaOldman-Paover 15 years ago
more i hope?

nice

hope there will be more

thanks

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
Strip Poker: Five Girls, One Guy Game with girlfriend and friends gets out of hand.in Group Sex
Tara's Breeding Three men decide to have their way with fertile Tara.in NonConsent/Reluctance
Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
Bosom Buddies Ch. 01 A nerd befriends the 5 hottest girls in school.in First Time
More Stories