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Jennifer Tests Her Wings

By: Reefkeeper



"Jenn, we're not going to argue about this any more! I don't care if it is your eighteenth birthday coming up. You're not going to just take off for the beach for the weekend without a bit of planning. Your mother and I need to know a little bit more about the arrangements.

You don't even know where you'd be sleeping!"

"Dad, that's not true. I already told you that it was all set up for us to stay at Tammy's friend's family's beach house. The house is huge and has plenty of room for all fourteen of us!"

Stan Reynolds sighed. "Okay, what's Tammy's friend's family's name?"

Jennifer looked at her feet. "She didn't say."

"And where is this house?"

"I already told you, Ocean City!"

"Come on Jenn, where in Ocean City?"

"Above 125th Street."

"Work with me Jennifer, if I were to tell a cab driver to take me to the house 'above 125th Street' what would you guess at the odds that he'd drop me at the right house? How about an address?"

"She didn't say."

"And who'd be staying at this house?"

"Me and Tammy, Lucy Parker and a bunch of other guys."

"Guy guys or girl guys?"

"Some of each I guess, she didn't..."

"I know, I know, 'she didn't say'!

I'm sorry Jenn, that's just not good enough." Stan sat on the sofa next to his daughter and took her hands. 

"Look kiddo, I know that father's sometimes have a problem with letting their daughters grow up and fly on their own. I try really hard to guard against holding on too tight but while you're out testing your wings I just want to see that you've got a soft place to land if the first few flights don't work out quite like you planned.

You didn't want a birthday party here, fine. You want to get out and be with friends, fine. You want to get a little wild and have some fun, fine. I'm not worried about drugs or alcohol because you've always shown me tons of common sense. Just let me feel like you've planned for some sort of safety net out there."

Jennifer had her arms crossed across her ample chest and her lips locked. She knew her father was probably right but she didn't want to give him the satisfaction of her giving in.

"Okay, I get it, you're not speaking to me, also fine, but you're still not going to Ocean City!" Stan got up and started to leave the room. As he got to the door he paused and turned around.

"I just thought of something." He shook his head. "I can't believe these words are coming out of my mouth but..." He hesitated again, having a hard time giving voice to his thought. 

"Why don't you go up and visit Carrie? I'm sure she'll try to get you in as much trouble as you could want but at least I've got the knowledge that you'd have her parent's house to fall back on if she gets too crazy for you." Carrie Lewis had been Jennifer's best friend from toddler days right up through when her father was promoted in his job and their family moved to New York. As they were growing up their families were always alternating babysitting duties so the two girls were frequently sharing a room as they grew.

But while Jennifer had grown into a very responsible straight A student, Carrie had blossomed into the school wild child.

They were both bright and excelled in their schoolwork, but while Jennifer's college application glowed with extra curricular activities; Captain of the swim team, editor of the school paper, active in the drama department and tennis team, Carrie's looked rather sparse.

Not that she didn't have just as many achievements, they just weren't the sort to impress an admissions office; first girl to lose her virginity, publisher of the best counterfeit hall passes, first girl in the school's history to be caught with a boy in the Principal's conference room, first student in her class to seduce a teacher...

Ordinarily Stan might not have considered encouraging his daughter to visit Carrie were it not for the fact that Jenn had, on several occasions, left Carry to come home early claiming her friend had gotten 'a little out of control'. Stan smiled internally, proud for having helped raised a very responsible daughter.

Although Jenn wasn't going to give her father the satisfaction of a response, his suggestion set off fireworks in her mind. 'What a great idea!' She'd missed the late-night talks she used to have with her friend. As soon as her dad rounded the corner she grabbed her Blackberry and texted her friend.

***my dads letting me visit u.want company 4 a couple wks?

The response arrived in mere seconds.

***k, in fact vry vry k. parents been trying 2 drag me 2 bostn pops 4 the quajillionth time thurs. you're my xcuse to get out!!!

***k I'll set it up and get back

***k

At dinner Jennifer told her father that she'd contacted Carrie and set it all up. She decided to be magnanimous and throw him a bone. "Carrie said her parents are all excited and want to take us to the Boston Pops."

Before her father could respond her mother jumped into the conversation. "I'm not crazy about Carrie's wild side but I still love her and you can go on one condition."

Another roadblock! "What condition?"

"Since tomorrow's your birthday I'm cooking breakfast and since I didn't get to make a cake for you I'm putting candles on the God Damn pancakes!"

Her mother never swore so the entire family's jaws dropped just before everyone started laughing. Jennifer got up and hugged her mother. "Okay Mom, candles and Vermont maple syrup it is!"

Her father made a reservation on the Acela express train to New York. "Your train gets into Penn Station at 6:45. Just grab a cab over to Grand Central. That's still the tail end of rush hour so there'll be plenty of northbound trains going up the Hudson." He thrust some folded bills into his daughter's hand.

"Thanks Daddy but I'm not wasting any of this on a cab. I can get a subway from Penn Station up to Times Square and take the shuttle over to Grand Central."

Stan looked at her in amazement. "How do you know that?"

"I looked it up online."

"Amazing! But I'd still feel safer with you in a cab."

"Daddy you just said it was still rush hour. The Ted Bundy mass murdering rapists don't come out until the commuters have left. You don't want me to tell you a fib and just go ahead and do it anyway, do you?"

"Okay, okay, just use your common sense. Love you." He kissed her on her forehead.

----

When she was about an hour out of the City Jennifer started trying to call the Lewis' landline phone. She knew Carrie's father wasn't crazy about using cells in the house and Jenn wanted to thank them for the invitation. After an hour of no answers however, she texted Carrie.

***been trying 2 call ur folks 2 thank.no anser.wat's up?

***call on cell?

***no. hse phone

***duh! We'll b home tues 

***where r u?

***Finger Lakes. Pretty, but boring!!!

***tues?

***yeah. y?

***I'm coming up

***looking forward 2 it/ btw, when?

***like NOW

***no shit!

***don't wrry. I'll hotel it and c sites.

***in Tarrytown? Sry, no sites. better stay in city, more 2 do

***k. c u tues 

Jennifer immediately checked the money in her bag. She knew the $58 she had and the three hundred her dad had given her wouldn't last long in Manhattan. She thought about going home but she couldn't face admitting her blunder to her Dad. She needed time to think. The first step, she reasoned, was to find a reasonably priced hotel. Rather than schlep her bags around while looking, she checked them at the station.

The first hotel's cheapest room was $195 but they were completely booked. Jennifer went down the street and the next one quoted her a rate of $255 but they too were completely sold out. She asked the desk clerk "I really need a room but I'm kind of on a limited budget. Can you recommend some place around here?"

"I think most of the hotels in midtown are going to be filled also, Miss. There's a National Realtor's Convention filling all the moderate priced hotels. However we do have some reserved guests who haven't called or taken their rooms yet. I think you might want to come back at 10 PM and you might get lucky."

He turned toward another guest. "I checked with the concierge Mr. Roberts and your guests have already picked up the theater tickets you left for them."

The guest smiled. "That's great, thanks very much." Jenn saw him hand the clerk some folded bills.

Jennifer sat in one of the lobby sofas trying to figure out what to do. If she could only get a roof over her head until tomorrow she might be able to stay at the Lewis' place the next day.

"I couldn't help but hear you talking to the desk clerk. Don't you have any friends in town you could call?" It was the man the clerk had called Mr. Roberts.

Jennifer shrugged her shoulders. "Ordinarily yes, but her parents took her out of town until Tuesday. I've just got to figure a few things out. Thank you for asking, though."

He held out his hand. "Ben Roberts."

She shook it. "Nice to meet you, I'm Jennifer Hill."

"I don't know about you Jennifer but I always think more clearly on a full stomach. I'm alone in town for the convention and I was about to have dinner in the hotel restaurant. May I buy you dinner? I could use the company and you look hungry.

Jennifer sighed. She assumed this fifty something man was hitting on her but it was a public place and she was getting hungry.

"I think you're right, Ben. I'd love to join you for dinner."

A friend of Ben's stopped by the table and shook his hand and walked on. Over dinner Ben chatted about a variety of things but Jennifer's mind kept coming back to the sad realization that she was in a corner and the only way out was to call her father for a bail out. 

She hated admitting defeat, but she couldn't see any way out. She felt like a helpless little girl and felt disappointed in herself.

Ben was still speaking. "I guess I've been rambling. I'm sorry but I did think of a way to solve your problem but I'm trying to get up the nerve to see what you think."

He had Jenn's full attention now. "Ben you have no idea how much I hate the idea of confessing to my Dad that I'd screwed up. What's your solution?"

Ben was wringing his hands. He finally took the plunge. "Okay, here goes. If I hadn't run into you I would have had a quick bite, gone up to my room and called one of the escort services for some female companionship. It would have cost me either $500 for a good time or $1,000 if I wanted her to spend the night. I probably would have opted for the $500.

Now I don't want to pressure you in any way and I'm sure you never would have considered doing anything like that, but quite frankly I'd much rather pay you than some hooker I've never met. You're so incredibly lovely that I've wanted you since you opened your mouth at the front desk.

If you'd consider it, you'd have a safe place to spend the night and leave tomorrow with $500 extra in your purse. If you don't want to I'll certainly understand, but then I'll definitely have to call that service now because just thinking about bedding you has got me horny beyond words."

Jennifer stared across the table at Ben's eyes. He looked more frightened and embarrassed than horny. "Would the form of your solution be any different if I admitted to being a virgin?"

It looked to Jennifer that he was actually giving her comment some serious thought. "It's certainly surprising and I know that would ring the bell for a lot of guys, but quite frankly I don't think my dick could get any harder than it was already from just looking at you."

Jennifer took a deep breath and exhaled. "Mr. Roberts, you've got yourself a roommate!"

Ben signed the check and the two of them were riding up in the elevator when Jenn said, "I said you'd gotten yourself a roommate. As I think about it though I guess that's not really true. I guess you just hired a whore, didn't you?"

"I wouldn't exactly put it that way."

"Why ever not? I didn't want to admit a mistake to my dad, so instead I'm fucking someone I've just met for money. That makes me a whore! It's an interesting feeling. I'm not sure yet, but it might almost be exciting!

I take it you've hired professionals before?"

"A few times."

She took his arm and squeezed it. "Well then you'll have to teach me what to do. If I'm going to do this I want to be the very best whore you've ever bought!"

Ben took her in his arms in the elevator. He had his tongue in her mouth and his hand under her bra before they got to his room.

As soon as they got to the room Jennifer took off her jacket and started unbuttoning her shirt.

"Okay, if I'm supposed to be your teacher, a pro never does anything until she'd collected her money." He took out his wallet and counted they cash into Jenn's hand.

She whistled. "I guess this makes it official." She continued removing her clothes as Ben sat on the end of the bed. When she pushed down her jeans he stood and put his arms around her, unclasping her bra as he kissed her. Jennifer's hands began to unbutton Ben's shirt. When they were both naked Ben sat back on the bed and with his hands on her shoulders pushed Jennifer to her knees. She didn't need any instruction at this point, having sucked off a few boys in her high school. She grabbed his penis around its base and began licking her way along the shaft and around the head. When she was sure it was properly lubricated she lowered her head consuming more and more of the shaft until it slid down her throat. She smiled inwardly at his gasp. She thought, 'Jennifer Reynolds is the name, deep throating's my game!' She knew she was good at that. Her head started bobbing up and down like a girl on a mission. Ben laced his fingers into her hair but made no attempt to run the show, as he'd  never had a blowjob like this before. Five minutes later he could feel himself getting ready to shoot his load and he clenched his fists in the sheets rather than pulling her hair out.

Jennifer felt wave after wave of sperm shooting down her throat and for the first time in her life found herself completely turned on. She'd always thought of blowjobs as being just for the boy's benefit but she was as wet as she'd ever been and was just a few strokes short of her own orgasm. She felt a moment's sadness as his cock slipped out of her mouth but Ben grabbed her by the armpits and threw her on her back on the bed. He kissed his way from her lips to her erect nipples and on to her stomach. He positioned himself between her legs and slid his hands under her, tightly grasping her butt cheeks as he rubbed her wetness along the bridge of his nose. As soon as his tongue started rubbing her clit she exploded. Jenn unashamedly tried her level best to scalp Ben as her fists twisted as they were filled with clumps of his hair. Her scream was mixed with a prolonged groan as she squirted her juices over Ben's face.

Ben pulled himself up level with Jenn and kissed her. "Do you want to shower?"

She kissed him back. "I will if you need the time to recuperate, but I'd just as soon give you the fuck you paid for. I've never felt like this before. It feels like my pussy's on fire!"

Ben continued kissing her. "Sounds like a plan to me!" With his arms locked around her Ben rolled onto his back pulling Jennifer onto his chest. His fingers dug into her ass cheeks as he thrust into the previously unexplored territory of her vagina. 

Jennifer quickly overcame the moment of pain and started performing a reasonable imitation of a bronco rider on Ben's cock. He reached up and grabbed her very erect and very prominent nipples as she rotated her hips and continued to grind against him.

Ben moved her off him and pulled up on her hips so he could enter her doggie-style. As soon as he entered her the room's phone began to ring but he ignored it. His balls slapping her clit was driving Jenn rapidly toward another orgasm as he began to cum. Jenn screamed again as they both charged across the finish line.

They lay in each other's arms trying to catch their breaths. Ben just snorted out one word. "Wow!"

Jennifer smiled up at him, "So I did good?"

Ben kissed her forehead. "Best I've ever had!" He noticed the message light blinking on the hotel phone so he got out of the bed, dialed the access number and then redialed.

"Charlie? Ben Roberts, you left me a message to call you." He listened to the response and replied, "I'm pretty well tied up for the rest of the evening but why don't I find out and call you back?" He hung up the phone and dropped back on the bed next to Jennifer.

"Remember the guy who stopped by the table at dinner last night?"

Jenn kissed his shoulder. "Sure. You called him Charlie. I take it that was him you just called?"

Ben nodded. "Returned his call, actually. He wanted your number."

"My number? I never saw him before."

"He saw you at the dinner table and put two and two together since only an hour before that I turned him down when he invited me to dinner." Jennifer had a puzzled look on her face as Ben continued, "I had told him I couldn't make dinner because I was going to hire a sweet young thing and spend my evening fucking. He wants to hire you for tomorrow.

When does your friend get back in town?"

"Tuesday."

Ben buried his face between her breasts. "So I provide shelter for you tonight, Charlie'll take care of Saturday so you only will need to find two other clients to cover Sunday and Monday nights!"

"This guy Charlie, it's okay for me to feel safe around him?"

"I don't know anything about his sexual habits, but I do think of him as being pretty much a stand-up guy." He was nursing and tugging on her right nipple. "Do you want to book him?"

Ben's assault on her breasts was producing the desired result. Jenn reached for Ben's cock and as she lowered her head she smiled and said, "Sure, why not? After all, a whore's got to make a living, doesn't she?"

Ben's laugh quickly turned into a groan. He reached for the phone and dialed. "Hey Charlie, you're booked with Jennifer for tomorrow night. One thousand dollars and she'll fuck you blind. I'd let you talk to her but her mouth is otherwise occupied right now...I don't know, I'll ask her.

Hey Jenn, one of Charlie's buddies wants a wake up call from you at around nine a.m., interested?"

Jennifer never broke rhythm. "Tellm tobmook id."

Ben groaned. "What's the room number?" He hung up. "832 for your morning client and 716 that evening. I'll write it down." After writing down Jennifer's schedule he began going down on her, thrusting his tongue into her while his thumb started massaging her clit. She began to moan as she thrust her hips at his face. 

----

Jennifer woke at around 7 AM, crawled under the covers and started sucking Ben's cock to life.

"S'was goin' on? It's like dawn out!"

"I couldn't decide whether I should let you sleep in or if you wanted one more quickie before I get cleaned up and head out for Room 832."

Ben tousled her hair and kissed her lips. "I can't believe how lucky I got last night. I have no idea if you're going to keep this new career up, but talk about my being at the right place at the right time! You are, hands down, the best whore I've ever been with.

Let's fuck!"

Jenn smiled, "My kinda man!" 

----

Jennifer rang the buzzer on the suite that was room 832. She had showered, washed and blown dried her hair, and thought she looked pretty good considering the busy night she had just gone through. Her bag was totally filled with jeans and casual wear, so she was wearing the same dress she had worn to dinner with fresh panties and no bra. While she was waiting at the door she vowed to spend some of her earnings on a new outfit for that evening. If she was going to live the part of a high-class whore, she'd better dress the part!


Jennifer Tests Her Wings Ch. 02



Mrs. Lewis ran up to Jennifer as she got off the train and gave her a hug. "Jenn, it's so wonderful to see you! I was saying to Carrie only last week how much her father and I missed not having you around." 

Mr. Lewis also hugged her and picked up her bags and parcels. "I see somebody stopped in the City and did a little shopping on the way! Maybe I should say  a lot of shopping!"

Jenn laughed. "I know, I guess I went a little crazy but I love shopping in New York! It's like no other place on earth. Where's Carrie?"

Mrs. Lewis replied, "No other place to make you go broke! I can't control my spending when I get there either! I know what you went through.

And my daughter is making up your room. She said she'd do it before we left for the lake house, then she said she'd do it last night. When it was time to pile into the car I told her I wasn't having a guest show up to move into a dusty room with no fresh linens and an unmade bed!

I guess that's part of why I was so happy when I heard you were coming. I always hope that some of you is going to rub off on Carrie."

Jennifer smiled inwardly and wondered whether Mrs. L would feel the same way if she knew that she'd spent the last four days as a New York City prostitute!

"I can make up my own bed Mrs. L, I really don't want you going to all sorts of extra trouble on my account."

"Jennifer, a bed with clean sheets isn't extra trouble! It's simple common courtesy which isn't always so common around Carrie."

Jennifer decided to change the subject. "So how's Ray doing?" Carrie's older brother played baseball for the Yankees minor league affiliate in Tampa but was recuperating from arthroscopic surgery at his folk's house. 

"Playing the role of the wounded warrior to the hilt! He expects to be waited on hand and foot yet always seems to find the energy and strength to go into the City and party with friends of his!

I'm really glad you grew out of that crush you used to have on him or else he'd be recruiting you into his bevy of handmaidens. In addition to everyone in the family he's had two girls drive up on three different occasions to spend time 'nursing' him! He actually had one poor girl from Saddle River, New Jersey drive to Yankee Stadium to pick up a box of baseballs and deliver it to him here so he could play the role in front of some of the neighborhood kids.

He didn't want to go to the lake house with the family so he had a girl he knows from Tampa fly up to take care of him while we were upstate. We just dropped her at the airport this morning! That boy is turning into a spoiled...

Am I venting? I feel like I'm venting."

"Go ahead and vent! It's got to be healthy to let it all out once in a while." Jenn thought back to the days in middle school when she would have dropped to the ground and spread her legs any time Ray might have asked. She wasn't sure whether it was a good thing or a bad one that he never did ask her. It was certainly ego-deflating back then!

As soon as the car pulled into the driveway the front door of the Lewis house flew open and Carrie came charging out to meet it. Jenn had barely opened the car door when Carrie grabbed her hand and started spinning her around on the front lawn. The two girls were laughing about nothing in particular when Mrs. Lewis called "Anyone want to help with the luggage?"

Carrie ran to the back of the SUV and started grabbing bags. "Someone's been shopping. What'd you get me?"

Jenn replied, "A 19-year-old houseboy but his muscles wouldn't allow him to fit in those bags so I left him in Penn Station."

Carrie called over her shoulder "Mom...can I borrow the car for a couple of hours?

Ah never mind...some other greedy wench has probably scooped him up by now!"

Between the two of them they got Jenn's bags and packages into the guestroom. Carrie asked, "Alright if I open and peek?"

Jennifer plopped herself down on the bed. "Sure."

"What do we have here? Jennifer, how long have you been sporting easy access panties in your wardrobe? I thought you were more the cotton Haines type!" Carrie held up the black lace crotchless panties Jenn had bought a few days before.

"Is there a new 'special someone' our girl's decided to give it up for these days?"

Jenn took the lingerie from Carrie's hand. "No, there's no special someone! Haven't you ever bought anything just because they looked pretty and because they made you feel hot just wearing them?"

Carrie shook her head. "Sure, lots of times, but here's a news flash. Cotton Haines are more comfortable and shit like this is worn to be seen...by somebody, anybody!"

"Alright! The truth had to come out sometime! I've got it bad for you and thought I'd make my move tonight!"

Carrie continued to go through Jenn's bags. "That makes sense." She held up one of the new dresses. "Tell you what girl, you let me wear this once in a while and I might let you have your way with me."

"How about tonight?"

Carrie looked up. "What's up?"

"I sort of have a date tonight in the City if the two of us can swing it without offending your folks."

"Oh, so we did spend our time in Manhattan productively! Details, I need details!" 

Jenn sat on the chair by the window and said, "Well, I was having dinner at Del Frisco's and he picked me up!

We had dinner and we didn't wind up in the sack together, but I really wanted to." 

"Look you, don't you think you're carrying this 'virgin bride' motif to a bit of an extreme?"

Jennifer looked Carrie in the eye. "That will no longer be at issue."

Carrie clapped her hands. "Well all right! I would never have pushed the issue but I'm happy that that's taken care of. How long ago did that happen and how come you never told me?"

Jennifer said, "Four days ago and this is the first chance I've had. You were at the lake house, remember?"

"Four days ago...Friday...in the City? I don't get it, you said you didn't jump the guy we're seeing tonight!"

Jennifer sat on the bed and grabbed Carrie's hand. "I didn't, I met him at dinner on Saturday evening. I'd already been fucked by the other four guys before then!"

Carrie's jaw dropped. "Other four? Four? More than three and less than five kind of four? Different guys, as in four guys attached to four different cocks? What'd you bust your cherry at a gang bang?"

Jenn suppressed a mild chuckle. "Not really. I got to the City and my friend was out of town so I started shopping for a place to stay. All the hotels I could afford were completely booked. The City's hosting a Realtor's Convention.

So what kind of moderately attractive girl gets invited to stay in other people's midtown hotel rooms? Only one that I could think of, hookers. So I became one. I kind of excelled at it, too! The first guy referred me to the second, the second to a third, then the third to a pair of guys who wanted to tag-team me. The second guy, his name is Charlie, wound up hiring me for the rest of the weekend. He had me fuck a few of his clients.

I've actually had quite a busy weekend!"

Carrie was speechless. Jenn could tell she wanted to ask questions, but she looked like she couldn't think of them.

Jenn continued talking, "Now, should I tell this guy we're going to meet him tonight or should we spend the evening with your folks?"

Carrie looked at Jenn out of the corned of her eyes. "Do I get to wear the green dress?"

"You can wear whatever you want."

Carrie headed for the door. "I'll alert the parents." She paused at the door, "A hooker? How many clients did you...service this weekend?"

"Eight...well, nine if you count Nancy. Nancy's my boss' secretary and she gave me as a present to one of the firm's prospects. Nancy and this guy spent an afternoon enjoying me!

"Who woulda thunk it?"

Jenn continued unpacking her things both old and new and took her toiletries to the bathroom to grab a shower. After she dried herself she called Jimmy Leaback and arranged for him to meet them at Del Frisco's. She noticed that Carrie must have already come in and raided her closet as the green dress, a pair of Dior shoes, and the black crotch-less panties were gone.

Jennifer loved the looks on both Mr. Lewis' and Ray's faces when the two girls entered the kitchen. Since both the men were struck dumb when they made their entrance Jennifer knew they looked hot! Mrs. Lewis just made a mini-snorting sound while dicing some celery and said, "Some poor schnooks are in deep 'kimchi' tonight. I can't imagine many men capable of saying no to anything you girls want tonight!"

She continued working on the celery as she added, "Close your mouths guys!" --- On the train ride into New York Carrie grilled Jenn about every detail regarding her weekend and her new 'hobby'. Jenn's embarrassment quickly turned to enthusiasm as she gave Carrie what she laughingly called the "blow by blow" of her activities.

"So this guy we're meeting this evening wasn't one of your 'Johns'!"

Jenn laughed. "No, just a sports agent with the most dangerous blue eyes I've ever seen!"

"Are we expected to share him or is he bringing a friend for me?"

"Don't know. I'm kind of interested in finding out myself. I did kind of offer him the opportunity of being the target of both of us if that's what he wanted. We'll have to see how he plays it!"

When they got into Grand Central Carrie started toward the IRT subway entrance but Jennifer headed toward the side entrance where the most popular cabstand was. Carrie asked, "I thought you were Captain mass transit! How come the cab?"

"I love the subway but I sort of feel overdressed for it, don't you?"

"I'd always rather a cab but I usually defer to you."

When they entered the restaurant they were about to ask to be taken to Jimmy's table when Jenn saw him waiting at the bar.

Jimmy Leaback got up and made room for the girls at the bar. After they were seated Jimmy introduced them to a blonde man in his early twenties. As Jennifer shook his hand she said, "I'm delighted to meet you Don. I wasn't sure whether Jim was going to try to entertain the two of us himself or bring a friend."

Don Petrocelli replied, "That's not what he told me! He said he had met you the other night and that you were disappointed that he wasn't a newly brought up Yankee. He said we'd probably get along fine because you can't really get much newer than I am. I was called up last Thursday."

Conversation went well, both Jenn and Carrie nursed glasses of red wine, and Jenn thought that Carrie was really interested in Don...a lot!

Don was in the middle of a story as he said, "So the guy is convinced he might have almost killed the poor girl and he demands we take her to the Emergency Room right away."

At this point Carrie interrupted and said, "Oh, I know exactly what happened next!" Don smiled and said, "I'm inclined to doubt that, Carrie! You see nobody knows this story."

"Okay, let's bet on it! Whatever terms you want Don, I'm in!"

Don smiled. "Okay, if you don't know how that evening turned out you finish your meal topless. Just lower the top of your dress and continue eating."

Carrie shook her head. "Now Don, I never would have tried to embarrass you like that. Let's see now, okay I've got it! If I can correctly finish your story you have to reach under the table and masturbate yourself to completion before we leave the table."

"Done!"

"Done! So the girl, who was in on it from the start pretends to be unconscious and one of the other guys tells the pitcher to start mouth-to-mouth to keep her alive. They carry her to the car and the guy's still trying to help her breathe when the car pulls up to his girlfriend's house instead of the ER. They'd called her and she's at the curb as they pull up. The unconscious girl at this point has her arms around his neck and the girl sees her boyfriend apparently making out with this girl in the back seat. Was she ever pissed!"

The table was silent until Jimmy said, "I take it by Don's silence that Carrie won the bet! How did you know that?"

Carrie's eyes were still locked on Don's as she said. "Oh, did I mention when I was introduced as Carrie Lewis that I have a brother named Ray? He was driving the car."

Don's eyes were also locked with Carrie's as he reached under the table, unzipped his fly and was about to start masturbating when Carrie stopped him. "No Don, I really don't want to embarrass you and you never know, some bladder mouth reporter could be around."

She added with a smile, "Give me a little time, I'll come up with something else for you to do for losing the bet, something more interesting. On the other hand maybe I can blackmail you into playing some massively embarrassing gag on Ray. I'll think about it."

Jennifer dreaded whatever mischief Carrie might come up with if given a little time. Carrie was also starting to slur her words a little which might have something to do with the five glasses of wine she'd had.

Jimmy said, "I think a change of scenery is called for. Carrie if you like what you've been drinking this evening, I've got some '76 Mondovi Cabernet that you'll absolutely love!"

Jennifer thought it was a good idea to get Carrie out of a public place so she quickly agreed.

By the time the four of them got to Jimmy's penthouse Carrie had passed out. Don carried her in and put her gently put her on a bed in one of the guestrooms.

Jimmy put his arms around Jennifer and said to Don, "Well, since my major Cabernet fan is no longer in the market for wine, I think Jenn and I'll see you later, buddy." 

It seemed to Jenn that he was taking a lot for granted but Jenn allowed herself to be steered down the hall toward Jimmy's bedroom. They got to within a few yards of his door when he had unzipped her dress and was undoing her bra strap. It occurred to her that he hadn't even kissed her yet!

Once inside the door to his room Jimmy started undressing. Jenn assumed she was supposed to do the same. She was just stepping out of her panties when Jimmy came up behind her and started kissing her neck. She was starting to get excited as this was about to be the first sex she'd ever had that she wasn't being paid for. She figured that should make it more romantic somehow.

Jimmy positioned himself in a classic 69 position and began to nibble Jenn's outer lips while his tongue started exploring its way inward. In short order Jenn had completely devoured his cock and was deep throating him. As Jimmy's tongue continued its assault on her pussy his thumb found its way into her ass. Jenn groaned. 

The sound must have encouraged Jim as he immediately swung around as his cock started invading her ass. Jennifer immediately started pushing back against him as he grabbed her hips.

Around midnight Jenn awoke really thirsty and needing to pee. She got out of bed intent on a refrigerator raid. She didn't bother to dress as she assumed Don and Carrie would be asleep. Jenn knew the location of the powder room away from the bedrooms so she used that so as to not wake anyone. After pouring herself a glass of grapefruit juice she headed into the living room and plopped onto one of the sofas. As she looked around the darkened room her eyes lighted on a supine form on the other sofa across the coffee table from her. She recognized it as Donnie and his head was propped up on his hand as he stared at her.

Jenn said, "I thought I was alone! Don't tell me you guys had a fight already."

"No, no fight, but she's still passed out and I didn't want to take unfair advantage of her condition." He got up and draped a fleece blanket over Jenn's naked body. 

"Thanks. By the time I realized I wasn't alone I guess I just froze. It's kind of embarrassing." She snuggled into the blanket. "Froze both literally and figuratively!"

"That's okay, I'm a guy! Who better to see such a beautiful sight?"

Jenn chuckled. "Carrie's going to be a bit confused when she wakes up alone.

"I know. Truthfully I'm sure that if she'd been awake she'd have dragged me into bed with her but once she passed out the rules just changed, for me at least. So what do you do for a living?"

"Nothing. I'm just a high school senior working my way to graduation."

"Oh, Jimmy had indicated that you had had some sort of appointment which cut your evening short the time you guys met."

"I did, but it was at a west side hotel. I promised I'd sit with a friend who hadn't been well. He probably didn't absolutely need me, as it turned out, but I promised." "That's nice. Too many people play fast and loose with giving their word. So you've known Carrie for a long time, I take it?"

"Since she and I were five. When I was young I used to have a major crush on her brother, but Carrie and I were two sides of the same coin."

They talked until dawn and as Carrie stumbled out of the bedroom Jennifer felt a flash of jealousy. She'd been enjoying talking with Donnie and momentarily resented having to share him with anyone, especially another woman. She reflected that it was an odd way for someone who'd just fucked his friend to feel.

"Good Morning, do you feel as bad as you look?" Carrie rubbed her eyes. "Worse. Not only am I hung over, but I don't think I got laid last night!"

She looked at Don. "Did I?"

"Sorry, but you'd passed out in the cab."

Jennifer grabbed her purse, excused herself and went in to take a shower, but as soon as she shut the bathroom door her cell phone began demanding her attention. She answered it and the call was from Charlie. The sound of his voice put an immediate smile on her face.

"Charlie! What's up, dude?"

"How was your reunion with Carrie?"

"Oh I guess it took about nine seconds for us to fall into our old comfort range. We're in the city now, having partied a little to excess last night."

"Did you tell Carrie about your debauched weekend?"

"You mean my life as a call girl? For sure! That's just the sort of thing we couldn't possibly keep secret from each other. Why?"

"Well if you don't have anything planned for today I was hoping to hire both of you for the afternoon. I'm in meetings with this guy who could represent the biggest deal I've ever put together. We're breaking for lunch at about one and I'm having it catered here at the hotel. I thought the two of you might make a great desert, that is if Carrie's interested."

"What about finding out if I'm interested?"

Charlie laughed. "I already knew you'd be up for it. You love the entire concept of being a whore. Look, I know you'll want to talk it over with her and I don't feel like hiring anyone else but you girls so let me know whenever."

Charlie paused and then said, "I probably shouldn't be saying this but even though we fucked yesterday morning I've kind of missed you."

Jenn was grinning as she replied, "Maybe because what we did yesterday was quite a bit more than just fucking. You have no idea how your call turned a plain face into a smiling face." She hung up.

She called to Carrie. "Hey Wench! Either shower with me or just after me, but we've got to get going!"

Carrie let herself into the bathroom and started to undress. "Is something up or are you making that pass at me?" She climbed into the shower with Jennifer and started soaping her back.

"Want to earn some fast cash?"

"Charlie called."

"Right; he just called and wants us to be the desert at a luncheon he's having for a client."

Carrie hesitated. "Okay if you want me to, but I'd be doing if as a favor for you. I don't need the cash and I've never fucked an old guy before."

Jenn turned around and took the soap. "What about teachers, don't they count?" 

"Well I knew them! They couldn't possibly count."

"Look, I have absolutely no desire to talk you into anything you're uncomfortable with, especially something illegal! I just thought it might be fun if the two of us took on two guys together."




Jennifer Tests Her Wings Ch. 02



"Absolutely! I think that part's yummy but in my fantasies they'd be under twenty-five not over one hundred.

Whatever, color me in 'cause I'm looking forward to group sex with you on the periphery rather than being my main target. I might feel funny about that."

Jennifer gave Carrie a quick peck on the cheek and stepped out of the shower to call Charlie. "We're in! Do I get to fuck you or the other guy?"

"I can't think of anything but getting my hands on your body but since you're the proven professional it makes sense for the client to get the best I have to offer.

Who knows, maybe I'll get to like Carrie better than you!"

Jennifer shrugged her shoulders. "Maybe, but if you do, I'll get out my pruning shears and make some anatomical changes on your body, Daddy of mine!"

"Point made!"

After hanging up the call Jenn toweled off and put the dress she had worn the previous evening back on. She heard Carrie turn the water off. Jenn said, we'll have to stop somewhere and pick up some clothes."

"You used to be little Miss Organized!"

"I don't know what that means but I did pack a change of underwear for each of us in my purse."

Jennifer sighed. She sort of expected Carrie to be more enthusiastic about her little hobby and was uncomfortable with the idea that she was pressuring her friend. "If you don't want to do this you'd tell me right?"

Carrie put her arm around her friend. "Okay, Mom! Stop worrying; I'm a big girl, okay?"

Donnie was disappointed that the girls had to run but he made sure to get their numbers before kissing them goodbye. Jimmy was still asleep.

They stopped at the same boutique Jenn had found that weekend and each got an outfit for lunch. Jenn looked Carrie over. "Bitch, you have no idea how hot you look right now."

"You don't look so bad yourself!" They got to the hotel and took the elevator to Charlie's suite. Jenn said, "Okay, all you need to do is be yourself. You're the answer to any man's wet dream."

Carrie looked tense. She just said, "I know."

Jennifer read it all in the look on Charlie's face. When she introduced Carrie to him his eyes temporarily basked in her good looks and slid over to her. He wanted her really badly and his lust ignited a heat in between her legs.

Jennifer said, "It's really great to see you again Charlie!"

Charlie leaned over as if to kiss Jennifer's cheek. He said in a voice barely above a whisper, "Change of plans. Let him pick."

Jennifer took Carrie by the arm as Charley led them over to the client, "I said they were lovely didn't I! Dessert is served. "Brad, this is Jennifer and this is her lovely friend Carrie."

Each girl gave Brad a peck on his cheek. He said, "Wine? It's a rather nice Cabernet."

Carrie had picked up on the heat being generated between Charlie and Jenn so she took the offensive with Brad, dropping to her knees in front of him. "Mind if I use the wine as a chaser?"

"Not at all, Sweetheart, not at all!"

"Excuse us, Brad. We'll leave you to your little party."

As soon as they entered the bedroom Charlie pulled Jennifer onto one of the king sized beds. They lay on their sides facing each other as he gentle stroked her arm and placed a series of light kisses on every part of her face. "I can't begin to tell you how pleased I am that Carrie took Brad out of the running for a place in your bed."

Jennifer started loosening Charlie's tie. "I'll have to thank her for that."

Jennifer took off her jacket and started unbuttoning Charlie's shirt. He was making her work slow going as he was intent on rolling down her hose ever so slowly, inch by inch, with his tongue. She finally gave up on the shirt and pushed down his slacks and underwear to gain access to his wonderful semi-hard cock. While Charlie was paying careful attention to bathing each of her toes, one by one, Jennifer was gently stroking and kissing her way around her favorite toy.

At this point Brad and Carrie came into the room. Carrie said, "Okay if we take over the other bed? I'd like to fuck before an audience even if they're otherwise engaged.

Jenn simply nodded. Carrie asked Brad, "Is she saying that it's okay or just ignoring us and continuing to give head?" Brad shrugged his shoulders and pushed her to her knees on the bed. 

Jennifer thought she'd resent the company but then noticed her pussy begin to get much wetter as she viewed Brad driving his cock into the doggie-positioned girl. She winked toward Carrie but it wasn't noticed. The scene wasn't lost on Charlie either as he flipped onto his back and grabbed Jennifer's hips to position her for his entry. Jenn pulled off her bra which was the last remaining article of clothing worn by them. She grabbed Charlie's cock and slid in into her wet passage.

Jennifer looked at the couple next to her and wished Carrie would take a break so Jenn could have both cocks in her at the same time. She definitely was going to call Donnie later that day. She was becoming obsessed with having every man who crossed her path.

Charlie's sperm shooting into her brought her mind back to more current affairs. She flopped down onto him and as he showered kisses on her breasts she held and hissed the top of his head. Jenn's erect nipples were being nibbled and tugged and the feeling was causing her to start climbing the walls again. He positioned himself between her legs and slid his hands under her, tightly grasping her butt cheeks as he rubbed her wetness and nibbled her clit with his teeth. As soon as his tongue started rubbing her clit she exploded. Jenn screamed right up to when Brad's cock entered her mouth.

She opened her eyes to see his large cock in her mouth while Charlie continued to eat her pussy. She couldn't see Carrie but from Charlie's body language she must have been on the floor with Charlie's cock in her mouth. She twisted to see and could just make out Carrie's feet on the carpet protruding from the end of the bed. 

The cumulative effects from getting his dick sucked finally got to Charlie and he slid down onto the floor and started to fuck Carrie. Jennifer could hear the two of them and was embarrassed that she again felt jealous that a dick was fucking someone other than herself. Brad flipped Jenn over and pulled her hips up so he could enter her ass.

Jennifer must have dozed off after the sex because she began to awaked when she felt Carrie's lips tugging at Jenn's nipple. She looked to either side and found herself and Carrie in the middle of a hero sandwich with Charlie behind her and Brad behind Carrie. Brad had Carrie's breast in his comatose hand.

Jenn kissed Carrie's forehead. "That was fun!"

Carrie said, "Mmmm!" She then took her lips from Jenn's nipple and silently mouthed, "Can we go home now?"

Jenn kissed her shoulder. "Sure. Let's shower."

In the cab from the hotel to Grand Central Jenn gave Carrie her half of the fourteen hundred dollars Charlie'd given her. Carrie looked at for a second and gave it back. "No thanks, I was just doing it to help you out."

"I'm not keeping it. I'm not pimping you out!" They emerged from the cab and as Jenn paid the driver she saw Carrie out of the corner of her eye put the cash in a Salvation Army kettle.

The train ride up the Hudson River was unusually quiet. Jenn finally broke the silence. "I'm sorry."

"Me too, who'd have thought I'd be the one to get preachy? Look kiddo, except for three guys in Binghamton or some such place I've probably fucked seventy five percent of all the guys in New York State between the ages of sixteen and twenty five, but it was always just for fun. Some day I'm going to be married and living in a Tudor in Irvington with three dogs and two kids. The height of my rebelliousness will probably be if I'm socially irresponsible and have more kids than dogs. I'm probably going to run into guys who once had a quickie with me in the park or in a men's room somewhere. It might be embarrassing but I'll get over it. I don't mind being remembered as the tramp party girl from North Tarrytown because that's what I like being now. I'll pass on being recognized as the hooker from Manhattan though."

Jennifer put up the seat divider and swung her jeans covered legs onto Carrie's lap. "I was still a virgin on the train up from Washington and I'm not even vaguely regretting my solution to my New York housing problem. I did what I needed to do to resolve my situation without admitting failure to my Dad. Tonight was kind of unnecessary. I wish I hadn't involved you in it but then again maybe I'm not.

You see, I know why this evening happened. It wasn't that I was excited for a foursome with you, although that was really nice!" Jenn looked into Carrie's eyes and sighed.

"It's just that I feel that hooking is somehow more responsible than admitting that I'm hung up on a fifty-eight year old guy."

"I wondered if that might be it.

That's why I stepped in to take the decision out of Brad's hands. The looks in both your eyes told that tale.

Not to sound ridiculous but let's ask Beverly! She'll give us an objective common sense answer."

"Your Mom?"

"Don't sell her short. She's pretty smart and gives honest answers. If fucking Charlie is good for you, she'll tell you why! If it's not, she'll tell you if you're making a fool of yourself."

"I think I already know what she'd say, Carrie! No parent is going to get excited about the prospect of a girl matched up with a guy more than triple her age!"

"If that's true, all you've done is waste a little of your time, right? Or do you think she'd rat you out to your parents?"

"No, I don't think that. It's just that I don't want her thinking of me as being a silly teenager." Carrie snorted. "She already thinks you walk on water. Maybe now she'll just think you're normal!"

Beverly Lewis was making dinner when the girls came into the kitchen. Carrie started with "Mom, I'm sorry I didn't call, but we got so..." Beverly interrupted her daughter. "Don't get yourself in too deep. Jenn already called last night and said you'd be home for dinner tonight.

The two of you should co-ordinate your stories."

Carrie's eyes were glaring at Jennifer for not letting her know about the call as she continued talking to her mother. "Anyway, Jennifer wants to ask you a question."

Jennifer glared back. "Carrie, can't you see now's not the best time? Maybe later, Mrs. L."

Mrs. Lewis dried her hands and turned to face Jennifer. "The roast is in the oven, everything else is pretty much on autopilot. I was about to have a beer, want to join me?"

As Jennifer smiled back Mrs. Lewis went to the refrigerator. "Carrie?"

"Sure Mom, make it a Coors Light."

"Three coming up. Why don't we go into the TV room to drink and talk?" They all flopped into the overstuffed sofas in the home theater room.

"So how can I help you, Jenn?"

"I'm sorry. This was all Carrie's idea. I really think I'm past helping."

"Good! That's one problem I don't have to deal with!" She took a swallow of beer. "Since I don't have to soothe the aches of the world let's just talk girl talk.

How've you been, Jennifer?"

Jenn chuckled and shrugged her shoulders. "Not too bad, Mrs. L. Not too bad considering I'm in love with a man my folks would never approve of!"

"Are you sure?"

"Pretty sure. He makes me laugh. He always treats me with respect and listens when I go off on tangents. He's really bright and a hard worker. He owns his own business and makes good money."

"The nerve of the man! String him up!

On the other hand..." Beverly took a good pull on her bottle. "On the other hand maybe he sounds a little too good to be true. How old is he, forty?"

"Fifty-eight."

"Oh yeah, that'd ring your father's bell! I take it you're sleeping with him?" Jenn nodded. "And you're using appropriate protection?"

Jenn tilted her head to one side. "Usually."

Beverly sighed. "Usually might help a little with unwanted pregnancies but it doesn't mean jack if you catch some STD. How long have you active with him?"

"I just met him Friday night."

Beverly rolled on her side and rested her head on the arm of the sofa. "I don't get it. You meet him on Friday, fall for him and then jump on a train to come up here?"

Jenn looked at Carrie, who responded to her look, "Hey girl, don't look at me! It's your story and if you don't want to go on that's your business but just so you know, I tell my Mom just about everything. If you want me to leave out certain parts of last night I will, but she'll know I only did so 'cause I love you."

Jennifer lowered her eyes to her lap and took the plunge. She started by explaining her mistake in scheduling and didn't stop recounting the details of her weekend until this morning when Carrie dropped the cash in the Salvation Army Kettle.

Beverly's eyes looked at her daughter with obvious pride. She swung her feet to the floor and said to Jennifer, "I'm not sure if that rates being called determination, I'm more inclined to call it male pattern stubbornness on your part!

I'm empty. Anyone else need a refill?" Both girls answered yes although Jenn's bottle was still half full. She chugged it down.

When Beverly gave Jenn her fresh beer she leaned down and kissed her forehead. "The fact that Charlie's up here gives you a little more time to work it out but you said he was in town for a convention?"

"He extended 'til Thursday...so he could see more of me."

"So are you content unloading on me or do you want suggestions?"

"I'd really appreciate any help you could give me."

Beverly stared at Jennifer and wasn't about to speak until Jenn looked up from her lap. After they had made eye contact Beverly said, "Stop taking his money and if you can bring yourself to do it, give back every dime he's ever paid you. You don't want to let a man have an easy excuse to ever disrespect you.

It sounds like you made enough from your other clients to cover what you spent on clothes. If you're short I'll make up whatever shortfall you have.

I'll try to get you an appointment with Carrie's doctor for today. You need an examination and a prescription for the pill. If you're going to ignore the disease implications of what you're doing, at least we can try to keep you from adding to the teen pregnancy stats.

Kiddo you're a bright girl. I don't have to tell you how severely the odds are stacked against you guys lasting, but so what? My first love didn't make it to its first anniversary but if I could, I'd relive it a few times. We screwed our brains out and were absolutely convinced that everything else in the world was secondary to how we felt about each other. Enjoy it; enjoy him but remember that whatever happens to the two of you, you'll always close your days in bed with yourself. Try to do as few things as possible which make you like yourself any less."

Beverly arose from the sofa. "We like you; we love you and I've got to duck out to tend our dinner. I'll be gone less than three minutes, I promise!"

Carrie looked like she was glowing. "Is my Mom totally cool or what?"

Jenn smiled at her. "I've always known that. I just never knew you did.

So what do you think, is there something potentially brewing between you and Donnie?"

"I hope so! In the restaurant I thought there was but this morning I thought he might be all over you."

"Yeah but in all fairness we wound up talking half the night away. I was fresh in his mind and I'm not sure I know how to talk to a guy without flirting. The more interesting question is how Sam's going to react if you guys start seeing a lot of each other."

"What do you mean? Why would Sam care one way or another?"

"Maybe he wouldn't but up to now baseball's always been his exclusive club and all the rest of us have always been outsiders. Remember when you won that bet with Donnie at the dinner table? You won because you had knowledge only possessed by insiders. Well that knife cuts both ways. If you and Donnie become a thing you'll have a pipeline for knowledge about Sam!"

Mrs. Lewis walked back into the room. "Did I miss anything?"

Jennifer replied, "Nothing interesting. The conversation had switched to your daughter's love life and even though she might be interested in the guy she was with last night, since nothing happened there are no juicy details."

"Why didn't anything happen? Did he drink himself senseless?"

"No, she did and he's got scruples."

"My daughter was out with a nice guy instead of a letch? Unheard of!"

"You know I think you and my parents paint her with a brush she usually doesn't deserve."

Beverly grinned like a Cheshire cat. "I know, but we're parents. We have that right. Your mother and I've had quite a few conversations about you guys over the years. She knows she was half trying to keep you as her little girl. She'd get afraid that being around Carrie would make you grow up too fast."

Jenn's Blackberry began demanding her attention. When she looked at the screen she said, "It's Charlie.

Hi!...Mmm, me too...I don't know, Charlie, I just got back and I feel like relaxing and spending an evening with bare feet." She laughed at something he said. "No, I meant with clothes on!"

Beverly cut in. "Miss my roast and you're dead, Reynolds! Why don't you invite him here for dinner? Maybe he'd like a home cooked meal he could eat with his shoes off!"

"You've just been invited to dinner...Why not, Carrie's mom's a great cook!...Just three hot women, Carrie's Dad and brother are off doing something manly...Really? Cool...Just head over to Grand Central and grab the first Hudson River train you can and head for Tarrytown...I'll pick you up at the station..."

Beverly called over to her from the kitchen. "Tell him to pack an overnight bag!"

"You're supposed to bring an overnight bag...I doubt it, but you never know!...Oh, and Charlie?...I'll come to the station in my shortest skirt and I won't be wearing any panties." She hung up.

Jenn and Carrie were giggling when Beverly came in from the kitchen carrying a plastic grocery bag. She handed it to Jenn and started back for the kitchen, saying only, "Stanton Lane." Jenn opened the bag and found it contained a container of Lysol wipes and three condoms.

"What's Stanton Lane?"

The voice drifted back. "The closest road to the train station where you can get it on with any degree of privacy.

And don't leave my car smelling like a brothel!"

Jenn took the condoms and bounced over to the kitchen door. "Three? I believe I told you he's fifty-eight!"

Beverly continued stirring the pot. "You never know! Love sometimes overrides the calendar!"

Jenn started walking back to the living room calling over her shoulder, "You're right, you'd better get me two more!" ///\\\ Jenn had raided Carrie's closet and had come up with a great outfit for the drive to the station. She found a brimmed black Danish seaman's cap which could double as a chauffer's cap in a pinch and a white pleated micro-mini skirt that covered her ass, barely. What made the outfit, however, was a tuxedo jacket Sam had rented in middle school then claimed to have lost. His parents wound up paying for it before the jacket turned up months later. When Jennifer buttoned the jacket it covered her breasts but left no doubt that there was nothing underneath it. Carrie took a large piece of poster paper and printed T A Y L O R in large block letters. When Jenn held it in front of her it concealed the more indecent aspects of her outfit.

Charlie spotted her as soon as he alighted from the train; as did all the other passengers. A man about thirty walked up to her and asked, "Can I be Taylor?" Charlie saved her from having to come up with an answer when he said, "I'm Charlie Taylor."




Jennifer Tests Her Wings Ch. 02



As soon as they got into the car Charlie was all over her. Jenn was finally able to gasp, "Let's go somewhere more private."

Jenn drove out of the parking lot and pointed the car toward Stanton Lane. As she was driving she reached into her purse and withdrew a fat, manila envelope which she handed to Charlie saying, "First things first."

"What's this?"

"Open it."

Charlie opened the envelope to reveal seven thousand dollars. Jenn continued, "That's every dime you ever gave me."

Jenn took her eyes from the road to take in his puzzled expression. "I don't want to be your whore anymore Charlie.

Don't get me wrong. I still want to jump your bones, suck on your cock, and fuck you 'til your eyes bleed, but I want to do it 'cause I want to, not because I'm being paid to."

Not getting a response, Jenn looked over at Charlie. He just said, "Please hurry; I don't know how much longer I can wait to kiss you."

Jenn saw a building site with a mostly finished home. She pulled the car behind it and grabbed a lap blanket from the rear seat. "Let's go."

As they walked the thirty yards to the house Charlie had his arm around Jenn's shoulders and his hand inside her jacket cupping her breast. They spread the blanket on the floor of what would soon be someone's living room as Charlie was showering Jenn with kisses.

Jenn unbuckled his belt and pushed his pants down. She really enjoyed Charlie's cock. Her tongue circled the head as she alternated between sucking it and kissing it. She could feel Charlie pulling her hips around so he could start working her pussy. As soon as his lips touched her and he realized how wet she was he inserted his thumb into her pussy while his tongue worked her clit. She quickly began moaning and twisting her hips in pleasure.

Charlie responded by inserting his other fingers to lubricate them. Suddenly Jennifer felt like a bowling ball with Charlie's thumb in her pussy and his index and middle fingers in her ass while his tongue and teeth were working on her clit. With his cock squirting down her throat she found she couldn't scream but she moaned as her cum drenched Charlie's face.

Jenn kissed Charlie's nose. "I'm sorry. I just want to lay here with you for the next several hours but if we don't get cleaned up and out of here we'll be late for dinner!"

Beverly opened the front door when Jenn rang the bell. She looked a bit surprised by Jennifer's chauffer's uniform. "Mister Taylor? Hi, I'm Beverly Lewis, won't you come in? I suppose your driver can come in too!

Interesting outfit, Jennifer."

Charlie shook her hand and shook his head saying, "It's rather hard getting good help these days."

"If she always dresses like that I can see why things might frequently be hard. Carrie's tending bar. Can she fix you a drink?"

"A scotch and water would be perfect!"

Dinner went well. The food was delicious, the conversation witty and Charlie's hand frequently found its way into Jenn's lap and under her skirt. She began to fear staining the fabric of her chair so she snuck her napkin into her lap and under her leaking pussy.

When the meal was done Jenn got up and was helping Beverly clear. As Jenn walked past her, Beverly said, "I like him. He obviously likes you so I'll stick up for you when your Dad tries to lower the boom.

And Jenn, don't be disappointed but your father's really not going to like the whole situation.

Jennifer sighed. "Yeah, I know."



Jennifer Tests Her Wings Ch. 03



Please Note! This story might possibly be read as a standalone but it's infinitely more enjoyable if you go back and start with Chapter 1

*

Jennifer kissed Charlie's lips. She realized that she hadn't the energy for much else at that point. She'd been having sex with him for close to forty-five minutes and it pleased her that Charlie was still going strong when she decided she'd had enough. Fifty-eight years old and still capable of the occasional marathon mixed in with the Wham, bam, thank you Ma'ams. She decided it was like ice cream; occasionally awesome but always better than lima beans. She thought to herself, "What a great idea!"

Beverly was straightening up the kitchen at 2 A.M. when Jenn ran in naked. Jenn looked as surprised as was her hostess as she murmured, "Oops!"

Beverly said, "If you're here for chocolate syrup, you're washing the bed linens tomorrow!"

Jennifer laughed. "Actually I had this incredible urge for ice cream! Charlie's is always 98.6!"

"Eat the ice cream off his scrotum and he'll come back to life!"

"Is that true?"

"I have absolutely no idea but it might be fun finding out!"

Jenn grabbed the cleanser and started on one of the pots in the sink. "Do you always clean up at two in the morning?"

"I'd rather not face it in the morning and it won't take all that long." She took the pot from Jenn's hands and continued cleaning.

Jenn got some Cherry Garcia from the freezer and put some in a bowl. She was about to put the ice cream container back when Beverly said, "You'd better add another scoop. You've got a lot of mouths to feed."

Jenn looked puzzled and Beverly added, "I heard the telltale squeak from Carrie's door. While you're in here talking to me I suspect she's in your room. I think it's time we discovered whether she's being supremely rude or not."

When they opened the door to Jenn's room they beheld a nude Carrie sitting astride Charlie's back with a bottle of oil at her side giving Charlie a deep tissue massage. Carrie looked over her shoulder and said to Beverly, "Before you say anything Mother, don't forget yesterday's lecture about amenities and going 'that extra mile' to make our guests comfortable. As Jenn was otherwise occupied talking to you, I thought I'd extend our guest some of those amenities."

Beverly answered, "I like your interpretation of common courtesies. Please don't extend them to Uncle Walter when he comes to visit next month. I don't think his heart can stand it!"

Jenn walked over to the foot of the bed and asked Carrie, "While you're being so courteous would you mind flipping Charlie over onto his back so your mother and I can perform a scientific experiment?"

Charlie spoke up at that point. "There aren't any knives involved with this experiment are there?"

Jenn laughed. "No, Charlie, no knives. You go ahead and enjoy your massage. I assure you that nothing Beverly and I will do will cause you to sustain any permanent injury!"

"Okay, but I'm still not sure I like the sound of that."

The two women knelt at the foot of the bed and pulled on Charlie's legs so his ass was right on the edge of the mattress. Beverly spread Charlie's legs and lifted his package as she said to Jennifer, "Now put the bowl tightly under his scrotum wedged between his thighs."

Jenn did so and Beverly released his privates so they were resting atop the bowl of ice cream. She let the semi-limp penis fall to one side.

"This is exciting! I always wanted to test this theory but Carrie's Dad would never allow me use him as a test subject." As Jenn put her face into the bowl and began licking the Cherry Garcia, Beverly took an iced tea spoon she had brought and began ladling some of the melted ice cream all over Charlie's sack. Jenn kept licking.

A voice was heard from the bed's pillow area. "Hey, that's cold!"

"Shut up, Mister Taylor! What Jenn's doing is for the advancement of science!"

Beverly took a spoonful of the ice cream and rubbed it against each of Charlie's balls before eating it. "Jenn, Charlie's balls don't add any flavor to the ice cream, make a note of it!"

Jenn couldn't reply all that well as she was sucking a testicle into her ice cream filled mouth. But at that point Charlie said, "I couldn't help but notice that you're the only clothed member of our company, Beverly. You're more than welcome to join me and let these two minister to you as well."

"Thanks ever so much for the offer but I've never done anything I wouldn't feel comfortable telling Carrie's father about and I think this would probably fall into that category." She started to leave the room saying, "Good night, all!

Oh and Jennifer, the experiment worked!" 

Jennifer laughed as she beheld Charlie's rock-hard cock. "Yeah, I know."

Charlie asked, "Jenn, would it be all right if I ate Carrie's delicious looking pussy?"

"Shouldn't you be asking Carrie that question?"

"Jennifer, I'm not stupid! I'm asking the correct person."

Jenn had gotten on the bed and was lowering herself onto Charlie's pole. She chuckled, "Sure, Charlie, be her guest!"

Carrie interrupted at that point. "If anyone cares it's okay with me on one condition.

Charlie would you do me a favor and cum anywhere other than inside of Jenn? She'll be on the pill by tomorrow but she's been playing Russian-roulette up to now."

Charlie looked shocked. He looked Jenn in the eye with complete incredulity as he said, "Of course, you're unprotected! You were a virgin prior to Ben. Jennifer, why didn't you remind me?"

Jenn looked sheepish. "We were having such a good time I was afraid it would detract from the sex."

"Carrie, would you mind changing places with Jennifer? I want to make out with my brain-dead girlfriend."

"Sure! Cowgirl Carrie reporting for duty." She grabbed Charlie's cock and after moistening the head with her pussy's juices began to ride him. Jennifer snuggled up against him and played with his nipple with her tongue.

She asked, "I'm not going to get laid, am I?"

"You don't deserve to get laid." He pulled her up and kissed her eyes.

It wasn't long before Charlie began to become increasingly involved with fucking Carrie. It seemed like when he had kissed Jenn a very few minutes before she was the center of his universe but, like sand through an hourglass, she could feel herself slide to the periphery. As Carrie slammed herself into his pubic bone she leaned forward grabbing his shoulders and digging her nails into his flesh as her breasts bounced over him. It surprised Jenn that she wasn't feeling jealous but she supposed she was still basking in Charlie's referring to her as his girlfriend earlier. She wanted to be as low profile as possible since the subject of protection with all the other men she'd had sex with hadn't come up yet and she didn't want it brought up!

Carrie woke up around 6:30 and slid out of bed to wander back to her own room. She was half-way down the hall when she heard sounds coming from the kitchen so she grabbed a robe from her closet and headed for the coffee.

She got within a few feet of the kitchen door when she smelled the potatoes and onions browning on the range. "Mmm, smells like a big country breakfast in the works. We must consider Charlie company since Jenn's enough like family that she probably wouldn't rate the full spread! Blueberry pancakes too?"

Beverly responded. "Yes, and that should tell you that I was going to fix them for Jenn anyway. I went to the market before I knew Charlie was going to join us and try to have sex with every female in the house."

Carrie opened the door to the microwave. "This batch looks about done, should I put in another batch?"

"Please; and there's two pounds of bacon there and we might as well do it all. What we don't have with breakfast we can raid for BLTs later. Besides, I'm sure your father and Sam are going to be looking for sandwiches when they get home later this afternoon."

Carrie said, "Okay; by the way, last night was a FWO, right?"

"Definitely it's for women only! Your father wouldn't approve of Jenn and Charlie, and even if he accepted it he really wouldn't approve of you having sex with Jenn's new boyfriend! I'm not even sure I'm all that crazy about it!

Carrie, you had no way of knowing how she'd react to your being in bed with him!"

Carrie tilted her head while considering. "Actually, yes I did. At least I knew how she wanted to react, how she thought she should react.

She's still trying to get her head right after having been Charlie's hired whore."

Beverly shook her head. "That whole episode still frightens me to death! Do you have any idea how many girls in that profession are beaten and killed every year?

Besides, that was as much your fault as Jenn's. As soon as you found out about her problem you should have let me know! I could have called Loraine Hollenbeck and Jenn could have stayed at her apartment on Central Park West!

Instead she winds up having unprotected sex with strangers to put a roof over her head! Let's change the subject. I just heard the shower turn off. Someone else will probably be joining us soon."

Carrie was setting the table when Jenn came into the kitchen dressed in jeans and shirt. Her feet were still bare. Jenn greeted Beverly, "Good morning. Everything smells yummy, what can I do to help?"

"Juice, you can put the juice out. There's orange and grapefruit already poured in pitchers in the fridge. I've also got V-8 if anyone prefers.

How does Charlie like his eggs?"

Jennifer giggled. "I have no idea, I'll go check."

Jenn had barely disappeared down the hall when the front door burst open and Mr. Lewis came into the house. He sniffed the smell wafting from the kitchen and called over his shoulder, "I told you we'd make it in time for breakfast!" 

Carrie ran up to her father and hugged him. "Welcome home, Pops."

"Hi Honey, what's for breakfast?"

They walked arm in arm toward the kitchen. "Mom made the A breakfast. I'll set two more places."

"Better make it three; Ray brought a friend along from the team." He looked at the table. "You've already laid out for four! Who else is here?"

Carrie's face went white when she remembered Charlie was still here. She was about to answer her father when a voice came from down the hall, shouting, "Charlie takes his eggs up just like me and he asked for three. I guess Carrie and I wore his ass out last night and he needs to restock his protein. He said he..."

Jennifer came around the corner and was silenced by the sight of Mr. Lewis standing in front of Ray and Don Petrocelli. All three looked temporarily frozen until Donnie took the lead and walked up to Jennifer. He hugged her, kissed her cheek and said, "Hey Jenn, you look great this morning.

We've been up all night and went fishing at dawn. We only caught one little trout which we released so we're all starving!"

Jenn still couldn't get her mouth to work but fortunately at that point Beverly came in with one serving platter filled with pancakes and another loaded with home fries.

"Jenn, I thought you were putting the juice out! Get your butt moving!"

Jenn was shocked into action and went for the kitchen. "Right away, Mrs. L."

Carrie gave Donnie a peck on his cheek saying, "I already know how my Dad and Ray take their eggs and now we all know how Charlie likes them so that leaves you."

Donnie squeezed Carrie's waist, "Over easy, also three if there's enough."

Ray asked the unasked question. "Who's Charlie?"

Carrie answered, "A friend of Jenn's who trained up from the City last night for dinner."

Mister Lewis went over to the air pot which was set up on the kitchen pass-through and started filling coffee mugs. "Sam, you take over here, son. I'd better make another pot." 

Beverly brought out a plate of toast, English muffins and croissants. "Please! Everyone whose name isn't Beverly or Jennifer please sit over. Food's starting to get cold and it's not that big a kitchen!"

Mr. Lewis sat at the head of the table and the scowl he'd sneaked at Carrie was nothing compared with the look his face donned when Charlie entered the room clad in a white shirt, grey slacks and a blue Annapolis blazer.

He reacted from habit and shook the hand extended to him as Charlie said, "Nice to meet you Mr. Lewis, Ray, so good to meet you. Rough break about the shoulder but the papers said the surgery went well. How does it feel?"

Ray took his turn shaking hands and responded, "Pretty good. Rehab's a pain but my motion is getting better every day."

Charlie held his hand out to Donnie. "Donnie P! I got to watch you play 24 games for the River Dogs before they sent you to Wilkes-Barre.

I only caught three games there but now that you're with the big club I guess I'll have to figure out how to take more meetings in New York!"

Donnie responded, "Twenty four games; are you from the Charleston area?"

"No, Birmingham, Alabama, but I love good defense and believe me you've got quite a few Gold Gloves in your future. And you can ask Jenn, I don't believe in empty flattery!"

Charlie took over the table. Beverly could see her husband's anger diminishing as Charlie paid homage to Ray and Don. Beverly smiled to herself thinking "The way to a man's heart is to heap praise on his son!"

As Charlie spun his Svengali's web around the men, even Jennifer relaxed enough to occasionally stroke his arm, basking in the reflected glory.

Ray had an appointment with a Doctor in White Plains and didn't have to go to the ballpark, so Carrie volunteered to drive Charlie and Don back into the City. As Charlie and the girls drove off Mr. Lewis started clearing some plates from the table. When he started putting them in the dishwasher he turned to Beverly. "He's almost as old as my Dad!"

Beverly continued scrubbing pans as she smiled, "Just about!"

"And please tell me I misunderstood it when Jennifer said that she and your daughter 'wore his ass out!'"

"No, she meant exactly what you thought she meant!"

"And you're not upset? This is all okay with you?"

Beverly sighed, "Oh maybe a little, at first, but someday when we're snuggling in bed I'll give you the whole story and I think you'll be just as proud of 'my daughter' as I am of yours.

Oh she's wild alright, but she's really a rather together young lady. I know I wish I had a friend like her when I was a teenager!

And yes, Jenn's finally acting like a teenager who just got sex as a present under her tree, but she'll grow up!"

Jack Lewis sighed, "I guess I'm getting old."

Beverly put her arms around him from behind. "No, you're being a Dad and you're a very good one!" She moved around so she was facing him. "Want me to demonstrate what the girls were doing to Charlie last night? I'm not wearing any panties."

"Ray's around!"

"Don't be dirty! He does fine finding his own girls! Besides, he's in his room texting everyone he knows."

Beverly sank to her knees and opened Jack's fly. She almost got his cock into her mouth when Jack grabbed her wrist and threw her over his shoulder in a fireman's carry. "We're going to screw on our bed with the door closed! I'm not going to try to get off worried whether my son is going to surprise us in the act!"

He threw Beverly down on the bed and finished removing his clothes. She had just rid herself of her jeans and panties when Jack came up in front of her and literally ripped the bra from her shoulders, pulling her to her feet as he did so. She wrapped herself about him and thrust her tongue deeply into his mouth as her nails raked his back. She pushed him down on his back on the bed and dropped to her knees between his legs.

"Jennifer kneeled here and grabbed his cock as she held a bowl of Cherry Garcia ice cream under his scrotum. She alternated licking the ice cream with taking each ball into her mouth."

Jack was clutching at the comforter, his erection hard as stone. "Oh she did, did she?"

"Then she put the bowl aside as she deep throated his cock with three long strokes." Beverly tried the same action but gagged when Jack's cock was only half way into her mouth. "I'll have to get Jenn to give me lessons. She obviously does it far better than I do!

Shall I ask her if we can use you as a test dummy when she demonstrates her technique?"

Jack groaned and said, "You shouldn't talk like that!"

Beverly laughed, "Oh come on now! You're not going to pretend that she hasn't been giving you woodys for years? Well are you?"

Jack looked completely embarrassed as he admitted, "Well, maybe once or twice."

Beverly laughed again as she tongued his cock. "Tell me the truth, now. Are you aware of how many times Carrie set it up so you would accidentally walk in on a semi-dressed or completely undressed Jennifer?"

"She never!"

"Of course she did! Only six months ago Carrie told me about a time three years ago. She was cleaning her reef tank in the den, waiting for the sound of the shower in her room to stop. As soon as it did, she asked you to help her by getting a net from her closet, claiming she didn't want to drip on the carpet.

You walked into her room to find Jennifer fresh from the shower. You got completely embarrassed and ducked out of the room to come back here." Beverly tried to take the entire cock down her throat once again.

"Seriously, I've got to at least ask her, she makes it look so easy!

Anyway while Jenn was playing 'hide the sausage' with her lips, our daughter was sitting on Charlie's face letting his tongue minister to her lips!"

Jack's breathing had become intermittent and he was thrashing his head from side to side. "What happened next?"

Beverly climbed onto the bed and eased Jack's cock into her. As she started to pound away on him she said, "I have no idea. I shut the door at that point.

After all, I'm not a snoop!"

--- After they dropped the guys off at the Train station in Tarrytown, Carrie asked Jenn, "So what do you do now?"

She shrugged. "Well, Charlie's flying back to Birmingham so I guess I continue to visit with you guys until you get bored with me."

Carrie asked, "Well I've got a question. If you're visiting here is it your intention to remain celibate or do I set up dates for you?"

"No, I don't want you to set up any dates for me 'cause that'd feel like cheating but if Donnie were to call I'd probably say yes to him.

But what really blows my mind is the realization that if I got a call from a John I wouldn't hesitate going to his hotel room, collecting my money and fucking his brains out. Somehow that doesn't seem to register as cheating, just as work!" 

"That seems a little fucked up, Girl!"

"I know. I really enjoy the act of selling myself but I'm also sure that I'd quit in a heartbeat if Charlie asked me to."

Jenn sighed. "Sometimes I can't help but think I'm so messed up. I'd happily fuck a guy for money but I won't ever let Jimmy into my panties again because I felt disrespected last time. I positively glowed when Charlie referred to me as his girlfriend but if Donnie were to call to set up a fuck-date I'd be all over him so fast... and I consider him your property. Do you completely hate me?"

Carrie laughed as she sat in front of Jenn and took her hands. "Hate you? That's close to being impossible.

I discovered sex a long time ago and you've just found it. It's like you've had this hungry beast locked away in a hidden room all these years. Now you've let it out and you're feeding it and taking care of it just as you should be. The next thing you'll start doing, just as with any pet, is to learn to discipline it."

Carrie kissed her friend's forehead. "You started out willing to fuck anything with pants on and then Jimmy's dick got banned. Your sense of needing to discriminate will definitely grow." She giggled again. "Right now I'll bet that if he hit on you and you thought it'd be okay with Beverly you'd even fuck my Dad. It won't always be that way, trust me."




Jennifer Tests Her Wings Ch. 03



Carrie continued, "But I want to go out tonight and before he left Donnie asked if we could try it again without me getting shitfaced. If I could fix you up with a hot guy will you come with?"

"Not Jimmy?"

"Pshaw, the guy I've got in mind is way hotter than him and I know it for a fact that he'll make your pussy itch!"

Jenn said, "Okay I'm in, who's the guy?"

Carrie grinned, "Ray."

Jenn's pupils dilated to saucer size. "No fucking way!"

"Just after Donnie asked me out Ray asked if he could come along. I asked him why he didn't ask you himself."

"So what'd he say?"

"He said he never got the impression you'd be into him. Boys can be so incredibly stupid some times. You probably would have dropped for him at ten if he ever asked you."

"So what'd you tell him?"

Carrie started to head back toward her room. "The truth; that if he'd just blow in your ear you'd follow him anywhere."

--- The two of them had passed the last twenty minutes on the train in silence when Carrie reached over into Jenn's lap and took her left hand. Jenn didn't look up until Carrie said, "I know."

Jenn looked at her questioningly until Carrie repeated, "I know."

"Okay, what do you know?"

"I know and I also know you'll work it all out because you're such a take charge lady." Carrie raised Jenn's hand and kissed each finger as she continued, "You were stranded and homeless in the biggest city on the face of the earth and you not only worked it out but you sort of triumphed while doing it. You discovered sex, fucked a lot of people and wound up falling in love. You fucked a few more yet still considered yourself as being monogamous in your totally mental  sort of way. Now you've been hooked up with Ray and you're scared to death. You're scared because you feel like you're cheating on Charlie; you're scared because you went through puberty hoping Ray would strip your panties off and jump you on our front lawn and you think that when you fuck him you'll lose your independence and cede control of your pussy to him. Beverly told you about Ray's groupies and you desperately don't want to become one.

Oh Jenn... Ray's my brother and I love him but he's just as full of shit as any other guy, maybe even more so because of his semi-celebrity status. I love him and I love you but guess what? You're smarter and ten times more grown up than he is."

Jenn had tears in her eyes when she hugged her friend. "I'll still feel like I'm cheating on Charlie."

"So don't fuck my brother."

Jenn rolled her eyes, shoved her friend and said, "Get real, girl! I've wanted that cock in me for eight years."

The train pulled into the first stop in the Bronx and as the conductor passed through the car announcing "Riverdale, this stop is Riverdale." the two girls were laughing in each other's arms."

It was so weird! It was a first date with someone she'd known her entire life. She was paired up for the evening with the only boy she'd ever had sexual fantasies about long before she was quite sure what sex was. If it weren't for the fact that Connie was the fourth member of their quartet Jennifer would have been all over Don but if she'd done that she would have been guilty of not only poaching from her best friend but also it would have left a brother/sister pair which wouldn't work. At least Ray wasn't acting flamboyantly special tonight; in fact Jenn thought he was almost subdued. Don, on the other hand, was the gregarious leader of the table. The restaurant had been his choice. A narrow place serving Italian cuisine in the theater district it sported a bocce court toward the back about which an elderly group of paisanos argued after every roll.

Ray brought Jenn a fresh beer. "This feels very weird to me."

Jenn leaned on her elbow on the railing. "What does?"

"I made a mistake. When Don asked Carrie out I saw it as an opportunity to get close to you but I didn't think it through. I may love to party but it feels weird when one of the guys is trying to nail my sister..." He sighed. "I guess you're about as close to being family as anyone could get so I'll ask you. Aren't I supposed to feel protective about my little sister?"

Jennifer smiled and put her arm around his shoulders. "Okay so let me make sure I've got this all straight. You want to protect your sister from a guy you were fishing with that morning and seemed to me like he was a bud of yours. How'm I doing so far?"

Ray just nodded and Jennifer continued, "So you're going to protect your sister from someone she doesn't need protection from and even though you consider me part of your family you get Don to ask Carrie to invite me so you could... How did you phrase it? Oh yeah, so you could get close to me." Jenn closed the small gap and pressed her body up against his. "Tell me, does getting close to me involve exchanging any bodily fluids?"

Ray smiled and gave her a quick kiss. "Hopefully!"

"So it's a bad thing if a good guy wants to fuck your real sister but it's a good thing for you to fuck your almost sister?"

Ray laughed. "Yeah, that sounds about right."

"Interesting! You told Carrie you didn't think I'd be interested in you in the past but I guess something changed your mind?"

"Yeah, that's another weird thing. It was my mother's idea that I try to hook up with you."

Jenn shook her head. "That was probably her way of showing me alternatives to Charlie.

Ray Ray Ray, practically my whole life I've wanted you to pay attention to me. I can't ever remember a time when I wouldn't have done anything you wanted me to do and I mean anything. I used to use you as the standard by which other guys had to measure up to." She chuckled, "Maybe that's why I kept my cherry until this past weekend. This past weekend, Ray. 

So I've dispensed with that virginity nonsense and I've even got a boyfriend and you pick now to put the moves on me?

The worst part of this whole thing is that you'll probably get lucky because I've wanted you for so long but I'll be the one carrying the tons of guilt for cheating on Charlie!"

Ray brushed a few errant hairs out of Jennifer's face and kissed her forehead. "Look, I'm sorry but whatever happens between the two of us tonight I just don't want it to be anywhere near Don and my sister. They're at the table kissing and he's got his hand up her skirt and in her panties for Chrissake!"

Jenn clasped his hand and led Ray to the table where she said, "Look Ray and I are going to his place and I'd suggest you guys get a room before they throw you out for fucking on the bocce court."

Carrie's head shot up as she asked, "Ray, you're taking her to your place?" 

Jennifer could see an unasked question passing between brother and sister as Ray answered, "Not like that Car, we'll work something out."

As they were leaving the restaurant Jenn asked, "What was that all about?"

Ray shrugged. "It's got nothing to do with us but Carrie knows my apartment's got a bit of a reputation." Jenn waited so he continued, "Look, we're up to the big club, maybe back down, my parents have a home forty minutes from the Stadium, it would have been a waste to get my own place, so four of us split the cost of a really nice place on Central Park West.

What's got Carrie all upset are the apartment's longstanding rules. If you've got a steady girl you want to be with then you go with her to her place. If her place is unavailable take her to a hotel but any girl you bring to the apartment is meant for sharing. Over the years I can think of a lot of girls who've spent an evening walking naked from room to room as she was passed back and forth to whoever wanted to use her next. One pair of baseball groupie sisters from Dobbs Ferry didn't want to be separated from each other so we pulled out the convertible sofa and six guys kept both girls busy all night long." 

Jennifer said softly, "I see...

So Ray, which do you want? I don't have a place of my own to go to so do we head back to North Tarrytown and sneak into each other's rooms in your parent's house or did you plan on taking me to the apartment?"

Ray got indignant. "Wait one minute Jennifer, it was you who brought up going to the apartment."

Jenn maintained eye contact as she said, "That's true; I did. Only I didn't realize the implications of what I was saying. I had no clue about the secret special implications of your bringing a girl there. What was no secret was the fact that we've been staring at each other with bedroom eyes all night long. We both know it; Carrie certainly saw it, even Donnie was completely aware of it so you must have had some idea of where we were going afterward in your head."

Ray lowered his eyes breaking the steady eye contact they'd had. He shrugged. "I'm not sure. Maybe I was planning on taking you back to Don's place."

"But you killed that as a destination saying you couldn't bear to be anywhere your sister was getting laid. So I repeat, where did you want to take me?"

Ray still wouldn't look up. "I'm not sure."

"Ray look at me." He raised his eyes to hers. "Let me put it this way Ray, earlier I told you how I've wanted you my whole life. I also told you I couldn't remember a time when I wouldn't do anything you asked so I'll put it this way. Take me back to your parents, take me to a hotel or take me to the apartment; the choice is yours. This time I'll do whatever you ask." ---

The door swung open and as they entered they realized they had interrupted a card game at the dining room table. One of the five guys playing threw in his hand and went to a cooler they'd filled with ice and beers. "Hey Ray, this is a bit early for you isn't it?"

Ray answered, "Maybe a little but Jennifer and I wanted to get to know each other better so we came back." He led Jenn back to the end of the hall and into his bedroom. As soon as the door closed he took her in his arms and gave her the kiss she'd wanted her whole life. Their tongues danced as he gathered her dress in both hands and lifted it to her shoulders. They broke the kiss just long enough to pull the dress over her arms. As Jenn threw the garment aside Ray yanked her panties off. He pushed her down on the bed and buried his face between her thighs.

Ray was very skilled at what he was doing and Jennifer was building toward her second climax when she heard room door open. Ray kissed his way up from her pussy, across her belly, momentarily lingering on her nipples before lighting on her mouth. He lustily gazed into her eyes as his cock found entry to her core. His lips began kissing her left ear turning her head to the right and the waiting cock which slipped between her lips. He whispered into her ear, "Now's when the real fun starts slut."

Her own lust had been building but his words let the air out of her balloon. Her nerve synapses still carried their messages of pleasure from axon to neuron but by the time the data reached her brain they discovered the building was closed. She still knew how to make all the appropriate responses to the succession of cocks which entered her various holes but the glorious feeling she'd discovered a scant six days ago had been transformed into a physical exercise. She might just as well been at the gym.

Jennifer's mind wandered back to Ben and she couldn't suppress a quick smile between thrusts of someone's dick. Dear sweet Ben Roberts had been so nervous when he first propositioned her to be his whore for the evening. His fear of rejection had been so palpable that any fears for her own safety had been washed away as she considered his offer. When she informed him of her virginal status his lust didn't seem to be further whetted; in fact he seemed to be more protective of her feelings. When he pierced her hymen he gave her as much time as she needed for those same synapses to convince her brain that what she was feeling was oh so pleasurable. From beginning to end he'd made her introduction into the world of womanhood a very special experience she would treasure in her memories for the rest of her life.

Ben paid to fuck her so she was definitely his whore but he treated her like a princess. She felt she'd be lucky to get cab fare out of these guys at the end of the evening but they were treating her like the cheapest crack whore on the Avenue.

One of the men asked her if she was thirsty. Jennifer nodded yes and rather than getting her some water he began pouring the remains of his bottle of beer in the vague direction of her mouth. When the bottle was empty he pulled her on top of him and slipped his cock into her pussy as he shoved the neck of the bottle into her ass.

Molly Bloom's soliloquy notwithstanding, Joyce would have been proud of Jennifer's fifty minute stream of consciousness sentence as her mind catalogued her list of lovers and whatever factors had made each experience more or less memorable. She tried to be systematic but her mind kept dwelling on Ben and Charlie. She thought 'Ben was so nervous he almost couldn't bring himself to ask me and although he'd said he'd been with several hookers before (I wonder how many whores constitute several) he was always the gentleman even as his cock entered my ass for the first time as I wondered at his ability to still get hard after we'd fucked and while he was stroking my ass his lips were stroking my ear and cheek not even pausing when the phone was ringing with Charlie calling him to get the little whore's phone number (mine) so he could hire me to be his whore not suspecting that he'd wind up hiring me for four days even though he was even older than Ben and had a little issue that first night with a quick fuck before falling asleep but he came on strong and more than made up for it the next morning with the sweetest sex I'd ever had from anyone before and since even surpassing Ben who was my second oldest lover.

I wonder if I'm the only girl whose two best sexual experiences were with her two oldest lovers.'

As Jennifer was getting dressed one of the guys handed her two hundred dollar bills. He said "I know two hundred's way less than this evening's worth to a regular whore but think of it as a symbol. Believe me when I say that if you ever decide to turn pro you could make a fortune."

Jennifer didn't answer but put the bills in her purse as she headed for the door. Ray followed her to the elevator and down to the street. He apologized for the cash and what the guy had said about turning pro. Jenn smiled, "It's okay Ray. From his point of view I was just some little whore you'd picked up and besides, I can use the cash for cab fare."

She gave him a peck on his cheek and the cab pulled away. "Where to, Miss?"

"It's going to be the airport but I won't know which one until I go online and find out who flies to Birmingham."

"Alabama? That would be La Guardia."

Jennifer was about to text Carrie but she decided to wait until she was airborne. She looked at her watch when she saw the glow behind the Empire State Building signaling the impending dawn. She called Charlie.

"What's up sweetie? I was already up and you were my first thought of the day."

His comment turned on her tears. Between sobs she said, "I'm in a cab headed for La Guardia and I need a favor. I don't have a credit card and the way airlines stick it to you for last minute flights I'm afraid I don't have enough cash on me. Could you lend me the price of a ticket?"

"No problem, where do you want to fly to?"

It took her a few seconds to choke out the answer. "Birmingham if you'll have me or National Airport in D.C. if you can't."

"Give me your date of birth and your exact name as printed on your picture ID." She did so and he said he'd call right back.

Charlie took six minutes before calling. "There isn't a direct flight until 8:30 so tell your driver to drop you at the Stratos Terminal over at General Aviation. I've booked you a Citation and I'll meet you when it lands."

Now she was really sobbing and had trouble answering. She managed a truncated "Kay." before hanging up. 

After the jet took off she texted Carrie.

***wasn't hving much fun. Flyng to Charlie. Sorry abt skipping out on u but I'll call later

A response arrived surprisingly fast

***Birmingham?

***y

***u ok?

***wiser now

***give me 15 mins b back

Nine minutes later Jennifer got another text.

***USAir flight 3259 arrives BHM 7:51pm. your luggage will be on it.

***keep the green dress

***I alrdy did!

***luv you

***backatcha

***u w/Don?

***he's in me now

***AND UR TXTING?

***I got his permission

***k, tnx again

***we'll talk soon

Jennifer smiled as she drifted off to sleep. --- Their kiss lasted. When they finally stopped Charlie asked, "Luggage?"

"None with me but Carrie's shipping it to me on another flight. We can get it at eight this evening."

They were holding hands as they walked to Charlie's car. Jennifer spoke in barely above a whisper, "I love you Charlie."

"What?"

"I said I love you Charlie."

Still holding her hand he swung her around so she was facing him. "One more time."

"I said..." Jennifer raised herself on tiptoes and kissed each of his eyebrows, "that I'm in love with Charlie Taylor."

Charlie leaned in and kissed her lips. Her tongue was just about to emerge and enter his mouth when he pulled back to say, "I heard you the first time but I can't get used to how good it sounds."

Jennifer looked around and spotted another couple walking toward the terminal. She walked over to them and said "I spotted you two and thought that you needed to know that that man over there's name is Charlie and that I'm completely, gloriously and passionately in love with him."

The woman smiled and squeezed Jenn's hand. "Well, young lady I'm Eleanor and I'm happy for you. There's no better feeling is there?"

Jennifer's grin stretched from ear to ear as she answered, "Absolutely none, Eleanor!"

Eleanor's companion scanned Jennifer and said to Charlie, "You're a lucky man Charlie Taylor. By the way we're still on for golf on Friday?"

Charlie smiled. "I've already set up the tee times. Where are you guys off to?"

Eleanor said, "Our daughter Barbara is overdue with her first and her doctor said that if it didn't arrive by tomorrow he was inducing. I'm probably going to stay the week with her and her husband in New Orleans but Jack's coming back after the baby arrives."

Charlie smiled. "Well congratulations and a pleasant flight."

"Bye now and it was so nice meeting you...?"

"Jennifer; and it was nice meeting you both."

As they continued walking Jenn grasped Charlie's arm and laughed as she exclaimed, "Oh Charlie I'm so sorry but I never expected to randomly pick people who actually knew you!"

"No problem but when you think about it it wasn't such a random sample. Birmingham's a lot smaller than New York and when you reduce that by the number of people in a position to charter a jet..."

They walked a few more steps when Jennifer's grip tightened and she leaned in and kissed his neck. She didn't look at him but said, "That was the first time I've laughed in twelve hours and I love to laugh. Thanks for that."

When they got to Charlie's home he asked, "Hungry?"

"I couldn't eat a bite yet. I do have a request of my host, though."

"Anything."

"Could you take me to bed and hold me? Sex would be wonderful if you want but I really want to be naked and I really want to be held by you."

Charlie didn't speak but led her back to his bedroom overlooking the pool. He sat her at the foot of his bed and removed her heels. After pulling her back up he reached for the hem of her dress. She was wearing the same dress she'd worn to dinner without a bra and since Ray had destroyed her panties once Charlie removed her dress she was naked.




Jennifer Tests Her Wings Ch. 03



He pulled back the down comforter and sheet and deposited Jennifer in a cocoon of his creation while he undressed. Charlie pulled the covers back and began by kissing and sucking each of her toes before kissing the soles of her feet, then the tops, her ankles, calves, knees...

After a few minutes Jennifer had come to realize his intention was to kiss her everywhere. He's even pulled her ass cheeks apart and covered all of her there before sticking his fingers in her wet vagina long enough to lubricate his fingers and gently probe them into her asshole. Only when he'd finished with her hair and scalp did he crawl in beside her, resettle the comforter and take her in his arms. As he hugged her tightly he whispered in her ear, "There is no place on your body, inside and out, where any man's lingering touch has not been replaced by mine. No one's flesh has caused you an indignity which hasn't been replaced by my loving touch and Jennifer Reynolds... I do love you too."

Jennifer only sobbed four times. Only four sobs but she could feel how awash their faces were with her tears. She wanted to thank Charlie for making her cocoon but thought herself incapable of speech so she crawled down and took his cock into her mouth. Charlie threw the covers aside and pulled Jennifer's body on top of him as his tongue began paying homage to her glorious pussy. This new position suited Jennifer quite nicely since it made it simple for her to demonstrate her deep throating talents. She virtually inhaled his dick and buried her nose in his pubic nest while his fingers kneaded her butt cheeks as his tongue painted its way up and down her labia without touching her clit or its hood.

When he heard her first tiny moan of the session Charlie allowed his tongue access to a simple pass over her clit to which Jenn responded with a violent thrust into his mouth. She quickly spun around and sat atop his groin as she began to dry hump him. Only when her own wetness had thoroughly drenched Charlie's cock did she raise herself and insert just the head into her. Her tiny slow gyrations gradually absorbed more and ever more of him until she was fully impaled on his spear.

This was the first time she'd made love to anyone since the last time she was with Charlie in the house under construction.

Carrie had called the airline, packed all Jennifer's things and one small bag for herself when she heard Beverly come in the front door. As Carrie took the last of the bags down the stairs Beverly asked, "What's wrong? I could hear it in your voice that something's wrong."

Carrie told the truth, "I honestly don't know, Mom. Something frightened her or hurt her and she ran to the safest place she could think of."

"Alabama and Charlie."

"Give that lady a cookie." She tossed her mother her phone. "The text traffic between her and me is in there. See what you make of it."

Beverly read the texts stored in her phone. She was gritting her teeth when she muttered "That God Damned self centered bastard!"

"Hey! That's my brother you're insulting and we don't know what happened so chill out."

"Of course you're going with the luggage?"

"Of course I am and we'd better get moving if you're driving me to the airport."

"Let me pee first and we're out of here."

As they headed down the Deegan Beverly looked at the pile of luggage in her rear view mirror. "They're going to kill you with extra luggage charges. I'm reimbursing you for your flight.

I should send the bill to Ray!"

"I don't want to leave my cocoon and I definitely don't want to wear that dress again so could you get my bags at the airport?"

Charlie was rubbing his wet hair having just showered. "Sure but you'd better stay near the phone in case they need to talk to you to give me permission."

He got to the airport at 8:25 and headed straight for the baggage area assuming they wouldn't put shipped bags on the carousel. But no one from US Air knew about any shipped bags or any bills of lading under the name of 'Reynolds'. He reached for his phone to call Jennifer for Carrie's number when he felt an arm on his shoulder. Before he could fully turn Carrie asked "Is she alright?"

Charlie smiled, "Carrie I'm so pleased you came! Yes, she'll be fine. She's sporting a few psychological bruises but she'll be great in a couple of more days."

"What happened?"

Charlie met her eyes as he shrugged, "I have no idea for sure and I haven't asked. She'll tell me when she's ready."

Carrie kissed and hugged him with all her might. "You know what? Jenn's Dad has always been right about her. She's a very smart and resourceful lady. Even when she's running on instinct she makes the right decisions. My feelings were a little hurt when she didn't come to me for help but you're the perfect person she needs now.

Have you guys eaten?"

"I had an early breakfast but Jennifer hasn't eaten all day."

"Call her and tell her you can't go an entire day without eating and since you're bringing her clothes you're going out to eat.

I'm hungry and I want to buy you guys dinner and I'm not paying to feed a nasty cum stained girlfriend of yours so tell her to clean up."

"Yes Ma'am."

Jennifer broke down crying again when she saw her friend. She ran still naked from the house not even thinking about neighbors and hugged her in the driveway. Charlie left them to each other as he carried her bags to his room. When he was finished he went behind his bar to pour himself a drink when the girls came in. "I just poured myself a drink. Anyone else want one?"

The girls both settled on a Cabernet. Jennifer took her drink and asked where her bags were.

"In our room."

She grabbed Carrie's hand and giggled, "Hear that wench? I'm part of an 'our'. Isn't Charlie beautiful?"

"Jenn! You never say things like that to men; you'll give them swelled heads. Besides, I already told him that earlier."

The after dinner coffee was being brought when Charlie excused himself to the men's room. As he returned he saw both girls looking at him and whispering in hushed tones.

As he resumed his seat he asked, "All right, what are you two plotting?"

Carrie feigned indignation. "We weren't plotting anything!"

Jennifer added, "That's right, we were just wondering how much you're going to enjoy being the meat in the middle of the sandwich we're going to create since I invited my best girlfriend to join us for the night in 'our' bed."

Charlie didn't respond but his mind was already feeling smug. He thought 'Let's see, how much would any man my age enjoy lying in bed sandwiched between two nude beautiful sexy teenage girls?'

He smiled as he signaled for the check. 



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 it that 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 her date 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. A really 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 out except 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 with difficult 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. She really 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 feel so 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 her off 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 like Pretty 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.




Jennifer Tests Her Wings



"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 you might 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 in very close to him. "Look, I promised Mr. Taylor that everyone would be there." She rubbed the lapels of his jacket. "Isn't there anything I can do to convince you to make this one 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 her seventh 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 really special 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."

"I knew 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 local Teens '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. "I still 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 absolutely knew that she was now making love for the first time. She wasn't quite sure what set it apart, but she liked it, she really 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.