tagFirst TimeJennifer Tests Her Wings

Jennifer Tests Her Wings

byReefkeeper©

"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!

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