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 Antalya Escort 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 Antalya Escort Bayan 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! 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 Escort Antalya 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.”

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