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.