Trip to Chicago Ch. 02: Jackie

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tagIncest/TabooTrip to Chicago Ch. 02: Jackie

(Reading the first chapter of "Trip to Chicago" is strongly suggested. It introduces all of the characters and sets the stage for the beginning of this story.)
David woke up and looked at the beautiful woman who was still sleeping next to him. Last night was the second night Dana came back to his hotel room, but since today was Saturday and she didn't need to go into the office, she stayed the night. David smiled thinking about last night; the sex was fantastic. But he really liked, Dana, too.
He crawled out of bed without waking her up and hopped in the shower. When he came out of the bathroom with a towel wrapped around him, Dana opened her eyes.
"Good morning," she said, ending with a smile.
"Good morning to you!", David replied. "Sleep okay?"
"Mmmmm, yes, I sure did. I had this fantastic dream where I had great sex with a nice guy."
"Really? That's so funny. I had a dream where I had great sex with an absolute angel. And, damn, she looked just like you!"
As Dana got out of bed, David admired her perfect, naked body.
"I gotta pee," she said, as she disappeared into the bathroom. After she peed and washed her hands, she used David's toothpaste and her finger to brush her teeth as best she could. She really just wanted to freshen her breath. When she walked out of the bathroom, she walked up to David, who was still just wearing the towel around his waist, wrapped her arms around him, and asked, "what time do you have to be at your brother's?"
"No special time. Early afternoon."
"So, do you have time to make good on your promise?"
David looked confused. "Promise?"
"Thursday night you asked me if I wanted to be on top. I said next time. But last night we never got around to that. Do you have time now?" she said with a smirk.
"Well, gee, I've got the time… but let me think about this. Do I want to have more sex with the most beautiful woman I've ever met and let her ride me? Do you have to know right away, or can I get back to you?"
"Okay, if you're not sure, never mind." Dana let go of him and turned around. David grabbed her, spun her around, put his mouth on hers and his hand on her breast. Dana giggled until David thrust his tongue in her mouth. They kissed as Dana pulled the towel off David and placed her hand on his hard dick.
"Well, this guy seems ready."
"You have that effect on me," David replied, as he lowered his mouth to Dana's breast and licked her nipple, making her moan.
"Mmmmm, yes," she said, her breathing already increasing.
David slipped his right hand down to her pussy, sliding his middle finger between her lips. This brough a louder moan from Dana. David slipped his finger into her, and she groaned. She was already very wet.
"Get on the bed!" she demanded, sounding desperate. David followed her instructions, lying down on his back with his dick pointing up toward his face. Dana climbed on top of him, with her knees straddling him. She grabbed his dick, lifted it until it was just beneath her pussy, and slowly lowered herself onto him. They both moaned at the same time. Dana put her hands on David's stomach for balance and lifted herself up. Then she came back down, again causing both of them to moan again.
Dana continued bouncing up and down, and they both were enjoying the incredible feeling. Dana squeezed her muscles around David's dick, causing him to moan louder than before. David reached up and used both hands to pinch both of Dana's nipples, and she let out a loud moan herself.
David was trying hard not to come too quickly. It felt so incredible to be inside Dana, and when she started squeezing her muscles, it felt even better. David pulled himself up and stuck his mouth on one of Dana's breasts, sucking her nipple and flicking his tongue over it. He put his hands around Dana's waist, pulling her body toward him each time she came down on him. This caused her clit to rub against him and made her gasp. Both of them were breathing very hard and grunting with each stroke.
Finally the pleasure took over her body as her orgasm hit her. She stopped moving up and down and instead just kept jerking her body forward over and over while impaled on David's dick. This motion, along with her contractions squeezing David, caused David to suddenly spurt stream after stream of cum. He grunted with each spurt as he wrapped his arms around Dana and squeezed her with each spurt. When they both finished, he fell backwards, pulling Dana with him. They lay there quietly except for the gasping for air.
Finally, their breathing returned to normal, and they both remained silent. David still had his arms wrapped around her, never wanting to let her go. She eventually lifted her head, smiled at him, and gave him a soft, loving kiss on the lips. No tongue, just lips, but it sent a shock through David.
"I'm really going to miss you," she said.
"Mmm. Me, too. But I'll make sure I come to Chicago more often."
"I'd like that. A lot!"
Dana laid her head back down on David's shoulder and thought about the last three days. After a long drought, she had incredible sex three days in a row with a really nice guy. She recognized that David was a lot older than she was, and she wasn't exactly reserving a date to marry him, but she really liked him. She realized the desire for sex could be clouding her thinking, but even if they were only fuck-buddies, what was wrong with that?
She lifted her body up. "I gotta' take a shower." She climbed off of him and went into the bathroom.
While she was washing her hair, she heard the shower door open. She turned to David and said, "I thought you already took a shower."
"Yeah, I did. But the shower looks a lot better with you in it. And I thought you'd like someone to wash your back." He turned Dana around so her back was to him. He took over for Dana's hands and continued rubbing the shampoo into her hair. He slowly massaged her head from the back up to the top. He pressed his palms into her temples and applied just the right amount of pressure. Then he returned to using his fingers to rub her scalp.
"Mmmm, that feels nice!" Dana had her eyes closed and was leaning back into David. Even when he rubbed her head, she got excited. He turned her back around, pushed her forehead back, and had her take one step back so her hair was under the shower head. He reached around her to rinse her hair under the water. When the shampoo was all gone, he wrapped his arms around her and pulled her tight against him.
"I had to feel your naked body against me one more time. You feel so good."
Dana smiled. "You feel pretty good yourself."
David grabbed the body wash, put some in both hands, reached around Dana, and rubbed it on her back. He pulled her against him while he washed her back, smashing her tits against him. After he rinsed her back, he put more body wash on both hands and starting washing her breasts. He very gently slid his hands all over them, taking a little extra time on her nipples. As Dana closed her eyes and her nipples started getting hard, David pinched them very gently. He grabbed the hand-held shower nozzle and rinsed off her breasts.
After he replaced the nozzle, he put his mouth on her nipple and flicked his tongue over it a few times. Then he kissed her between her breasts. Then a little lower. Then lower. He kept going down until he kissed her mound.
"Hold onto the grab bar for support," he told her. Then he lifted her right leg and put it over his shoulder, giving him full access to lick her pussy. He slipped his tongue between her lips and licked over and over. Dana moaned with each lick. Her clit was begging to be licked, and David did not deny its need. He quickly flicked her clit over and over and over. Dana shrieked with each lick and thrust her body. She was tightly holding the grab bar so she wouldn't slip.
Seeing how she reacted to each lick, he decided to not change a thing. He simply continued the exact same licking at the exact same pace. He continued this for a few minutes, loving every minute of it. Dana's sounds got louder and faster until she finally hit her limit
"Oh, GOD!" she mumbled, with the "God" stretched out for 5 seconds. Her body started jerking every two seconds.
David continued licking, but he made sure to hold her body tight so she wouldn't slip, knowing she'd probably loosen her grip on the grab bar. After a minute he removed her leg from his shoulder, stood up, and hugged her tightly. She laid her head on his shoulder, hugging him back.
After a minute, she pulled her head away, looked up, and smiled. "I'm thinking my shower tomorrow morning isn't going to be NEARLY as much fun!"
"HA! I hope not! I'll be jealous if it is!"
David finally turned off the water, grabbed two towels, and handed one to Dana. She slowly dried herself off, still moving slowly as she was still enjoying the after-effects of her orgasm.
They both got dressed, and David finished packing. "You ready? I'll get us an Uber," he said.
"Umm, yeah. Remember… if nothing else, I'm a gentleman. I think I can take you home."
Dana laughed. "Oh, yeah, I almost forgot. You ARE a gentleman."
When the Uber pulled up to Dana's apartment, they both got out.
David hugged Dana, and he spoke first.
"Thanks for making my trip to Chicago something I won't forget. I just might have to come back this way."
"MMMM. I'd certainly like that. Thank you for everything. You're a nice guy, David Martin! I hope to see you soon."
They gave each other a warm, but not too-crazy, kiss — they were standing out in public. David stood and watched as Dana walked up to the door and disappeared inside.
He got back in the Uber and left the city on his way to his brother's house in the northern suburbs of Chicago. He had a big smile on his face.
As the Uber driver backed out of his brother's driveway, David looked around at all the large houses with three-car garages. He pulled up the handle of his suitcase and walked up to the front door. He rang the doorbell and waited.
After less than 15 seconds, the door whipped open and Jackie screamed, "DAVID!" She stepped out onto the front step in her bikini and bare feet and threw her arms around him. "I am SO glad to see you!"
David gave her a firm hug back, pulling her tight against his body. Then he let go, took a dramatic step backwards, and looked up and down Jackie's body. "Holy fuck, Jackie. You look fantastic!"
Jackie gave a broad smile back. "Oh, you noticed? I wasn't sure you would. I only dropped 65 pounds."
David laughed. "Jesus Christ. I can't stop looking at you. Sorry."
Jackie stuck out her arms and did a twirl. "Look away!" Then she grabbed his hand. "C'mon in. Nick should be back from golf within an hour."
They walked into a large foyer.
"Wow, your house looks beautiful. A little bigger than your first apartment, huh?"
"Yeah, well, we like it. I'll give you the 25-cent tour on the way to your bedroom."
When they reached the guest room, Jackie said, "Are you okay? Do you need to rest?"
"Nope, I'm fine."
"Okay, put on a bathing suit and meet me by the pool. It's a little too early to start drinking, so you'll have to settle for iced tea. I'll make some sandwiches."
She walked out and closed the door. David couldn't believe how different — and how incredible — she looked. Jackie always had a pretty face but, but was always a little overweight. Of course, it never mattered to him — he always thought she was fantastic and was a little jealous when his brother married her. But now she had an incredible body, too. Nick was definitely a lucky man.
When he got downstairs, Jackie was sitting out on the patio with sandwiches and iced tea set out on the table. As they ate lunch, they caught up on things.
"So, how'd you get that hot body?" David asked with a smile.
"You won't believe this," Jackie replied, "but eating healthier and exercising actually make a difference. Who knew?" They both laughed a little.
"What was the motivation to suddenly do this?"
"Eh, lots of things. Ask me later."
David wondered why she answered like that, but dropped it. They continued talking about wok, family, living in Chicago, her job as an economist at the Federal Reserve Bank, his work, and everything else under the sun.
After about an hour, the screen door flew open and Nick yelled "DAVID!"
David stood up and gave Nick a giant bear hug. After they broke the hug, Nick said, "Man, it's been too long!", and he grabbed David again for a second hug. He finally broke it and they both sat down. Jackie got up, walked into the kitchen for a minute, and came back out with three bottles of beer.
"Wow," Nick said. "This brings back memories. How often was it the three of us at school drinking beer half the night?"
"A lot!" David said. "But back then we could only afford cheap beer."
The three of them told stories, reminisced about the old days, and sometimes laughed their asses off. At one point David mentioned how hot it was.
"Umm, did you notice there's a pool about 15 feet from you?" Nick asked.
"Oh, are we allowed to swim in it? I thought it was just for decoration. Let me check it out." He stood up, walked to the edge, and did a perfect swimmer's dive into the pool. As he came to the surface, he immediately started swimming, fairly quickly, to the other end. He did a flip turn and came flying back the other way. He repeated two more lengths, then pulled himself out of the water. He grabbed a towel, dried his body, and walked back to the table.
"Jeez, you've still got the form!" Jackie said.
"Eh, I thought the flip turn was a little sloppy," Nick chimed in. "Coach Roth would make you do another ten of them." This brought a laugh from all of them.
"Remember when you told me you were putting in a pool, and I said it was a stupid thing to do in Chicago, where you can only use it for five, MAYBE six months?"
"Well, I STILL think it's a stupid thing to do in Chicago." He paused for 5 seconds. "But I'm REALLY glad you've got it today!"
Nick slapped him on the shoulder. They continued talking outside and continued drinking beer.
After a while, David caught himself staring at Jackie. He couldn't get over how incredible she looked. Her breasts, which never really stood out when she was heavy, were perfect. Not too big, not too small. Just perfect. Her stomach was perfectly flat, and her legs and arms were well-toned. When he realized he was giving her body the once-over, he suddenly got angry with himself. 'This is Jackie, you asshole. She's your sister-in-law. STOP IT!' he thought to himself.
That night, they went out to dinner at one of Jackie and Nick's favorite local restaurants, and the conversation never stopped. There was lots of good food, lots of wine, and lots of laughing. Lots of really loud laughing! It was always the same whenever the three of them got together; they all loved each other and really enjoyed spending time with each other. Jackie hadn't been this happy in a long time.
Fortunately, they had walked to the restaurant; no one was in shape to drive. As they walked home on the hot, humid night, David asked what the plans were for the Cubs game the next day.
"I bought some great tickets from a friend who has a share of season tickets. He told me where I could park behind someone's house — just tell them I'm using Larry's tickets," explained Nick.
"Drive? DRIVE? Aren't we taking the L?" David asked.
"No, we're not taking the L. I haven't taken the L in 20 years."
"Oh, c'mon, Nick. I want to relive our childhood. We never DROVE to Wrigley. We took the bus or someone's mom drove us to the Howard Street station, and we took the L. I want to relive that."
"Jesus, David, how old are you? We didn't drive when we were kids because: A — we were too young to drive, B — there was NO parking, not that there's THAT much now around Wrigley, but a little more, and C — we wouldn't have been able to afford to park behind's someone house. Now we can."
"C'mon… let's relive our childhood. Please. PRETTY please?"
Jackie was laughing the whole time as her two favorite guys were still arguing like brothers always do.
Finally, Nick let out a deep exhale. "FINE! We'll take the fucking L. But I'm driving to the Swift, not to Howard Street," he said, referencing an extension of the L.
"Thank you, big brother. You always take care of me," David said as sarcastically as possible.
"I suppose you'll want to borrow a Cubs T-shirt for the game tomorrow, huh?" Nick asked.
"Nope. I bought a Baez shirt on-line. I'm ready to go." Nick smiled at his brother's advance planning.
"Okay, boys, if you're all done fighting, I'm going to sleep. All the food and wine are causing me to close my eyes right now. Goodnight, David." She threw her arms around David and gave him a sweet kiss on the lips. "I'm glad you're here."
David pulled her tight and enjoyed feeling her body against his. Then he suddenly realized he might be enjoying it a little too much, and released her.
"I'm glad I'm here, too. See you guys in the morning."
"You have everything you need?" Nick asked.
"Yep. Jackie got me set up earlier. Thanks."
As Nick and Jackie walked up the stairs in front of him, David couldn't help but admire Jackie's ass. He still couldn't believe how much weight she lost and how fantastic she looked.
The next morning was a scorcher. David and Nick were wearing shorts and Cubs T-shirts. Jackie had on very short shorts and a Cubs tank top. David thought she looked fantastic. As they piled in into the car, Nick made one more appeal to David.
"You sure you don't want to just drive to Wrigley? I've got a great parking spot to use that's only one block from park."
"No way. We're takin' the L, baby!"
Nick sighed and put the car in reverse to back out of the driveway. When they got to the Swift, the parking lot was about half full. Since it was a Saturday, odds were that 95% of the cars were from people going to the game. And standing on the platform waiting for the train, 95% of the people were wearing Cubs T-shirts. Lots of the women were wearing tank tops and halters. David seemed fascinated by one young woman whose halter exposed some side boob. Jackie stood on her tip toes to whisper in David's ear.
"You want me to ask her if you can have a lick? Or maybe just cop a quick feel?" Jackie said through her laughing.
David turned a little red. "Was I that obvious?" Jackie kept laughing as she just nodded her head.
Finally, the train came, and they hopped on for the short ride to the main Howard Street station. They transferred trains and were on their way. As the train started pulling into Addison Street, David saw the back of the center field scoreboard — exactly like when he'd arrive at the park as a kid.
The ballpark had added new restaurants and changed the profile in some ways, but it was still Wrigley. And one thing never changed for David. When he walked up the steps from the lower-level concession stands to get the first view of the field for the day, he had a huge smile on his face.
He was 12 years old again. The first view of all that grass, with the perfectly shaped base paths and the ivy on the wall, ALWAYS made him smile. Even as an adult, it had the same effect. The only difference now was that they were able to afford much better seats, so they were much closer to that beautiful field. But the smile was the same.
They found their seats, and Jackie sat between the boys. To David's left was another young woman wearing a low-cut t-shirt that displayed a lot of cleavage. Jackie again laughed at David's fascination with her chest and elbowed him in the ribs. They both laughed.
After a couple of beers, David and Jackie switched to water. It was hot, and if they relied on the beer to keep them hydrated, they were going to be smashed by the end of the game. Nick drank a few more by himself, but he, too, switched to water. The beer vendors were going to have a very good day today.

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