Trip to Chicago

Thanks to all the international travel he did for business, David had the highest frequent flyer status. That meant he always boarded in the first group, never had to worry about overhead space, and usually got upgraded to first class. He was surprised he wasn't upgraded today, but it must have meant a whole lot of people actually paid the first-class ticket price. So, he was sitting in the extra-leg-room section of coach as he played his usual game of examining people as they got on and deciding whom he did -- and did not -- want to be seated next to him.

There were three categories of people: fuck yes!, fuck no!, and ok.

Of course, the people in the Fuck Yes category were hot looking, young women. This was a rare time when David allowed himself to be shallow and somewhat of a pig, judging women based on their looks. He didn't do that in "real life" instead always judging women more by their brains and their values than their looks. But during the airplane seating game, looks it was.

The Fuck No category was pretty much based on one thing: size. He had been on way too many flights where he and the larger person next to him shared his seat. Again, he had nothing against large people -- except when they sat next to him on an airplane.

And the OK category comprised 90% of the people on the plane -- anyone who didn't fall into the other two categories.

So as he watched people enter the plane and walk down the aisle toward him, he quickly put each of them into a category: ok, ok, YES, ok, ok, NO, ... And so it went.

A larger person started slowing down as he approached his row. His size was somewhere between ok and fuck no, but he was wearing a sleeveless shirt with a dropped armhole, with body hair coming out everywhere. This definitely threw him into the no category. When he looked at the seat next to David's aisle seat and nodded, David sighed. He got up to let the guy in. Much to his pleasant surprise, he moved into the window seat, not the middle seat next to David.

As fewer and fewer people were walking onto the plane, David thought maybe he really lucked out and the middle seat between him and Mr. Hairy would remain empty. He closed his eyes for a minute thinking about his trip, and he heard a sweet voice say, "Excuse me." When David opened his eyes, he was staring at an angel. A tall, well-toned, blond, young woman -- maybe 26 or 27 -- with beautiful, small breasts hidden behind a tight stretchy top was pointing to the seat next to him. "That's mine."

David flashed the biggest smile possible as he jumped up and stepped out of the way. After she climbed in and sat down, David returned to his seat.

The woman fit in the seat easily, but she pushed herself completely toward the armrest between her and David. Apparently, she wasn't keen on the idea her body touching Mr. Hairy's. David smiled to himself, thankful both that she was between him and the other guy, and that she was leaning toward him. In his mind, he figured that she would lean further into him, when their bodies touched she would get incredibly turned on, and she'd invite him to join the mile-high club. David actually chuckled out loud at his over-active imagination, but, he figured, he could dream.

As the woman put her computer bag under the seat in front of her, David noticed her business card.

"Do you work with Randy?" he asked her. She had a confused look on her face.

"I saw your business card on your bag," he said. "Randy Simons and I were friends in college. Perhaps you've heard of him?"

The woman laughed. Randy was the head of the litigation department at the law firm and brought in more business to the firm than anyone else. EVERYONE knew Randy.

"Let me think," she said sarcastically. "I THINK I might have heard of him," she said with a beautiful smile. "Hi, I'm Dana."

"Hi, I'm David. Nice to meet you, Dana. So, are you the Managing Partner of the firm?"

Dana let out a loud laugh. "Almost. I've been there just over a year. I like to think of myself as the Managing Second Year Associate. But I don't tell anyone."

David explained that he hadn't seen Randy in a couple of years, but they'd trade emails every six months or so just to say hi.

"Were you friends with him in law school?" she asked.

"No, I'm in private banking," he said. "But if I DID go to law school, they sure as hell weren't going to let me into Yale, like Mr. Smartypants."

Dana laughed. "Oh, I see. You were the dumb friend who only got to know him at Harvard. Amazing to think you could even find a job after only graduating from there," she said with a smile.

It was obvious to David that Dana was smart -- if for no other reason than she was working at a top law firm -- and funny. And she just happened to be quite beautiful. The trifecta.

She asked about his trip to Chicago, and he explained he was combining business with pleasure.

"I've got three days of meetings, including one at your firm. You guys represent one of the other parties in a deal I'm working on. Then I'm taking a week off to visit my brother in the northern suburbs. We grew up here, and he moved back almost a year ago. I haven't seen him since he moved back, and I'm really looking forward to it."

"Are you staying at his house?"

"Next week I am. The first few days I'm staying downtown. At the Peninsula."

"Oh!" she said. "That's supposed to be a great hotel. I've always wanted to see those rooms."

David smiled. "Are you asking me to invite you to my hotel room?"

Dana turned bright red. "Oh my God. No. I didn't mean that! I'm sorry... I just meant...."

David interrupted her, laughing. "It's okay. I'm just giving you a hard time."

Dana gave him a gentle whack on the shoulder just as the safety announcement started.

When the safety announcement was over, David and Dana continued talking. He asked her about her ridiculous hours, and she said she knew what she was getting into. But she liked the work, and MOST of the partners weren't assholes. She told him at her last trial, the partner in charge totally excoriated two attorneys and three paralegals -- and that was before the actual trial even started. Except for that guy, though, she said most people were pretty decent.

David asked Dana if work left her any time to date, and she laughed. "I haven't been on a real date since I graduated law school. Between studying for the bar and immediately being expected to bill lots of hours, there's no real time."

Dana asked David what he was going to do while he was back in Chicago.

"The only plans I know about for sure are that we're going to a Cubs game Sunday. My brother and I used to go games all the time, but we haven't gone together since high school. It should be fun." He explained he was looking forward to hanging out with his brother and his wife.

"Do you get along with your sister-in-law?" Dana asked.

"Oh my god, yes. I absolutely love Jackie. My brother was at Harvard, too, two years ahead of me. He started dating Jackie shortly after I started my freshman year, so I've known her a long time. She's fantastic. Smart. Funny. Just a great person. We got along right from the get-go."

David started thinking about Jackie and just how happy he was that she and Nick got married. He would do anything for either of them. In fact, he once got into a fight for Jackie.

Jackie was always a little overweight. She had a beautiful face and beautiful blue eyes, but it wasn't her beautiful face that made Nick (and David) fall in love with her. She was just a wonderful person. She always helped people, she volunteered tutoring underprivileged kids, and would do anything for anybody.

One day some asshole said to David, "Why's your brother date that fat pig? She must really give good head."

Before the guy pronounced the "d" in the last word, David punched him in the face and broke his nose. The guy took a couple of swings, but a few other guys held him back, knowing David would beat the crap out of him. He never told Nick or Jackie what happened.

David and Dana continued talking during the entire flight. When the pilot made the "prepare for landing" announcement, Dana looked stunned. "Oh my god, I can't believe we're already here. I talked the entire flight. I hope you weren't planning on getting any work done on the flight. I'm sorry."

David smiled. "Don't be silly. I loved talking to you. It really was my pleasure."

When they got off the plane, they exchanged the usual "nice talking to you" pleasantries, and they each went their own way.

After he got his luggage, David got an Uber and headed to one of his clients. It was a hot, humid, sunny Chicago day, and he was sweating while just waiting for the car. By the time he got to his client's office, he was ready for a shower. Fortunately, he knew this client well, so he didn't feel too bad looking a little disheveled. But his client couldn't pass up the opportunity to ask him, "How much do I pay in fees to have some hot, sweaty guy show up to help me invest my money?" They both laughed as they got down to work.

He was happy when the day was over and he finally got to check in at the hotel. The rooms were top notch, and the bathroom looked more like a spa. David stripped off his clothes, took a shower, and put on some lightweight clothes before heading out to dinner.

The next day he had a couple of calls and meetings with clients and some potential clients. As soon as he got to his afternoon meeting, his potential client apologized but said he'd be unable to make dinner. David had been trying to woo this client for months, and he had made reservations at a very hot, very expensive restaurant. He was disappointed, but then he smiled to himself as he thought about Plan B.

At one of their breaks, he went on line to look up a number and placed a call.

"Dana Anderson. How may I help you?"

"Hi, Dana Anderson, this is David. From the airplane. Hope you remember me."

Dana smiled. She certainly remembered him. In fact, she thought about him a couple of times since the flight. "Hi, David. To what do I owe this pleasant surprise?"

"I enjoyed talking to you on the flight. And it turns out my dinner plans just got cancelled. I was wondering if you'd be willing to meet me for dinner."

"Hmmmm," she said, rather sarcastically. "So, I wasn't your first choice for tonight?"

"Trust me," he said, "If I had met you before I met my potential client, I would have planned dinner with you instead and thrown away the millions -- no, make it the BILLIONS of dollars I would have made from this guy."

Dana laughed. "Actually, I'd love to have dinner with you. Thank you. Where and when should I meet you?"

David told her the restaurant and said reservations were at 7:00. Dana got very excited.

"Oh my god! I've been dying to go to that place, but it's really hard to get into. Oh yeah, and I can't afford it."

David laughed. "Well then this works out for both of us. See you at 7:00?"

"Absolutely! Thanks, David. I'm looking forward to seeing you."

After his meeting ended, David headed back to the hotel. He made some calls, ran through his email, grabbed a quick shower before heading to the restaurant. He got there about 10 minutes early and checked in. His table was ready, but he told the hostess he'd wait at the bar for the other person. He grabbed a spot at the bar where he could see the front door.

When Dana walked in, David walked over to greet her. She looked stunning in her very-professional-looking navy business suit with a powder blue satin blouse. When she saw him walk over, she broke into a beautiful smile. She said hi and gave him a warm hug.

"Sorry about the billions of dollars you might lose, but I'm glad your client backed out of dinner. Thanks for thinking of me."

David chuckled. "Fuck it -- it's only money," he said. "Our table's ready. C'mon."

He put his hand on her lower back and gently nudged her toward the hostess' desk. Dana closed her eyes for just a second when he touched her. When they were seated, Dana looked around.

"This place is beautiful. Have you been here before?" she asked.

"No, but everyone said it's the place to go to."

The waiter came over, and they ordered drinks. Dana asked how his meetings went, and David told her things were going well. He didn't mention that dinner with her made the whole day even better.

David asked her a lot about her work. He had learned she had an engineering undergraduate degree and practiced Patent Law. He knew the big law firms worked associates incredibly hard and that trials were especially brutal.

"The other day you mentioned you'd been to a trial. Only one so far?"

"Yes, but it was punishing. I'm learning some lawyers aren't exactly the best planners. We had eight months to prepare for this trial, we headed out of town a week before the trial starts, and we were literally working 20-hour days that week before the trial. Talk about waiting until the last minute!"

David laughed. "But the partners were smiling, thinking about all those hours they were going to be billing the client!"

Dana laughed, too. "Yeah. Billed hours. Billed hours. That's all you hear about. I think that should be the name of the firm."

After a half hour, David signaled to the waiter, and he brought over menus. He told them about the specials, described a few of his recommendations, and left to let them decide. After a few minutes, he came back and took their order. David asked Dana if she'd like some wine, and she said she would. He ordered a bottle, and they continued talking.

During dinner they talked about growing up, family, even the dangerous topic of politics, as they were each pretty sure they bent in a similar direction.

After a wonderful meal, David forced Dana to order some dessert. When they finally finished the obscenely decadent and expensive dessert, David asked for the check.

Dana couldn't believe this guy. He was smart, funny, kind, interesting, and good looking. He obviously was successful. He's the kind of guy you want to ask, "why aren't you married?"

When the bill came, David did a quick perusal and then made a face. "This is not right." He caught the waiter's eye and signaled for him to come over. For the first time, Dana's image of David was a little shattered. Is he going to complain about the prices? Did he not realized he ordered very expensive wine? All she could think was "Please don't make a scene in this fancy restaurant."

When the waiter came over, David said, "I think you made a mistake here."

"I'm sorry, sir, what's wrong?"

"You forgot to charge us for the two desserts."

Inside, Dana let out a sigh of relief. He wasn't making a scene -- he was correcting a mistake where he was UNDER charged. SHE always did things like that, but most of her friends thought she was stupid for doing so.

"No, sir, my manager told me not to charge you for dessert."

"Really?" David asked. "Who is your manager?"

"Jerry Morrison."

David smiled. "Is Mr. Morrison available?"

"I'm happy to check, sir."

Five minutes later, a guy in a tux was walking to the table with a smile on his face. David stood up.

"Jerry! I didn't know you were back in Chicago!" They gave each other a hug. He turned to Dana.

"This is my friend, Dana Anderson. Dana, this is an old friend of my brother and mine, Jerry Morrison."

"How do you do, Ms. Anderson," Jerry said, as he extended his hand to Dana. She gave him a firm handshake and said, "Nice to meet you."

Jerry and David spoke for a few minutes. David thanked him for the desserts, sat back down, and took out his credit card. After he settled the bill, he looked at Dana. She was smiling at him with the sweetest smile he had ever seen.

"So, um, I'd still like to see those rooms at the Peninsula. I hear they're very nice."

David was a little surprised, but very pleased. "Actually, I think they ARE pretty nice. But you really should decide for yourself."

"Why don't you show me yours," she said with a smile.

David raised his eyebrows. "I show you mine, and you show me yours?"

Dana turned red for a second. "I meant your hotel room, of course." She paused for a moment. "For starters."

He smiled as he got up and extended a hand. Dana placed her hand in his as she stood up. David pulled out his phone to schedule an Uber, and it pulled up shortly after they got outside. Once they got to the hotel, David again took Dana's hand in his as they walked into the hotel and into the elevator. David stood behind her in the elevator and started rubbing her shoulders through her suit. Dana let out a soft sigh as the elevator suddenly dinged and the doors opened. Again, David grabbed her hand and led her down the hall to his room.

When she walked in, Dana was surprised by the size of the room. She knew this was a very expensive hotel, but the room was huge. She slipped off her suit jacket and placed it on the back of the chair.

"I'm going to use the bathroom, if that's okay," she said.

"Of course."

The bathroom was gorgeous, with both a large shower and a soaking tub. Two sinks with a huge counter made it look like a bathroom you'd want in your own house.

When she came out of the bathroom, she walked over to David and put her arms around his waist.

"How is the bed? Comfortable?" She was trying to play it cool, but she was incredibly excited and very wet. David pulled her closer, and she could feel his hard dick.

"I like it," he said, "but it's a personal thing. Maybe you should try it."

"Okay, but maybe I should take off my blouse so I don't wrinkle it."

"I don't think so," David said, shocking Dana into thinking she mis-read the situation. He continued, "I think I should do that for you."

Dana was relieved, and then nervous, as David undid her top button.

This was the part where Dana always got nervous. Of course, she had had sex before, but not a lot. And she was always embarrassed when she was naked in front of a guy. Intellectually, she knew she had a decent body. But all of her friends had bigger breasts than she did, and that always bothered her. She knew there were some guys who liked smaller girls, but every ad -- or porn clip -- made it seem like guys only wanted giant tits.

And then there was her last experience. It was a while ago, but she hadn't forgotten. The guy had a big dick. And the guy WAS a big dick. He penetrated her before she was ready or wet enough, and it hurt. And he didn't really care. He just started pumping away until he shot his load. And then he left. She lay in her bed crying, wondering why she invited the asshole back to her place.

And she knew some guys would get pissed at her because she didn't like giving blowjobs. She couldn't help it -- she just thought it was gross and didn't even want to try.

Even though she was still a little nervous as David continued to open her blouse, she somehow thought this time would be different. She almost felt comfortable letting him undress her. He bent down and softly kissed her left cheek, then her right. Then he undid another button and kissed her neck, which made her close her eyes. He undid one more button and spread her blouse, exposing her white lace bra.

He could see her very dark areolas peeking through, and he could see the beautiful shape of her small, firm breasts. He pulled her close and placed his lips on hers, first one very gentle, soft kiss, but then a much more passionate kiss, slipping his tongue into her waiting mouth. Dana let out a moan as he placed his hand on her breast and gave a gentle squeeze.

He pulled her blouse out from her skirt and finished unbuttoning her blouse, which he slipped off of her and laid across a chair. He licked her nipples right through the bra, which made Dana softly moan. He then walked behind her and unhooked and unzipped her skirt. As he lowered it, he kissed her bare ass, uncovered thanks to the thong she was wearing. She kicked her skirt to the side. David unhooked her bra but didn't remove it. He walked around to the front of her and then slowly slid the straps off her shoulder and her arms and pulled the bra away.