His Sisters Friend

The meeting broke up, and everyone started to walk out of the conference room. Matt pulled his mobile phone out of his pocket to take it off silent mode, and he noticed a missed call from his sister. He also noticed a text message with the same time stamp.

"Nothing critical, but please call me when you get a chance."

When Matt got back to his office, he hit the Favorites entry for his sister.

"Hi, Matt, how are you doing?"

"I'm fine, Lauren, what's up?"

"Do you remember my friend Briana?" Lauren asked.

"Brianna... Brianna. Gee, Lauren, I'm not sure. I mean, how do you expect me to remember your best friend since you were in kindergarten, a girl who practically lived at our house, slept over almost every weekend, and lived four doors down. If she lived THREE doors down, I might remember her. But FOUR doors... that's kinda' tough."

"Okay, okay," Lauren said while laughing. "It's just that you haven't seen her in a long time. You stopped living at home, what, after your sophomore year of college? I was only a junior in high school."

"Yeah, but that leaves about 12 years when she was like a roommate. And I probably saw her a few times when I was home for holidays. Anyway, what about her? How is Brainy Brianna?" he asked, using a nickname he made up for her years ago.

"Actually, she's still kinda' brainy. She just finished a Master's degree at MIT, and she accepted a job in Chicago. She's flying out next week to find an apartment. The company set her up with an apartment search company, but she doesn't know anyone in Chicago. Any chance you could have dinner or drinks with her one night just so she doesn't feel so alone?"

"Of course," he replied. "When is she coming?"

"I think she gets in Tuesday, and she's looking at places Wednesday, Thursday and Friday."

"Send me her cell phone number, and I'll contact her to find out her travel plans and where she's staying."

"Thanks, Matt, I really appreciate it!" Lauren replied. "I almost feel bad about telling everyone you're an asshole," she said with a laugh.

"Wouldn't expect anything less from you, Lauren. I gotta' run. I'll talk to later. Send me Bri's info."

"Okay, thanks. Love you."

"Love you too, Lauren."

Shortly after the call ended, Matt received a text message with Brianna's contact information. He saved the information and immediately sent her a text:

"Hi, Brianna, it's Matt. Lauren told me about your trip next week. Let me know your flight time, when you're visiting apartments, and where you're staying, and we'll make some plans."

Later that evening, Matt got a message from Brianna with all the information. He proposed meeting her at the hotel Tuesday evening at 6:30 and going out to dinner. She replied:

"Thanks, Matt, that would be great! See you then."

Tuesday evening, Matt left the office at 6:00 and walked over to Brianna's hotel. Although Chicago can get incredibly hot and sticky in June, this was a beautiful, low-humidity day, so it was a very pleasant walk. Matt entered the hotel through one of the side doors, and he saw Brianna from behind. She was in the lobby facing the main doors, so she didn't see him. He walked up behind her.

"Excuse me, ma'am," he said, and she immediately turned around. "I'm looking for a geeky, skinny, 17-year-old with braces and glasses. But she has that same beautiful red hair as you, so I thought you might be related or you might know her."

Brianna had a huge smile on her face. Matt realized it really had been quite a while since he had seen her, and she had really become a beautiful woman. She was still thin, but not skinny. She was about 5 foot 6, with curly, red hair that went below her shoulders. He knew she had bright blue eyes, but her makeup made them look even better than he remembered. He loved the few freckles over her cheeks. Her breasts were on the small side, but perfect for her body.

"I'm sorry, sir," she said, "but that girl left quite a while ago. I'm afraid you're stuck with me."

"Actually, I'm quite pleased to be stuck with you. Welcome to Chicago, Bri," he said with a smile.

Brianna returned the smile and wrapped her arms around Matt, who returned the hug.

"It's really nice to see you, Matt. It's been quite a while. Thanks for being a familiar face in a strange city."

"It's great to see you, too, Bri. And it's a pleasure to welcome you to Chicago. How about we grab a drink at the top of the Hancock building -- it offers a great view of the city."

"Sounds good," she replied.

The walked a few blocks to the Hancock Building. Matt knew it wasn't officially called that anymore, but that's still the way 90% of people referred to it. Along the way, Matt pointed out a few special buildings that had architectural significance or housed famous companies.

They rode the elevator to the 96

th

floor. Since it was a Tuesday, the place wasn't overly crowded. They grabbed some stools near the northwest corner, providing a beautiful view of the city. They ordered over-priced drinks, but the price was well worth the view. For the first few minutes, Matt pointed out various buildings and sites. Brianna thought it was beautiful and had a constant smile on her face. After a short time, Matt walked her over to the Southwest corner so she could see the other half of the city. In both corners, Matt pointed out some of the neighborhoods she would probably see with the rental agent.

After the initial "tour" of the city from 96 floors up, Brianna and Matt started catching up. She told him about the company she was going to be working for and about her job. He told her about the neighborhood he lived in, his job, and what he liked doing in the city.

Brianna really enjoyed talking with Matt. He was funny, self-effacing, and smart. She also noticed he was a really good-looking guy.

Matt really enjoyed talking with Brianna. She was funny, incredibly smart, and had lots of interesting experiences. He also noticed she was a really good-looking woman. This was not the 17-year-old skinny girl he last saw in the neighborhood of his youth.

After talking for a while, Matt suggested they get some dinner. He said there was a nice restaurant along the river which had a wide variety of items, and asked if that would be okay.

"I'm in your hands," Brianna said, suddenly thinking for just a moment how nice it would be to be in his hands. "I trust your recommendations. And if you poison me, you'll have to deal with your sister."

Matt laughed. "Well, THAT'S an incentive to make sure I take good care of you."

Since it was a beautiful night, they walked to the restaurant. They continued catching up as they walked and throughout dinner. They each told funny stories about their common link, Matt's sister and Brianna's best friend.

"Hey," Matt said at one point, "can I ask you a question?"

"Of course," Brianna replied, surprised by Matt's serious tone and funny look.

"I probably wasn't always the nicest guy to my sister, especially when I started high school and you guys were like 11 years old." Then he paused for a second. "Was I an asshole to you?"

Brianna burst out laughing.

"Actually," she said when she finally stopped laughing, "you were always really nice to me. You and your sister were usually pretty good with each other, but she was your sister. So, of course you two had arguments. But you always treated me well. And god knows I was at your house a LOT! You could have gotten sick of me -- and maybe you did -- but you were never mean to me. Even though I didn't spend nearly as much time at any of my other friends' houses, their older brothers WERE sometimes jerks to me. But not you. It's something I always noticed and appreciated. So, I'm a little late with this, but thank you."

Matt chuckled. "It's not often I get thanked for not being an asshole. Guess you had pretty low expectations of me."

"No, no, no," Brianna objected. "I just appreciate that..."

Matt cut her off.

"I'm teasing you, Bri."

They both laughed and moved on to some other topics.

After dinner they grabbed a taxi back to Brianna's hotel.

"Have fun looking at apartments tomorrow," Matt said. You've got my number, so call if you have any questions."

"Thanks, Matt. And thanks for tonight. It was great."

She put her arms around him and hugged him very tight. Matt was a little surprised but was happy to return the tight hug. When she finally broke it, they both looked at each other in silence for just a couple of seconds.

"It was great to see you, Bri. We'll talk."

"Thanks, Matt. Great to see you, too."

Matt waited until Bri got inside the hotel. Just before she walked in the door, she turned her head. Matt was watching her, and she smiled. Then she disappeared in the revolving door.

Matt stood there for just a couple of seconds. He couldn't believe how much fun he had tonight.

The next day at 4:30, Brianna's phone rang. She smiled when she saw it was Matt.

"Hi there," she answered.

"Hi yourself. How was apartment hunting?" Matt asked.

"It was really good. I saw a number of places that I could be very happy in. We're going to another neighborhood tomorrow -- Lincoln Park."

"Great. Do you want to have some dinner tonight and talk about what you saw?" he asked, hoping he wasn't bugging her.

"I'd love that, thanks!" she said, with a huge smile on her face. Matt could almost hear the smile in her voice; it made him happy.

"Okay," he said, "I'll swing buy your hotel at 6:30, it that's ok."

"Perfect. Thanks," she said. "See you then.

Brianna was a little surprised Matt wanted to see her again, but it was a very pleasant surprise. She decided to take a shower and fix herself up. After showering, she put on some make-up, and she thought she looked pretty good. She put on jeans and a crop top and then headed downstairs.

She was waiting in the lobby when she saw Matt walk in through the main hotel doors. She smiled at Matt as she stood up, and he returned the smile. When he got to her, she threw her arms around him and gave him a tight hug. When she broke the hug, she gave him a quick kiss on the lips. Matt was surprised but very much enjoyed the greeting.

"Wow, Bri, you look fantastic!" he said.

"Normally I'd say 'thank you', but the way you said it, I'm thinking I should be pissed that you're so shocked I can look good."

Matt started laughing. "No, not shocked that you CAN look good... just letting you know you were EXTREMELY successful with whatever you did."

"Okay," Brianna said. "In that case, I'll say thank you."

It was another nice evening, so they ate at an outdoor restaurant on the roof of one of the hotels in the area. Brianna told Matt about the various places she looked at that day. She took some papers out of her purse to show him some information.

"Whatever you do," Matt said, "make sure you don't rent a place in the River North neighborhood."

Suddenly, Brianna got a sick look on her face. Before she could say anything, Matt started laughing.

"I'm just kidding," he said. "I saw the address on that first sheet of paper, and I know it's in River North. Actually, it's a great neighborhood."

"Don't do that!" Brianna said with mock anger. "You got me really nervous."

She showed him a few apartments and the pros and cons the agent / consultant pointed out.

"Sounds like she's doing a good job of looking out for your interests and giving you good advice," Matt said. "I look forward to hearing about what you see tomorrow."

They spent a long time at the restaurant because they were both having a good time. The conversation flowed easily, they agreed politically, they were both intelligent, and there was a lot of laughter. As they walked back to the hotel, they walked very close to each other.

As they got to the top of the driveway, Brianna stopped, so Matt stopped and turned toward her. She put her hands on his neck, but didn't pull him in for a hug. He instinctively put his hands on her waist.

"You've already made my move to Chicago a happy event -- and I haven't even moved yet," Brianna said. "I've really enjoyed the last couple of nights."

Matt started to tell her how much he liked it, too, but before he could, Brianna pulled his head down as she stood on her tiptoes and kissed him. It wasn't just a quick peck; it was a real kiss. Matt was more than thrilled to kiss her back, and when she pushed her tongue into his mouth, he was more than happy to accept. He wrapped his arms further around her and pulled her tight against his body. She felt his hard dick press against her, which made her use her tongue to play with his even more quickly.

After a minute, she broke the kiss and pulled her head back. She had a big smile on her face.

"That was nice," she said. "I hope you weren't appalled."

Matt let out a loud laugh.

"Wow, if my response made you think I was appalled, I've really got to work on my kissing technique!"

This made Brianna laugh, too.

"No, actually, I think your kissing technique is quite good. I was just afraid... I don't know."

Suddenly Brianna was a little embarrassed and looked down. Matt put his hand under her chin and lifted it up to look at him as he smiled at her.

"I wasn't appalled. I liked it."

Then he leaned down, pulled Brianna against him, and they started kissing again. Not quite as long, but still very passionate. And Brianna still liked feeling his hard dick push against her.

When they stopped kissing and Matt stood up straight, they both looked at each other for a second.

"I'd better go in," Brianna said. "Good night, Matt. Thanks for everything."

"Good night, Bri. Thank YOU for everything."

Brianna smiled, gave a little wave, and walked into the hotel.

'Holy shit.' Matt thought to himself, 'I did not see that coming. Damn, that was nice."

The next morning, when Brianna woke up, there was a text message waiting for her from Matt.

"Good morning. Hope you slept well."

Brianna smiled, then replied.

"A little difficult time falling asleep... but I slept like a baby."

Five seconds later, her phone rang with a call from Matt.

"Good morning," she answered.

"Good morning to you. I think I'm breaking every rule in the book by contacting you so soon, but can I see you again tonight after you're done looking at apartments? I'll understand if you want a night off."

"Hmmm, I don't know," she said. "I could sit in my hotel room all by myself and eat a shitty dinner from room service, or I could go out with a really nice guy and have some great conversation. Can I think about it for a while?"

"Sure, sure," he said, "take your time. I know it's a tough decision."

"You know, I feel sorry for you, so sure, I'll spend some time with you." Then she laughed a little.

"Excellent," he said. You think you'll be done by 6:00?"

"I'm sure," she said. "Amy usually finishes by 4:30. See you at the hotel?"

"I'm looking forward to it," he said.

"Me, too, Matt. Thanks."

Each of them hung up, and each of them smiled. These last couple of days were an unexpected surprise to both.

Matt showed up at the hotel in a taxi, and Brianna was sitting on bench in front of the hotel. He thought she looked great. She was wearing a light-blue simple top with spaghetti straps and a short, thin navy-blue summer skirt. As he walked up to her, she stood up, wrapped her arms around his neck, and gave him a short, warm kiss on the lips. Then they hugged each tight.

Matt broke the hug first.

"As much as I'd like nothing more than to continue hugging you," he said, "we've got to get going."

"Get going? Where?"

"A surprise," he responded. Then he hailed a taxi. When they got in, he told the driver the name of some theater Brianna had never heard of.

When the taxi pulled up to the theater, Brianna had a big smile on her face. This was a performance of

A Chorus Line

.

"Oh my god," Brianna said. "This is my favorite musical EVER?"

"Really?" Matt said. "Lucky guess on my part."

"I don't suppose you've been talking to your sister, have you?" Brianna asked.

"My sister? No, we never talk. I don't even like her," he said with a straight face.

"Uh-huh," she replied. "Guess you did just get lucky."

They went inside, and Matt walked over to the Will Call window. He got their tickets and walked back toward Brianna. He put his hand on her lower back as he directed her toward the door. She closed her eyes for just a second, enjoying the feel of his hand on her back.

"It's not a Broadway cast, but they're supposed to be pretty good. I hope you like it," Matt said.

"I'm sure I will!" Brianna replied.

They took their seats, and as soon as the opening number started, Brianna had a smile on her face. At one point she looked at Matt who was looking at her, smiling. She grabbed his hand in hers, interlaced her fingers, and placed both hands on her lap as she returned her attention to the stage.

At intermission, they stretched their legs and walked into the lobby. Brianna could not wipe the smile off her face.

"This is fantastic," she said. "You have no idea how much I appreciate this."

"I'm glad," Matt replied. "I like pleasing you."

Brianna suddenly pulled Matt in for a hug, which surprised him. But he was happy to pull her tight against her body.

"You make me feel special," she whispered.

"You are special," he whispered back. "I like making you feel good."

Brianna felt him starting to get hard, and she pulled him even tighter against her body.

The lights in the lobby started flashing, so Brianna broke the hug. She grabbed Matt's hand and held it as they walked back to their seats for the second act.

Brianna smiled during the entire second half, too, thoroughly enjoying the play. After the finale, she jumped to her feet and applauded very loudly. Everyone in the theater seemed to enjoy the play, and most people were standing as they applauded. Finally, they walked outside.

Matt looked at his watch and said, "I made reservations at a local restaurant around the corner. We're right on time. I hope that's okay."

"Of course," Brianna said as she smiled.

They walked hand-in-hand to the restaurant and were seated right away.

"You know," Brianna started, trying to sound as sarcastic as possible, "considering you don't like your sister, it's awfully nice of you to give up three nights of your time to help her best friend."

Matt reached across the table and grabbed each of her hands in his.

"My commitment and favor to my sister was for ONE night. Everything after that was on my own. And it's all because of you. I LOVE every minute I've spent with you. You're incredible."

Brianna blushed at his words as she looked him in the eyes.

Thank you," she said. "You're pretty incredible yourself. You have no idea how good you make me feel."

"Like I said before, I like making you feel good."

They both sat quietly for a minute, just looking each other while Matt was still holding her hands across the table. As their waiter started to walk by, Matt called him over. He pulled out his cell phone and looked at Brianna.

"We definitely need a picture for my sister. We can send it and say 'Wish you were here.' "

Then he turned to the waiter. "Can you take a picture of us, please?"

"Of course," he replied.

Matt slid out of the booth and moved over to Brianna's side. He got right against her, with his leg touching hers. Then he lowered his hand and put it on her leg. But because her skirt had ridden up as she slid into the booth, his hand ended up on bare thigh. She sucked in a little air, surprised by his touch.

"Sorry," Matt said, and started to move his hand. But Brianna grabbed it and put it back on her thigh - maybe even a little higher than where he had it. Matt was surprised she did that.

"Don't be sorry," she said. "You just surprised me. I like it."