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The Wingman - Part 2

Alan begins his time as Andy's wingman.
"Dude, can you please promise me that you'll try not to give me a lot of shit tonight?"

Andy's favor seemed pretty genuine to Alan as they walked down the hallway to Karen's apartment. Alan's smile didn't help Andy's nerves. Considering how much Andy could drive him nuts, Alan loved that he was the one holding the power in this situation. After all, Alan had nothing to lose tonight. Andy stopped them before they reached Karen's door.

"Please? Not only will I buy you beer tonight, I'll do some sort of roommate appreciation deal if things go well tonight. You name it and I'll be cool with it."

Alan suppressed his smile and attempted to look as serious as he could.

"Okay, okay. Stop it with the nerves thing, you're making me get jittery just listening to you. I promise you, Andy, that I have no intention of doing anything to ruin tonight for you. You have my word."

"Thank you, man," Andy said knocking on the door to Karen's apartment. "I won't forget this!"

Karen's door opened and a very large bald man welcomed us.

"You guys must be here for Karen and her friends," he said letting us walk into the apartment.

"That would be us," Andy said.

"That's cool. I'm Charles."

Charles turned to look toward the bedrooms and announced, "Karen! Your dates are here!"

"Okay, thanks, Charles! Will be out in a bit," Karen yelled from her closed bedroom door.

The boys went through brief but friendly introductions with Charles as they each shook hands with his beefy paw of a hand. Alan looked at Andy in surprise as Charles walked into the kitchen.

"Didn't know she had a body guard, did you?" Alan asked.

"That's her roommate."

"Is she rooming with him for protection?"

"No, he and his boyfriend asked Karen to move in with them."

"Boyfriend, huh?" Alan smiled. "Between knowing there's someone out there for Charles over there and that you managed to meet Karen and score a date, I have to admit that life is just full of surprises for me tonight."

"Can I get you anything to drink? Karen told me to tell you she'll be ready in a little bit. Loosely translated, that means you might as well take a seat and relax for a while. Besides, the rest of the group for tonight hasn't arrived," Charles called from the kitchen.

"We're good," Andy called back. "We'll just hang out until everything's ready."

The duo sat down on opposite sides of the living room. Andy looked like a kid on a date in high school even though he really was twenty-one. He wore his older brother's hand-me-down button down long sleeve brown shirt with jeans and dress shoes. Andy's olive green army jacket didn't help the ensemble either. Alan admitted that Andy was trying to make an attempt, but to Alan he just came off as looking like a nervous under dressed prom date.

Alan was wearing a button down black shirt, jeans and dress shoes but somehow made it look a bit more dressy with the help of a black leather jacket. His laid back demeanor didn't really hurt him either. Just going to have fun, try not to pick on Andy too much and see what happens, he kept thinking to himself.

To his credit, Alan realized he didn't really look at his cell phone at all so far tonight. There wasn't really a thought of Amanda in his mind at all. Maybe Andy was right, getting out of his comfort zone was going to do him wonders.

Karen was still taking her time getting ready as Andy and Alan were getting tired of exchanging glances wondering how long they'd be waiting. A knock at the door grabbed both of their attentions. Charles once again played doorman, letting a very tall, completely beautiful blonde walk into the apartment. Both Alan and Andy were stunned, losing all ability to speak English for a few moments as this goddess graced them with her presence.

Charles yelled at the bedroom door again, "Karen! Cassie's here!"

Cassie looked to be amazonian in height, at least six foot tall, with long slender legs. Her golden blonde, wavy hair was a little passed shoulder length and framed her green eyes in a very attractive way. Cassie was dressed conservatively, partially because of the howling fall wind outside, but managed to have a very sexy and sophisticated look. She put both men sitting with her to shame.

Alan couldn't help but be surprised that this was Karen's sister, there was nothing physical about the two that would clue you in that they were related. For all of her beauty, Cassie's demeanor gave Alan the feeling that she was more nervous to be there, almost like she felt out of place.

Cassie, extended her hand in greeting to both Alan and Andy. Alan enjoyed the touch of her hand in his, noting how soft and smooth her skin felt against his own. It was a soothing feel and amazingly her presence had a similar feeling for Alan. Sure, she was beautiful but there was no way a woman like that would really see anything in him worth a second look.

"Oh, you're Cassie," Andy exclaimed in a way that made it sound like he found a missing piece to a puzzle he'd been working on for months.

"Yes, that's me, Karen's little sister. It's nice to meet you both."

Cassie sat down near Alan. Andy passed a look of amazement to his roommate. Alan simply shook his head hoping Cassie didn't notice it out of the corner of her eye. Even with no expectations going into this night out, Alan hoped he could at least pull off not being a gawking idiot when he was hanging out with a beautiful woman.

The bedroom door opening grabbed everyone's attention as Karen made her first appearance for the night. Andy stood up and the two hugged for a quick moment.

"I'm so sorry everyone. I just got off the phone with the rest of the group and they couldn't make it. It looks we are the entire group for the night," Karen admitted.

Cassie had an uneasy look on her face. Alan, too, felt a little off balance by the news. But he did tell Andy he'd be his wingman and Alan tried his best to be a man of his word when he gave it.

"It's no problem. We can still have some fun downtown," Andy announced, not wanting to let a snag ruin his evening.

Cassie still looked a bit let down and Karen took a moment to talk things over with her one-on-one. Alan and Andy just watched their conversation, the only communication they could understand being shakes and nods of the head and hands gesturing quite a bit. Finally, both gave each other a nod and Cassie looked almost resigned to her evening with her sister and two random guys.

"Okay, everyone ready to hit the town?" Karen asked, pulling on her jacket. They all walked toward out the door with Alan and Cassie taking up the rear. Cassie's six foot tall height made Alan's five foot seven frame feel slightly silly walking beside her. Taking it all in stride, Alan just said to Cassie, "Don't worry, you can help me pick on them while they try to impress each other all night."

Cassie looked at Alan and smiled.

Alan offered to drive the group downtown. Karen and Andy got in the backseat while Cassie sat up front with Alan. Karen and Andy were talking about random things that Alan wasn't really paying attention to as he just hoped to drown out the droning of Andy's voice that was louder than normal because of the car interior being a small space. Cassie had a look on her face that let Alan know she seemed to have the same opinions of her sister and this date.

After parking and braving the gusty night winds, the group sat down at the first bar, The Emerald Lounge. Andy was a man of his word, buying Alan and Karen some drinks. Alan wouldn't let Cassie buy her own drink, instead buying one for her. When the waiter brought by their drinks, Cassie gave a questioning look to Alan.

"You didn't have to do that for me," she said, leaning in to talk to him over the live jazz band playing across the room.

"I didn't do it because I had to, I did it because I wanted to," Alan admitted. "I could tell this wasn't the sort of night you were promised. This isn't how I expected my night to be, either. So I figured since you and I are unlikely company while these two have their date with training wheels, I can at least help by getting you a drink or two as a thank you for not leaving and making me the only chaperone."

With that he held out his beer bottle to her. She met his bottle with her own and the two made a silent promise that they had each other's back for the rest of the night. The tension began leaving Cassie, replaced with a subtle smile on her beautiful face. Alan even noticed a little twinkle in her eyes now and he couldn't help but be pleased that she was starting to enjoy herself.

Andy and Karen's conversation across the way was very exclusive. Andy's droning could be heard over the live music and it made Alan wince from time to time. Cassie giggled to herself when she noticed Alan's discomfort.

"So are you and Any good friends?"

"We're actually co-workers," Alan replied. "We're both graphic designers who hoped to move out of our parents' homes. I looked at myself in the mirror one day and just said 'Alan, you're twenty-two. Time to start living!' Just so happens Andy is along for the ride. Except tonight, where you and I are living in their world and along for the ride."

"I still live at home for now," Cassie admitted. "I'm trying to figure out what to do next."

"Well what do you do for a living?"

"I'm actually a model."

Alan tried his best to not look amazed but he was pretty sure his mouth was gaping open wide for a few seconds. Cassie looked slightly embarrassed by his response.

"I try not to tell many guys that because they look at me like I'm some sort of prize to be won," Cassie sighed, brushing her blonde hair behind her ear.

Alan couldn't help it. He was enjoying seeing that this beautiful woman wasn't full of herself just because she was attractive. Her self awareness made her seem much more vulnerable than he expected, making her feel very real and open.

"I didn't mean to gawk at you like that," Alan apologized. "I just never spent a night out on the town with a girl who was a model before. It's the first time I've been out in a while, the first time I'm a wingman and now the first time I've talked to a model."

"You know, models can come in all shapes and sizes. I mean, the woman who plays the lady selling dryer sheets on TV is basically a model if you think about it."

"I never thought of it that way. I guess I just had the popular version of model as my definition for years. Have you modeled in anything that I might have seen?"

"I've done some catalog work in the last few months. Nothing sexy, just clothing, just in case you were hoping to see me in my underwear," Cassie laughed.

"Well I wasn't figuring I'd be any more lucky than just sitting here in your company, Cassie. As crazy as it might sound to hear from a red blooded male, I'm okay not seeing you in your underwear."

Cassie laughed and Alan joined in. As their laughing died down they took a look at Andy and Karen who were still intensely talking. Alan leaned over to the blonde goddess next to him.

"So what do you think they're talking about?"

"Hmm… probably something artsy. Karen falls pretty easily for artistic guys. Her last boyfriend was a fine arts major in college."

"Before we came out Andy made me promise that I'd not pick on him or make him look silly in front of Karen."

"Oh really? Well as Karen's sister I can say that I never made a promise like that and enjoy giving her crap. If you slip around me, it can just be our secret."

Alan involuntarily grinned from ear to ear.

"So what do you think, guys? Ready to hit another bar?"

Andy's voice boomed over the band, shaking Alan and Cassie back to the real world again. Andy and Karen stood up from their seats and made their way toward the door.

"Just remember," Alan said to Cassie, "it's their world, we're just living in it tonight."

Alan helped Cassie get her jacket on and they followed the couple out into the cold.

The next bar they stopped at, The Crackerjack, was standing room only. Karen and Andy found a table to stand at and ordered a few more drinks for themselves. Cassie, meanwhile, walked toward the bar on the far wall, maneuvering through all of the bystanders with a graceful ease. Alan noticed many guys eying Cassie up and as she sat down a few guys tried to hover near her. One even walked up to her and started talking.

Alan couldn't make out what the guy was saying but it looked to him like he wanted to by Cassie a drink. Maneuvering with less ease through the crowd, Alan finally made it over to Cassie, standing behind her chair and managing to look tall in her company for the first time that evening. He could make out bits of the conversation over the music blasting through the bar.

"Would you mind if I bought you a drink?"

"No thanks. That's very sweet of you but I've got my drinks taken care of," Cassie said, gesturing to Alan.

The guy looked at Alan for a moment, sizing him up. Alan just gave the guy a goofy smile and waved at him.

"Hey, how's it going?"

The guy looked at Cassie again.

"That's cool. You have a good one," he said moving away from the bar.

Cassie looked up at Alan and smiled as Alan put his arm around the back of her chair.

"Sorry to ruin your evening by chasing him off. The love birds are lost in another discussion. I figured I'd just come over and try to look like a big, bald tough guy at the bar."

"That's okay," Cassie said, "sometimes bald can be beautiful."

Alan stopped for a moment, his mind taking a little time to process what just happened before reality caught up with him.

"Cassie, are we having a moment here?"

Cassie shifted herself slightly so her back was up against Alan's torso as she sat.

"Yes, I think we are."

After more drinks for Andy, Karen and Cassie, the group decided to call it a night and head back to the guys' apartment. The wind outside was blustery as the temperature lowered. Making the best of his chauffeur duties for the evening, Alan pulled his car up to the front door of the apartment building so his passengers could get out. Cassie just sat there not budging to leave.

"Aren't you planning on coming in to hang out for a bit?" Alan asked, slightly confused.

"You're not allowed to leave before I give you my number," Cassie simply stated.

"I'm not leaving. Well I am, but I'm leaving to park the car, Cassie. I'll be right up as soon as I can. You can give me your number then if you want."

"Promise?" she asked, her green eyes making Alan's knees weak.

"I promise. Now please, go with your sister and Andy so you can get in. I'll be right up. Get in out of the cold."

Grudgingly the blonde goddess opened the car door and made her way inside the apartment building with the intensely happy couple.

Alan pulled away and searched the streets for a parking spot nearby, only to luck into one three blocks away. By the time Alan got inside the lobby doors his hands, lips and cheeks were frozen. Still even with the weather treating him harshly, his growing excitement to see Cassie some more was helping warm Alan as the elevator finally got to his floor.

Opening the door of my apartment, Alan saw that Cassie was sitting on the couch watching a bit of TV. The smile Cassie gave him upon seeing him again helped Alan define the word beaming for the rest of his life. The whole room got a bit brighter with her enthusiasm. Alan smiled back at her and only hoped his smile conveyed the same bright enthusiasm.

Andy and Karen were in the kitchen pouring themselves rum and Cokes, then walked across the living room to retreat behind the closed door of Andy's room.

"Well I'd say that was a good night for them," Alan said, nodding toward Andy's room.

"I'd say it worked out well for everyone," Cassie smiled.

Alan couldn't help blushing a bit.

"Well, when you put it like that…"

"You've got Spider-Man on DVD! I love that movie! We have to watch this!"

Alan laughed. He loved the way Cassie caught him off guard with the fact that she loved Spider-Man as well.

"How can I say no to a woman who wants to watch one of my favorite movies," Alan said, popping the disc into his player.

"Turn off the lights, too! Get some proper movie watching atmosphere in here," Cassie requested.

Alan obliged.

Sitting down together, they both had a hard time not wanting to hold each other's hands or cuddle up close on the couch as the movie began. Alan reminded himself that he went into this night not looking for anything but that mentality was failing completely as this goddess's hands held his.

"You know what my favorite part of this movie is?" Cassie whispered.

"Tell me."

"When the Goblin laughs. It gives me the shivers every time he does it. It's creepy yet fun at the same time."

"Oh, you mean like this?" Alan asked, launching into the Goblin laugh softly in Cassie's ear.

"Stop that!" Cassie giggled, softly slapping Alan's arm. "That does stuff to me! Don't do it! We've only just met!"

"Okay, fine. But when it happens in the movie what are we supposed to do then?"

Cassie leaned her head back against my shoulder, cuddling close.

"We'll just have to jump that bridge when we get to it," Cassie smiled.

The night got later and later. Andy and Karen were still behind closed doors. Alan didn't want to think about what might have been going on in that room beyond the idea that maybe Karen decided to spend the night with Andy. The credits for Spider-Man began to roll. Cassie didn't try to get up from her embrace with Alan. Instead she rested her head against his shoulder and looked at him.

"It's pretty late," she sighed.

"Yeah, it's got to be at least three in the morning by now. Do you think the happy couple fell asleep in there?"

Alan nodded towards Andy's room. Cassie just shook her head, her hand reaching over to hold Alan's.

"I don't really want to know. She's my sister. The thought of whatever is going on behind that door gives me the creeps. I actually blame you for putting any indecent thoughts of her doing anything with your roommate into my head!"

"Trust me, I don't want to think about Andy doing anything with anyone in there either. It's a good thing we have each other, at least we don't have to suffer through this alone."

"I've got your back," Cassie said as she reached up to rub the back of Alan's neck as she laughed.

"Don't take this as me wanting you to leave," Alan began, "but if your sister's staying here with Andy, where does that leave you for the night? Driving back home?"

"Honestly, I'm too tired to drive at this time of night. I think I can trust you enough if you don't mind me staying here for the night. If that's okay."

"It's definitely okay. Did you want to use my bed for the night?"

"I don't want to put you out, Alan."

"No problem at all. You've got my back, I've got yours. The bed is all yours, no problem."

The two took their turns getting ready for bed, Alan lending Cassie a t-shirt and gym shorts for pajamas. Alan was the last out of the bathroom. Walking by his bedroom door he saw Cassie peering out at him again.

"Thank you again," she smiled.

"Not a problem at all. Sweet dreams," he said, heading for the couch.

And thus began the night of not sleeping.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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