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Story Notes:

I started this story excepting it to come out sillier than it did.  I think I kind of went easy on Michael, but that's partly because I have this theory that he's not quite as 'Michael' when the cameras aren't around.  And also because I'm not creative enough to come up with the kind of crap that Michael says. Please enjoy, and please leave a review!

Disclaimer: The Office, its characters, and its storylines are not my intellectual property.  Unlike terrible folk songs I wrote when I was a teenagers.  Those are all mine.

Jan sat in the aisle seat of row 14 and drummed her fingers on the armrest. The stewardess was taking entirely too long with her vodka tonic, and there was still another three hours left to go on this flight.

What the hell was I thinking?

Michael sat next to her staring out the window in amazement. It was as if the man had never been on airplane before. He’d only stopped asking her to join the mile high club after her fifth ‘no’, and her threat to get on the first flight back to New York after the plane landed. She knew she should be grateful for the silence, and she was, but the quiet was allowing her too much time to think.

This was so not a good idea.

The stewardess finally arrived with her drink and Jan quickly downed half of it in one gulp. She looked over at Michael again and caught herself smiling.

Damn it.

He’d fallen asleep with his head against the window and his mouth was slightly hanging open.

At least he doesn’t snore.

For all she’d tried to deny it, there was something about him that simply made her happy. Made her feel like a little girl again. She’d never had much luck with the men in her life. Her father had been verbally abusive and incredibly strict; very no nonsense. He’d always been too busy with work to make time to play with her, or to talk to her, or to show her any kind of affection. Gould wasn’t much different. He spent most of their marriage ignoring her completely, and when they did talk, it wasn’t talking. It was yelling. It occurred to Jan that the short time she’d spent with Michael was probably the most fun she’d ever had in her life.

Oh dear God, that is pathetic.

Jan continued to sip her drink, allowing her mind to wander a bit. She’d met Michael for the first time years ago, on her third day with Dunder Mifflin. The company hired her to come in and be a sort of liaison between the branches and the corporate executives; to try and open more lines of communication. Michael had just been promoted to manager a few weeks earlier, so her meeting with the Scranton branch that day was a very important assessment of how things were going. She had been immediately struck by how classically handsome he was when he extended his hand and introduced himself upon her arrival.

And then he opened his mouth.

Everyone filed into the conference room and Jan started setting up her visual aids in preparation for the meeting. She introduced herself and ran through her rehearsed spiel on corporate relations, sales, and the company’s commitment to employee retention. She opened the meeting up for questions and sat down at the table with everyone else. She always tried to make an effort to seem at their level, and make them feel comfortable. She took a sip from her coffee mug and immediately felt something warm and wet spreading across her chest. She looked down and realized that yes, it was coffee, and yes, she now had a big brown stain covering her breasts and seeping into her expensive white silk blouse.

She started to stand up when Michael leapt from his seat and ran out the conference room door. He returned seconds later with a damp paper towel. Kneeling in front of her, he began blotting the stain away, announcing with great concern that coffee has been known to cause breast cancer, and it should never be so close to a lady’s breast. She stared at him, a bit shocked. She wasn’t used to people taking care of her like that. It felt kind of nice. So nice in fact, that it took her several moments to realize how utterly inappropriate it was that she was allowing this man to be anywhere near the vicinity of her breasts during a business meeting, and in front of their employees. She stood up and pushed him away, saying thank you but also making it clear that he should stop. He grinned and held up both hands in surrender, returning to his seat. As she excused herself to the restroom to finish the job Michael started, she couldn’t help but smile. There was sweetness to this man.

Maybe I’m not so crazy…

The pilot’s voice snapped her back to reality as he announced over the intercom that they would begin descent in thirty minutes. She inhaled deeply, looked over and saw that Michael had woken up. There was a goofy grin on his face. She told him no before he could ask again, but he stepped over her and headed for the bathroom anyway. Or as he called it, their flying chamber of love.

Forty-five minutes later the plane touched down and they made their way through the airport and into a cab without incident. Michael was practically jumping up and down in his seat as he instructed the driver to take them to “Sandals Jamaica, my good man!”

Jan was pleasantly surprised when they got to the hotel. The place was actually really nice, the room was big and tastefully decorated, and the view outside their window was incredible. She was curious how much Michael had spent on the tickets. They unpacked and headed down to the restaurant in the lobby for some breakfast.

Am I actually enjoying myself?

After returning to their room for a quick nap, Michael managed to coax Jan into taking a scuba lesson with him. Sure she was embarrassed when he started asking the instructor inane questions about jelly fish and whether or not you can harvest them for sandwiches, but all in all the scuba diving had been fun. And she’d gotten to see Michael without his shirt on.

I had no idea he was so built.

After the lesson they retreated to the beach, where Michael carefully laid out a towel for her on the sand. “My lady,” he’d said, motioning for her to lie down. She did, and he laid out a towel for himself next to her. She closed her eyes and began to relax, breathing in the smells of ocean and beach, enjoying the feel of the sun beating down on her. She realized that she must have fallen asleep only after she felt Michael’s hands on her thighs.

She shouted at him, more out of embarrassment that they were in public more than anything else, but quickly realized that he wasn’t trying to fondle her. She didn’t know how long she’d been asleep, but it was long enough for her back and legs to be showing the signs of a bad sunburn. Michael had noticed, and as he later told her, he couldn’t sit there and do nothing as her beautiful skin fried like bacon in a Foreman grill. She calmed down and closed her eyes.

He’s actually pretty good with his hands.

Michael rubbed the sun block into the back of her thighs, shoulders, and her arms. He was just being sweet, and she knew he wasn’t trying to seduce her or anything, but damn, was it turning her on. She rolled over, faced him, and squeezed a bit of sun block into his hand. She pointed to her chest and his eyes bulged out of his head. She nodded to tell him it was okay, but shortly after he put his hand there she realized that they should probably take this up to their room.

Dear God, I’m going to sleep with Michael Scott.

The second they got behind a closed door, she pulled off her bikini and threw it on the floor. She ignored him when muttered, “Boobs,” and instructed him to take off his pants. He giggled and said that while he really wanted to introduce her to Michael Jr., shouldn’t he go get some raincoats first? She was befuddled, and it took her several seconds to realize that by raincoats, he meant condoms. “Yes, go, and hurry,” she’d told him, immediately breaking into the mini bar after he left. She was stunned to see that the mini bar wasn’t quite so mini. Before her sat full sized bottles of vodka, gin tequila, and rum. Sandals had even provided them with mudslide and margarita mixes, a martini shaker, and a blender.

She was halfway through her second pitcher of ice cold margarita perfection when he flung the door open and entered proudly shouting, “Trojan man!” Horrified that anyone in the hallway might have heard him, she pulled him inside and shut the door. He was holding a large paper grocery bag. When she asked him what was in it, he calmly answered, “Condoms,” and set the bag down on the bed, heading for the bathroom. Jan walked over and looked inside. Sure enough, the entire bag was filled with boxes and boxes of Trojans, ribbed for her pleasure.

 

This man is insane.

 

When he emerged from the bathroom, Michael was wearing nothing but a smile. He walked over to her and took her in his arms. She could tell he was trying to make this a romantic moment, but she was in no mood for romance. Pushing him towards the bed and eventually on top of it, Jan pounced on him. She feverishly covered his face and neck with kisses, and once Michael Jr. was standing at attention, she ripped open one of the raincoats with her teeth and slapped it on him.

 

She quickly mounted him and began riding him like this was her last night on earth. She would have been content to keep on going that way for hours, but at some point Michael had lifted her up and rolled over on top of her. He was trying to slow things down, and softly pressed kisses into her neck and down her chest.

 

Oh my God.

 

Michael was surprisingly good at this. It reminded her, in a way, of that night at Chili’s when he’d effortlessly landed the sale with Christian. How can a man be so boisterous about the things he is so terribly bad at and yet, so humble about his true talents? She was lost in her thoughts but quickly came to when he slowly reentered her. She realized he was staring deeply into her eyes. They came together in that position, and as he finished Michael softly whispered her name. She was completely blown away.

 

Coming here was the best decision I ever made.

They spent the rest of the week enjoying all Sandals had to offer, including Jamaica’s largest fresh water pool. Jan quickly developed a level of patience with Michael that she’d previously thought impossible. He would constantly say the wrong thing at the wrong time, usually in front of the wrong people, but it didn’t matter to her anymore. She was starting to see the man inside him. The man who was terribly insecure and unsure of himself at times, but also the most caring and good intentioned man she’d ever known.

I’m falling for him.

On their last night in Sandals she was moving about the room, preparing to leave the next morning, but not really wanting to. She spotted the paper bag of Trojans in the corner and peeked inside. There were still several boxes left, but the two had managed to go through half the bag.

Best. Decision. Ever.

She awoke the next morning in a panic as the phone rang. The concierge politely informed her that their taxi was waiting outside to take them to the airport. She hung up the phone and screamed at Michael to wake up, they were going to be late, and didn’t he say he’d set the alarm on his watch? Still half asleep he mumbled that maybe his battery had died, and that he was sorry. Jan furiously pulled on the nearest articles of clothing she could find and Michael did the same. Luckily, she had spent that time packing the night before, and they were out the door in less than ten minutes.

There was no way they could miss their flight. If both of them missed work the next day after taking a vacation during the same week, it was going to look highly suspicious. Jan was beginning to feel the stress that typically consumed her life begin to boil back up inside her.

This was a mistake.

She reached in her bag for a cigarette and just as she was about to pull one out, Michael placed his hand on top of hers. “I’m sorry,” he’d said, “I did set my watch, I don’t know what happened.” She looked over and was horrified to see tears sprouting in his eyes. She tried to assure him that everything was okay, but he kept talking. His voice squeezed out through his closed throat. “This was the best time of my life, and now I’ve gone and ruined it. I am such a scum bag.” She eventually had to kiss him to make him stop talking. As she pulled her face away from his she whispered, “It was the best time of my life, too.”

She slipped the cigarette back in her bag, not really feeling like she needed it anymore, and stared out the car window, content. And although she rolled her eyes when she heard him ask, “Who’s my Jamaican sun princess? Who is she, who is she, who is she?” Jan couldn’t help but smile as she answered, simply, “Me.”

Me.

Chapter End Notes:
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