Title: Complications

Disclaimer: Not mine. I am just "commandeering" it.

Rating: PG-13

Warning: Slash, crossdressing,

Pairing: Penson

Summary: Doug makes a dare. Tom pays. Slowly they realize how complicated life can be.

Complications

Tom had just finished his paperwork when he spotted Doug, Harry, and Booker watching football. He slowly made his way over to them.

"GO! YOU'RE AN INCH AWAY FROM GLOR-AAARGH!" Doug pounded his fist into the cabinet beside him. Booker reached a hand out while Harry laughed and shook his head at both of them. Doug dug out some money and slapped it into Bookers hand.

"Thanks pal, it's nice to now you aren't a sore loser," Booker smirked as Tom reached them.

"Who's playing?" Tom asked falling into a the chair Penhall had vacated in his quest to destroy inanimate objects.

Doug snorted and gave Hanson an odd look.

"What?" demanded Tom, not at all happy about the looks of amusement he was receiving from his friends.

Doug turned to Tom, "What do you know about football?"

Tom glared at Doug, "I knew enough to play it with you on one of our cases."

"There isn't much that you can do to mess up in less than a minute, but somehow you managed it."

"That's not true," Tom retorted while the tips of his ears burned with embarrassment. How can he remember that!

"Ha! See, if we bet on this game you would lose," Doug grinned triumphantly.

"No I wouldn't," Tom replied feeling a little humiliated. He didn't pay attention to the games like the others. What's the point? He'd hear a play-by-play from Doug during his attempts to reenact it by the next day anyway.

Doug's grin grew wider while Tom watched in trepidation. This can't be good. "If you're so sure of yourself buddy, how about we make a wager?"

"Like what?" Tom asked warily.

"If you say the wrong team is going to win, you have to wear a skirt and all the rest of those things women wear, and I mean all of it"

"What! Doug there is no way I'm going to put on a dress again!"

Booker broke into their standoff for a moment staring at Tom, "Am I missing something here? When did you wear a dre-"

"Come on Tom, if you know you'll win then you won't have too." said Doug looking extremely pleased with himself. Booker was at his side squinting at Tom as though he was trying to picture him in a dress.

Tom stopped to think. If he backed down now, Doug would know he wasn't sure of himself, but if he lost he would have to dress up like a girl. He would never live that one down. They still gave him grief over last time, so his best chance was to hope he picked the right team. It's fifty/fifty after all.

"Alright," he sight defeated. "Who's playing?"

Judy sighed as Tom balked at the sight of the skirt. "It's not that bad Tom. I wear them all the time. Besides you had to do it once before."

Tom glared at the skirt as though it had stolen his bowling ball. "I had to wear a dress once. ONCE! It was for an assignment, and I still remember how horrible pantyhose is."

Judy smiled at her hapless friend. "Well they say that in every cloud there is a silver lining." Tom snorted, but she continued anyway, "You could use this to your advantage."

Tom raised an eyebrow skeptically, "and how would I do that?"

"Simple, we blow their minds and they'll end up being the embarrassed ones." She replied with a wicked gleam in her eyes.

Tom remained skeptical, "Come on Jude. They'd just laugh about me making a good-looking girl."

She leaned forward to whisper conspiratorially into his ear. "Who would be more embarrassed in this scenario."

Tom's eyebrows were in danger of disappearing into his hairline as her twisted plan dawned on him. Then slowly a wicked grin began to grow. This was going to be fun.

Judy turned around, "Ok, I had better get the waxing strips…"

"WHAT?"

Ok, so maybe not much fun.

It had been two painful hours (only some physical pain), but now Tom and Judy were ready to meet up with the guys at a bar. Well at least the guys who weren't cross dressing and glaring at the review mirror hard enough to burn a hole in it.

"Cheer up Tom. You'll survive."

"I'll be the first man to actually die of embarrassment." he mumbled watching the people on the sidewalk. They were so happy and normal… Well come to think of it they weren't too happy looking, and the drunk lying in the gutter couldn't be very normal… at least he hoped not.

"We're here." Judy announced swinging the door open while they got out. "Time to make our grand entrance." She noticed Tom trying to retreat back to the car, though, and grabbed his hand to stop any further attempts at escape. "Come on you've gotten this far."

Tom winced as he remembered the leg waxing. "You're right. I can't back out now." He took a deep breath and focused on the bar door. "Let's do it."

Pride can be a strange thing, he decided, especially when it leads to wearing a skirt to defend manliness.

Penhall, Ioki, Booker, and Blowfish were all at the bar waiting for Judy and Hanson. Ioki and Penhall had already filled Booker in on the kidnapping case when Tom had to pretend to be a woman.

Penhall laughed, "He had actually looked pretty convincing too. Of course he did end up in Jump Street for his baby face."

Their laughter was silenced when they saw who walked through the door.

First came their colleague Judy Hoffs. However, what walked in behind her was a complete surprise. They had been expecting Tom to be wearing a conservative dress like the one from the kidnapping assignment. What they had walking into the bar now was a young man dressed in a short leather skirt, knee-high black boots of the same material, and a blood red shirt. In short they were shocked.

Doug stared as his best friend sauntered over to them. Sure he had noticed the Tom was a good-looking guy, he had always attracted a lot of women, and the last time he'd had to cross-dress a man from Homicide had sent him roses. He had also noticed that he looked like a pretty good punk when he tried. What he wasn't prepared for was finding out that underneath Tom's cover-all clothes was an extremely hot body.

Just before Tom reached them Jude stage whispered, "Your mouths are open." They quickly rectified that problem as Tom arrived.

"You all alright?" Tom questioned them with a smirk upon his face. "You all look like you've seen a ghost." How could he be so calm? Doug wondered. He was in full drag in a bar!

Before Doug could come out of his shock long enough for a clever retort Judy spoke up. "Well, I guess I'll leave you boys alone now. I have work to do and my job as makeover artist is finished," and with that she left them to come back to their senses.

Blowfish who had regained the use of his mind long before the others spoke first, "Wow, I wouldn't have dressed like that if I were you. Once the guys here start to get drunk they'll become real pests."

"Don't worry I can take care of myself," Tom joked, "besides they'll notice I'm not a girl from the get-go."

Doug turned around to see many of the other inhabitants of the room staring at his partner. Great, now he'd have to protect Tom from horny drunks. "Tom," he started unsure of what to say, "Why are you dressed like that?"

Tom looked up at him with a frown starting between his brows, "because of your dare Doug. I'm not going to forgive you for it by the way." Tom shifted for a moment, "The leg wax was almost as bad as a bullet." He added with a glare directed at his friends.

Luckily Harry saved him from answering, "We just didn't think that you'd come dressed like this," he gestured at Tom's attire.

Tom shrugged a bit of a blush forming on his cheeks, "It was Judy's idea." He chewed on his lip for a moment before his head collapsed in his arms as he muttered indistinguishably.

"What?" Doug asked looking concerned, this was after all very out of character for Tom the poster boy of straight-laced-and-modest.

"I can't believe you made me dress like this and Jude was there." Tom said before he muttered, "some friend."

Doug stared a him, "Wait, Tom I didn't make you dress like this," he exclaimed motioning helplessly at Tom's clothing. "That was Judy."

Tom glowered at him with eyes that turned darker from the mascara surrounding them, "but you were the one who made me cross-dress!" he snarled just quiet enough that his voice didn't reach the bars patrons.

Surprisingly it was Booker that came to Penhall's rescue this time. "Look Tom, I know this must be embarrassing for you, but the others here haven't noticed that you're a guy yet, so why don't I get you a beer and you can try to calm down."

Tom's head swung to Booker at this. When had Booker ever cared if he was alright before? He rarely called him Tom as well. Of course he might just be trying to patch things up. They had to work together after all.

"Sure Dennis, that sounds alright," he said managing a smile. Maybe this wouldn't be so bad after all. One of the things he feared the most about this was the jabs he was sure to receive for this outfit from Booker. Without whatever painful comments he could create this would be a lot less difficult to get through.

Booker nodded with a smile as he headed to the bartender to order their beers.

Blowfish decide to leave while he had a chance. "Well it was fun and all, but I gotta get home to my wife." Seeing that Blowfish was leaving Harry got up as well. "Yeah I have to get up early tomorrow. It's a Friday and unlike you two I have an assignment."

Tom nodded absentmindedly as he puzzled over Booker's change of character.

Doug stood up quickly and followed Harry as he turned around the corner. Once they were out of Tom's line of sight he grabbed his friend and spun him around by the back of his jacket. "Iokage you can't leave me here."

Harry yanked Doug's hands off his jacket, "Doug I'm serious I do have to go!"

"But you can't leave me here with Hanson in drag and Booker." Doug pleaded adding his best puppy-dog-eyes.

"I am really sorry. I know it will be awkward, but I can't stay. I have work tomorrow." With that he left the bar.

"Harry!" Doug cried futilely. Taking a deep breath he went back into the war zone. Booker had already come back to their table and there were five beers in front of Dennis and Tom. Two of which were currently being nursed by the tables occupants.

"Have I missed anything?" Doug asked as he settled in between the two. As Tom shook his head Doug noticed a scowl that had appeared and quickly disappeared on Booker's face. Shrugging it off he reached for one of the three untouched mugs.

"Ioki and Blowfish left," he informed Dennis.

"Tom told me," Booker replied steadily nodding at Hanson who seemed to have calmed with the help of the alcohol. Doug realized with a jolt that made him momentarily choke on his Draft, that Booker had just had lust practically written upon his face while he watched Tom.

This was going to be a long night.

Soon they were all a little drunk. Doug was feeling happier and more calm, if a little less coordinated. Unfortunately Booker was now outright leering at Tom. Tom by now was the drunkest of the trio because he had needed it to calm his nerves, so he was oblivious to Booker's intentions.

"I'm going to get another drunk." Tom announced as he headed off in something that resembled a line to the bartender.

Doug wracked his intoxicated brain for a way to get Tom and himself out of there, as Booker spent his time shooting Tom covet looks. Seeing Booker's eyes widen almost imperceptibly and a devilish grin appear on his face, Doug turned to see what had caught his interest. Tom was leaning down to pick up a few dollars he had dropped as he unknowingly gave everyone facing his back a great of tight little ass. The leather skirt he was wearing was beyond tight and it had ridden up when he bent so that it barely reached passed his backside now.

Doug blushed as he turned his head back away only to see Booker lick his lips as he watched Tom. Blushing harder than ever Doug decided that his beer would be the safest place to look.

"The bartender forgut to charge me two dollars." Tom said brightly as he took his place next to Doug.

Yeah I bet I know why.

As Tom started to drink again Doug decided he had to get Tom out of here before Booker starts to hit on him outright.

"Tom can I talk to you for a moment. I have a problem I think you might be able to help me with," Booker said with a sly grin as he nodded to a room off to their side.

Too late.

"Sorry Booker, but I think I should ge- call a cab for me and Tom. We can't afford alcohol poising." Ok so maybe he wasn't at his most articulate when drunk.

Fortunately Tom had chosen that moment to yawn. "Yeah i's really late. See yuh later Book." Before he precariously stood up beside Doug and they made their way out. Doug glanced back to see Booker take gulp of beer and cast one last frustrated look after Tom.

Soon they were at Tom's apartment. This, of course, was mostly because Doug was drunk and feared Dorothy's wrath.

"Hey Doug!" Tom announced reappearing from his kitchen. "I got some more berrs- bu- beee… I got some drinks!"

"I think we've had enough beers," Doug replied feeling a little lightheaded himself. "Maybe I shlod lay down." With that he collapsed on the couch in a heap.

"Okey dokey." Tom dropped on the cushion beside Doug's head. While he was doing this, he didn't notice the blush that was once again forming on Doug's face.

Ok, Doug thought to himself, just don't think about Tom's ass and everything will be alright. He straightened up next to Tom.

"Is anything on TV?" He asked hoping for a distraction.

"It's busted." Tom replied.

"Any good music?"

"You hate my music."

"Oh yeah so -"

"Doug wha's wrong? You keep trying to get excuses to ignore me and-"

Oh god had he noticed? "Sorry Tom I hadn' nodecest I was-"

Tom forced him to turn around for a moment. "Wha's wrong Doug?"

Doug stared at Tom for a moment. He looked amazing. All dark hair and deep brown eyes with perfectly sculpted features. Then he found his own eyes fixed on Tom's small mouth. His larger bottom lip gave him the look of an eternal pout, and now all Doug could think of was how inviting those lips looked.

Before he was able to think Doug had captured his friend's mouth in a drunken kiss.

For a moment Tom didn't move, Doug's arms slowly circled his friend and pulled him closer to him. Tom relaxed and started to kiss back, and that was all it took to make Doug snap back into reality.

"Sorry," Doug panted. Staring in shock at Tom. "I don't know why I did that."

Tom touched his lips. The kiss had been warm and spontaneous, now he was left cold as Doug stared down at his hands abashed.

Spontaneous, now that was something Tom rarely chose to be. He was always trying to do the right thing. He complicated his life so much that he rarely got what he wanted. The only person now that was always able to bring out of his worst glooms and cared about Tom the most these days was Doug. The person he missed the most when he wasn't around was Doug. The person who set his skin on fire when they touched and could hypnotize him with a warm smile was, Doug.

It hadn't been until Doug left for Intelligence that Tom had realized that he was in love with his partner, but he'd thought Doug was straight anyways. Tom was sure he would only be a friend to Doug. That if he made a move on him their friendship would end.

The kiss had given him hope, but the end had torn at his heart like a knife.

Before he could allow himself to complicate this anymore he leaned over and kissed the larger man.

Doug was kissing back before he had fully comprehended what was happening. He allowed himself to really notice things this time. Like how soft Tom's lips were, how warm the inside of his mouth was, and how soft his hair was between Doug's fingers.

There was definitely something different about kissing Tom, he thought as they resurfaced for air. Tom blushed as Doug softly stroked the side of his face for a moment before they kissed again.

Tom was the only one of the two that was awake that night. He sighed softly as he watched Doug's peaceful face. He was amazing. The best friend Tom could ever want. The most loyal and steadfast partner he could ever need. Hopefully now he was something more as well. He hoped Doug wouldn't regret this in the morning.

He hadn't told Doug about his feelings. That could ruin whatever they have now.

"Some things are too complicated," he sighed as laid down facing away from Doug.

He never noticed the brown eyes watching him sadly.

-----

I want to know what you think, so please review