Disclaimer: I do not own Marvel or any of its characters and lines from the movie used in this story. What is written here is for entertainment purposes only. I do not make any profits from it.
1st
The interrogation room wasn't exactly what one would call daunting. It was, after all, just a room with a table and two chairs facing opposite each other... Except the table had handcuffs attached to it making Pepper consciously fold her arms and there was a two-way mirror which made her very paranoid about who was watching her on the other side.
She closed her eyes and, not for the first time, began to think about whether this even fell in her job description.
Just when she was mentally drafting a new clause in her contract, the door opened and her boss was ushered inside by an officer.
"Mr. Stark!" Pepper exclaimed jumping to her feet. Her boss was wearing overalls, probably the only thing the jail had available for him to wear. She could already hear the unsavory words he had to say to the unfortunate employee that gave it to him.
"Potts! Did you bring it?"
"Yes. I—" Pepper sighed. "Mr. Stark, you really should refrain from streaking into a public fountain naked—"
"But it was a moment made for nudity—"
"—no matter how beautiful the girl you're with is—"
"But people want to see me naked!"
Pepper raised a brow.
"Ok," Mr. Stark relented. "The girls wanted to see me naked. And a select men." He suddenly eyed Pepper. "Do you want to see me naked?"
Pepper frowned. "That's inappropriate. And so is your behavior. I'm gonna have to do a lot of damage contro—"
"Potts, the clothes, please," said Mr. Stark, impatiently. "I'm naked and commando underneath this hideous thing and you want to talk PR? Do you see this?" He pointed at the slippers he was wearing. "They've got me on slippers that don't even match!"
The mismatched slippers only added to Pepper's headache.
She forced herself not to say the words 'I quit' or to retort that he shouldn't have taken his clothes off in the first place and started an orgy in a public fountain of all places.
She handed him a garment bag which had his clothes inside, and a bag with his underwear, socks, and shoes.
"I'll wait outside while you change, sir."
"You sure you don't want to assist me?" He wiggled his eyebrows suggestively.
She glanced back at him, the door halfway open. "You're a big boy, Mr. Stark. You managed to get out of your clothes without me. I think you will do just fine getting yourself in them."
"Party pooper." Mr. Stark waved her off and started unbuttoning the overalls.
It was only when Pepper stepped out of the room that she realized there was a two-way mirror in there, anyway.
She sighed. She doubted Tony forgot that too. The man loved to put on a show. It's what got him in jail in the first place.
2nd
Mr. Stark looked awful. His rather expensive clothes were dirty; specks of grime laced the front of his shirt, and his eyes were bloodshot red indicating just how bad of a day he'd had.
Pepper bristled with annoyance. He shouldn't have the nerve to look this pitiful and exhausted not when he woke her up in the middle of the night to bail him of out jail.
"Potts!" He groaned, standing up to clutch the bars of his cell that separated him from her.
"Mr. Stark, you—" Pepper took a step back, her nose wrinkling. "You smell like urine."
He gave her a deadpan look and said by way of an explanation, "I'm in jail."
"I can see that... And smell that." She sighed. "Mr. Stark, they told me you threw a bottle at a police officer."
"Accosted a police officer," he corrected, slightly swaying on his feet. "He called me 'son.'"
"And they said you called him 'Howard.'" Pepper exhaled. It was the anniversary of his parents' death. It explained his inebriated state and violent reaction, but that didn't justify them.
She had half a mind to leave him here and come back in the morning, but she knew that today of all days wasn't the right time to teach him a lesson.
"Mr. Stark, the force is not pressing charges considering who you are but please, stop this. You don't have to do this alone."
He barely heard her. "Just get me outta here."
3rd
"Personal assistant? More like his personal whore."
Mr. Stark's whole body tensed and Pepper immediately put a firm hand on his arm.
"Ignore him,"
He didn't.
Without any warning, Mr. Stark turned and hit the man right on his face.
The bystanders shouted and gasped in surprise.
Pepper shrieked. "Mr. Stark!"
She pulled her boss by his blazer but he continued to do a number on the guy's face.
"Stop it!" A stranger pulled Pepper back, preventing her from joining in the fray and getting hurt. "Tony!"
It takes two officers to pry Mr. Stark off the man who ended up with a broken nose.
An hour later, they are in the precinct and filling up an incident report.
"He's pressing charges," Pepper told her boss who was without a hint of regret on his face.
"Hmm," he said with a shrug. "I guess I deserve that. I did break his nose."
"Yes. And you broke your fingers as a result." She pointed at his bandaged hand.
"Thank God they're insured then, right? I guess Obie's idea to insure all of me wasn't such a bad one. Maybe I should insure you too. You're important to me." He said the latter quietly that Pepper almost missed it.
She didn't know what to say to that, so she said, "Mr. Stark, you can't just hit anybody that says something you don't like."
Mr. Stark's eyes almost popped out of their sockets as he sputtered, "Don't like? Says something I don't—He insulted you! He called you a you-know-what!"
Pepper shook her head. It never failed to amaze her that her seemingly unfeeling and callous boss, who didn't care one bit about the nasty things people said about him—Merchant of Death, Iron Monger—actually gave a shit about the nasty things people said to those he considered family.
"Mr. Stark, you don't get it. You only make it worse when you respond to their taunts. When people call me your girlfriend or insinuate that I'm sleeping with you—let me finish—when they demean me and you come to my defense like that, you're not helping. You validate everything that they're saying because that's exactly how a boyfriend or a lover would react."
Mr. Stark's face scrunched up in confusion. "That doesn't make se— What would you have me do? Ignore it? Let them walk all over you?"
"Yes! No! I… You issue a statement or… fight them on our terms. Don't stoop down to their level because then they win."
Mr. Stark folded his arms and grumbled something incoherent.
Pepper shook her head endearingly at the sight and patted his leg. "You finish up writing that statement while I go and settle bail."
4th
"You what?" Pepper put a hand up to stop an intern from talking because she was pretty sure she heard her boyfriend just say that he's in jail. Again.
"Drove 80—"
Pepper waved the intern out of her office and focused her attention on the man on the phone. "No, no. I think what you meant to say was that you went beyond the speed limit and when an officer of the law asked you to pull over, you decided it'd be fun to see if he could catch you."
"You said that, not me."
"You resisted arrest!" She hissed each word over the phone.
"Semantics."
Pepper groaned.
"Pep, you're not gonna leave me here are you? The last time you took so long to come get me, I had to burn the clothes that smelled like pee. D'you remember that?"
She did. She remembered it vividly.
"I particularly remember that I was the one doing the burning and you were nursing a hangover in the bathroom."
"Pepper, please!"
The fact that he actually said the word made Pepper concede. If she did ask Happy to take his time driving by using a longer route, Tony would never know.
5th
Tony knew he shouldn't have taken the kid from daycare and just went to the damn board meeting like Pepper told him to.
Because now his kid was bawling his eyes out, asking for Pepper (and there's no way Tony was going to call his own demise, thank you very much), and making a scene in a mall.
"Sir, is something wrong?"
Tony stared at the mall cop, looked around, and then pointed at himself. "Me?"
The guard nodded.
It wasn't often Tony got called 'Sir' then again, it also wasn't often that Tony completely shaved his goatee and went to a mall.
Was he that unrecognizable without the goatee? Or outside the Iron Man suit?
"Sir?"
"What? Oh, yeah. My kid's throwing a tantrum." Tony crouched down to the toddler and tried to lift him off from the ground. "Come on, kiddo. Time to go."
"Mommy!" wailed the two-year-old, an endless stream of tears coming out of his eyes as he refused to be lifted up by Tony.
"Maybe you should call his mother," suggested the cop.
Tony shook his head. "No can do. If I call her, she'll know where I am, she'll know what I did, and she'll kill me.
The security guard warily eyed the kid and then Tony. "Sir, you do know that taking the child without the mother's knowledge or consent is kidnapping."
"What? Kidnapping? But this is my son and I—what are you doing? Don't touch him."
The guard ignored Tony and crouched down to the boy's level.
"Are you okay?"
The boy shook his head and then pointed at Tony. "Don't like! Don't like daddy! Mommy only!"
The guard gravely looked up at Tony and Tony knew what was gonna happen next before it even did.
"Sir, I'm gonna have to ask you to come with me."
..
"Is there something I can help you with, ma'am?"
Pepper smiled kindly at the officer, ignoring the migraine coming on. It wasn't his fault she married an idiot. "Yes. My name is Virginia Potts. I was told you brought in two children?"
The officer nodded recognizing her name as the person they contacted. "No, ma'am. Just one child and a man who claims is his father. He also claims to be Tony Stark but that's neither here nor there."
"Yes. Like I said, two children."
Before Pepper could continue, there was a rattling sound and she turned to the right to see her husband behind bars (again) and shouting, "Pep, honey, tell these men I really am Tony Stark and that really is our baby and I'm not really a kidnapper."
Pepper turned away from him to find her son being escorted to her by another officer.
She beamed at him and took him in her arms. "Hi, baby! Oh, I miss you!"
"Mommy!" The child latched himself on to Pepper, immediately settling his head on the crook of her neck.
Pepper patted his back. "Daddy took you on an adventure again, huh?" She turned to the officer in charge and said, "So... That man is my husband and he really is Tony Stark. He's also not a kidnapper."
The officer's eyes widened at that. "We apologize, ma'am. It's just that he was—"
"Oh, don't worry about it. He's not dangerous but he does have a habit of getting himself into a lot of trouble. So, thank you for stashing him in here, taking care of my son, and calling me right away."
Pepper flashed him her best smile and the officer blushed. "Only doing our job, ma'am."
"If it's not too much trouble…" Pepper motioned at the man to lean in closer and she whispered something in his ear.
The officer chuckled as he pulled back. "That can easily be arranged."
"Thank you so much."
Pepper walked over to the jail cell and finally faced her husband.
"So, d'you clear everything up?" Tony asked, dying to get out of there.
"You don't know how long I've wanted to leave you in here."
"What?"
"Yeah. I mean, after the third time I've had to bail you out, I thought, why not let him stay there for just one day?"
Tony gaped. "I can't believe I married a snake."
"Stop being so dramatic."
"You betray me."
"Don't worry. You'll have a lot to do in here so you won't get bored."
As if on cue, an officer started setting up a laptop over a foldable table placed right in front of the cell.
"What is this?" asked Tony, eyeing the laptop suspiciously.
"You're going to go to that board meeting. Via skype."
Tony groaned. "Pepper!"
"Have fun!"
"But Pepper, there's no bed in here!"
"Come on, baby. Say 'bye bye' to daddy."
"Bye daddy!"
A/N: Tony has definitely been arrested loads of times.