A/N- Hey guys, this is my first Saints Row fanfiction and I wrote it mainly because I had this random idea for a pretty lengthy Matt Miller/Boss story set along the actual Saints Row games' story lines that I thought other people might like to read. Most of the other Matt/Boss stories on here are really short and I wanted to write one that would go on for a while and be sort of more fluffy instead of...all sexual? Because I want all you readers to imagine your own boss character in the story instead of just seeing mine, I will not be describing her at all (besides her height, which is sort of decided by the game anyway). The story line will follow along with the plot of the games mostly, but I will probably change the dialogue and tweak certain events to better fit the headcanon and not bore you guys. Enjoy! Reviews are better than an actual paycheck to me!

Disclaimer: I do not, nor will I ever own Saints Row or any of its characters. The content of this story was not meant to insult anyone in any way, shape or form. Rated T for violence and coarse language.

Chapter One: A Run of Bad Luck

The first time I saw her she was on my cellphone screen, glaring up at me through the camera feed in a way that made me feel like she could see me too. She had a gun in her hands, a heavy SMG that looked like it had been used way more often than it should have been, and an expression of absolute defiance on her face. They told me she was a psychopath and I believed them, but looking at her in that moment made me think there was more to her than the others knew.

I watch warily over Phillipe Loren's shoulder as the leader of the Saints fires one expertly targeted shot at the camera above her and I even cringe a bit when the monitoring device goes out with a bang. The screen of my cellphone goes all black then, leaving me to assume that the girl and her crew of miscreants must want the Morningstar penthouse for themselves. At least, that's the conclusion I'd drawn after watching the Saints boss wrest an answer about the bomb Loren had stashed in that hideout from an unwilling lieutenant.

"That cow!" my boss exclaims in his slightly annoying Belgian accent, "This is the second time in two days that she has escaped from me!"

"This would actually be the third time, sir," I begin hesitantly, but change tack at the speed of light when I see that Killbane is glowering at me, "A-although I suppose what truly matters now is how we take her down."

The DeWynter twins exchange a glance before putting their two cents in.

"She's the key." Viola says.

"The others will fall apart if we get rid of her." Kiki adds on.

Across the table from our little huddle, Killbane stops stretching his arms long enough to roll his eyes. I'll never admit it, but out of everyone in this room he is the person whom I fear the most. The wrestler before me is about six feet tall and more muscular than Damien, the leader of the third battalion of the Cyprian Order. Nyte Blayde references are the best references I have for this man.

"Killing her will be easy. Just get me alone in a room with her for two minutes."

Out of fear I don't comment on the stupidity of that plan, and I'm surprised when the DeWynters choose not to do so either. They're usually the voice of reason in situations like this. Loren shakes his head, though, and hands my cellphone back to me.

"This woman is a fighter, not a thinker. If we want to tear her down we will have to do it in a way she will not expect and cannot control."

I hold my phone gingerly in one hand, waiting for the rest of Loren's little speech. He might be my boss but I feel no qualms in admitting that he has a tendency to ramble on much longer than he needs to.

"What do you have in mind?" Kiki asks our leader. She and her sister are the heads of the biggest prostitute ring in the city, supplying everyone from common blue-collar laborers to wealthy politicians with expensive sexual favors. I repress a shiver at the thought because 1. I am a virgin (another thing I won't admit to freely) and 2. I always thought sex should amount to something more than pointless pleasure.

"I think we need to divide up our targets," Loren says, gracefully sitting back down in his chair at the head of the table. He swivels the seat around to face the colossal television monitor on the wall and gives me an order.

"Mr. Miller, please bring up any video footage you have collected on the Saints leader and her two remaining lieutenants."

I comply with his orders, using my phone to send out the requested data to the big screen. The monitor shows us four separate videos playing at once, three of them displaying the aforementioned gang members performing various activities and the fourth giving us a live feed of the Morningstar penthouse balcony, which has clearly just become property of the Saints. Two of the less important members of the gang are putting up decorative purple banners as we watch.

"This girl does not seem to be much of a problem," Loren gestures towards the pre-recorded video of Shaundi that I'd taken from her dating show, "I will leave her to you, Kiki and Viola. You are women, figure out how she thinks. Break her."

The twins nod, eyes fixated on the image of Shaundi coyly pulling her hand out of some Hispanic man's grasp. Phillipe then swivels around to address Killbane.

"Mr. Killbane, I am sending you after this...Pierce. He appears to be more of a tactician than a fighter and should be quite easy to get rid of."

Killbane is hardly paying attention to this, as focused as he is on massaging his biceps. If only I wasn't twig skinny in comparison, I'd tell him how useless he really is to us.

"It won't even be a challenge," the wrestler tries to make his voice menacing but it just comes out sounding like he has a sore throat.

"Does that mean you'll be taking on the boss yourself, sir?" I say, noticing that the Saints leader is the only target left. In her video footage, she is moving around the prison cell Loren had her thrown in when she'd tried to rob a Morningstar bank just a few days ago. She's got her fingers laced together behind her back and she's pacing the length of the room nervously. Shaundi and Johnny Gat (now assumed to be dead) watch her with expressions of annoyance on their faces. Even though there's a television screen between us I can tell that if she was standing right here beside me, she'd be quite a bit taller than my five feet seven inches. Not that it matters. At the age of sixteen, I've still got plenty of growing to do before I reach my full height.

Almost a minute passes like this before I realize that Loren never answered my question. I look over at my boss only to catch him smirking up at me in a self-satisfied sort of way.

"No, Mr. Miller," Loren says, "You are the one who is going to take her on. And you will win."
This revelation forces a wave of shock to reverberate down my spine, so strong that I can't think, let alone speak, for longer than I'm comfortable with. Viola, Kiki, and Killbane had burst in with their own complaints and suggestions as soon as Loren had announced this last piece of his plan, but he silences them with a wave of his hand.

"My word is final. Mr. Miller can fight this psychopath on a plane she has never felt at home on."

"What, you mean that technical shit he's into?" Viola interrupts scathingly, "This kid has no idea what he's up against!"

"Neither do you, Viola," Loren snaps, "I am not changing my mind. Now I need all of you to clear out of here and do what I hired you to do."

The twins grumble audibly and head towards the exit of the expansive room without another word to either Loren or me. Killbane files out not long after them and it seems like he's already forgotten about his desire to bring down the Saints all on his lonesome. When I turn back to our boss, hoping to talk my way out of carrying out the mission he's assigned me, I'm a little surprised to see him still fixated on the live-feed of the ex-Morningstar penthouse. Something about his expression makes me rethink any ideas I'd had of rejecting his assignment, and encourages me to follow my fellow officers out of the room.

I walk down the hallway as quickly as I can, my shoes making a slapping sound each time they come down against the tile floor. I don't want to kill her. I hate her, obviously, I mean what's not to hate about the woman who could potentially take the lives of more Deckers than I'd care to lose? I hate her, I really do, but I don't want to kill her. I keep imagining her the way she'd looked when she'd shot down the camera I'd been watching her on with self-confidence and anger too obvious in her bright eyes. She's a psychopath and it is my job to hate her-to kill her, but (and my heart gives a weak flutter as I think this) she'd somehow seemed quite lovely to me in that moment.