The Boss Finally Meets Their Match


The date was casual. He wore a blue t-shirt, and it hugged him like a vice. Except the way it looked on him was casual. He was also wearing navy blue denim jeans and blue and white tennis shoes, the soles all white. He had on his gold and purple Saints watch and silver Saints necklace. His skin became darker, but still light enough to pass as caramel and his hair was black and had the haircut of 'sarge.'

She had lopsided, auburn hair and her skin matched that of a tanned Caucasian female (natural not sprayed on). She wore a black tank top and black true-fit jeans with white trim. Then there were the golden hoop earrings and the silver Saints necklace to complete her attire. The red and black shoes didn't go unmissed either.

Purple eyes met blue eyes. Six feet met six feet. Everything was on the playing field, yet one player was taking way too long to make their move.

"So… you ordered this date, so where are we going?" he asked, slightly more interested in her than the date altogether.

"Well, you and I grew up in the same background, we like the same things, for the most part anyway, and you're asking me where I want to go?"

She pressed up against him and smiled. She knew she was teasing and he hated her for that. However, he knew if he could do something right today, she'd be his tomorrow. And the next day, and the next day…

"Stop thinking about fucking me and start thinking about where you're taking me," she commanded in that all-knowing manner. Usually he didn't take orders, but since he had the most lewd body in the world in front of him, it'd be best to learn how the mind of the body works. And how he can keep her happy. It never hurt any guy to keep a little arm candy on him every now and again.

He looked at her and told her wait for him for five minutes, then he ran off. She counted down, too, every single last second. Four minutes and forty-five seconds later he drove up next to her in a yellow Phoenix with chrome trim. The Phoenix decal on the sides and front, white word in black painting, helped make the car look cool, and the protruding motor completed the picture.

She got in and he drove to the one place he'd thought she'd enjoy as much as he would. They got to the airport and "rented" a plane. The police we're there just in time to chase the plane off the roadway.

"Well, at least you got excitement right, she said, looking out the co-pilot window as he went up. They were flying above the buildings in front of the park that was in front of a penthouse he scoped out earlier when he put the plane on auto-pilot. She followed him to the cabin and he opened the door.

"Here's the plan," he started, "it's a competition. Whoever lands in that pool and doesn't land somewhere else, going splat, gets to tell the other what they have to do for two hours."

"Deal," she answered and they jumped, diving for the pool. He didn't think she'd jump with him, so he knew she was too hasty to grab a parachute like he did. He spear-headedly dove for her as she descended towards the pool. Once within arm's reach, he grabbed her arm and deployed the parachute. They slowly glided and landed on the roof.

"Looks like I win," she said, brimming with confidence and not even bothering to hide her ego.

"Whatever," he said as he looked down into the penthouse.

"We'll start that bet of yours after ten," she said, trying to gain his attention and rub it in while doing so.

"Yeah, yeah, just shut up for a moment…"

He searched the interior of the penthouse, scoping out the place. He was so caught up in that that he didn't notice that her smile disappeared completely. Hell, he didn't even notice she was sneaking up on him. When she raised her fist, it was too late for him to do much of anything, at least, that's what the world thought. Apparently, the Male Boss was above that.

As she swung down he rolled out of the way and she shattered the glass fully, surprisingly not leaving a cut on her at all. He took a few steps back before turning to face her. They stood face to face, ten feet apart.

"You know," he started, seemingly oblivious to the rage that he just let loose in her, "it's cowardly to attack me when my back is turned. I thought you were the Boss, just like me, and we'd never stoop so low."

She grinned, the thrill of what was about to transpire was too great.

"I may be a Saint, but if you must know, even Saints sin. Now how about putting your money where your mouth is. If you beat me, we can fuck any and everywhere you want for a week."

At that proposal, he was taken aback for a moment before smiling. He could prove his supremacy out here and in private. He nodded, signifying he agreed.

"However, if I win," she continued, a devious smirk spread across her face and he felt a lot of negative energy coming off her, "You will be my personal assistant for the week, doing whatever I tell you to. If you can't get up in ten seconds you lose."

He grinned again, this time confidence and the odds were on his side. Sex with the most beautiful woman he knew, or a slave to her, both for a week in length. It was a no-brainer. He'd win, and he'd be set for a week, maybe more if she liked it. They walked up to each other, shook on it, then turned around and walked ten steps before facing each other again. The battle was beginning.

A calm settled over the roof as they stood there, grins wide, and completely confident that this match was in their favor. A gunshot was heard in the distance and, using it as the starting signal, they ran at each other.

He punched for her stomach and missed as she drop-kicked the hell out of his head. As he stumbled back she ran at him again, using this as her open opportunity. She slid under his open legs, punching him in the gut as she went, and rose up and flipped him by using his pants to throw him. He spun in the air twice before hitting the ground with a thud. She started counting but before she hit two he kicked up rubbing his jaw.

'He's a tough one...' she thought as she readied herself.

'Well then, she can fight and she's a beauty. Just where has she been all my life…' he commented to himself as he straightened himself.

She came at him again, throwing a flurry of punches and kicks, trying to get a hit in, but he simply blocked her punches or pushed her legs aside. One time he really pushed her leg back, roughly, and started throwing punches at her. She struggled to keep his power filled hits off her but finally landed one, right on her temple, after faking a hit to her gut. She was in the air for a moment as he started counting, brushing himself off.

At five she fully regained her footing, and decided to fully pursue kicking his ass. She threw hit after hit after hit and none of them collided. Eventually he sidestepped her and threw her over his shoulder. She hit the ground and he stood over her smiling. Big mistake on his part.

She smiled and he didn't know why until her foot hit him in his manhood, digging in balls-deep. He collapsed like a broken window and she had a smile as she counted all the way to ten.

He still laid there even after her and she laughed at him as he moaned and groaned in pain for a few more moments before finally being able to sit up on one knee.

He looked at her like he was pissed and in an odd sort of way he was. He was in too much pain to enjoy the sweet sound of her laughing. In a fit of rage, albeit playful rage, he ran into her, spearing her and carrying her to the edge of the roof before they both went over it and… landed in the pool.

When he regained his senses he felt his head lying in between two large and comfortable, plush pillows. He smiled to himself as he realized that they came with a built in heating upgrade. Thinking they fell off the building and died, he snuggled in closer before two hands brought his head away from his pillows and lips enveloped his. He opened his eyes and found her with her eyes closed, enjoying every second of their kiss.

They deepened it, tongues dancing in an aggressive battle of dominance over whose mouth would house them. Neither was winning and neither minded because they had all the time in the world. His hands traveled down to her now submerged boobs, groping them and eliciting moans from her mouth. She had a hand around his neck and another trailing his slick abs. Purple met blue again and neither spoke as words weren't needed for this.

As they dove in for yet another kiss they were interrupted as a barrage of bullets started sprinkling the water towards them. They instinctively grabbed the 45 Shepherd out of each other's hip holster and turned, firing like the ultimate badasses they were together, at the Morningstar that were now starting to overwhelm them.

Seeing this situation would get a lot worse before even trying to get better, they bolted from the pool and went to the helipad. The Male Boss grabbed a parachute lying on the ground and picked her up just as he jumped from the helipad. They fell for a moment before he deployed the parachute and as soon as they touched down they hijacked a Peacekeeper form a police officer. They were being followed through the park by Morningstar and cops.

As they got on the highway and headed back towards the safe house, an attack chopper descended right in front of them. They drove through as it fired all of its missiles at the pursuing criminals and officers. Leaving the chasers in piles of burning scrap metal, the helicopter flew towards the safe house with them.

They walked in and moments later Johnny followed.

"So, Johnny, how'd you know that was us?" we asked.

"If you ever see a police car getting followed by a gang AND cops, it's probably the handiwork of the Bosses. At least, ninety-nine times out of a hundred."

"Thanks," said the Bosses as Johnny left, most likely going out to fill his murdering quota for the day.

The Bosses looked at each other.

"We're getting that penthouse before the week ends, right?" he asked.

"Of course, how about Friday?" she asked.

"Perfect," he said before continuing, "and about what happened in the pool—"

"We never speak of it," she said in a serious tone which bought great confusion to his face.

"You're my assistant for the week. I hope you like performing free labor…" she said, installing a sense of the dread in the Male Boss.

As she walked away he watched he, noticing how her left leg was the longest and most dominant in her walk. When she opened the door to the bedroom she looked back, undoubtedly catching him checking her out. He stood in surprise as she spoke.

"Don't worry," she said before adding a devious yet seductive smile to her face, "Even assistants can be promoted."

She left him standing there with his hand behind his neck.

"Maybe this two Bosses thing isn't going to be all that bad…"


A/N: The story goes on. How was this chapter? And should I go into another mission or make another break in the story. I don't know what you'd like until you leave your review for me to carefully read. I lied about carefully, but I do read them.