Between the Shadows.

Sam's eyes widened at Negan's answer. She knew it was foolish to think that it was surprising after everything she had begun to suspect about Negan but still, she was surprised. To think that anyone was rich enough to own an entire garage full of antique cars, Sam thought it was almost too good to be true. It only further cemented that she had to ensure she made Negan happy tonight, in the back of her mind. If he was that well off with money, he was powerful and she didn't want to know what would happen should she upset him in any fashion. It didn't matter how he came across the money because in this city, money talked and Negan was far richer than she ever would be.

Quiet as they drove along, Sam's reaction was much the same as Negan pulled into the underground garage. She twisted and turned however she could to get a better look at the cars, spotting ones that she had never even heard of, more often than not. She saw classics but still, she wondered what it would be like to own one. To ride around in a vehicle that turned heads, wherever you went.

Sam seemed to suspect that she should stay in place, in the passenger seat, until Negan came around to help her out. She offered him a brilliant smile as she stepped out, readjusting her dress with her free hand. "Thank you, sir," she answered, giving a nod at the mention of an elevator. When Negan's hand traveled further south, Sam wasn't the least bit surprised. She tensed just slightly when he squeezed on pure instinct, before she let out a small moan. It was all about pleasing who she was with and making them think she wanted it - that they were bigger and better than anyone else she had been with. Inflate their egos, keep them happy, and you would be satisfied with the end result.

"Dessert's in the penthouse?" Sam teased softly, hoping that she wasn't over stepping the boundaries that Negan had set out so clearly before. She wasn't to talk dirty unless they were in his home but she thought her words were safe enough that they wouldn't cause any harm.

Negan couldn't help but let out a bellowing laugh, purely amused at Sam's teases. It seemed she was beginning to grow more comfortable around him as the night went on, unlike when they first sat down to dinner and she seemed so stiff and scared. "If you want dessert, you'll get dessert." He called the elevator and walked her inside, beginning the ascent up to his home.

"This whole restaurant and hotel are mine, impressing huh?" Negan was very narcissistic, he liked to talk about all the things he had accomplished and all the nice things he owned. Of course, it was a real restaurant and a real hotel, even if none of his attention went into it. It brought in about 1/4th of his money, so it wasn't a huge venture to him, he let someone else take care of all of the business pertaining to it, and he claimed all the reward. It was a very prestigious establishment.

The elevator opened up, revealing the first floor of his penthouse, the living area. All sides of the room were just windows, with a beautiful view of the skyline from all angles. To the left was an elegant kitchen with a bottle of bourbon the only thing decorating the counter top and set out right in front of them was a living seat with a large flat screen TV. Behind it was an enormous aquarium with two sharks swimming around each other.

"Let's get you comfortable, eh?" Negan turned to Sam, pulling her jacket off of her shoulders, hanging it up on the coat rack next to the elevator. "Would you like something to drink?" He asked, heading over into the kitchen and grabbing a glass to pour some ice into.

Sam's entire body visibly relaxed when Negan laughed instead of chastising her. She smiled a bit, resting her hand on Negan's shoulders as they stepped into the elevator. If Sam had thought she was shocked by Negan's obvious wealth before, his cars didn't even have a chance of comparing to her awe as they stepped into his apartment. Her eyes were as wide as saucers, showing just how unused to this sort of lifestyle she was. If she had been thinking about it, she would have stayed more collected but she was too shocked to do anything else. At least until Negan started to speak, pulling her right back to the present.

Lifting her arms so that it was easier for Negan to pull her jacket free, she thanked him quietly. Sam hesitated, looking down to her feet. Did she leaves her heels on or take them off? At home she would have taken them off immediately but she didn't know if Negan would prefer the look or not. Sam swallowed back the nerves, looking up when Sam spoke.

She started toward Negan, lingering by the island in the kitchen. Not wanting to crowd him, Sam cleared her throat before beginning to speak. "Just a water would be great," she said, grinning a bit as she watched Negan move. Sam was feeling a bit thirsty, to the point where she wanted something other than alcohol. She hoped Negan wouldn't mind too much.

"I.. uh," Sam paused, realizing her voice wasn't strong enough for her to actually speak without sounding like a fool. Her cheeks had tinted a deep red and she was hopeful that her makeup did a good enough job that maybe Negan wouldn't have noticed it. "Do you want me to take off my shoes so I don't track dirt anywhere or..?" Sam left the question open ended, figuring Negan wouldn't be shy about telling her what he wanted from her in any regard.

Negan pouring himself from bourbon. He had wanted to get some more alcohol in her to make her loosen up some more, but if water was what she wanted, that's what she'd get. He was a gentleman after all. "Yes, get comfortable, take off your shoes." He smiled and walked back to her, both glasses in hand. He gestured her over to the leather couch, and sat her drink down on the table. He took a large swig from his glass, letting his eyes sweep over her. She was gorgeous. He watched her take her shoes off and he relaxed back, draping an arm over the back of the couch.

"Let your hair down too, while you're at it. No need to be trying to impress anyone anymore." His smirk only grew. It was nice seeing her all dressed up at first, from her nice dress to her hair all done up, but now he wanted to start to get down to business. He wanted to know what kind of girl she really was and by the looks of all her tattoos, a classy lady always with her hair up and in nice gowns she was not. He knew that.

He leaned over to her and placed a hand on the back of her head, beginning to pull apart her updo, picking at the bobby pins that kept it in place. As each one came out, her nice blonde hair came down in loose waves. "That's a good look." He smiled, placing some kisses on her neck.

Sam had been so relaxed with Negan that she was a bit off her game. It was like she didn't quite know how she was supposed to act, even as sat on the couch in Negan's living room. His words were all it took for her to tart to reach up toward her hair to let it down completely, instead of the half updo she currently had. But when his hands found their way to her hair, Sam's arms dropped to her lap and she stilled, her breathe caught in the back of her throat.

His hands sent goosebumps racing across her flesh, something she wasn't so used to. When the last bobby pin came out of her hair, Sam gave a shake of her head to let her hair tumble the rest of the way out of the bun. She bit down on the inside of her lip, tilting her head to the side when she felt Negan's lips against her skin. She was thankful that it was getting to this point because as nervous as she was, she could resort back to her experience. Negan was a man and men wanted one thing only when they came to her.

Sam pushed away her worries, moving to sit up a bit straighter. "Sir," she whined quietly, twisting so that she could lift a leg over Negan's lap. In the back of her mind, she hoped that she wasn't taking things too fast for Negan but she thought if she showed interest, it would be better in the long run. "Let me show you an even better look," Sam purred, reaching behind her back to tug down her zipper.

Negan sat back and let out a seductive pur as he watched her reach around to undo her zipper. He grabbed his glass and chugged the rest of the bourbon, beginning to feel all warm inside from the liquor and his head spin a little. He slid his jacket off and fumbled with his belt buckle, ready to get down to business.

Her sleeve straps fell down her shoulders as she unzipped her dress and she began to shimmy out of it. Negan licked his bottom lip as her body began to become exposed for him. He helped slip it down the rest of the way, letting his hand run up her side, cupping her breast as he tore off her bra.

"You are a god damn beaut, baby." He smirked as leaned over her, grabbing her breast and smashing his mouth down on hers.

When Negan didn't react to her advances, Sam took that as a good sign. She stood just long enough to push her dress down her legs, letting it pool at her feet before she straddled Negan again. Letting out a quiet giggle as he undid her bra, Sam grinned into the kiss as she deepened it.

She only pulled away when she was breathless, trailing kisses down Negan's jaw, to his collarbone where she nipped lightly. Nothing to cause any pain, just enough to excite him. "Should we move to the bedroom?" Sam whispered again his skin as she started to unbutton his shirt, figuring he may want to head to his bedroom but she knew that anywhere in the penthouse was fair game.

Negan licked his bottom lip and quickly rose up off the couch, keeping Sam up, her legs wrapped around his waist. "You're full of great ideas." He teased, he kissing over her collarbones and biting down on her neck as he took her back to the elevator and went up to the top floor.

His bedroom was dark, a large California King bed sat in the middle of the room, covered in black silk sheets with a black silk canopy hanging around the edges to conceal what would go on inside.

The walls were dark Mahogany, the windows tinted black to keep the privacy in the room, though still the view did illuminate it somewhat, giving a nice romantic ambiance to the room.

Negan dropped her to the bed and began to peel away the rest of his clothes, his shirt, his jeans and then lastly his boxers. He crawled over her, trailing kisses all the way up as he stroked his cock, making sure it was hard and ready for her. He rubbed his tip between her legs, feeling how wet she was.

He knew she probably thought tonight would only be about his satisfaction, but she didn't know Negan was a real woman pleaser. He was ready to eat her up.

Sam didn't even have the time to take in Negan's bedroom, her attention focused solely on him. Her eyes had slipped shut when Negan pushed her back against the wall of the elevator and they stayed that way. She never did like focusing on who she was with. She wanted to go through the motions and get done with it so she could leave. If she didn't, she would start to wonder what it felt like to have a boyfriend. What it felt like to have someone you could call home instead of an empty apartment. Someone you could share the little moments with. Someone you could lounge around with and just watch stupid movies all day with.

Giving a shake of her head to clear her head, Sam grin as she watched Negan start to undress. She shimmied out of her underwear, dropping them off of the edge of the bed. Her eyes locked onto Negan's as he climbed onto the bed, spreading her legs for him to settle between.

Sam let out a groan as she felt him, dropping her head back against the pillow beneath her head. SHe gave a roll of her hips, pressing closer to him. "I need you," she whined, wrapping an arm around her shoulders, dragging her nails over his skin. "Please," she whimpered, wetting her lips with her tongue. Sam arched her back, pressing her chest to his. "Fuck me."

Negan frowned, for just a split second feeling like this was rehearsed, like these were just motions Sam went through with every man. He shook his head clear, a smirk replacing the frown on his face. It didn't matter, if he was good enough, like he thought he was, he'd get a real reaction out of her yet.

He pushed himself into her, hard, nothing about Negan was gentle. He placed his thumb over her clit, going around it in circles and tugging on it as he fucked her. His other hand found his way into her hair, wrapping it around his fist as he pounded into her. He could feel her cunt tightening around his dick, making it hard to pull out and push back in, but he liked that. That let him know he was doing his job right. He bent his down and flicked over her nipple with his tongue, taking it between his teeth and nibbling on it.

"Feel good?" He groaned, slamming in to her harder with every thrust.

Sam hadn't been ready for the way that Negan slammed into her. In hindsight, she should have been ready because Negan was a bit rough around the edges. She bit down on her bottom lip, her body relaxing beneath him with each circle his thumb made. "Fuck," she whimpered, her fingers digging into his shoulders. She let out a whimper, her eyes becoming lidded.

Sometimes it felt like a job and rarely did it ever feel good. This? It felt amazing. Her brows pulled together as she dropped back against the mattress, moving to wrap her legs around his waist to pull Negan in.

"Uhhuh," was all that Sam could get out before she let out a moan, her body beginning to tense as a knot formed in the pit of her stomach. "O-Oh my G-Go-d," Sam gasped, her eyes clamping shut as she rolled her hips against him. Sam started to moan, only for it to be cut off as she started to cum, her pussy tightening around him. She moved against, her nails digging into his shoulders.

Negan moaned out, her cunt tightening up around his dick so much it felt like it was clamping down almost. "Cum for me, sweetheart." Negan smirked, continuing to move in and out and run her clit with his thumb. He held her up by the arch of her back, focusing on her clit until she relaxed back into the bed. Negan could tell that she was completely drained and done.

He moved in and out for a few more moments, enjoying how relaxed she felt, sliding his hands down her hips and grabbing her hard. "Fuck..." He moaned, looking down at her body as he pulled out and jerked off onto her stomach, getting it all over her. He groaned as came, almost sounding like a ferocious animal as he finished.

"Fuck!" He smiled, falling down next to her, feeling complete release.

Sam let out a soft moan as Negan came, having had a moment to catch her breathe so she was able to focus more on Negan than she thought she had been. She panted as she moved to sit up slowly, her cheeks flushing as she felt his cum start to drip down her body.

Clearing her throat, Sam refused to look in Negan's direction. It was better that way. It was better to just get on with her night so that she didn't start thinking about what she wished she could have.

"I should wash up and uh, get on my way..." Sam trailed off, completely unaware that she should be expecting to spend the night at Negan's.

Negans smile immediately fell from his face and he sat up quicker than she had. "Get on your way? Excuse me?" He got up off the bed, a little offended but trying not to be. He knew how other "clients" must treat her. He was different and he knew that. "No, no, no." He shook his head and helped her off the bed, bringing her to his bathroom to grab a wash cloth to wipe her off. "You're staying the night, sweet cheeks."

Sam jolted, fear flowing through her as she looked up from the mattress as Negan spoke. His words worries her, the way he spoke sent fear flowing through her body. She had angered him and he would lash out at her. By the time that she left, Sam would be sporting a few new bruises and by the time her bosses found out, she'd regret just about everything she had done over the last year.

Afraid to even speak, Sam took a few, hesitant steps to follow after Negan. When he helped wipe her off, she thanked him in a small voice while staring down at her feet. Sam kept herself as calm as she could, biting down on the inside of her lip. "I-I'm sorry. I didn't realize," she whispered. "I just... I wasn't told an-" Sam cut herself off, realizing she probably just sounded like she was making excuses at this point. She cleared her throat, wrapping her arms around herself as she started to follow him back into the bedroom. "It won't happen again."

Negan frowned and looked up at her as he led her back to the bedroom. "Are you okay? You don't have to be afraid of me." He caresses her cheek and pulled her close to him as they sat back on the bed. He got it, most of her other clients would hit or abuse her if she didn't do exactly what they wanted without having to tell her. "I'm not gonna hurt ya, Sam." Negan brushed her hair back away from her face and kissed her cheek.

"I just thought it'd be nice for you to stay the night. I like the company." He smiled, trying to brighten the mood. "Let me get you a drink. That always helps me loosen up." He got up and opted to take the stairs down to his first floor.

Sam shook her head to clear her thoughts as best as she could, looking up to meet Negan's gaze when he said that she didn't have to be afraid. She still was but she would do her best to act as if nothing was wrong, that nothing was bothering her.

When Negan returned with a mixed drink for her, Sam offered a weak smile and took a sip of it. "Thank you," she spoke softly, sitting propped against the pillows on the bed. "I honestly just didn't know you liked for us to spend the night otherwise it never would have been an issue and now I just feel silly," she attempted to explain, hoping that they could just leave it at that. Sam had never and hoped to never have to admit it to someone, about how she was afraid to have any sort of intimate relationship outside of sex.

"Yeah, I imagine it's uncommon with all the other men..." Negan sat down next to her on the bed, hoping his choice of words didn't offend her. "But I like you, so there aren't going to be any other men." Negan looked into her eyes so she knew he meant business. "Your company knows how I am, so it won't be an issue. They expect it from me. I only ever have one girl at a time, and while she's mine, she's only mine." He took another sip of his bourbon.

He knew his words probably scared a little, especially with how he delivered them. "And I know you're probably worried you'll lose out on money, less men, less money, smaller cut for you... but I get that, and you don't have to worry about it." He whispered and pulled out an envelope from his bed side table that was filled with cash. He slid it over to her and smirked.

Sam looked up to Negan, her confusion growing more prominent on her features as he said there would be no other men. Her body grew tense and she opened her mouth to argue, afraid that it would mean nothing more than her losing out on work. Her confusion only seemed to escalate as Negan pulled out an envelope full of cash and handed it to her. She picked it up, peaking inside of it before she looked up to Negan with wide eyes.

"I... this doesn't..." Sam trailed off, completely confused about what she was supposed to say to this. She knew that she didn't really have a choice in the matter but she was beginning to realize that she was going to be confronted with the one thing that she didn't want. Negan had treated her like a perfect gentleman tonight, like she would want from an actual relationship. So being around him on what seemed to be a more permanent basis?

Sam shook her head, clearing her throat before she looked down to her lap, suddenly feeling shy. "Um, I guess.. how often will you.. want my company?"

Negan leaned back on his pillows and continued to sip from his glass of bourbon. "Every few days, maybe nightly..." Negan shrugged. In all honest, Negan liked to have one girl to himself because he got lonely. Frequently. He didn't like to get attached to a girl, call her up and find out she was escorting someone else that night, that's why he started paying more to reserve one girl for himself.

"That's why I also pay you, without your companies knowledge. I know missing out some nights work cuts your pay drastically, so don't worry- I'll take care of you as long as your servicing me." He crossed his legs over each other and relaxed. He had only had this conversation a hand full of times, he tended to keep one girl for months on end. But the awkward confusion of it never got old, he never got used to it either.