Between the Shadows.

Sam felt like she was going to be sick as a chill ran up her spine, as she listened to Negan further explain himself. If she had to be with Negan even every other night, she was bound to grow attached to him. But she knew better than to say a single thing. If she could just keep her emotions in check and do her job, there wouldn't be a problem. Or so she hoped.

Giving a quick nod of her head, Sam draped one of her arms over her torso as she rolled onto her side to face Negan. "I appreciate that more than you'll probably ever know," she commented quietly, offering a nervous smile. Sam didn't want to admit that the idea that this might be okay, so long as she was able to keep herself together. "Can I ask? Why me?"

"Do you want me to be truthful?" Negan asked her. "I've had quite a few nights trying to find another girl I liked, but they all came off to slutty to quickly. Like sitting down to dinner and immediately talking about what they wanted to do with me. None of them had class or personality, they were solely riding on their sex appeal. I have no interest in that." He shrugged.

"You had class about you, you waited till we got back here to start being naughty." He smirked, running his hand up her thigh and smacking it lightly. "And you have ambitions beyond just being an escort girl for the rest of your life. I like that. I want to help."

Sam's face morphed, a frown overtaking her features as Negan explained why he thought she was a suitable choice. Surely she wasn't the first one that Negan told what he expected and yet she was the first one to listen to what he said he wanted? She couldn't understand how that had even happened. Blinking seemed to be the only thing she could remember how to do, her shock only continuing to blossom the more Negan spoke.

As easy as it would have been to nod her head and agree, Sam didn't feel like that was the right answer. She almost felt as though it was a sort of test. "You don't have to do that," she commented, propping her head up on the palm of her hand. "You're already paying me more than you should be, anything more is just... outlandish," she said, her face scrunching a bit. SHe hoped it wouldn't offend him but she also didn't want Negan thinking that she was just going to take advantage of his generosity.

Negan couldn't help but chuckle at Sams attempt to sway him from giving her handouts. That was another thing he had already picked up on, even in this line of work she was hardworking and liked to earn what was given to her.

"Sam, no amount of money is outlandish, when you're in my shoes anyway. I basically run this city from behind the curtains. You've had it hard enough, let me help you." While it was easy for Negan to pick up on Sams traits and learn the way she worked, he knew he may come off a bit more complex. Sam didn't know a thing about him or about his business or about his criminally gained power. If she played her cards right, she would soon though.

Sam frowned slightly when Negan pressed further in an attempt to help her. She couldn't understand why he wanted to help her, she was just another whore and while he seemed to like her, what would happen when he tired of her? From what little she knew about Negan, she assumed that he could have just about any woman in the city that he wanted. He would find someone new in due time.

Clearing her throat, Sam started to worry at her bottom lip. "Is there anything else I should know about your preferences?" She asked after a moment, figuring that it was probably best to try and remember them from the beginning. She had no clue how this was going to last but she would put her best foot forward, whenever she could with him. Who was to stay that they both couldn't get something out of it?

Preferences. Negan smiled and shut his eyes, allowing his head to rest back against his downy pillow. "If I take you out in public, act like a classy lady. Don't speak of what we do here in my room." He breathed out, bringing his hands to lie beneath his head. "But when it comes to what we do in here, I never like to do the same thing over and over. I like to explore." He purred, opening his eyes and turning on his side. "I want to explore every part of you. Just be open to me." He trailed his hand down her side and squeezed her hip.

"That's not to say if you're ever uncomfortable that you should go handle it." He got a bit more serious. "If there's ever anything you don't like you tell me. Immediately."

Sam couldn't help the laugh that bubbled up inside of her chest. She started to shake her head, shrugging her shoulders slightly. "There's nothing you could ask of me, that I haven't done before." She didn't mean to make Negan feel bad or uncomfortable or an stretch of the imagination. She simply didn't want him to think that she would ever tell him no to something. She had been in this line of work for long enough that she was sure that she had done just about everything.

Inching closer to Negan, Sam set her hand on his chest. She didn't know if he would want another round tonight but she suspected and she wasn't about to let him down. "You ready for round two, mister?" She teased as her hand trailed down his torso, giving him a smirk.

Negan snatched her hand from his chest, holding it tightly, but not enough to hurt her. "I didn't say anything you hadn't done before, I said anything you don't like, baby girl." He didn't say it mean or harshly, he just wanted her to know. "If something hurts or you don't want it, you just tell me."

It was hard for Negan to admit it, and he never would, but sex wasn't the first thing he wanted from any girls he paid for. Companionship was the first. He got lonely in his line of business, really lonely.

"But with you, I'm always ready." He purred, bringing her hand to his lips to kiss.

Sam startled at Negan grabbing her but she said nothing, figuring that there was no point in arguing with him. She had no intention of letting him know if either of those things happened but if he thought she would, what was the harm in that? She gave a small nod of her head, offering a timid sort of smile.

Focusing on what she knew how to do best, Sam let out a small giggle as she leaned up, nipping at Negan's jawline. "Good," she whispered, giving his shoulder a light push. Once he had settled back against the bed properly, Sam sat up, turning to straddle him.

"Let me take care of you," she murmured, leaning down to capture Negan's lips in a harsh kiss, cupping his cheek. Her hands roamed his chest as she gave a roll of her hips. "If I may?"

Negan felt his boxers get a little tighter as his dick rose up, excited at the thought of this beautiful creature riding him. "Mmm, you may." Negan purred, raising his hands up to her chest and cupping them both, running his thumb of her nipple, flicking over it. "God, you're so god damn gorgeous. What're you gonna do to me?" He breathed out, winking up at her.

He let one hand fall down to his dick, pulling out from under his boxers and rubbing it against her thigh. It wasn't a lie when Negan thought about just how gorgeous Sam was, way prettier than any other girl he had seen come to escort him.

Sam didn't quite realize it yet but the idea of being with Negan, of being with someone who also cared about her pleasure was enough to send her thoughts spiraling out of control. Just the thought was enough to turn her on. Rolling against Negan's hips, Sam moaned as she leaned into his touch.

"Negan, please. I need you," Sam whined softly, lifting up just enough as she reached between her thighs. Wrapping her fingers loosely around Negan's cock, she gave him a few, short pumps before lowering herself back down on him. Sam let out a breathless moan, tossing her head back as she settled into a fast pace, focusing a bit more on her own pleasure than she normally would have.

Negan groaned once she slid down onto his cock and he arched his back up a little in surprise. "Fuck-" He gasped as Sam immediately went into a fast pace, not even taking a moment to stop. "You're so fucking tight." Negan groaned, grabbing her hips in his hands as she rode him. He relaxed his back against the bed and just watched the view, his eyes watching her tits bounce as she fucked him. He could tell by the way she rolled her hips against him each time she came down that she was trying to get herself off too and that only made Negan's dick throb harder.

"C'mon, are you gonna cum for me, Sammy?" He chuckled, biting his lower lip as he felt Sam's cunt tighten even more around his dick. "I wanna feel you fucking get off on my dick." Negan growled, tightening his grip on her hips.

Sam wasn't used to letting herself go like this but the pleasure coursing through her was something she wasn't used to feeling so she wasn't even trying to ignore it to put Negan first. She gave a short nod of her head, whimpering as she felt a ball of pleasure forming in the pit of her stomach. "F-Fuck. Negan," she whispered his name, her hips stilling as her orgasm washed over her. She fell forward, resting against Negan's chest for a few moments before she realized, all too quickly, that she wasn't giving Negan what he wanted.

Tensing as she sat back up, Sam's movements resumed. She set her hands on Negan's shoulders to brace herself, moving on Negan's cock. she was focused on his pleasure this time around, leaning down to nip at Negan's jawline. "Fuck me, sir. Please," she whispered, smirking as her lips hovered above his. "Take what's yours."

Negan at first, was completely fine with Sam collapsing on top of him. He thought it was hot and adorable and he was about to wrap his arms back around her and let her rest before she perked straight back up. A chuckle left his throat, and in the back of his mind he couldn't wait to break her of this slave mentality she had built up over the course of serving disgusting pigs.

"Mmm, but you feel so good like this." Negan teased her, wrapping an arm around her slim waist. Without hesitation, he flipped over on top of her, pressing her down into the sheets. "But if you insist." He grinned, pulling her waist down closer to him as he began to thrust mercilessly into her cunt. He pounded into her, throwing his head back as he felt himself growing closer and closer, and this time, without thinking, he came inside of her, still moving his hips slightly as he came.

Sam had long since started taking birth control so she didn't even bat an eye when Negan came inside of her. She knew that men liked the thought of cumming in women and the birth control was safety to prevent her from getting pregnant. Or so she hoped. Grinning as Negan laid down beside her, Sam pressed up to his side before pressing a kiss to his jaw. "Mm, you feel so good," she murmured, dropping back against the pillows on her side of the bed.

"Do you want anything before we rest?" Sam asked, biting back a yawn as she looked up to Negan. She raised an eyebrow, more than ready to go grab anything that Negan may want. She knew that it was dangerous but she thought she could get used to this if it was on a continual basis.

Negan shook his head, completely resting back into the sheets. "No, I don't need anything besides your pretty little body lying next to me." He chuckled, yawning and stretching out his arms before pulling her close to his side. He shut his eyes, and it wasn't long before he fell into a deep sleep.

---

When he woke up the next morning, he was quiet to get out of bed and not disturb Sam. Taking the stairs down to his living room, he dropped down on the couch and ordered breakfast to his room from his restaurant, sure that by the time it arrived, Sam would be awake.

Sam slept fitfully for the first time in what felt like ages, only beginning to rise when the sun started shining through the curtains. She sat up slowly, rubbing the sleep from her eyes. When she noticed Negan wasn't around, she stilled and listened to the penthouse around her. She didn't hear anything and was left to scramble up, pulling on the dress she had worn the night before. Seeing as she didn't have any other clothes here, she didn't want to overstep by wearing any of his clothing.

Starting for the elevator, Sam headed to the first floor, hopeful she would find Negan there. She wrapped her arms around her torso, looking almost nervous as she stepped out of the elevator. She only calmed when she recognized Negan's form on the couch. "I'm sorry I slept in," she offered almost immediately, toeing at the ground beneath her as she looked down to her feet. "I don't normally sleep so late, I don't know what got into me."

Negan was quick to rise from the couch when he heard the elevator ding. "Don't worry nothing of it, I've had breakfast ordered up. Pancakes and bacon, I put your plate in the microwave to keep it warm." Negan took long strides to the kitchen and pulled the plate out and grabbed her some silverware. "I'm just glad to see you slept well."

Placing her food on the dining table, he went back to the fridge to pour her some juice. "After you eat, I'll call a taxi to take you home. Not to run you off or anything, I just have some business to tend too." He smiled. "I'll have you brought back tonight, if you'd like."

Sam eyed Negan warily as he gathered her food from the microwave. She thanked him, hesitantly taking a seat at the dining room table. While she knew that she should have expected this sort of treatment from him, it still completely threw her off that he cared enough to get her breakfast. If anything, she would have expected to be the one cooking and serving him breakfast.

Looking up after her first few bites, Sam shrugged at the mention of coming back that night. "You don't have to call a cab if you would rather not. I can drive here if you would rather save the money," she offered, taking another small bite of her pancakes. "That way we're not relying on someone else for me to arrive on time, too."

"Money isn't an object, sweetie." Negan smirked, walking over to his coat rack and pulling on his jacket. It was a nice black leather jacket. Negan zipped it up to his chest and stretched his arms out to get more comfortable. Negan was a little annoyed, knowing what he was about to have to deal with; this early in the morning.

He turned back to Sam and made sure to keep his smile on. "But if you'd rather drive, that's fine too." He walked over to her and kissed her head. "Breakfast taste okay?"