This is set some time after the finale and I'm working under the assumption they are staying together. I understand this is an very unlikely scenarios but that is the beauty of fanfiction!

All normal disclaimers apply- I've nothing to do with The Blacklist and make no money this is solely for entertainment. Also a huge shout out to SilverArrow82 (Ashton) for being an amazing Beta.

I hope you enjoy!

"I was beginning to think you'd never come out of your room," Red remarked softly, taking a generous sip from his crystal tumbler.

Liz sat opposite Red on the chaise lounge, tucking her bare feet beneath her and leaning against the armrest. "I'm still processing everything."

"Such as?"

Shooting a glare at him, she leaned forward to pour herself a glass. "The terribly uncomfortable accommodations."

Red raised an eyebrow at her. "Liar...now drink."

Watching him curiously for a moment, she raised her glass and took a sip. "You know, if we are going to play Truth or shots, we're going to need a lot more alcohol."

"Truth or shots?"

"Abbreviated version of the drinking game, Truth, dare or Shot," Liz replied casually, sitting back to get comfortable. "I just skipped the boring dare part."

"A drinking game, what fun! I haven't played one in years," Red commented quietly, leaning forward to refill his glass. "So what are the rules?"

Liz looked at him in shock for a moment, but eventually just shook it off; they had been through way too much together this past year for anything else about him to surprise her. "One person asks a question, and you either have the choice to answer honestly or take a drink. Normally it would be played with shots, but scotch will do."

"Nonsense!" Red replied, picking up the bottle of scotch and taking it to the wet bar. "This scotch is over 50 years old, and every single drop should be savored; not machine gunned like adolescent boys at a frat party. I have some vodka here somewhere..."

Watching Red rummage through the bottles, she just shook her head. "I was just joking Red, we can't play that game."

"Ha! I knew I had some!" Red cried out, lifting two shot glasses and a bottle of Vodka before stopping dead in his tracks when he realized what she had said. "Why can't we play?"

Glaring at him, Liz took another sip from her glass. "Hmm let's see: I ask a question, you have to take a shot, because honesty and answering questions aren't something you are capable of. While on the other side YOU have to ask me a question, but you already know everything about me. Even things I don't know about myself, so yes, grab your stupid glass of scotch and we can sip in silence and savor this drink that's just as old as you until we both pass out drunk.

Red stood staring at her for a moment. "That's a low blow, Lizzie." Moving back to the chair, he set the bottle and shot glasses down. "First, I have never once lied to you. Something only once of us can admit honestly. Second, age is only a number, unless it is fifteen, then it gets you twenty."

"Did you just quote a rap song?" She asked incredulously.

"Are we starting the game now then?"

Watching him take his seat, she sipped her drink again. "I'm not playing."

"I'll make you a deal. Tonight only, I'll answer everything I can that won't put you in danger." This statement piqued Liz's interest, causing Red to continue, "But it extends only until sunrise, everything said tonight will not be spoken of again."

"So anything I ask-"

"Within reason," Red interrupted to remind her.

"Anything I ask...within reason, you promise to answer honestly, no matter the question?"

"No matter the question, though I'd prefer you stuck to more interesting questions like 'boxers or briefs'," He replied, winking at her while pouring the vodka into the shot glasses.

Liz thought long and hard about what she wanted to ask him, sipping her scotch slowly. Red had once told her that he had answers to questions she hadn't even thought of yet, but she intended to try.

"How did you know my father?"

"It was my job to know your family."

"What does that mean?"

"Uh uh." Red wiggled his finger at her as he sat back against the chair. "My turn."

Lizzie glared at him as he tapped his lip, seeming to contemplate his first question with deep thought.

"I'll make the first few pretty easy, although you obviously haven't extended me the same courtesy. Who is your favorite singer?" He inquired.

Raising a skeptical eyebrow at him, she answered, "Cat Power."

Liz wasted no time with her next question. "What does that mean, "it was your job"?"

This time Red leaned forward, lifted the shot glass, and downed it.

"Bastard," Liz seethed as he set the glass back down, and began to fill it again.

"Such language. Who had the honor of being your first kiss?"

"Roman Krass. You told me that my father was dead...did you kill him?" Liz asked, with a stone cold expression on her face.

"Not directly, no." Here Red paused, his answer seeming to affect him and throw him off his normally calm and cool exterior. Taking a moment to compose himself he replied, "Obviously, I need to ask better questions to throw you off your game a bit."

"I want answers, Red."

"I will give you answers, but some you aren't ready to hear, Elizabeth," Red shot back sharply. Standing quickly, he roughly pulled at his tie and began undoing it as he moved to the wet bar once again.

The room fell deathly silent at the mention of her full name. She'd struck a nerve. Deciding it was better to wait him out, Liz continued watching his profile to see what his next move would be.

When the knot in his tie was undone, he pulled it from around his neck and threw it on the bar. "What age did you lose your virginity?" He asked without turning around.

Liz was taken aback at first by his question, chewing on her lip she contemplated whether or not to answer his very personal question. Making up her mind, she picked up the shot glass and downed it, slamming the empty glass back on the coffee table.

Red glanced over his shoulder at the sound before reaching for his humidor box and removing a cigar. Taking the cutter, he clipped both ends before picking up his lighter and moved back to his seat.

The pair sat silently, staring at each other. Finally, Liz nodded at his cigar. "I thought we discussed this before, are you really going to light that?"

"Yes," he replied, lifting the lighter to the end of the cigar and puffing a few times to make sure the flame took. "I smoke when I drink or if I am stressed, and you sweetheart, have managed both of those." Taking a long drag on the cigar, he savored the taste before releasing the puff of smoke upwards and away from her. "Have you ever kissed another woman?" Red asked pointedly.

"It's not your turn, you just asked about my virginity," Liz retorted.

Tilting his head, Red raised an eyebrow at her. "Yes, and you asked if I was going to light this cigar. Such a silly question, but nevertheless, a question."

"But-"

"Uh uh, rules are rules, Sweetheart. Answer or drink." He nodded to the shot glass that still sat empty from her last question.

Picking up the vodka bottle, she poured herself a glass and took the shot, quickly refilling the glass once again. Looking up at Red, she glared at the wolfish grin on his face. Deciding to get back to her original line of questioning she asked, "Were you responsible for the fire?"

Red was in the middle of taking another long drag on his cigar when she asked her question, causing him to choke on his inhale and cough a few times. "Indirectly, yes."

Liz sucked in a deep breath at his answer, pushing off the chair to get away from him. "You killed my family? You tried to kill me?"

Red knew better than to push her right now, the only thing that would soothe this situation now was as much truth as he could give her. "Your Father tried to kill you. I was part of a team whose mission was to capture him alive. I helped to plan the attack, and ran comm point on the mission, but he was tipped off and ready for my team."

Liz remained silent, but her eyes never left him as she absorbed all the information he was providing for her.

"You and your mother were supposed to be away visiting family, but your father, knowing our plan, canceled the visit and used both of you against my team." Red closed his eyes against the dark memories that came flooding back. "He locked you and your mother in different rooms during our incursion, then he set fire to the house. I could hear your screams for help."

Continuing to watch Red, Liz moved back around the chair to take her seat again. Slowly lowering herself back onto the chaise, her own memories assaulted her as realization finally dawned on her. His admission of being indirectly responsible, his desire not to admit how he knew her, or why she was important to him now made a lot more sense. "You saved me? It was you, not my father that saved me that night?"

"Yes." Red's voice rumbled with a deep timbre, obviously affected by unexpressed emotion. "Someone betrayed me that night and set into motion a hellacious set of events that changed both of our lives forever." At this, he opened his eyes and locked onto Liz's.

Liz felt the weight of his gaze hanging heavy between them and had to look away. "Why not just tell me that?"

"It isn't just your story, Lizzie," He reminded her, putting his cigar out to pick up his glass of scotch and draining it in one swallow. "It is only the beginning of a truly painful story for me."

The silence between them began to stretch and was bordering on uncomfortable. A little voice in the back of her head kept whispering, 'You should have listened.' It was a very sobering thought. True...he was using her for his own agenda, but he also went to great lengths to protect her and see her succeed. Once again, when provided the perfect opportunity, he didn't lie to her, no matter the pain it would cause both of them. She knew there were more answers she needed, but there would be a time and place for that. Tonight, was not that time nor place. She was emotionally raw from recent events with Tom and Berlin. The weight of the truth of what actually happened on that fateful night, now also hung heavy in her heart.

Her lack of sleep and the alcohol wasn't helping her current mood or the state of her emotions. She had come to the terrifying realization that no matter what happened between them, she needed Raymond Reddington. She needed his honesty; he was the only one in her life that had never lied to her. She needed his protection, and terrifying as it was for her, she needed contact with him. It had happened over time, and she was loathe to admit that she needed him to hold her hand, and tell her she could depend on him. She needed him to hold her, and tell her she would be ok.

Red sat silently, watching the myriad of emotions play across her face. He knew this whole night was a bad idea, but their relationship was so fragile right now, he needed to connect with her again; but this had backfired on him. Sitting forward, he rested his head in his hands in defeat.

Liz observed Red's movements and felt the tug at her heart. "I thought you were supposed to savor that scotch?" She commented softly, watching him to gauge his reaction.

Red looked up and barked a laugh at her before shaking his head. "This little back and forth we do tends to throw a man off his game. Refill?" He asked, standing up and reaching for both of their glasses.

Liz watched him take their glasses to the bar once again, gently lifting the crystal decanter of scotch to pour more than three fingers worth into his own glass before refilling hers. He paused at the bar, staring down at the glasses for a moment too long. "Red?"

He didn't bother answering or looking back at her, and instead picked up his glass and downed the entire thing once again; squeezing his eyes shut against the burning sensation from the large amount of alcohol. As a seasoned drinker, he didn't experience the normal burning sensation, but in such volume, even he wasn't immune.

When she received no response, she started to panic. She knew how to handle angry Red, sarcastic Red, she had even learned to return fire against his sharp tongue when she got too close to any of his truths. She did not know how to handle silent Red. Liz had only two choices: she could run away like a frightened little girl, way in over her head, or she could stand her ground, and face the most terrifying thing in her life: Raymond Reddington, the Concierge of Crime, and everything that came with it. Deciding to take the bull by the horns for the first time in their short relationship, Liz made the choice to take a bold approach at getting his attention back. "Ok. It's my turn, right?"

Red snorted loudly, taking another long swig from his glass before picking up her glass and returning to his own chair. "Haven't I been flayed enough tonight?"

"Yes," Liz replied, accepting her glass and setting it on the coffee table between them as she watched him take his seat. Gathering what courage she could muster, she looked directly at him. "But I have more questions."

Taking another sip from his glass, Red waved his hand at her. "Be my guest, but don't be surprised by the number of shots I take, depending on the line of questioning you decide upon," he finished, and tipped his glass to her and took another sip.

"Normally, there are only two reasons someone would be as protective as you have been over me," Liz said, adjusting herself in the seat. "The first, we've already discussed, but the second, well that is something I'm interested in exploring."

This comment caught Red's attention, causing him to pause his glass in the middle of moving to take another drink. "Go on."

Realizing she finally had his full attention, she put her big girl panties on and dove head first into a very dangerous line of questioning. One she knew she wasn't actually ready for, but needed to hear to be able to work out her own feelings. "Boxers or briefs?"

Lowering his glass, he leaned forward towards her. "What are you playing at Lizzie?"

"Uh uh, rules are rules... Sweetheart," Liz parroted Red's earlier comment. "Answer or drink."

"Are you sure you want to go down this rabbit hole with me?" Red kept eye contact with her, waiting for her response. When her silence began to stretch out, he continued, "Because this questioning would blow away any lines we might have left in the sand, and we may not be able to forget about them come morning."

Liz understood what he was trying to tell her, and in that moment she made a choice. These answers might have been just as terrifying as the truth about her past, but she needed to know. She decided to hold her ground and forced herself not to blink or back down from him as she leaned towards him. "Boxers or briefs?"

"Neither...too constricting," He replied, winking at her and smiling at the crimson that worked its way up her cheeks. They could both feel the shift in the air after his answer as both released a breath they weren't aware they had been holding. Sitting back once again to get comfortable, he stretched his legs out before him, crossing one ankle over the other and draping one arm over the back of the chair. "Are you interested in Donald?"

Liz was trying so badly to make a conscious effort to divert her eyes to other areas of his body after what he had just disclosed to her, that she almost missed his question. Choking back a laugh, she covered her mouth. "You're joking right?"

"That's not an answer."

"Good God, no!" She shot back, before asking him, "Were you sleeping with Luli?"

"No," he answered without skipping a beat.

Liz looked at him quizzically, "But she-"

"She stayed with me, and when she used to get ready she preferred a button up shirt so as not to muss up her hair, but I was not sleeping with her." He figured his response must have been sufficient as she seemed to relax. "Have you ever gone skinny dipping?"

"Yes. How many women have you slept with?"

This question caused Red to pause, he'd learned long ago never to give full disclosure about his relationships to anyone. Picking up the shot glass, he downed it, setting it back onto the table and filling it once again. "Sorry, I don't kiss and tell."

"Good to know." He thought he heard her mumble, before asking his next question, "Are you a lights on or a lights off kind of girl?"

Resisting the urge to answer, she picked up her shot glass and took the shot, then made a face. "Blah."

Red couldn't contain his chuckle as he watched her refill her glass." I think we are getting close to your limit."

Watching Red take a sip from his glass of scotch, she narrowed her eyes. He was right, she was getting quite tipsy. Liz tried to clear the haze from her mind to come up with something that would level out the playing field once more. Biting her lip softly, she decided it was time to go big or go home with her next question. "Have you thought about me naked?"

Red startled, sitting forward quickly as he coughed up the drink he was in the middle of taking. Brushing off any excess that had landed on his chin and shirt, he glanced up through hooded eyes and watched a triumphant Liz recline back on the chaise, stretching out like the cat that got the cream. It was possibly the most seductive thing he had ever seen, and she was still fully dressed. While he finished cleaning up his mess, he casually adjusted himself before crossing his legs as he contemplated his answer.

Laying back helped her slightly spinning head, but it didn't help the knot in her stomach at his delay in answering. Liz figured he would have jumped at the opportunity to answer this question had he been interested in her that way. Perhaps she had overplayed her hand. She could feel the panic begin to rise when a throaty answer drew her attention back to him, "Yes."

When he finally caught eyes with her again, he asked his own question, "Why do you watch my lips when I talk?"

Rolling slightly to the side, she rested her head on her hand. She had no inclination to take another shot, so she answered his question honestly, "Because I wonder what your lips feel like and how you taste."

Neither blushed nor squirmed under the others gaze, they couldn't take their eyes off one another as a different sort of tension began to build between them. They were dangerously close to the point of no return in their little game, and he wouldn't be the one to push them over that cliff; between the alcohol and emotions running high, he needed her to be absolutely sure before they moved forward from here. "Are you trying to seduce me, Elizabeth?"

"I'm just being honest, Raymond," She replied softly, pushing herself into a sitting position before moving to stand slowly. As she stood there before him, she reached out her hand. She didn't know what she was doing, or even where she wanted this gesture to go, but she knew only one thing, she needed his touch.

Red didn't waste a moment debating his reaction to her movements. The sound of his full name rolling off her tongue was his undoing. She could have asked him for anything, asked him to move heaven and earth, and he would have done it for her. Pushing himself out of the chair, he moved gracefully around the coffee table and laced his fingers through her outstretched ones. When their hands connected, he gently tugged her to him and wrapped his other arm around her midsection to close the gap between them.

Liz released his hand and began ghosting feather light touches up his chest, finally coming to rest against the stubble of his five o'clock shadow. Her gaze remained fixed on his lips as she moved her thumb over his lower lip, mumbling under her breath, "So soft."

He didn't dare move. Holding her close to him like this was more than he could have ever imagined after the turmoil of this past year. He would accept anything she was willing to offer him, be anything she needed him to be; tonight he just wasn't strong enough to turn her away.

Gently sliding her hand around his neck, Liz pulled Red to her and kissed him. It wasn't soft or unsure, it was deep, urgent, and full of need. Hands roamed all available surfaces before eventually the need for air forced them apart.

Resting their foreheads against each other, they panted while trying to catch their breath. Moving her right hand to rest on his clothed chest, she felt the steady pounding of his heart directly below her hand. Its pace seemed to be racing in time with her own. "I don't love you, Red," she told him, her voice sounding breathy with desire.

Red didn't bother to open his eyes, but nodded his understanding. "I know, but I'm confident you will someday."

"You're a monster," she continued, unsure if she was telling him or trying to convince herself.

This comment caused Red to open his eyes and look at her. When he found her eyes still closed, he continued, "I'm not concerned with your perception of who you think I am at-"

"Of who I know you are-" She interrupted, not allowing him to finish.

"Look at me," Red demanded, making eye contact with her once she opened her eyes. Once he felt he had her full attention, he continued, "You don't know anything about who I really am, but someday you will. Someday, I will give you all the information you need. Then and only then, Lizzie, can you judge me for who I truly am. Until then, I can be anything you need me to be."

"Red, I do want you, and after everything that's happened recently, I need you; but there's no way that I am ever going to be able to love you." Liz didn't want there to be any confusion about what tonight was about.

Red nodded to her as he stepped back. "Two out of three ain't bad," He said quietly, extending his hand towards her. "If this is what you truly want, then take my hand Lizzie."

Glancing once at his outstretched hand, she grasped it tightly. "Just for tonight?"

"Until sunrise," he replied, leading her by the hand out of the room and towards his room.

AN: A little angst never hurt anyone and I followed it up with as much fluff as I could just for Sarah and Simone! I hope you have enjoyed! As always please leave me love or hate, I just like to hear what everyone thinks!

Always,

Lady