A/N: These two stories (yes two stories) are thanks to Rhia. Long story short I've been fucked in the head and nothing was getting done. I still had to adult and that means flying for my second job, consulting gigs. Rhia came up with the idea that I write a chapter a flight. Just write, and she'd give me a song (or a few songs) to help motivate the writing (if you haven't gleaned yet music is a huge part of my life/outlet). It worked. The series is named after a song by Melissa Ferrick (and holds the key maybe to the future) and the first story is after a song by Shawn Mendes (who Rhia likes and I've learned to tolerate). Right now the second story in the series is named after a Rod Stewart song, though subject to change. I have not given up on Big Eyed Fish, just a hiatus while this has been working its way out of my head. The first story is finished and will be updated at least once a week. I've been going through and updating based on events in the series, at least up to Isabella Stone episode.

Watching Raymond from a distance, Dembe's search for possible danger was interrupted by the vibrating phone in his pocket. The screen told him it was Elizabeth. For a split second, Dembe debated interrupting Raymond's and the beautiful woman's meeting to tell him of the call. This is the first time in a while that he saw a genuine smile on Raymond's face. Did he want to ruin that for Raymond?

"Elizabeth he is in a meeting." Dembe's greeting was curt. He wanted to ensure he kept an eye on Raymond, who was sitting in the open air café drinking a coffee with a mysterious woman they had just run into while leaving the hotel. They were keeping up appearances trying to ensure everyone that despite the damage Isabella Stone had done, all was well in the Concierge of Crime's world. That the steadfast reliable services remained in place, and anyone considering of making a run at Raymond would meet a horrible ending.

"I need to speak to him it's urgent Dembe." Liz pleaded on the other line.

Dembe thought it sounded like she had been crying, "What is wrong?" Dembe asked getting up to his feet to approach Raymond with the phone.

"Tom left." Liz answered, the sound of Agnes cries in the background. Tom had left long before then, but he had promised to come back. This time she had kicked him out and told him never to come back. She should have known, he had shown his true colors to her. Standing in her destroyed apartment, stepping on the broken glass of their things caused by Tom throwing them, some almost hitting her. That had been the straw that broke the camels back.

Dembe stopped mid stride and turned around and sat back down. This could wait, Raymond would likely be upset, but it could wait. "I will let him know as soon as he is out of the meeting."

"Where are you guys?"

"Chicago." Dembe responded, "We should be back this evening. Will you be fine until then?"

"Yes." Liz said trying to get ahold of herself. Realizing once again that when her world was crumbling around her, she went running to Reddington for help.

"I can have Baz come by if you need help or maybe someone from work." Dembe spoke gently to her knowing that she was still upset, and he felt guilty for letting Raymond continue his meeting.

"I will be fine. I should not have called." Liz said looking around her destroyed apartment. If Baz came, Red would probably have Tom killed seeing the destruction Tom left behind. Deciding she probably should not have called Red to tell him, "Don't tell Red. He doesn't need to know."

"I will have him call you."

"Thank you Dembe." Liz hung the phone up embarrassed for herself. What was Red going to do to help her? Threaten Tom and make him come back or keep him away? She honestly was not sure which she wanted. She knew Red would probably celebrate that Tom was gone, and probably tell her he told her so when he found out why she had kicked Tom out. People like Tom don't change; he had warned her.

Raymond could not believe the curveball the world just threw at him. Taking in the beautiful brunette in front of him, he could not help but long for what might have been. They had meant at a tumultuous time in both of their lives. Her eyes, he noted, still shined with the greenish brown fire. A little spec of black mixed into the iris here and there. Her eyes always had the alluring way to them. Drawing him in and making him almost forget that the world existed outside of their little bubble. The pale hand she had put on his was soft and warm. He could not help but think of the last time he felt that hand gently run across his cheek before she drew him into a kiss, all those years ago.

"I see that you have been keeping yourself very busy." Anna, the mysterious brunette spoke, smiling at the long-lost ghost of her past.

Raymond for his part smiled, "How have you been since we last spoke?"

"You mean over a decade ago?"

"Yes." Red chuckled, Anna had never been one to mince her words. It was what he loved about her because she never hid her feelings or thoughts. She said it and damn the consequences.

"After I got back to the States, I finished college, got a job I loved, got married, lost my job when the state defunded the program, found my husband with one of the clients, and got divorced. You know living the American Dream." She joked about it now, but it had taken years for her not to feel bitter.

Red did not have the heart to tell her that he knew of her marriage. That he had found himself standing outside the small church she and her husband were getting married in just 200 miles south of where they sat now. But he did not have the guts to go in and stop it or to watch it. Instead, he returned to his work, building his empire.

"I hope you at least took him for all he was worth." Red responded still not believing that this was happening.

"Oh and then some." Anna said, "I was able to start my own business and now we have multiple locations all around the US."

"I saw your testimony about Human Trafficking in front of Congress." Red smiled, "You gave the senator from North Carolina hell."

"He was an ignorant dickhead." Anna responded, "He deserved it. How have you been?"

"Good." Red answered though despite his best efforts he knew she saw through his guise. She could always see through the bullshit that was Raymond Reddington, as she called it.

"Well I'll pretend to believe you." Anna said, "What brought you to Chicago?"

"Business."

"AKA I don't want to know."

"Nothing too bad."

"In your world that could be selling arms Syria rebels, or bribing some world leader or blackmailing another world leader."

"Nothing of the sorts. I was meeting with a business part to assuage some of his fears." He almost flinched when she mentioned blackmail if she had only known what he had done not too long ago to get Lizzie re-instated at the FBI.

"I saw you on the news with that wanted FBI agent."

"It did go nationwide."

"You helped her, right?"

"Of course." Red answered, "She is back to being an FBI agent."

"She was the little girl, the one you saved from the fire." Anna said somewhere between a question and a statement. She could tell she made Ray uncomfortable with it, and so she switched subjects, "How long will you be in Chicago for?"

"We are supposed to leave this evening."

"We, you have someone with you?"

"The man you saw me with when we walked out of the Hilton." Red looked around for Dembe finding him sitting on a bench across the street, a phone to his ear.

"Is he your business associate?"

"No that is Dembe." Red answered.

"The Dembe?"

"Yes." Red smiled at her surprise.

"I would like to meet him." Anna said. She had only heard about Dembe when Red had first saved him from the hellish conditions. Red had called her for advice on what to do with Dembe. It had been one of the last times they spoke, even if it was only by phone.

"Of course." Red looked back across the street to see Dembe stand up and then suddenly stop and turn back to the bench and sit back down. Red sensed something was going on and Dembe was not sure if he should interrupt. "He is across the street right now."

"Waiting on you? He could have joined us."

"Dembe has become like a bodyguard in the past few years." Red said hating to admit that he kept Dembe in his life despite the danger. The mounting danger, he thought bitterly, at the memory of the most recent losses and Dembe's attempt to raise his concern for their welfare. Red never did figure out what he could say to Dembes statement about the bodies dropping around them and his reckless disregard for his own safety.

"Well he should join us." Anna responded, "Call him over."

Red stood up and waved for Dembe to join them. Dembe was putting the phone back in his pocket when he saw Red wave him over.

When Dembe was in earshot Red said, "Anna insisted on meeting you."

"Please join us Dembe." Anna said indicating Dembe should sit in one of the empty chairs at the table. "Do you want anything to drink? The tea and coffee here are divine."

"A tea please." Dembe said to the waitress who rushed over when she saw a new patron join the party.

There was a bit of awkwardness between them because Red was trying to figure out who Dembe was on the phone with, and what mess might be awaiting him. Dembe was trying to figure out who Anna was because he was sure he knew everyone in Raymond's life.

"How did you two meet?" Dembe asked breaking the silence deciding to push through the awkwardness when Raymond seemed content to stew in it.

Anna laughed, "It's a long story. I saved Raymond from being murdered on the Bougainville Island in the mid-90's."

"That is in Papua New Guinea?" Dembe asked.

"Yes."

"She should tell you about how she ended up there." Raymond said, "And it was not near death."

"Pretty damn close." Anna responded.

The waitress returned with two small ceramic teapot and ceramic cup. "I didn't know if you took milk in your tea, so I brought you some just in case."

"Thank you." Dembe smiled at the waitress before she left them to their conversation.

Anna began to speak again as Dembe fixed his tea, she noted that he did add milk to his tea. "After my twenty-fourth birthday, I decided I wanted to travel abroad. I was in the middle of graduate school and the farthest I had ever gone was Iowa, I'm originally from Illinois. So I up and quit graduate school, took what little savings I had and booked a flight to New Zealand."

Red laughed, a genuine laugh. Dembe could not help but realize how at ease Red seemed right now talking to the beautiful Anna. She was beautiful, Dembe could not help but listen to her. She had the ability to draw a person in, much like Raymond could when he told stories. It was interesting to see the two big personalities draw upon each other.

Red spoke, "Tell him why New Zealand."

"It was the farthest I could think to go." Anna spoke, "Now stop interrupting me or you can tell the story."

Red raised his hands in capitulation.

Anna continued, "Well the Kiwi farm did not work out. But I started to enjoy photography and in graduate school, I was studying human trafficking before we knew much about it. I hopped on a boat to Australia and eventually, I ended up in the Bougainville Islands taking pictures of the uprising there for various news outlets. I had been accepted among the rebels during the civil war. They knew I was the white-skin taking pictures of the conflict between them and the PNGDF. I was a neutral party; therefore, I was relatively safe from either side. Raymond had been seen meeting with the PM Julius Chan, and already had a bit of a reputation at the time. So, the Bougainville Revolutionary Army made him a top priority while he was there. I had been staying with a local family on neither side of the battle, a lot of the locals had fallen in that category. Anyways, I was walking home one night when I saw a group of the BRA beating a white man unconscious. I started taking photos of the incident, as I always had my camera with me at that time. They rushed away when they saw my camera flash go off. When I got to the man he was covered in blood, it seems they had stabbed him."

"I did not see the knife until it was too late." Raymond defended his honor, "And there were like five of them."

"Now that Raymond has established he's not a pussy," The statement drew a laugh from both Dembe and Raymond, "I dragged him away from there knowing if I left him they would come back to finish the job. At that time, I had no idea who Raymond was or why the BRA were beating him. I got him back to the house I was staying at."

"Shack is more like it."

"I'm telling a story here." Anna grumbled, "I had no idea what to do. I had not been trained in medical aid. The town doctor would not come out at night during these times. I did the best I could to staunch the bleeding and clean his wounds."

Dembe wanted to say that Red had suffered worse, but he could tell there was more to the story.

"I went to work taking photos and interviewing people the next day while I had this unconscious man in my bed, and not in a good way. The family I was staying with assured me they'd get the doctor and have him looked after. I trusted them completely because they had remained neutral through all of the turmoil."

Anna stopped to take a sip of her coffee, "So I am out interview people about the events I saw the night before, trying to figure out who the man without ID was and why the BRA attacked him. I did not get anywhere. No one knew who the mysterious American was, at least no one admitted. Though they knew he was American. That was a start, a fellow American. I had not seen another American in over a year at that point."

Red interrupted, "Meanwhile, I'm waking up with the world's worst headache in a strange place. My movement was limited due to the broken ribs I had suffered from the attack. I was in the process of searching for my clothes when three masked men barged into the room. They had assault weapons this time, and I decided best not to fight them. Instead, I let them lead me out of the shack."

"More like drag you out, by the way the neighbors described it." Anna interrupted him in jest.

"Who was there during those events?" Red said.

"Again Ray would like the record to show he's not a pussy." Anna said drawing glares from nearby patrons, of which she ignored.

Continuing his side of the story Red was animated as he talked, "As I was being pushed into the backseat of a small hatchback, I saw Anna running up towards the car screaming at the men to let me be. That I was with her and there was no need for this."

"They did not listen to me. They turned their guns on me and told me to let this go because it was in my best interest if I wanted to remain safe. I, of course, did not accept this not right away, but the husband and wife I had been staying with dragged me into the house while the men drove off with Raymond in the backseat. It was then I found out the couple had turned him in for money. The wife told me that the words on the street were that Raymond was in town brokering a deal between Halcyon Aegis and the PNGDF via the Prime Minister. I was upset that the people, who I had thought were good people, had sold an injured man to the BRA. At the time, I thought the rumor was complete nonsense. The Prime Minister was not a horrible man, and I did not think the Australian government would allow him to hire mercenaries to stop the BRA."

Anna stopped her story when the waitress returned to check on them. As soon as the waitress was gone she started her story again, "I talked to everyone I knew remotely associated with the BRA over the next week trying to locate what happen to the nameless American. I was ready to give up hope, assume that he was likely buried in the mines. It was the end of the week when I finally got more information from a young woman who was dating one of the leaders of the BRA. It seems they had been trying to get the nameless American to broker a deal for more weapons. He was being kept in one of the leader's hideouts."

"The resistance had little money to get the arms, and at the time I was still building my empire. There was no way I could get them the weapons without capital. They did not seem to understand this." Red grumbled.

"Cause otherwise he'd never need to be saved by a girl. So let the record show that Raymond is a strong one-man show. John Wayne should take notes from him." Anna joked before continuing her story, "Eventually, I convinced the woman to take me to him. That maybe I could help being American. The poor girl had very little education and just assumed because I was American, I was likely rich and could help with the money issues. When I got there, I found Raymond chained in a corner of a cement room. One eye swollen shut and the other rapidly approaching. The knife wounds both new and old were severely infected from lack of treatment, and he was severely dehydrated. They had been withholding food and water in hopes of breaking him."

She did not mention that part of his issue had been from withdrawal from opium. She did not want to out Raymond to Dembe if the other man did not know about Raymond's past indiscretions. "I could not convince them to let him go, that he was in no shape to broker a deal for anyone. Eventually, all I could do was offer them the money I had, which did not amount to much, if they would let me treat his wounds. The leader decided that if he could not broker the deal, then they could sell him as slave labor or possibly just sell him to the highest bidder. A man like him had to have enemies. That was how they were going to raise funds to get more weapons. I convinced them I could help them get him healthy. That I would stay quiet, and they had little reason not to believe me because the family I had been staying with had sold them the American and I had been known to be partial to the BRA. The week before the BRA raided a PNGDF camp, where they would kill 12 soldiers and take five hostages. The PNGDF were out for blood. The PNGDF happened to raid the very house I found Raymond in while I was trying to treat him. I managed to slip out of the house, somehow dragging him with, into the car I had borrowed from a friend. I got him to the local doctor. The doctor was afraid to treat him, knowing he was the American everyone from the BRA to the PNGDF were after. I convinced him to at least stabilize him so I could get him off the island."

"How did you get him off the island?" Dembe asked having never heard Raymond talk of this story, and wondering why someone would go to these great lengths for a stranger.

"I had become close with one of the pilots for the local mine. He flew in and out of the country with VIP's all the time. I begged him to fly us out to Kimbe on West New Britain. I knew someone who had a flat there that we could stay at, and I knew a doctor there too. So it seemed like the best place to go because if Raymond was who they said he was, I knew I couldn't drop him at the hospital."

"Why would you go through all of this for a stranger?" Dembe asked the obvious question.

"The day before, I had seen him take his watch off and give it to one of the orphans that begged along the street. He returned ten minutes later with water in bottles and food from one of the restaurants. He handed out the water and food out to the orphans. I had taken pictures, but did not approach him because the PNGDF had been with him disapproving of his actions, but all the same doing nothing to stop him. And like I said I didn't believe the rumor that he was a big bad Westerner Outlaw."

"Whatever the reason, I was extremely grateful at the time because I would not have lasted much longer with the BRA." Raymond said jumping in knowing that Anna's main reason was she was just a good person and she saw another human in pain, and reached out to help.

"How long did you spend together?" Dembe asked trying to place the timeline as to when Anna had entered Red's life versus when Dembe had.

"About a year. It took me a month to recover from my time with the BRA. Anna stayed with me the entire time taking care of me."

"Was he as bad a patient then as he is now?"

"Yes. It was a constant battle to get him to let me change bandages, wrap his ribs because the wrap felt restrictive, and never mind when he had to start walking to ensure pneumonia did not set in while his ribs healed."

Dembe and Anna shared a laugh over the great pains it took to get Raymond Reddington to do what the doctors ordered when he was injured

"After I finished convalescing, I convinced Anna to come with me. We traveled all over Europe and South America for the next few months." Red did not mention that he had been working the entire time and that it was a struggle to keep her out of the business.

"But as all good things, eventually it had to end." Anna picked up the story, "Raymond bought me a ticket back to the states, and dropped me at an airport in Brazil." Anna then spoke in a stage whisper to Dembe, "I think he got tired of traveling with me."

"Not true." Red stated, he could not tell her that she had become a liability. That as he became more powerful, a target was being painted on her back. That it needed to seem like he was getting rid of her, and moving on because they would come after her. Like they did his family.

"I came back to the states, and used the knowledge I had gained while traveling to go back to school now with a focus of studying transnational crime, and I only kept up with Raymond via stories I heard on the news."

Neither spoke about how the last few months together they had fought constantly. Anna had become pregnant with Raymond's child, and he did not want her to have the child. He had only told her bits about his life before he became one of the most wanted criminals in the world. She knew he had a family including a daughter, but he never spoke beyond that. She sensed that he had not left them by choice, and that he missed them terribly. She had also sensed his fear for her safety and the unborn child's. What would be the last week of her first trimester, she had a miscarriage.

The loss of the baby, even when Raymond had wanted her to abort it, had gutted them both. He had pushed her away, cruelly, citing that it had been fun but nothing more than that. It had taken her years to realize his cruel words for what they were, his pushing her away because he feared what could be, and what could happen to her.

What she did not know was she was the first woman he had slept with since his wife. That she had helped him heal not just physically but mentally. Before he had saved him, he moved from one reckless deal to the next trying to get as much information and money as he could to help him track down what happened to his family that night.

But the lack of knowledge into the other was not a one-way street. Anna had never told Raymond about his being her first love. That every man she meant after he had been measured against him. When she married the man who had been her husband for those seven years, had been her settling. That to this day, her heart would flutter whenever she saw a picture of him on the TV asking for help in locating the fourth most wanted man in the world. That seeing him today in the most improbable way had reminded her how much she cared for him. It had been pure torture when he called her about Dembe and what to do with the boy. She had been ready to drop everything just to go help him and be with him.

The unspoken words hung between them, Dembe ignorant to each of the other occupants of the tables thoughts.

"It has been a long time since then." Anna said pulling herself away from the past, "Raymond moved up in the most wanted list and the rumors I hear from colleagues is that he a major player in transnational crime. What my colleagues would say or do just to get a few moments with him or to study him."

"So you are an academic?" Dembe asked.

"No. I run not-for-profit helping victims of human trafficking."

"International justice mission?" Dembe asked remembering that Raymond had donated large sums of money to that organization over the years.

"Yes. How did you know?"

The subtle look from Raymond told Dembe to lie, "I read it on the tablet sticking out of your purse when I walked up." Dembe looked almost embarrassed, "Habit sorry."

"Nothing to be sorry about." Anna laughed having seen Raymond's subtle look.

The bill came and Raymond insisted on paying and Anna noticed that he left more than a generous tip for the waitress.

"It was nice to catch up." Red said wishing for more time with her, but he knew he needed to get back to D.C.

"Of all the gin joints in all of the world." She quoted the movie she had forced him to watch a few hundred times, "It was nice to see you again." She pulled him into a hug, feeling that despite the way he looked, he still had muscle mass.

"We should catch up more often." Red said not wanting to let this moment pass.

"If you are ever in the D.C. area you should look me up." Anna said.

"D.C?" Red looked shocked at her statement.

"I just moved there a few months ago. I was spending so much time on Capitol Hill that it seemed logical to just set up there. So I bought a small townhouse there and I have a friend who lives in my flat here that doesn't mind that I stay a few weeks in the year."

"I actually am in DC a lot these days."

"Really." Anna said truly surprised, "I would think it would be hard for you to move so easily in the United States."

"Quite the contrary." Red said, "We should catch up in DC sometime. I am heading back this evening."

"I am on standby for a flight out tomorrow."

Red seized the chance, "It just so happens I have a private jet. I could easily fit one more if you wish to go back tonight."

"Are you sure?" Anna said not even thinking twice about accepting a free flight from one of the most wanted men in the world. He was her Ray.

"Of course. You can keep Dembe and I company. We know each others stories already."

"What time? I still have a few more meetings…"

"Whatever time works for you." Red stopped her mid-sentence, "It's one of the nice things about owning a private jet. You can leave whenever you want. Oh and no pesky security."

"Will seven work for you?"

"Yes." Red said. "Do you have a pen and paper? I can give you my number for the day and you can call me when you are ready. Dembe can pick you up and bring you to the plane."

"I can take a lyft there. It's no big deal."

"I insist."

She watched him as he scrawled the number for her.

"I will also have dinner brought aboard. Anything specific you would like?"

"Whatever." Anna said, "You know me."

"I will see you this evening." Red smiled as he handed the paper and pen back to her.

A/N: Thanks for reading and bonus points for anyone who can figure out how Anna got her name.