I have no idea but I just could not get this idea out of my head. Little of an A/U. The only change is that Emma kept Henry when he was born and then later gave him up for adoption. May be a little OOC so sorry for that.

"Wanna Hear A True Story?"

"Swan." Killian looked over to the docks and saw Emma sitting letting her legs dangle off the edge. "Emma!" She didn't respond and he figured it was because she simply could not hear him. He walked a bit closer hoping if he kept repeating her name she would turn around to face him. He saw her head tilt back and look up at the stars. He didn't know why but a weird feeling went through his chest when he followed her gaze in perfect time to catch a shooting star flying across the atmosphere. He continued to walk towards her hands in his pockets for it was fairly cold in New England especially in the middle of December. He walked closer to her and noticed that she didn't even have a coat on. He figured she would be shaking from the harsh cold air but to his surprise she remained motionless. Only her steady breathing causing her abdomen to expand and collapse. He eventually stood behind her only a few feet remained in between them.

"What are you doing here Killian?" Her voice was dull, lifeless even. Usually his heart filled with joy whenever he heard her call him Killian. But now it was the total opposite. Maybe even worse than when the crocodile ripped his heart from his chest. "Emma, darling it's freezing." He told her.

"That's what happens in December." Lifeless. Her voice was lifeless.

Hook removed his jacket from his own body and knelt down to place it around her shoulders. "You're going to become sick love." That was all he said, not wanting to push her to speak. He swung his legs around to the edge. Replicating the woman next to him.

She took both of her hands and wrapped the leather jacket tightly around her. "Thank you." It was a mumble but he didn't care, it was something.

He kept his mouth closed. Again, not wanting to push. Why the docks? He wondered. He knew that she was fully aware that he liked to spend his time there. But his mind didn't focus on that much. His brain to too consumed by the thought that his Swan was suffering. He bit his tongue from asking what was wrong. He didn't care if he bit a hole; he wouldn't ask her. No matter how much it pained him.

"Can I tell you something?" Her voice was small, highly unlike the Swan he knew but no part of him cared.

"Of course." He replied looking over at her. Her eyes remained straight but no of that mattered to him.

"Do you ever feel like a failure?"

His heart shattered. Filling with pain; more pain than the crocodile could have ever caused. "Emma,"

"I could have kept him." She continued. "I could have found a job."

His eyebrows furrowed. He didn't bother asking what she was talking about knowing if he gave it time he would get the answers.

"I just couldn't bear seeing the pain in his eyes anymore. Every night he cried. He sobbed." She swallowed down her emotions and found a star in the distance to stare at. "I couldn't even fed him." She let out with a wounded breath. "He was crying and I left him. Let him to cry."

He continued to watch her. He noticed her breathing was steady but not in the good way. It was almost as if she was breathing out all the hope she had in her. Letting it escape into the world.

"Henry deserved so much better." She added. "I let him suffer...I had to make money."

"What did you do?" He bit down hard on his tongue as soon as those words escaped between his lips.

She let out a fake laugh. One that caused him to feel even more pain. "I sold myself."

Killian swallowed. He knew what she ment. There were many woman in the Enchanted Forest that did the same thing. And being a pirate he came across many. And he abhorred himself knowing he didn't only see those woman when passing on his ship.

"He was hungry. And the only way for me to feed him was to have sex for money." She looked down at her feet then lifted her eyes to look across the body of water. "That was the only way to put bread on the table."

It was at that very moment that he despised being in his own skin. Knowing that even if it was in a different realm he once was one of the men, seeing it as only a good time.

"Neal left, so it's not like I could ask him to do anything."

"Emma-"

"Every morning I woke up and I wished I gave Henry up." She took in a breath and began to speak at a quicker pace. "And now I'm ranting to you which I don't even know why and I just can't seem to get the memories out of my head of Henry just...crying. I've tried so hard to focus on how he is now but then my head just reminded me that he is only this way now because of Regina. She raised him and gave him a wonderful life and if he stayed with me he probably would end up as a damn crack-head."

Killian was at a loss for words. Even if he knew what to say he had doubt that he would be even able to get the words out of his mouth. She still hadn't made eye contact with him. Not once. "Emma?" He managed. "Look where you are now love."

Her eyes didn't leave the horizon causing him to think harder.

"You have your son, people who care about you greatly. They would go to the end of the world just to see you smile." Her lips cracked a smile even if it was sarcastic he didn't care. "See? Beautiful." She looked over at him looking straight into his ocean eyes. He decided to continue seeing pain still plastered her expression. "You are far from a failure Swan. You're a bloody hero. A princess even. A genuine princess who one day we will get back to the Enchanted Forest and you will become Queen. And you will rule our world and you will be bloody marvelous."

She tilted her head down causing her chin to touch her neck. Queen? She never had that thought even enter her brain. Sure she knew her mother was a princess but never had she taken time to link the pieces together.

"Look at me love." He told her, "All around you are people who have done things they are far from proud of. And what you have done in the past has brought you here...home."

I have absolutely no idea what the heck I just wrote or where this idea even came from but for some odd reason it just wouldn't leave my head. I guess I just really like the idea that we don't know much about Emma's life after she got out of prison aside from becoming a bail bondsman. Anyway, thanks for reading. Maybe one day I'll write something to do with Hook's past with his father, if there is any interest in that.