Sam and Dean stayed at Lily's for a few more days, until they got wind of a possible case in Rhode Island.
She didn't hear from Dean again until the following summer. She was in the study at the cabin, with several books spread across the desk, when her cell phone rang. She answered without checking the caller ID.
"Hello?"
"Hey, Kitten."
"Hey, Tiger," she said with a smile. "It's been a while."
"Yeah, it has. You wouldn't happen to be at your cabin, would you?"
"As a matter of fact, I am."
"I'm in Ohio. Headin' your way. You up for some company?"
"You and Sam? Anytime."
"Just me this time, sweetheart."
She could almost see the grin on his face. "How soon can you get here?"
"Give me five hours."
Lily went back to her research while she waited for Dean to arrive. Almost five hours later she heard the rumble of the Impala. She opened the front door just as Dean was coming up the steps of the porch. Before she could say anything, Dean grabbed her, pulling her into a hard kiss. He backed her into the house, shutting the door behind him with his foot.
"Are you alone here?"
"Yes," she answered.
Before she could catch her breath his lips were on hers again. He began moving her toward the bedroom as he removed her shirt. They left a trail of clothes to the bed where he attacked her body with his mouth, his hands roaming and squeezing her flesh. She gasped as he entered her roughly, finally finishing hard and fast, both of their bodies trembling.
Dean rolled onto his back, covering his face with his hands. Lily pulled the sheet up around her, glancing at Dean. She could tell something was off.
"You wanna tell me what's up with you?"
"It's a long story."
"I'm not going anywhere."
Dean filled her in on everything that happened since they last saw each other, the most significant news being Sam's death and Dean's demon deal. Lily sat up, holding the sheet to her.
"Dean... how could you?"
"You know, I already got this from Sam and Bobby. I don't need it from you too."
"One year, Dean?"
"One year. Sam's been going crazy trying to find a way out of it, but I don't think we will."
They were both quiet for a few minutes as Lily took everything in. She finally brought it back to their current position.
"So, what was it that brought you here?"
"The case we were working in Ohio. It turned out to be a couple of demons. I trapped one, and she turned around and trapped me. While I was waiting for Sam to show up and save the day, me and the demon actually had a civilized conversation. We talked about Hell, and the fact that I'll be there soon. I guess it got me thinking. Anyway, I really needed to let loose, but I didn't have it in me to wrangle in a girl tonight." He turned his head to look at Lily. "I needed something familiar."
She leaned over and kissed him. He held her to him with a hand at the back of her head. When she pulled away, she saw a sadness in Dean's eyes. She lay her head on his shoulder, resting her hand on his chest as he ran his hand up and down her arm.
"So," she said, "did you leave Sam in Ohio to come here?"
"No. Bobby showed up to help. Sam went with him back to South Dakota. What about you? You workin' on anything?"
"Dad has me doing some research for him."
"You ever tell him about our little get togethers?"
Lily laughed. "Tell my father that I'm Dean Winchester's friend with benefits? Do you have a death wish?" As soon as the words were out of her mouth she regretted them. "Dean, I didn't..."
"It's okay."
They were silent for a moment.
"I'm gonna help," Lily said, sitting up a bit.
"Help how?"
"I'm gonna help find a way to get you out of the deal."
"You can't."
"Why not?"
"If I break the deal, Sam dies. I'm goin' to Hell, Lily. No one can stop it."
It took a while, but Lily eventually fell asleep in Dean's arms. She woke before dawn to find her clothes in a pile where Dean should be. He was gone.
Lily spent the following months balancing cases with doing research to find something that could help Dean. She called him a couple of times to discuss it, but he would get mad. He said it was bad enough dealing with Sam not accepting it. So, she stopped calling Dean and kept in touch with Sam. There was never any good news.
She was surprised when Dean showed up at her door the following April. He looked exhausted and lost. She hugged him, then they sat on the couch to talk.
"Where's Sam?" she asked.
"I dropped him off at a hotel nearby. We're headin' back to Bobby's. We may have gotten the name of the demon who holds my contract, so we're gonna try to find her."
"What's her name?" Lily asked. Dean just shook his head. "You're not gonna tell me?"
"No. I don't want you goin' after her or doin' something stupid."
"Dean, you have less than three weeks left. Let me help!"
"No. It's not your fight. I don't want you getting hurt."
"I can't believe you! You know, Sam told me that you finally admitted you don't wanna die. He thought it had something to do with some woman... Lisa. He said she made you think about a normal life. Maybe you should go see her so she can talk some sense into you, so you'll accept any help you can get."
"I can't go to Lisa. Sure, she knows what I do, but she'd never understand this. And if I do die, which I probably will, it'll just end up hurting her."
Lily shook her head and moved to stand up, but Dean grabbed her arm, pulling her back down.
"Look, it's like you said, I have less than three weeks. Now that we have a name, Sam will keep me working 'til the very end to get out of it. I came here for one more night. You know how to take my mind off of things," he said with a slight grin. Lily didn't smile back. "I'll understand if you don't want to."
Lily placed her hand on his face, leaning in to kiss him gently. When she pulled back she stared into his eyes.
"How could I say no?"
They went slowly that night, savoring each touch. Lily made sure to do all the things that she knew pleased Dean. She came near tears twice, knowing that Dean would be dying. Worse, that he would be going to Hell.
Dean didn't stay. They got dressed and she walked him to his car.
"Dean, promise me you'll try as hard as you can to get out of this."
"I promise."
He kissed her one last time before getting into the Impala and driving away.
Three weeks later, Lily got a text from Sam. All it said was, "He's gone."