A/N - Imagine that Lucifer made another visit to Sam sometime between his revelation in "Free to Be You and Me" and the phone call between Sam and Dean in "The End."
"Hello, Sam."
The young man jumped, mentally cursing angels and their overly polite greetings.
"No, Lucifer." Sam answered, before any question could even be asked.
"Sam," the devil's voice sounded so much like the angel he used to be. "I've told you. I'm not going to hurt you. I want to give you everything. Try me. Ask for anything, right now."
Sam shook his head in disbelief, shoving his hands through his hair nervously, before barking out a shaky laugh. "Really? Anything?"
"Anything." Lucifer promised.
"Fine," Sam snapped. "Bring Jess back. Go back in time and stop her from burning on the ceiling."
"That's all?" Lucifer made a face, then snapped his fingers. "Fine. Done."
Sam blinked in confusion. "What do you mean, done? Where is she?"
Lucifer looked at his wrist, even though he wasn't wearing a watch. "At this hour? Probably at home in bed, with her husband."
"No." Sam shook his head, his frown deepening. "If she was alive, I would be her husband. I was going to ask her to marry me."
"And you did." Lucifer nodded. "But she said no. She was rather upset after your road trip with Dean. Can you blame her, really? You had given everyone the impression Dean was dead. And then there was the matter of her doing a little poking aorund the apartment while you were gone, and finding your guns and knives. She was a little freaked out, your Jess. She confronted you when you came back, and you told her the truth. You told her about hunting. She realized two very important things. First of all, that you wouldn't have told her, if she hadn't practically threatened to walk out on the spot. And secondly, that she was in danger by staying with you. She moved out later that week."
"What?" Sam barked out a sound that was a combination of disbelief and anger.
"You really thought if Jess wasn't dead, she would be married to you, and you wouldn't be hunting?" Lucifer arched an eyebrow. "You thought you'd have a law degree and an SUV and a house in the suburbs that looks like all the other houses?" He shook his head. "You really thought it was that simple?"
"Yeah," Sam huffs defensively.
"Oh no," Lucifer spread his hands wide. "This timeline is so much more bloody. Are you sure you want to hear this?" He continued, not waiting for an answer he's not likely to get anyway. "You made it back in time for your interview and you got the full ride for law school. Dean went on looking for your dad without you, always one step behind him. Then Azazel sent a demon for your dad to catch and torture for info, who let it 'slip'" Lucifer made air quotes. "that Ol' Yellow Eyes was coming, not for your dad, but for his son. He, Caleb, and Pastor Jim all showed up that night to protect you. He really didn't think they meant Dean, but your dad sent him to Bobby, just in case."
Lucifer paused and looked significantly at Sam.
"Adam." the young man whispered.
"See?" Lucifer grinned, pointing a finger at Sam. "You're smarter than your old man. Poor Kate Milligan burned on the ceiling while Adam watched. And Bobby too, while Dean watched."
Sam involuntarily straightened at the news.
"It was crude, but incredibly effective." Lucifer shrugged. "Turned poor Adam against his father completely. He's thrown his hat in with the angels. Zachariah didn't even have to try to sell him. And you," Lucifer smiled fondly. "You threw away law school. You went back on the road with Dean. You wanted to help him avenge Bobby, but you also recognized that he was so damaged by seeing the Bobby-que that he was probably going to get himself killed, or drink himself to death in a motel room in Arkansas like your dad did." Lucifer took a few steps before turning back to Sam. "So bottom line. You're a hunter. You're not with Jess. John Winchester is dead. You've been on the road with your brother, the Post Traumatic Stress Disorder poster child. The two of you have now parted ways, and it's time for you to step up and be who you were meant to be all along. My true vessel, Sam."
Sam shook his head and murmured "No."
"That's the thing." Lucifer gestured vaguely. "We always end up ... here. Whatever you do, you will always end up here. No matter what choices you make, whatever details you alter, we will always end up ... here."
"The answer is still no." Sam folded his arms.
"And I'll be back." Lucifer smiled sadly before disappearing with a flap of wings.