A/N set after season 3 with references through early season 5. This started with the images of Sam's summer in I Know What You Did Last Summer and the old song about Alice in Wonderland by Jefferson Airplane

How did Sam fall down the rabbit hole of addiction?

Disclaimer: White Rabbit – belongs to Jefferson Airplane and Supernatural to Kripke and TPTB

SPSPSPSPSP

One pill makes you larger
And one pill makes you small
And the ones that mother gives you
Don't do anything at all

Sam tipped the bottle back further taking another drink then hung his head.

How many days had it been since he had lost Dean? He tried unsuccessfully to make a crossroads deal for Dean. Then gone back to Bobby's, he couldn't remember those first few days at Bobby's after Dean's loss it was a blur. He'd researched everything he could think of till Bobby had made that comment.

"Boy, I'm glad you're smarter than Dean, because otherwise I'd be worrying about you making a deal with demons."

Sam still wasn't sure what gave him away, but something had because the next thing he knew Bobby had been in his face saying, "You are not seriously thinking about trying a stupid stunt like that are you, is that what your research has been about? Well has it?" Bobby had demanded.

Go ask Alice
When she's ten feet tall.

"Nope, cause it didn't work, I gotta find something else." had been his reply.

Bobby had been livid, "Not with my help you won't you stupid son of a bitch. Dean is gone. He ain't coming back. Do you think Dean would have wanted this for you? No, he'd want you to carry on hunting. Carry on the job, here take this and go!"

"What is it?"

"A hunt Ellen caught wind of. Now, go on git, git out of here, and git to work doing something useful. You stupid Winchester."

So Sam had left. He taken the directions and hunted down that ghost. Then hunted down what turned out to be a werewolf. Unfortunately that brought back memories of Madison and only made things worse.

And if you go chasing rabbits
And you know you're going to fall,

Hunting wasn't really helping except when he actually killed something otherwise the only relief from the pain was at the bottom of a bottle.

That was until he'd drunkenly stumbled back to his room one night to find Ruby and another demon waiting for him.

"Thanks for keeping this warm for me Sam" she'd said as she took the knife from him.

He struggled a few moments in vain but the other demon had him held tightly. Ruby had mentioned Lillith and that she was back to kill Sam. Something in Sam had snapped then and he had baited her to kill him. She'd had other plans, lucky for him or maybe not so lucky. Ruby had killed her demon partner and then insisted that they flee.

When she mentioned food then talked about escaping hell wanting his thanks for helping him it was the last straw. Sam had asked if she could help save Dean and when she'd said no he'd pulled the Impala to the side of the road pointing out that he had no use for her and told her to get out. He'd pointed out that she was riding someone's body and that he now cared what that meant. He'd then told he to let her host go or he'd send her back to hell himself.

Tell 'em a hookah smoking caterpillar
Has given you the call.
Call Alice
When she was just small.

Sam had thought that was the end of it. Ruby was more creative than he'd imagined though, so after snatching the body of a coma patient she had once again tracked Sam down. Sam had no real purpose left other than hunting. Dean was gone. Bobby had shut him out. So, why not listen to her proposal besides which if he didn't like it he could always just kill her.

She still couldn't help with Dean, but she did offer to help him with revenge against Lillith and to stop Lillith's latest plan which she said was big, apocalyptic big, even if she said she couldn't tell him what it was exactly.

When the men on the chessboard
Get up and tell you where to go

And what did she want him to do, use his psychic stuff, so he'd started to learn to pull demon by thought alone. It didn't much matter the method by which he could succeed at killing Lillith after all who was left to care with Dean gone. Avenging Dean gave him a goal, besides he was saving people just like Dean would have wanted even if he might not have approved of the method. He had no plans for anything beyond destroying Lillith, it would make a fitting end to take of a piece of business his brother had left behind.

Sam had to stand basically on his own now with only Ruby for help. After one failed attempt, Ruby had wound up killing the demon with the knife. Sam had come back in from burying the body and taken more pain killers for his headache and was chasing them with liquor when Ruby started in on giving it time. At first he'd though she only meant pulling demons but she was talking about Dean and that hurt more than his head. When he confronted her about that, about how time heals, she gave him a story of how she remembered being human and all that came with. The next thing he remembered was her pitying him, telling him he wasn't alone, and then kissing him.

Part of Sam had reacted instantly to that kiss, it had been so long since there had been in pleasure in his life even the fleeting kind offered by sex. Sam had tried to stop it then, walking away and trying to defend why it was wrong. Ruby had followed with teasing words and worse tempting actions. Sam had been overwhelmed rapidly and given in seeking comfort in the temporary pleasure and oblivion that sex could provide. He knew it was wrong but was it really very important it was temporary and it felt good. In the aftermath of their spent passions, he relaxed. He was able to wonder that somehow he wasn't quite so totally alone and empty anymore that for a moment at least the gaping hole left by his brother's loss wasn't quite so overwhelming.

It wasn't long after that Sam had put together some signs that Lillith was in town. Ruby tried to convince him he wasn't ready, but Sam was tired of waiting and he had found a purpose. His one purpose was to take revenge on Lillith for Dean's loss. Ruby realized that Sam had no intention of surviving and had once again tried to stop him on his way out. She'd tried to say Dean would not want this for him but he'd gone anyway.

He almost hadn't survived. He'd gone straight into a trap, a trap that could have killed him without him getting Lillith. Ruby had saved him. After he'd saved the girl he'd come back and saved Ruby or at least it appeared that way. Saving someone had felt good and he'd also managed to pull a demon properly. Ruby had seemed grateful and shown it. She'd also given him something to help with the headache that was the worst he'd ever had. She'd also pointed out how good it had felt to finally save someone again and take out the bad guys. "That saving people, hunting things, that is what Dean would want you to be doing Sam. Not wasting your time grieving for him and definitely not wasting the life he gave his soul to save. She'd given him what he needed to hear and then more solace and comfort. After a while she'd pointed out, he's gone so now you have to finish the job, but not alone. I'm here to help you. With that bit of comfort he could struggle on long enough to kill Lillith. All his energy and focus centered as it became his overwhelming goal his soul purpose for existence."

Together they'd started hunting demons. Ruby was better at locating demon possessed people than he and Dean had ever been. Usually Sam was able to save the host and what she gave him helped with the headaches, better yet after the first few times she'd given it to him beforehand. Sam had been thrilled because from then on he'd had less headaches.

Yeah he was thrilled until he found out just what it was. He'd been stunned to walk out of the bathroom and head toward the kitchenette just before a hunt to see Ruby bleeding into a cup.

And you've just had some kind of mushroom
And your mind is moving low.
Go ask Alice
I think she'll know.

Sam had gone that hunt without, the headache afterwards had been horrendous and the pain killers and alcohol had barely touched it. Worse the crushing pain of Dean's loss seemed to be back ten fold. Sam had no energy and no appetite. Two days later a fever had hit, he'd tried to fight it but been too weak. Somewhere in the middle of his hallucinations, she had offered herself. He had taken the offer though he barely remember taking over, taking her and her blood. In fact he might not even have believed her, except he woke up the next morning feeling fine and she had a bit mark on her neck.

When logic and proportion
Have fallen sloppy dead,

As he tried repeatedly to apologize, she reassured him that it was OK. That she was fine in fact she had enjoyed it. What she really wanted was for him to be at his best because he was the only one who could take out the demons now and eventually Lillith. Stopping Lillith was what was most important. That was the ultimate goal. It needed doing by any means necessary. She assured him her blood was minor in the scheme of things, that if it gave him the strength to go on then that was all that mattered. She would help him and together they could destroy Lillith because she could give him the strength he needed to get the job done.

And the White Knight is talking backwards
And the Red Queen's "off with her head!"

Not until much later would he realize how dependent he'd become to the blood and the strength Ruby gave him.

Only in Ruby's boasting after Lillith's destruction would Sam realize how thoroughly he'd been manipulated as Lucifer broke free because he, Sam, had broken the final seal in his arrogance and thirst for revenge

Remember what the dormouse said:
"Feed your head. Feed your head. Feed your head"

Worse yet and only when it was much too late for anything but regrets would he realize what his addiction and Ruby had truly cost him, his brother's trust.

SPSPSPSPSP

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I welcome feed back on this as a possible scenario, as I said the song helped me wonder how someone essential good becomes addicted but especially something so obviously wrong.