In this story, I envisioned Ruby as coming back as a man. I thought Ruby as a guy would be a greater mind**** on Sam, as you will read in the story.
If you are expecting some man-to-man action, you will have to look elsewhere. I took snippets from the show, and inserted some of my own dialogue. I borrowed from another fan fiction author, who wrote the story "Amanda Kelps." To the original author, I hope you do not mind.
Dean looked at Bobby hesitatingly. Should he knock? How would Sam take it, seeing Dean alive? If it was Dean, he would break out the Colt and shoot the bastard impersonating his brother square between the eyes. Maybe Sam was doing all right for himself. Perhaps he founds some pretty girl to spend the night with.
He looked again at Bobby, and received the paternal eyes: knock on the damn door, boy. Dean pounded on the door.
Both men were surprised to see a good-looking man standing in front of them. Is that the blond guy from Four Brothers? Dean asked himself.
The man leaned forward.
"So where is it?" asked the guy in the room. Dean and Bobby looked at each other dumbfounded.
"Where's what?" asked Dean.
"The pizza that takes two guys to deliver," said the guy sarcastically. He leaned against the door nonchalantly. Dean studied him. The guy looked like a rock star.
"I think we got the wrong room," said Dean.
"Hey is…" said Sam, as he walked into the room. Dean's and Sam's eyes connected. Sam searched the outline of Dean's face. Dean felt joy inside. He instinctively smiled—the happiest that he'd been in a long time.
"Hey Sammy," said Dean. I found you, little brother. Dean walked towards his brother, ready to embrace him. That was when Sam broke out Ruby's knife and tried to stab him.
"Whoa!" exclaimed the Rock Star.
For a moment, all hell broke loose. Finally, Sam realized that Dean was truly Dean—thanks to Bobby's coaxing. Dean got the hug that he was waiting for.
"Hey, Sam, this is a little…disturbing. I'll catch you another night."
"Right," said Sam, embarrassed.
The brothers were left to interact.
Dean couldn't believe his ears.
"So Ruby is…was…the guy from the hotel room?" asked Dean.
"Yeah," said Sam.
"Oh," said Dean, with his eyes squinted in confusion.
"Who was really pissed because I took the knife back."
Eventually, Sam explained to Dean how Ruby first appeared to him. She looked similar to how they last remembered her—blonde, beautiful, badass. With another demon holding him, Sam was sure that Ruby was going to kill him. She removed the knife from his person. Without hesitation, she…plunged the knife into the other demon. Both relieved and shell-shocked, Sam dashed out with Ruby. Run first, get the explanation later, thought Sam.
Ruby explained her motives: she gained Lilith's trust by promising to eliminate Sam. Despite the details that Ruby was giving him, Sam managed to stay rational about one thing: Ruby was invading another human. After demanding that she use somebody else, Ruby left her "meat suit." Sam had the awkward task of explaining to the young secretary that she passed out, and that he was taking her to a hospital. Luckily, Ruby's possession of her was short. The woman had no memory of Ruby. It did not go as well for the last "meat suit"—Amanda Kelps. She eventually checked into a psychiatric ward.
The next morning, Sam heard a knock on his door. He readied his shotgun, and opened the door cautiously. A young man stood in front of him. Is that Garrett Hedlund? thought Sam.
"Are you satisfied?" asked Ruby.
"Do I know you?" asked Sam, the impatience evident in his voice.
"I figured this would happen," said Ruby, "Let me in."
"Wait, I don't know who the hell you are," said Sam—displaying his shotgun.
"Look…you told me to find another body, and I did. A brain-dead John Doe was in the ICU. When nobody was looking, I jumped into his body," said Ruby, "I've never had to be so discrete."
"Ruby?" asked Sam. He could not hide his shock and disgust.
"So, is this going to be a permanent thing?" asked Sam. He hoped it was just a bad dream…or a vision-altering hangover.
Ruby stormed passed Sam. Okay, so it's not a hallucinatory hangover.
"I don't know. Hopefully, you can snuff Lilith soon so I can have a vagina again," said Ruby sarcastically.
Sam shook his head as he closed the door behind him. It's really happening, all right.
"So I have officially recycled bodies—to Al Gore's liking, I'm sure" said Ruby, "Beggars can't be choosers, though. Look at these track marks!"
Ruby raised up his sleeve.
"Anyhow, your days of being a depressed lump are over. We've got work to do."
"What are you talking about, Ruby?" asked Sam, feeling his temples pounding. He massaged his headache.
"You heard me name you know who. First thing…you need to lay off the Jack Daniels. If that's too much to ask, at least open a window. The AA would get drunk by the fumes."
Ruby fanned the air.
"All right, enough Ruby!" yelled Sam, "You just show up out of the blue, claiming to have tricked Lilith, and you want what out of me?"
"Nothing's changed. The objective is still the same, short bus…kill Lilith," stated Ruby, matter-of-factly.
Sam chuckled a little. "Short bus…I'm still taller than you, you know," said Sam, pushing the hair out of his eyes.
"You tower over everyone. No worries, though. I still like a tall man," said Ruby. He cocked his head to the side, and crossed his arms.
"Okay…please stop…that is really creepy," said Sam. Shivers were running up his spine.
"If it makes you feel better, I can find another meat suit," said Ruby.
Sam stayed silent for a moment.
"You're telling the truth about the John Doe, right?" asked Sam.
"Cross my heart," said Ruby.
Sam sighed—defeated.
"I'm listening," said Sam, as he tossed his bottle of Jack Daniels in the wastebasket. No matter how drunk he was, Sam couldn't get over Ruby's gender bender.
"I can't bring Dean back," said Ruby.
Sam flinched at Dean's name.
"But I can at least offer you Lilith," said Ruby.
Sam snorted. Here we go again, thought Sam, more head games from Ruby.
"From our previous encounter with Lilith, it's evident that witchcraft and brawn won't do," said Ruby. "So…."
"You want me to use my psychic whatever," said Sam.
"Yes," said Ruby. His eyes were eerily piercing.
An awkward pause.
"I'm ready," said Sam, "Let's go."
"Good," said Ruby. He took a seat, with his legs crossed like Sharon Stone. "Because Lilith is one scary bitch. When I was in the pit, there was talk. She's cooking up something big…'apocalyptic big' big."
"So, let's kill her," snarled Sam.
"That's right…the Winchester cowboy attitude. Did you forget about that night?" asked Ruby. Ruby cocked his head, and pushed the bangs out of his eyes.
Sam smirked at the question.
"We have the time to get it right. There's no room for you going in half-assed…not like before," said Ruby, giving a trademark fake smile.
The words stung Sam's pride. "Okay," said Sam, "What do you want from me?"
"Patience…sobriety…you know, everything that makes a perfect student," said Ruby, crossing his arms again, "Promise me that, and I will teach you everything I know."
Sam kicked away angrily at the pentagram.
"Give it time, Sam. It will get better," said Ruby soothingly. Even though Ruby had his arms crossed, his body language was non-judgmental.
Sam snorted. He downed some aspirin with whiskey. His first violation of the agreement.
"What…I just need practice?" asked Sam.
"I'm not talking about pulling demons," said Ruby, "I know losing Dean was…"
"Hey…I don't want to talk about it," said Sam, dangerously pointing his finger. "You know what…where do you get off slapping me with that greeting card "time heals" crap. What do you know?"
"Because I still remember what it's like to be human," Ruby fired back, "And I sure as hell know what it feels like to lose someone."
Ruby looked away from Sam.
"I'm sorry," said Ruby, almost in a whisper.
"Sorry…sorry for what?" asked Sam.
"I relive that night constantly, and I feel like I failed the both of you."
"No, uh-uh," said Sam, "Don't play that card."
"You're not alone in this," said Ruby.
"Ruby…just shut up," said Sam.
Ruby gave Sam a right-hook. Blood dripped from Sam's lower lip.
"Come on!" yelled Ruby, putting his fists in the air.
Sam leered at Ruby.
"I'm not a petite blonde anymore," taunted Ruby, "You don't have to hold back. You can beat the crap out of me now."
Ruby gave Sam a left-hook. That time, Sam stood up.
"He isn't here, anymore, Sammy," said Ruby, digging his finger into Sam's chest. "You can't cry to your big brother anymore."
Upon hearing Sammy, Sam was reminded of Dean.
"I told you to shut up," snarled Sam.
"Come on, Sammy, break out the knife. That's how you want it, right?"
Sam charged Ruby. The fight went back and forth. A head butt from Ruby, a choke-hold from Sam, a round kick from Ruby. Then, Sam gained the upper-hand, and positioned the knife over Ruby's heart.
"Is that how you want it, Sam? I crawled back from Hell…so I could help you," said Ruby, holding back Sam's hand. Ruby's words touched Sam. Hell…the same place that Dean was rotting in. Sam dropped the knife.
He sat away from Ruby. Ruby collected himself.
"Now that we got that out of the way…are we supposed to have a round of beers?" asked Ruby.
Sam looked at him puzzled.
"I'm still new at this guy thing…so help me out," said Ruby.
Sam filled both shot glasses with Jack Daniels.
"Honestly, I'm surprised I beat you," said Sam, nursing his busted lip, "Haven't you been around since medieval times?"
"What…you mean like the Middle Ages?" said Ruby, incredulously, as he held the ice pack to his right eye. "No, the Plague hit my neighborhood in the 1920s."
"Wait, the Plague mutated into cholera," said Sam, "So, you were around during a cholera outbreak."
"My village was backwards," said Ruby, nursing his black eye, "Plague… cholera…nobody cared about the name. All people needed to know was that the sickness was spreading, and nobody was getting out alive."
"So, is that when you became a demon?" asked Sam.
"My family was dead," said Ruby, mournfully, "Giving away my soul seemed like a good idea at the time. I was poor and had no means of escape. I was just a good old country girl with a knack for spells."
"Then Dean…" said Sam.
"…Was just thinking like everybody else," said Ruby, "I mean, come on, you hear plague and you think The Plague."
"What did you do…afterwards?" asked Sam.
"I went to New York, and learned English from flappers," said Ruby, "Not the best introduction to syntax and grammar."
Sam laughed. Ruby smiled. They both took their shots. For a moment, Sam felt like he was with Dean again.
Sam conversed with Ruby about the angel situation. Despite Ruby now being a man, Sam was overprotective. Ruby's meat suit looked younger than Sam. As much as he hated to admit it, Ruby looked and acted like the younger brother Sam never had. Most importantly, Sam didn't want to lose Ruby. Who else was willing to help Sam?
"Watch yourself, Sam," stated Ruby, emphatically.
"I'm not scared of angels," said Sam, defiantly.
Ruby seemed about to say something, but stopped himself. Instead, he walked away.
"I'm about to violate your comfort level," said Ruby.
"Mission accomplished," said Sam, putting his hands out like a magician towards Ruby's body.
"We need to up the ante," said Ruby. He grabbed a kitchen knife, and sliced his wrist. Ruby drained the blood into a bowl.
"What are you doing?" asked Sam. He stood up from his seat.
"You want to get powerful enough to kill Lilith?" asked Ruby, "Start drinking." He pushed the bowl to Sam.
Sam stared at Ruby's wound. Dean was already gone. What else did he have to lose?
Dean looked in his rearview mirror. Anna and Ruby were in the backseat.
"What?" asked Ruby, as he made eye contact with Dean.
"Nothing. It's just… an angel and a demon, riding in the back seat. It's like the setup for a bad joke. Or a Penthouse Forum letter," said Dean.
"Dude. Reality. Porn," said Sam.
"You call this reality?" asked Dean, increduously.
"You know, now that I'm a guy, I'm hung like Ron Jeremy," said Ruby.
Sam and Dean looked at each other uncomfortably.
"Who's Ron Jeremy again?" asked Anna.
"A healthy dose of reality, angel-pie," said Ruby.
Lilith remained lifeless on the floor. Sam had accomplished his final act of revenge.
"I can't believe it. You did it," as he said this, Ruby had his back turned to Sam.
"What? What did I do?" asked Sam.
"You opened the door," said Ruby, as he faced Sam. "And now he's free at last."
Ruby paced back and forth.
"I killed her!" exclaimed Sam.
"And it is written, that the first demon will be the last seal. And you busted her open, now guess who's coming to dinner," said Ruby.
"Oh my god," said Sam.
"Guess again," said Ruby, in a hushed tone.
"You tricked me?" asked Sam. The pain dropping with each syllable.
Ruby turned and looked directly at Sam.
"The fight ended in me, Sam," said Ruby, "I wanted to kill Lilith because I thought my deal would end."
Sam was transfixed at the blood pooling over the seal.
"But that wasn't to be," said Ruby. "It didn't matter one bit. I'm a demon and I will never get out of hell. We each have our destiny that we can't escape."
Sam tried to summon his demon extracting powers.
"That won't do any good, Sam," said Ruby, hopelessly. "I played my part well. Now, it's your turn."
Dean broke the door down. Ruby looked over his shoulder. Their eyes connected.
"It's too late, Dean," said Ruby.
"I can see," said Dean, looking down at the seal. It was erupting with light.
"I don't mean her," said Ruby, half-smiling.
Ruby didn't fight as Dean plunged the knife. His demon essence flickered. Ruby's mouth twisted in grotesque pain.
Sam watched as the body crashed to the ground. It was then that Sam realized that he never truly knew Ruby. Was Ruby the blonde firecracker that first sweeped into his life? Or the young man that filled the brotherly void in Dean's absence?
As Lucifer began rising from the seal, Sam thought If Ruby could give up so easily, what chance do I have?
Either way, Sam couldn't look at Dean.