The Red Caboose
By Tidia, August 2007
Supernatural belongs to Kripke. The Brotherhood was created by Ridley
A/N: I would
suggest reading Black
Bras & Strappy High Heeled Shoes
because the title of this fic comes from that one, and now it is Sam's
turn to have his first time.
Sam sighed loudly,
again. After the second time, Dean had turned up the volume on the
radio, but still he heard the most recent one. He had been expecting it.
"I'm driving as fast as I can, Sam," Dean said, with patience beyond
his 21 years. If his brother were normal, then he'd want to go to the
nearest bar, use the fake ID that said he was of age, and drink.
But was Saturday night and Sam wanted to go home and study for a test.
"It's important," Sam whined, "I'm not getting anything done this way."
An open chemistry book rested on one knee and a notebook lay across the
other. He held a flashlight in one hand and a pen in the other.
Dean had tried to quiz him, remembering as much as he could about high
school chemistry while concentrating on the demise of the Assante's
poltergeist. Sam hadn't appreciated his efforts. Was it his fault he
found stoichiometry easy?
"You need to relax, man. You're going to do fine." Dean shifted in the
driver seat, glancing up at the green interstate sign: Soso,
Mississippi, 60 miles. He hadn't realized they were so close. Dean
glanced over at his brother with a smile. The proximity to Soso
provided an opportunity that was time to take. He pulled out his
cellphone and Sam released another exasperated sigh at the sound of the
"Damien, where you at?" Dean asked before the older hunter uttered
little more than a greeting.
"Hey, haven't heard from you in awhile too," Caleb replied with
annoyance. "I'm in Alabama."
Dean nodded. Perfect timing, it was a sign. "I'm in Mississippi. An
hour away from the Red Caboose, in fact."
Caleb laughed, knowing exactly what was going to happen tonight. They
were building memories. "It's about time, Deuce. I can be there in two
"Hell, yeah." Dean shook his head as he noticed his brother bending his
lanky frame over the book, trying to absorb the words by being closer
"Don’t forget to give him the speech," Caleb reminded Dean.
Dean smiled. He had been fifteen his first time at the Red Caboose
after Caleb's strappy high heeled shoes and black bra speech. That
information still held true. "See you soon."
"Where are we going?" Sam sounded exactly like their father at that
The older Winchester mimicked the same tone. "I think it's time you
played in the big leagues, Sam."
Sam tapped his pen nervously against the book. "What are you talking
Dean sighed. "A man has needs, Sammy, and sometimes those needs can't
be satisfied by some old issues of Playboy, Hustler and Penthouse."
Dean was aware of his younger brother's stash. He had, in fact, given
him most of the magazines. "Bro, you need to get laid."
"I am? What? No." The book, notebook, pen and flashlight fell to the
floorboard. The beam of light caught Sam's scared face.
Dean was amused by his brother's reaction and, in true sibling form,
laughed. "You saving yourself for marriage? Please don’t tell me you
believe Pastor Jim?"
"No, I mean, Dean. . ." Sam stuttered, turning red. He glanced down at
the flashlight, snatched it up and turned it off to save himself any
"This is my job as big brother, unless you want Dad to take you— ‘cause
that's never going to happen." Dean snorted. John Winchester rathered
his sons not get involved with women or fun in general.
"Dad? God. No." Sam shook his head, his hair falling into his face, he
pushed it away.
"That's what I thought." Dean reached out and squeezed his brother's
shoulder, then gestured to the dashboard. "Open the glove box. You're
going to need them."
Sam was flappable. Dean watched as his brother picked up a condom by
"Dean, I don't . . ."
Although Dean shouldn’t enjoy his brother's discomfiture, he did. There
were too few opportunities with Sam without him being sullen or their
father intervening. "Take three."
Sam heeded the advice and took a few more condoms, stuffing them into
"I am going to give you some advice. . ." And Dean passed along what
Caleb had told him when he was fifteen and in the parking lot of the
"You’re telling me it’s about clothing? Shoes and a bra? What about
paying attention to what she says?" Sam scoffed.
Caleb would be unhappy to learn that Sam had dismissed his counsel.
"Not important." Dean frowned. The youngest Winchester was analyzing
casual sex to the point where he would remain a virgin forever. "We're
talking about a one night stand here, Sammy, not the future Mrs. Sam
Sam nodded. What surprised Dean was that Sam wasn't protesting, at
least not too much.
"I should really be studying." Sam picked up the discarded books and
"It'll be an hour before we get there. Study up."
The flashlight flickered on once more, the books were placed back in
position, but Dean noticed the page never moved.
They pulled into the Red Caboose and Dean grinned. Not much had
changed, except there were a few more cars in the lot because it was
the weekend. Sam got out of the Impala and wiped his hands on his jeans.
"Don't forget to use the ID." Dean reminded his brother as he corralled
him towards the door. Sam's false identification wasn't checked and
Dean pointed to a table in the corner for Sam to take while he got a
pitcher of beer.
He returned, balancing the pitcher and two mugs. Sam was slouched at
the table trying to minimize his height. The teen exuded gawkiness.
"Dude, straighten up, and look happy," Dean mumbled, and pushed the
pitcher towards his brother. Dean scanned the room, catching the eye of
a brunette who gave him a come hither smile before looking away. She
was with another girl who was attractive and, Dean was pleased to see,
wearing strappy high heeled shoes that tied around her ankles. Perfect.
"Stay here. Be alert. Caleb should be here soon. I'm going to do some
recon." Sam gave his brother a nod and returned to the beer.
Caleb slipped in the door of the Red Caboose. He took in the ambience.
The same uneven pine floor, old jukebox, scarred bar and picture of a
tractor on the wall. The music had moved up a decade, but was still a
decade behind. Dean was talking to two women, and he gave the younger
hunter a nod. Caleb found Sam in the corner with an empty pitcher of
He lifted a hand and caught the bartender's attention. "Tequila." He
put two fingers for two shots. Caleb slipped into the seat across from
Sam. "Heard tonight was the big night."
"Shut up." Sam groused.
The kid was evidently nervous. A waitress slipped the shots on the
table with a smile for Caleb. "This is a happy place." Reaves sighed.
"It's a crummy bar, not Disney World, Caleb." Sam fingered the top of
the shot glass.
"But it is." Reaves knocked back the shot and let it settle for a
moment before explaining his answer. "I took your brother here when he
"Fifteen? Does Dad know?" Sam's eyes grew wide.
"It's not like we had his blessing, Runt." Caleb put his hands up in a
calming gesture. Sam was wired. "I got us two rooms at the General Lee
Motel. Under the names Truckee and Likely."
Sam rolled his eyes. "You are so weird."
"You guys pick rock stars and I pick strange city names." It helped him
with geography and getting around the country. His method was at least
useful. "Who's weirder?"
"What state?" Sam asked as he rubbed the back of his neck.
"This week is California." It was a big state with lots of strange town
names. Caleb gestured with his chin. Sam turned around to see Dean
returning to the table.
The older Winchester took the empty seat next to his brother. He lifted
his fist to Caleb, who tapped it with his own fist in greeting. "So
were you a good wingman?" asked Caleb.
"Dude, I'm Maverick, not Goose. Heather has a sister." Dean turned
around and grinned at the smiling blonde. He waved at the brunette,
then turned back and rubbed his brother's hair. "And she wants you."
"What? Dean, what did you say?" Sam blushed.
"Drink." Dean pushed the shot towards his brother.
Sam took the drink and Caleb watched the younger hunter pale. "You
aren't going to throw up are you?"
"Shut up," Dean answered and lifted his brother to his feet. "He's a
Winchester." Dean gave Sam a slight push forward. "Just go over there,
and have fun."
"Guess he's not going to be our little boy forever," Caleb commented as
Sam made his way towards the brunette. The blonde, her sister, excused
herself and gestured to Dean that she was heading towards the bathroom.
Dean and Caleb watched the twosome. She would bob her head and Sam
would nod. "He's talking to her." Dean groaned and placed his head on
"Not everyone goes in for the kill. Let him find his own way." Caleb
smiled. "Plus I'll send over a few rounds of drinks to keep things
"Dude, he has to be able to perform." Dean lifted his head. "He's over
17. It was time. Right?"
Reaves nodded. "You did good, Deuce. You know your brother is a late
bloomer. Who knows what would have happened? He may have actually taken
Pastor Jim's advice."
"He thought your speech sucked." Dean rested back in the chair.
"My speech does not suck." Caleb was not surprised, Sam was a thinker.
He liked to analyze a situation. "Did wonders for you."
"That it did." Dean raised his eyebrows up and down. "You going home
"Not likely… with Miss Lisa." He turned to face a curly haired brunette
at the bar, who was teasing a straw with her mouth. She met his glance.
"What she wants to do to me. . . ."
"Isn't that using your powers for evil?"
Pastor Jim was always pressing the issue of being responsible, and how
his abilities were a good thing. But, responsibility had to be
tempered, and sometimes used to benefit oneself. "I was evidently
blessed with these abilities, might as well benefit from them, and my
classic good looks don’t hurt either."
Dean laid his hands down flat on the table. "You got style, Damien;
I'll say that about you."
Heather and Lisa helped pass the time for the two hunters. Dean kept
glancing back to check on his brother. Things finally progressed when
Heather's sister, Amanda, grabbed Sam by the hand and led him out the
door. Reaves caught the other hunter's attention.
"I'll catch up with you guys later," Sam said as he passed by the
table. His arm was looped over Amanda's shoulder and Caleb didn't know
if the girl was supporting most of the youngest Winchester's lanky
"Okay, Sammy." Dean lifted his glass in salute.
Sam dreamily headed down the hallway of the General Lee Motel after an
early morning breakfast. Amanda had dropped him off with a lingering
kiss. He could still taste a hint of strawberry gloss as he knocked on
one of the hotel rooms There was no answer, instead the door of the
neighboring room opened. Dean popped his head out and studied his
brother with a grin.
"We were getting worried."
Sam confidently strode into the room, holding a cage by his side. Caleb
sat on one of the beds, a Styrofoam container sat to one side.
"So-" Caleb pointed to the cage. "What've you got there?"
"A hamster." Sam grinned, lifted the cage and poked a finger through
the cage. The animal responded with a squeak. "I bought it. His name is
"You bought it?" Dean studied the hamster, then his brother, returned
his gaze to the hamster, then finally sat down next to Caleb. "Before
or after. . .Tell me you didn't. . ."
Dean and Caleb's eyes were wide, staring at him. He looked at Pedro,
and his mouth dropped open, stunned. Truly, he wondered about the
guttural thoughts of the older hunters. "God! No. No!"
Dean was relieved, but speechless. He waved his arm in front of Reaves.
"I think what your brother is trying to ask is - how your first time
leads to a parting gift of a rodent?"
Sam rested Pedro’s cage on the television, careful to make sure it
wouldn’t tip over. It seemed sturdy enough. "Don’t know why the lady
sold it to me. Really, I was in no condition to take care of an
animal." He kept one hand resting on the cage.
"Drunk hamster buying?" Dean said, his voice rising.
"Right. At an all night pet store." Sam nodded eagerly. He had always
wanted a pet, and it seemed like a good idea and a perfect opportunity
at the time. "Amanda said she really liked hamsters. We were walking
back to Heather's place, and I saw this pet store…"
Caleb was laughing a ‘hands resting on knees, bent over trying hard to
take in a deep breath’ kind of laugh.
"Stop laughing, Damien." Dean shoved Reaves's shoulder. "This is
embarrassing. Please tell me you did the deed, please?"
Sam was not going to confirm what had happened last night. Sam had
decided to be different from Dean and Caleb and not speak about his
conquests. He respected Amanda. He looked at the other hunters and
shrugged his shoulders. It wasn't embarrassing at all. Everything was
as it should be. "Amanda likes hamsters. She suggested the name." Sam
happily went along with it, in fact , he’d gone along with everything
Dean stood up. "It's not coming into the Impala."
"I can’t believe you named it." Caleb was still trying to control his
laughing fits. "Deuce, I told you that you should have allowed Sammy a
pet growing up. . ."
"If Amanda likes hamsters, we'll drop it off then." Dean ignored his
friend, picked up the cage and placed it in Sam's hands.
"I can do it," Sam volunteered, "while you two pack up." Dropping off
Pedro would probably lead to something else, and Sam didn't want his
brother waiting outside.
"You sure, what about that test on Monday?"
Sam had forgotten about the chemistry test. "I'll cram on the ride
Dean stepped back and appraised his brother. He tossed the Impala's
keys at Sam. "Make it quick. Take what you need from the glove box, but
after this you buy your own."
Sam didn't turn around. He opened the door, but could still hear Caleb
through the door.
"Dude, I am so putting this in my hunter's journal so that future
generations can be awed by Sam Winchester."
"Awed is right. He invented a new drunken activity—hamster buying, go
Sam lifted the cage so the hamster was at eye level. "Maybe we should
have named you Lucky."
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