Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/8293439.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Castiel, Dean_Winchester, Mary_Winchester, Jimmy_Novak
  Additional Tags:
      Underage_Sex, Oral_Sex, Older_Castiel, Underage_Dean, Blow_Jobs,
      Babysitting
  Series:
      Part 1 of The_Babysitter_Chronicles
  Stats:
      Published: 2016-10-16 Words: 2170
****** Straight to Hell ******
by crowleyhasfeels
Summary
     Dean gets asked to babysit for Castiel while he goes on a date. After
     Castiel's date goes wrong, Dean tries to show him how it was her
     loss.
Notes
     There is underage sexual activity in this. If this bugs you, please
     stop now!!
            Dean had known Castiel for a few years. He worked in the same
office as his mother and they had met at work functions and what not. Dean had
always liked looking at Castiel. He was awkward but in a crazy hot way. He had
the glasses, the sweaters and that hair that looked like he had just been
fucked. Nerdy was definitely a turn on for Dean. But Castiel was an older man
who worked with his mom, so he was very much off limits.
            “Hey, Dean?” Mary, Dean’s mother, had stuck her head through his
bedroom doorway a few nights ago. “How do you feel about making some extra
money?”
            Dean’s father had given him his old 1967 Chevy Impala about six
months ago, for his sixteenth birthday. It looked beautiful but the engine
needed some work. Since then, he had been working a job at his father’s shop,
as well as taking on any random jobs that he could. He wanted to make sure that
by the time he left for college, she would be in perfect working order.
            So here Dean was.
            Dean looked at the address on the slip of paper his mother had
given him and then back to the large house in front of him. He was not sure
what Castiel did at his mother’s company, but he definitely made more money
than her, unless his wife was loaded. Taking a deep breath, Dean lightly
pounded his fist against the door and waited.
            “Dean,” Castiel opened the door and gave Dean a smile that was all
teeth. Dean felt his heart flutter at the sight of it. Not just how he smiled
so wide but how he smiled with his entire face, his eyes crinkling up at the
sides. “So glad that you made it.”
            “Of course man,” Dean stepped in when Castiel gestured for him to
do so. “Anything to make a few extra bucks. Plus, kids are pretty cool.”
            “Jimmy is excited,” Castiel shut the door behind them and then lead
Dean further into the house. “His babysitter at his mother’s is a girl who
spends most of her time on the phone. He is hoping a boy will spend more time
with him. He has all of his video games ready to go. I hope you don’t mind? You
are not required to play video games.”
            “I am very open to playing video games,” Dean smiled. This was
going to be a piece of cake. If only all of his money could come this easily.
            Castiel spent the next twenty minutes showing Dean around the
house. He showed him the kitchen but then gave him thirty bucks to order a few
pizzas and some soda for dinner. He then gave him a small list of rules and
introduced him to Jimmy. Jimmy was the kid Dean was expecting. He was in love
with video games but very smart, definitely the kind of kid you would expect to
come from Castiel.
            “I will have my cell phone on me in case you need to reach me,”
Castiel lead Dean to a room toward the end of the hall. “I will probably not be
home until really late, so if you get tired, you can crash in the spare room.”
            “Sounds good to me,” Dean nodded. He then reassured Castiel that
everything would be fine and that he would call him if he needed him. Once he
was satisfied, Castiel left Dean to it.
            The rest of the night went by pretty easily. Dean had ordered pizza
and Jimmy beat his ass a million times over in Call of Duty. Normally Dean was
pretty good at games, but he had not played in a few years, so he was a little
rusty. He didn’t mind losing to the kid though, it just made Jimmy happy and
that was Dean’s job as a babysitter.
            Ten o’clock came and Dean decided that it would be okay to let
Jimmy stay up a little later than Castiel had informed him. It did not last
long though and by ten thirty, Jimmy was passed out on the couch. Dean let him
sleep for a while, making sure he was fully asleep, before moving him to his
bed for the night.
            Once Jimmy was in bed, Dean grabbed himself another soda and
settled in to watch some television. Three hundred channels and Dean was
watching an infomercial, but hey, he was getting paid to watch that
infomercial.
            “Dean,” Dean struggled to pull himself back to reality. It took him
a few moments to realize that he was being woken up. He had tried not to fall
asleep, but not everyone is successful all the time. “Hello, Dean.”
            Dean looked up at Castiel who was sitting down on the couch beside
him. He looked amazing but at the same time, something was off about it. Dean
looked a little harder and realized his eyes were red. Had Castiel been crying?
            “Everything okay man?” Dean asked, sitting himself up, wanting to
be supportive.
            “Oh yes,” Castiel avoided making eye contact with him. “I will be
fine Dean.”
            “You sure?” Dean reached out and placed his hand on Castiel’s
thigh. “You can talk to me if you like.”
            “I do not wish to burden you with my problems,” Castiel shook his
head at Dean but finally allowed for them to make eye contact.
            “I really would not mind,” Dean reassured him, again and again,
until Castiel finally broke down.
            “I went on a date this evening,” Castiel admitted to him. Dean had
never really asked what it was that he needed a babysitter for. “It did not go
very well.”
            “It was just a date man,” Dean tried to help but he was not very
good when it came to relationship stuff. He had told other people, including
parts of his family, about his interest in guys. However, it was hard in their
town to ever find a guy who was interested back. 
            “And I was horrible at it,” Castiel stood up from the couch. “I
have not been with anyone in three years. I finally ask someone out and she
gets bored.”
            “How do you know she was bored?” Dean asked seriously.
            “She spent most of her time checking her phone,” Castiel began to
pace the living room, obviously working off some of the alcohol in his system.
“It was like she was waiting for someone to send her a save message so she
could leave. Finally, I asked for a check.”
            “I am sorry man,” Dean rubbed his hands against his thighs, unsure
of what to say to this sexy man in front of him. He couldn’t just come out and
say how stupid this woman was for not being completely interested in this God
of a man.
            “She even elected to take a cab home,” Castiel continued, “couldn’t
spend one more minute with me, even if it was to just get home.”
            “Her fucking loss, dude,” Dean finally blurted out. “You are a
total catch.”
            “Thank you, Dean,” Castiel stopped and almost smiled, “but you do
not need to humor me.”
            “I am not humoring you,” Dean stood up and walked over to Castiel,
getting a little closer than he would have liked. He could smell the man in
front of him. He smelled the way old books did when you first opened them. Dean
had no idea that he liked that smell but it was breathtaking. “I would totally
let you drive me home.”
            Castiel did not speak after that. Dean worried that he had said
something wrong. Castiel was going to give him some ‘I am flattered’ speech and
then send Dean on his way.
            “Really?” Castiel finally spoke and Dean was taken back.
            “Really, really.” Dean smiled at the man in front of him and then
took another step toward him.
            “Thank you,” Castiel breathed out, only inches away from Dean now.
“I think you should probably …”
            Dean cut him off before he could finish his sentence; the one where
he was telling Dean to leave. Dean did not want to leave. He wanted to press
his lips against Castiel’s and that is exactly what he did.
            Dean expected Castiel to push him away, but instead, he pulled him
closer, wrapping his arms around Dean and holding him against his body. Dean
needed to pull back, he needed to breathe but he did not want to break apart
from Castiel. He feared that if their lips left one another’s, Castiel would
have time to worry about what a horrible idea this was. Castiel was a grown man
and Dean was only sixteen years old, he could not possibly want this.
            “Dean,” Castiel finally pulled his lips away but kept his arms
wrapped around Dean. “We should not do this.”
            “Why not?” Dean leaned in again and pressed his lips back against
Castiel’s, pushing his tongue forward until Castiel opened his mouth and let
Dean in.
            “There are so many reasons why we should stop,” Castiel pulled back
again to answer but not far enough to break contact.
            “Please,” Dean moaned into Castiel’s mouth. “I want to do this.”
            “But Dean,” Castiel continued to protest.
            “Just,” Dean pushed until the backs of Castiel’s legs were against
the couch. He then broke them apart and pushed Castiel down into a sitting
position. “At least let me blow you.”
            Castiel’s eyes got wide as he watched Dean drop to his knees in
front of him. He opened his mouth to say something but then closed it, giving
Dean the go ahead and do as he pleased. Dean smiled at this. He loved when he
got what he wanted.
            Dean worked his hands up Castiel’s legs and along his thighs. He
rubbed his hand against Castiel’s cock through his slacks, feeling just how
hard the older man was for him. Dean continued to rub it with the palm of his
hand. Castiel finally gave into his urges and leaned his head back, letting out
a deep gravely moan.
            “Oh god,” he cried out, just barely loud enough to hear.
            Dean took this as a good sign and continued forward. Finally, he
began to unbuckle his buckle and then unhook his slacks. Dean pulled at the
zipper and then pulled his boxers down slightly, leaving him fully clothed with
just his cock now out in the open. Dean spent a few moments taking in the site
of Castiel’s cock. It was about six inches long, a little longer than Dean’s
but thinner than Dean’s. Dean’s may not be the biggest in length but it was
definitely a hand full.
            “Amazing,” Dean whispered, hoping that Castiel had heard him but
also hoping that he didn’t. Dean did not need Castiel to know how nervous he
really was at this moment.
            Dean leaned forward, brushing the tip of his nose up the length of
Castiel’s cock until his mouth was at the tip. Pushing a kiss to the tip,
Castiel let out another moan, exciting Dean. Dean kissed it again and then
slowly slipped the tip into his mouth.
            Dean licked and sucked around the tip which was now dripping with
pre-cum, until Castiel began to buck his hips, begging for more with his body
and not his words. Dean was not going to deny him what he wanted and began to
take more and more of Castiel into his mouth until he could feel Castiel’s cock
in the back of his throat.
            Tears welled in Dean’s eyes as he pulled back and then took
Castiel’s entire cock into his mouth again, breathing through his nose.
            “Oh Dean,” Castiel cried out in his sex God voice as he grabbed the
back of Dean’s head. “Let me fuck that mouth of yours.”
            Dean looked up at Castiel’s blue eyes looking at him with so much
lust and Desire. Finally, Dean nodded, giving him the approval that he was
seeking. Soon, Castiel was bucking his hips up into Dean’s mouth while holding
firmly onto the back of his head. Over and over he pulled himself out and then
thrust his cock as far as he could down Dean’s throat without hurting him. Dean
moaned around his cock, encouraging him to continue.
            “Oh fuck,” Castiel cried out, letting go of Dean’s head and
gripping onto his shoulders. Dean reached out and grabbed Castiel’s hips,
taking over, bobbing his head up and down as Castiel came in his mouth.
            Dean groaned at the salty taste. There was too much of it to
swallow, though he tried. A small amount of cum breaking free from the sides of
his lips and dripping down his chin. He waited until Castiel’s body quit
jerking before pulling his mouth off of his cock and kissing the tip one more
time.
              “I am going to hell,” Castiel growled, pulling Dean up to him and
kissing him hard, then working to lick the cum off of Dean’s chin. “Straight to
                                                                         hell.”
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