Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/8919460.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester, Charlie_Bradbury/Gilda
  Character:
      Castiel, Dean_Winchester, Charlie_Bradbury
  Additional Tags:
      Underage_Sex, Oral_Sex, Public_Sex, Semi-Public_Sex, Older_Castiel,
      Younger_Dean
  Series:
      Part 3 of The_Babysitter_Chronicles
  Stats:
      Published: 2016-12-20 Words: 2691
****** Pie is Awesome ******
by crowleyhasfeels
Summary
     Dean feels that Castiel will get bored with him. He is just a
     teenager and has nothing to offer him. With some advice from his best
     friend Charlie, Dean comes up with a plan to keep Castiel interested.
            No one was more confused about what was taking place than Dean. He
had been having sexual encounters with his mom’s coworker and lying about it.
He had been pretending to be a babysitter when Castiel’s son was not around.
Part of him was enjoying this but another part was afraid. What would happen if
someone found out? He would not be in as much trouble as Castiel would.
Normally, that would not worry him but part of him really liked Castiel. Sure,
he didn’t know him that well, but there was something in terms of feelings that
Dean could not explain.
            I kind of like this secret we have going on. It is rather
thrilling, if I must say.Those words rang through Dean’s head over and over
again. Castiel had made it clear many times that he never felt more alive than
he had now that he was messing around with Dean. He called Dean a breath of
fresh air and a pure adrenaline rush. While Dean should be feeling used, he
actually felt pretty amazing.
            “Hey Charlie,” Dean leaned forward at the lunch table. Him and
Charlie generally sat alone at lunch but he did not want some random person to
hear the conversation that was about to take place.
            “Yes Dean?” Charlie leaned forward as well, pulling her eyebrows
together out of curiosity. If Charlie were straight, Dean would have hit on her
years ago. Though, another part of him was glad that she wasn’t or else he
could have ruined the best friendship he has ever had.
            “I need some personal advice,” Dean admitted. Normally he was the
one giving people advice but right now, he was at a complete loss.
            “Lay it on me,” Charlie’s face lite up. She loved giving people
advice. A lot of the time, she would give people advice, whether they asked for
it or not. It tended to be excellent advice though, so people never ended up
complaining.
            “I am going to tell you something first,” Dean took a drink of his
soda before continuing, still trying to work up the nerve to finally bring this
out somewhat into the open. “And you have to promise to not tell anyone.”
            “I would never,” Charlie began.
            “Not even Gilda,” Dean cut her off.
            Charlie made a face that said she was offended but then shrugged
her shoulders. He knew that she would keep his secret to the best of her
ability. Even if she promised not to tell Gilda, she was wrapped around that
woman’s finger. Gilda would not tell anyone, but still, it was not just Dean’s
secret and that made it bigger than it already was.
            “Fine,” Charlie huffed. “I won’t even tell Gilda.”
            “Okay.” Dean accepted that as ‘as good as it was going to get,’ and
relaxed a little. “I have been seeing someone.”
            “I figured,” Charlie nodded with a smile before biting into her
pizza.
            “You figured?” Dean questioned, though he should have known that
she knew something was going on with him. She always knew things in his life,
sometimes before he even figured them out.
            “You have been super smile guy lately,” Charlie informed him.
“Figured it had to be some babe putting out or something.”
            “Or something,” Dean looked down at his lunch to avoid eye contact.
            “I wish I could say I know what that means here,” Charlie leaned in
again, trying to get a look at Dean’s face. “But I am at a loss. Spill it or
you get the fork.”
            “Well the putting out is on the money,” Dean hinted, not ready to
say it out loud. He was not ashamed that it was a guy, he just tended to mess
around with people who had breasts, at least, as far as his friends were
concerned.
            “You dog,” Charlie caught on quickly. “What is Mr. Putting out’s
name?”
            “Cas..” Dean coughed out the name, not ready to fully give the guy
up. “Castiel.”
            “I’m sorry,” Charlie spat out sarcastically. “I couldn’t catch his
name behind your fake as shit, incredibly sudden, I don’t actually have
allergies, allergy attack.”
            “Castiel,” Dean said his name perfectly clear this time but made
sure to keep his voice down so that, for sure, only they could hear it. “His
name is Castiel.”
            “What kind of name is that?” Charlie asked and Dean laughed. It was
definitely not a name that one heard very often.
            “I don’t know,” Dean shrugged. How would he know how the guy got
such a weird name?
            “Sorry,” Charlie waved her hand about in front of them. “Continue
on with this question asking, advice needing business.”
            “Well, we have been kind of seeing each other.” Dean was not really
sure what to call them though. “Not like dating though. It has been more sexual
than anything.”
            “And you want to know how to make it more about dating?” Charlie
assumed.
            “No,” Dean shook his head. “I am okay with it being sexual. That
isn’t the problem.”
            “Then what is the problem?”
            “Well. He is … um … He’s …”
            “Spit it out.”
            “He is in his thirties. I think. Possibly late twenties.”
            “Um … What?”
            “He works with my mom.”
            “And you just walked in to her work one day and decided to have sex
with her co-worker?”
            “Well no. I babysat his son for him and it just sort of happened.”
            “While you were babysitting.”
            “God. It’s not like the kid was awake or anything. And besides. The
last couple times, he has made sure that his son was at his mother’s.”
            “So, what exactly do you need my advice on?”
            “He kind of,” Dean was not sure how to word himself at this point.
“He mentioned that I am a rush to be with. I don’t want him to lose that
feeling.”
            “Okay,” Charlie seemed satisfied with that answer. “You want to
keep the relationship as thrilling as it is now?”
            “Exactly,” Dean nodded. “But I am not sure how to do that. I feel
that if I just keep coming to his house and fooling around, he is going to get
bored with me.”
            “Easy,” Charlie acted as if she had this all figured out. Was Dean
really that stupid to not know how to keep a relationship alive?
            “Easy?” Dean questioned, swallowing hard. “What is easy?”
            “The solution,” Charlie quipped.
            “And what is the solution.”
            “Don’t keep doing things at his house.”
            “Where do you suppose I do them?”
            “I don’t know. Anywhere. A hotel. His office. His car down some
back alley.”
            “Seriously?”
            “Yeah.”
            “What if he doesn’t like it?”
            “Then you either go back to doing it at his house or it ends and
you stop worry about please some old dude.”
            “You think?”
            “I know.”
            “Okay. Cool. I can do that.”
            “What do we say?”
            “Thank you.”
            “Thank you what?”
            “Thank you, My Lady.”
            “You are welcome handmaiden.”
            “I hate you.”
            “I hate you too.”
 
_____
 
[You 1:42pm] Do you have Jimmy this evening?
[Castiel 2:08pm] No I do not. Would you like to babysit for me this evening?
[You 2:17pm] Actually, I was wondering if you could meet me somewhere.
[Castiel 2:20pm] Meet you? Where?
[You 2:30pm] I will send you the address at 5 and I would like you to be there
by 7.
[Castiel 2:36pm] I never said I would actually meet you anywhere.
[You 2:40pm] Show up or don’t. Have a good rest of your day.
[Castiel 2:44pm] Dean?
[Castiel 2:59pm] Dean?
[Castiel 3:15pm] Dammit Dean. Answer me.
 
_____
            Dean texted Castiel the address to a bowling alley on the other
side of town. It was generally pretty busy on a Friday night but Dean did not
care. He used to work here and he knew the ins and outs of the place. He would
be able to pull off what he had planned. The only thing that Dean did not have
the ability to know for sure was whether or not Castiel was going to show up.
 
[Castiel 7:05pm] I am in the parking lot. I am not sure if I can come in.
[Dean 7:08pm] You do not have to come in. There is a big yellow door around
back. Meet me there at 7:15.
 
            Dean pushed open the door at 7:15 on the dot to find Castiel
standing against the building. He looked like a deer in the headlights. Dean
knew that he was worried but he would not put him in a situation where he would
get caught, at least not anytime soon. They needed to make this work before
Dean discovered how far he could push things with Castiel.
            “Hurry,” Dean looked around once as well as he motioned for Castiel
to come inside.
            Castiel quickly entered the back room of the bowling alley. It was
so busy out there that no one would come back here unless there as a dire
reason to do so.
            “I am not sure I should be here Dean,” Castiel shoved his hands
into his pockets.
            “Follow me,” Dean did not stray from his plans. If Castiel was
going to bail it would not be because of anything Dean says.
            Dean looked back a few times as he made his way up two flights of
stairs and to his delight, Castiel was right behind him. Finally, with a good
shove, Dean pushed open the door to the bowling alley’s attic and stepped
inside.
            “What is this?” Castiel asked as he followed Dean inside the dark
room.
            Dean shut the door firmly behind them. If Castiel tried to leave
now, it would take him a while, this door really was a bitch to open if you did
not know all of its secrets.
            “This is the attic to the bowling alley,” Dean answered as he
pulled a flashlight out of his back pocket and turned it on, shining it just on
his face. The look of concern and intrigue on Castiel’s face made him want to
jump him right there.
            “Why are we up here?” Castiel continued on with his questions.
            “Because it is the only place that no one ever comes,” Dean
answered.
            “And you know this how?”
            “I used to work here. Trust me, people flipped coins to decide who
has to come up here.”
            “Why would they do that? What is wrong with this place?”
            “Someone got murdered here once. People now think it is haunted.”
            “That is comforting. Did you bring me here to make me victim number
two?”
            “No,” Dean laughed, taking a few steps closer to Castiel. “I came
here to do this.”
            Dean dropped to his knees in front of Castiel but turned slightly
to light the candles that he had placed on the ground earlier. He had brought a
supply bag earlier in the day. Once the candles were lit, he turned his eyes up
to Castiel, his hands running up Castiel’s legs.
            “Dean why did you bring me here?” Castiel questioned, looking
around the attic.
            “There are at least 100 people in this building with us,” Dean
smile up at Castiel as his hands continued to make their way up.
            “Your point?” Castiel did not seem to be catching on.
            “You are going to scream my name,” Dean’s fingers grazed over
Castiel’s belt. “In a building with hundreds of people inside.”
            “Dean,” Castiel’s pupils grew so large you could not see a speck of
blue in the dim light. “We can’t.”
            “Okay,” Dean did not stop his actions. He quickly worked to remove
Castiel’s belt and toss it aside. “You can stop me at any time.”
            Dean began to slowly unhook Castiel’s pants and slide them down his
legs until they rested at his ankles. Castiel stood still, not moving to stop
Dean, just as Dean knew he would. He could tell by the movements in Castiel’s
chest that he was already breathing heavily. Dean did not let this distract him
from the task at hand. He trailed his fingers back up Castiel’s legs and hooked
his fingers into the waistline of his boxers. Soon they were down around
Castiel’s ankles with his pants.
            “Ready to scream for me?” Dean growled, just as he moved forward
and sucked Castiel’s cock into his mouth, not giving him time to answer.
            Castiel’s knees shook and bent down slightly as the feel of Dean’s
mouth on his cock. The noises that instantly left his mouth told Dean that he
was enjoying this and that was all that Dean wanted. He wanted Castiel to want
him.
            Dean slowly worked Castiel’s cock into his mouth, occasionally
pulling all the way back and licking at the tip before taking it again. He did
this until Castiel’s cock was touching the back of his throat. Dean did not
even fight the gag, instead he embraced it, letting it cause his mouth to be as
wet as possible, spit running down the sides of his lips.
            “Oh fuck,” Castiel gripped the back of Dean’s head and looked down
at him. Dean could feel the tears that were falling from his eyes from the
gagging that was taking place but he could see that Castiel loved every second
of it. Dean did his best to smile with his eyes.
            “You are going to be the,” Castiel began, stopping to growl the
dirtiest of growls that Dean had ever heard and he had watched more porn than
he bothered to truly admit. The sound that left Castiel’s chest before he
continued speaking was something truly primal. It was the sound that a tiger
would make moments before attacking its next meal. “Death of me.”
            Dean fucked his mouth around Castiel’s cock and Castiel helped by
pushing his hips forward to meet Dean’s motions.
            “Oh, God,” Castiel cried out, his body moving into a jerk. Soon he
was coming down Dean’s throats, filling him to the brink. Cum leaked from
Dean’s mouth, no matter how hard he tried to swallow. It was too much.
            The feeling of Castiel filling his throat and mouth was enough to
send Dean over the edge. Soon his own body was jerking slightly as he came in
his pants. He had not even touched himself. Just Castiel cumming in him and the
friction from his boxers and jeans was enough to send him completely over the
edge.
            Dean finally pulled away from Castiel and sat down on the ground.
He needed a moment to regain control of himself. Castiel had enough control to
pull up his boxers before sitting down but that was all. For what felt like an
hour they just sat there, no sounds beyond that of the bowling alley below
them.
            “What is your favorite food?” Dean finally broke the silence,
unsure of where the question had come from. Though deep down he knew the
answer. He wanted all of Castiel, even the parts did not involve his mouth
getting fucked.
            “Um,” Castiel shifted, bringing his eyes up to meet Deans. “I … uh
… I really love bacon cheeseburgers.”
            “That sounds amazing,” Dean suddenly realized how hungry he was.
            “We could go back to my place and I could make us some,” Castiel
smiled over at Dean. “If you would like?”
            “I would really like that,” Dean smiled. “I am going to clean up
here and then I can come over.”
            “Great,” Castiel brought himself to his feet and pulled his pants
up. He looked a mess but would not gather any strange glances walking to his
car. “I will see you there.”
            “Okay,” Dean smiled. He just needed to change clothes, which he
thankfully had in the impala and then he would be right behind him.
            “Hey Dean?” Castiel stopped at the door of the attic.
            “Yeah?”
            “What is your favorite food?”
            “Pie. Apple mainly but I am not a pie snob.”
            “Pie.” Castiel said, more to himself than to Dean. It was as if he
were making a mental note to remember it. “Pie is good.”
            “Pie is awesome,” Dean corrected him.
            “Right,” Castiel looked Dean over and smiled. “Pie is awesome.”
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