Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/9283586.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Dean_Winchester, Castiel, Mary_Winchester, Charlie_Bradbury
  Additional Tags:
      Masturbation, Feelings, Gentle_Dom_Castiel, Sub_Dean, Dom/sub_Undertones,
      Come_Eating
  Series:
      Part 4 of The_Babysitter_Chronicles
  Stats:
      Published: 2017-01-11 Words: 2796
****** Feelings and Shit ******
by crowleyhasfeels
Summary
     Dean is worried that his feelings for Castiel will ruin whatever it
     is they have going on. He can't hold them in any longer though, so he
     admits that he cares for Castiel. Things do not go as he expected and
     that is the best way they could have gone.
            Dean was not really sure how to feel about the things that were
going on in his life. He was in high school, unsure of where his future was
headed and he was sleeping with an older man. Well, he was not really sleeping
with him. Castiel and Dean had not had sex yet, only sexual relations of the
oral variety but that did not mean they were not going to get there. At least,
Dean hoped that they would get there.
            “So, hot shot,” Charlie climbed into the Impala after school. They
were working on a project together for school, so they decided to head
Charlie’s place to work on it. Dean’s house was always a little on the loud
sound. Charlie’s house, however, well, no one was ever home at Charlie’s house.
They all led very busy lives. “How is the man toy?”
            “Man toy?” Dean raised an eyebrow at his best friend. He loved her,
there was no denying that, but she tended to be overly cheesy most of the time.
            “Yeah,” Charlie wiggled her eyebrows at him. “That is what he is,
right?”
            “Well,” Dean had to stop and think about it. He was not sure what
Castiel was. They have never really discussed it. “I don’t really know what he
is.”
            “What do you want him to be?”
            “I … I don’t really know. I mean …”
            “Don’t lie to me, Dean Winchester.”
            “How am I lying to you?”
            “I see how you get when I talk about him. Your entire face lights
up.”
            “So. That means I like the guy.”
            “Yeah,” Charlie laughed, reaching down to mess with the radio.
Normally, something like that would get you killed in his car, but it was
Charlie. Charlie got away with things that other people did not. “You like
him.”
            “Yeah,” Dean repeated, shaking his head at her. “I like him.”
            “Just like him?”
            “I …” Dean was not sure how to answer that question. Right now, his
emotions around Cas were confusing. Part of him wanted to say he just liked him
and was having fun, nothing more. But the other part of him, the one that would
not seem to shut up, well, that part of him felt something completely
different.
            “You should talk to him,” Charlie suggested as they pulled into her
driveway.
            “I will,” Dean promised, though he felt like he was lying. He did
not really have a direct plan to talk to Castiel.
            “Okay,” Charlie shut the door behind her and turned around before
Dean had a chance to exit the car. “Go talk to him.”
            “Now?” Dean questioned, his eyes growing wide.
            “Yes,” Charlie placed her hands on her hips “Now.”
            “But we have,” Charlie put her hand up to cut him off.
            “Do you know anything about the subject we are working on?” Charlie
questioned him, already knowing the answer.
            “No,” Dean grumbled. “I figured you did though. That is how it
works. You do the work, I supply the awesome company.”
            “Well I don’t want the company,” Charlie stepped away from the car.
“So go talk to him. Now.”
            “But,” Dean tried to fight her but he always lost when it came to
Charlie.
            “I am going to go do our group project,” Charlie leaned down and
rested her hands against the car, again something that would get you killed if
you weren’t Charlie. “You want your name on it, right?”
            “Well, yeah,” Dean stuttered. “But…”
            “You go talk to him,” Charlie stood up. “Once you do that, I add
your name to the assignment and you get an A. You need the A, Winchester.”
            “I hate you,” Dean turned the Impala back on. “You are the worst
best friend ever.”
            “I love you too,” Charlie laughed. “Call me later.”
            “Yeah, yeah.”
            Dean watched Charlie turn around and disappear into the house. Once
she was inside, he had two options: Go home or go talk to Castiel. And
unfortunately, for Dean, he needed that A.
_____
            Dean looked down at his watch as he sat in Castiel’s driveway. It
was only three o’clock and if Castiel worked the same hours as his mother, he
would not be off for at least another two hours. Dean could have stayed and
worked on homework. Instead, he got to sit here, trying to figure out what it
was that he was going to say to Castiel.
            Before Dean realized what he was doing, he was on the road again,
heading to his mother’s … well, Castiel’s work. This was the stupidest idea
that he had ever had. But here he was, being completely stupid.
            “Hey mom,” Dean decided to change his stupid into something better.
Since his mother worked here, he decided that he would use this time to visit
her.
            “Dean?” Mary gave a questioning look at her son. “What happened?”
            “Can’t a guy just come visit his mom at work, for no reason?”
            “No, he cannot. What do you need? Do you need money?”
            “Mom,” Dean turned away from his mother, slightly embarrassed that
she would make that assumption, but then he decided he could use that to his
advantage.
            “Dean?” She questioned again, sitting back in her desk chair.
            “Yes. I need money,” Dean laughed. “But I don’t need it from you.
Mr. Novak told me that I could stop by and he would pay me what he owed me.”
            “Oh,” Mary sat up in her chair again. “That is good. How is that
working out?”
            “Great,” Dean smiled, clasping his hands together. “Jimmy is a
great kid.”
            “Good,” Mary smile and rubbed her hand over Dean’s thigh.
“Castiel’s office is two floors up.”
            “He doesn’t work down here with you?” Dean questioned, looking
around at all the partially opened cubicles.
            “No,” Mary laughed. “Castiel has a much better job than me. Has his
own office even.”
            “Cool,” Dean nodded thoughtfully. “Two floors up?”
            “Yep,” Mary nodded, “though I don’t know if anyone is there right
now. They work different hours than we do.”
            “I will go check,” Dean stood up from where he was sitting at his
mother’s desk. “If not, I will go check his house.”
            “Okay,” Mary smiled up at him. “I will see you at home later.”
            “Later mom,” Dean smiled back at her before heading over to the
elevator. This lying to his parents was becoming too easy. He was not sure how
he felt about it.
            Dean stepped into the elevator and pushed the button that read
four. It seemed that time slowed down after this. He had not seen Castiel in a
few days and it was possible that after today, he would not get to see him
again. Was he ready to ruin this?
            The doors swung open, pulling Dean out of his thoughts. He stepped
off the elevator, hesitating but still moving forward. He had come too far to
go back now. The only thing that could stop this conversation from happening
now would be Castiel not being here. That could be good.
            Dean made his way through an empty floor. The lights were off and
no one was in sight. He took a deep breath, relieved that he had missed
Castiel. He had more time to consider what it was that he was doing. He turned,
releasing the air he was holding in and began to head back toward the elevator.
            “Dean?” Dean stopped at the sound of Castiel’s voice. He would know
that voice anywhere.
            “Hey Cas,” Dean turned on the balls of his feet and was met with
bright blue eyes. Even in the darkness of the room, they stood out.
            “What are you doing here?” Castiel cocked his head to the side with
his question.
            “I needed to talk to you,” Dean said quickly, taking a step back.
“But it was a stupid idea. I should leave. I am sorry for coming to your work.”
            “Dean, stop,” Castiel reached out and grabbed Dean’s arm, pulling
him a few steps closer. “It’s okay. No one is here. We can talk in my office if
you like?”
            “Um,” Dean was scared. This was happening too fast. He was not
ready to lose Cas. “Yeah. Sure.”
            Castiel led Dean through what appeared to be a waiting room. It
looked nothing like the part of the building that his mother worked. He was
curious now as to what Castiel did but now was not the time to ask. If he got
the chance to ask later, he would.
            “Come in,” Castiel motioned his hand into his office and Dean
stepped inside. Castiel made his way in after Dean and shut the door behind
them. “What is this about Dean?”
            Dean looked over the office for a moment before turning his
attention back to Castiel. Cas held a confused expression on his face and a
slight look of panic. If anyone were to find out about them, Castiel could be
in all kinds of trouble. Dean did not want that for Castiel. Even though Dean
did not prove that with his bowling alley stunt, but that was not Castiel’s
work.
            “I should probably leave,” Dean went to exit Castiel’s office but
Castiel stopped him, holding him back. “I shouldn’t be here.”
            “What is this about Dean?” Castiel asked in a sterner tone of
voice.
            “I have just been thinking,” Dean could not make eye contact with
Castiel. “Something I really should not do.”
            “Thinking about what?” Castiel asked calmly and Dean was finally
able to look at him again.
            “Us,” Dean locked eyes with Castiel, fighting the tears that he
could feel forming. He could very well be about to lose him. This was too much
but it was too late.
            “Us?” Castiel questioned. He looked Dean over for a few moments
before walking past him and sitting on the edge of his desk. “Okay. Let’s talk
about us.”
            “I don’t,” Dean had planned a million different things.
            “Come here,” Castiel motioned for Dean to come toward him and Dean
obeyed.
            Dean moved slowly toward Castiel, his entire body shaking. He hated
when he did not know the outcome of something. He needed control but with
Castiel, he was never in any kind of control.
            “Dean?” Castiel grabbed Dean’s chin and brought their eyes
together. “Do you have feelings for me?”
            “Y … ye …” Dean finally nodded, unable to get the words out.
            “Dean?” Castiel was quick with the questioning tones.
            “Yeah?” Dean finally found his voice, even though it cracked.
            “I would like it very much,” Castiel lightly pulled Dean forward
and pressed a soft, quick kiss on his lips, “If you would go out with me.”
            “Like,” Dean leaned forward and kissed Castiel again, “on a date?”
            “No, not just on a date,” Castiel laughed, another kiss occurring
between them. “I was thinking more serious than that.”
            “Huh?” Dean pulled a Castiel and tilted his head to the side.
            “I would like to date you, Dean,” Castiel answered with a smile.
“Exclusively.”
            “You saying you want to be my boyfriend?” Dean asked with a smug
smile.
            “Yeah,” Castiel laughed, pulling Dean into a harder kiss. “That is
exactly what I am saying.”
            “Hey, Dean,” Castiel wrapped his arms around Dean and pulled him
completely against himself.
            “Cas?”
            “Everyone in my office has gone home already.”
            “Yeah?”
            “Yeah.”
            “What does that mean?”
            “It means that you should go lock my door.”
            “Okay,” Dean nodded, his entire body on edge, this time out of
excitement.
            Dean made his way across the office slowly and then turned the
deadbolt on Castiel’s office door. He was not sure why Castiel’s office
required that much protection but he was glad for it. The last thing they
needed was for someone to walk in on them.
            “Good,” Castiel smiled over at Dean. “Now turn off the light.”
            “Okay,” Dean flicked the light switch off. The room was now only
lit but the lamp on Castiel’s desk and the small amount of light that was
coming through the window blinds.
            “Now,” Castiel stood up from the desk and turned around. He grabbed
the few random items that were on his desk and moved them to a filing cabinet
across the room. The only thing left on the desk was a computer that seemed to
be attached to the desk and unable to be moved. “Take off all your clothes and
lay down on the desk.”
            “Yes, Sir,” Dean nearly fell over as he worked to take off his
clothes in record time. Soon he was completely naked, pulling himself up onto
Castiel’s desk and laying down on his back. He was too big for the desk though,
so his legs hung off the side.
            “You are so good,” Castiel made his way over to the desk and ran
his finger down Dean’s arm. “So, so good for me.”
            “I want to make you happy,” Dean admitted. Whatever it took to make
Castiel happy, he would do it.
            “And you do,” Castiel promised, leaning forward and pressing his
lips furiously to Dean’s.
            Castiel kissed Dean until they were struggling to breathe and then
pulled away. Dean whimpered and the disconnect, wanting nothing more than to
feel Castiel’s lips against his own. But Castiel had other ideas, as he leaned
back in and nibbled lightly at Dean’s ear.
            Dean groaned at the feeling of Castiel’s teeth scraping along his
ear lobe and almost slid off the desk when Castiel bit down on Dean’s neck. It
was not a soft bit either, Dean was going to have a mark on his neck when this
was over. He could not bring himself to care.
            Castiel nibbled his way down Dean’s collar bone before moving down
his chest. He spent a few minutes at each nipple, biting at them and flicking
over them with his tongue. Dean’s entire body felt like it was on fire and he
knew that whatever was going to happen, he was not going to last long at all.
He was too worked up to last.
            Castiel finally pulled away from Dean and walked around to the side
of the desk, pushing himself in between Dean’s legs. Once he was positioned
between Dean’s legs, he ran his hands over Dean’s thighs and down between them,
taking Dean’s balls between his fingers. Dean’s cock was harder than it had
ever been. No one had ever been so demanding of him and so gentle at the same
time. Castiel had yet to touch his dick and he was already on the verge of
orgasm.
            “Cas,” Dean cried out, pushing his hips up but Castiel pushed them
down quickly.
            “It’s okay Dean,” Castiel squeezed Dean’s balls gently with his
fingers and soon Dean was coming all over his stomach, thighs, and Castiel’s
hand. “That’s it.”
            Dean was panting, trying to bring himself down from his high.
Castiel had simply touched him, and not even his cock and here he was coming
all over himself.
            “I am sorry,” Dean apologized, even though Castiel, in no way,
seemed bothered by what had just happened.
            “Why is that?” Castiel asked, bringing his hand up to his mouth and
licking Dean’s come into his mouth.
            “Oh god,” Dean cried out at the sight. If Dean had not just come,
watching Castiel do what he just did would have sent him over the edge.
            “Like I said,” Castiel moved back around the desk and leaned down
to kiss Dean again. Dean moaned at the taste of himself on Castiel’s lips. “You
are so good to me.”
            “Anything for you,” Dean mumbled, rolling his eyes back.
            “Anything?” Castiel cocked an eyebrow at Dean.
            “Yes?” Dean answered but was unsure as to what he could be agreeing
to.
            “I need you to babysit for me all weekend,” Castiel stood up and
smiled down at Dean. “Out of town.”
            “Out of town?” Dean was finally able to sit himself up. “Why would
you need me to babysit out of town?”
            “Well,” Castiel walked over and grabbed Dean’s clothes from the
ground and walked them over to Dean. “I have a conference I have to go to on
Friday and I decided I wanted to stay the weekend. Jimmy will be at his
grandmother’s, also out of town. But no one needs to know that. You simply need
to come and “watch” him while I am busy with clients.”
            “I will see what I can do,” Dean smiled at Cas as he began to
redress.
            “Oh, and Dean,” Castiel moved back between Dean’s legs and kissed
Dean softly.
            “Yeah?” Dean asked between light, barely there, kisses. They were
the kind of kisses you read about in poems or some shit.
            “Saturday is my birthday,” Castiel smiled against Dean’s lips. “And
I really … I mean really … love satin panties.” 
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