Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/8865508.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester, Castiel_&_Dean_Winchester
  Character:
      Dean_Winchester, Castiel, Mary_Winchester
  Additional Tags:
      Blow_Jobs, Older_Castiel, Younger_Dean, Babysitter_Dean, Prostitute_Dean
  Series:
      Part 2 of The_Babysitter_Chronicles
  Stats:
      Published: 2016-12-16 Words: 2000
****** Prostitution is Illegal ******
by crowleyhasfeels
Summary
     Dean is worried about what happened between himself and Castiel. So
     when Castiel requests his babysitting services again, he is nervous
     about what is to come.
 
            Dean knew that what had taken place with Castiel was wrong. Castiel
was going through a hard time and Dean took advantage of that. He should have
just left when Castiel arrived home. Now all he could think about was how badly
he messed up. The only thing that kept him slightly off the edge was knowing
that Castiel was not going to say anything. It was not because Castiel was not
mad or upset with Dean, but because Dean is underage and if Castiel were to
tell anyone, he could be in some serious trouble.
            “Morning,” Mary smiled up at Dean as he entered the kitchen. He
tried to avoid eye contact but he knew that if he did not smile back, she would
know something was up.
            “Morning mom,” Dean returned the smile but quickly busied himself
with making a cup of coffee.
            “I talked to Castiel this morning,” His mother mentioned, turning
back to the newspaper that she was reading. He was glad she looked down or she
would have seen him spill coffee all over the counter. Dean quickly cleaned it
up to avoid questions.
            “Oh?” Dean questioned, working to pour himself a cup of coffee
without a mess. “Is everything okay?”
            “He said you were amazing with Jimmy,” Mary smiled up at him again,
sporting that proud of her son look. If only she knew how badly he had messed
up.
            “That’s good,” Dean grabbed the milk out of the fridge to add to
his coffee. “Jimmy is a great kid.”
            “He was hoping that you would be able to watch him again tonight,”
Dean choked on his first sip of coffee. Coffee did not seem to be on his side
today. “I guess his date went pretty good. They are going out again.”
            “They are?” Dean questioned. The date did not go well at all. Why
would Castiel be going out with her again? Maybe she had called and cleared
things up. Dean almost felt stupid. “Um, yeah, I could watch the little man
again.”
            “I will call and let him know,” Mary nodded, grabbing her coffee
and paper and standing up from the table. “Be there by seven, okay?”
            “Sure thing,” Dean nodded, staring down into his coffee. He was
more confused than ever now.
_____
            “Dean,” Castiel greeted Dean with a smile and stepped out of his
way so he could walk in. “Thank you for coming again at such short notice.”
            “Not a problem man,” Dean shoved his hands into his pockets and
looked around. Should he say something? Should he apologize to Castiel? Were
they just going to pretend that it never happened and get on with their lives?
If Dean had not agreed to this already, he would have turned around and left.
This was more awkward than he had expected it to be. “The kid is fun.”
            “He also,” Castiel closed the door behind Dean and locked it.
Dean’s entire body stiffened up at the gesture and his heart began to race. He
was locked in. “He also isn’t here.”
            “He what?” Dean stuttered over his words.
            “His mom picked him up this afternoon,” Castiel ran his hands
through his hair before stepping forward. Dean knew he should step back but he
could not will his feet to move. “She had something she wanted to take him to
do in the morning.”
            “Oh,” Dean looked around and then made eye contact with Castiel.
“You could have called to let me know.”
            “I knew when I called to see if you could watch him,” Castiel gave
Dean a slight smirk and Dean could not help but smile at him, it was a sight to
behold.
            “So, Jimmy was never going to be here?” Dean questioned again, his
heart beating even faster than it was before.
            “No, he wasn’t,’ Castiel admitted, looking down at his feet.
            “So, why did you ask for me to be here?” Dean questioned stupidly.
Though, honestly, there were probably a million different answers to his
question.
            “I woke up this morning thinking about what happened last night,”
Castiel took a few more steps forward and this time Dean could not help but
step back. This continued on until Dean’s back was against the wall. “About how
hurt I had been when I got home.”
            “Hurt?” Dean squeaked out.
            “That woman made me feel bad about myself,” Castiel answered. “But
you…”
            “I?” Dean finally spoke again after a few minutes of silence as
Castiel seemed to be looking for words.
            “Yes,” Castiel pulled himself back into reality. “You, however,
made me feel alive. Do you know how long it has been since I have felt alive,
Dean?”
            “No,” Dean shook his head. He could feel all of his blood pumping
quickly through his veins.
            “Three damn years,” Castiel answered, closing himself in closer
against Dean. “Three long years feeling like I was just walking numbly through
life.”
            “That sounds horrible man,” Dean added in, needing to know where
this was going, though he had a pretty good idea.
            “It really is,” Castiel nodded.
            Castiel moved forward another step and was definitely unable to
move further anymore. Dean was nicely pinned against the wall, cock already
hard and aching in his pants. He did not mean to be so turned on but Castiel
was so close and so warm against his body.
            “Dean,” Castiel breathed out in his deep, whiskey on the rocks
voice.
            “Yeah?” Dean tried to sound calm and collected but he was far from
it. How he had gone from confident Dean yesterday to barely able to put
sentences together Dean today was beyond him.
            “I want to feel alive,” Castiel ghosted his lips over Dean’s,
hovering just close enough to feel his breath but not close enough for them to
touch without further movement.
            “Can I,” Dean took a deep breath, working to calm his nerves down.
He needed calm and collected Dean back. “Can I help you with that?”
            “I would very much like that, Dean.” Castiel tilted his head to the
side, looking Dean over and Dean nearly lost all control of his knees. What the
hell was this man doing to him?
            “How can I be of assistance?” Dean asked again, slowly gaining
control over his sentence making; if nothing else.
            “I would like to,” Castiel smiled, again tilting his head to the
side in a leg quacking way. “As you put it ‘blow you.’”
            “Oh, fuck yes,” Dean wondered if it was possible for a cock to get
so hard it could rip through clothes. If it wasn’t, his was sure close.
            “Feel free to fuck my mouth,” Castiel winked at Dean before
dropping to his knees in front of him.
            Dean was not one to get off too fast but as the words left
Castiel’s mouth, he damn near came in his pants. But he was not going to be
that guy. So, he took another couple deep breaths and tried to think of things
that would hold him back off the ledge.
            Castiel began to unbutton Dean’s pants and in a swift motion, his
pants and boxers were down around his ankles. Dean could feel his knees going
weak again at the action. Castiel could sense this as well and laid his arm
over Dean’s legs, keeping him up and steady.
            “How do you like it, Dean?” Castiel questioned, though he didn’t
wait for an answer.
            As soon as the question was asked, Castiel’s mouth was trailing
kisses up Dean’s thighs, his nose lightly running over his cock. Dean moaned as
it twitched and Castiel let out a small moan as well. Dean knew then that he
was not going to make it long.
            Castiel kissed and licked around Dean’s thighs, slowly working his
way up until his mouth was wrapped around Dean’s balls. No one had ever done
that to Dean before. He had received his fair share of blowjobs but girls
tended to shy away from his balls. Blow jobs were never going to be the same
without it.
            Castiel sucked and licked at Dean’s balls and Dean began to pant,
hitting his fists back against the wall. This was too much. Castiel knew it as
well and pulled himself away, eliciting a whine from Dean.
            “Mmm,” Castiel moaned, running his hand up and cupping Dean’s balls
in them. “You sound so good.”
            Before Dean could thank him or think of anything else to say,
Castiel leaned forward and took Dean’s cock into his mouth. He did not work it
slowly, building it up like all of Dean’s other blow jobs. Instead, Castiel
went at it like he had not sucked cock in years and it was all that he wanted.
He went at it like he needed it; like his life depended on it.
            “Fuck,” Castiel pulled back away from Dean’s cock. “When I said
feel free to fuck my face, I didn’t mean it as a suggestion.”
            Castiel smiled up at Dean and then took his cock back into his
mouth. Dean let out a guttural moan. This was like a dream. None of this could
be real. This was not happening.
            “Oh fuck,” Dean cried out as he felt his cock hit the back of
Castiel’s throat. This was happening.
            Not wanting to disappoint, Dean reached out and grabbed a hold of
the back of Castiel’s hair, gripping his hair tightly with his fingers. Dean
then began to quickly thrust his hips back and forth into Castiel’s mouth. A
warm sensation took over his stomach and Dean knew he was going to be coming
soon.
            “Oh God, Cas,” Dean cried out. “I am going to cum man.”
            Castiel grabbed a hold of Dean’s hips and took him all the way in
his mouth, swallowing around his cock. That was all that Dean needed. Dean came
hard in Castiel’s mouth. It was slightly overwhelming and Dean tried to pull
his cock away but Castiel held him tightly into his mouth.
            “Oh fuck,” Dean leaned his head back and hit it against the wall.
            Castiel pulled back from Dean’s cock and brought himself to his
feet. His hair was even messier than normal and his eyes were so lust blown
that Dean could barely see the blue that they generally consisted of. He was
sure that his eyes did not look much different.
            “I don’t have Jimmy next weekend,” Castiel startled Dean with his
choice of conversation.
            “Okay?” Dean questioned, pulling his mind back to the reality of
the situation.
            “I hope you are available to babysit,” Castiel winked at Dean
before taking Dean’s mouth with his own.
            Dean melted into the kiss and moaned with the salty taste of his
cum hit his lips. He had never kissed any girl right after they had gone down
on him. He was not sure to regret that or if it was just amazing because of the
man he was kissing.
            “I think,” Dean pulled back and leaned his head against the wall
again. “I think I am free to babysit.”
            “Good,” Castiel smiled.
            Castiel pushed himself away from Dean and disappeared down the
hall. Dean used this time to pull his boxers and pants back on.
            “Are you hungry?” Castiel finally reappeared. “Your parents might
find it weird if you return home so soon.”
            “I could definitely eat,” Dean smiled and made his way over to the
couch.
            “Here,” Castiel held out his hand for Dean.
            Dean was confused at first before he saw the money in Castiel’s
hand. He wanted to argue that Castiel did not need to pay him but his parents
would be concerned if he was doing all this babysitting but had no money to
show for it.
            “Thank you,” Dean smiled up at him and took the money. Castiel then
made his way into the kitchen to start making them something to eat.
            “Shit,” Dean whispered to himself as he shoved the money into his
pocket. “I am a prostitute.”
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