Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/9304178.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Dean_Winchester, Castiel
  Additional Tags:
      Anal_Sex, Anal_Fingering, Oral_Sex, Rimming, Dean_in_Panties, Birthday,
      Older_Castiel, Younger_Dean, Underage_Sex, Hotel_Sex, First_Time, Suits,
      Pie
  Series:
      Part 7 of The_Babysitter_Chronicles
  Stats:
      Published: 2017-01-13 Words: 3429
****** Atlantic City Birthday Part 2 ******
by crowleyhasfeels
Summary
     Castiel's birthday takes a turn ... and a good one at that.
            As Dean had expected, Castiel already had some plans laid out for
his birthday. He had made some reservations at a fancy restaurant. Dean had not
really packed for fancy. Castiel had figured as much, so he took Dean shopping
that afternoon to find the perfect outfit. Dean was actually surprised how
amazing he looked in a suit. He wished he could show his mom how well he
cleaned up, but he settled for texting a photo to Charlie.
 
[You 6:43 pm] Image Sent
 
[Charlie 6:52 pm] Who is that?
 
[You 6:55 pm] Haha. Very funny.
 
[Charlie 6:59 pm] Wasn’t trying to be funny. Was just asking who it was. Geesh.
 
[You 7:00 pm] Seriously?
 
[Charlie 7:03 pm] You look great Dean.
 
[You 7:07 pm] Thank you. Never been dressed up before.
 
[Charlie 7:09 pm] Well you look like a God.
 
[You7:13 pm] I know.
 
[You 7:15 pm] Could you maybe do me a favor?
 
[Charlie 7:18 pm] Anything.
 
[You 7:20 pm] Delete this Conversation.
 
[Charlie 7:22pm] Done.
 
            Once they were all dressed up, Cas called them a cab and they
headed for the restaurant. Not only was he dressed fancy, but this place was
fancy as well. The nicest place Dean had ever been to was the Red Lobster. He
did not have to wear a suit to go to the Red Lobster, though he did have to
wear a pair of jeans without holes in them. That just shows how dressed up Dean
had gotten in all his years. Never.
            “Right this way,” A leggy blond, who Dean could not help but look
over, grabbed two menus and walked them through the packed restaurant. Dean was
not even sure how they were able to get a reservation or a table so quickly.
            “Thank you,” Castiel gave her a smile as they took their seats.
            I was not lost on Dean that they were getting looks from, not only
the waitress, but other people in the place as well. They could very well be
friends or business partners, or something of the like. But you didn’t get
dressed up and come to this place for dinner with friends. At least, Dean would
not assume that someone would. Castiel seemed to notice all the looks as well
but brushed it off.
            “This place is nice,” Dean tried to make some small talk, as he
opened up his menu to look it over. “Holy shit. This place is expensive.”
            “Please, Dean,” Castiel tilted his head to the side. “I would
appreciate it if at least for tonight, you paid no mind to the prices.”
            “How do I do that?” Dean looked over his menu at Castiel, working
to keep his voice down. “There is not a single meal on this menu that is under
fifty bucks.”
            “I am aware,” Castiel smiled over at Dean.
            “Okay, that’s it,” Dean set his menu down in front of him. “What
exactly do you do for a living? Cause my mom sure as shit don’t make this kind
of money.”
            “I am an investment banker,” Castiel answered casually, pulling up
his own menu to look it over. “Now please, don’t worry about the money.”
            “Yeah, okay.” Dean pulled his menu back up and looked it over. He
tried to look past the prices but it was all too much. Dean was not really sure
what an investment banker did or made but this place was just too expensive.
            “Dean?” Dean pulled his eyes up from the menu but kept his head
down. He did not know how to tell Castiel that all of this money that was being
spent on him was driving him crazy.
            “Yeah?” Dean pulled the menu down, just enough so Castiel could see
his face.
            “Would you like to go somewhere else?” Castiel questioned. “I do
not want to make you uncomfortable. I just heard about this place from a friend
and figured I would treat myself for my birthday.”
            “We can stay,” Dean felt like shit. He was ruining Castiel’s
birthday. If Castiel wanted to spend money for his birthday, who was Dean to
stop him.
            “No,” Castiel waved his hand toward the woman who had seated them
and she came right over. “Something has come up and we need to leave.”
            Castiel pulled out his wallet and handed the woman money. Dean
could not see how much it was but he felt bad all the same. Not only were they
leaving, Castiel still had to pay something for this adventure.
            “Let’s go,” Castiel motioned his head for the door, his smile never
leaving his face.
            “Please,” Dean tried to beg, but also did not want to draw any more
attention to them. “I did not mean for us to leave.”
            “It is perfectly fine Dean,” Castiel took Dean’s hand as soon as
they were outside and they began to walk down the street. “I should have known.
Really. This is my fault.”
            “You should have known?” Dean stopped them, trying to remove his
hand from Castiel’s, but Castiel wasn’t budging. “What? That I would ruin your
birthday dinner?”
            “No,” Castiel shook his head and pulled Dean closer to him. “That
is not what I meant at all.”
            “Then what did you mean?” Dean felt himself growing angry. He was
not just some kid that Castiel could buy off with fancy gifts and dinners. Even
the expensive suit he was wearing was starting to feel like too much.
            “What I should have known, Dean,” Castiel said Dean’s name, Causing
Dean to look up and make eye contact with him. “I should have known that I did
not have to buy your love. I keep trying to make things perfect you know? When
I was married, everything always had to be perfect. That is why our marriage
ended. I did not try hard enough to keep her happy.”
            “Whoa,” Dean shook his head. “It should never be your job to make
someone happy.”
            “I just wanted to do nice things for you, so that …” Castiel broke
eye contact with Dean but Dean reached out and grabbed his face, bringing it
back.
            “You know what makes me happy?” Dean asked.
            “What is that?”
            “This,” Dean smiled as reached up between them and grabbed
Castiel’s face again, this time pulling it towards his own. Part of Dean knew
that he needed to stop, Castiel seemed to not be ready for big public displays
of affection, but Castiel did not pull away. So Dean kissed him, soft but firm.
“And pie.”
            “Pie is good,” Castiel nodded, leaning his forehead against Dean’s.
            “No,” Dean laughed, finally stepping back. “Pie is awesome.”
            “Right,” Castiel agreed. “Forgot that part.”
            “So how about we get some pie,” Dean grabbed ahold of Castiel’s
hand again and forced them to start walking. “Then, we can go back to the hotel
and I can give you the present I got for you.”
            “I think that sounds amazing.”
_____
           
            They got their pie to go, both wanting to get back to the hotel.
Dean was very excited to show Castiel what he had gotten for him. They could
eat later.
            Once they were through the door of the hotel room, Castiel was
pushing Dean up against the wall and attacking his mouth. Dean loved how
Castiel was both an aggressive person and a shy person. Put him in the bedroom
and he could lead like no other but once they were out of the bedroom, Castiel
seemed out of his element. They were perfect for each other.
            “I … need … for … you,” Dean tried to speak through the kissing but
found it to be rather challenging. He was finally able to get Castiel off him
so that he could continue. “I need you to go sit down on the couch.”           
            Castiel reluctantly pulled away from Dean and made his way across
the room. Dean watched as Castiel sat down, never once taking his eyes off him.
Dean was the center of Castiel’s attention. This both frightened him and
thrilled him. No one had ever looked at him the way Cas looked at him.
            Dean waited until Castiel appeared to be comfortable and then set
his plan into motion. He was more nervous than he had ever been in his entire
life. Not because he didn’t want to do what he was about to do, but because it
was for Cas. This was his gift for Castiel and he wanted to get it right. He
needed to get it right.
            Dean slowly begins to remove his clothes. He takes off his tie,
setting it nicely over a chair, followed closely by his suit jacket. The
clothes were not cheap, he was not just going to toss them on the floor to get
ruined. So, he made sure to take extra care of them. After the coat came the
shirt. Dean smirked at Castiel who was watching intently at the scene in front
of him.
            Dean stopped at his pants. He could see Castiel’s widen with
anticipation. He knew what was coming, Dean could see it but did he know to
what extent.
            “Dean,” Castiel smiled up at him. “You didn’t?”
            “Oh, I did.” Dean smiled down at Castiel and unhooked his belt.
            The sound of his belt clearing the loops gave him the chills. Every
hair on his body was standing on end and he could see it was the same for
Castiel. Castiel wanted him. Castiel needed. They needed each other. Dean was
almost in tears by how much he needed this but he was not going to cry like
some little girl. Instead, he was going to stand up tall and give Castiel the
present he had asked for.
            Dean slowly starts to remove his slacks, showing off bright red
satin panties and a red garter to match. They are clipped down to a pair of
knee high, which stockings. Castiel begins to rub himself through his pants.
Dean is happy that Cas is happy.
            Castiel watches Dean fully remove his clothes, continuing to also
rub himself through is pants. It soon becomes very apparent that Castiel is
hard and that makes Dean’s dick perk up and strain through the panties.
            Dean slowly makes his way over to Castiel and sinks down to his
knees.
            “No,” Castiel shakes his head and points to the bed. “Lay down.”
            “But I want to,” Dean runs his hands along Castiel’s thighs, but
Castiel stops him.
            “Dean?”
            “Yeah?”
            “Do you know what today is?”
            “Your birthday?”
            “Yes, it is. And do you know what that means?”
            “Uh … no?”
            “That means you, Dean, will get your sexy ass over to that bed and
lay down.” Castiel points towards the bed and Dean swallows hard out of
excitement. “Do not make me carry you.”
            Dean broke eye contact with Castiel and hung his head. He refused
to move. He very much wanted Castiel to carry him over to the bed and have his
way with him. And judging from the growl that escaped Castiel’s mouth, he
really wanted it too. Next thing Dean knew, he was being pulled to his feet and
then up into Castiel’s arms. It was slightly romantic, in a, I might be
punished for this, kind of way. Dean was excited.
            Castiel walked them over to the bed and laid Dean down gently,
which is not what he had expected but he loved it just the same. He loved how
in control Castiel was but also how gentle he could be. Dean knew, no matter
what, Castiel was going to take care of him. He would never hurt him. Unless,
maybe if Dean asked, but that was a conversation for another time.
            Castiel moved to the bottom of the bed, remaining fully clothed. He
looked at Dean for a few minutes, taking him all in. Dean felt vulnerable and
strangely, it was an incredible feeling. He needed to be vulnerable to Castiel,
just as Castiel was vulnerable to him.
            Castiel removed his jacket and loosened his tie before climbing up
between Dean’s legs. Dean could feel his breaths becoming erratic and Castiel
noticed it too. Castiel lightly ran his fingers over Dean’s thighs, causing him
to suck in air.
            “You are so beautiful,” Castiel whispered.
            “No,” Dean went to argue but stopped talking as soon as Castiel
leaned up to him and took his nipple into his mouth.
            This was supposed to be about Castiel. This was his birthday. Dean
was supposed to be pleasuring him but that did not turn out to be the case.
Castiel never ceased to amazing him.
            “Oh fuck,” Dean cried out as Castiel palmed at his cock. It was
hard beneath the panties. Precum pooling against the fabric, leaving a wet
spot.
            “That’s it,” Castiel’s voice dropped deeper than normal and Dean
almost lost it. How could this man keep getting hotter? “So, so good.”
            “Yes,” Dean moaned, pushing his hips up into Castiel’s hand. “Good.
So, good.”
            Everything from that point forward was a blur. Rubbing. Sucking.
Biting. Licking. Dean was losing his mind, gripping onto the bed, trying to
hold on to his sanity. It got harder with everything light nibble against his
balls. Then it happened. Dean nearly flew off the bed as Castiel pushed his
tongue against Dean’s ass. No one had ever licked his ass before.
            “Oh god,” Dean cried out in ecstasy.
            “You,” Castiel laughed, breaching the ring of muscles with his
tongue. “You can call me Cas.”
            “Fuck, Cas,” Dean tried to laugh but Cas pushed his tongue into his
ass again. “Please?”
            “Please what?” Castiel ordered an answer.
            “Fuck me,” Dean begged, already on the edge of his orgasm.
            “I can’t do that,” Castiel said calmly, right before pushing a wet
finger into Dean.
            Dean bucked his hips up at the feeling. It was an amazing feeling
but it was mixed with a slight burning pain. He had once tried to stick his
fingers in himself but he failed. He had been scared that he was doing it
wrong.
            “Cas,” Dean cried out, pushing against Castiel’s finger. Cas slowly
began to work it in and out until … stars. Dean was seeing stars. “Oh, fuck.
Oh, fuck. Oh, fuck.”
Dean was coming down from his orgasm. The room was lightly spinning and it felt
like that time he had gotten drunk with Charlie when they stayed away overnight
for comic con. This was very much like that moment but so much different. He
much preferred this moment.
            “Have I ever told you how good you are to me?” Castiel asked,
running lazy kisses up Dean’s shoulder, his neck and then nibbling on his ear.
            “Every day,” Dean smiled, turning his head to kiss Cas.
            “Good,” Castiel smiled back into the kiss. “Don’t want you to
forget.”
            “Cas,” Dean turned this amazing moment serious and Cas pulled away,
but not so far as to not be touching him anymore. “Do you really love me?”
            “I am sad that you have to ask me that.”
            “I’m sorry but I need to know.”
            “I love you, Dean Winchester. I love you so damn much.”
            “Then, why?”
            “Why what?”
            “Why won’t you fuck me?”
            “I have my reasons.”
            “Fine.”
            “Dean …”
            “What?” The words came out a little harsher than Dean had meant for
them too.
            “Would you like to maybe,” Castiel looked Dean in the eyes, there
were so many emotions there that Dean could not figure out what they were.
“Would you like to fuck me?”
            “Really?”
            “Yes.”
            “But I … I have no idea how to fuck another man.”
            “I can walk you through it. Once you get started, it is pretty easy
to catch on.”
            “Can you,” Dean took a deep breath. He did not want to push his
luck with what he was given. “Can you be on top? I like when you are in
control.”
            “I can,” Castiel agrees, leaning forward and kissing Dean.
            Castiel moved off the bed and slowly removed his clothes. Dean
watched with wide eyes. He could not believe this was going to happen. He was
instantly hard again. Thank God for his lively sex drive. He could go forever
if Cas would let him.
            Once Cas was naked, he walked over to his suitcase and pulled
something out. Dean soon learned that this was lube. Castiel had been prepared.
Had he planned on fucking Dean? Did he know that Dean was going to agree to
fuck him? Was he just always prepared? Castiel then produced a condom. Yeah. He
knew this was going to happen.
            “Take the panties and garter off,” Castiel instructed Dean.
            Dean sat himself up on the bed and began to work them off. All the
way, Castiel opened the bottle of lube and put a generous amount on his
fingers. Dean could almost not continue undressing when Castiel climbed onto
his knees on the bed and reached behind him from between his legs. Castiel
locked eyes with Dean as he slowly began to work his fingers in and out of
himself.
            “You are the most amazing man I have ever met,” Dean got onto his
knees and leaned forward to kiss Castiel.
            “Good,” Castiel moaned out his answer. “Lay down.”
            Dean moved quickly, lying onto his back. He continued to watch
Castiel fuck his fingers in and out of him, small moans escaping his mouth.
Dean knew that this was not going to last long for him. But hey, he seemed to
have no trouble getting hard again. So there was that.
            Once Castiel was good and opened up, he kissed his way up Dean,
stopping at his cock and kissing the tip. It twitched against Castiel’s mouth
and Dean let out a moan. Castiel smiled up at him, grabbed the lube from the
bed and put more onto his fingers that he had removed from his ass. He massaged
it between his fingers, warming it up. He grabbed the condom with his non-lube
covered hand, sliding it onto Dean, before wrapping his hand around Dean’s cock
and getting it nice and coated.
            Dean closed his eyes at the feeling but quickly opened them when he
felt the bed shift. Castiel slowly made his way onto Dean, straddling his hips.
Their cocks brushed against each other and Dean let out a whine.
            “Are you ready?” Castiel asked Dean, still stroking lightly at his
cock.
            “Very,” Dean could barely get the words out; his nerves were on
over drive.
            Castiel stroked him for a few moments longer before lifting himself
up over Dean. He gripped Dean’s cock at the base and slowly, almost painfully
slowly, lowered himself onto Dean’s cock. He would move down a little, pull
back up and then move down further. He kept this slow motion up until Dean’s
cock was buried inside of him.
            Castiel took one of his hands and placed it on Dean’s stomach,
using it for leverage. He then took his other hand and wrapped his fingers with
Dean’s. The connection was more than Dean could hope for. This was important.
This was bigger than he thought it would be. This was Castiel loving him.
            “Mmm,” Castiel moaned as he slowly began to bounce up and down on
Dean’s cock.
            Dean threw his head back but made sure to keep his eyes open. He
did not want to miss a single expression on Castiel’s face. Up and down,
Castiel bounced, getting faster and slamming down harder each time. Dean could
feel his stomach tightening.
            “Fuck,” Dean cried out. “I am so close. Shit.”
            “Yes,” Castiel took Dean’s hand and wrapped it around his cock.
“Come with me.”
            Dean stroked at Castiel’s cock and they locked eyes. It only took a
matter of moments and Castiel was coming all over Dean’s hand, stomach, and
chest. At the very same moment, Dean thrust hard up into Castiel, coming harder
than he had ever come. For a moment, he felt as if he was going to pass out.
            “I love you, Dean.” Castiel leaned down and took Dean’s mouth with
his own.
            “I love you, Cas.”
            “Can I tell you a secret?” Castiel asked as he collapsed down onto
Dean.
            “You can tell me anything.”
            “This has been, by far, the greatest birthday I have ever had.”
            “Yeah?”
            “Yeah.”
            “Well guess what?”
            “What?”
            “It isn’t over yet.”
            “Oh, God,” Castiel groaned. “I can’t do that again.”
            “No,” Dean shook his head and then kissed Castiel. “No more sex.”
            “Then what?”
            “Pie.”
            “Pie?”
            “Oh yeah. Pie.”
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