Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/789063.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Castiel, Dean_Winchester
  Additional Tags:
      AU, Feminization, Crossdressing, Middle_School, PWP, Shota, shota!cas,
      Established_Relationship
  Stats:
      Published: 2013-05-08 Words: 1259
****** Baby Blue ******
by pastelcastiel
Summary
     The theater department got new costumes in and Castiel wants to show
     them to Dean.
Notes
     Castiel is 11 years old in this fic.
Dean got a job as the janitor at a middle school just to earn some extra money
to fix up the Impala. He didn’t intend on earning the heart of a blue-eyed boy.
*****
“Thank you so much for coming in last minute!” The school’s theater teacher
exclaimed as she saw Dean walking towards the classroom.
“No problem, Ms. Moseley.” Dean replied as he walked into the theater room.
“They assigned me bus duty this week and one of my students is still trying to
put up the set.”
“Don’t worry. I’ll lock up the classroom as soon as they’re done.” He look
towards the direction of the noise coming from behind the curtain on the stage.
“Bless your heart, Dean.” And with that, Mrs. Moseley left the classroom and
walked towards the bus loading zone.
Dean waited a few moments before he approached the stage and made his way
behind the curtain to the student who was cleaning up the props and costumes.
“Signed up for cleaning duties again I see.” Dean said, the boy looked back
with a smile immediately on his face
“We got some pretty costumes in and I wanted to show you.” The boy abandoned
the job he was working and went into the closet where they kept all the
costumes in.
“What kind of pretty costumes, Cas?” Dean shouted out as he took a seat in the
old couch at the back of the stage. He remembers bringing it in when one of the
student’s parents donated it to the theater department. Who knew it was going
to come in handy for him and Castiel.
“I’ll show you in a second!”Cas said from inside the closet. Dean could hear
hangers being moved around on the clothing rack and clothing being shuffled
around. After a few moments Cas peaked his head around the closet door and
looked at Dean.
“Don’t…don’t laugh, okay?” Cas said as he slowly came into view after Dean
agreed. Castiel came out wearing a baby blue dress that hit just slightly above
his knees. The dress was held up by thin straps which crossed behind the boy’s
back. Dean stared at him, mouth agape, taking him all in. When Dean didn't say
anything after a few moments, Cas dropped eye contact.
“You don’t like it?” The boy said, barely above a whisper.
“Oh, of course I do, baby. It fits you perfectly.” Dean’s response made the
biggest smile appear on Cas’ face, along with a deep blush.
“It matches your pretty eyes too.” Dean licked his dried lips and held his hand
out, signaling to the boy to come to him.
“It matches my undies too, you know…” The boy replied as he grabbed onto Dean’s
hand and directed it to the hem of the dress. Dean instantly lifted up the
dress and just like Cas said, they matched the dress perfectly. He wore a pair
of baby blue panties with lace fringe on the sides. Dean could see that his
little prick was standing tall.
“You like wearing pretty things for me don’t you, Cas?” Dean spoke as he ran
his fingers up and down the boy’s thighs. He felt a shiver run through his
little body and it made Dean so hard that the simplest touch had so much effect
on this boy.
“What else do you like to do for me?” He question, pulling the boy closer and
making him stand in between his opened legs. Cas’ hands instantly went to grip
on to Dean’s shoulders. “I like opening myself wide so you can easily slip in
when we see each other.” Cas answered, his voice shaking as Dean’s hand slipped
inside his panties and slowly teased his stretched out hole. He let out a small
whine, wanting him to slip inside him already.
“You stretched yourself out in the little boy’s room?” Dean moved away his
teasing hand and gripped onto both of Cas’ thighs, easily picking him up and
making the boy straddle his waist. He loved how easily it was to move Castiel
around.
“I opened myself up during lunch.” The boy replied as he slowly grinded down
onto Dean. He could feel his thick cock through his janitor’s outfit and it
made him happy that he got his Dean so hard just by wearing a pretty little
dress. Dean stilled the boys movements with his hands which earned him another
whimper. “Do you want to keep grinding against or would you like it inside
you?” Without even answering, Cas’ thin hands instantly went to Dean’s pants
and started to unbutton and zipping him out of it. Dean smiled at how eager he
was.
Castiel gripped onto Dean’s hard cock and pulled him out completely. Without
being told, Cas’ spit onto his hand and ran his hand all over the shaft and
tip. Dean leaned back onto the couch and watched as Castiel bundled up the
dress around his waist with one hand and the other moved his panties aside. He
lined his little hole up to the tip of Dean’s cock and slowly sunk down,
letting out a gasp as the tip entered him.
Dean let out a grunt, Cas was still tight even after stretching himself up. The
boy continued to sink down slowly, and all Dean wanted to do was shove him all
the way down and fuck up into him. When he finally took in as much as could, he
let the dress fall and grabbed onto one of Dean’s shoulders. He panted as he
adjusted to him.
Dean grabbed onto his chin, pulling him down and kissed the boy. Cas kissed
back, letting out a moan as Dean darted out his tongue. A few minutes later,
Cas started to move, bouncing on Dean’s cock. He let out a grunt as he slipped
in and out of Cas. He had waited for this moment all day.
Dean was even tempted to relieve himself in the employee restroom after he had
finished cleaning the cafeteria. But the wait was worth it, now that he had his
Cas bouncing up and down on his cock.
“D-Dean…” The boy moaned out as he sped up his movements.
“What is it, baby?” Dean gripped onto Cas’ thighs, trying to slow down his
movements but it was no luck.
“Tell me how pretty I look….”.
Dean smiled up to his boy and slowly started to plant kisses all over his neck.
“So much prettier than any girl I've ever seen” Cas gripped tighten on Dean’s
shoulder and he knew he was getting close. “No one else could look prettier in
this little dress than you, baby.” Dean paused for a little while as he felt
himself get close too.
“Stain up your pretty panties…” Dean grunted as Cas’ hole felt like it got
impossibly tighter. “I want you to feel your come through the front and mine
through the back.” A few second later, Cas did just that and came all over
himself, Dean followed shortly after.
*******
The only sound heard in the theater was their heavy breathing. Dean had his
head leaned against Castiel’s boney chest and Cas has his on top of Dean’s
head.
After a few moments of silence Cas finally broke the silence.”You know…there’s
still more costumes in there.” Cas smiled down at Dean when he felt him smile
against him. Dean pulled his head away from his chest and gave his boy a quick
kiss. “Good thing it’s Friday, we got all weekend to try them out.”
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