Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4706126.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Dean_Winchester, Castiel
  Additional Tags:
      Anal_Sex, Loss_of_Virginity, Implied/Referenced_Rape/Non-con, Alternate
      Universe_-_High_School
  Stats:
      Published: 2015-09-01 Words: 1645
****** Virgin ******
by NerdySamSays
Summary
     Dean doesn't like taking virginity. But when Cas walks in on him
     masturbating, he might have to set aside that dislike.
Notes
     So this is my first attempt at writing a Destiel fanfiction. Let
     alone a smut... I hope its not to weird... or inaccurate as to how
     gay sex works... I'm not a man myself, so I only know what I have
     read in fanfictions or stories in general...
See the end of the work for more notes
Dean smiled nicely at the beautiful girl who sat next to him on a picnic
blanket, his car hiding them from view from anyone else. It was the first time
in a while any girl at the school had agreed to a date with him, not that it
mattered; all he wanted was a good fuck. And this new girl was just what he
needed. She was very pretty, dark hair and blue eyes, just his type. He knew
his baby brother Sam and his best friend Cas would kill him for this. But it’s
not like the girl is a virgin! She told the most popular girls she had a
boyfriend and they did it on several occasions. But they broke up, so it’s fine
to have sex with her. He’s not taking anything, just enjoying… right? “S-so
Dean, I heard you have a brother,” Sarah blushed, looking away from the green
eyed boy in front of her. Dean merely leaned closer, gently placing a hand on
the girl’s thigh.
“Yeah, but I don’t really want to talk about him,” Dean whispered, “I’d much
rather find out how you’re so beautiful.”
“I-I,” the girl stammered, before all but lunging herself at Dean. They sat
there making out for a few moments before he slid his hand up to her midsection
and pulling her closer. His mouth and tongue easily dominating the less
experienced girl. Carefully pushing her down into a lying position, Dean kept
himself from crushing her as his moved his mouth down her neck, leaving a trail
of hickeys down her neck and chest until he reached her low cut top before
returning to her mouth and leaving her breathless. He only pulled away to ask
her if it was alright. “I lied about having a boyfriend, I'm a virgin,” she
admitted quickly, not looking sure about what they were about to do. Dean felt
himself go white before he pulled himself away from the flustered girl.
“I should get you home before it’s too late,” Dean told the girl, standing up
and dusting his pants off and helping the now confused girl to stand up.
“I-I don’t understand,” Sarah stuttered, watching Dean as he folded the picnic
blanket up and shoved it into the back of his car. “I thought we had
something.”
“Yes, well I don’t like taking girl’s virginity,” Dean muttered, opening the
door for the girl to get into his car.
After ten minutes of tedious silence, Dean had dropped the girl at her place,
not even saying goodbye, and gone to the one place nobody except him, his
brother and Cas knew about. They called it the bunker. When Dean was in the
abandoned bomb shelter he quickly shed his pants and clutched his hard cock. He
had put off screwing that girl; he didn’t want to take something so important
from someone. Not when he had lost it in a less then special way. But the
downside to that; he was now so hard he had spots clouding his vision. Dean’s
hand rubbed down his, in his opinion, massive shaft as he bit his lip and
imagined the babe from his favourite porno, casa erotica 13. Only to yank his
hand off his dripping member when he heard the bunker door creak open. Dean
practically jumped into his pants, the denim rough against his manhood. Dean
sat down at the table he and his brother had brought down there and pretended
he was asleep. Only to be ‘woken up’ by a very disheveled Cas. “Cas?” he
muttered, acting as spaced out as he possibly could.
“Oh Dean, I'm sorry did I awaken you?” Cas said, his very formal way of
speaking making Dean’s erection perk even more. Blushing Dean answered his best
friend.
“Yeah you couldn’t have had waited ten or so minutes to come down here could
you?” Dean murmured, making Cas blush as he realised what Dean was insinuating.

“My apologies Dean, I’ll be out of your hair in a moment,” Cas said, voices
sounding outside the bunker, making Cas’ face to go white.
“Who you running from Cas?” Dean asked, shifting in a manner he would come to
regret because it showed the wet from his pre-cum on his pants.
“Nobody! I-if you want to finish yourself up, I-I’ll look away,” Cas stammered,
his face draining of colour completely as a voice outside yelled out ‘where’s
that fag, I have a stick to shove up his poof arse!’
“Cas who are you running from?”
“My brothers want to shove a stick up my arse to punish me for being gay…” Cas
admitted, now almost crying. Dean didn’t know what he was doing by the time he
had Cas pressed up against the wall of the bunker, his prick rubbing against
Cas’ leg as he pinned the bawling boy against the wall. “If you’re going to
punch me do it quickly, don’t say anything, at least in respect for the
friendship we held once.” Cas began to blubber, only for Dean to shut him up
with a kiss. Cas responded quickly, letting his hand trail down to Dean’s
surprisingly still hard meat. Dean moaned into the kiss as he removed Cas’
shirt and began to work on his pants. Dean began to drag them over to the table
so he could fuck the seemingly enthusiastic boy when he stopped and looked at
Cas.
“Cas didn’t you say you were a virgin, you would have told me if you weren’t
right?” Dean said his normally deep voice husky from the kissing.
“Dean, I am a virgin,” Cas stated, his voice breathless, “But there’s nobody
I’d rather lose it to then you.” He admitted before Dean could pull away.
“B-but what about lube?” Dean tried, already trying to avoid taking something
so precious and irreplaceable from his best friend.
“If you don’t mind getting sticky, there’s some grape jelly on the bench,” Cas
suggested, “and we aren’t that far from the lake where we can go wash
ourselves.” Dean pushed Cas onto the table, his muscles deciding for him. Dean
grabbed the jelly before quickly removed his shirt and his pants. Cas watched
him with lustful eyes before Dean pushed him back onto the table and attacked
his body with his mouth. Leaving a trail of hickeys down his torso until he got
to Cas’ briefs, which he removed faster than he realized he could. Before he
could do anything to Cas’ delicious looking cock, he was being pulled back up
for a kiss, after which Cas whispered to him “I want your prick in me Dean.”
Dean chose to wedge himself in his best friend’s legs, and thumb his entrance.
Cas, blushed as he pushed the jar of jelly over to him, which Dean almost broke
trying to open, only to slather his fingers in the sticky substance and begin
to stretch his friend’s arse to prepare him for his monster cock. Dean started
with one finger before advancing to two, then three before pulling them all out
with a barely audible pop. When Dean looked at the jar of jelly, he found his
friend holding a large glob of it in his hand. Dean almost came then and there
when Cas smirked and moved his jelly covered hand to his dick and lathered it
in the substance. As soon as they locked eyes Dean moved his cock to Cas’
entrance and prepared to thrust in. But instead of what he would do with his
usual sluts, and just go for gold, (when he had a condom on though, like fuck
he wants their STIs) he pushed in slowly, taking the hand of his best friend
and kissing it. When he was fully in he waited till Cas nodded, before he
pulled, almost, fully out and thrust back in at a different angle. He knew to
look for Cas’ good spot. Each time he pulled out he thrust in a different way,
well that was until he heard a loud moan from Cas, to which the said male
slapped his hand over his mouth. The second time Dean hit that spot Cas tried
to hold the moan in. “Don’t hold it in Cas,” Dean said, pulling Cas onto his
lap and thrusting into that spot, pulling a moan from Cas. Dean rocked his hips
as he began to speed his thrust, stealing moan after moan from the boy on top
of him. By the time Dean reached his climax, Cas was panting and flushed. Just
the sight of the boy, no man, riding him was enough to finish him off. “Fuck
Cas!” Dean screamed came into Cas’ arse. The words making Cas to cum between
their chests. As Cas’ orgasm rocked him, and Dean’s finished, Dean pressed his
lips to Cas’. As Cas finished his orgasm, the pair fell over onto the table and
Dean pulled his softening member out of Cas’ butt. As they tried to catch their
breath, the two looked at each other and smiled.
“D-Dean that was amazing…” Cas spoke softly, trailing his finger in a circle on
Dean’s chest. Dean just laughed.
“I’m glad you liked it, I’m glad your first was better than mine,” Dean
murmured darkly. Cas, rather than letting his friend be sad, kissed the green
eyed boy in front of him.
“It’s okay, John is in jail now,” Cas promised, snuggling closer to Dean.
“He’s still a dick, I was ten,” Dean growled. Growling back, Cas sat up and
pinned Dean to the table.
“Dean, he was probably be raped more than anyone else should be when people in
jail found out what he was in for,” Cas told the bitter young man.
“Cas?”
“Yes?”
“I think I might be in love with you.”
“I know.”
“Did you just Han Solo me?”
“Dean?”
“Yes?”
“Shut up.”
End Notes
     was it okay!?! I don't know if it was... please tell me....
     I should also add I don't know if jelly would actually work in this
     instance... it was the first available thing I could think of :O
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