
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4910038.
  Rating:
      Explicit
  Archive Warning:
      Rape/Non-Con, Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Dean_Winchester, Castiel, Sam_Winchester
  Additional Tags:
      Angst, Hurt/Comfort, Prostitution, Underage_Sex, Rimming, Riding, Blow
      Jobs, Anal_Sex, Anal_Fingering, Underage_Prostitution, John_Winchester's
      A+_Parenting, Teen_Dean, Past_Rape/Non-con, Past_Abuse, Dream_Sex, Angel
      Mojo, Established_Relationship, First_Time, Topping_from_the_Bottom,
      Praise_Kink, No_Refractory_Period, Virgin_Dean, Loss_of_Virginity
  Stats:
      Published: 2015-10-01 Words: 7743
****** Each Act is Virgin, Even the Repeated Ones ******
by Jessia
Summary
     Sam walks in on Dean and Cas having sexytimes in the bunker and
     freaks out thinking Dean is under a spell. This leads to an awkward
     discussion of Dean's sexual past, and then Cas comforts his angsty
     hunter.
Notes
     Please see end notes for clarification of tags if you are uncertain
     about any of them. Things get graphic, so please only proceed if
     that's something you are comfortable reading.
     Also note that past tense = the present, and present tense = the
     past. Because I'm evil.
     Title is a quote by Rene Char.
     Thanks go out to my best friend and awesome beta, Teatimelady.
See the end of the work for more notes
Sam couldn’t believe he’d gotten all the way into town on his grocery run
before realizing he’d left his wallet back at the bunker. He was still rolling
his eyes at himself as he pushed through the heavy front door, when a low sound
made him stop short.
He listened intently for a few moments and heard it again – a pained moan.
Hunter’s instincts on high alert, Sam pulled his gun and silently made his way
down the stairs. Soon he could hear what sounded like a struggle coming from
the library.
Rounding the corner, the younger Winchester couldn’t believe his eyes. Dean had
their resident angel pinned to the library table, attacking him and ripping his
clothes off as Cas struggled to fight him off.
Without another thought, Sam strode across the room and dragged his obviously
cursed brother off the angel. Both Dean and Castiel stared at him in shock as
he forcefully pinned his older brother to the wall.
“What the Hell, Sammy!?” Dean demanded. The blond’s shirt was torn from the
earlier tussle, and his belt and fly were hanging open.
Sam ignored his outraged brother in favor of checking on his friend. “Cas, are
you okay?” He glanced over his shoulder to find the angel sitting up and
scooting off the table with a confused look on his face. He hiked his slipping
slacks back up his slim hips and pulled the torn halves of his dress shirt
together to cover himself as he moved towards the brothers.
Sam held out a hand to pause the angel’s forward movement. “Wait, Cas. Maybe
you should stay back until we can figure out what curse or hex Dean has on
him.”
“What the fuck are you talking about, Sam? I’m not cursed! Or hexed! Or
anything else except about to kick my baby brother’s ass for cockblocking me!”
Dean fumed.
“Exactly!” Sam declared. “What’s wrong with you that’s got you attacking Cas!?”
“Attacking?” Dean seemed at a loss for words.
The angel laid a palm on the younger Winchester’s shoulder, gently pulling him
back to let Dean away from the wall. “Sam, Dean wasn’t attacking me. His
actions were quite welcome,” Cas admitted sheepishly.
The tall man opened and closed his mouth to speak a few times before he shook
his shaggy head to clear it. “Well, okay. But something’s still wrong! Dean,
you’re totally straight! You’ve never had one bit of interest in guys!”
“Do you know how your brother lost his virginity, Sam?”
Sam looked from the now glowering angel to his brother with a look of ‘well,
duh’ on his face. “Of course I do. You took Jenny Thomas to that make out spot
in the Impala at the end of your sophomore year,” he stated with certainty. But
that confidence began to fade as Dean refused to meet his eyes, and Castiel
slowly shook his head.
“No, Sam,” Cas replied gravely.
Dean looked to the angel with pleading eyes. “Cas, don’t. Please.”
Castiel’s stern features softened slightly as he turned to the older
Winchester. “I can tell him if you can’t,” he offered.
Dean seemed to deflate as he sat down heavily into a chair. “No, I’ll… I’ll do
it,” he relented, but he refused to meet either his or Sam’s eyes.
“You remember the first time Dad went AWOL on us?”
Sam nodded even though Dean wasn’t looking at him. “Yeah, the summer I was
eleven. He was supposed to be out hunting for a month, but he didn’t come back
for three.”
“Yeah, that’s the one,” Dean confirmed. “We began running out of money around
week six. I started skipping meals here and there and trying to find other ways
to save so I could be sure we’d have enough to stay in the motel. Even that
only helped so much-”
“You stopped eating,” Sam interrupted. “You came down with something, and
always said you weren’t hungry. You lost a bunch of weight… You looked
terrible. Wait, are you telling me you weren’t sick? Did you starve yourself,
Dean!?” Sam demanded with genuine concern and a bit of anger.
Dean sighed and seemed to shrink into himself. “No, Sammy, not exactly. Not on
purpose anyway…” The hunter rested his elbows on the table in front of him and
leaned forward until his face was hidden in his hands before he continued. “I
tried everything I could think of to earn extra cash, I really did. The local
body shops didn’t believe a 15 year old had the skills to work on cars, no one
would hire a kid too young to legally work, and I wasn’t even close to passing
for 21 to get into bars and hustle pool. I had to do something,” at this Dean’s
voiced cracked, and he had to pause and just breathe for a moment.
His brother’s uncharacteristic behavior was starting to worry Sam. “Dean?” he
asked tentatively.
The older man let out a long breath before speaking again. “There was only one
other thing I could think of. I knew if I hung around outside the right bars…”
he trailed off for a moment. “I really didn’t think it would be a big deal. I
mean, I’d been interested a few times before… A couple hours, a couple guys and
I’d have enough for us to eat for the next few days.”
Cas, who’d stood silently behind Dean’s chair this whole time, watched as a
dawning horror began to spread across the younger Winchester’s face.
“The first one wasn’t so bad. He was good looking enough, and I didn’t really
mind going down on him,” Dean admitted.
He’s only been outside the dive bar for about twenty minutes before he sees the
blond surfer-type checking him out. Dean is in his tightest pair of dark wash
jeans (the ones that make his ass look amazing) and a snug-fitting white tank
top; he knows that showing off his wide shoulders and hunting-toned arms helps
him look older than he is. His hair is tousled purposefully, and the black
metal chain around his neck hits his collar bones just right.
He’s nervous as hell, but leans one shoulder against the brick wall beside him
to hide it as the older man approaches him. “Hey, there,” the man says in a
friendly tone as he moves in close to Dean. He’s not yet up in his personal
space, but he’s definitely closer than propriety would normally allow. “Aren’t
you just the prettiest thing?”
A lazy smirk spreads across the teen’s face, and he cocks his hips out
invitingly. “Aren’t I just?” he replies with a wink.
This earns him a chuckle from the surfer-dude, and he relaxes marginally. It’s
going pretty well so far, he thinks to himself. The guy is fairly handsome –
shoulder-length tousled hair, warm brown eyes, angular jaw, and a kind smile
that shows off perfect white teeth. His heartbeat picks up and his body heats
in a pleasant way as the man leans in until their bodies are just barely
brushing, and he runs the back of one finger gently down the side of Dean’s
face letting his palm come to rest against the side of the teen’s neck.
“Are you looking for some company?” Dean asks him, tongue darting out to lick
his lips.
He watches as the blond tracks the movement and those brown eyes dilate. “Mm
hm,” he manages as his lips descend on Dean’s, his tongue easily swiping into
the teen’s mouth through his parted lips. The kiss is passionate but languid,
the older man exploring as his body presses Dean’s backward into the bricks.
The blond is half-hard, but Dean’s teenage libido has him rock hard in mere
moments. When the older man pulls back, Dean can’t help the choked-off noise
that escapes his throat. “That mouth,” he trails off thoughtfully. “I wonder
what it would take to get that mouth around my cock…?”
Dean grins, pupils blown and an excited flush across his cheeks. “Twenty and
it’s all yours,” he purrs. Without breaking eye contact, the blond reaches into
his back pocket and holds up a $20 bill between two fingers to show Dean before
he slips it into the boy’s pocket, sliding his fingertips along Dean’s length
as he pulls his hand out. Dean reins in a full body shudder, guiding the man
around the corner into the alley and dropping gracefully to his knees.
The man unbuckles his belt while Dean works down the zipper, and then he
reaches in to pull him out of his boxers, and suddenly Dean has his first cock-
that-belongs-to-someone-else in his hand. His eyes widen marginally and the
nerves try to reappear, but then he glances upward through his long lashes and
the lust combined with kindness he sees in the other man’s face is enough to
settle him again.
He begins with a tentative lick to the head, salty precome spreading across his
tongue. It’s strange but not terrible, so he laps at it for a few moments
before swirling his tongue around the crown. He hears encouraging noises, so he
begins to experiment. He has absolutely zero practical experience with this –
either giving or receiving – but a life lived hopping from one cheap motel to
another means he’s seen plenty of porn from which to draw inspiration. He sucks
hard on the head, earning a groan. Switches to kitten licks on the frenulum,
resulting in soft sighs. When he takes the blond down as far as he can go
without warning and begins bobbing enthusiastically, he elicits a gasp that
echoes in the alleyway.
The man above him leans forward over Dean just enough to brace himself with a
hand on the brick wall. His other hand slides into Dean’s hair, just touching
and guiding, not pulling. Dean’s pretty proud of the continued litany of sounds
he’s wringing from the blond, and he continues his slide up and down the man’s
cock, trailing his tongue along the underside with every drag out and sucking
firmly with every thrust back in. When the older man’s breathing is down to
harsh panting and continuous groans, Dean grabs his jeans-clad ass with both
hands and lets just a hint of teeth into his actions, and it’s all over. The
blond comes with a wail in a hot gush down Dean’s throat without warning, and
the teen instinctively swallows in surprise.
He pulls off gasping for air as the spent man grips the brick wall for long
moments. He stands when the older man tucks himself back in and refastens his
pants. “That was fantastic,” he whispers breathlessly before dragging Dean in
by the back of the neck for a filthily thorough yet brief kiss and walking away
without a look back.
“Got 20 bucks outta it, and I was feeling pretty cocky.” A mirthless grin
flashed across what little was visible of his face for the briefest of seconds.
“The next guy wasn’t nearly such a looker, but I figured ‘What the hell?’ easy
money.” Dean huffed out a pitiful parody of a laugh. “Easy…”
The bald middle-aged man would not have been Dean’s pick for a casual hookup by
any stretch, but this is business, so Dean accepts his stuttering invitation
into the alley. Sweaty hands slip and fumble on the fastenings of his belt and
slacks, but he manages to free himself eventually as Dean lowers himself to the
ground. The teen is surprised to find the slightly overweight man fully hard
given how nervous he seems, but he doesn’t get much time to process the thought
at all.
Before Dean can lean in and get to work, the man grips his face hard, forcing
his jaw open for him to shove inside all at once. The teen manages to gasp in
just a bit of breath around his sudden mouthful, but exhales it forcefully only
seconds later as the man’s whole body surges forward bashing the back of Dean’s
head painfully against the brick wall. His vision swims momentarily from the
knock, but he isn’t given any chance to gather himself before the man is
thrusting in and out of his mouth quickly and viciously.
He chokes every couple of thrusts as the cock is rammed into the back of his
throat, and the tightening muscle causes the older man to groan obscenely and
start a tirade of humiliating words. “Yeah, choke on it, you little slut. You
just can’t get enough cock in that fucking mouth, can you?” Dean’s eyes begin
to water with the combination of pain and lack of oxygen, but the pleading look
in his face when his eyes find those of the other man just seems to encourage
more abuse.
The man continues to pound Dean’s face, pausing every now and then to hold the
boy in place with his nose crushed into his pubic hair as his length ceases all
of the teen’s ability to breathe. As the edges of Dean’s vision begin to dim,
he starts to panic, trying vainly to pull back but stopped by the wall at his
back and the large hand now closing around his throat. He’s full on crying now,
sure that he’s about to die in some back alley and leave Sammy all on his own.
But the choked sob Dean releases just before everything goes black seems to be
just the thing to push the older man over the edge, bitter seed flooding his
mouth and spattering his face as the man lets him go to collapse to the ground.
Dean vaguely registers more insults and jabs as the man resettles his clothing
and tosses some crumpled bills to the ground a few feet away. He notices the
man laughing as he crawls to the money and pockets it, but he’s staying focused
on not puking right now. Finally he hears the man walk away as he brings his
hand down from the back of his skull to find his fingers coated in blood.
“He was - rough. He liked when I choked, and he held me down on him until I
couldn’t breathe before he’d pull back. He called me names, and made fun of the
tears streaming down my face. When he was done, he laughed at me gagging on his
cum and threw the money down where I had to crawl for it. I don’t even think he
gave me the full twenty; I never remembered to count it. I made it back to the
motel room before I threw up. You were still asleep, just like I’d left you, so
I took the hottest shower I could stand and brushed my teeth for half an hour
before using half a bottle of mouthwash. I swore that I was never doing that
again, but the next morning when I got back from the store and pulled out your
favorite cereal… Your face just lit up, Sammy. I knew it would only be a day or
two before we’d be out of money again, and we had no idea when, or if, Dad was
coming back… So I went out the next night and the next night and the next
night.”
Sam’s voice was barely more than a whisper, “You started looking tired all the
time. And you said you didn’t want to eat because you felt nauseous.”
“My stomach couldn’t stand the thought of eating the food, knowing what I’d
done to get it. It was enough for me that you weren’t going hungry, and I’d be
able to pay the motel bill. But I had to stay out longer to make any decent
amount of money. When we still hadn’t heard anything from Dad a couple of weeks
later, I started to get really nervous about what we were going to do if he
never came back. I’d gotten on speaking terms with some of the other,” Dean
paused and gulped audibly before forcing out the next word, “whores. They kept
telling me I could earn more if I’d do more than blowjobs. I resisted up till
that point, but if Dad wasn’t coming back I needed to suck it up and do what I
had to.”
Sam had remained standing so far, but now collapsed into another chair, a
barely-heard broken ‘no’ escaping his lips.
“It was awful,” Dean confessed.
The scraggly ponytail and cut-off sleeves should be the first red flag, but
Dean is determined to do this before he loses his nerve. The preliminaries are
quick and minimal, Dean naming his price and the guy dragging him into the
alley.
Dean thought it would start with some kissing or at least a blowjob, but he is
so wrong. Without a word, ponytail-guy shoves the teen face-first into the
bricks and yanks his jeans and boxers to his knees. He kicks Dean’s feet as far
apart as they’ll go, and his belt buckle clanks as he undoes his ripped jeans.
Before he can process what’s going on, Dean feels a blunt pressure at his hole,
and he begins to protest as he realizes that Mr. Ponytail isn’t planning on any
prep. “Wait, no no no…” his words cut off in primal scream as the man’s large
cock forces its way inside Dean’s dry, virgin hole.
The breath is forced out of his lungs by both the weight of a heavy body
slamming him into the wall and the agonizing stabs of pain that shoot up his
spine with every thrust. It feels like he’s being torn apart from the inside,
and he struggles to gasp air to form words. “Please!” he begs. “Stop,please!”
The teen’s pleading draws a chuckle out of the larger man, and his hands grip
bruises into the boy’s hips as his thrusts increase in both speed and force.
Dean struggles harder when he realizes that the wetness he can now feel sliding
down his thighs is his own blood, but the guy just pins him more securely with
a forearm pressed across the back of his neck. The teen cries angry tears over
being unable to stop some dumbass rapist trucker when he’s faced down and
killed things that would probably scare the piss out of the guy.
After what seems like forever, the guy grunts and spills himself inside Dean,
and the teen takes the opportunity to elbow the man as hard as he can in the
gut forcing him backward, his limp penis pulling out painfully with a sickening
squelch of blood and come. He growls in pain before kicking the back of the
boy’s knees causing him to collapse to the ground, and Dean is really thankful
he insisted on his money up front.
The man walks off cursing, leaving Dean struggling to stand and right his
clothes with shaking hands.
“I turned the shower to scalding and scrubbed until my skin was raw. Then I
just sat in the tub until the water ran cold.”
Sam could hardly speak now, but he forced his words out anyway. “I found you
there. The water was freezing, and you were so out of it. You mumbled something
about having a fever.”
“Yeah, you bundled me off to bed and played nursemaid until I felt better a few
days later.” Dean couldn’t help the affection that crept into his voice at the
memory of his baby brother devotedly caring for him. He quickly turned somber
again. “It was the worst 20 minutes of my life, but I made what normally took
three or four hours to earn. It got easier, if not more pleasant. I learned to
prep myself before going out to minimize the pain and damage. I could usually
get them to agree to a condom, but not always. I worried about catching
something, but I couldn’t see where I had any other options. I made as much
money as I could and stashed away what wasn’t used for the room or food.
Finally Dad showed up, and I could stop going out. I kept the saved money on me
at all times, so when Dad pulled another disappearing act the next summer, I
was able support us off my savings. The times he vanished on us after that I
was old enough to get honest work or to get into the bars to hustle pool.”
“Oh, God, Dean. I’m so sorry. I didn’t know how you kept us going when Dad
split.” Sam looked stricken.
The older man finally looked up at the tone of his brother’s voice. “Sammy, no,
it was not your fault. I didn’t want you to know. I was very careful so you
wouldn’t know,” he reassured.
Sam’s brain finally picked up on something Dean had said earlier. “Wait, you
said you’d been interested in guys before that?”
“Yeah,” Dean confirmed.
“But not after? I mean, you’ve always been pretty vocal about being straight.”
Dean sighed. “I… looked,” he admitted. “But I never tried anything. I couldn’t
ever bring myself to trust someone that way after everything.” A small smile
crept onto the hunter’s face, and he ghosted his fingers over those of the
angel that had found their way onto his shoulder at some point during his
painful revelations. “Until I realized that I had the only person I could trust
with my soul let alone my body right in front of my face.”
Sam smiled at that, and Dean thought he looked fairly close to tearing up like
a girl as he said, “I’m really happy for you, Dean. And Cas. Sorry about the
freak out.”
Dean submitted to his brother’s manly hugs for a moment before shoving him off
playfully. “Yeah, yeah. Thanks, Samantha,” he groused with affection.
The younger Winchester rolled his eyes at the long-familiar insult. “Well, the
whole reason I interrupted you guys was that I forgot my wallet on my grocery
run. I’m gonna go grab it and head back into town.”
After swinging by his room to retrieve his wallet, Sam passed back by the
library, pausing to throw over his shoulder, “But let’s agree to no more naked
times in the public areas, huh?”
“I make no promises, Bitch!” Dean called to his brother’s retreating back.
“Jerk!” echoed back over the closing of the outer door.
Yeah, they were gonna be fine.
Dean turned to the angel behind him looking wrung out. Cas pulled Dean into his
arms, and the blond wrapped his arms around his waist. “Are you alright?”
Castiel inquired softly.
He pulled back but stayed in the circle of the shorter man’s arms and gave him
a crooked smile. “Yeah, just tired.” He pressed a gentle kiss to the angel’s
lips. “Think we could go take a nap?”
“Of course, Dean. Anything you want,” Cas agreed.
They retreated to Dean’s room and stripped down to boxers for Cas and boxer
briefs for Dean before arranging themselves comfortably in the bed. Cas lay on
his back with Dean tucked up to his side using his shoulder as a pillow. The
angel enjoyed the simple press of skin to skin as his hunter’s breathing evened
out.
Just when he thought the blond had dropped off to sleep, he heard an
uncharacteristically timid-sounding, “Cas?”
“Yes, Dean?” he inquired softly.
“I wish you’d been the first,” he confessed in a rush.
Cas used one hand to gently tip Dean’s face up to his own. “I don’t.” At Dean’s
confused and almost hurt expression, Castiel was quick to continue. “Though I
would spare you the pain you went through, you would not be the man you are
today without your past. And I am quite fond of the man you are today.”
That earned him a brief sleepy kiss before the hunter settled back down and
drifted off.
Castiel enters Dean’s dreamscape to find himself across the street from a run-
down looking bar. He spots Dean amongst the few people milling about the
entrance to the place, and the sight is almost surreal. He’s shorter than Cas
now, only reaching as high as his nose. He’s muscled, but in the way of lanky
youths instead of the compact strength the angel is accustomed to. His hair is
so much blonder that when combined with the roundness of his face and the lack
of creases at his eyes, the hunter looks unbelievably innocent.
That air of innocence attracts attention from more than just Castiel, but the
angel deflects the path of the miscreant with a ponytail away from Dean and
approaches in his place. Those green eyes are just as mesmerizing looking up at
him as they usually are looking down, but Cas is gratified to note that the
young man seems just as caught up in his blue gaze.
The angel reminds himself why he’s here, and steers things back on track. “How
much for the night?” he quietly rumbles, and watches the teen’s eyes dilate
slightly at the sound.
“Uh…” is all Dean manages, as it seems he hasn’t thought this far ahead. Cas
pulls out a roll of bills that has to be at least three or four grand, and the
boy is momentarily stunned. “Wow. Yeah, you got someplace for us to go?”
It’s no time at all before they’re standing inside a room at the crummy yet
clean little motel a couple blocks away, the décor on par with that of the
motel room Sammy is sleeping in across town. An attack of nerves seems to hit
Dean, and he combats it by practically launching himself at the brunet.
Castiel allows unsteady hands to shuck the trench coat from his shoulders, but
stills the shaking fingers that begin to fumble with his tie and shirt buttons.
He cups the young man’s face with one large hand bringing their eyes to meet.
“Hey,” he says gently, “There’s no rush…”
Dean seems to relax a bit at this. “Okay…?”
“Castiel,” the angel offers.
“Okay, Cas,” he can’t help the twitch of a smile at the familiar nickname, “I’m
Dean.”
“Hello, Dean.” The kiss he leans down and gives is sweet and almost chaste, and
Dean just melts into it as their arms wrap around one another. The angel uses
the hand at his cheek to tilt the teen’s head just so, and the kiss deepens.
It’s a pleasant surprise when Dean is the one to lick at Cas’ mouth, begging
for entrance, and he parts his lips willingly as he sinks his other hand into
short blond locks.
Dean’s arms are around the taller male’s waist, fingers clutching the white
dress shirt, while they languorously explore one another’s mouths. Cas slides
the hand from the teen’s face to his hip and pulls their bodies flush,
erections pressing together, as he works his lips down over his throat. The
surprised gasp that melts into a groan makes the angel smile against his skin.
When he bites down gently on the spot between neck and shoulder, Dean’s whole
body shudders, and he rucks the shirt from the waistband of Cas’ pants.
The angel hums in satisfaction when Dean’s hands slip under the fabric and
eagerly begin exploring the planes of his back. Castiel works his mouth back up
to Dean’s lips, and this time he kisses with more heat – he can’t really help
it, Dean in any form just does things to him. This time when Dean starts on the
buttons of the angel’s shirt, his hands are quick and steady, and soon the
garment is forgotten in a puddle on the floor behind them along with his tie.
The hands now sliding up his chest are familiar and foreign at the same time.
Overall they’re the same size, but the fingers are thinner and missing the
years of built up calluses that he’s used to.
He strips Dean’s tee shirt over his head, and the frustrated whine he receives
when their lips have to part makes him chuckle. Instead of diving back in as
the teen clearly desires, Cas works his way back down the other side of his
neck, nipping at a collarbone before continuing lower. The angel goes to his
knees just as his lips close around one of the blond’s nipples, and Dean keens,
gripping tight to broad shoulders. Castiel laves it for a few moments before
switching to the other as his nimble fingers work open the fastenings of the
young man’s jeans. He looks up to Dean’s face and is captivated for a moment by
the way his teeth are sunken into his bottom lip. When their gazes meet, he
quirks a questioning eyebrow while his fingertips slip beneath the waistband of
his jeans and boxers, and Dean nods his head quickly.
With permission granted, the angel slides the rest of the clothing down toned
legs and coaxes Dean to step out of the tangle of them along with his boots and
socks. The sight of Dean before him – flushed, hard, and dripping precum –
makes his mouth water and breaths come faster. He leans forward to give a
single lick across the head, andthis is familiar – the burst of flavor over his
tongue that screams ‘Dean’ in his brain. Castiel is well practiced at this, so
it’s nothing for him to slide his lips down and take Dean whole. The startled,
“Fuck!” from above him is just as gratifying from young Dean as it is from
older Dean.
He hums before swallowing around the length in his throat, and he swears he
hears Dean whine. He starts bobbing his head up and down Dean’s cock, licking
and sucking as he goes. The angel pulls out all the stops; he knows every
little trick that Dean loves – Dean himself taught him, after all – and he uses
all of them.
Cas loves how vocal this Dean is; he allows his moans and gasps to escape
unabashedly in a way it took months to coax out of the older version. The
younger man’s thighs begin to shake, and Castiel pulls his hands down to tangle
in his dark hair, encouraging Dean to let go. His hands clench tightly as he
pulls the angel on and off his dick, fucking his face. Cas groans
appreciatively, and Dean is gone. “Oh, fuck! Cas!” The teen nearly screams as
he comes hard down the older male’s throat, and his knees buckle. It’s only Cas
catching him by the hips and guiding him to the bed that keeps him from
collapsing to the floor.
Dean looks on with half-lidded, pleasure-dazed eyes as Castiel licks stray
drops of his come from his – red, wet, used – lips while ridding himself of the
last of his clothing. He’s still trying to catch his breath when those lips
descend on his own, tongue swiping confidently into the warm cavern of his
mouth, and he can taste himself there.
When the kiss breaks, Cas reaches down to his discarded trench coat and pulls
something from one of the pockets. Dean can’t help the nerves that leap to the
surface once again as the angel climbs onto the bed next to him, bottle of lube
in his hand. His anxiety must show on his face because after another swift
kiss, Castiel is quick to reassure him, “This is for me, not you.”
Dean’s confused for a moment until the brunet arranges himself on his back with
his head on the pillows and spreads his legs wide, weeping erection standing
proud. Cas slicks the fingers of one hand before setting the bottle aside and
lowering them between his thighs. He bypasses his cock completely because he’s
not sure how long he’d last and circles his hole for a moment. He watches
Dean’s transfixed face as he sinks the first finger into himself, and he smirks
when he hears the boy’s breath catch.
As he slowly works lube into his channel, he feels the bed shift when Dean
leans up on an elbow to get a better view. It seems the blond isn’t aware he’s
done so because he startles a bit when the angel speaks. “You can come over
here for a better look if you like,” he rumbles. Cas has no choice but to
chuckle when the teen moves so fast to comply that the sentence is barely all
the way out before he’s settled on his knees between Castiel’s thighs.
Cas’ second finger slips in along with the first, the slight stretch feeling so
familiar, and he sighs a little in pleasure. Dean’s breathing, which had just
begun to settle into a normal rhythm, picks up again as he watches the older
male twist and scissor fingers into his own ass. He feels a flush of heat as he
begins to harden once more. Dean opens his mouth as if to speak, stops,
swallows hard, opens his mouth again… but words don’t come. Green eyes flick up
from the erotic sight to catch blue watching him. “I-“ he pauses uncertainly,
but Cas nods for him to go on. “Can… Can I help?” He asks, almost meekly.
The unrestrained smile Cas grants him eases some of his tension. “Please, do.”
Dean uses the bottle of lube to slick up some fingers and leans forward with a
hand beside the other man’s hip. He slowly works one digit in between the two
Cas already has in himself, and the feeling is strange and thrilling. He didn’t
know it would be this hot or this tight or that he would be able to feel Cas’
moan from the inside. They move together, working their entwined fingers in and
out, and Dean feels as dazed as Castiel looks. When the brunet asks, “Please,
Dean, more,” the teen adds another finger. He watches in awe as the angel’s
hips roll, and his head is thrown back with a loud groan when he grazes over
what must be his prostate.
Dean likes the reaction so much that he rubs over the bundle of nerves again
and again just to watch Cas begin to fall apart. When the older male is finally
able to lock their gazes again, the heat and need Dean sees there is enough to
make his mouth go dry. “Dean, do you want to fuck me?” his voice comes out like
whiskey over gravel, making Dean’s stomach flip. The teen is so stunned by the
offer that all he can do is nod.
Castiel draws their fingers out of his body and places his clean hand on the
boy’s chest. “Lie down,” he gently encourages. Theoretically, Dean knows the
mechanics and logistics of sex, but right now in the moment his mind can only
focus on the lust and need and want coursing through his body. The young man is
very glad that Cas is taking care of things – slicking Dean’s cock with more
lube, straddling his thighs, lining his hole up with his length…
When the angel begins the slow slide down, Dean’s whole universe narrows to the
scorching heat and exquisite tightness surrounding him. As Cas is fully seated,
the teen hears a sound like a wounded animal and suddenly realizes that it’s
coming from himself. The older male is gasping in breath as he adjusts to the
feeling of fullness, but he ignores both as he instead focuses on soothing the
blond under him. Gentle fingers caress Dean’s face and slip through his hair
while he breathes deeply to rein in all he’s feeling.
A few moments later he manages to huff out, “I’m okay.” His voice is so low and
rough that he momentarily sounds like his older self, and Castiel can’t help
but surge forward to plunder Dean’s mouth while Cas’ body shudders atop him. He
finally pulls back and rests the hand not still tangled in the teen’s hair on
his chest. Then he watches sheer pleasure spread across the young face as he
lifts up and shifts back down, setting an easy pace.
Dean is enormously grateful for his earlier orgasm, as the sight and feel of
the gorgeous man riding his cock is still almost too much to bear. He realizes
that his hands have had a death grip on the sheets for the last few minutes,
and he frees them but is at a loss for what to do with them for a moment. He’s
only a little uncertain when he asks, “Cas? Can I touch you?”
“Always,” the angel moans fervently, and he wastes no time sliding his palms up
to explore Cas’ chest, thumbs circling hardened nipples. He lingers there
momentarily, enjoying the pleased hum he gets in response, before he traces his
fingertips over the curves and valleys of the brunet’s toned abs. Eventually,
Dean glides his hands down muscular legs then back up to grasp sharp hipbones.
Dean’s grip molds to Castiel’s form like they are made for one another, and as
far as the angel is concerned, they are. The teen’s hands simply guide at
first, but when Cas shifts his hips just right and Dean’s cock strikes his
prostate, the half-broken “Ah!” that punches out of the brunet’s mouth is just
beautiful.
The young hunter pulls Cas’ hips down harshly, angling that same way and is
rewarded with the same sound, a stream of “Ah, ah, ah!” with each thrust. Their
rhythm turns frantic, Castiel slamming down hard over and over while Dean yanks
him onto his thrusts up from the bed. “Oh, Dean…” the angel moans. The teen
feels fire coiling in his gut as that dark voice seems to scrape over his body,
“Oh God, Dean! Fuck! So good. So… good…”
Dean is stunned when Castiel comes without warning, clenching brutally around
the hardness inside him, pulsing hot ropes of white onto their bellies, cock
completely untouched. The angel continues to move over him, riding out his
orgasm, and the spasms of his ass finally drive Dean over the edge, releasing
his seed deep within the other man.
Cas collapses onto the teen’s chest, and Dean’s arms come around him without a
second thought. He cards his fingers through sweat-dampened hair as they both
gasp for breath and wait for their hearts to slow. Dean feels himself slip out
of Castiel as he softens, and it’s only then that he notices the older man is
already hard again. He squirms a little as his own dick gives a valiant twitch,
and he comes to a decision. His voice is barely above a whisper due to anxiety,
but the angel’s head snaps up so their eyes can meet when Dean murmurs, “I want
you inside me…”
“You don’t have to do that, Dean,” the brunet insists, but the concern and
tenderness in his eyes just makes Dean more certain that it’s what he wants.
The young man cups Castiel’s face with both hands as he brings their mouths
together for a thorough and gentle kiss. They rest their foreheads against one
another, and Dean’s voice is louder and surer when he repeats, “I want you
inside me, Cas.”
The look of awe and borderline-adoration on Cas’ face as he lifts up is making
Dean uncomfortable, so he arranges himself on hands and knees without being
asked to get away from it. He feels Castiel shift around behind him, and he
expects to feel fingers at his entrance. What he doesn’t expect are Cas’ hands
spreading his cheeks apart and the completely foreign sensation of a tongue
sweeping across his hole.
The air is punched from his lungs as that tongue flicks and swirls, and it
takes several long moments for Dean to gasp in another breath. The angel licks
from his entrance down to his balls and back up, and the teen just writhes,
fingers white-knuckled in the sheets, cock beginning to fill once more. Castiel
stiffens his tongue to work it past the rim so he can fuck in and out of Dean’s
hole, and the slight rasp of stubble against that sensitive skin just makes it
that much better.
Cas seems to be enjoying himself if the moans he releases are anything to go
by, and the vibrations travel right up inside Dean. When the tongue withdraws,
it is only to be replaced with one slick finger that slides in effortlessly.
The angel continues licking Dean’s rim as he thrusts his finger for long
moments before adding a second. He scissors them, and any discomfort from the
stretch disappears as soon as he licks his way between them to rub against
Dean’s inner walls. He’s fully hard again, dripping precum onto the bed.
The hunter’s arms give out, leaving him with his chest and shoulders pressed
into the mattress, ass in the air, and he moans in tortured delight. His breath
catches when he feels the third finger go in, and it ceases entirely when
Castiel finds his prostate. It’s only Cas’, “Breathe, Dean,” whispered against
his tailbone that allows him to drag in a ragged lungful of air. Dean keens
with each swipe over that little bundle of nerves, and his body seems to just
surrender to whatever is Castiel’s will.
Cas eases his fingers out and slicks his erection with the extra lube. As he
lines himself up, he twines the fingers of his other hand in the back of blond
hair to turn Dean’s head just enough to catch his hazed emerald eyes. “Are you
sure?” he asks one last time. The teen only nods enthusiastically.
Castiel works his way into Dean in one slow, smooth motion that leaves him
struggling for control. He’s been inside Dean before, of course – but older,
experienced Dean. This Dean is untouched, and that thought kind of blows his
mind.
Dean is trembling beneath the angel, just trying to process the new feeling.
There is no pain – Cas prepared him well – but the fullness and intensity are
overwhelming. When the brunet slips both hands under the boy’s shoulders and
lifts him until his back is flush against Castiel’s chest, the angle of his
cock changes, and Dean releases the most broken noise the angel has ever heard
from the blond.
He leaves one arm holding the teen to his body and works one hand down to
circle his erection, but as soon as he grazes the skin, Dean goes rigid.
“Don’t, Cas. Too…” He can’t finish the thought and breaks off in a whimper.
Fearing he has hurt his hunter, Castiel starts to pull away, apologizing as he
does, “I’m sorry, Dean. I was too rough. It’s too-“
“Too. Good,” Dean grates out, slinging one arm behind him to grip the other
man’s body so he can’t move away. He feels Cas sigh in relief, and the angel
just strokes Dean’s chest and flank soothingly for a while. Finally, the
tension coiled in the teen’s spine releases a bit, and he’s able to beg,
“Castiel, please.”
He can feel the rumble of assent from Cas’ chest roll through his entire body
as the angel’s grip settles on one hip, and he slowly pulls out. The noise Dean
makes when Castiel thrusts back in sounds like he’s dying – but in a good way.
As Cas sets a rhythm, the blond’s head falls back to rest on his shoulder, and
he can only pant like he’s just run a marathon.
Castiel holds Dean in his lap like the precious thing he is as he works inside
him, all the while kissing and licking and sucking at his neck and jaw and
shoulder. He ghosts his lips along the teen’s ear and murmurs, “Beautiful,” but
Dean manages a derisive sound and shakes his head. Cas will not stand for this.
The angel breaks pace and holds perfectly still to get the young man’s
attention. When he can tell he has Dean’s focus, he gives one measured thrust
for each statement. “Yes, Dean, you are beautiful. You are kind. You are brave.
You are selfless.” Cas’ speed increases slightly as he continues vehemently,
“The light of you burns through the darkness. The good in you casts away evil.”
Dean’s eyes are clenched shut as he rides Castiel’s intensifying movement. One
hand grips the forearm banded across his chest to hold him up, and the other
fumbles back to anchor into raven hair. All he can do is hold on and try not to
drown in the pleasure of Castiel’s body, voice, and reverence. Their bodies are
almost slamming together now, and the angel’s voice would sound terrifying were
it not for the words of praise and the clear tone of adulation. “You are
strong. And gentle.”
Castiel is beginning to lose his thread of control, but he presses on,
determined to fill Dean’s soul along with his body. “You are loving. And
loved.” Cas gasps and clutches the blond tighter, “Oh, God , you are loved,
Dean Winchester…” They’re both shaking so hard it’s surprising they can still
cling to one another, but the angel persists. “Your soul is the beacon that
guides me. You are my everything, Dean.”
His voice is little more than a ragged breath when he whispers, “I love you,”
and Dean comes with a wail. His fingers grip Cas so hard it makes even the
angel wince, but the vice of Dean’s ass gripping his cock sends him headlong
into orgasm despite the pain.
Castiel closes his eyes…
...And opened them to meet the confused and shocked stare of hisDean. “Cas?
What the hell?” the hunter asked gruffly, voiced still laced with sleep. He
seemed to contemplate for a moment before coming to a realization. “I remember
my first time. But I also remember it with you.”
Castiel grinned a bit sheepishly. “I told you I couldn’t change the reality of
your past, but there was no reason I couldn’t add another reality to your
memory.” The angel paused, looking worried. “Are you angry? Should I not
have…?”
Dean huffed a laugh and drew Cas’ lips briefly to his own. “I’m not mad,” he
assured. “You just have some crazy ideas sometimes.”
The angel could only shrug at that, and offered the only explanation that
mattered, “I love you, Dean Winchester.”
The hunter rolled his eyes as he settled back down against his lover’s chest
(three rounds of angel-mojo-dream-sex apparently still really took it out of a
guy). “I love you, too,” he paused a beat, “Freaking angel.”
He couldn’t see Castiel’s goofy smile, but Dean knew it was there all the same.
End Notes
     Rape/Non-Con is in the past by OMC's with underage Dean. Dean
     discusses his past as an underage prostitute when he was 15 in
     graphic detail. Cas and Dean have angel-mojo-assisted dream sex with
     Dean as he was when he was 15.
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