Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/808096.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Porn_RPF
  Relationship:
      "Andrew"/"Cliff"
  Character:
      Andrew_(Male_OC), Cliff_(Male_OC), Nick_(male_OC), Greg_(male_OC)
  Additional Tags:
      Underage_Sex, Underage_Drinking, Anal_Sex, Mildly_Dubious_Consent,
      Dubious_Morality, Dirty_Talk, Age_Difference, Virginity, NSFW_Art
  Series:
      Part 2 of Set_and_Match
  Stats:
      Published: 2013-05-18 Words: 3507
****** The Win ******
by ya3ani
Summary
     Cliff sees Andrew at a pool party and remembers his promise to
     relieve Andrew of his virginity.
"Just don't be a brat like last time," Greg says in good humor, flicking the
left-turn signal and easing onto the highway. "We'll be at someone else's
house."
"Whatever." The cloud over Andrew's head doesn't hurt his brother's good cheer;
it never does. The Maron family is famous in their neighborhood for their
indefatigable charm and pep -- all except for Andrew, of course. Bucking the
family's good name is a point of personal pride.
"'Whatever,'" Greg mocks back. "Ah, 16 and already you're tortured with ennui.
I remember being that young."
"Fuck you," Andrew says evenly, trying not to rise to the bait. "You're only
five years older than me."
"That's a lifetime, my dear boy," Greg says, aping Dumbledore. "A lifetime."
Rolling his eyes, Andrew rests his temple on the window. That morning Greg had
poked his head into his room and asked if Andrew want to come-with to a
friend's pool. Greg was old enough to give no fucks about dragging along his
kid brother wherever he went.
"Who'll be there?" Andrew asks, cutting his gaze to Greg.
"Oh, few of the guys from last week. You met, I think." Greg sends Andrew a wry
look. "Didn't make the best impression on all of them with your temper tantrum,
but I think they got drunk enough after to forget. You'll be fine."
Andrew nods briefly and bites at his lips, twisting his fingers in his lap. He
purposefully doesn't think of who might be there -- not that he knows the guy's
name, or anything.
God. Andrew still doesn't even know his name.
##

                                   [image]
                            Our Brave Protagonists
Cliff's four beers in when a wave of new people arrive. The sun glances off the
water into his eyes while the open sliding glass doors let out a constant blast
of air conditioner behind him. Nick's electric bill is going to be a bitch this
month, but that's not Cliff's problem. He pops a fifth beer and watches a group
of women in bikinis saunter by, their thick thighs rubbing together
beautifully, their soft tummies curving up to heavy breasts.
Introductions take a few minutes but soon enough they're chatting -- the women
are all smart, easy to shoot shit with, and Cliff sips at his beer contently.
The wisp of a boy almost doesn't register out of the corner of his eye. Trying
to be discrete, Cliff looks around again -- and there he is. Andrew. That guy
from last week's kid brother.
Misery follows Andrew around like a cloud, all the more obvious for the
surrounding raucous gaiety. He's picking at his Coke can with a thumb, his
sweet mouth turned down in a frown, his brown hair falling shaggily into his
eyes.
Cliff grips his beer more firmly.
The last two weeks he's fucked his own fist more than once thinking about this
kid, about mounting him and giving him his first good dicking. The memory of
that smart mouth wrapped around his cock, choking on it like a good boy -- but
Andrew doesn't look like he's being the same sort of brat today. He gives off
the feeling of something discarded, his self-pity at his oh-so-lamentable
situation obvious. Ah yes, so awful to be loved by a big brother and to be
under the sun without a care in the world. Cliff snorts and turns back to his
group.
Andrew isn't going anywhere.
 
The first time Andrew sees Cliff, a riotous pink flush starts at Andrew's ears
and burns down his front. The boy's frozen across the pool with his mouth
caught half-open on a straw.
Cliff grins easily and lifts an eyebrow. The glass doors are closed but not
locked, and Cliff lets himself in. Nick and he go way back; the guestroom is
basically his, anyway.
Moments later Cliff has a case of beer and a boy in the room with him, muffled
music and laughter coming in through a cracked window.
"Hi," Andrew says, tongue darting out to wet his lower lip. Having been out in
the sun for so long makes the room seem dark, but even so Cliff can tell
Andrew's blushing.
"Hey," Cliff replies before finishing off his beer and stepping closer. "What's
a kid like you doing here?"
"I'm with my brother," Andrew replies mulishly, his blush turning to an angry
flush.
"Big brother taking care of you?" Cliff smirks and grabs another beer, popping
it open. He hands it to Andrew with no ceremony, pushing the boy to the bed.
Slightly mollified by being offered alcohol, Andrew shrugs. "Yeah." He takes a
hesitant sip of the beer.
Cliff smiles, and Andrew looks away. The self-pity is all gone, now, replaced
by the same general annoyance at the world that first made Cliff want to put
his hands on the kid. Cliff doesn't know much about teenagers, but he does know
indulging brattiness is a mistake. It's one he won't make.
"Do something for me, Andrew." Cliff sits next to him, their thighs brushing.
"What?" asks Andrew suspiciously.
"Drink the beer."
"Um, okay, freak," Andrew scoffs, waving the glass bottle in Cliff's face. "I
already was."
"Not like that," Cliff says softly, wrapping a hand around Andrew's on the
bottle and urging it to his face. "Tip you head -- yeah -- "
Andrew is slowly milking the bottle now, his head tipped back and his hair
brushing his nape, the long line of his neck exposed in the light. Slowly Cliff
puts a palm at Andrew's throat, feeling it contract and expand as Andrew takes
in the beer and swallows it down.
"Look at that," Cliff says into Andrew's ear. "Look at you swallow. Reminds me
of when you swallowed around my cock."
Andrew gasps and chokes, spluttering around the bottle, beer dripping from his
lips and spattering across the guestroom sheets.
Cliff laughs a little meanly and grabs the almost empty bottle away from the
boy. "Not used to alcohol, hm?"
"I can drink alcohol fine --" Andrew coughs and ruins his protest.
"I'm sure you can," Cliff soothes, putting a hand on his boy's back and
rubbing. Andrew shrugs him off with a glare.
"Give me another one," Andrew demands, and Cliff obliges. This time Andrew
throws his head back without being urged, showing off his curved spine and
strong throat, the white skin that covers his carotid artery. By the time he's
finished the beer, Cliff's hands are in Andrew's pants and up his shirt, a hand
urging the bright blue swim shorts down and another plucking at the boy's soft
nipple.
"Your name," Andrew says as Cliff pushes him down to the bed, hulking over him.
"I haven't forgotten," Cliff promises. Andrew's shorts are finally off, his
shirt half-way up his bared chest, and Cliff takes a second to stare. "You
still have your cherry for me, yeah?"
"Duh," Andrew says, glancing down at his own body with an annoyed frown.
"Then you'll get my name," Cliff says easily, putting his hands on the smooth
curve of Andrew's heels.
"I'm not ticklish," Andrew claims, watching what Cliff is doing.
"Not tryin' to tickle you," Cliff replies easily. He moves his hands up to wrap
around Andrew's bony ankles -- they go all the way around. The boy's a skinny
thing, so unlike the beautiful women outside, but Cliff doesn't hesitate for a
second. The flush running fever-like over Andrew's face is worth losing out on
the press of full breasts against his chest, at least for today.
"What do you have, a foot fetish or something?" Andrew challenges from where
he's laid out on the bed, shirt half-rucked up his chest and swim shorts
rumpled, dick already plumping up. So easy.
"No foot fetish." Cliff rubs whorls into the fragile skin on the kid's ankle
bones. "You ready for this? 'Cause if you're not, you need to get back to the
pool."
As Cliff had hoped, Andrew rises to the ribbing. "I'm ready," he says, glaring.
"Right then," Cliff replies shortly, coming over Andrew's body with his own.
"We didn't kiss much last time, hmm? You were too busy sucking my cock down."
Like he hasn't been begging to get fucked this whole time, Andrew goes tense at
being talked down to. "You -- you liked it."
"Yeah." Cliff snorts. He starts working a hand into Andrew's shorts, feeling
the dick that he hadn't even had to touch last time before it went off like a
bottle rocket. "I liked jizzing down your greedy mouth. Gonna do your ass this
time, though."
The gasp Andrew lets out when Cliff fingers his little hole that first time -
- that's something Cliff will treasure long after this day is done. There's no
lube yet, not even spit, so all he can do is press a digit against the baby-
soft skin at the boy's entrance, but Andrew acts like he's being shocked with a
cattle prod each time. Violent shivers run up and down him body, wrack him like
he's already feeling it, too much.
"Are you going to tell me your name?" Andrew's all wide eyes when he asks,
looking less bratty and more sweet at the question, but Cliff can't help being
annoyed. He tries not to show it.
"What's the deal?"
"I -- you -- you fuck me and then tell me your name," Andrew says slowly. His
face contorts as he says it, like he's finally realizing just what kind of deal
it is. Doesn't matter. Kid wants to get dicked so bad he'd beg anyway.
"I take your cherry, then tell you my name," Cliff corrects mildly as he takes
his hand from Andrew's shorts. He stifles any other questions with a long kiss,
thrusting his tongue in the kid's mouth like he's going to thrust his dick in
the kid's hole. Andrew takes it beautifully; it's the best sign. "Take your
shorts off," Cliff urges after their makeout session is done and Andrew is hot,
squirming like a little minnow beneath Cliff.
Red blots of embarrassment rise on Andrew's cheeks as he tugs at his shorts,
finally naked from the waist down.
"And your shirt," Cliff commands. "Wanna see those nipples. Wanna bite 'em till
they bruise, all swollen up."
"Freak," Andrew whispers, but he's pulling his shirt off like a good boy,
nipples pebbling even in the too-warm air of the room.
The sound of splashing and high-pitched laughter floats in through the cracked
window as Cliff tongues at Andrew's nipples for the first time, being gentle to
start with. The touches are driving the kid wild and Cliff almost feels like
he's cheating, it's that easy, Andrew's sweat-wet hair a halo around his head
and his shuddering breaths a perfect invitation. It's a party so naturally
Cliff brought lube and a condom, and he's got both on the bed in a matter of
seconds.
"You ever touched yourself?" Cliff's slicking his fingers up as he asks,
cocking an eyebrow down at Andrew.
"My ass?"
"Your hole, kid. Your hole."
Andrew bites at his lip. "Uh. Yeah. I mean, after you -- um, after that day."
"You thought you'd try it for yourself?" Cliff grins. "See what I meant when I
talked 'bout popping that ass cherry, huh. So how'd it feel -- weird, right?"
Momentarily Andrew looks relieved that Cliff's brought up the strangeness of it
all, the harsh poke of your own finger in that private place for the very first
time. "Yeah," Andrew agrees shakily.
"'S okay, kid," Cliff reassures, running his dry hand up Andrew's leg till he
gets to Andrew's ass and cups the full balls there, lifting them up so Cliff
can glimpse the tight little hole he'll be taking. "Your mouth was greedy and
your ass'll be the same. You just need someone to show you how it's done."
"And you're that person," Andrew asks, disdainful eyebrow lifted. Cliff wonders
how many times Andrew practiced in the mirror to get that right. It's cute,
even if it makes Cliff want to spank him.
"I'm that person," Cliff confirms, and before Andrew can give him any more lip
Cliff's circling the boy's entrance, finger a pulsing movement over the skin
there. Andrew sighs sweetly and Cliff smirks. "See what I mean? You'll like it.
You'll love it."
The next few minutes are syrupy slow, Andrew opening up steadily, groaning at
each finger Cliff adds. The room's hot as a sauna and Cliff wants to turn on
the fan but he can't risk breaking the lull that Andrew's deep under now -
- Cliff is patient, but he's not a saint. At three fingers Andrew's eyes
flutter shut and open, his hand coming to Cliff's chest to weakly push there,
as if he doesn't know whether he wants it or not.
Cliff hushes down at him. "Be good, now, Andrew, not a brat. You take these
fingers and get all loose for me, you hear?"
Like that Andrew goes slack, head lolling on the sheets. Cliff curses softly -
- did the kid just drift into subspace?
"Hurry up," Andrew suddenly demands, eyes black with lust but still clear, and
Cliff takes a relieved breath. Thank fuck. That would have turned into
something messy -- and not messy in the good way.
"'You're ready." Cliff pats the kid's thigh fondly, then hitches him up and
flips him over so quickly Andrew doesn't have time to cry out.
Soothing a nervous virgin isn't too difficult, when it comes down to it, but
Cliff isn't feeling very nice today and Andrew brings out the worst in him.
That's the only reason he picks his dick up and smacks it on Andrew's hole, fat
head making the kid jump. Andrew protests and cranes his head back, but Cliff
puts a hand on the boy's neck and encourages him to present.
He does it like a natural, folding till his chest is on the bed and his legs
are splayed wide apart, hole glistening and ready. Cliff hushes down at him and
thumbs at his cock, guiding it towards the boy's furled entrance. A yelp fills
the air when Cliff pops into that cherry ass, Andrew's muscles tightening up
too late to stop anything.
"Ow, ow, ow," Andrew's whispering into the pillow, shaking a little and rubbing
his face into the fabric.
"Don't cry. You're fine."
"'m not crying," Andrew says in a broken voice. He's shaking.
"God, you're doing so good." Cliff can be nice. Or he can try. "Look so good,
feel so perfect."
"Fuck off."
Cliff laughs hoarsely and dicks the kid the rest of the way, three more inches
all at once. "Fucking brat."
Andrew wails.
Cliff lines his front up with Andrew's back and whispers into his ear, "Want me
to pull out?" It's a long second before Andrew shakes his head, rising to the
challenge like the fool-hardy teenager he is.
It's all good for Cliff, though, and he kisses the back of Andrew's neck and
starts to pull out for the first time, watching the boy's hole cling to his
cock.
"Your cherry feels so good," Cliff groans, snapping forward on the next stroke,
loving the feel of Andrew's trembling body giving way to his own. For a few
minutes Cliff is selfish, taking from the kid's body as much as he wants,
gorging himself on view of the kid's round ass and new flesh, leaving little
hickies all over Andrew's back. A tshirt will cover them, but Andrew won't be
swimming anytime soon.
Eventually Cliff lowers a hand and starts to jerk his boy off. The cock in his
hand is half-hard but leaking, and Cliff jacks it slowly, loving the way Andrew
ripples with it under him.
"I'm Cliff," Cliff says on a particularly cruel tug.
"Wha...?" Andrew's gone, eyes closed and mouth open, spit forming a wet spot on
the pillow.
"Remember our deal, kid? I tell you my name for first chance at your hole."
"Oh," Andrew replies, eyes half-opening. "Cliff?"
"Yeah, baby, Cliff." Cliff thrusts once, long and slow. He watches Andrew's
eyes flutter. "Say my name."
When Andrew doesn't immediately obey, Cliff stops jacking him and holds the
boy's balls in a hand.
Andrew whines deep in his throat. "Cliff," he begs, and Cliff gives the
pleasure back to him.
"Say 'please' for me," Cliff whispers.
"Please, please." Andrew fists his hands in the bedspread and humps back
against Cliff. Cliff's being careful; the bratty side of Andrew's given way to
the slutty, overwhelmed side for now, but they've got to work up to the rest of
this.
"Now say 'please Cliff, I want your dick.'"
Again Andrew refuses at first. This time Cliff pulls out of the kid's ass,
silently promising his dick it'll be back in that wet clench soon enough. He
teases the boy's hole, rubbing there until Andrew gives in with a puppy-like
growl.
"Please, Cliff," Andrew takes a deep breath, "I want your dick."
"Good boy," Cliff praises, and slides back in. Andrew sighs. "Now for the last
one. 'Please Cliff, fuck your slut.'"
"I -- I'm not saying -- " Andrew's refusal is interrupted by two fingers
stuffing his mouth. Cliff bends down close.
"Say it for me, Andrew. I know you'll like it once you do." Sliding his fingers
out of Andrew's mouth, Cliff waits.
"Puh -- please, Cliff -- " Andrew's breathing hard now, glaring but moaning as
Cliff circles his hips, " -- fuck your slut."
Fuck, yes. "Jesus, kid, Jesus." The next ten minutes don't even happen on
planet Earth, that's how good it is, how amazing it is to bend this boy over
and have him parrot back anything: I'm your slut, please fuck me, I'm your
slut, please own me, over and over until Andrew's believing his own words,
getting over himself at last.
"Want me to come on your face?" Cliff grunts out and Andrew takes a second to
think and then nods.
The hole around his cock gives Cliff up with extreme prejudice, gaping open for
a moment like it wants Cliff to conquer it again. It's okay, though; Cliff will
be back. He strips off the condom and watches Andrew, shivery, slowly roll onto
his back. Cliff climbs up his body and aims his dick right at Andrew's face,
jacking it fast.
"Mouth open," Cliff demands. There's only the smallest bit of mulishness left
in Andrew when he complies, and Cliff's come on his face washes even that away.
The obedience makes Cliff's balls tight, and watching the kid take a load on
his face is exquisite, like a fucking painting in a museum.
Propped up on the pillows, his dick hard and wanting, Andrew slowly licks and
swallows the come around his mouth. There's some on his brow and cheeks, and
Cliff thumbs it into the boy's mouth, watching him suckle.
"Cliff," Andrew says after he's as clean as he's going to get. He's staring at
his poor little cock. "C'mon, touch me."
With a wicked grin Cliff bends and sucks Andrew down, earning a stream of
watery come.
In the aftermath Andrew seems confused, but too content to be upset about any
of it.
"How's your hole?" wonders Cliff.
"It's fine," Andrew says quickly.
Cliff brings him close and kisses him softly. He can see that he might have
pushed a bit hard, earlier, and he'll need to wind Andrew down. Andrew gives
him a few kisses but then pulls away. "What're you doing?" he asks, mouth
pulled into a frown.
For the first time, Cliff feels less than omniscient. "Kissing you."
"But why." Andrew pulls his knees up to his naked chest. If he knew how young
it made him look, he probably wouldn't. "You took my cherry, already."
Ah. Of course. Teenage self-worth was notoriously fickle, wasn't it? One part
of Cliff finds itself annoyed at having to coddle Andrew, but the other is more
patient -- and knows that if this is going to be repeated, he'll have to handle
the kid's pride gently.
"I did," Cliff says. "You liked it, right?"
Andrew nods slowly.
"So what's wrong?"
"Nothing," Andrew says, shrugging jerkily, like he's still not completely in
control of his body.
A sudden knock on the door tears them further apart.
"Yeah?" Cliff asks hoarsely.
"One of the girls left her shirt in there and she's going home." It's Nick's
voice. "Can you grab it?"
Looking around, Cliff finds the shirt and cracks the door, handing it off to
Nick, who gives him a lecherous smile. Cliff huffs and shakes his head,
smiling, before he closes the door right in Nick's face.
"So." Cliff starts pulling on his clothes. "How 'bout this. I give you my cell
number, and when your body starts missing me, you can give me a call, hmm?"
Andrew follows Cliff's nonchalant lead and grabs his swim trunks. "Whatever,"
he replies, back to his bratty ways. "I might."
"Next time I'm getting my mouth on those nipples and sucking till you scream."
Cliff smirks. "I'm gonna go make nice with your older brother, now."
Cliff gives it less than two weeks before he's balls deep again.
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