All-In: The Side Bet
story series includes depictions and descriptions of gay sex among male
high school students. If that's not your thing or if it is illegal for
you to read this story, then stop. This story is completely made up and
does not depict any real events.
Comments, suggestions, and helpful feedback are welcome. - Send me an E-mail
Ethan - The almost virgin
Dallas - The aggressive bettor
Kevin - The sandwich
Greg - The sex-crazed older brother
Oscar - The reluctant host
Alex - The "secret" bisexual
Tommy - The closeted hottie
Zane - The sexy newcomer
Neil - The innocent little brother
'Calm down. Calm down, Kevin. Don't show any emotion. Why didn't I put
on my sunglasses?' Kevin tried to keep his breathing even and his face
blank. Don't reveal anything. Don't give them any help.
Kevin had made the flush. Just like that. Holding the queen and jack of
spades, Kevin had raised, been called by the usual "calling stations."
Six of the guys were in. He should have raised more. The flop was a
king of hearts, ten of spades, and four of spades. He had both a spades
and straight draw. When everyone before him checked, he raised about as
much as was in the pot. It was risky on a draw, but he felt good and he
was on the button. Wasn't that what Phil Gordon said to do in his book?
In the face of an aggressive raise, the folds came quickly. Thank you
Phil! Kevin could be a risky player, but he didn't bluff a whole lot.
The turn was an ace of spades. He had made the straight, but better, he
had made the flush. And had a chance for a straight flush! But the ace
made him think. If someone had an ace, they only had a pair. No one had
pocket aces, he was sure. Anyway, they'd only have three of a kind, so
that 'd be perfect. The only flush that would beat him was with a king
of spades. Neil checked. Dallas put in a chunk of chips. Kevin knew
Dallas was a 'reacher.' He underbet high pocket pairs and overbet his
draws and bluffs.
Dallas was even better known for his sidebets - non-monetary prizes
that had the loser give up something or doing something embarrassing.
Kevin once had to run through the girl's locker room in his underwear
after losing a bet to Dallas in sophomore year. Greg did a striptease
on the table at Missy's pool party this past August. Tommy had to wear
a sign that said, "I want to suck Dallas Duncan's dick!" everywhere
except school for two days. But since the beginning of the year,
Dallas's side bets had grown a bit more aggressive. This had made for a
lot of the guys not taking his side bets, several embarrassing and
uncomfortable evenings, and one evening they would all never forget.
Three months ago at poker night, Dallas and little Neil had a huge bet
over the Cowboys-Eagles game. The terms kept escalating despite
everyone, especially Neil's brother Greg, trying to contain it. Dallas
had set the terms in advance - loser sucks the winner's dick. Everyone
had tried to talk Neil out of it, but amazingly Neil accepted. Dallas -
both the team and the teen - lost. They all watched in amazement as
Dallas was a man of his word - he got onto his knees, lowered Neil's
pants, and actually sucked Neil's dick in front of them all. That was
fucking unbelievable. Kevin had replayed that scene in his head more
times than he had wanted, but he couldn't let it go. The pure joy on
Neil's face, the sight of his cock in Dallas's mouth were both
Kevin didn't want to slow play his flush. He offered a big raise on top
of Dallas's raise. Neil immediately folded. Dallas quickly called. Did
he have the king of spades and another spade?
Now the river...A harmless four of clubs. Only a king of spades would
hurt him now. And he felt sure that Dallas didn't have it. He'd have be
the biggest pot of the night and command of the game.
Dallas checked. He definitely had him. Dallas always bet big on the river if he had something.
"I'm all in," Kevin pushed his pile into the center. Side
conversations, one cigarette, and several beer bottles froze as
everyone turned to watch. It was a shit load of money in the pot. Maybe
$400. Real money. Money Kevin could use.
"How much you got?" Dallas mumbled.
"I don't know. Count it yourself," Kevin snapped. Was he just stalling for show? Oscar, who was dealing, did the count.
Dallas took some extra breaths for drama. "That is less than half of my
pile. I kinda want get more from you on this killer hand."
"Shut the fuck up Dallas," Kevin snapped. "It's all-in poker. I'm
all-in. So either fold and I'll take the pile or call and I'll take all
the chips when I flip my cards over." Kevin was incensed by Dallas's
arrogance. If Dallas knocked out Kevin, he'd have more chips than all
the others combined. Dallas often won the most on poker night, but
Kevin played tough and wanted to crush him tonight. He had already been
bluffed out of a couple pots by Dallas and wanted revenge.
"Yeah, but I'm sure I have you, so I want to get the most out of this
moment." Dallas was pressing. But if he was bluffing, what did it
matter? Maybe he was just posturing before folding. Kevin looked over
the board again:
King of hearts, 10 of spades, 4 of spades, ace of spaces, 4 of clubs.
Other than the King of spades and another spade, his hand would carry.
Kevin imagined the check mark next to his name as those boring hosts on
The World Series of Poker discussed his triumphant win and Dallas's
"Just call!" Greg shouted. He hated a slow game.
"How about a side wager, K-Dog?" Dallas was staring right at him, but
looked pale and a little nervous. He also used Kevin's hated self-given
nickname from 5th grade soccer.
"What do you have in mind?" Kevin started remembering how happy Neil
looked while Dallas blew him. And why not? Neil was only 15 - and who
didn't want a blowjob at 15? Kevin was 17, with his birthday in two
weeks, and Dallas had turned 18 a couple weeks ago. Kevin started to
imagine the humiliation of Dallas sucking him off in front of everyone.
He'd definitely cum all over his face. He felt himself getting a little
"How about an extra? Whoever wins gets the pot. But whoever loses has
to do whatever the winner says for...the rest of the weekend." Dallas had
a smug, self-important look on his muscular, chiseled features.
"It's only Friday, Dallas. That's long fucking time for you to be..."
Kevin paused, knowing he couldn't initiate the blowjob talk or he'd
sound gay, "...cleaning my house."
"How about just until the game ending time - 1am?" The game always
ended by one if someone hadn't knocked the rest of the guys out. It was
10:43 pm, Kevin noted. The game would be over long before that.
"Anything the winner says?" Kevin wanted the terms clear. If he had
over two hours he could definitely get two blowjobs even. And he could
make Dallas do things with the other guys...no, that'd be too cruel. But
Neil had told him last week that the blowjob from Dallas was still the
only one he had ever gotten. Maybe he'd have Dallas pleasure the boy
again. Kevin laughed a little at the thought.
The tension between Dallas and Kevin was a regular part of the evening
- and made for a more interesting game. As two of the best players,
their feuds, arguments, disagreements, and calls, raises, and bluffs
out of spite made possibly tedious nights into ones with electricity.
It was their unspoken history that especially stoked the fire.
In elementary school, Dallas and Kevin had been the best of friends.
They had grown apart during middle school as Kevin kept playing soccer
and Dallas went out for the football team (and also started getting in
more trouble). It was all still friendly until freshman year. The boys
had gotten into an argument over something trivial. A few nights later,
Kevin, Oscar, and Ethan arrived at a friend's backyard BBQ. Kevin was
excited because he thought he was going to get very physical with his
first-ever really-serious girlfriend, Amy. When the three of them
discovered Amy and Dallas making out (really dry humping) in their
underwear inside the house, the gloves came off. Amy was apologetic and
blamed the beer. Dallas made no apologies. "All's fair in love and war."
Three years later, payback was finally at hand. "Okay, I accept the side bet," Kevin declared.
"Then I call," Dallas pushed in the matching amount of chips. The $600
or so pot was a mess of multi-colored chips. It wasn't the biggest pot
they ever had, but it was the first one with the tension of the 2
participants and the unspecified side bet.
The room was still. Only the buzz of the air-conditioner filled their
ears. Kevin knew this was a crowning moment. A great moment in the
final months of senior year. He just imagined telling his future
fraternity brothers at American University next fall about this night.
Taking in the experience, Kevin looked around the room. It was Oscar's
house because Oscar always hosted their regular Friday night game. They
had been obsessively playing Texas Hold 'Em since middle school. Kevin,
Dallas, Oscar, Ethan, and Greg were all seniors and had known each
other since first grade. Alex was also a senior and had joined their
social group sophomore year. Neil was a sophomore and was Greg's little
brother, but was really cool. Cooler than Greg actually, some of the
other seniors thought. Cooler than my brother, for sure, Kevin thought
of the turd he was related to. Tommy was a junior who had become
friends with Greg as they were both lifeguards and he slipped easily
into circle. Zane, was a friend of Tommy's. He was a junior and was
only at his second game. He was terrible at poker, but seemed friendly
and cool. The seven boys stared at Kevin and Dallas. Except for Zane,
they had all been at the game where Neil won the blowjob from Dallas.
They were all thinking a repeat of that action a certainty.
Kevin flipped over jack and queen of spades.
"A straight!" Neil cried.
"No, a flush," Oscar corrected him.
Dallas had no response. He flipped one card - the ten of clubs - a
pair. So Dallas didn't have the flush. Nothing could beat him. If
Dallas had another ten that was only three of a kind.
Dallas flipped his other card - a four of hearts. Two pair.
"Oh!" guys exhaled. Kevin smiled and began to reach for the chips as he saw Dallas do the same.
"I've got a flush. Beats two pair." Kevin barked.
"I've got a full boat, K-Dog. Fours over tens."
Every eye turned to Kevin. He hadn't even noticed second four on the
board. He had never imagined that anyone would call his initial raise
before the flop holding an off-suit 10-4. And Kevin would have won
until that 4 came on the river and killed him. It was a fair victory -
a suck-out that would have gotten Greg to throw his cards and storm off
if he was the loser. But Kevin tried to keep his frustration,
disappointment, and anger under control. He wanted to maintain class
even though he was ready to scream.
Dallas raked in the massive chip pile and began stacking it before
stopping. "You just got outplayed, K-Dog. And I got a helpful last
card. It happens. Now, why don't you start by stacking all my chips
"Fuck you!" Kevin whispered. "Stack your own damn chips."
"Ummm...we had a side bet, asshole. Now, do what I ask or I'll make it much harder on you."
Kevin closed his eyes. The guys only had two things they held sacred
when they competed in anything: Honesty and Your Word. Cheating was
considered a cowardly way to win anything and in all sports or games,
so they played within the boundaries of the rules. All of them
fulfilled any bet they made. If you bet money, you paid when you lost.
If you bet an action or an object or any other promise, you fulfilled
it. They did a lot of things that involved money in addition to poker:
blackjack, NCAA and NFL pools, big money fantasy sports, and recently
they had begun betting on kids in the Scripps National Spelling Bee
just for fun. They also made small bets like what color sweater Mr.
Monroe would wear today or whether someone could get Mrs. Margolis to
use the word "fart" during class. The bets were usually for money, but
sometimes for things like punches, noogies, nipple twists and the like.
Sometimes for information. Sometimes for stuff. That's how Kevin got
his iPod off of Ethan. And once in a while for something else. The
blowjob was the only physically sexual thing Kevin could remember
anyone ever betting before. But that was going to change.
Kevin opened his eyes.
"Come on, K-Dog," Ethan encouraged.
"You know I fuckin' hate that nickname, E-thin."
Ethan was skinny as a board and tried everything to gain weight and
muscle without success. He likewise hated his nickname given in middle
"Just do it," Greg pushed.
With a deep breath, Kevin walked over to Dallas's seat and stacked up
his chips. For the next ten minutes, he was responsible for getting
drinks, counting out the chips, pushing them in, and raking them in as
Dallas easily knocked out four other guys. The remaining three guys had
practically nothing and on the next hand two hands, Dallas collected
their cash too. It was $100 buy-in tonight, so Dallas had won $800 off
the other 8 guys.
"Well that's it, huh?" Kevin offered brightly as he started walking to
the stairs. "Nice game. Good job Dallas. Lucky river. See you all
"Fuck that," Dallas's voice was severe and cold. "I've got until 1am -
that's almost 2 hours." Kevin turned to other guys for support, but
they all agreed the bet had been until 1am, not until the game actually
Kevin stared at Dallas coldly. Dallas was a muscular guy. He worked out
all the time, played on the football team, and had also wrestled in
middle school. He was considered hot by most girls, of average
intelligence, and treated women without much respect. Seeing this 6'2"
muscle mound blowing skinny, 5'6" Neil was particularly amusing for
"Let's start by you licking my shoes," Dallas commanded.
Kevin swallowed deeply. This was going to be the most miserable two
hours he was sure. But he had made the bet and had to comply. He'd have
humiliated Dallas if the cards had been slightly different, so he
shouldn't really be a hypocrite.
Kevin dropped his 6' frame to the floor and pulled his
in-need-of-a-haircut sandy brown hair out of his eyes. Dallas was
wearing cowboy boots, living up to his name, even though he had never
set foot in the state of Texas. They lived in Connecticut, for god
sakes. Who wears cowboy boots in Fairfield County?
Hesitantly, Kevin began to lick the tops of the boots, barely getting his tongue out of his mouth.
"That's not licking!" Dallas laughed. "I guess you need some lessons on
licking. Let's start with something other than my boots." Kevin knew
what was coming. "So I want you to lick my dick."
Kevin could hear Tommy whispering to Zane giving him the missing
history on blowjob bets and on Dallas-Kevin's animosity. Everyone else
was sitting down and watching us with complete focus. No one said a
word. No one looked away either.
Kevin undid Dallas's belt and unsnapped his jeans. Together they worked
them down to the middle of his calves. Dallas grabbed his obviously
erect package in his underwear and shook it at him. "Lick it!"
He began to lick his cock through the cotton. Kevin couldn't believe he
was in this position. Dallas was really hard and moaned slightly. Kevin
paused but then realized it'd be better just to get over with. Kevin
took the waistband of the grey FTLs and pulled them down. The briefs
went over Dallas's 6 ¼" cock with difficulty. But when lowered, it left
Dallas's member staring straight-out, directly at Kevin.
Only one other guy in the room knew with certainty that this wasn't
Kevin's first time blowing a guy. When he was 13, Kevin had blown
Oscar. Oscar had likewise returned the favor. They did it for a couple
months before almost being caught by Oscar's little sister Maggie,
which scared them into stopping. In the four years since then he had
thought about it during dry-spells with girls, but ultimately was too
scared to mention it to Oscar or to anyone else.
Of course, Oscar's dick was a lot smaller back in middle school than
Dallas' was now. It looked huge to Kevin although he realized his own
dick was bigger. Remembering a little from middle school, Kevin opened
his mouth and reluctantly began to pleasure Dallas's cock.
"Oh shit!" Zane could be heard saying. Kevin could only see with his
peripheral visions, but Greg and Neil were both in his line of sight,
both readjusting their own packages.
"Yeah," moaned Dallas. "That's good. Let's get my pants all the way off."
With Kevin's help, Dallas removed his boots, socks, pants and
underwear. Then his shirt for good measure. Standing completely naked
with only a thin gold chain and a high school ring, Dallas's exquisite
muscled form was the envy of most guys. Kevin returned to sucking. The
faster he got this over with, the faster it was over. Shit, they were
all going to college in the fall. What the hell was happening?
Dallas began to grab Kevin's head, adjusting Kevin's pace and depth.
"Yeah," Dallas kept saying. As the "yeah"s increased in frequency and
volume, Kevin knew Dallas was close. When Dallas sucked Neil, he had
pulled off and made Neil shoot onto the linoleum floor. Kevin assumed
this would be the same and prepared to stop. But Dallas was holding his
head tighter and tighter with his dick firmly inside Kevin's mouth.
"Mmmmh-gggmmgg-gmhmhhhm." The waves of semen flooded into Kevin's mouth
as Dallas prevented him from letting go. "Yeah! Yeah! Swallow it!
Swallow it all!" Dallas shouted.
He and Oscar had never swallowed as 13-year-olds. But Kevin kept trying
to swallow as he started to choke and gag. Finally Dallas let go of him.
"You're an asshole!" Kevin coughed and spat and then stared up at the muscled Adonis from the floor.
"And you're a good cocksucker. Although that wasn't your first, I can tell."
"Fuck you!" Kevin wiped him mouth with hand and then grabbed someone's
beer from the poker table and finished the remaining half bottle in one
Kevin noticed that Dallas had made little effort to get dressed other
than his underwear. Dallas looked at the clock on the wall. "We've got,
what an hour and 45 minutes? Wow. Lots of time to do lots of things."
Kevin cursed himself for not making it the slowest blowjob in the
universe - but it hadn't occurred to him at the time to extend the
amount of time he had Dallas's cock in his mouth.
"Get undressed. Everything," Kevin was commanded by Dallas.
The guys had all seen each other naked at gym class and after sports
practice. Four of them were on the soccer team and three on the
baseball team. But it felt different doing it in Oscar's den.
As Kevin began to disrobe, he heard Alex ask, "What about your folks and your sister?"
"My parents are out of town, actually," Oscar shared what Kevin and Dallas both already knew.
"So why aren't we having a party?"
"Because my grandmother is here. She's asleep and can't really climb
down stairs too well, but if we make a lot of noise, she'll be sure to
wake up. My sister is sleeping over at a friends."
"Too bad," Ethan teased. "I'd love your sister to be here right now. She's a little hottie."
Oscar threw an empty soda can at Ethan. His sister was in 9th grade and
was a forbidden subject for the other guys to broach. So they did it
all the time. But Ethan was harmless.
Kevin had removed his sneakers and socks, when Dallas told him to stop. "Do a striptease..."
Fuck, Kevin thought. Tommy had been scrolling through his iPod,
connected to the stereo already, and soon had some disco beat going.
Kevin paused. He wasn't embarrassed about his body. He was in good
shape, worked out a lot. And he wasn't embarrassed about his cock - 7"
and quite attractive, he thought and had been told. But displaying
himself so brazenly to the other guys...
Kevin was an adequate dancer and moved his body to the rhythm as he
began removing articles of clothing. He wasn't drunk enough to really
go at it - none of them got drunk on poker night with so much money at
stake. Neil and Tommy began to clap.
Kevin made it down to his underwear and Dallas commanded that come off
too. Kevin lost the BVDs too. He tried to stand proudly - his body had
some definition and he had a light spray of hair across his chest,
arms, and legs. But as he stood erect, he found himself standing...well,
"Enjoying this?" Greg asked.
"He looks pretty happy," Tommy added.
"Well, then, let's keep him that way. Who wants a blowjob?" offered Dallas. Kevin's eyes opened wide in complete shock.
None of the guys were willing to step forward, so Dallas took further charge. "Oscar, it's your house. What about you?"
Oscar passed, but Ethan didn't when Dallas asked him next. To his
dismay and surprise, Kevin suddenly was back on his knees with his lips
around Ethan's skinny small cock. Ethan was never sexually forward and
even as he started to gasp from the first touch of Kevin's lips, he
made no effort to remove much of his clothing. Seeing Dallas's muscled
body and Kevin's shapely form, he didn't want to hear jokes about his
pale, freckled, red-haired, rib-countable body.
Kevin was determined to make this blowjob last as long as possible when
he heard Dallas ask Alex, "So you want to fuck our little sex slave?"
"What!" Kevin shouted letting go of Ethan's cock.
"Whatever I say," Dallas emphasized.
"Fuck that. I won't do it." He jumped up leaving Ethan to uncomfortably
push his erect member back in his pants. "There is no way I will get
fucked by anyone tonight. The bet doesn't cover that. So go to Hell."
Dallas had a smug look of confidence. "You'll get fucked by everyone here tonight, K-Dog. And I bet you'll love it."
A huge debate broke out among the guys. Kevin, with dreams of law
school in the future, started arguing that some things were over the
line. "Could he ask me to chop off a finger or rob a bank next?" Before
Dallas could answer, Alex told him that was a stupid comparison. Those
examples caused permanent physical harm or were illegal. They debated
various examples of what was or wasn't over the line when Tommy
suggested a vote. A vote was the usual way to resolve disputes on
"Who thinks," Tommy looked for the right phrasing, "as Kevin does, that certain sexual acts..."
"...like being fucked," Alex added.
"..like being fucked, can be turned down by Kevin?"
Kevin's hand short straight up. Oscar followed suit. Kevin stared
directly at Greg and then Neil, he assumed his most persuadable
advocates. Slowly Neil raised his hand.
"Three for Kevin," Tommy announced. "And who thinks he can't refuse
that act and must do what Dallas says as long it is reasonably not
harmful or illegal."
Dallas, Ethan, Alex, and Tommy raised their hands. That didn't really
surprise Kevin. Ethan would take sex however it came to him and Alex
and Tommy both had reputations as major players.
"Four for Dallas."
Greg began to raise his hand but then lowered it. "Wait. I want to vote with Kevin."
Kevin smiled and said, "4 to 4." A lifetime of friendship between Kevin and Greg was paying off.
Everyone turned to Zane.
Zane had been sitting farthest away from the action nursing a beer. He
shook his head. "I gotta abstain, guys. I'm just a guest."
Everyone began lobbying Zane to make a vote - everyone agreeing that he
certainly got one. They noted it might affect him too. He clearly
didn't like the pressure and was not used to having to talk in a group
"Fine!" he shouted to shut everyone up. "My girlfriend is back in
Michigan. I haven't seen her in weeks and I hear she is cheating on me.
I could really go for a blowjob. I vote with Dallas."
A small cheer went up from the guys who now began arguing who would get
to do what. Kevin was about ready to jump and bolt when Greg and Oscar
both cornered him.
"You have to do it, Kevin," Greg pressed. "Whatever it is, you bet and your word is your word."
"Fuck that!" Kevin hissed.
"Hey, K," Oscar tried to look sympathetic. "You know if you back out on
a bet no one will ever bet with you again. Ever. That's the way it has
to be. No poker. No blackjack. No sports." Kevin was kicking ass in the
current NCAA Tournament pool, which netted considerable winnings.
"Look, I feel for you, buddy," Greg added. "But you said whatever
Dallas wants. That was a stupid bet. And he beat you totally fairly at
the poker table. Now you have to follow through. We voted with you,
"...But now you are both going to enjoy yourselves?" Kevin completed his thought.
Neither boy responded, but slowly stepped away. Dallas approached them
and after a quick conversation with Ethan and Alex, and some notes on a
paper, he made his announcement.
"Okay, I have figured out tonight's agenda. Kevin will have to suck
each of us. A guy can do that all the way until he cums or at any point
he can head down to the other end and pound his ass."
A few guys cheered.
"Better yet, he is going to do both at once, so both his holes - hit
mouth and his ass - are always filled. Everyone only gets one turn, so
when all eight of us have gone, that's when we'll call it an evening,
bet fulfilled. Even if it is before 1am. But we'll also stop at 1, so
the first few guys shouldn't drag it out."
Kevin had his best poker face on. He had put on his underwear when the
argument began. He had never been fucked in the ass and had never
really thought about it. He had never had anal sex with a girl either.
He had tried one of his fingers in the shower once, but chickened out
after barely getting started.
The room was hushed as everyone looked at Kevin for his response. None
of the other guys seemed uncomfortable with the notion they were about
to have a homosexual sandwich with their friend. Other than Dallas's
sucking of Neil a few months ago, there had never really been any
sexual play when they guys were together as a group. But they all
seemed ready to give it a go without much complaint.
"I have a few requests," Kevin piped up quietly. He knew he had lost.
He knew this night was gong to haunt him forever. But he could still
try and make the most of it and ease some of the elements. A more
submissive tone would get better results with Dallas. A nod encouraged
him to go ahead. "First, I just want to say you all are assholes and
should die, but that's beside the point."
"Point noted," Dallas smiled. Kevin was at least trying to make the best of it, he recognized.
"Second, you need to wear a condom. I don't want to acquire any diseases from you whores."
"Agreed, but only for the fucking. No condoms on the blowjobs." Dallas added. "Oscar?" Oscar noted he had plenty in his bedroom.
"Third, I'd like to do this on a bed. I need my knees to catch a ballgame this Sunday and the linoleum doesn't help."
Oscar nodded again and Dallas agreed.
"Fourth, no pictures." Reluctantly they agreed as he saw Ethan pocket his camera cell phone.
"And last. I don't want anyone to cum in my mouth again. You should jack off into a towel or something."
"Denied," Dallas shook his head. "If someone wants to do that, tough luck." Kevin closed his eyes again.
"Can I shoot both in his mouth and his ass?" a much too excited Neil asked prompting laughter from the others.
Dallas thought for a moment. "No, you get one cum. Pick where."
"Who goes first?" Alex inquired.
"I've decided we'd do it by age, oldest first. So that makes it Ethan,
me, Greg, Oscar, Alex...uh who is older Tommy or Zane?....okay Tommy then
Zane and then Neil."
"You already went!" Kevin protested.
"I won the bet. I get to go twice. And after this long a break, I am
totally hard again. It was such a nice blowjob that I wonder what your
tight ass is like. But, as a kind friend, I'm letting our sexually
deprived friend Ethan bust your cherry cause I think he's small enough."
"Fuck you! And thank you!" Ethan pretended to be upset.
After a few more questions, they moved to Oscar's bedroom upstairs. It
was a large, comfortable room with a Queen sized bed. Oscar had bought
the bed with his own money once he started fucking his girlfriend
regularly. Soon, Kevin was naked again and as if they did this all the
time, he had Ethan's dick back in his mouth.
Ethan was very excited. Shy about his body, he had little sexual
experience. He had been blown only once - a half-assed job by a former
girlfriend who bitched about it the whole time. He was greatly enjoying
Kevin's superior skills. But he also was excited to fuck Kevin's ass -
and be the first one to do so, as far as he knew. Ethan had only lost
his own virginity this past winter break - the last of his friends to
do so - and thought this would be an exciting experience to be the
first one at.
Kevin was working quickly, wondering if he could get the guys to blow
in his mouth and not fuck him. Although he wasn't sure which he thought
was worse. Sucking cock had some tactile appeal - the texture, the
rhythm, the groans from the guy. But he wanted to get through all eight
guys - EIGHT! - as quickly as possible.
As Ethan felt the pressure build, he showed surprising restraint,
pulled out of Kevin's mouth, and took a condom out of the box on the
bed. Rolling it onto his 4 ½" dick, he moved behind Kevin, unsure
exactly what to do. Both Dallas and Alex gave his some pointers. Alex
added a couple for Kevin. "The more you tense up, the more painful it
After applying liberal amounts of lubricant that Oscar had, Ethan
grabbed his cock and his friend's ass cheeks, lined up the hole and
"Ooooowwwwwwwwww!!!!!!!!" Kevin shouted.
"Shut up, Kevin!" Oscar quickly blurted out. "You'll wake my grandmother. And if she walked in, this'd kill her."
With a little more advice on keeping it slow, Ethan began to push in
deeper and out, over and over. Kevin kept making all sorts of pained
noises and cursing, although he had stopped screaming. Ethan was having
a great time. "This feels so awesome!" he cried.
As Kevin made another loud moan of pain, he was faced with Dallas's
thick dick in his face again. "Put this in your mouth and that should
shut you up."
It was quite the sight. Skinny, freckle-faced Ethan behind, tall,
muscled Dallas in front, and handsome, sandy-haired Kevin in the
middle. None of them could have dreamed it in a million years when they
woke up this morning.
Kevin pushed faster and faster. Dallas told him to hurry up because he didn't want to shoot in Kevin's mouth again.
"Oh, oh!" Ethan began to mutter and then he pulled out suddenly,
whipped off the condom, and with two strokes shot a slimy, spray all
over Kevin's back.
"Ethan, what the fuck?" Kevin dropped Dallas's dick as he realized what had happened.
"I saw it in a porn movie...I was inspired," Ethan, dripping with sweat, had an ear-to-ear grin.
"That only happens in gay porn," Tommy blurted out before realizing what he had said.
Before anyone could respond, they heard another shout from Kevin.
Dallas had moved to the other aside of the bed and had thrusted his
much larger and thicker tool into Kevin's hole. Kevin begin to moan in
pain and curse repeatedly. While Ethan had restored his underwear, all
the other guys were watching closely.
"How was it?" Neil excitedly asked Ethan.
"I won't say it was better than with a girl," Neil said carefully, "'cause I haven't sampled enough."
"Or any!" Greg choked out
"Fuck you, Greg. You know that's not true. But I will say, it fucking rocked."
Between his moans of pain, Kevin couldn't help but feel a smidgen of
pride for the pleasure he apparently could bring his friend.
Once Dallas got a rhythm going, Greg stepped forward. At 6', he had
blond hair that had darkened since his straw colored mop in
kindergarten. It was long and messy, and covered up his one earring. He
was usually intense, but outgoing. He did tend to obsess over things
such as girlfriends, sports, and school. He was very overprotective of
his brother Neil. Greg was in good shape with little muscle definition.
But the muscle that mattered to Kevin was staring him in the face.
Looked to be about 5 ½ inches that Kevin soon had in his mouth.
Dallas was enjoying every moment. He had never really liked Kevin -
well, that wasn't true. He hadn't liked Kevin in a while. He had stolen
Kevin's girlfriend Amy three years earlier because Kevin had been a
dick to him, he thought, the whole year. He didn't know why. Kevin had
just stopped being his friend at some point in junior high and it made
Dallas mad. He hadn't analyzed the relationship.
He also was enjoying it because he liked ass fucking. His girlfriend
didn't, so this was a treat. His last girlfriend was a stupid skank,
but she liked taking it in the rear. And Dallas had never considered it
cheating the times he had been with a guy in the past - not that anyone
knew anything about that.
Kevin had really given good head, much to Dallas's surprise, and now
was a great fuck, or at least his ass was doing the right things. The
sandwich idea had popped into his head and it was working perfectly. He
had to admit, Kevin was being a real sport and he started to remember
when they were best friends years ago and Kevin was willing to do
anything with crazy Dallas.
Dallas tried to copy Ethan's porn-style cum, but he didn't make it. As
he realized he was over the top, he had only just pulled out. The cum
shot went everywhere - the condom, Dallas's hand, Kevin's ass, the bed,
even a little on some of the guys standing too close. Kevin shouted.
Oscar cried out in complaint. And Greg was none too pleased as Kevin
An apology, a towel, and some moving around got things going again.
Only now Greg had moved to fucking and Oscar was waiting for his
Greg looked around as he pounded Kevin' s behind. This was his first
time with a guy...well, if you don't count the handjob that his brother
Neil had given him two years earlier. And he didn't count that. This
was not the first time he had sex in front of any of the guys here. He
and Kevin had double-dated and ended up both fucking their dates in his
SUV. And his brother had watched him fuck a few different girls. After
discovering Neil had been spying on him and the girls he brought up to
his room, Greg had given his brother permission to watch by keeping the
bathroom door ajar - as long as the girl never found out. It wasn't
that Greg was twisted. It was that he liked to perform. On the stage,
on the ball field, wherever. He was the go to guy to emcee events and
the first to speak up in a group. He liked to be the center of
attention - and he liked sex. So this was a nice combo. That he was now
fucking his oldest and one of his closest friends didn't really bother
him. Another experience to throw into a future acting moment.
Oscar was conflicted. Kevin was his best friend. But Kevin had sucked
him before. Kevin was the one who stopped doing it. And Kevin had lost
the bet. Plus, Oscar was horny. He and his girlfriend had been fighting
a lot lately and therefore the sex was practically nil. Masturbating
only took you so far. He needed a blowjob and a fuck. But ass fucking
wasn't his thing, so he planned to do what he never could at 13 - shoot
into his friend's mouth.
Greg's was fully inserted when he shot. He liked the pressure on his
dick immediately afterward and continued thrusting for another minute
after he came relishing the crowd of boys watching him. Oscar meanwhile
was enjoying a return visit to Kevin's mouth. Kevin seemed to have
improved despite Oscar's dick naturally being longer and thicker than
in 7th grade.
"I'm staying here," he whispered to Kevin, who had assumed as much and
prepared himself. Only a minute later, Oscar let out a soundless grunt,
held onto Kevin's head, and exploded. Oscar was pushing his dick too
far back as he came and Kevin began to gag and then couldn't swallow
the seemingly massive amounts of semen in his mouth and most of it
poured out of his mouth.
"Fuck!" Oscar barked as he watched his bedspread and own legs get smeared. Kevin was coughing and reaching for a towel.
"I'll buy you a new comforter with tonight's winnings," Dallas trued to
console Oscar as he pulled on his clothing. Oscar laughed and accepted
the offer. He could use a smoke, but grandmother, slightly deaf and
blind, had the nostrils of a bloodhound and would smell it for sure.
Kevin took a few minutes to clean up, drink some water that Neil kindly
went and got him and then down another beer. The drunker the better.
"You okay?" he asked.
"No. But I'll survive. I think." Kevin smiled back. Neil was much more
considerate than Greg who was too much of an egotist. And cuter too.
What the hell am I saying?, Kevin dismissed it as he reluctantly went
back to the bed.
Alex stepped forward. At 5'8", he was in great shape playing not only
an excellent second base, but also doing track, soccer, and wrestling.
He had an few wild years right around ages 11 and 12 and was sent off
to a boarding school for most of 7th and all of 8th grades. When he
returned for high school, his mom had gotten rid of her abusive
boyfriend and Alex was in complete control of himself. So much so that
he was very direct in getting what he wanted and very focused on
achieving it. As a freshman, he claimed he would fuck the unbelievably
hot junior, Mindy McAdams. A couple bets later and a couple weeks gone
by, and Dallas and Greg were amazed to peer through the window to watch
their 14-year-old new friend pound this 17-year-old stunner. They
thought the were watching him lose his virginity, but Alex had never
told anyone that he had forcibly lost it age 11 to his mom's abusive
boyfriend. None of them also knew that had fucked his first girl at the
boarding school two years later.
Sex with guys wasn't something he talked about, but it was something he
did. He had kept it away from "the poker crowd," as some of his other
friends called this group, but had enjoyed - and sometimes not enjoyed
- sexual trysts with boys and some older men. He usually bottomed, but
was glad to have a chance to top this evening. He had long thought
about sex with each of the members of the poker group. Kevin was always
the primary subject at least until recently when Tommy had taken over
that spot in his imagination. Alex didn't know that most of the guys in
"the poker crowd" knew he was bisexual and had known for a while.
Fully naked, the other guys looked at Alex's four tattoos, usually
covered up. The discovered a fifth one had been added on the small of
his back and was some geometric design. They also saw a scar running
along Alex's shoulder, which only Kevin knew was also a legacy from his
Alex didn't spend long getting blown. While Kevin had some promise as a
so-called novice - he had seen some interesting communication between
Oscar's and Kevin's eyes as Oscar was being blown - Alex didn't need to
get a blowjob here. He was sad he couldn't have been first in Kevin's
ass, but he would still enjoy it. As he put on the condom and reapplied
the lube, he began to insert a finger or two into Kevin's rectum. For a
moment, he was tempted to lean down and rim his friend, but discretion
took hold and he instead repositioned Kevin to give him more comfort.
Alex's thick dick could hurt and he always wanted to show variety to
the usual stick-in heterosexual fucking.
Kevin was now on his back with his feet spread up in the air, Alex
began to delight in fucking a straight guy in front of so many straight
guys. Well, Alex wasn't sure how many of them were straight. He knew
Tommy wasn't. He assumed Neil wasn't. Ethan seemed too new to sex to
understand what he wanted. Kevin and Oscar clearly had some sort of
sexual history together. Greg had some creepy vibe he never understood.
And Dallas...Dallas was doing it on the down low. He definitely had taken
it in the ass. Ever since he saw him so easily blow Neil, he was sure
In this position, Alex was able to brush his hand occasionally over
Kevin's dick - not enough to jack him or to be really noticed either.
"Tommy, you're up," Dallas called.
Tommy was an Abercrombie Boy. Beautiful, very thin, and natural
looking. Whatever he wore he looked comfortable in and it made him look
hot. He had poor upper body definition, but his hairless body, soft
skin, and long fingers, and sweet disposition made him very popular
with everyone. He was also an excellent poker player, a decent pianist,
a successful kicker for the football team, and a struggling benchwarmer
for the soccer team. He had small earrings in each ear and was
considered the kid with the best taste in clothing in the school.
Tommy also loved sex. Since he fucked one of his friend's older sisters
when he was a freshman, he had parlayed his beauty and seeming
innocence into the pants of girls everywhere. At first. By sophomore
year, he had discovered he liked boys much, much more. He kept it
hidden because of his parents' strong church background and had mostly
and publicly stuck to the girls. But he was becoming more and more
certain that he was fooling himself too. He liked having sex with boys
and had worked hard to find opportunities away from school to
With Alex still pounding away, Tommy finished undressing. The other
boys noted his beautiful 6 ½" circumcised cock, perfectly trimmed pubic
hair, and otherwise sensual body. Alex took one look and immediately
decided what his next project was going to be. Tommy got hard quickly
and was in Kevin's mouth, coming in from above on the prone 17-year-old.
Kevin was getting tired. He concentrated on getting each of the boys
off quickly. Alex, enjoying himself, but not wanting to belabor the
experience for his friend, hurried himself along. Tommy had moved
around to straddle Kevin's chest and feed his cock into his mouth. Alex
wasn't sure, but it seemed like Tommy was showing his ass off to him.
And it was a choice ass too.
Staring at the next place he hoped to put his dick, Alex pulled out and
shot on Kevin's crotch and stomach, coating Kevin's half-hard cock with
Alex's own cum but not shooting far enough to reach Tommy. Kevin tried
to complain, but suddenly Tommy jumped off him, spun the older boy over
back onto his stomach. He knew what was coming with the next
participant and Kevin needed to be in a better position to respond.
Zane had never played poker, but Tommy had asked, and Zane didn't know
too many people yet. He had only moved to town a few months ago, his
father being transferred from Michigan. Moving in the middle of junior
year totally sucked. Zane was a superstar back in his hometown - many
friends, girls, success in sports and the community. He didn't want to
start all over for just a year and a half, so he had been slow to make
friends locally. He also knew he'd be going to the University of
Michigan and most of his friends were going there too. He spent more
time on the phone and instant messaging them than connecting with his
new classmates and neighbors.
But Tommy was someone who always greeted the stranger and who was
instantly liked. Their friendship grew quickly and he began to enjoy
getting to know Tommy's friends. He recognized Tommy was gay early on,
but who cared. He never brought it up since Tommy never hit on him or
made a deal about it himself. Zane's uncle was gay, so he didn't
practice the intolerance that many of his friends back in Michigan -
and here in Connecticut - did. When Tommy suggested Zane join the poker
game, Zane was hesitant, but agreed. He lost quickly his first time
there, but watched several episodes of poker on TV, and lost less
quickly this time. Plus he was starting to get it more and didn't even
need the helper sheet with the order of the hands.
Zane didn't like being naked in front of other people, especially guys.
It wasn't his body. Zane was in incredible shape. He had very short
dark hair and long sideburns with a cleft in his chin. His abs were
carved from marble and he worked out extensively as well as ate
carefully. He loved having a body that girls stared at as he walked by
and he secretly even went to a tanning salon to stay the color he liked
all over as well doing some waxing and shaving. But when guys saw him
naked, it always boiled down to lust or jealousy, and he didn't enjoy
either. As Zane pulled off his underwear, the reason he didn't like
being naked became obvious. The attention to one thing.
"Holy shit!" Kevin shouted. Zane's still flaccid cock was huge. Even as
he adjusted to Tommy rear thrusts and Alex's still dripping cum on his
crotch, he shuddered at the third leg that swung between Zane's
"There's no way..." Kevin stopped short, but everyone knew what he meant.
Every eye in the room was on Zane's cock. Zane wasn't sure how to
proceed. He was still technically dating a girl back in Michigan but
had heard that she was cheating on him. Zane had been loyal and
therefore hadn't had sex since his visit with her in February. He was
always horny and had to jack off a bit to make sure he didn't get hard
in public - something he couldn't hide. But what fuck, he said. All
these other straight guys with girlfriends are doing it - it's not like
I'm dating him, I'm just getting a blowjob. He moved forward and began
to rub his cockhead over Kevin's lips.
It was a little challenging to get hard with everyone watching and
everyone being a guy, but Kevin was determined to make Zane cum in his
mouth so he wouldn't have to feel it in his ass. As Kevin went to work
on the uncircumcised monster, Tommy smiled. He had seen Zane naked in
the showers, but had never seen Zane hard.
"How big is..." Neil quietly asked what everyone was thinking.
"I dunno" Zane mumbled. Actually 9 ½", but who needed to boast, he always said.
"You could be a porn star," Greg noted, but Zane had no interest in
that. He wanted to do something in medicine. But he was hoping to first
do some modeling - clothed modeling - to pay bills in college. He had
been trying to convince Tommy for the two of them to audition together.
Tommy tried hard not to be obvious. Fucking Kevin while Zane's blowjob
began gave him a good position to stare forward, but he was not able to
see Zane's cock go in and out - Kevin's head blocked his view. He had
liked Zane as a friend immediately, but was also instantly attracted to
him sexually when they first met. He had tried a few times to hint to
him, but Zane missed or just ignored the advances and Zane was also
stuck on this stupid girl back home. Just watching him - a perfect
twink looking at a sculpted beauty (with a pretty good looking guy
between them) made Tommy even harder. He wondered if after tonight he
could try something with Zane after tonight - was the door now open a
He laughed at the word "crack" and also felt his orgasm building.
Knowing cum could work as a helpful lube, he prepared Kevin's ass for
Zane's cock by pulling off his condom and shooting right onto Kevin's
"Hey!" came the cries of surprise from the few guys who weren't just staring at the Zane's now-hard monster.
Tommy stepped back and without covering up at all, cum still dripping
from the head of his cock, watched Kevin working on Zane. Kevin was
really going at it. He was licking the sides, sucking on the head,
stroking it with his hands. With Tommy done, he had freedom of movement
and used it to try and get Zane to cum quickly. He didn't want it in
his ass - even if it wasn't really hurting so much anymore when the
guys fucked him, but actually felt sort of good.
Zane had never been a player. He worked hard in school and sports and
always held a job. And he was a bit shy, so he never took advantage of
his looks to get with too many girls. The blowjob Kevin was giving him
was pretty damn good compared to his past. Most girls were a bit
intimidated by his dick. They might let him fuck them, eventually, but
would barely even try with a blowjob, usually moving to a handjob at
best. Shawn, his current girlfriend, gave a passable blowjob, but
Kevin was much better - he had far more passion and energy. Zane knew
it was to avoid getting fucked in the ass. Zane had never had sex with
a guy until right now and he had also only fucked one girl in the ass -
which was an unsuccessful experience for both of them. If he was going
to ever fuck a guy in the ass, Zane admitted to himself as he looked
around the room, it would be Tommy's ass he'd most like to pound.
Offering no resistance, Zane let Kevin work his dick over. Zane
imagined his hot girlfriend naked, and famous celebrities naked, but he
kept opening his eyes and glancing at Tommy's naked body. He'd quickly
look away, but he was sure Tommy had seen it each time. Zane knew he
needed to get this over with. He grabbed Kevin's head and forced more
and more of his dick in. Kevin, surprisingly, went deeper than any girl
Zane had been with before, which excited Zane.
"Mmm mmm," Kevin tried to comment on how deep it was, but Zane pushed
forward and then held Kevin's head firmly and tightly, keeping the pace
up. Amazingly he wasn't gagging at all.
Then, with several hard breaths, Zane pulled out of Kevin's mouth and
stroking himself furiously shot right into Kevin's face. Kevin tried to
move over, but Zane still had one hand on his head and held him still.
The load was huge and coated Kevin's entire face and much of his hair.
It seemed Zane would never stop shooting, but finally he did and let go
of Kevin who had his eyes and mouth closed to avoid getting more in
Zane stepped away and immediately put on his underwear and pants. Tommy
had done so too because he was totally hard from watching them. Other
boys were shifting their semi-hard to hard dicks around.
Neil brought Kevin a towel, and tonight's "sex toy" took a few minutes in the bathroom to clean up and rest. Only Neil to go.
Neil had loved the blowjob from Dallas three months earlier. It was his
first - and only one. Since that night, Neil had been able to fool
around with just one girl. His brother had basically thrust her upon
him. He had been terrified, and though she had been willing to go
pretty far, he found himself soft and frightened. Eventually, she
passed out drunk with her hand still down his pants. He had gotten up,
gone off to the bathroom, and jacked off.
He was a virgin, but felt no rush to fuck some girl. While he saw how
much fun Greg had with girls in his room, he couldn't see himself doing
that right now. Too scary. Kevin had always been great to him. Neil had
always tagged along after his brother Greg. By freshman year he had
found Greg's friends were also becoming his. The invite to the poker
game came soon after.
Having watched seven guys blow their load on, around, and in Kevin,
Neil was beyond horny. In fact, he had already cum once in his
underwear while watching. But he didn't tell anyone that as he quickly
undressed revealing his still emerging body.
Neil had begun to have the slightest muscle definition because Kevin
had given him a simple workout routing to do at home. Neil was 5'6",
completely hairless other than a small patch of pubic hair and under
his arms. He needed a haircut, as most of the guys did, but usually
used considerable amounts of gel to style it. Tonight it was loose and
an 'adorable mess,' as his mother called it. He was totally hard just
from looking around the room.
"You're doing pretty well at these poker games," Alex noted. "This is blowjob #2 for you."
"You can be #3," Neil responded confidentially, but only slightly in jest.
Alex smiled broadly. He was definitely right about Neil. The other guys hooted at Neil's bravado.
Greg looked at his brother's naked form. It was shorter, slimmer and
less athletic than Greg's had been at 15. When Greg had been 15, Neil
was had seemed so young, when he caught his brother spying on him. Greg
was trying to lose his virginity. The girl had refused and left Greg
horny and angry when he discovered his brother had been peeking through
the open door. He had punished Neil that night making him give Greg a
handjob. If he had any guts, Greg regretted, he would have done much
more. They were in the moment. Since then, Greg hadn't been interested
in anything but fucking girls - but he did like letting Neil watch him.
He was sure his brother was gay. Pushing that slut Tonya on his brother
last month and watching him go nowhere proved that. So Neil must have
really been excited, Greg decided, getting to be blown by another one
of Greg's friends. Greg was aroused staring at his brother's naked form
as he moved towards Kevin. That was wrong. This whole night was weird.
Kevin was a good friend and he had fucked him. How could they be
friends the same way? And now his brother was going to do the same.
That was freaky.
Zane was resting on a chair at the end of the room when Tommy came and
sat next to him. "Crazy night, huh? Was it like this in Michigan?"
Tommy broke Zane's quiet while marveling at the still shirtless boy's
Zane laughed. "No. It was most definitely not like this. I don't know
anyone that has been with a guy for anything - I mean if you don't
count the gay guys. None of the guys like me, I mean..." Zane realized
his remarks could be wrongly understood, but was unable to right
himself. "Not that gay guys aren't like me, I mean, I don't think..."
Tommy laughed. "Stop while you're behind, Zane."
"Tommy, you're my friend and that's all I care about. Everything else
is just details. I'm just glad you reached out to me when I was so
pissed at moving and unwilling to make friends."
Tommy smiled. Zane had noticed his come-ons, Tommy recognized, but had
been too polite to say anything. "You're a good guy, Zane. Your
girlfriend is very lucky."
"Yeah, but she doesn't think so. She's cheating on me. I've been
denying it, but while I've been faithful, she's been fucking around
"That sucks," Tommy wasn't at all sad and decided he had to use this
opening for one more shot. "Listen, I'm not putting any pressure here.
We're friends and that's all it need ever be. But when we drive home
tonight, if you want to...continue anything...I'd be available."
Zane looked at Tommy seriously in the face. "If I was going to
continue, what makes you think it'd be with you? Alex is pretty hot.
And Neil's got that innocent charm. I don't know you're my type. But
It took Tommy another few seconds to realize Zane's deadpan humor and
he punched Zane in the arm. "Fuck you, you dickwad." They both laughed
and turned their attentions back to Neil and Kevin.
Alex watched Zane and Tommy talk with some jealously. He'd love to bang
either of those juniors. One fuck of Kevin wasn't enough. He'd need to
find someone for later. But not anyone here it seemed. His straight
cover was still intact. Whether he was straight, gay, bisexual, or any
other term didn't matter to Alex. He liked sex. A lot. And his good
looks and oozing charisma, combined with his bad boy reputation from
his middle school days, made him attractive to everyone. He had a nice
dick and knew how to use it. And he was very good with his mouth and
ass. He have been happy get pounded by any of the guys in the room. But
with Tommy set on Zane, and Neil clearly fascinated by Kevin, that
didn't leave many options. Ethan was too much of a sexual novice. Greg
was a whore - not that he fucked so many girls, but he didn't care who
they were. And Dallas. Dallas was an enigma.
Dallas and Ethan were each drinking a beer and smiling. It was a good
night. Ethan loved expanding his sexual world so dramatically and
easily. And he had taken Kevin's virgin ass. If he could do that, he
could maybe be more assertive around girls. Be more direct, maybe.
Dallas, finishing off his bottle, leaned over as if reading Ethan's
"You did nice, Ethan. I was impressed. Not that I see guys fuck guys every day, but you did a good job."
"Thanks..." Ethan wasn't sure how to respond.
"So if you can do this," Dallas continued, "fucking your friend in
front of 7 other guys, why can't you ask girls out and fuck them in the
privacy of your own bedroom? Do you need all of us to come by?"
Ethan polished off his beer. He had a good buzz going and was feeling
totally relaxed and free. "I will, Dallas. I will. I definitely will."
Oscar was cleaning up his bedroom. He was mostly worried his
grandmother would have one of her nights of insomnia and barge in. His
bedroom door didn't have a lock. He had pushed a chair in front of it
and piled heavy books on it. That would slow his 80something granny's
This whole night was weird. The poker game was for making money and
having fun. Oscar only did bets that involved money, not these stupid
Dallas side bets. Tonight had made him uncomfortable. It had been over
4 years since he and Kevin had fooled around - the only guy he had ever
done stuff like that with. He hadn't wanted to stop then, but he also
hadn't thought about starting up since then either. At least not very
often. Kevin's lips around his cock, shooting down Kevin's throat -
that had been awesome. He'd have sucked Kevin off right then and there
- if it wasn't for all the other guys. This was weird. He had gone
Kevin was exhausted. But he wanted to make Neil's time special. Kevin
knew that like Ethan, this was a rare occurrence or Neil. But other
than Greg, Kevin was the only guy to know Neil had never had any real
sexual interaction other than Dallas' blowjob earlier in the year. Kind
of weird the boy's 1st two blowjob were from his older brother's male
friends, but the world was strange that way.
Neil was completely hard, his dick already leaking some pre-cum. Kevin
opened wide and swallowed the teen's cock. Kevin wasn't sure why he
liked Neil so much. He was always looking after him, but it wasn't as
if Greg didn't pay attention to his little brother. Neil was certainly
the younger brother Kevin wished he had, but there was something else
he couldn't define. Kevin realized he'd be the first, and maybe only,
person to have sex with both brothers. Wonder if anyone else will ever
be able to say that, Kevin thought as he intensified the sucking. And
I've been with all my friends. No one else can say that.
Kaytlin Rogers. That's it, Kevin suddenly thought. Who was the girl
that had been with more guys here than anyone else - Kaytlin. They had
known her since elementary school and she had fooled around at least
once with Dallas, Kevin, Oscar, Greg, and Alex at one time or another.
Well, Kevin had trumped her record by a lot. Neil began pushing harder
and harder, fucking Kevin's face and grunting in delight.
"You gonna move ends or just stay there, bro?" Greg called out as a
reminder. He knew Neil might get too involved in the blowjob to stop.
Greg's words prompted a surprised look for Neil who immediately yanked
out of Kevin's mouth and walked around the bed. Dallas tossed him a
condom. He had never put one on before. Both Greg and Alex moved in to
help him, but Alex backed off in deference to the older brother. All
the guys noted how Greg had no problem helping hold his brother's dick
as he showed him how to use a rubber.
Having added lube to his shaft and squirted some directly in Kevin's
hole, Neil prepared for his first ever fuck and pushed his 6" directly
into Kevin. By now, Kevin was pretty loose as well as pretty sore. So
the pain wasn't from the entry, but from the friction. But Kevin bit
his lip. This was the last one and he'd be done.
Neil had his eyes closed and had found a pace of thrusting almost
immediately. The other guys were all staring, but none moved a muscle.
For a couple minutes, the only sound were Neil's quiet grunts and the
rubbing of bodies. Then Neil let out a surprised yelp, almost fell
forward, and slowly stopped pushing in.
Kevin looked over his shoulder. "Okay, Neil? You all done?"
"Yeah," Neil whispered and pulled out. Alex reminded him to grab the
end of the condom so it wouldn't fall off or leak, and Neil headed to
the bathroom to dispose of it there.
Kevin looked around, found his underwear, and put it on. "Okay?" he looked at Dallas.
"Okay," Dallas smiled. "Kevin, I gotta say. You are a fuckin' trooper.
Tonight is just about us here - no one is going to talk about it, right
guys?" Dallas looked around at the others who offered small nods of
affirmation. "But I'll bet with you anytime. You are a man of your
"And you have a nice mouth and ass," Alex added. Everyone laughed.
It was already 1:45am. Several of the boys had missed curfew, but
they'd all make up a story somehow to cover each other. Kevin slowly
got up from the bed. His mouth and ass both ached incredibly. He felt
like he had been on the losing side of a fight. It wasn't nearly as
terrible as he imagined, but it wasn't something he cared to repeat.
He was also hard. That was obvious to everyone there. Tommy and Zane began to whisper, and soon others joined them.
"Dallas, we have an idea," Tommy proposed. Dallas was fully dressed and
was deciding if he was sober enough to drive home. He had consumed too
many beers while watching the other guys fuck. "What's your idea?"
"We took a vote," Tommy continued. "and the rest of us all feel
that you owe Kevin a little something." All of the other boys nodded.
"You mean money?"
"No. He is the only one tonight who hasn't gotten off. You need to take care of that."
Dallas laughed. He wasn't sure he had heard them right. He looked at
each of them. Only Ethan looked similarly buzzed, but Ethan could
get drunk off just a couple beers. They looked very serious. They meant
"Fuck that. I didn't lose the bet," Dallas dismissed them. Kevin had said nothing.
A small argument broke out as the other boys tried to cajole Dallas into helping their friend out. Dallas wasn't budging.
"What about a new bet?"
"What? It's late. Fuck that."
"What about a new bet?" Neil repeated. "You and me."
Before Greg or Kevin could interrupt, Dallas asked, "What's the bet?"
"If you win, I'll come over to your house tomorrow night and be your
slave for the evening." Neil silenced the others with a stern look. "If
I win, you have to pleasure Kevin however he wants right here, right
now. One time."
"What's the game?" Dallas asked.
They argued about a variety of games before Greg suggested pool. Both
boys agreed and soon the nine of them were back in the den, still a
mess from the poker game.
Dallas was a good pool player. His tipsy state took a bit off his aim
and he was missing the harder shots, but his game was solid. What
Dallas didn't know was that Greg and Neil had a pool table for years.
Because the group never did anything at Greg's house, Dallas didn't
know anything about it. Neil had actually become obsessed with pool for
a while and had become extraordinarily good during middle school. The
skill hadn't left him.
"Eight ball in the corner," Neil announced finally and with a swish
push of the cue sunk the black and white ball cleanly winning 2 games
The boys cheered. Dallas shrugged. "I think I was just hustled," he sheepishly remarked.
Kevin smiled and dismissed the whole thing. "Nah, let's call it a night
guys. I'm really sore and just want to shower and start a new day, back
to being the pussyhound I once was."
"You were never a pussyhound, Kev. A bet is a bet," Dallas declared.
"I'm not a welcher. I made a bet. I'll keep it. 'Cause if I had won,
you can be damn sure I would have bounded that little fucker for hours
Neil kept a straight face, unsure of how to respond.
"What do you want?" Dallas asked Kevin. They stared into each other's
faces. Tomorrow they would act differently around each other - nicer,
kinder, closer. Maybe they'd even become friends again.
"I'll take a blowjob," Kevin shrugged.
Leaning against the pool table, Kevin dropped his pants. His hard-on
was still there. Dallas dropped to his knees, dropped his friend's
underwear and took the 7" cock into his mouth. After several bobs, he
pulled off allowing Kevin to remove his shoes, pants, and underwear,
and spread his legs wider.
The other boys, all of them hard at this sight, watched Dallas swallow
Kevin's tool. Soon, the cowboy boot wearing senior was taking the
entire shaft in, pushing his nose all the way to Kevin's pubic hair.
Tommy and Alex caught each other's eyes accidentally. In that one
second, they exchanged several statements: 1. I fuck boys. 2 You fuck
boys. 3. We should fuck each other sometime. 4. Dallas is clearly an
experienced pole smoker. What Alex assumed and Tommy never considered
had now become obvious. Dallas hadn't shown these skills when sucking
Neil, but now was doing exceptional work. It couldn't just be the beer.
Kevin started to moan. He was ready to burst at first touch, but
couldn't believe how good a blowjob Dallas gave. Better than any girl
he had known. Feeling pressure building, he pushed Dallas off to stop
"What?" the confused teen on his knees asked. "Am I not doing it well?"
"You are doing it too fucking well!" Kevin replied in between heavy breaths. "But, I want to fuck you, Dallas."
There was a long pause as Dallas was thinking through a variety of
options. Alex knew Dallas was deciding whether to admit his ass wasn't
virgin or to lie and pretend it was.
"You sure? I mean, I can suck you and you can cum in my mouth, I guess." Dallas tried as a diversion.
"Maybe later. Right now, I want to repay you for what you - and Ethan -
did to me. I want to take your vir..." Kevin cut himself off.
"What?" Neil naively asked.
"I want to fuck you," Kevin concluded his hanging thought. He didn't
want to embarrass Dallas into admitting something uncomfortable right
now. Dallas and Kevin exchanged a knowing glance of their own before
Dallas did a bad job of acting as he grumbled, "a bet is bet."
It took a couple minutes - Kevin insisted Dallas still wear his cowboy
boots just for kicks - as he pushed the recent 18-year-old onto the
pool table. Over Oscar's objections, Kevin inserted his cock in
Dallas's hard ass and began to push him into the table. The entire pool
table shook with each thrust. Oscar bitched about the new pool table,
but was hushed by the others who enjoyed watching these two physically
fit teens go at it. They all could see that Dallas was hard and was
stroking himself as Kevin continued to ram him.
Kevin was too horny and had too much pent up sexual tension to last
long. But the thrusts until then - the first Kevin had in someone's ass
- were fantastic. When he realized he was somewhat close, inone
forceful series of motions, he pulled out, ripped off the condom,
grabbed Dallas' shoulder, spun him around, pushed him to the floor, and
shoved his dick back in the only slightly surprised teen's mouth.
Grabbing his head, he violently face fucked Dallas for five strokes
before letting out a huge grunt. After shooting a couple times in
Dallas's mouth, he pulled out and stroked himself to shoot the rest
onto Dallas's face. The sexuality of the evening had built up and Kevin
shot multiple thick, sticky volleys, coating Dallas's features and
hair, dripping down onto his chest and stomach.
With a final grunt, Kevin dropped his dick have spent his entire load.
Dallas then dropped onto his back, continued stroking his own hard cock
and soon shot all over his own stomach and chest.
The other boys all stared in amazement at the ease with which they
engaged in these actions. Alex shook his head in particular
befuddlement. How could he not had recognized Dallas's gay experiences
before now? Neil shuddered and hunched over and he again shot a load in
his already sticky underwear.
The bet fulfilled, Dallas headed to the bathroom. By the time he came
out, Tommy and Zane, who had driven together, had left, much to Alex's
disappointment. Alex offered to drive Dallas home, but the wannabe
cowboy claimed he had sobered up in the fuck and headed out. Greg and
Neil likewise departed. Alex and Ethan headed out - they had driven
together. The departures were swift and the interaction was almost like
Kevin helped Oscar clean up the den. He especially made sure that there
were no cumstains on the pool table or carpet. There weren't any he
could find. It was nearly 2:30am. Kevin's folks didn't mind if he
stayed over at Oscar's on poker night, so all he had to do was leave a
text message on his mom's cellphone. She thought Oscar was wonderful.
When the house was clean, they sat on the back porch smoking pot
and drinking whiskey so Oscar's grandmother wouldn't hear or smell it.
Kevin was wired. Oscar felt ill. He didn't actually like whiskey, but
that was they could find. After a long period of silence they both
spoke at once.
"What did you..." "How do you..."
After the usual pleasantries they both shared their thoughts.
Kevin chugged some whiskey first. "I don't know. I had never done
anything with anyone, any guy, since we were 13. I hadn't really
thought about it either. And I didn't enjoy being the sexual plaything
of all my friends. But it was also...you won't ever repeat this,
right?...it was kind of fun. It felt kind of good. Good to make others
feel good, but the physical sensations for me were kind of enjoyable.
Very different than being with a girl, but maybe more like what a girl
Oscar nodded, but let his friend continue
"Everyone was so different. I never thought about guys being different
- not just in size, but in what they want, how they do things. I
learned a lot about each of you all as you...well, I mean, well, as you
"I didn't fuck you," Oscar replied.
"I know. And I was glad then. But I kind of, well, don't take this the
wrong way, I kind of wish you had. I remembered when we were 13. It was
fun. I just got so scared when your sister almost caught us and then
the whole 'that's gay,' shit."
Oscar nodded again. "What about Dallas?"
"Yeah, that was some fucked up shit," Kevin laughed. "He obviously has been with guys before."
"You think?" Oscar added sarcastically. They both laughed.
"I never would have guessed it," Kevin said. "I mean we all guessed it
about Alex, although he is still pretending he doesn't go both ways."
"Was it different when you were doing it with someone straight like
Greg versus someone more into it like Alex?" Oscar's curiosity prompted
him to ask.
"Hmmmm..." Kevin thought for a minute. "Well, guys with experience with
guys were better at it and more relaxed. Ethan and Greg and you and
Zane were all so awkward and nervous. But since everyone enjoyed
themselves, I don't think it matters."
"You didn't say Tommy or Neil."
"I know," Kevin's voice dropped. "There was a vibe, a knowingness about Tommy. I am pretty sure he's been with guys."
"Really? He always seemed like he was a player. I never really noticed
it. But yeah, he really did stare at Zane. I mean, Zane had a huge
cock. Everyone stared, but..."
"There's a difference in staring because you are amazed and staring
because you want it," Kevin shook his head remembering that giant slab
of meat in his mouth and grateful it went nowhere else. "I could see
Tommy in the mirror while he fucked me and then when he was done, he
"So Dallas, Alex, and Tommy all are fudgepackers?" Oscar concluded. The
he added "and so are you, now" as Kevin punched him lightly in the arm.
"And Neil," Kevin added. "He isn't yet. I mean, he is, but he hasn't done anything yet, but he is gay. Not bisexual, but gay."
"How do you know?"
"I don't know how. But he is," Kevin declared.
"Greg has a thing on his brother. Did you see how he put the condom on him? That wasn't normal."
"Yeah, I'd never do that to my brother." But I would do that for Neil, Kevin silently reflected.
"Your brother is an asshole."
They began to speculate what was happening right now, as the pot filled
their lungs. Was Greg having his way with his little brother? Were
Tommy and Zane getting it on? Did Alex, in lust for more manflesh, take
advantage of Ethan? And who knew where Dallas was.
"He's off with cowboy friends doing Brokeback Mountain re-enactments,"
Oscar and Kevin both laughed. Then it got very quiet. Neither said
anything or moved for a long time as they finished off their joint.
"And then there's Kevin and Oscar," Kevin whispered. "What are they doing?"
Oscar smiled. "Well, maybe they are going upstairs, stripping off that
nasty cum-stained bedspread, and, for starters, pretending they are 13
Kevin smiled back, took one more drag on the tiny joint that was left, and said, "That sounds plausible."
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