Youth Group: Hotel
Room Truth or Dare
This story series
includes depictions and descriptions of gay sex and straight sex among
high school students as well as gay incest. 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 anything true.
Comments, suggestions, and helpful feedback are welcome. - Send me an E-mail
Four high school students – a
junior, his freshman younger brother, his junior best friend, and a
senior – are stuck in a hotel room together on a youth group trip. With
nothing to do, they decide to play truth or dare with unexpected
results. After a round of truths, they moved to dares with the boys
trading blow jobs.
Part 3 – Dare – Round 2
“Fuck!” was all Evan had to offer. There was a moment of absolute
silence as Todd and Evan stared in amazement at Riley’s mouth wrapped
around his brother’s dick. Then the silence was broken.
BANG BANG BANG BANG.
“What in God’s name is going in there?” they heard the voice of
Reverend Tim call to them from the hall. “Open this door immediately!”
The four boys moved with lightning speed. Riley released his brother’s
cock and tossed Hayden his clothes. Hayden ducked under the covers
still naked and pretended to be asleep. Todd shoved the empty liquor
bottles fully under the bed, grabbed the remote, and flipped on the
television. Riley swigged his last bit of soda to try and clear his
mouth. Evan adjusted his hard-on and went to the door.
Putting on his boyish charm, the 16-year-old opened the door a crack.
“Yes?” he asked with wide innocent eyes.
Reverend Tim and Chuck were standing in the hallway with their hands on
their hips. Reverend Tim had clearly been asleep and was wearing his
pajamas and a robe. Chuck was still fully dressed, remaining on hallway
duty, and still held his copy of Kierkegaard. He wore a smug smile of
Reverend Tim pushed into the room. “Chuck said he heard shouting in
here. And I heard it too! Is
there anyone else in here?”
“No, Sir,” the boys answered in unison and honestly.
“What was the screaming about?” Reverend Tim quizzed them as he glanced
in the bathroom and around the room looking for others.
“Sorry, Reverend. It was the television. A movie on cable. We had it a
bit loud, I guess,” Todd completely lied.
Seeing Hayden seemingly asleep, he asked Riley, “Were one of you boys
picking on Hayden?”
Riley swallowed the last drop of cum in his mouth, stared straight at
the minister, and said, “Reverend, I can assure you, I have been
treating my brother better than he has ever been treated before”
“Did the television noise disturb you?” Evan asked with sympathy to
Chuck. “I am so sorry.” The other boys had trouble not busting into
laughter as Evan pulled his fake sweetness/angel routine.
“Turn the television off and go to sleep!” Reverend Tim ordered them.
“How do you expect Hayden to sleep with the lights on and all this
“Yes, sir,” the other three answered in unison.
As the youth minister headed to the door, they saw Chuck stare in
disbelief at them. Then Chuck sniffed several times. The smell of semen
was in the air and he must have recognized it. But teenage boys are
teenage boys. He couldn’t prove anything.
The door closed and all four boys stifled their laughs. “That was some
great teamwork,” Riley remarked admirably.
Hayden came out from under the cover and put his pajamas back on. Riley
went to brush his teeth and use mouthwash. Evan flipped off the main
lights as Todd turned on the bed lamps. There was plenty of light to
see each other.
When Riley returned, he looked at the other three sitting on one of the
“What?” he asked them.
“Round two,” said Evan.
“I think we’ve had enough, don’t you?” Riley suggested.
“Who goes first?” Hayden, ever practical, asked, ignoring his brother.
“Well,” said Evan, showing more astute logic than ever before, “I had
the guts to be the first dare last time. So I think I should be the
first to dare someone.”
That seemed sensible enough to other three who hadn’t quite thought
through where round two might take them. And they were impressed with
Evan’slogical deduction. “Todd…” Evan stated, “I dare
you…to let me fuck you.”
The words hung in the air as if they had been written out. Evan, who
despite his constant uses of “fuck you” and “suck me,” around guys,
never actually meant it. Until now as he had dared Todd to be fucked.
“What?” Todd responded in partial disbelief.
“You violated my sister. I want to show you that no one touches my
little sister or the punishment is severe,” explained Evan.
“Your sister approached me. And she only blew me. I didn’t fuck her. A
blowjob is the most equitable response.”
“No. I don’t know what the fuck that word means and I am doing the
daring and the deciding. You all agreed to round two. I dare you to let
me fuck you. In the ass. Right now.”
“You realize what this means,” Riley cautioned his friend. “I mean, you
know where this will take us.”
Evan shrugged non-committally. He was hard and he knew how he wanted to
relieve that. Todd shook his head and just sat there. It wasn’t an
anti-gay thing. He just always imagined himself on top. He hadn’t been
honest with the guys earlier. When he told the story about the two
seniors, he neglected to mention how while one sucked him next morning,
he had fucked the other older boy later that day. But he refused to be
on the other end despite their pressure. Now it was three years
later. Evan was certainly good-looking, as far guys go, but this was a
whole new world. Many of Todd’s gymnastics teammates were gay. He knew
the details of some of their sex lives, but always refused any offer to
experiment despite further curiosity. “I guess that day has come,” he
said to himself.
“Do you have any lube?” Todd said by way of saying that he agreed to
“Lube?” Evan asked. “When I fuck a girl in the ass, I just use spit, if
I don’t use her pussy juice.”
“Well, tough guy, I want lube,” Todd replied.
They went through their toiletries kits unsuccessfully. In the
however, there were several disposable bottles of hand cream, shampoo,
and conditioner from the hotel. “That’ll have to do,” Todd noted as he
grabbed all the hand cream.
Todd removed all his clothing, his big dick flaccid, yet still flopping
between his legs. Evan likewise stripped. Completely naked, except for
Evan’s baseball cap, Riley and Hayden could see what great shape both
boys were in – Evan from basketball, soccer, and baseball, Todd from
competitive gymnastics. Todd was naturally relatively hairless except
for a light dusting on his legs and chest. His pubic hair was neat –
clearly trimmed. Evan had more hair, but it was all dirty blond, like
his head. His pubes were overgrown and could use some attention.
Evan took the hand cream and rubbed it on his already hard 6 ½
inch dick. He directed Todd to lean over the side of the bed with Evan
standing behind him. “Put the lube on my ass.” Evan hesitated at the
request and realized Todd couldn’t truly reach back there. He coated
his hand and gingerly rubbed the senior’s butt.
“You have to get between the cheeks for it to have any effect,” Todd
corrected him. Reluctantly, Evan pushed his lotion-filled hand between
the butt cheeks. Funny, Riley thought, he’ll put his dick in Todd’s ass
without a problem, but his hands, Evan suddenly gets skittish.
“Ready?” Evan asked Todd.
“No,” Todd scowled and dropped his head and chest completely onto the
bed. Todd had been on the other side of this situation with a number of
girls. How did he end up here?
Evan’s practice was to go quickly. While most guys took ir little by
little, he found that a couple good thrusts of pain and it was smooth
sailing. So despite Todd’s cries of “Slower!” (and Riley’s reminder to
shut up or Chuck would come back), Evan assaulted the 17-year-old’s ass
without mercy. Ass pounding would be an excellent description of the
next few minutes. Evan loved the hard, tight, muscular ass. From
behind, you couldn’t really tell if he was fucking a guy or a girl
except the ass seemed stronger. The gymnast’s toned gluteus maximus
squeezed Evan’s hot cock with delight. Evan’s tall body pressed Todd’s
small frame flat into the mattress. The bed shook and Riley was worried
the people next door would complain. Evan’s loud grunts and Todd’s
continued “Slower!” weren’t helping easier.
“Be quieter!” Hayden’s caution had an effect and both boys dropped the
volume of their verbal utterances. The reminder also broke the rhythm.
“I don’t want to cum yet. Change positions. Kneel on the bed.” Evan had
rarely had this kind of control over a teen girl he was ass fucking for
the first time. He wanted to try several positions if he could. But
Todd’s ass was tight.
Todd crawled onto all fours on the bed, his head and chest dropped
forward. Evan kneeled behind him and he grabbed his waist and thrust
in. “Oh!” was the new sound from Todd as he showed signs of pleasure.
Evan looked like he was in heaven. The bed shook dramatically, even as
the other boys tried to keep their shouts quiet.
The fucking continued for maybe another five minutes. Evan, a little
tired from this position, was considering a change when he let out a
familiar, “Aaaaahhhhhhhhhhhhhhhhh.” He pulled his dick out of Todd’s
hole and sprayed his back with his teen cum.
Evan collapsed onto the bed in exhaustion, sweat glistening his
muscles. Todd didn’t move for a moment and then slowly stood up and
disappeared into the bathroom. They heard the water run and then the
shower. Hayden couldn’t help but notice that Todd was hard from the
buttfucking as he slipped into bathroom.
The boys said nothing to each other while they waited. When Todd
emerged about ten minutes later, he was wet with a towel around his
waist. “I take it we are even for the rushed blowjob from your slutty
little sister?” Todd asked Evan, who had restored only his underwear to
go with his Cardinals cap and returned to the big arm chair.
“Yeah, whatever, dude. Fuck me. That was fuckin’ awesome. I don’t care
what people say about gay guys. That was tighter than any pussy or any
ass I’ve ever fucked. Fuck me.”
“Great. Now it’s my turn,” Todd reminded them. Riley tried to convince
Todd to let it rest, end the game, let them sleep. The clock read 1:21
am. But Todd insisted that everyone had to take a turn in this round
and then it’d be done.
“Well, I have three choices who to pick,” Todd reminded them. “I could
get back at Evan for what just happened, but let’s say we’re even. I
could pick Riley and see what I can make him do, but he hasn’t done
anything to me. Or I can pick Hayden.” The freshman froze in his spot,
his face a poor mask against his fear.
“Cause, you may remember,” Todd continued, “it was Hayden who asked the
question about our fooling around with anyone else’s family member.” He
dramatic effect. “Did he do this to share his ridiculous thought that
Evan’s mom sometimes kisses him on the mouth? I think not.” Todd was
milking his moment for maximum drama.
“Did he do it to reveal about my brother Benji molesting Riley three
years ago?” he continued.
“Uh, Hayden didn’t know who it was,” Riley reported.
“Well, did he do it get Evan to share the story of his sister’s jerking
him at age 11? I bet he didn’t know that story at all.” Evan and Riley
both nodded to confirm.
“Then, given the unusual nature of the question, I’m guessing he did it
to get me to reveal my…encounter with Emily. And he did it knowing the
would cause in Evan. He did it to fuck with me and Evan. So I think he
should get the same.” Hayden opened his mouth trying to find something
to defend himself, but Todd was right. Hayden had kept his discovery
about the blowjob a secret for over 6 months and decided tonight he
could use it for fun.
“Therefore,” Todd summed up as if he was speaking before a judge, “For
embarrassing me and getting me into an unfortunate situation tonight, I
dare Hayden to let me fuck him.” He pulled his towel off revealing his
quickly hardening big cock.
Riley knew he had to step in. “Come on, Todd, he’ll never get that
thing inside. He’s only just 5’ tall. He maybe weighs 100 pounds
dripping weight,” Riley was exaggerating for effect. “Your cock would
split him in half. Why not let him blow you or something?”
Todd was not to be deterred. Evan thought the little shit deserved it
and was excited to see how the small boy would handle an 8 ½
erection. Riley kept trying to talk Todd out of it. Hayden kept very
still as he watched everything unfold like a movie.
“I’ll do it,” Hayden suddenly found himself saying. Todd and Riley both
stopped arguing and turned to him. “Todd’s right. I was an asshole by
asking that. I knew it would piss Evan off and I did it because he
always picks on me. I didn’t mean to get Todd in trouble, but I was
also jealous. When I saw him in the bushes, and I only stopped for a
minute, it was because I was hoping to get with Emily. I’ve been hot
for her for a while, but she doesn’t give me the time of day. I was
going to find her to ask her out, but then I saw her and Todd going to
the bushes and I couldn’t imagine why she would be heading off with a
senior, so I followed them. And there they were, and she was sucking
him, and his cock was so big. And Todd could have any girl he wanted,
so why her? I was just so mad that I am so small and everyone thinks
that I’m a little kid. But I have hormones too and…” Hayden, realizing
he rambling, trailed off.
“You sure?” Riley checked with his brother. Hayden nodded and began
removing his clothing. Todd grabbed the hand lotion and began rubbing
it on his dick, which soon was hard and pointing straight out like a
missile. Hayden was naked by this time, having never restored most of
his clothing from earlier, his own small dick standing at attention in
anticipation. He rubbed hand lotion on his own ass cheeks as he had
seen Evan do to Todd.
“Come here,” Todd ordered. The teen moved to the center of the bed
where Todd told him to lie on his stomach with a few pillows under his
groin and another by his head. Todd split Hayden’s hairless ass and
added some lube. He took his pointer finger and pushed it gently into
the boy’s virgin rosebud.
“Oh, fuck!” Hayden cried.
Todd stopped and then looked Hayden in the eye. “This is going to hurt.
A lot. But then it will feel good. And then it will feel great. I won’t
lie. About any of this. I’ve fucked girls your size in the ass before
and I guess I know what the other side is like now too. Just grab a
pillow and scream into that. I’ll take it slowly, starting with my
finger, but I’m not going to stop.”
Hayden began to breathe easier after he got used to having three
fingers in his ass. It was also about how thick he imagined Todd’s cock
must be. But not nearly as long. Todd removed his hand and without any
warning, replaced his fingers with the tip of his dick, pushing it
about a third of the way.
Hayden’s scream was effectively muffled by the pillow he pulled into
his face. It almost looked like he was suffocating himself. Little by
little, inch by inch, Todd explored uncharted territory. It was so
unbelievably tight it was difficult to get in. “You have to relax
your ass muscles, Hayden. It’ll just hurt more if you don’t. You don’t
want me to do it like Evan did it to me, do you?”
Hayden breathed in several deep breaths. Tears had filled his eyes and
he was literally shaking. He nodded and Todd resumed. It went a little
easier, but Todd couldn’t get his entire shaft in.
“Let’s change positions.” Todd pulled out and flipped Hayden over.
There was a little blood, but Todd was too sexually charged to deal
with it. He pulled the boys legs up and told him to pull back his own
calves. Todd moved to his knees and with a better angle on the anus,
reinserted his dick. After another reminder to relax, Todd was able to
get a better motion. After a couple minutes, the senior was amazingly
pushing his entire dick in and out of the freshman’s tiny butt.
“This is fucking awesome,” Todd admitted. He began to understand his
own brother’s attraction to younger teen boys. They continued on for
several more minutes. “I’m getting closer,” Todd announced. He picked
up the pace using his strong legs to support his thrusts. Riley had
by his brother’s face whispering supportive things to him, telling him
he was doing great. Evan, meanwhile, was playing with himself, newly
erect from the live porno a couple feet away.
Hayden had trouble holding his legs up, so Todd told him to rest them
on his shoulders. With a better view of the young boy, Todd noticed
that he had not only stopped screaming in pain, but was looking rather
satisfied. He also saw the boy’s dick was completely hard. With one
supporting his balance, Todd used the other to reach forward and began
to stroke the boy’s skinny 4-incher while continuing to thrust.
Hayden’s breathing became intense with many short little breaths as he
felt pleasures that were nothing like masturbation. After only a couple
minutes into the handjob, Hayden ejaculated covering Todd’s right hand,
his own chest and face, and some of the bedspread.
The sight of Hayden’s orgasm pushed Todd over the edge. With his cock
still planted inside Hayden’s ass, he came repeatedly with a look of
Spent, he pulled out and collapsed on the bed next to the
sweat-and-cum-covered Hayden. They heard a quiet slow clap coming from
the arm chair. “You two put on a hell of a performance. Fuck me.
Mini-Me, I’d be happy to pay for the next showing,” Evan attempted some
wit as he put his own dick back in his boxers.
“Fuck you,” said Hayden as got up to go the bathroom and shower.
Suddenly he remembered something, stopped, and said, “I need a break
for a little while. Skip my turn, please.”
“You okay?” Todd and Riley both called after the boy.
He turned his head over his shoulder, smiled at Todd, and nodded. Then
he disappeared into the bathroom.
“That makes it your turn, Riley,” Evan noted naïvely.
“What are you going to dare?” Todd asked as he wiped himself with the
towel and began to put on some clothing.
“I think I’ll dare everyone to go to sleep!” Riley suggested.
“Are you ever going to get a chance like this again?” Todd suggested.
“I mean, no one is going to talk about tonight, ever. No one is going
to think less of you because we all are doing the same things.”
Riley got up and walked around the room. His dick ached from the last
two encounters he had watched. But what would he dare? “I am not going
to fuck my brother,” Riley thought out loud. “And I don’t think he’ll
be able to sit for a month.”
Riley began to pace back and forth. “Todd has already been fucked
tonight, but I could ask him to blow me. And Evan has already blown
me.” Evan nodded thinking that Riley was about to announce a blowjob
“Evan, I dare you to let me fuck you.”
After the expected moment of silence, Todd broke in first. “Evan, you
are Riley’s bitch! First he fucked your mouth and now he’s going to
fuck your ass. You are his sex toy, girlfriend.” Todd snapped two times.
“You are queer. I knew it.” Evan said. “I always thought you looked at
me funny. You love me don’t you?”
Riley talked matter-of-factly. “Watching you fuck Todd and Todd fuck
Hayden got me horned-up. I want to fuck someone. I can’t fuck myself. I
can’t fuck my brother. And why shouldn’t I get to break someone’s ass
cherry tonight too? Everyone else has. That is, unless your ass isn’t
“Fuck me!” Evan responded as usual. It took a minute for him to
understand why Riley and Todd both burst into laughter. “I mean fuck
They let the quiet fill the room. They only heard the shower running in
the bathroom. Riley broke the stillness. “Evan, just for tonight, and
just this once, I dare you to let me fuck you. Just like you fucked
Todd. And just like Todd fucked Mini-Me.”
It didn’t take long for Evan and Riley to both be naked and lubed up as
best they could with crappy hand cream. Riley wanted to fuck Evan
doggie style as he had fucked Todd. Looking at the muscular body of his
friend, there was no doubt he was looking at a guy. He couldn’t fool
himself – not with the tight muscles, wisps of blond hair all over, and
that cock hanging between his legs. He was fucking a guy – his best
friend, in fact.
Riley thought of all the times Evan had gotten the girl. How many
parties where he had to entertain the ugly friend or the fat one or the
awful cousin. Granted, those girls had low self-esteem and were usually
easy to get some action from. But he wanted to get the hot one. He
wanted first choice sometimes. He wanted it to be “Riley and Evan”, not
“Evan with his little friend Riley.”
The blowjob from Evan had been surprising. His friend had gotten into
it and it was so hot cumming on his face. But this, well, this was
something more. This was a chance to get out some of his aggressions
and then let it all go.
“Oh, fuck that hurts!” Evan yelled as Riley entered him. They shushed
him to be quiet and Riley continued pushing forward. “Slower!” Evan
begged. But Riley thought he should see what all those girls felt from
the backdoor experiences from Evan. While Riley’s dick was a full inch
shorter than Evan’s, and skinner as well, Evan couldn’t believe how
much it felt like someone was ramming their whole arm up his ass. Maybe
he’d take it a little slower with the next girl’s Hershey Highway.
Riley quickly established a beat, thrusting in and out. His hands were
resting on Evan’s ass cheeks for balance and his knees gave him the
force to push He wondered how long he could go, how long
before his scrotum took over and forced him to cum. He would love to do
this all night.
“Holy shit!” Hayden had walked into the room, fresh from the shower, a
towel around his waist. He was stunned to discover his brother plowing
his brother’s best friend. Wow, if only I had a camera, Hayden thought.
Imagine showing this to all those girls that worship at the dick of
Evan. He felt himself getting hard again.
Todd had moved to the armchair and sat there open-mouthed. He hadn’t
imagined what it looked like as he was being fucked and fucking. Todd
had been at parties where he had seen his share of people having sex in
all sorts of ways. But never had he been so close, so able to just
stare. Never had he seen two guys, two hot guys, go at it with such
fervor. And it was surprisingly sexy.
“Harder!” Evan called out. Suddenly Riley pulled out. Evan opened his
eyes and turned to find out what was happening.
“Turn over,” Riley told him. Flat on his back, Evan’s legs bent at the
knees and wrapped around Riley’s sides. Staying on his knees, Riley
pushed back into Evan’s anus with one hand supporting him on the
mattress and the other pushing off Evan’s left leg.
They all could see Evan’s cock was standing up straight as Riley
continued to push. Riley leaned forward so he was practically face to
face with Evan. From the side, it almost looked like Riley was fucking
a girl in the missionary position.
“I’m…not…mad,” Evan said to Riley.
“I had to do it,” Riley responded as he increased his
thrusts. Riley then tensed up and pulled himself back up. Pulling out
of his friend, he grabbed and stroked his cock a couple times before he
shot forward all over Evan. Riley looked exhausted, but he then
surprised everyone by grabbing Evan’s still hard cock and jacking it.
After about a minute, Evan too shot all over himself with a low moan.
“Fuck me,” Evan muttered to himself covered in his and Riley's splooge.
“When you insist,” Riley joked.
Evan was next to take a quick shower while Riley wiped off the sweat
and jism that remained. He’d jump in the shower when Evan got out.
“Wow, some night,” Evan said to no one in particular.
“We’re not done,” Todd responded.
“What?” Riley asked, confused.
“It’s Hayden’s turn.”
Hayden was still standing with a towel around his waist and a small
tent in the front created from his erection.
“Hayden gave up his turn,” Riley said.
“Hayden said he needed a break to shower,” Todd countered.
Just then Evan came out of the bathroom, drying his hair, a towel
similarly wrapped around his waist.
“Evan, what did Hayden say when he went into the bathroom before?”
Riley asked him.
“’I have to take a shit?’ How the fuck would I remember?” Evan
the question as he put his Cardinals cap back on.
“He said, ‘I need a break for a little while,’” Todd declared.
“He also said, ‘Skip my turn,’” reminded Riley.
“Wait a minute,” Hayden interrupted everyone. “I know what I said and
what I meant. I needed time to breathe and shower and think. I couldn’t
just keep going. You all may have experiences like this all the time,
but this is a new one for me. I had a tree trunk up my ass and was
filled with cum and blood and shit. So I said I wanted to skip my turn
meaning we’d come back to it later. Now it is later!”
Todd waved his hand as if saying, “Exactly!”
“What do you think Evan?” Riley looked for support. “His dare could
affect you too.”
“I think he’s a little pipsqueak Mini-Me. But I also think the three of
us got a turn, so he should too.”
With the vote 3-1, Riley conceded. “Who do you dare?” Riley asked him.
Hayden wasn’t one for big drama. He was too nervous with what he had to
say. “Well, I thought about Todd – having him blow me or me fucking
him, but I think we’re done and should move on.”
He gained a little confidence as he saw Todd’s eyes light up in
anticipation of where he was heading. “I would really love to get back
at Evan for being such a dick to me all the time. And he made me suck
him before. So it’d be great to have him return the favor.”
“So, your dare is for Evan to suck you?” Riley asked, misunderstanding
the nuance of Hayden’s statement.
“No, Riley. That’d be so boring and obvious. Tonight is a chance to be
totally crazy and different. You just had sex with your best friend. If
I had told you that yesterday, you would have beaten the crap out of
“And I would have killed you…yesterday,” Evan added.
“So, my dare, I guess this is the final dare of the evening. Riley, I
dare you to let me
There was no moment of silence this time. Todd let out a satisfied,
‘yes.’ Evan broke into a mischievous smile. Riley simply said, “No way.”
They got into a long argument. Todd advocated for fairness. The other
three boys had been fucked, why was Riley different? Riley, Todd, and
Evan had gotten to fuck someone. Why not Hayden? Evan simply said it
would be a good brotherly thing to do. While he wasn’t bitter or
regretful over his recent fuck by Riley, or even the blowjob he had
given him, this is seemed like…oh what was the word on that TV
show?...karma. Riley told them all he was not fucking or getting fucked
by his own brother. A guy was crazy enough, but not his little brother.
Hayden said nothing for a while. He saw the clock now read 2:41 a.m. He
was getting tired. He had cummed twice – from his brother’s blowjob and
Todd’s handjob. He had blown Evan and been fucked by Todd. And he had
been in sexual terror or ecstasy all night – sometimes both
simultaneously. He wanted to finish it.
“Riley,” Hayden spoke up. “You always tell me that you have to play by
the rules. Well, we set up rules in this room. So, whatever the rules
might be out there,” he gestured to the window, “in here, we are
playing by all different rules. And one of those rules is that we each
take turns and we all do what we are dared, even when we don’t like it.
I guess you have just been full of shit up ‘til now. I guess I should
never believe you on anything you promise or say.”
Evan was certain Riley was going to punch his brother. Riley came right
up to his little brother and looked down at him. “Get me the lube.”
It didn’t take long for both boys to be ready. Riley looked like he was
about to face a firing squad. “What position do you want?”
Hayden had thought about this while in the shower earlier. He only knew
about anal sex from the internet, but having seen a few positions in
person now, he wanted to look cool and try something different. He
moved to the bed, lay back onto the pillows, his dick standing straight
in the air and said, “Sit on it.”
Lowering himself onto his brother’s dick, Riley realized he probably
should have loosened up first. He was extremely tight as he pushed down
on the skinny, but firm cock. He stopped and started a dozen times.
“Get going!” Evan said.
“Your brother took a dick more than twice that size. You can’t take
his?” Todd taunted him.
Determined, Riley bit his lip and forced himself all the way down,
resting on his bent knees, facing in the direction of his brother.
“Uhhnhh!” Hayden grunted in bliss. Slowly, Riley began the work of
moving up and down. When Hayden began to thrust, it was too much. “Not
yet…” Riley cautioned.
It took a little while, but Riley began to loosen up and seek out the
pleasure in the situation. He tried not to think that this was his
little brother below him, but looking down and seeing a younger version
of himself almost made him feel like this was some masturbatory sci-fi
“Lean back,” Todd recommended. The pleasure increased for both boys as
Riley rested on his arms stretched out straight behind him onto the
mattress. Quickly, Riley also got hard. For whatever reason, he was
embarrassed to sprout an erection over his brother’s stomach, but
Hayden was delighted that this was pleasuring his brother too. He
grabbed hold of the pulsing member and began to stroke it.
“Oh!” Riley surprised himself by calling out. When he was with a girl,
his dick was in her and so it was always a singular sensation. But with
the pleasure also coming from behind, he was now getting a double
sensory experience. And he liked it.
Hayden rubbed his brother’s cock with delight. He knew this was it –
one night never to be mentioned again. But he had achieved fantasy far
beyond any possibility – his brother had been his sexual servant
“My knees are hurting,” Riley reluctantly told Hayden. Years of tennis
had left Riley was mediocre knees.
Hayden thought for a minute and then told his brother to get off and
lie down. Riley did so, moving onto his stomach.
“No, on your side,” Hayden corrected. The smaller boy moved behind him,
the height difference apparent as Hayden’s head was in line with
Riley’s shoulders. From behind, he pushed his still rock hard dick into
his brother. It took a couple tries before both boys had their knees
bent properly – it worked best when Riley lifted his top leg – but
Hayden was able to insert himself fully and thrust with slow intensity.
Once Hayden was back in rhythm, he reached around and began to jack his
brother’s cock again. For several minutes they stroked and thrusted
before Hayden decided to go for it all. “Turn a little towards me and
keep your top leg bent.” The 14-year-old had shown all night that he
had a strong intuition for sexplay.
Riley leaned towards Hayden putting their faces almost in line. With
his right hand stroking his brother’s dick, Hayden pushed up and gave
his brother a kiss. Riley didn’t respond at first. But in the second
kiss, he let his brother’s tongue enter. In the third, he responded in
kind, grabbing Hayden’s head from behind and for the next few minutes,
Riley was being stimulated by his brother’s cock in his ass, his
brother’s hand on his dick, and his brother’s tongue in his mouth.
Neither Todd nor Evan could fully comprehend what they were seeing.
Both boys had recognized that Hayden, with no sexual experience, was
somewhat fearless in his explorations. He also was a natural – blowing
Evan with skill and receiving Todd’s big dick in a way to make it
pleasurable. Now, he was showing more natural instinct in how to fuck
someone in the ass and make it a mutually enjoyable experience. That
Hayden was doing it with his older brother wasn’t even their concern.
It was Riley’s. He was in heaven physically. But emotionally he felt a
mess. There would be ramifications of this. Of the whole night. While
Todd might walk away easily, heading off to college in a few months,
Riley spent nearly all his waking hours in the company of either Evan
or Hayden. How could they forget a night like this? Really, Evan had
been Riley’s bitch tonight. And Riley had been Hayden’s! And Hayden,
who had come in having done little more than feel a girl up, had sucked
and been sucked, fucked and been fucked. And all with guys.
But before he could dwell further, he recognized that his brother’s
actions were having their intended effect. With a quick command to
“stroke harder,” he let his brother be only the second guy ever to jack
him off. The cum shot, his third of the night, shot across the entire
Hayden was thrilled with the results. He continued to kiss his
brother’s neck and shoulders as he let go of his spent dick. Riley was
using his right hand to
caress Hayden’s arm, shoulder, back, and even ass. “I wish this wasn’t
just tonight,” Hayden whispered out loud.
His body then kicked into natural high gear as he thrust with vigor and
shot off inside his brother’s butt without making a sound.
They lay there, in each other’s arms. Hayden unwilling to move, his
flaccid cock still pressing against his brother’s butt, their arms
intertwined. When it became obvious that the boys weren’t moving for
the moment, Todd got up and pulled the bedspread off the other bed and
turned off the lights. He and Evan each slipped into the bed on their
separate sides – the game over, normal heterosexual rules applied. They
both surprisingly fell asleep quickly.
Riley began to get a little chilled. He also had semen leaking out of
his ass. He pulled free of his brother and jumped in the shower.
When he returned, the muted TV was the only light in the room. Hayden
had thrown the cum-covered bedspread in the corner and slipped naked
sheets. Riley decided to do the same. He dropped the towel and slid in
next to his brother. They hadn’t shared a bed in years. But after Riley
rolled to his side to fall asleep, he felt Hayden’s arm reach across
his chest and his skinny frame push up against his own.
None of them knew what the dawn would bring. But for tonight, brothers
Riley and Hayden spooned naked under the sheets in room 1012.
Check out my other stories:
Pledge Class – The Blow Job Task
in Bisexual:College) – Five
fraternity pledges are given their final challenge: Give each other a
blowjob or get their girlfriend or sibling to take their place (7
parts, last post 1/15/06)
The Sex Life of Zack and Cody
(Found in Gay:Celebrity) – Zack and Cody
Martin discover they have more in common than just being identical
twins one afternoon in their suite. (posted 2/24/06)