Note: This story series
includes depictions of gay sex, straight sex, bisexual sex, sex between
college students and high school students (both male and female), and
incest. If that's not your thing or if it is illegal for you to read
this story, then stop. This story is made up and does no depict
anything true.
Comments, suggestions, and helpful feedback are welcome. -
DerekGuy17@gmail.com
Recap: Five freshmen have a
final pledge task to blow each of the other 4 pledges on successive
nights. Austin got his High School sister to be his substitute on the
first night. Chet got his older sister to do so, but in return was
fucked by her boyfriend. Nick reluctantly got his longtime girlfriend,
but she got to fuck two of the other pledges in return. Only an
exclusive girlfriend or a sibling can sub for the pledge himself.
Pledge Class – The Blow Job Task
Part 5 - Dylan
Sunday Night
Dylan begged and begged Mia to do it. Despite being an all-star athlete
with girls hounding him, since they began dating in the third week of
college, Dylan had remained exclusive with Mia (if you didn't count the
hags of last week). His fuck date with Skye was still four days away.
Mia refused and told him he was a pig and if that's the kind of
fraternity he was in, she wanted no part of it. He quickly told her he
was joking the whole time and she dubiously believed him. But she
wouldn't talk to him anymore.
Monday
Dylan loved his sister Desiree and had trouble thinking of his
17-year-old sister sucking his friends. She wasn't a sexual person and
he didn't remember any longtime boyfriends. He called her Monday
afternoon and tried to bring up the subject of sex. Two years apart in
age, they really didn't know each other. Dylan had always been busy
with sports and then sex. He didn't have time for younger siblings. The
conversation got nowhere fast. It was pretty obvious she was a virgin,
and after he somehow worked blowjobs into the conversation, he realized
she had never blown anyone before.
Was he going to have to suck his friends himself? His girlfriend had
refused. And his sister likely couldn't do it even if he somehow
convinced her to try.
Wednesday
After Tuesday's pleasuring by Austin's sister, Dylan tried one more
time to convince Mia. Before he finished his first sentence she kicked
him out of her dorm room and told him to fuck off. What the fuck do I
do now?
Thursday
Dylan had convinced himself he'd have to get Desiree to do it. It was
unfair and wrong, but he didn't have any other choice. With Jess and
Sam already having fulfilled their brother's turns, he knew he needed
his sister to do the same for him.
Dylan skipped classes and borrowed a car to drive four hours home to
see what he could say to her in person. Maybe he could get her to
practice on a couple guys that day. And what he could he give her in
return? What would she want to make this bargain? What the hell…how
could he think of his sister this way – like a piece of meat. He was
thinking irrationally - he had never considered Desi as a “girl”
despite her good looks.
Within 30 seconds of entering his home he discovered it couldn't work
no matter what. Not only was Desiree incapable of blowing four strange
guys, but she also had come down with the flu and was in bed with a
high fever and frequent vomiting.
"Fuck!" Dylan grimaced.
"And fuck you too!" he heard. He turned around to see "Little Dylan."
Dylan's younger brother Doug was a smaller version of the original.
Having just turned 16, he had also finally reached 6' tall. Doug had
the same piercing blue eyes as his brother and retained the soft, baby
skin of youth. Not nearly in the same class of athlete as his brother,
his body was well defined, but he hadn't added enough bulk on his
muscles. The raw material was there, he just hadn't come into his own
physically or spent as much time in the gym as Dylan had.
Doug idolized his brother, but also resented his brother's athletic
success somewhat. Dylan found Doug to often be a nuisance, but they
generally got along. Dylan's opinion of his younger brother had
improved somewhat just over a year ago. The night of Doug's 15th
birthday, he found the high school freshman in bed with two sophomore
girls. Dylan hadn't had two girls at once until he was a junior. Doug
was clearly straight and Doug seemed to always be on the make.
Wait a minute, Dylan thought as he greeted his brother. Am I now
considering having Doug do the blowjobs? I'm losing my mind. And
anyway, even if he could ask Doug and even if Doug agreed - what would
the guys say if he brought his teenage brother as his substitute? This
task was going to kill him.
"Dylan, what the hell are you doing here?" Doug asked.
"Why aren't you in school, Dougie?" Dylan barked.
"Don't call me that, dickwad. I'm playing nurse, watching Desi. Dad is
off in London and Mom had to run to Dallas on an emergency business
trip. I volunteered to watch her. We don't need grad students to stay
with us anymore 'cause you're not around to fuck them. But Desi's
pretty self-reliant – she vomits without any help – so it's been a
pretty free day."
Dylan avoided explaining his presence as the two boys chatted about
life, school, and girls.
"Wanna smoke?" Doug asked. Dylan was safe from any drug tests for the
baseball team for a while, so they went up to Doug's small bedroom and
Doug loaded up his bong. Dylan had a much bigger room filled with
trophies that he refused to vacate when heading to college despite a
request from Doug. Dylan wasn't a big pot smoker. Doug seemed to be
heading towards becoming one.
The 16-year-old took huge hits off the bong, while his 19-year-old
brother held back and remained a bit sharper, although the edge was
gone from his voice. As they smoked more and more, the conversation got
looser and freer.
Having some shared embarrassing stories of their sexual adventures,
Dylan turned the conversation in another direction. "Have you ever
fooled around with guy?" Dylan asked
"What…do…you…mean?" Doug choked out as he let out smoke from his lips
with each word.
"Have you and a buddy ever jacked each other off or something? Lots of
guys do it. In sports they do it all the time."
"Have you?"
"Of course!" Dylan admitted trying to sound nonchalant. Actually, until
the previous night, he had never touched a guy or been touched by one.
His and Brandon's mutual jack-off was a new experience. But now was no
time for the truth. "Happened with a some baseball buds in High School.
We were all drunk and I jacked this guy off. Then another bud sucked me
off." In truth, although Dylan had always checked out other guys,
mostly confirming he had the biggest cock, he had never thought much
about being sexual with a guy.
"You were blown by a guy?"
"Yeah. It felt the same as a girl. In some ways better…And I sucked him
too," he hastily fibbed. If he was going to get results, he'd have to
take risks.
Doug was silent for a while. "Wow! I never imagined that you…I thought
you…well, this one time I saw you and this girl together in the living
room. And she was, well…" Doug was remarkably nervous. "She was giving
you head. And it was really hot and looked so good. And Will was here
too and we both went back to my room and then we…well, we were so
turned on and so, we…we sucked each other. I never thought you had…I
was worried it made me gay."
"Was that it?" Dylan asked, trying to hide his excitement that he might
have found a potential substitute.
"Yes. I mean…no. Will and I kept doing that for a while and we tried
some other stuff. But we were just kids then." Will Turner was Doug's
long-time best friend. "And, I guess I've done stuff with some other
guys too. But no one has ever fucked me. You know I'm not gay. I am
with girls all the time. But sometimes, when there isn't a girl around
or I just want to do something different, I mess around with a guy."
Dylan found his cock began to twitch at his brother's revelations.
"Doing stuff with a guy once in a while doesn't mean you're gay." Dylan
had no idea what he was saying, but he had an opportunity he wasn't
going to pass up. "Listen," Dylan tried to get his brother's hazy
attention. "I need your help. The biggest favor ever. I need you to
drive up to my college tomorrow night. And then, as part of my
fraternity pledge task, I need you to suck off each of my four frat
brothers."
Doug said nothing and took another bong hit and let the smoke exhale
from his lungs before responding. "Ha ha ha. You're shitting me,
right?" He couldn't believe his brother's words. But the piercing blue
eyed stare told him that this was the truth. Quickly Dylan recounted
the nature of the task, the rules, Mia's refusal, and the real reason
he came home.
Doug sat quietly for almost two minutes before finally responding.
"Okay. I'll do it. But it is going to cost you. For each guy I suck, I
get one thing from you. Non-negotiable."
Dylan knew his brother would relish having this power over him. But
what choice did Dylan have. The favors couldn't be worse than Dylan
having to do the sucking himself. "Tell me what I have to do."
Doug thought quietly again for few minutes as he continued to smoke,
mulling various possibilities, rejecting others. Finally, he was ready.
"Here they are. Non-negotiable!
Number 1: Get me laid with a hot sorority chick while I am up at your
college.
Number 2: I want you to trade bedrooms with me.
Number 3: I want you to suck me right now.
Number 4: When we are all done tomorrow night, I get to go back to your
dorm room and fuck you."
His brother was gay – or
least bi! Dylan observed in shock. And what kind of twisted requests
were those? "Fuck you!" Dylan said to his brother, trying to remain
strong and negotiate some options.
"What are your choices, LynLyn?” Doug used their parents baby nickname
for Dylan. Dylan hated it. “You can suck four cocks or one. Desi isn't
in any condition to help out - and she's a lesbian anyway." Dylan
blinked as things began to make more sense. He was learning a whole lot
about his siblings this visit. "Your girlfriend won't help you out
either. Is it the fourth condition? We can wait and see about that one
- I might want something different by tomorrow night."
Without waiting for a response, Doug unzipped his pants and pulled out
his already hard 16-year-old 8" cock. Clearly he was going to resemble
his brother in one other way. It was skinny and long, but the head was
large and oversized. Unlike his brother, Doug was circumcised, an
unexpected change of heart by his parents in the 3 years between them.
Dylan nodded in appreciation of his brother's well-formed cock. He
looked into his brother's face and saw his own piercing blue eyes
staring back at him. He had to admit, his brother was cute.
Dylan took in a deep breath and realized that sometimes you had to do
crazy things to find success. One was better than four. He leaned over
and tried to take his teenage brother's cock in his mouth. The position
was awkward and he couldn't get a good approach from where he was
sitting. Dylan hopped off the bed and onto his knees in front of
his brother. There he had better access. He took the oversized head in
his mouth and began to move up and down on his brother's staff. It was
so smooth and the skin was so soft. But the rod was iron hard and
seemed to be getting even harder as Dylan worked on it.
"Watch the teeth," warned Doug as Dylan had done so many times to other
girls. Dylan thought about the expert suckings he had gotten from Jess
and Sam the past two nights. He tried to copy their actions. He knew he
was unprepared to swallow more than a couple inches of his brother's
skinny tool, but he could still do a bit with the head, shaft, and
balls. With the bong hits having removed most of his anxieties, Dylan
dove into his task with surprising enthusiasm. He had never thought
about being with a guy - let alone his brother - but there was
something primal and fulfilling about making Doug write and moan. He
understood the power one had over a boy when you took his cock in your
mouth.
"I'm going to cum!" Doug cried. Dylan pulled off and used his hand to
jack his brother. "Oooooo…Oooooo….Oooooo…" Doug moaned and then with
great force jerked his hips as he shot right into his brother's face.
"Fuck, Doug!" Dylan muttered as the semen poured out in gushes
continuing to make a mess on Dylan, Doug's legs, the bedspread, the
floor - everywhere.
"That was fucking awesome!" Doug shouted as he dropped backwards onto
the bed. "And I knew you were lying before. You've never sucked a dick
before. I'm not stoned enough to know when you are talking crap. If you
had done it, you wouldn't need me to do it for you.”
Dylan wiped the cum out of his eyes and lips. The taste wasn't so bad,
but he wasn't planning on developing an affection for it. Was that what
he had done to so many girls? "Be at my dorm by 7pm on Friday and we'll
finish the rest of the deal. And go check up on our sister. I think I
hear her throwing up."
Friday Night
"Get the fuck out of here!" Austin shouted.
"The rules say that I can provide a substitute. A girlfriend…"
"So where's Mia?" Chet asked.
"Or it can be a sibling." Dylan continued. "So, here is my substitute."
Wearing a high school baseball jersey and jeans, Doug looked like a
tall typical suburban teenager. His moppy brown hair was uncombed and
his cheeks were devoid of any stubble or growth. The four freshmen in
front of him stared in disbelief.
"This is my brother Doug. He's straight, but has agreed to be my
substitute."
"No fucking way," Austin voiced.
"The rules clearly say a sister or a brother. If you don't like it, you
can drop out of the pledging." Dylan was getting defensive, worried
they would somehow challenge his plan.
"He's right," Brandon noted. Brandon had re-read the task rules so many
times that he knew them word-for-word.
"Who's first?" Doug spoke for the first time, bored of the standing
around.
It was Nick's turn to go first. He undid his belt and dropped his
pants. He cock was flaccid and he had a pained look on his face. Nick
hadn't spoken to anyone since last night's event. They wondered if he
even could get hard.
Doug pulled off his baseball jersey revealing a "Do You Know Where Your
Girlfriend Was Last Night? I Do?" t-shirt - perhaps the worst possible
outfit he could have chosen. "Take off your shirt," Nick ordered.
Misinterpreting the motivation of Nick's request, Doug smiled and
removed his shirt showing his hairless, trim body. He moved closer to
Nick and pulled off his shirt. The high school student leaned in and
started to suck on Nick's left nipple. The other boys were shocked by
the sight of the two beautiful boys together. After a few moments of
nipple rubbing, Nick pushed Doug onto the floor and repeated the
position of Wednesday with Sam. His still limp dick was forced into
Doug's mouth and Nick began to move back and forth, speeding up with
each stroke. His dick started growing to full size. Doug was totally
turned on to have a cock harden in his mouth and tried to relax his
throat to take in more of Nick's 7 inches. But Nick was angry and was
taking it out on the poor boy. He grabbed Doug's head and forced his
cock all the way in his mouth. Doug was having trouble breathing and
started to gag when Nick shot into his throat. He dumped his load of
resentment and anger into Doug's mouth and then as quickly pulled out,
walked away, and pulled up his pants.
"I'm sorry," he mumbled to the coughing boy as Brandon gave him
something to drink.
Austin was next. The violence of Nick's face-fucking had kept the other
boys from getting excited. Doug pushed him onto the couch and kneeled
between his legs – the same position Dylan had sucked Doug the previous
day. Taking out Austin's limp dick, Doug began to rub it gently with
his hands. Soon he was covering the head with little kisses and then
took his balls into his mouth. Austin had never been with a guy in any
capacity until Nick jacked him on Wednesday. The boy was cute, but
Austin simply didn't swing that way.
Austin leaned back and closed his eyes. He tried to pretend it was a
famous hot girl blowing him and settled on Natalie Portman. Doug had
talent and it wasn't long that fantasy, tension, and his efforts had
Austin shooting into the boy's mouth as Austin cried out, "Natalie!" to
much embarrassment.
"Your bro'z got skills!" Chet remarked as he beckoned Doug towards him.
With their height difference and his own sexual confusion earlier in
the week, Chet wanted to be blown standing up. Doug crawled on his
knees over to the older teen as Chet removed his pants. Doug helped
with the his underwear, shoes, and socks, leaving only a college
football t-shirt. Chet was already hard and Doug dove right in.
Dylan was surprised as to his brother's skills. Cleary he had done
quite a bit of that "messing around" with other guys. Chet was already
grunting and pushing his pelvis forward. Chet asked Doug to slow down
and make it last longer, but the boy knew he had another guy to go and
kept up the speed. Doug's in charge, he thought, not Chet. Unhappy as
being made to cum so quickly, Chet decided to pull out and shoot
directly in Doug's smooth face and chest whooping like a rodeo cowboy
as he sprayed onto the boy. Doug much preferred swallowing than having
all this cum on his body and raced off to the bathroom to clean up a
little pissed off.
Brandon was last. He was still fully clothed. Doug immediately thought
this was another Austin - reluctant and needing help. But as he began
to undress Brandon, he felt the boy's ample cock pushing at the fabric.
Brandon had been incredibly turned on by the sight of the two hairless
teens, Chet and Doug, going at it. He worried if he even touched his
own clothes, he'd have already shot multiple times now. Doug was a
perfect "little Dylan," but with a better sense of humor, a bigger risk
taker, and a zest for life.
Doug looked directly into Brandon's face. He recognized passion and
hunger. Brandon wanted him so badly. He stared into Brandon's hazel
eyes. The baby blues of Doug's corneas was captivating to Brandon and
the boys suddenly were kissing, tongues slipping past each other's lips
with powerful desire. Chet and Dylan, who usually made gay cracks for
the slightest reason, restrained themselves. They had each jacked off
Brandon in the past two days, and had each been with another guy this
week, so they were in no position to judge.
As Doug kissed Brandon's neck, he saw his older brother staring at
them. He recognized desire there too – although it was more buried. He
needed to make this particularly hot. He stripped Brandon completely,
but left the remainder of his own clothes on. Brandon tried to head to
the couch as he had the past three nights, but Doug wouldn't let him.
Standing the 19-year-old in the center of the room, he proceeded to
lick him from head to toe and then to head again.
Dropping on his knees, Doug kissed everywhere around Brandon's
throbbing tool. But he didn't touch his dick at all.
"Suck it!" Brandon begged. Doug ignored him and moved to his rear. He
spread the tight cheeks and used his tongue to moisten his fuckhole.
“Holy shit!” Chet gasped in admiration, jealousy, and surprise.
As Doug rimmed him, Brandon shuddered in sheer ecstasy. "Please…suck
me!"
Moving between his legs, Doug attacked his scrotum. Brandon clearly
shaved his pubes and balls, so it was no problem to take each ball in
his mouth and work it over. It was deadly silent in the room. All the
other pledges were staring in amazement at the delayed pleasure this
teenager could bestow.
Finally, and without warning, he swallowed Brandon's cock. He knew he
didn't have long, so he deep-throated it quickly and used his tongue to
stimulate it to climax.
"Aaaaaaaahhhhhhhaaaahhhhhhh! Ahhhhh! Ahhhh!" Brandon shouted at the top
of his lungs as his sticky seed shot down the boy's throat. Doug let
the cock settle in his mouth and then slowly pulled off. He gently
licked the entire shaft to cleanliness. Standing up, he looked into
Brandon's hazel eyes and the planted an open-mouth kiss returning some
of the cum back to its owner via their tongues.
Doug stepped back, smiled, and then grabbed the bottle of water to
clear his mouth. Dylan nodded appreciatively at his brother for his
efforts and for this incredible show. He had forgotten the three
remaining promises. But Doug hadn't.
Doug broke the continued silence and looked at his older brother. "I
want to make a change in my conditions. I am dropping the claim on your
bedroom for something else." Without waiting for a response, Doug
dropped back to his knees and pulled down his brother's jeans. His
hardon was amply evident through his briefs and Doug yanked them down
as well. The huge cock began to come to full 10 inch strength and the
teenager wrapped his mouth around the head and bathed it in saliva. He
didn't want to give Dylan a chance to think too much about what was
happening. As he got a clear physical response from his brother, Doug
finally released his own 8 inches out and began stroking it hard.
The boys had seen both Austin and Chet blown by their sisters. But
watching this boy with his own hard large dick blow his brother was
transfixing. Brandon and Chet moved towards each other and wordlessly
began to repeat their actions of the previous night stroking with
deliberate intent.
Austin and Nick were sitting on the couch. They had both long ago
recovered from their own blowjobs and Austin began to play with himself
as he watched Dylan and Doug go at it. Nick was sitting, still tense,
next to him, his cock hard despite himself. For the first time in his
life, Austin reached over grabbed his friend's hard-on and began to rub
it. "Let me make things up to you…" he whispered. Nick said nothing and
let his roommate proceed. It was a lot like masturbation, Austin
thought, but he's getting all the pleasure.
Dylan was so confused. His brother was an amazing cocksucker. His
friends were all fine with it. Each of them was hard. He saw Austin
stroking Nick, and Chet and Brandon going at it. Brandon sure got it up
quick. Two days ago, he would never have believed any of this scene.
Dylan stopped Doug long enough for both to remove the rest of their
clothing. Seeing these two boys, so similar in body and face, gain
pleasure, one from the other surged electricity through the four
pledges. Chet shot first under Brandon's guidance. Nick then exploded
onto his own chest. After a brief pause, Chet put extra focus on
Brandon's cock and he made an additional mess on the carpet. Austin,
stroking himself, continued to gaze ahead.
Dylan usually took a while to cum when being sucked. Tonight was no
different. Doug used the technique he had also learned from the same
grad student who taught it to Dylan – he stuck a finger up his
brother's butt. Before he understood exactly what had happened, Dylan
shot into his brother's mouth. The volume was too much and the boy
pulled off receiving the rest of the gusher in his face, hair,
shoulders, and chest. Austin immediately shot upon seeing this onto his
own legs and the carpet.
Although he had yet to orgasm himself, Doug stopped stroking his own
dick, prepared to have more interesting action later that night. As the
boys cleaned up the mess of their cum on their bodies and on the
carpet, clothing, and couch, Doug broke the quiet by shouting to Dylan,
"Where's my hot sorority girl to fuck?"
Dylan had gotten Chet to find someone for his brother without
explaining why. Mindy Simmons was an easy lay and had traditional
slutty college girl looks – blond hair, pretty face, and big breasts.
Chet and Austin had both been with her. She had a total thing for
Dylan, but he had been off limits. Chet had told her that Doug was
Dylan's fraternal twin and set up the date. Doug eagerly departed for
his college girl action.
While actual "date" events had been planned, within 15 minutes of
meeting they were making out in the car. 10 minutes later, they were
back in her dorm room having loud, sloppy sex.
Late that night, Doug slipped into Dylan's dorm room.
"How was it?" Dylan muttered from his sleep-like state.
"Fantastic. My first undergraduate…girl." He had never told Doug about
the grad student that had both experienced.
"How many times did you do it?"
"Twice. I came pretty quickly the first time, as you might guess. Then
we did the second time slower doggie style."
Dylan's roommate and former pledge brother Jared was spending the night
with his girlfriend to give Doug a place to sleep. Dylan yawned and
fell back asleep. Doug undressed completely but headed for Dylan's bed,
lifting the covers and crawling into bed with him.
He pushed his semi-hard cock up against Dylan's backside and rubbed it
against the boxer-briefs. His right hand began to massage his brother's
rock solid chest. His kissed his brother's neck and shoulders.
"What the fuck are you doing?" Dylan barked.
"Cashing in on the final part of my bet. Last part. Take off your
underwear. I'll do everything else. You just need to relax"
"I'll give you my bedroom at home and then we're done. You got
everything else."
"No. I get this. I know you are stronger than me and I can't force you
– and I wouldn't want to. But I also know you never break a promise or
a deal," Doug explained.
"What if I blow you again?" Dylan offered.
"You liked having my finger in your ass. You're going to love my cock,
LynLyn." Doug reached and down and got some lube from his bag. He
liberally spread it on and put his hand into his brother's briefs to
spread it on is ass.
"Make it quick." Dylan finally accepted as his brother massaged his
fuckhole.
Doug didn't listen to his brother. He knew he had to go slow at first.
His brother was a big guy, but 8" couldn't just be rammed in. He
had broken enough cherries to know what to do. Doug got his
brother into a more accessible position and introduced him to the
pleasures of guy-on-guy fucking.
Under oath in court, Dylan never would have admitted how much he
enjoyed that night. His brother was gentle and was damn good too. The
forbidden qualities – he's a guy, he's my brother, he's too young, he
probably should be wearing a condom – all set off huge warning bells
that normally would have stressed Dylan to no end. Tonight, they seemed
to only add to the pleasure.
It didn't take Doug very long to finish. His grunting and moaning
during the fuck, and especially as he shot up his older brother’s ass
probably woke half the dorm hall. They both collapsed in sweat and
exhaustion onto the bed. As they spooned, Doug discovered one thing was
still awake.
"You got hard from my fucking you. That's awesome." Doug began to
stroke his brother's long cock from behind, gently rubbing from top to
bottom. He took his time as his brother unsuccessfully tried to fall
asleep. Dylan would have to shoot to be able to sleep.
"Faster. Harder." Dylan encouraged his brother. Doug kept his slow,
deliberate pace.
"Dougie, if you don't make me shoot soon, I will beat the living hell
out of you."
Doug laughed and complied, jacking his brother with such force that he
nearly ripped the skin until Dylan shot all over the bed. Doug makes me
feel so good, Dylan thought, as he accepted his brother’s open mouth
kiss.
They both got up and slipped into Jared's bed, spending the night
completely naked and comfortably wrapped tightly in each other's
brotherly arms.