Date: Mon, 06 Dec 2021 10:25:46 +0000
From: Mr Dolby <greenmms@protonmail.com>
Subject: Elliot's Education

This story is complete fiction, a product of the author's imagination.
Any resemblance to real persons, locations or events is purely
coincidental.

Note to the reader:  This story is based on the main character in the
short story "His First Confession" by Luke0111 (published on another
website).  This continuation is written with his permission, and stands
alone when read independently.

Also note, if you are very sensitive to religious symbology used out of
context for humorous/literary effect, this may not be the story for you.


Elliot's Education
(working title: Elliot's Sin Button)
by Mr. Dolby
(no relation to the famous ones)

Later that night after Elliot went to bed, he woke up and had to go to
the bathroom. On the way back, he noticed light coming from the doorway
of his 16-year-old brother Jesse's room at the end of their second floor
hallway. It was midnight and their parents were sound asleep. Elliot
knew that Mom and Dad would be upset with the high-schooler for not
being asleep too, but the boy learned long ago to keep his mouth shut
when his brother stayed up late. Fortunately, with the boys' bedrooms
being on the second floor and on the other end of the house, their
parents seldom noticed.

Tonight was different. Usually Jesse's door was closed. With it open
the young boy could faintly hear the bed creaking, along with mumbling
he couldn't understand. Was Jesse expelling sin again? Would he be able
to see?? He had to find out.

Elliot walked softly down the hall and looked into the partially-open
doorway. The teen was laying back on his bed with his legs up, pushing
something that the younger boy couldn't quite make out in and out of
his bottom hole.

The second-grader was so excited that he ran straight into the room,
jumping onto his startled brother's bed without giving him time to move.

"Elliot! What the fuck!? Again!?!?"

"I'm sorry Jesse! I just wanted to tell you I figured out what you're
doing!"

Jesse was in shock and naked, with a dildo still stuck in his ass
mid-plunge. "What that... Really? You know?? You'd better not tell Mom
or Dad!"

Their parents were devout Catholics and the sex toy would land him in
big trouble. Ever the rebel, the teen had came out to them as gay last
year. Instead of warmly embracing him, however, they tried to `cure'
him by sending him to a month-long summer `conversion camp'.

Fortunately for Jesse, the boys in his cabin were as rebellious as he
was. While his days were spent with counselors trying to fill his mind
with crap, his nights were spent with his cabin mates filling his ass
with cum after he volunteered to be the cabin cum dump. In the end the
teen was happy he'd been sent, having had more sex in one month at
camp than he had in the last six months at home.

When he returned and his parents realized the camp had failed to change
him, they went silent on the matter, but only after making it clear they
didn't agree with his "choice". They also let him know they didn't
want
Jesse telling his little brother about him being gay until the boy was
old enough to ask about it himself. Unhappy but knowing it was the best
compromise he could get, the teenager agreed to their demand, then gave
them the middle finger and stormed off to his room.

"No, silly! What you're doing is just between you and God. It's
private." replied Elliot as he looked at his brother.

Jesse was now confused, but getting slightly more relieved. "Well....
You're right, it is private. Go close the door, dude. I'm naked."

Elliot ran over and closed the door, then ran back and jumped on the bed
again.

"So why did you barge in here?", asked Jesse.

"To tell you I figured out what you were doing when I barged into your
room last month. Mommy took me to church and the priest helped explain
it to me."

Jesse was getting a little worried again. Was Elliot getting touched?

"What were you and the priest doing??"

"We were in the confectional together and he was explaining about sin."

"Elliot, that's 'confessional' not 'confectional'. But I don't
understand what that has to do with what you saw last month?"

A hyper Elliot started talking a mile a minute. "He told me I needed to
spell sin from my body and to hold the cross next to me and it would
help me get all warm inside. He left and I didn't know what to do, then
I remembered when I barged into your room and you were yelling "Jesus
Christ!" over and over and you were pushing something in and out of your
bottom. I realized you must be using a cross to spell sin! So I took the
cross and shoved it up my bottom and I found a spot that made me feel
all funny and warm inside and I knew I was right!"

Jesse was even more shocked, but a little less worried. "Ummm... bro..
That's 'expel', not 'spell', and I don't have a cross. That isn't what I
was putting up my bottom, see?"

Jesse took a long and very thick, but soft and flexible, dildo out of
his ass and showed it to his wide-eyed younger brother.

Now Elliot was the one who was confused. He was SURE that Jesse must
have been spelling (err.. 'expelling') his sin with a cross.

"But I've never seen one of those at church. How does that help you
expel sin?"

Jesse's shock was wearing off as it became clear to him that his
nocturnal activities weren't going to be revealed, and his little
brother wasn't in danger, just seriously confused. However, all this
talk of Elliot putting a cross up his ass and apparently having a dry
cum as a result of it was causing his horniness to return full force.

He could have corrected his brother and put a stop to what he was doing,
but he had always fantasized about having a younger boy to teach about
butt sex and get naked with. Here was one who slept 50 feet from him and
was literally asking for it! Not to mention it would give him an
opportunity to privately throw the middle finger to his parents again.
He could introduce his little brother to the pleasures of anal sex
without admitting he was gay, or even using the word.

The horny teen decided to throw caution to the wind and follow his cock,
electing to use the misunderstanding to his advantage and encourage
Elliot instead.

"Well... if I tell you, do you promise to keep this a secret just
between the two of us?" Jesse asked his little brother.

"Of course, it's like praying. You're not supposed to tell other people
what you pray for, right?"

"Right. So just between us. Pinky swear?"

Elliot held out his hand and he and Jesse performed the most solemnest
pinky swear oath that can never be broken, ever.

"Well, it doesn't really matter what you use, the important thing is to
find that spot inside you where the sin builds up, and then keep poking
at it until the sin gives up and runs away. Once that happens, you get
that funny warm feeling inside like you had this morning."

Elliot sat there looking at his big brother, still confused. "So I can
poke at it with anything? Not just a cross?"

"Sure. I like to use this. It's called a dildo and this one is nice and
soft. That cross was metal. It must have hurt going in, right?"

Elliot thought back to this morning. "How did you know? Yeah, it did. I
had to press really hard, and it hurt a lot when it went through my
bottom hole. I was afraid I was doing it wrong until I started getting
those warm funny feelings."

The experienced teen felt sorry for the naive boy. He could only imagine
how much that metal crucifix must have hurt going in his brother's
virgin ass.

"The first time hurts no matter what you use. Before today you'd never
let the sin out, so there was a lot of it built up inside you and it
made your bottom hole put up a real fight. You were strong enough to
break through, though. I'm proud of you! Most boys don't do that until
they're a lot older."

Jesse's words comforted his little brother. "Thanks Jesse. So it won't
hurt as much next time?"

"Nah, but you've gotta practice at it. It's like dribbling a soccer ball
down a field. It's tough at first, but the more you do it, the easier it
gets and the more fun it is."

"How often do you practice?"

"Big boys like me practice at least once a day, sometimes more."

"Can you show me how you do it?"

"Ummm... Yeah, sure, if you wanna see." said Jesse, who was seeing his
plan start to work.

Jesse lie back, took the dildo in his hand, and added more lube to
replace what dried out while they were talking. After inserting it again
he started getting into it, sliding it in and out of his ass for several
minutes while his little brother watched, rapt with interest.

"Wow... that's soooo cool."

Jesse started moaning "Oh God.... Oh.... Ohhhh.. Jesus Christ... Ohh...
Ahhhh... Fuck... Oh God...."

Elliot thought to himself "I knew it! I knew I was right!"

Jesse's cock started spewing precum as the dildo hit his joy button.

Elliot noticed the precum and questioned "What's that clear stuff? Is
that sin starting to come out?"

His brother stopped pumping the toy long enough to answer the boy's
question.

"Kind of. It's called precum. I guess that's because it drips out before
the sin 'comes' out.", Jesse explained after thinking quick for an
answer.

"Cool!"

Jesse wiped some up on his finger and then put it into his mouth. "It
tastes good too."

Elliot, again confused, asked "Really? If it's sin, why do you want to
eat it? Isn't that bad?"

Continuing to make up stuff on the fly, the teen replied "No, the angels
clean it before it leaves your body so that the sin doesn't escape into
the world. Try some."

Elliot thought about it. 'If Jesse does it, then it must be ok.' He took
his finger and swiped some off of Jesse's belly, then slurped it up.

"Neat. Kinda salty, but not bad."

Jesse, who was getting hornier by the minute, watched Elliot as he ate
up more of the precum. While watching the second-grader's hand he
observed the dildo in the background. That gave him a wonderfully nasty
idea.

"Elliot, why don't you take your clothes off? I want you to help me."

Elliot wanted nothing more than to help his big brother and to learn
from him, so he stood up on the bed and shucked off his sleeping shorts
in record time.

The now naked boy asked "What next?"

"Remember when I said you could use anything?"

"Yeah...?"

"I want you to try and use your fingers on my sin button. That way you
can feel what it is you're poking at when you're expelling your own sin."

"Really??? You'd let me do that? Cool!!!!"

"Your fingernails are clipped, right? That's important." asked Jesse,
who knew from personal experience that long fingernails and ass play
were a bad combination.

"Yes, Mommy makes me clip them so I don't get dirt under there when I
play in the sandbox."

"Good. Hold your right hand out for me."

Elliot held his hand out and Jesse used his lube to slick up the younger
boy's hand and wrist.

"Now lie down on the bed on your back. I'll get on my hands and knees so
my bottom is in front of you."

"Ok, but why do you want me like that?"

"That way we can help each other. I'll poke your sin button while you
poke mine. Sometimes it feels even better when someone else does it for
you."

"Oh wow. Thanks big brother! You're so cool."

Elliot made his way into position with his eyes looking right at Jesse's
bare ass. The first thing he saw was the still-embedded dildo. The next
thing he saw confused him.

"Jesse, why is there writing on your butt? Did one of your friends
pull a prank on you when you were asleep?"

Shit! Jesse hadn't thought about Elliot seeing his tattoos. They were
the result of a wild weekend at his college friend Caleb's gay
frathouse where the teen had been the guest of honor at a beer and
drug-fueled orgy. He had proven himself to be such a hungry bottom that
afterwards his hosts took him out to a local tattoo parlor and
commemorated the event.

When asked what to draw, Caleb spoke up and said "He wants `Wreck My
Boypussy' on his left butt cheek, and `Bareback Only' on the
right. That's what he kept telling his tops while he was lying back in
the sling Friday and Saturday nights. Oh, and add a `male/male'
symbol below it for good measure."

The artist looked over to Jesse, who just gave a goofy grin and quickly
nodded his head up and down. The man, a former member of the frat until
dropping out in favor of taking up tattooing, gave a knowing smile and
went to work. He knew better than to ask any questions about the boy's
age, or what his current mental state was.

When the (by then sober) 16-year-old got home and looked back at his
butt in the mirror, he was more than a little nervous. Fuck... this was
permanent. Then he thought back to his homophobic parents and how they
had tried to make him `pray the gay away'.

After a few minutes his worries turned into laughter, having decided
this would be another way to flip them the bird, even if they never saw
it. Besides, it would remove any questions that his top might have about
what he was into whenever he got lucky. Jesse decided he liked it. After
standing there looking in the mirror a little longer, he decided that,
no, like wasn't the right word after all... he loved it! He would have
to thank his friend next time they talked.

Back to the present though, the immediate question was how to explain
this to young Elliot...

"Ummm... Well... kind of. Sometimes my friend Caleb and I play horsey
when we have sleepovers. Last time I tried to throw a rug over him as a
pretend saddle and he said it felt too rough and didn't like it. While
I was asleep he wrote `Bareback Only' on me as a reminder never to
use saddles when we play.

The other one is about Harold our cat. He came in and jumped on us while
we were playing video games and made me die right before I reached the
end of the game . I got mad and threw him out the door. Caleb wrote
`Wreck My Boypussy" on me because I almost killed Harold. He messed
up and wrote them both in permanent marker, so they may never come off.
Promise you won't tell Mom or Dad. They'd be mad as hell at me."

All of this seemed perfectly logical to seven-year old Elliot, and the
last thing he wanted to do was to get his big brother in trouble,
especially since he was being so nice tonight. "Ok Jesse. I won't
say anything. Your secret is safe with me!"

Relieved at the close call, Jesse went back to instructing the boy. "Ok,
now pull the dildo out of my bottom. Then fold your hand and thumb like
this, and slowly put the tips of your fingers into the hole."

Elliot did as he was told, removed the dildo, then matched the thumb-in
folded hand position that Luke showed him. He slowly pushed the end of
his hand into Luke's slick and well-prepared ass.

Jesse couldn't believe that 20 minutes ago he was jerking off alone
while using his favorite dildo, and now he had his little brother's hand
on its way up his ass, with Elliot's ass spread wide in front of his
face. Once he had noticed that the boy's hand wasn't much larger around
than the dildo he was using, his cock took over his brain and he knew
what he had to have. Before that day he didn't have much use for the
church, but at that moment he was thanking his lucky stars that his Mom
had taken Elliot to confession.

"That's it. Now move your hand around like you do when you're trying to
dig a hole in your sandbox, and push in at the same time. Just don't
move it too fast, and stop just before you get to your knuckles."

Elliot did as he was told and looked up fascinated as Jesse's asshole
opened up in front of his eyes while he drilled in his hand.

While Elliot opened up the teen's ass even further than it was earlier,
Jesse started to probe the boy's relatively tight hole. He applied lube
to his fingers and started working a forefinger in, rotating it around
and going slowly.

"Oh! You're poking me back there!"

"Tell me if it hurts and I'll slow down."

"No, your finger is lots smaller than that cross was. I'm ok."

Even before Elliot said that, Jesse had noticed that his little
brother's ass was opening up a lot easier than he expected it to. The
cross must have gotten him primed, so he kept going deeper with his
forefinger, then replaced it with his larger middle finger.

"Ooooooohhhhh That feels good. Are you touching my sin button yet?"

"I'm just barely rubbing it little bro. I'll rub it harder, but first
let's have you practice on me."

"Ok. What do I do?"

"Use your fingers and feel around for a bump that feels like a big
smooth marble. It's right behind my pee-pee."

Elliot moved his fingers around, but at his age they weren't quite long
enough to reach Jesse's prostate.

Elliot frowned. "I'm trying big brother, but I don't feel anything."

Jesse had been planning this ever since he got Elliot naked. The horny
teen had always been fascinated with his butt, and had been putting
things up it long before he started jerking off. Back then it wasn't a
sexual thing, but once he discovered how to play with his cock, his
back-door explorations changed from simple boyish curiosity to a
dedicated passion. Once his friend and former babysitter Caleb was old
enough to buy them for him, he started using actual dildos to practice,
rather than the veggies and other household objects he was forced to use
before.

The weekend of the orgy, Jesse had been presented with his latest toy,
the large dildo that he was using tonight. It was a gift from Caleb, who
was tired of hearing his friend bitch that his ass had stretched enough
he'd outgrown his then-current one. The frat boy had ulterior motives
though, knowing it was also a way to help keep the teen's ass
stretched to the same level it had grown to after taking a weekend's
worth of college cocks, and allow it to be wrecked even further at the
next orgy he attended.

That weekend was also the first time that the high schooler witnessed
fisting close-up. He had become fascinated with videos of it over the
previous year, but never knew anyone that actually did it. He heard that
one of the older, more experienced bottoms at the orgy was taking fists,
so while on break from sling duty he went over to watch.

The bottom was empty at that moment, and when he saw Jesse's
relatively smaller hands, asked if he wanted to try. Being an almost
exclusive bottom himself, the boy wasn't too sure, but at that point
was horny enough to try almost anything. After being lubed up and his
nails checked, his education on how to be a fisting top began. Ten
minutes later he was forearm deep into his first ass and marveling at
the feelings.

As cool as that was, taking a fist as a bottom was Jesse's true goal.
He had been sure it would be years before getting a chance to experience
it though, since most adult hands were still far too large to fit inside
his only moderately-stretched teen hole. If all went right tonight,
Jesse would feel his little brother's fist in his ass and maybe even
light a fire of interest in Elliot's head for it too. He was just glad
that he had taken time to give himself a proper deep clean-out in
preparation for his long dildo. That was going to come in handy.

"You're going to have to get your hand in further. Turn your hand left
and right like you're opening a door knob, and push it. Keep trying
until you're past your knuckles. Just go slow and don't push too hard."

Elliot did as he was told, and after four or five attempts, the ring
expanded enough that his knuckles moved forward and his hand was sucked
in. Jesse's ass ring was clamped around the second-grader's wrist. The
boy looked up in amazement as his entire hand was now inside his big
brother's bottom.

"Wowsie! I never thought my whole hand would fit up your bottom Jesse!"

Jesse couldn't believe it either. The most he had had up his hole so far
was the dildo he had been playing with, or four of his own fingers.
Having his little brother's entire hand was up there to the wrist was
one of his hottest fantasies, and it had now come true!

He exclaimed "Oh my God!!... Yes!... Ohhhhhh... Umm.. ok, feel around
and see if you can find my sin button now."

Elliot felt around and found Jesse's prostate.

"I found it! I found it! Right where you said it would be."

Jesse wasn't satisfied and wanted more. He wanted Elliot's hand in
at least as far as his toy. "Grab that lube bottle and put some more of
it on your forearm. Spread the lube on halfway up to your elbow."

Elliot did as he was told. It felt like the slime that he liked to play
with, so he went even farther than Jesse told him to and applied it all
the way to his elbow.

"Ok, what's next?"

"Make a fist with your hand and then push your arm in and out of my
bottom. Use your fist to rub against my sin button as it goes by. That
will make it really aggravated and make every bit of that nasty sin come
out."

Elliot, who loved his brother and wanted to do everything he could to
make sure he didn't go to h-e-double-hockeysticks made up his mind that
he was going to do a super-duper job of pounding that sin out. He
started fisting Jesse, who returned the favor by pushing his middle
finger in and out of Elliot's ass and rubbing harder on his immature
prostate.

"Ohhhhh.... OOOOOOHHHHHH Oh God..... Ohhhh... Fuck... Damn.... Jesus....
Yeah, keep doing that Elliot! Oh my God yes!"

"I'm hitting a wall a little way up. What should I do?"

Jesse knew that wall well, having hit it repeatedly with his newest
dildo. He also knew from that and his brief experience as a fisting top
that it could be gotten past.

"Ohhhhh... Uhhhh... Yeah, there's a bend there. You can get past it but
it's a lot easier if we switch positions. Let's both roll over on
our sides and and I'm going to put my knee and right leg up on top of
you."

Jesse wasn't quite sure why, but doing that seemed to line his insides
up so that he could slide his toy up past that wall easier. He figured
it should work for his little brother's hand as well. Elliot carefully
removed his hand and the two brothers adjusted themselves to the new
position.

"Ok, rub some more lube on my bottom hole and put your hand back in
just like before" said the teen once he was ready.

The newly-experienced little brother did as he was told, squeezing out
more lube and putting it on the opening. He then folded his hand just
like before, and worked it inside the welcoming ass.

"Wow, it went in a lot easier this time!"

"Yeah, your hand stretched my bottom hole earlier, and it won't
tighten back up for a while. Now move your hand up to where you hit that
wall."

Elliot worked his hand and forearm up into his older brother's hole,
resulting in appreciative moans from the bottom boy. "Found it!"

"Ok, stop and fold your fingers up like you did before. Feel around
for an opening. You may have to turn your hand left or right"

"Uhhhhh.... Ok. I think I feel it?"

"Rub on it and push in slow. Don't force it.", instructed Jesse.

Elliot did as he was told and started pressing his extended fingers into
where the colon made a sharp bend. Jesse concentrated on relaxing, and
after a few attempts, Elliot's hand went past the obstruction.

Elliot exclaimed excitedly "I did it! I did it ! I'm through!"

"Ok, now go slow but start pushing in further."

Elliot once again did as he was told and watched in even more
fascination as not only his hand, but eventually his entire forearm
worked its way into his brother's bottom. As he pushed it in, he looked
up in wonder and saw the outline of his hand making a moving bulge in
Jesse's tight muscled belly.

"Wooowwww..... That's so cooooolllll!!"

Jesse was beside himself with horniness and it wasn't going to take him
much longer before he would have to cum.

After a while the teen felt the boy's hand stop moving.

"Ohhhhh..... That feels great bro! How far are did you get in?"

"All the way to my elbow!" Elliot proudly announced.

Jesse started to freak out a bit at this revelation. He knew he was
going to get a fist, an he wanted to get at least half of Elliot's arm,
but he never dreamed that he'd have the boy's arm in his ass all the way
up to the elbow!

Jesse knew that for both of their sakes he needed to remain calm and
instruct his little brother on what to do. He'd seen photos of men and
twinks taking a full-size arm all the way to the pit and was sure they
didn't die afterwards, but from his reading he also knew he had to make
sure Elliot was careful while in so deep.

"That's great little bro. You can't go as fast when you're in that far,
but keep moving in and out. Your arm is rubbing across my sin button and
it's not going to be long before those little buggers start running away
screaming. I'm going to do yours while you do mine."

Elliot started slowly moving his arm in and out with long strokes. As he
was doing that, his big brother was hungrily studying the boy's
normally-hidden boy parts while rubbing his finger hard on his little
joy button. Within a few minutes, Elliot felt the same warm fuzzy
feeling building in his own bottom that he did this morning when he was
poking himself with the cross.

"Uhhh... Ohhhh.... Oh my! Oh! I think I feel it! You're right, it's just
like this morning!"

Elliot's spasms resulted in his arm twitching and jerking inside of
Jesse. Between that and the sexual overload of the last thirty minutes,
the teen couldn't hold out any longer.

"Ohhhh.. Oh shit... Ahhhhhh Fuck! Oh God... Jesus.... Oh Yes! The sin is
going to come out!"

Jesse came with an intensity he hadn't felt since he first started
playing with himself. His jizz shot out and covered Elliot's neck and
chest. Elliot was almost oblivious to this though, since right before
the big cock pointed at him erupted, Elliot started trembling with his
own dry cum, which was even more forceful than this morning. He was so
in shock from the intensity of his tingles that he barely noticed being
drenched with his brother's cum.

Jesse was the first to speak. "Ummmm I think the sin is all gone now.
You'd better take your hand out of my bottom. Just go slow please."

Elliot, still a little stunned by all that had happened, slowly withdrew
his arm from his brother's ass. As he got to the wrist he had to rotate
it around a bit in order for the ring to once again expand to that
diameter, but it popped out without too much effort. The two boys rolled
over on their backs, exhausted.

Elliot looked down at all of the cum on his chest and asked "What's all
this white stuff? Is that your sin? Why is it white and why didn't I
have any?"

"It's called 'cum' and it's what comes out of big boys when they rub on
their sin button long enough. You'll make it too by the time you get to
be my age. It's clean like the precum. There's no sin in it anymore."

"Can I eat it like the precum?"

"Yeah, it's full of protein. Makes you big and strong!"

Elliot wanted to be big and strong like his big brother, so he swiped up
a finger full and put it in his mouth.

"It's kinda weird tasting... I liked the precum better. If it makes me
big and strong I'll eat it though. Mommy's happy when I eat my broccoli,
even though it doesn't taste as good as corn. Is it like that?

"Something like that. You know I'll never make you do anything you don't
want to bro, but yeah, it would make me super happy if you ate it all
up."

That was all Elliot needed to hear, and before long all of Jesse's cum
was in the second-grader's tummy and the boy was licking his lips.

The boy lay back for a moment thinking about what what he had learned
about his sin button, and how good it felt when his brother kept rubbing
it. He was glad that he woke up to go to the bathroom earlier, otherwise
he would have missed out on all of this. Elliot made a decision right
there, and crawled up so that he was laying on the bed face to face with
his new hero.

"That dildo thing you had in your bottom. It felt soft, but it's really,
really big. It's a lot bigger than your finger or that cross. Do you
have one that's my size? And can you teach me how to make my bottom hole
bigger like yours? You looked like you were really having fun when my
arm was rubbing on your sin button. I wanna have fun like that
someday."

The horny teen couldn't help starting to get hard again. This was
turning out even better than his horniest jerkoff fantasies. Not only
had the 7-year-old eaten everything that came out of Jesse's cock and
had half of his arm up Jesse's ass, the boy was now asking his mentor
for his own dildo to use, and instruction on how to open his hole wider.
The teenager's hard cock led the way, making the decision to take full
advantage of his little brother's interest and go for broke.

"Yeah, it was really fun! I guess since you did such a good job tonight,
maaaybe I could teach ya. Just don't tell anyone else what we're
doing. Only big boys are supposed to know how to do that and we could
both get into real trouble if anyone found out I was letting you in on
our secrets. But... if you're a good boy and really want me to, I'll
break the rules and let you in on it early."

Elliot's eyes lit up, and he moved closer to his brother, grabbing
Jesse's hand and looking into his eyes. "I won't tell, I promise!
I'll do anything you say! Just let me be a big boy, ok? Please?
Please??" Elliot pleaded, beside himself with anticipation at being
included in his big brother's secrets.

Jesse's cock started dripping at the sights and sounds in front of
him. His 7-year-old brother was literally begging to be given a dildo
and taught how to gape his own ass. Jesse couldn't believe his luck,
and was more than willing to assist.

"Well... ok, I guess..." said Jesse, feigning reluctance.

"Yay! Thanks Jesse. I promise I'll be the bestest student ever! So
can I have my own dildo to play with now? Please?"

"Not quite yet. Right now, you're just starting and you need one
that's kid-sized. Probably not much bigger than my finger. I wish I
had one to give ya, but I don't. My friend Caleb knows where to get
them. He got this one for me, but he won't be back from college until
December. I'll ask him to get one your size as a Christmas present. Who
knows? Maybe by Christmas time you'll have already practiced enough
with other stuff that I'll have to tell Caleb to go up a size! Until
then, you can use other things."

Jesse knew from the late night talks they had when the two were laying
around stoned at the frat house that Caleb would be more than willing to
get a junior-sized dildo for Elliot, once he found out the boy wanted
one. Caleb couldn't get enough of Jesse's hole five years ago when
he babysat for the then-11-year-old, and the teen was sure that a naked
and willing 7-year-old would make Caleb's mouth water.

Jesse continued "I started out using my fingers. You know what they
say in Sunday School: "Everything was put on this world for a purpose".
Some things have more than one purpose. Your fingers can do a lot of
things, including playing with your sin button. You can also use carrots
and other veggies. Just don't put them back in the refrigerator
afterwards or Mom might notice they're a little smelly and you'll get in
trouble. Really, you can use almost anything, just make sure it's
smooth. Nothing sharp or rough or you'll be screaming the next time you
poop."

"Whatever you use, make sure to get it all slick first with lube. I'll
give you some. I can't give you my bottle because Mom will go
ballistic if she finds it in your room, but I saw an empty lotion bottle
in the trash tonight. I'll rinse it out and put some of my lube in
there for you. You can keep it by your bed and Mom will never know the
difference. Just let me know when you run out and I'll refill it for
you."

"You'll give me my own lube too? Cool! Thanks, Jesse!" Before
tonight his big brother hardly ever talked to him. Now he was being
really nice and teaching him all sorts of big boy stuff. Elliot was
beside himself.

"Someday you can play with a dildo like mine, but first you have to
stretch your bottom hole so it will fit, and that's gonna take a
while. It's like when I lift weights to build up my muscles. I had to
practice really hard and really long to get there, and it helped me to
set goals and take it in steps. At first, lifting 50 pounds was hard for
me, but I made it and then set a goal for 75 pounds, then 100, and now I
can lift over 200 pounds easy. It was hard, but the result was worth it."

"Your bottom hole is a muscle too, and you can work it out like I worked
out my arm muscles. Instead of strengthening it to lift heavier weights,
you'll be stretching it to take bigger and bigger toys. That's how I
worked up to be able to fit this one inside me. I started out small and
tight just like you, but it only took me a couple of years of practice
to get to where I am now, and it was really fun doing it."

Elliot broke in "So, like my doll toy where there's big ones and
little ones and they all fit inside each other? I start with the
littlest one first, then the next one, and the next one, and like
that?", trying to compare his set of Russian nesting doll toys with
the increasing sizes of dildos that Jesse was describing.

"Yeah, that's the idea! Start with something small, then once that
goes in easy, try something a little bigger. Every time you get to where
you can fit something bigger in there you'll feel a sense of
accomplishment, just like when you learned how to tie your shoelaces, or
ride your bicycle without training wheels. Someday, if you work at it
long enough, you'll be able to fit a dildo like mine inside you - and
it's actually kind of small compared to what some of the big boys like
to play with."

Elliot reached over and hugged Jesse. "Thanks, big brother! Tonight
was fun. Can we play with our sin buttons and spell.... err expel more
sin again tomorrow night? Please??"

"Maybe, but if I'm going to be your teacher, you have to do some
homework for me first. Tomorrow, look through your toys and see if you
can find a few that you think are the right size for your bottom. Clean
them up really good in the afternoon, and after Mom and Dad are asleep
you can bring them here and I'll help you try them out. Can you do
that? Make sure you poop first too. It's no fun if your bottom hole
isn't clean. Later on I can show you how to get clean if it doesn't
all want to come out by itself."

"I will, Jesse! I'll find something tomorrow and bring it to play
with. Thanks big brother!"

"Ok, now go back to bed and get some sleep. Just make sure you wash
your arm first. You have to wash up really good every time you play with
your bottom. We don't want Mom to start calling you Smelly Ellie!"
With that, the boy grinned, hugged Jesse again, then jumped up and
exited the room.

Once Elliot had cleaned up and was back in his bed, he lay there
thinking, his mind going over everything his big brother said, and began
planning out his practice sessions. He thought about the contents of his
toy chest and started making a mental list of what was smooth and looked
the right size to fit up his bottom. He knew he'd be going back to
Jesse's room whenever he could for more advice and for more mutual
sin-expelling sessions, but he now had a plan. His priest would be
proud! He probably wouldn't tell him though, since this was all private
stuff between him and his brother and he didn't want to get his
brother in trouble. After all, he had pinky-sweared to keep it secret,
and you never-ever break a pinky swear!

At the same time in the other room, Jesse lie back alone in bed as he
too went over the evening's events in his mind. In a one hour session he
had went from jerking off alone with his dildo to introducing his little
brother to butt sex and fisting, not to mention being fisted for the
first time himself! More importantly, his daydreams of having a boy to
mold and shape in the ways of sex had went from being one of many
fantasies to being a reality. In the back of his mind he knew he would
eventually have to 'fess up to the boy about his prostate not really
being a 'sin button', but figured by the time Elliot got to that point
he would be too hooked on jerking off and playing with his butt to be
mad at him.

The teenager once again reached for his bottle of lube and slicked up
both his cock and his dildo. After that pillow talk with Elliot, there
was no way he was going to be able to get to sleep without another cum.
What would the future hold now that he had a budding sex demon for a
little brother? Only time would tell. Jesse's fist started to work his
cock while his other hand worked his dildo and his mind raced, thinking
of all the horny possibilities that lie ahead for them.

The End
(or... is it just the beginning??)


Author's note:

I've read stories on Nifty since the site's inception, but this is only
my second story as an author.  Thanks in advance for those who take the
time to email back with positive comments and constructive criticism.
I spent decades not emailing authors, but starting in 2021 have tried to
be better about that, and now understand how important it is to authors
for readers to do so.

My other story:
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https://www.nifty.org/nifty/gay/incest/brothers-behind-closed-doors

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