Date: Sat, 27 Feb 2021 21:20:00 -0700
From: Jordan Bradders <jordan.bradders@writeme.com>
Subject: My Favorite Babysitter - Part Five - Tim and Bobby

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This work of fiction involves sexual contact between four boys, a
16-year-old babysitter and his 12-year-old charge, and their 14- and
12-year-old friends.  None of these people is or ever was real.  THAT IS,
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===================================================

My Favorite Babysitter - Part Five - Tim and Bobby

By Jordan Bradders

   (c)Copyright 2021 Jordan Bradders.  The author reserves all
rights. Permission is granted to download this story for personal use
only. It may not be published in any other forum, web site, blog, magazine,
newspaper, granite block, parchment scroll, golden tablet, book or other
medium without the author's prior permission.

    Summary: 16-year-old Brian was hired to babysit Casey over the weekend
of his 11th birthday. Casey is small for his age, smart, and cute.  Brian
seduces him; it is not hard because Casey wants it. Brian and Casey's
relationship is well established after only about 24 hours.  The younger
boy trusts his big friend and wants to please him.  Brian convinces Casey
to penetrate him with a strap-on dildo, resulting in enough bleeding to
terrify the younger boy and convince him to never do it again. Brian, on
the other hand, is thrilled and wants more.  They go skinny dipping in the
woods.  They are caught by a couple of boys, who steal their clothes.  They
are forced to walk through the woods naked, but when the other boys, who
are also gay, discover the nature of their relationship, they apologize and
return their clothes. They reach a truce with Bobby (14) and Tim (12), then
return home, completing their first weekend together. Brian briefly
encounters Bobby on the school bus, but does not acknowledge him, while
Casey meets and forms a friendship with Tim, who is one year ahead of him
in Middle School. Casey's mother, Barbara, who has been promoted to a job
that involves significant travel, offers Brian a job as Casey's "mentor"
and regular babysitter. Part Four ends with Casey accepting an invitation
for him and Brian to meet Tim and Bobby in the woods on Saturday.

This, the fifth installment in a multi-part story, will make more sense if
you read parts one, two, three and four, which are available on Nifty,
under Gay Male Stories in the Young Friends category:

Part One:
http://www.nifty.org/nifty/gay/young-friends/my-favorite-babysitter/my-favorite-babysitter-1

Part Two:
http://www.nifty.org/nifty/gay/young-friends/my-favorite-babysitter/my-favorite-babysitter-2

Part Three:
https://www.nifty.org/nifty/gay/young-friends/my-favorite-babysitter/my-favorite-babysitter-3

Part Four:
https://www.nifty.org/nifty/gay/young-friends/my-favorite-babysitter/my-favorite-babysitter-4


Chapter Thirty-Three

Tim lay in his bed, awaiting sleep.  He could not forget the two boys he
and Bobby had met in the woods that day.  His hand went to his crotch as he
thought about what he and Bobby had seen them do together.  Of course, he
had known there were other gay boys out there, but he couldn't imagine how
to go about finding them.  He shook his head as he thought back to how he
and Bobby had met.  It had happened at the community pool the previous
summer.

Tim had stepped out of the locker area, dressed only in a tiny pair of
Speedo-style swim trunks. He pretended to be embarrassed by the skimpy
suit, the last vestige of his single season on the community swim club's
age-group team, but he secretly loved the looks he got from some of the
older girls. His head high, he quickly made his way to the three-meter
platform. It had looked so high when he had first seen it at age eight.  He
looked down as if surveying his domain, then performed a forward arm stand
with a somersault; as always, he slipped into the water with almost no
splash.  A self-described "water rat," he had learned that dive watching
YouTube videos of the Summer Olympics. and practicing the moves in his
bedroom. The dive had turned out to be simple, though he failed the first
dozen or so tries, until he realized that the platform just was not high
enough for two full somersaults.  Once he dropped it to one, the dive had
fallen into place.  It had become his signature move on arrival at the
pool, and he sometimes waited on the edges until he had a small audience
for his entry.

He had surfaced and knifed through the water, still showing off, though he
was unsure for exactly whom. He enjoyed the attention from the girls but
felt no attraction to them.  He had known he was different for some time.
He had told himself that he'd watched the male divers and gymnasts instead
of the women because he'd wanted to emulate them, but that wasn't the whole
story.  He had felt a stirring in his gut at the sight of some of those
young men.  Though he had not fully understood it, he'd known that none of
his friends responded the same way.

Always aware of appearances, he had breasted out of the pool instead of
using the ladder, then used his hands to brush some of the water from his
smooth skin before striding to the lifeguard stand.  Jonah, the guard on
duty, was one of his favorites.  He never seemed to lose patience with the
younger boy, even when he hung around and made a nuisance of himself.
Truth be told, Tim had a crush on the sixteen-year-old, but he had seen
enough girls hanging on him that he was sure nothing was going to come of
it.  He had stood and talked with the older boy for a few minutes as he
scanned the pool, fantasizing that it was he who sat perched atop the
stand.  He had noticed an older boy who seemed to be watching him, but each
time he looked his way, his eyes seemed to dart away.  Finally, he had
grown tired of his lifeguard fantasy, slipped back into the water and
started swimming laps.

He had repeated this performance the next day.  Truth be told, there was
little else to do, so he ended up at the pool nearly every day.  His single
mother worked, and he wasn't allowed to leave the neighborhood.  That left
him with four choices: sleep, play video games, watch TV or go to the
pool. He had noticed the boy he'd dubbed "shaggy" because of his unruly
brown hair watching him from under his bangs, but every time he'd tried to
make eye contact, the other boy had looked away.  Finally, bored, and
lonely, Tim had decided to make his move.

Taking a running start that was guaranteed to raise the ire of the
lifeguard, he jumped out over the shallow end of the pool, tucked his legs
into a cannon ball, and slammed into the water only a few feet from the
other boy.  He had intended to hit him with a huge wave; he hadn't intended
to hit the pool bottom with his back.  A sudden gasp of pain and surprise
drew water into his airway, and he came up sputtering, unable to breath.

The older boy had watched his approach but was still surprised by what
happened.  He had immediately grabbed Tim under the arms and helped him to
his feet, then dragged him toward the side of the pool. Embarrassed, Tim
had leaned on the wall until he'd regained control over his breathing.
Looking up, he saw that the lifeguard was watching -- and laughing -- but
had not moved from his station.  'Nice,' he'd thought.  'It's good I'm not
drowning.'

He had, of course, been mortified.  That was not the entry he'd intended.
But there he was.  Turning toward the other boy, he smiled sheepishly and
said, "Thanks for not lettin' me drown."

The other boy had smiled and swung his head, tossing his brown bangs out of
his eyes.  "It's okay.  I had nothin' better to do."

That had been four months before.  The two boys had become fast friends,
spending at least part of each day together, inviting one another to sleep
over more nights than not.  Each of their single mothers had come to accept
the other boy as a member of the family.  Eventually, horseplay had turned
into wrestling, which had turned into exploration and experimentation.
Each boy had been pleasantly surprised when he learned that the other liked
boys, and specifically liked him.

Chapter Twenty-Six

Tim made a point of looking for his new friend at school on Monday.
Franklin Middle School took pains to protect the innocent "sixlets" from
the big, bad seventh and eighth graders, keeping them on their own floor of
the building, assigning them a separate lunch period, etc., but they could
not prevent all mixing. So it was that Tim spotted Casey in the throng of
students entering the building in the morning.  Smirking as he thought that
he'd seen the younger boy just the day before, he walked up and said,
"Remember me?"

The smaller boy looked up from his apparent study of the floor and grinned.
"Hey, Tim!  Where's Bobby?"

Tim pulled Casey aside.  "He doesn't go here.  He goes to Lincoln.
Remember?"  Looking around as if afraid of being overheard, he added "We
probably shouldn't talk about him or..."  He made a point of not saying the
name of Casey's boyfriend.

"Oh.  Yeah.  Sorry."  Casey smiled ruefully.  "I'm kinda new to this stuff.
Ya know?  I only just met..."  He paused.  "... him last Saturday."

Chapter Twenty-Seven

Tim pulled Casey into the cafeteria and went to get the two of them coffee
and croissants. He'd watched the younger boy the previous morning, so
suspected that he didn't really like the bitter drink, but he really wanted
the two of them to be friends, and this seemed like the only thing they had
in common. 'Well,' he thought, 'except that we both like boys.'

"So," he asked. "How do ya like Franklin?"

Casey grinned. "I guess it's okay." He paused and added "I like it way
better'n elementary school, because we don't have the same teacher all day,
and we get breaks between classes."

Tim nodded. "Yeah...even if one of your teachers is a ball-buster, you only
have to put up with them for one period."

Both boys laughed as if Tim had made a world-class joke.

They sat and sipped coffee and ate their croissants until the first bell
rang, then they got up, tossed their waste into the trash cans and headed
off to class.

This time, it was Tim who stood and watched the younger boy walk up the
stairs, his eyes taking in his entire frame. 'He's really cute,' he
thought, as they went their separate ways.

Chapter Twenty-Eight

Bobby arrived at home and let himself into the house just long enough to
put his backpack in his bedroom. Then he went to the garage, retrieved his
bicycle, and peddled over to Tim's house. Neither his nor Tim's mother ever
got home before 6PM, so this was his normal routine.

He let himself in by the back door, sat down in the kitchen, and picked up
the peanut butter and jelly sandwich his friend had already placed on the
table. After taking a big bite, he smiled and asked, "So how was school
today."

The two boys sat and talked about their days for a few minutes,
occasionally biting into their sandwiches. Then Bobby said, "Guess who I
saw on the school bus yesterday." Not waiting for a response, he said "The
bigger kid we saw in the woods Sunday."

Tim grinned. "Yeah, I ran into Casey, too. He's really nice."  Pausing, for
a moment, he went on "The older kid's Brian. Casey says he's not as scary
as he looks."

They talked for a while, then Tim got up and cleared the table. "You wanna
go upstairs and... ummm...hang out?" He had learned not to be too direct
with Bobby, who was still uncomfortable with the idea of being "gay." The
older boy preferred to think of them as friends who messed around, rather
than as boyfriends. When he thought about it too much it bothered him; so,
he tried not to think about it much.

Bobby got up without a word and started up the stairs, pulling his shirt
over his head as he climbed. By the time Tim got into the room, Bobby had
already kicked off his shoes and was stepping out of his jeans and
underwear.

Tim grinned as he grabbed the older boy's penis and started running his
thumb over its head. "Damn! I love playin' with this thing."

Bobby pulled Tim's shirt over his head, grinning at his exposed
armpits. "Do ya think you'll ever grow any hair?"

Tim stopped, a pained look on his face, and peeled off the rest of his
clothes. "Hey! It's not like you've got a lot of hair!"

Seconds later, they were in bed, each of them licking, kissing, and sucking
the other. Bobby didn't like to lip-kiss, because that was "too gay" for
him, but he was happy enough to do everything else. Soon he was close to
orgasm, so he pushed Tim away. His voice husky, he rasped "Turn over," as
he reached into the bedside table for Vaseline.

Tim was happy to oblige, pulling a pillow down to place under his lower
torso. He waited as Bobby greased his five-inch cock, then did the same for
his anus. His voice impatient, he moaned "Come on, Bobby. Fuck me!"

Soon the older boy was grunting rhythmically as he pumped in and out of his
"best friends" anus. He was already close, so he knew he would not last
long, but he tried to delay his orgasm. He knew Tim really liked being
fucked, so wanted to keep it up as long as he could. Then he flashed to the
10th grader he had seen on the bus, then to his naked form in the woods,
and finally to what he had seen him do with his younger friend. He
exploded, filling Tim with his hot cum.

He collapsed on top of his friend, his half-hard dick still in his ass. He
was confused. 'I'm not queer,' he thought as he considered what had just
happened. He wrapped his arms around the smaller boy and held him close.

Tim lay there and enjoyed the skin-to-skin contact with his older
friend. He did not really enjoy anal, but he liked what always came after,
as Bobby recovered. He loved to cuddle but had decided to take what he
could get. His mind drifted off to his new 6th grade friend. 'I wonder,' he
thought, 'if Casey likes to kiss and cuddle?"

Chapter Twenty-Nine

"I'm bored."

Bobby looked at Tim. "What?"

"I'm bored. This is all we ever do. You come over here. We play video
games. You suck me. I suck you. You fuck my ass. Sometimes we make out,
then you get all weird and tell me you're not gay. Then you go home. What
the fuck are we doing?"

Bobby stared at Tim but said nothing.

Tim stood up, still naked. "What are we. Bobby? I think of you as my
boyfriend, but you keep sayin' you're not gay. Right? So what the fuck am I
to you?"

Bobby was stunned. They had just done all the things Tim had mentioned,
includng making out. They'd even lip-kissed; except for the getting weird
and saying he wasn't gay part. He sighed and said "I really like you,
man. I really do. But I don't know if I'm really gay. I think I like girls,
too, but..." He let the sentence hang and wrung his hands.

"That's the problem, Bobby. I know I'm gay. One hundred percent. I've known
a long time. Girls don't turn me on at all; but you do, Bobby. I love you."
Tears welled in his eyes as he said, "But I think you're just messin'
around with me till you find a girl."

He went into the bathroom, leaving Bobby alone in his room.

Bobby just laid there, lost in his thoughts. He flinched when he heard the
lock click. `What the fuck does he want from me? He's my best friend. I
never told him I loved him or anything like that. What the fuck!"

Tim came back into the room. He had obviously been crying, but he was dry
eyed now. "I really do love you, Bobby. I understand if you don't love me,
if you wanna just be friends, but I can't keep doin' this."

Tim started pulling on his clothes. "If we're just friends, we have to come
up with other stuff to do.  I can't just be your little fuck-toy until you
find a girlfriend. I don't even like bein' ass-fucked. I let you do that
because I thought you loved me, and I really liked cuddling after. But I
know you don't. I guess that's too gay for you." Dressed, he walked out of
the room and went downstairs.

Bobby quickly dressed and followed him to the kitchen, where they sat down
at the table. "Look, Tim. You're right. I don't know if I'm gay; I don't
even know if I'm bi." He looked down at the table, his hands folded in his
lap. "I know I like you a lot, but I don't know if I love you. I'm not even
sure I know what love is."

Tim got up and filled two glasses with ice water. He sat down and slid one
across the table to the boy he now realized might be his best friend but
was not his boyfriend. He smiled ruefully and said, "I hope you can figure
it out; but until you do, maybe you better go home." Looking him n the eye,
he added, "now, Bobby!"

Tim sat and sipped his ice water in silence, his eyes on the untouched
glass and empty seat on the other side of the table.  Slipping his phone
out of his pocket, he pressed the speed dial button for his new friend,
Casey.

==========================================================

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