The following story is a work of complete and utter fiction. That means that it is not a true story.
It is meant for adults; if you are under 18 or the age of consent where you live, stop reading now and do not download this story.
This work of fiction involves sexual contact between four boys, a 16-year-old babysitter and his 11-year-old charge, and their 14- and 12-year-old friends. None of these people is or ever was real. THAT IS, NO REAL PEOPLE, WITH THE POSSIBLE EXCEPTION OF THE AUTHOR, WERE INVOLVED IN THE MAKING OF THIS STORY.
If you have difficulty distinguishing fantasy from reality, please stop reading now, do not download this story, and consider getting psychiatric help. If you have already consulted a psychiatrist, please take your medications.
If such stories offend you, remember that nobody is making you read this story. Come to think of it, what are you doing on this website? Stop reading now and go to church. If such stories are illegal where you live, stop reading now, do not download this story, and consider moving to a less repressive country.
If you enjoy reading stories like this one, please consider donating so that we can continue to enjoy sharing and reading these stories. Operating sites like this one is not free.
All my stories are also archived on my personal website at http://jordanbradders.com/
I really like SPECIFIC feedback on my writing (i.e., what did you like, what did you not like?). Good or bad, it helps me improve. I also like story ideas, though I cannot guarantee that I will use every suggestion. If all you want is to tell me I am a sick son of a bitch for imagining such a story, don’t bother; I already know that.
Message me here or email me at jordan.bradders@writeme.com
===================================================
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 It may not be published in any other forum, web site, blog, magazine, newspaper, granite block, parchment scroll, golden tablet, book or other medium without the author’s prior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.
==========================================================
If you enjoyed this story, please message me here or email me at jordan.bradders@writeme.com and let me know. Why write more if nobody’s interested. Right?