Pushing Boundaries/Chapter I

Oliver sat slumped in his history class, his mind wandering far from the classroom. The teacher's monotonous voice was nothing more than white noise in the background as Oliver daydreamed about the video games he'd play as soon as he got home. Suddenly, his phone buzzed in his pocket, and he felt a glimmer of excitement at the message from his friend Mark: "Bro, you wanna come over today and play?"
Oliver's face lit up with a smile, but his excitement was short-lived. He realized he couldn't accept the invitation - he had promised Chloe, his younger sister, that he would walk her home from school today. Although their chauffeur usually picked them up, the two siblings often preferred to walk home together, enjoying the fresh air and each other's company.
Oliver quickly replied to Mark's message, explaining the situation: "Sorry, bro. Can't come over today. I promised Chloe I'd walk her home."
Mark replied with a disappointed frown emoji and a complaint about how they rarely hung out outside of school.
Oliver sympathized with his friend but could do nothing to change the situation. "Yeah, sorry. My parents are really strict sometimes. You know how parents are."
This wasn't entirely true, though. The real reason Oliver couldn't hang out with his friend was that his parents were never home. Running a company that required frequent travel, they were only home for three months out of the year. Although they had a full staff to take care of Oliver and Chloe, Oliver still felt a sense of responsibility towards his younger sister. He couldn't break his promise to her, even for a fun afternoon with his friend.
Oliver found himself lost in thought as he walked out of his last class and headed to the front entrance of the school to meet Chloe. He spotted her standing with her best friend, Grace, who was chatting away animatedly.
"Hey, Chloe," he greeted his sister, "Ready to go home?"
Chloe's face lit up at the sight of her brother. "How was class?" she asked.
Oliver turned to Grace and smiled. "Hey Grace!" he said, "How are you doing?"
Grace beamed at him, the light freckles on the bridge of her nose crinkling up. Her brown hair was tied up in cute pigtails that hung just past her shoulders.
Oliver normally didn't care much for Chloe's friends, seeing them as only being friends with her because of her popularity. But Grace was different. She was always friendly towards him and often hung out with his sister outside of school.
Despite his protests with his parents, she frequently visited their house despite his friends not being allowed to. His parents, mostly his mom, were always hesitant to let him invite friends over, fearing that they would cause heaps of chaos and trouble. It wasn't without reason since the last time Oliver was able to invite some friends over, Jasper, a friend of his, fell off a tree he was climbing and broke his arm. Jasper's parents ended up trying to sue them!
It took some time but Oliver didn’t mind when Grace came over now, he appreciated her outgoing personality even if he sometimes felt awkward around her.
"Class was pretty boring today," he replied to Chloe, "but I'm glad the day is over."
Chloe chimed in, "We had a math test today. I think I did pretty well!"
Oliver gave her a proud smile. "That's great, Chloe! I knew you would do well. You've been studying really hard the past couple of days."
After a few more minutes of chatting between the three of them, the siblings said their farewell to Grace. Oliver and Chloe walked into the entrance of their neighborhood and Chloe grabbed his brother's hand. Oliver smiled as his sister held his hand while they continued walking. They walked in silence for a while, enjoying the warmth of the sun and the sound of the chirping birds.
Oliver and Chloe walked in silence for a while longer before Chloe spoke up. "Do you ever wonder what it would be like to have a girlfriend?" she asked, looking up at her older brother.
Oliver shrugged. "I don't know. I mean, it would be nice to have someone to talk to and hang out with, but I'm not really sure I'm ready for all that stuff yet."
Chloe nodded, seeming to understand. "Yeah, I get it. But it's not like you have to get married or anything. It can just be something casual."
Oliver chuckled. "Casual? I don't think dating is ever really casual, Chloe."
Chloe rolled her eyes. "Well, you know what I mean. It doesn't have to be anything serious. Just someone to have fun with."
Oliver thought about it for a moment. He had to admit, the idea of having a girlfriend did sound kind of nice. But he wasn't sure how he would even go about finding one. He wasn't exactly the most popular guy in school, and he didn't have any experience with girls.
"How about you, Chloe?" he asked, curious.
Chloe shook her head. "Nope. I'm not really interested in dating yet. I mean, I have friends who are boys, but I don't really see them that way, you know?"
Oliver nodded, feeling a little relieved. He wasn't sure he was ready for his little sister to start dating yet, either. They walked in silence for a little while longer, lost in their own thoughts.
Suddenly, Chloe spoke up again. "Olly, I think Grace likes you," she said with a teasing tone.
Oliver was taken aback. "What do you mean?" he asked, confused.
"I mean, you know, when a girl likes a boy," Chloe explained while rolling her eyes.
Oliver's face turned beet red at the mention of Grace liking him. He had never considered the possibility before, but now that Chloe had mentioned it, he couldn't help but think about it.
"I don't know, Chloe," Oliver said, trying to play it cool. "She's just being friendly like she always has."
"Come on, Olly," Chloe said, rolling her eyes at her brother. "You're not that dumb. How many girls in your class actually talk to you or your friends?"
Oliver had never really thought about it before. Sure, there were one or two boy and girl dating, but it wasn’t anything serious. Chloe was right now that Oliver thought about it, the boys and girls are usually in their own groups. Its not like he didn’t think Grace was cute, its just that he had never considered that someone like Grace might like him. He had always seen her as just a friend of his sister, nothing more.
"I don't know, Chloe," he said, still feeling a little uncomfortable and wanting to drop the conversation all together. "I mean, I think Grace is just really friendly and you’re reading into it too much. That's all." Chloe gave him a knowing look. "Okay, if you say so."
Oliver was eager to change the subject and without warning, he yelled, "Race you home!"
Chloe grinned mischievously at her brother. "You're on, Olly!" she shouted before taking off down the road.
Oliver immediately regretted his challenge as he watched his sister's backpack bounce up and down as she sprinted ahead. He quickly followed, his own backpack weighing him down as he tried to keep up. Chloe had always been more athletic than him, but he had hoped to at least put up a good fight.
The two siblings weaved in and out of the streets, passing houses and buildings at a dizzying speed. Oliver felt his lungs burning as he tried to catch his breath. Chloe, on the other hand, seemed to be unaffected, her breaths coming out in short puffs as she kept up the pace.
As Oliver and Chloe turned the corner onto their street, they were met with the sight of their sprawling estate. The mansion was surrounded by acres of tall, evergreen trees that acted as a natural barrier to provide privacy to the residents. The siblings had grown up here and knew every inch of the estate like the back of their hands.
The front gate of their home came into view, they were met with the sight of an impressive mansion that could easily be mistaken for a luxurious hotel. The house stood tall with several levels and grand windows. The exterior color was a warm shade of cream and black trimmings, giving it a classic modern look.
As they approach the large entrance gate that surrounded their sprawling home, Oliver saw that Chloe was still a good distance ahead of him. He pushed himself harder, trying to close the gap between them, but it was no use. Chloe was already at the front gate, panting heavily but grinning triumphantly.
"I won!" she shouted, throwing her hands up in the air.
Oliver wasn’t far behind her and it took only a few minutes before he got to the gates too, but collapsed onto the ground and gasping for air. Beads of sweat rolled down his foreheads as his exhausted body recovered from their intense race.
The security guard, stationed in the small air-conditioned room adjacent to the gate, let out an exasperated sigh as he saw the siblings on his monitor and pushed a button on his security console to open the gate for the two siblings. As the gate began to roll open, Oliver and Chloe took a few moments to catch their breath and regain their composure before walking through the gate.
Oliver shrugged and claimed, "Let's just call that one a draw."
Chloe retorted, "No way, I totally beat you!" She preceded to playfully punch him in the right arm.
Oliver decided not to argue any further about the race as he was just too exhausted to care anymore. The summer heat only made him want to take a long shower and have ice cream.
As they pushed open the grand set of double wooden doors, the intricate designs carved into the woodwork caught their eyes. Tall columns flanked each side of the doors, giving the entranceway an air of majesty. They stepped inside, sighing with relief as the cool air from the air conditioning washed over them, and immediately dropped their school bags onto the polished marble floor.
Above the foyer hung a crystal chandelier, casting a warm glow throughout the room. The walls were adorned with intricate paintings, their frames gilded with gold, and tapestries imported from Italy hung in between. It was a foyer that spoke of elegance and class.
As they turned left from the grand foyer, the cool and polished marble floor felt smooth beneath their sock-clad feet. Oliver and Chloe couldn't resist the temptation to slide along the hallway, giggling with delight as they glided across the floor. With each step, they picked up speed, their arms flailing for balance as they made their way towards the kitchen.
The kitchen is a chef's dream, with top-of-the-line appliances and plenty of counter space for food preparation. The cabinets are a rich cherry wood, and the counter tops are made of sleek black granite. A large island sits in the center of the room, offering additional workspace and a place for family and friends to gather while meals are being prepared.
Oliver deftly opened one of the refrigerator doors, grabbing a bottle of water in each hand. He closed the door with his elbow and handed one of the bottles to Chloe before eagerly unscrewing the cap on his own bottle and gulping down the refreshing liquid.
After finishing their water, Chloe suggested they take a shower together. Despite being past the age when most siblings would stop bathing together, Oliver and Chloe had their own reasons for continuing to do so. Oliver was the first to try and break out of this norm at the age of four but Chloe never really did or wanted to. She would protest until he eventually gave in. One time, Chloe went a whole week without bathing until Oliver agreed to bathe with her again. It was a battle he could never win, and he eventually stopped trying before he turned six.
Their parents also tried to deter them when Oliver reached the age of five but since they weren’t home much to being with they simply just ignore this when they were gone. Even the short time they were home, the siblings would end up bathing in secret when their parents weren’t really paying much attention to either of them.
The bathroom closest to their room is quite spacious and well-lit with natural light. It has large polished marble floor and wall tiles, giving it a clean and modern feel. The shower area itself is separated by two clear glass enclosures, with a rainfall shower head mounted to the ceiling. Directly across the shower area was a large bathtub that can comfortably fit two or three people.
Oliver hastily turned on the shower and tried to dodge the cascading cold water while trying to adjust the knobs on the wall to make sure it was the right temperature for them. Meanwhile, Chloe began to undress, she first took off her skirt, her white socks were next and then her dress shirt, which she carelessly tossed onto the floor. She then removed the scrunchie from her ponytail, and her long, silky blonde hair cascaded down her back like a waterfall, stopping just before her hips.
"Is the water hot enough yet?" She asked.
Oliver nodded, "Yeah, almost." He then turned back to look at his sister who was, sitting on the edge of the bath, busy texting away on her phone. She had nothing on but her white panties. Oliver couldn't help himself but glance at her budding chest. He has seen them almost everyday but it was only in the past year has he paid any kind of attention of Chloe’s body.
Chloe caught him looking and gave an innocent smile before she continued to text on her smartphone. "I think they grew a little, what do you think?" she asked.
Like a deer caught in headlights, his face flushed red and he quickly looked away from her small budding breasts, and refocus his attention on the raining water that was starting to steam.
Chloe giggled, "Relax, its not like this is our first time we’ve seen each other naked. Your a boy so its only natural, right? And a girl’s got to wonder sometimes though too on what a boy thinks. Who better to ask than my cute brother?"
"They look the same," he muttered under his breath, feeling the flush of embarrassment spread across his face.
Chloe shrugged and place her phone by the bathroom vanity. She slipped off her cotton white panties, and walk past Oliver and into the shower. The water instantly hit her body and made her hair curl around her head like tiny tendrils of steam. Chloe let out a loud sigh of relief and smiled at her brother while he took off his clothes. He joined her in the large shower where his sister stood under the water humming a tune.
Chloe spun around and wrap her arms around her brother’s neck, sending a warm tingle through his body as her wet skin pressed against his neck. Their eyes met, and neither of them looked away as the hot water rained down on them.
Chloe broke the moment of silence and asked quietly, "Maybe its hard to tell by looking. Go ahead and feel them."
Oliver looked back into his sister’s green eyes, but he broke the gaze while his eyes travel to her small budding breasts. "I don't know..." he replied with an awkward chuckle. He wrap each of his hands around her small mounds while giving a small squeeze before quickly withdrawing them. "Y-yeah... they feel like they've gotten a little bigger, I guess."
Chloe giggle before leaning forward to give his cheek a kiss. "I think your pee pee has also gotten a little bigger too.”
Oliver was so distracted that he didn't realize his dick was fully erect and pressing up against the lips of his little sister's pussy. He quickly turned around with a flush of embarrassment.
Chloe gave him a mischievous grin and wrapped her arms around his chest, feeling him tense up a little bit. She found his discomfort endearing, and couldn't resist teasing him just a little bit more. She wondered how far she could take it, how much she could make him blush and stammer.
She pressed her wet naked body against his back and whispered into his ear, "It’s only fair that I get to touch too, right?"
"What do-” Oliver attempted to ask but was interrupted as his sister glided her right hand down from his wet chest and wrapped it around his cock.
His body stiffened as her soft palm rubbed over the length of his shaft, causing a warm tingle to run through every nerve in his body. He let out a moan as her hand started to move up and down on his shaft. Her touch was warm and soft. He pushed his back against Chloe’s wet body, lavishing the warmth. It wasn't long before he could feel his dick tense up and something was building up inside of his balls as Chloe continued to stroke him off. The pressure built up until finally he couldn't hold back any longer and began to release thick ropes of cum all over the shower wall. The stream of water slowly washed the cum away into the shower drain.
Oliver slummed down and sat on the shower floor. He tried to looked at his sister but his vision was a little blur while his brain and dick recover from his first ever orgasm.
“Did you just pee?!” she curiously asked him. She knelt down next to the shower wall to try get a glimpse at what came out of his brother’s dick but the water had already wash most of the evidence away.
“No!” he shot back.
“Then what was it?”
Oliver looked baffled and replied, "How the heck should I know?" He scratched his head and looked at her suspiciously, "How do you not know but know how to do that."
“A girl’s secret,” she replied while smiling at him. “Come on, we need to get out of the shower or we will be all pruney. Trust me, it's not a cute look," Chloe advised as she got up to turn off the water.
Oliver got up from the floor and walked out of the shower. He walked over to the linen closet to grab two fluffy white towels and tossed one of the towels to Chloe as she exited the shower.
They both started to dry off, Oliver quickly dried himself off and threw his towel into the laundry basket and sat on the edge of the bath, waiting for Chloe to finish. While, Chloe, still dripping wet, struggled to wring out the excess water from her long hair. After a few minutes, she gave up and tossed the sopping towel into the laundry bin. With a sigh, she walked over to the linen closet and pulled out a fresh towel, wrapping it securely around her head to absorb the remaining moisture.
She walked over to the large mirror next to the bathroom vanity. The steam from the shower had fogged up the mirror, but that didn't stop her. With a grin on her face, she wiped the condensation away with her hand.
Oliver sat on the edge of the bathtub with his eyes glued to the bathroom mirror where his Chloe was standing. She was striking a few poses, admiring herself in the reflection. He couldn't help but feel amuse by her behavior, but his thoughts quickly turned to conflict.
As he watched her, his eyes couldn't help but wander over her body, admiring her ass. However, as soon as the thought entered his mind, he quickly averted his gaze, feeling guilty for thinking such things about his own sister.
Their parents had always warned them about the dangers of bathing together, and now it seemed things had escalated even further. He couldn't shake off the feeling of guilt and shame that washed over him, knowing that he shouldn't be feeling this way about his own sister. He tried to push the thoughts out of his mind and focus on something else, but the damage had already been done. The memory of that moment would forever be etched in his mind and the dynamics between the two of them would be changed forever.