My Brother's Keeper Ch. 06

"Son of a bitch..." Kaitlyn huffed in frustration, shutting her calculus textbook with enough force to shake her desk. Her body ached; the memory of Jesse's slow, deep thrusts into her the previous day had consumed her every waking moment. While she had not expected to have sex with him on the hard, wooden bench of the player's locker room at half-time, it had been a welcome surprise, only to be topped by Jesse inviting her over the next day. However, now that the day had come, she had yet to hear a word from him.

When they had discussed their tentative plans, there was no time set or further information given to her: only the invitation. Was she supposed to just show up? What if he didn't want to see her and meant for her to come over in the evening? Would his frat brothers all be home, and would word spread about her visit?

Even though she and Jesse had hooked up several times, that fear of being discovered continued to gnaw at the back of her mind. If anyone knew the story, the context, or how it could impact Oliver, they would hate her; and wish harm on them both. But recently, she began to wonder... why should she feel so guilty? Oliver would be hurt, yes, but he would need to understand that it was necessary. He had grown so much since Jesse had begun to leave him alone, leaving his shell and moving forward with his life. None of that would have been possible without her intervention. If Oliver somehow did discover what she had done, he would certainly hate her, but Kaitlyn knew that his hatred was a small price to pay for returning his life to him.

Picking up her phone to look at the screen, Kaitlyn sighed and tossed it onto her bed. She had checked her phone for any word from Jesse almost every ten minutes since she had woken up that morning. The anticipation was killing her, and she needed a way to get her mind off of him. Standing up from her desk, Kaitlyn walked downstairs to the kitchen, desperate for another cup of coffee, when she ran into Oliver leaving the room.

"Oh, hey Katie. How's the studying?" he asked before taking a sip of his coffee.

"It's going okay, having trouble focusing," Kaitlyn replied with a frown. She left out that the trouble focusing was due to her frustration at Jesse not responding to her. Oliver nodded sympathetically, before gesturing towards the stairs back up towards her bedroom.

"If you need a second set of eyes on something I can help if you'd like. You're probably still tired from all of the celebrating last night after the game, huh?" Oliver said. Kaitlyn froze at his words, doing everything in her power to not let her expression change. At the School Showdown, Britannia Heights University won and the entire campus erupted into a variety of parties. Many of her sorority sisters, Veronica and Mel included, went out to celebrate the victory... however, Kaitlyn did not join them. After being fucked in the locker room, she had trouble focusing; and knew that she'd be unable to face her friends, the feeling of fullness still so fresh in her mind. Kaitlyn had snuck back into the house, ensuring she did not have to face her family, before locking herself in her bedroom. From there, she enjoyed a long night of pleasuring herself, edging herself over and over again just as she had done the night before she and Jesse first had sex. The build-up and sexual denial had made their first time together that much more intense, and she knew that re-enacting that build-up would make her visit the next day all the more pleasurable.

'That is... if he ever fucking texts me the plan!' she thought angrily, exhaling deeply as the thought crossed her mind.

"Thanks, Ollie. I should be fine, I just need a bit of caffeine to help get me through the day," she said, plastering a smile on her face to hide the bubbling anger at Jesse that had begun to grow. Oliver's head tilted curiously, as he watched his sister's expression.

"Alright... but before you go can I ask you a question?" he asked, bringing a hand up to scratch the back of his head awkwardly.

"Uh... sure, go ahead," she replied, ice running through her veins. His tone had become serious, and that was never a good sign.

"Alright well..." he began, clearing his throat nervously. "We've always been pretty open with each other. Always there for each other and I feel like we can tell each other about our lives, right?"

"Yeah...?" Kaitlyn said, her hands squeezing her coffee cup as she did her best not to fidget.

"Okay, because I've been hearing some rumors. Mostly from Veronica and Mel the other night. I don't think they thought I heard, but they were talking about you sneaking off with some guy and wondering who it was and what you weren't telling them. Are you dating someone?" he asked, laughing nervously. "If you are that's great, but... I was wondering why you didn't tell me."

"Ollie, I'm not-" she began to say before he raised a hand to cut her off.

"Please, don't lie to me," he said, giving her a small, reassuring smile. "I know you only moved back because you wanted to keep an eye on me... especially after what I told you about Jesse. But he hasn't bothered me in a long time it's like he ignores me whenever I see him. I don't want you to put your life on pause because of me."

Kaitlyn's heart broke at his words; she had been so concerned with not wanting her brother to feel betrayed that she had almost caused herself to go to the point of sickness over her guilt. But here he was, reassuring her, even though she had always seen herself as the one to look after him. All of the justifications she had given about doing the right thing to protect Oliver had begun to waver; maybe he didn't need her to protect him anymore. But what would that mean for her arrangement with Jesse? Could she call things off? Would she want to end things with him?

"Okay..." she sighed, nodding in agreement. "I've been seeing someone, but it's nothing serious. Just... chatting with him. I doubt it'll go anywhere."

She kept it vague and high-level, hoping that it would be enough to satisfy her brother's curiosity. Since the night of the Theta Lambda Sorority party, however, he had been asking more and more questions about her social life. Now hearing that Oliver was aware Veronica and Mel had been lying about her using the upstairs bathroom, she knew that it was only a matter of time until the truth came out.

"Well, that's exciting!" he replied eagerly, beaming at his sister. "Who is it? Is it someone I know?"

Kaitlyn shook her head, trying to remain nonchalant about the question as she sidestepped around Oliver, going to get a cup of coffee as if they were simply discussing the weather.

"Oh... you don't know him," she said, her voice remaining steely. Keeping her responses short and to the point would hopefully get the message across she did not want to discuss it.

"Is he a student at BHU?" he asked, continuing to probe her for information. Kaitlyn bit her lip, thankful her back was turned to Oliver. Could he not take a hint?

"Yeah, he does. But drop it, okay? I don't want to jinx it." she sighed, the words coming out harsher than she had meant to. Turning around with her refilled coffee in hand, she could see the expression on Oliver's face, one of shock and hurt mixed together.

"I just thought that you'd talk to me about these things. We don't normally keep secrets from each other..." he said, scratching his head again nervously. "It just feels like... well, since Mel and Veronica knew you were seeing some guy, I was worried you weren't telling me because you were embarrassed by me."

The words felt like a dagger to her heart. Kaitlyn immediately began to regret the tone she had used with Oliver. Reaching out to gently squeeze his arm, Katilyn gave him an apologetic smile.

"Ollie, I'm sorry-" she began to say before he pulled his arm back.

"Don't be, I shouldn't have pried," he replied firmly, his tone matching the one she had used before. "Good luck with the rest of your studying, I guess."

Before she could respond, Oliver turned on his heels and rushed out of the kitchen, back upstairs towards his bedroom. With her free hand, Kaitlyn rubbed her eyes; feeling exhausted. Living a double life as she had been doing was beginning to take a toll. It felt to her as though she entered her arrangement with Jesse with the best of intentions in mind; to stop her brother's torment and to give him one final year of University where he could spread his wings and grow. However, it turned out she had become even more distant from her brother, and her actions had begun to give him cause for worry. How could he ever think she would be embarrassed of him?

Now, feelings of guilt over her attraction to Jesse came back tenfold. How could she sleep with the man who had caused his insecurities? How could she get on her knees and pleasure her brother's tormentor? How could she ride, or let him fuck her-

Kaitlyn shook those thoughts from her head. It was too easy to lose herself in memories of how Jesse made her feel and forget how Jesse had made Oliver feel. This was a transactional arrangement, and she needed to keep focused. She had gotten Jesse off five times; they had reached the halfway point of their deal... she could get through this and then she and Oliver could move on with their lives without Jesse.

Without Jesse.

The words caused a pang of pain in her heart. 'No! He means nothing to you.' she thought, feeling as though her mind and her heart were at war with one another. It was time to return to studying, and hopefully, she would have a better time focusing than she did before her conversation with Oliver.

As she entered her bedroom and closed the door behind her, Kaitlyn let out a sigh of relief. Over the past few weeks, her bedroom had become the one place she felt safe to let her guard down. It was the one place where she did not need to worry about explaining herself or her whereabouts, where she was not concerned with who would see her, and who she would be seen with. Even when Jesse had come to her house when they had sex for the first time, they never made it to her bedroom... instead, he had taken her on Oliver's bed.

The memory returned a surge of longing to Kaitlyn; reminiscing about the feeling she had as he roughly fucked her on Olvier's bed, how his cum had stained the blankets... before he left her without a second thought. She had received closure at the Theta Lambda party, yet it remained a sore spot. Suddenly, a soft buzzing sound from her bed snapped her back to reality and Kaitlyn had to stop herself from all but diving onto the mattress to snatch up the small Jesse, and a soft gasp escaped her lips. 'Finally...'

Opening the locked phone, she hungrily read his message, her breath catching in her chest.

Jesse: Hey, sorry about the delay. The guys just left so I have the place to myself. Come over.

Without a second thought, she quickly typed out a response, before once again throwing her phone onto the bed.

Kaitlyn: Just going to hop in the shower then will head over. Should be there in about an hour.

She didn't wait for a response, and instead made her way down the hall quickly to the bathroom two doors down, before having a steaming hot shower. The moment she felt the heat falling on her skin, Kaitlyn felt her internal struggles melting away. Yes, a part of her deep down knew that their arrangement was still wrong, but there was no room for second-guessing. She had learned previously to simply obey when Jesse gave her a command, and that it was in her best interest to focus on the task at hand. The sensation of her body being washed awoke memories of Jesse's hands caressing her, holding her, squeezing her, and filling her, and the anticipation was filling her to the brim...

But those thoughts would have to wait. As much as she loved to fantasize and remember how he made her feel, Kaitlyn knew the real thing was waiting for her, just on Greek Row.

With a towel wrapped around her body, Kaitlyn returned to her bedroom; noticing her bedroom door was left ajar. She frowned and thought, 'I could have sworn I closed this...' It didn't matter now though, all that mattered was getting herself ready for Jesse. She dug through her closet for something cute; pulling out a pair of black leggings, and a white with a navy blue striped t-shirt, with a black zip-up sweater on top. Her hair, still damp from the shower was twisted into a bun on her head; and it was time to leave.

Zipping her sweater, Kaitlyn walked out of her bedroom and made her way towards the stairs, but stopped as she reached Oliver's room. His door was closed, but she needed to make one last effort with Oliver before she left. With a soft sigh, she gently knocked on his door, before opening it and sticking her head into the room.

"Hey... I'm just going to run to the sorority house, I have some things to catch up on with the girls," she said, as she peered around the door. Oliver was lying on his bed with his laptop out, watching videos online with headphones covering his ears. Seeing movement out of his peripheral vision,

"Sorry, what?" he asked, his face remaining a steely mask to hide his true feelings. Kaitlyn's words dried up in her mouth though, as the memory of Jesse taking her on Oliver's bed flashed before her eyes. Her brother was laying in the exact place she had been bent over, her back and ass covered in Jesse's hot seed.

"Oh... uh, I'm going to the house. The sorority house," she repeated, more flustered now that she had come face to face with her brother in his bed.

"Mhmm, not going to see your secret boyfriend?" Oliver said, raising an eyebrow sarcastically. The words cut Kaitlyn, but she remained resolute, keeping a soft and pleasant smile on her face.

"No... just going to the house. I'm still sorry, Ollie," she replied, gesturing back towards the door. "Maybe we can talk more when I get home? To clear the air a bit...?"

"Sure. Say hi to your boyfriend for me." Oliver replied once more, before pulling his headphones back over his ears. The suddenness told Kaitlyn the conversation had ended. With a sigh, she nodded, closing the door behind her. It was obvious that Oliver was hurt; how he felt as though she was embarrassed by him and did not want to tell him about her dating life. How could she though?

Kaitlyn made her way downstairs and out of her house, feeling conflicted. The walk felt as though it had taken a lifetime, and thoughts of her situation wrestled in her mind. While it was true she had entered this deal with Jesse to protect Oliver, she would be lying if she didn't admit that feelings had grown. With their most recent meetings, it had begun to feel as though Jesse had felt the same. Even for the invitation today, it wasn't the commanding, degrading tone he had given her previously, it was almost flirtatious.

If he did reciprocate her feelings though... what then? Kaitlyn knew that they could never be public about their relationship as there was too much of a stigma in her friend group about Jesse himself as well as his frat. While her parents weren't aware of Oliver's bullying predicament, they would certainly sense Oliver's anger towards her sister's choice of partner. Then there was the matter of Jesse's friends, Would they respect his wishes and continue to leave Oliver alone? Or, would the thought of their leader fucking his sister simply provide them more ammunition to torture him with?

These worries continued to plague her mind as she walked, her body moving on autopilot as she ventured to the Britannia Heights University campus and Greek Row, the street housing all of the frats and sororities. Theta Lambda was close to the corner, only three houses away and she would have to pass by it on her way to the Sigma Sigma Omega frat house. Kaitlyn hurried past it with her head down, praying no prying eyes were peering out the window, and noticed their sister heading further along the street.

Almost reaching the far end of Greek Row, Kaitlyn arrived at her destination: the Sigma Sigma Omega frat house. Compared to many of the other houses on the street, it looked as though it had been trashed. Having undergone several parties per week for close to fifty years, even from the outside any passerby could tell that it was the place to party, let loose, and make bad decisions. It was the exact kind of house that parents would warn their newly enrolled children to stay away from, the kind of building that you would see on the front page of a newspaper because of some sort of scandal... and she was about to head into the lion's den on her own.

With a deep, nervous exhale, she walked up to the door and knocked. Waiting for an answer made the seconds drag on, as she looked over her shoulder anxiously and hoped nobody would see her. A lone woman waiting to be let into a frat house in the middle of the day usually was the sign of a booty call... which wasn't far from the truth today. Finally, the door opened and she was greeted with the sight of Jesse, shirtless, his arm still in a sling, and with a wide smile on his face... a smile of joy.

"Hey, Katie!" he said happily, stepping aside to usher her inside. "Come on in, turns out there are two of the brothers who are still here but are sleeping off hangovers so they won't bother us."

Her eyes widened at the revelation; she had hoped that nobody would be present. If they had sex, there was no way she would be able to keep the sounds of her pleasure in check, Jesse would make sure of that. What if they saw her go in or leave? Would word begin to spread that she had been fucking Jesse?

"Oh... o-okay," she said, stepping inside. There hadn't been a direct conversation about them doing the sixth hookup; he was normally very direct in his intentions to get off with Kaitlyn. However, his words from the locker room echoed in her mind, 'We can continue where we left off, without having to worry about someone interrupting us'. That was enough of an implication to know that she needed to tread carefully; her relationship with Oliver had been rocky enough and any news of her and Jesse's relationship could shatter it entirely.

Kaitlyn followed Jesse inside the house, and for the first time, she saw how the Sigma Sigma Omega frat lived. The inside was much nicer than the outside. The men either took pride in their living areas, or they had an exceptional maid. She had never attended a party at the Sigma Sigma Omega house before, but had heard stories of how out of control they would get; people being injured, arrests, damage to the property... they were campus-wide horror stories, yet they always received a packed house when parties were thrown. Jesse led Kaitlyn upstairs, to a row of bedrooms. The majority of the doors were closed and as they had at the Theta Lambda Sorority house, there were small white boards with each of the resident's names for the rooms, as well as some other decorations. 'What are men's obsession with drawing dicks?' she thought, frowning as they finally reached Jesse's bedroom.

"Here we are, come on in," he said, stepping aside so she could enter his bedroom. The room itself was fairly small, which was to be expected in a single bedroom of a frat house. His bed was pressed against the far left corner, with his dresser and a TV on top of it pressed into the right corner. The floor was covered in dirty clothes, discarded around the room haphazardly, and textbooks and study books just as carelessly discarded. Kaitlyn took in the room in an instant, and as she did... it dawned on her that they were alone, and a bed was so close. Kaitlyn's heart began to pound like a drum in her chest, and her body began to ache for his touch. Without a word, she sat down on the edge of Jesse's bed, turning her gaze up to meet his.

"So... what now?" she asked softly, her large innocent eyes doing nothing to hide the burning desire growing inside of her. Jesse closed the door, before climbing onto the bed next to her.