My Brothers Keeper Ch 08

Kaitlyn sighed as she flopped onto her bed, rubbing her eyes in annoyance. For the last several weeks, her brother, Oliver, had been angry and refused to talk to Kaitlyn and their parents had begun to notice it. Normally, Kaitlyn would grit her teeth and let Oliver be angry, after all, it was her fault that he was feeling hurt, but once their parents started to try getting themselves involved to "help them reconcile", things had spun out of control.

The twins had been at odds since Oliver discovered Kaitlyn had been seeing someone secretly, which she did not want to tell her brother about. For years they had been each other's confidantes, being able to share their secrets, their wins, and their losses. But Kaitlyn had no way of telling Oliver that the man she was seeing was the man who had tormented him for years... let alone that they were simply using one another for sex. Their deal was quickly coming to a close, and all Kaitlyn had to do now was make her last two payments, and then Oliver would be free. After that, she could reconcile as she'd have nothing left to hide.

At dinner, her parents had poked and prodded about the tension between the siblings, prying for any reason why Oliver refused to talk to Kaitlyn. Neither of them wanted to share it with their parents however, knowing that if news of Kaitlyn dating came out they would want to meet her mystery man, and then they would know that Oliver felt as though she were embarrassed of him. It'd be even more difficult to explain the situation to their parents, as they were unaware that he had continued to be bullied into University, believing that his suffering had ended in high school. She was just thankful that they didn't know who Jesse was so that if they were to see or meet him, they wouldn't be able to connect him to their son's plight.

"Just leave it alone, fuck!" Oliver had shouted, before storming off to his room. His anger had begun to bubble over, impacting the entire family. Kaitlyn knew that she had to do something soon, or else risk her relationship with her brother forever.

While lost in thought, her phone began to buzz in her pocket, and in one swift movement, Kaitlyn pulled it out with a smile on her face. Since New Year's Eve, she and Jesse had been texting daily. Settling back into their final semester of school had caused them to not be able to spend more time together, but it was clear that they both were craving some sort of connection. Even though it had been only a few weeks since their last night together, every message from him seemed to ignite that fire of desire within her.

Jesse: Hey beautiful. How's your night?

Jesse: I need a distraction from studying haha

Kaitlyn bit her lip, mulling over her response before holding her phone up to snap a selfie; a photo of her splayed out on the bed with her hair a messy halo around her face.

Kaitlyn: Aww, it's not going well? Hopefully, this helps :)

Jesse: You know it does. Damn... wish I could see you in person. I'm drowning in my stats course

Kaitlyn frowned at his message. She had taken multiple statistics courses throughout her time at Britannia Heights University, all of which she did extremely well in. With her hopes of becoming an engineer, math was something she was experienced with... and if that was where Jesse had been struggling perhaps she could help him.

Kaitlyn: I took stats a couple of years ago. I could help if you're looking for an extra set of eyes on a problem.

Jesse: Are you sure? I can't imagine ANYONE wants to suffer through this shit, let alone someone who has already done it lol

Kaitlyn: I don't mind at all :)

Kaitlyn: Want to meet at the library tomorrow night? I have classes until 5 but can meet any time after that.

Jesse: You're a lifesaver, Katie. I'll see you then.

Kaitlyn's heart swelled while reading his responses. While it wasn't going to be the raw, passionate nights they had previously spent together, it was going to be a chance to see Jesse again. After New Year's she had begun to think that their arrangement didn't need to end after their 10th session. Perhaps, they could continue to see each other in secret. Once Oliver had no more issues with bullies, they graduated and went out into the world, she could move out and spend more time with Jesse. With enough time passed, maybe they would no longer need to hide their relationship. It was unlikely that Oliver would ever forgive Jesse, but after some time maybe the pair could at least get along for her sake.

The thought of seeing Jesse though immediately caused a hunger to grow within her. Masturbating had lost some of its luster since she had started having sex with him, and knowing that they would be together again soon did nothing to help curb her libido. The next day would be difficult, to say the least, and she was thankful they would be somewhere where they couldn't have sex lest she simply throw herself at Jesse.

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As expected, the next day felt like one of the longest she had suffered through in a long time. Every few minutes she felt compelled to look at the clock on her cell phone, minutes ticking by as if they were hours. Conversations she had and lectures she attended sounded like white noise in the back of her mind, her clothes felt restrictive, and it was impossible to focus on anything. Whenever her mind began to wander, Kaitlyn's imagination kicked into full gear; flashing the sight of Jesse's body across her eyes, his scent filling her nostrils, his taste on her tongue, and the feeling of warm cum spraying into her eager pussy. Had anyone been paying attention to her during her lectures, they would see a squirming, near hyper-ventilating mess of hormones, one who was seemingly a single touch away from orgasm.

It was made all the more difficult with her choice of outfit for the day. Kaitlyn wanted to dress casually so as not to appear too eager, but she wanted to look sexy enough that it would tease him as much as she felt she was being teased. Wearing a simple dark grey blouse, and blue skinny jeans, with her boots and a heavy black jacket, her clothes made Kaitlyn feel as though she were being constricted. Every movement had the fabric pressing between her legs, teasing her pussy... she was becoming desperate for any sort of relief.

'No! You need to focus, you're here to help Jesse with his homework, NOT have sex.' she had to continuously remind herself. Even as she made the walk through Campus to the library, her mind continued to be filled with thoughts of sex. Her eyes locked on the Arts Building that they had met in before, looking over the parking lot that they had left from the first time she had jerked Jesse off...

"Uh... ma'am? You need to swipe your Student ID card." an employee of the library said as Kaitlyn tried to unsuccessfully walk through the small entry gate leading into the library. Blinking slightly, she looked down and realized that she had drifted off, lost in thought, and had made it to the library. With a feeling of embarrassment, she pulled out her Student ID, scanning it as the gate slowly swung open to allow her access.

The library itself was a massive, three-story building with all of the administrative offices on the bottom floor, meeting rooms that could be booked on the second, and quiet study areas on the top floor. Books and other resources that students could access were spread out throughout the three floors, and tonight it seemed there were not many students coming to study. Whether that was because many were at the cafeteria for dinner, still attending evening classes, or because it was still early enough in the semester that students simply studied at home or in their dorms, it was a lucky break for Kaitlyn.

She quickly typed out a message to Jesse, hitting send before craning her neck to see if he was sitting somewhere nearby.

Kaitlyn: Hey! Just got to the library, where are you sitting? :)

Jesse: Just up on floor 3! Far back left corner, it's dead up here tonight so I can actually focus

Jesse: Helps so you don't have to worry about anyone seeing you with me ;)

Frowning at the last message, she rolled her eyes before heading towards the stairs. Venturing up to the third floor, her heart began to pound in her throat; the anticipation of finally seeing Jesse building up within her. She followed his instructions to where he was seated, and the moment her eyes laid on him it felt as though her breath caught in her chest. Jesse was leaning back in his seat, his brow furrowed as he read a passage in his statistics textbook. He wore a simple white t-shirt and jeans, the clothes hugging his muscular frame perfectly. At the sound of Kaitlyn's footsteps approaching, he looked up at her with a smile.

"Finally, I thought my hot tutor would never show up," he said playfully, pulling out the chair next to him and gesturing for her to sit. Kaitlyn obeyed, sliding into the seat with a soft contented sigh.

"Sorry, it's been a long day and I felt like I was in a bit of a daze," she said, pulling off her jacket, and hanging it over the back of her chair, and sliding her bag underneath the table.

"Oh? Bad day?" he asked, frowning slightly in concern. Kaitlyn shook her head, giving him a reassuring laugh.

"No, it just felt like it was really long. I was looking forward to coming to see you so..." she replied, trailing off slightly in embarrassment. Jesse raised a surprised eyebrow before laughing.

"Wow, you really like statistics, huh? I lucked out!"

Kaitlyn rolled her eyes sarcastically, letting out a quiet giggle as she did. "Oh, that's exactly what I've been looking forward to. I've been using you just so I can relive my freshman years by taking statistics again... why are you taking stats in your senior year? Just haven't taken it yet?"

"Uh... well I took it in my freshman year..." Jesse replied sheepishly, running a hand through his hair, doing his best to hide his embarrassment, although not doing it very well. "I failed though. It's a mandatory class for my degree so I figured I'd wait until I had a lighter workload but between classes, the frat, football..."

"It just kind of got away from you?" she asked, getting a nod from him in response.

"Pretty much. Math has always been one of my weaker subjects, and I just can't wrap my head around stats. I somehow ended up having all of my math classes that I flunked as a freshman come up this semester and I feel like I'm drowning in work now."

"Ouch, what other math courses do you need to take?" she asked, propping her chin on the palm of her hand. "I like math but would hate to have a bunch of those classes lined up in one semester."

"I just have this statistics course and calculus," Jesse said with a dejected sigh. "If I can't maintain a 70% I can't play football for the rest of the season, and if I fail these courses then, well... I'll need to take another semester to do them."

Kaitlyn listened to Jesse intently, nodding along as he spoke about his predicament. New Year's had been the first real conversation that the pair had had together, and this was the first time she was seeing the student side of Jesse's persona. In public, he often put on a cocky facade to impress his friends, with that often leading to bullying Oliver, but now he seemed like any other student. Vulnerable, wanting to pass his courses and struggling... just like anyone else. Kaitlyn found this vulnerability endearing... and it made her want to comfort him. Reaching out, Kaitlyn gently took his hand in hers, squeezing it.

"Don't worry, I'll help you! We'll make sure you keep your grades up and I can help with your assignments," she said, smiling widely at him. Jesse looked at her, his expression that of discomfort.

"But... why?" he asked, not pulling his hand back but simply looking at it. "I don't know why you'd be willing to help me... I figured the only reason you were hanging out with me was because of our deal. It's not like you have much of a choice, but why are you going out of your way to help me?"

Kaitlyn froze for a moment, hesitating. Everything she had been thinking, wanting to say... now would be a perfect opportunity. But, what if Jesse did not feel the same way? If Jesse didn't share her feelings, she would still need to fulfill her end of the deal. Would she be able to continue satisfying him, knowing that she would never get her feelings reciprocated? If he did feel the same... how could they possibly be together with his and Oliver's history? With a slow, steady exhale Kaitlyn needed to choose what to say... and knew that Jesse responded better to honesty.

"Well..." she began, swallowing the lump that had begun to grow in her throat. "You're right that before we, um... made our deal, I wouldn't have helped. After everything that happened between you and Oliver... I hated you. But, we've gotten to know each other better and... I'm starting to enjoy spending time with you. With or without the sex."

As he listened to Kaitlyn speak, Jesse's look of discomfort began to slowly melt away, being replaced with a soft, shy smile.

"Hopefully you still see the sex as a bonus?" he asked teasingly, getting a sarcastic eye-roll from Kaitlyn in response.

"Yes, yes. The sex is lovely," she sighed jokingly, shaking her head. "But honestly, you're not the same person that I saw before we started this. You've grown a lot, and you've shown me a different side of yourself."

"I definitely feel different," he said, nodding in agreement. "It's strange, I don't normally get close to the women I'm seeing. It's usually kept pretty casual... but, I like spending time with you Katie."

Hearing his words made her heart feel as though it were swelling. Jesse felt the same! All of the worries she had felt disappeared in an instant, even if Oliver knew about this it didn't matter because Jesse had become a different person because of her.

"I'm... really glad to hear that, Jesse," she said softly, squeezing his hand gently. "But I have to ask... are you sorry for what you did to Oliver? How you and your friends treated him? I know that you've kept your word and you've left him alone, but I've just been curious."

"Well... when we were doing it, it just felt like a funny thing to do, you know?" he said, his words instantly replacing the glowing warmth that had been in Kaitlyn's heart with an icy steel. Despite her feelings, she cared for Oliver more than anyone, and she would still do anything to protect him, even if he hated her. "I always thought that's what I was supposed to do, it's what my friends had always done. I was shocked when you agreed to hook up with me to get me to leave him alone and as we got closer I started to see just how much it hurt you. So, I am sorry for it. If I could go back and change what I did though, I don't think I'd change a thing because it brought us together."

Kaitlyn sighed and nodded, giving his hand an appreciative squeeze. "Thank you, Jesse. I appreciate your honesty, I hate how he was treated but... I know that you're not the same person anymore and you wouldn't do anything to hurt him. I just wish he knew that..."

"I know, I do too. But if the least I can do is leave him alone going forward I'll happily do that," he said, his thumb gently stroking the back of Kaitlyn's hand. "Now! I need your help because I'm basically in the dark about everything we learned so far this semester."

With that, Kaitlyn nodded confidently and dove into the textbook, feeling lighter than she had all year. The air of tension that had started to grow around the pair during their conversation quickly began to disappear as Kaitlyn explained the concepts from the textbook to Jesse, the couple laughing and flirting every as they went. She was slightly taken aback by how quickly he picked up the concepts; Kaitlyn had figured that he was just a stereotypical dumb jock and that 70% would be the best he could hope for... but it was clear that with a little bit of extra help, he could even surpass that.

Finally, Jesse leaned back in his chair with a triumphant grin.

"Fuck, I can't believe it! You're really good at this shit," he said excitedly, looking over the answers he had jotted down to the textbook questions. "Seriously, Katie, thank you so much, you have no idea how much this means to me..."

"Happy to help! But this isn't a one-time thing. Let me know what you go over in your next lecture and I can meet and help with that t-" she began to say before Jesse leaned in and pressed his lips to hers. Kaitlyn let out a soft whimper against his lips, melting into the kiss. She had been holding back her urges the entire time they worked on his studying but finally, she could give in. Jesse slid a hand onto her thigh, slowly moving it up to tease her pussy over the fabric of her jeans before Kaitlyn jumped in shock. Pulling away from the kiss, she looked around the library nervously.

"J-Jesse! What if someone sees us?" she whispered hastily, nerves gripping her in an instant. Jesse leaned back in to kiss her, the hunger in the act being all the answer she needed. Taking one of Kaitlyn's hands, Jesse placed it on his lap and she could feel his growing bulge. He needed this just as much as she did. Maybe after all of the work he put in... he deserved a break. No, she deserved a break.

Pulling away from him once more and looking around nervously, Kaitlyn smiled, slid off of her chair, and inched her way beneath the table. As she did, Jesse unbuckled his pants and slid himself securely under the table; ensuring that nobody would see what was happening. Memories of their time in the Art Building bathroom came flooding back, but unlike their second time hooking up there were so many more opportunities to be caught... and it was thrilling. Reaching up, Kaitlyn pulled his pants down just enough to release his cock, and without a second of hesitation, she began to lick and kiss along his shaft, relishing the taste of his skin.

Jesse sighed happily and leaned back in his seat as she gently licked along his manhood, kissing and stroking it. Her tongue began to flick along his cock, exploring from base to tip until she finally took him into her eager, salivating mouth. The gentle sound of slurping could be heard from beneath the table as she gently bobbed her head up and down. Unfortunately, there wasn't a lot of room underneath the table for full movements so the options Kaitlyn had were small movements up and down with his thick cock almost in her throat, or to constantly deep-throat him. She had waited so long though, slurping him slowly and teasingly was all she needed; desperate to prolong their foreplay.

Kaitlyn continued to slurp along his cock for close to ten minutes, just slowly working him and pushing herself deeper slowly over time. Any time Jesse came close to finishing, she would slow down, edging him over and over again. That was... until she heard voices above her.

"Hey, Jesse! What's up, man? Didn't expect to see you here this late," the sound of Brian, one of the bullies in Jesse's group of friends said. The table creaked as someone sat on top of it, feet hanging down next to Jesse and the hidden Kaitlyn. Her eyes widened in horror; Jesse's friends had shown up while he was getting a blowjob from her. "Whose coat is that? You studying with someone?"

"H-hey guys," Jesse said, trying to keep his voice from giving anything away. His cock began to grow in Kaitlyn's throat as he became more aroused by the situation. "Yeah, just getting some studying done with a girl from class."

"Oh? The semester is just starting and you're already working on someone, nice!" Another voice, that of another of Jesse's friends, Kyle, said. "Can't wait to see her. Maybe you can introduce her to us, could be fun if you blow your shot for us to take a crack at her."

Hearing them talk about her in such a degrading way made Kaitlyn feel disgusted. Even though she hated the rest of Jesse's friends... she couldn't help but get more turned on in the situation. Being careful not to make any more sounds, she pushed herself deeper, taking Jesse's cock deep into her throat. The sudden fullness made her throat constrict around his shaft as she made small movements to stimulate him. Jesse jumped slightly at the feeling, his breath slipping out in a small gasp.