Life of Leo Kennedy Ch. 02

(Disclaimer: Hey again! Thank you to all who read and rated chapter one! As always, all characters depicted are over 18. From now on, each chapter will feature Leo's partner for the next, so feel free to make your guesses!)

Chapter 2: The Monday After

It had been two days since that party, and Leo was still in disbelief over what happened with Jasmine. It was almost like he could still feel her warm tongue sliding up and down his cock.

After their "fun" had concluded, the two had went back upstairs, meeting back up with Tyler and Max, and actually enjoying the rest of the party. Leo had even ended up giving the rest of them rides home, since he was a little too preoccupied to drink.

But today was Monday, which meant school. First period was history, which went by quickly. Second was math, which went by less quickly. During lunch, Leo ate with Tyler and Max, same as usual. He would always sit between them, so they could be in ascending height, with Max being shorter by about 2 inches, and Tyler being taller by about 4. Tyler was a bit bulkier, with black hair. Max was slim, with lightly tanned skin he gets from his Japanese parents.

Leo had even seen Jasmine around a couple of times, but the two didn't say anything to one another. All they did was smile and blush. Leo thought all day about what he'd say to her, but he couldn't think of anything that wouldn't totally embarrass him.

Once lunch was over with, it was time for biology with Ms. Howard.

God Leo loved Ms. Howard.

He walked into the classroom, sitting in his normally assigned seat, looking up to see her. Bethany Howard was in her early-mid thirties, and was a total smokeshow. Perfectly hourglass shaped body. Long, cascading black hair. Curves in all of the best places. And on top of that, taller without high heels than most of the male teachers in the school, and she always wore the high heels.

Class went about as normal. The class did mostly review on a recent test they'd had. After a while, the class had begun to get louder, paying less attention, and Ms. Howard put an end to it. "Alright, settle down everyone!" she called out in a stern, yet velvet soft voice. "I'm hoping you all remembered to read chapters 7-10 of your textbooks, because this upcoming assignment will focus mainly on that content. You'll be assigned groups of four." she explained. She then began to list off names, and Leo listened until he heard his. "Leo, Cheyenne, Danni, and Lauren." Ms. Howard announced.

Just as she finished that sentence, one more student entered the classroom: Emily.

Usually a girl dressed in all designer clothing, Emily quickly and quietly made her way to her desk in a hoodie and yoga pants. Her two friends, Bella and Tahlia turn their seats toward her, checking on her and making sure that she's ok. Even though the trio were usually rude to other people, they were always incredibly caring about each other.

Leo didn't really hear what any of the girls were talking about. Maybe something about Brandon, Emily's boyfriend. He tried to listen closer, but was interrupted by an unfamiliar voice.

"Hi!" called out Cheyenne, one of Leo's new group mates. Cheyenne was a girl on the chubbier side. Not fat, but voluptuous. She had black hair with bangs, and a white streak. Cheyenne had a kind of goth aesthetic to her, and she was wearing a tight black sweater that her large breasts were stretching, and a cute black frilly skirt with fishnets on thick, powerful legs. "I'm Cheyenne." she introduced herself nervously.

"Nice to meet you, Cheyenne. I really like your outfit!" called out the voice of Danni. Danni was a guy, through and through, but no one would blame you if you thought he was a girl. Danni was short and petite, with bubblegum pink, shoulder length hair. He had a higher voice, and always dressed cutesy and feminine.

"Nice to meet you both!" Leo told both of them. He glanced them both up and down again before he remembered their missing partner. "Where's Lauren?" he asked.

Leo and Lauren had actually hung out a couple of times, usually ending up smoking weed together at the house of a mutual friend. Lauren had only just gotten out of her chair to make her way over to her group. "Sorry! I kinda forgot." she laughed. Lauren had long, wavy, dirty blonde hair. Leo could never get a good read of her body type, since it was usually covered by baggy hoodies and jeans, similar to himself.

"I was thinking we'd each read a chapter of the textbook tonight on our own, and then start working on the assignment tomorrow in class. We'd each do the part of the assignment based on the chapter we read." Cheyenne suggested, getting nods of approval from the other three.

"I like that! I'll take chapter 8." Danni volunteered.

"I'll take 10." Leo said.

"I guess I'll read 9." Lauren shrugged with a smile.

"Great! Then I'll have chapter 7." Cheyenne grinned, followed almost immediately by the bell. "See you guys tomorrow!" she called out, waving as she left.

The three students exchanged Snapchats, and made their way to their last class of the day, which for Leo, was art. As he left the classroom, he saw Emily, Tahlia, and Bella all hug before parting ways. Emily walked in the same direction as Leo did, but entered the library instead of any classroom. Not too concerned, Leo made his way to Mr. Brants art room.

Leo was an incredibly talented photographer, and was very excited to submit some of his new shots for an assignment. He was so eager for feedback that he stayed after class to get a personal, real time grading from Mr. Brant.

Soon though, it was time for Leo to go home. Leo had already texted his moms beforehand that he might be late getting home, so he wasn't too worried about that. As he made his way through the hallway towards the doors, he stopped dead in his tracks, hearing a noise coming from the library. It sounded kind of like crying. Leo opened the doors, looking around to find the source. And what he saw, was Emily curled up on one of the librarys couches, crying by herself.

Leo almost did a double take and left. Emily had only ever been nothing but rude to him. But then again, she was crying, and he would feel like an absolute dick if he didn't at least ask if she was ok. He slowly made his way over, sitting next to her on the couch. "Hey, Emily. Are you alright?" he asked.

Emily looked up, tears slowly running down her pale face. "Like you even care. You probably just think I'm a bitch."

Leo almost agreed, honestly. She was mean to everyone except Bella and Tahlia. It was never really that bad though. Mostly just mean comments. "You're not the nicest girl in the world. But I wouldn't call you a bitch." Leo told her.

"Just shut up. You don't know anything." she huffed, turning away from him.

Leo shrugged. "Alright. I'll leave you alone." he said, standing up to leave.

"Wait!" Emily called out, looking up at Leo. "I'm sorry. Please stay." she asked softly.

Leo slowly sat back down and looked her in her brown eyes. "Alright, alright. I'll stay." he smiled.

"It's just... Brandon cheated on me at that party. Bella told me, and when I asked him about it, he called me a crazy bitch." she explained shakily. "I... I don't know why I'm even sad." she sniffled. "I am a bitch. I'm a bitch to you and your friends, to the rest of the girls, to everyone." she said with the deepest of breaths.

Leo slowly raised his hand up, placing it gently on Emily's shoulder. "Hey. It doesn't matter if you've been mean in the past. No one deserves to be cheated on." he consoled her. "Brandon is a fuckin' dick anyways." he laughed, getting a small laugh out of the crying girl.

Emily smiled, wiping most of her tears off of her face with a final sniffle. "Thanks, Leo. I'm... really sorry for being like, a bitch to you."

Leo was surprised. A week ago, he would've never believed that Emily would be saying something like that to him. Especially in this kind of situation. "Thanks, Emily." he laughed. Emily checked her phone and groaned.

"I told Bella and Tahlia to go home without me. Fuck. I don't wanna walk home." she sighed.

"Of course." Leo thought to himself. He knew what he had to do. "Would you like a ride home? My car's in the parking lot." he offered.

"Really? That would be so awesome, thank you!" she smiled, giving Leo a small hug before awkwardly pulling away.

The two walked out of the school together, out into the parking lot. Leo even opened the passenger side door of his car for her, something he assumed a rich girl like her would be used to, though his car was on the cheaper side. The two didn't talk much on the ride to Emily's house. Their interactions were mostly limited to Emily shooting quick glances up and down Leo.

As they rolled into Emily's neighborhood, the houses only kept getting bigger. Emily told Leo the number of her house, and soon after, he pulled into the driveway. The two began to argue about whether or not Emily would pay Leo for driving her, with Emily eventually convincing Leo to come inside so she can grab her wallet.

The walls of Emily's house were lined with expensive art, and family photographs. When the pair reached her bedroom, Leo was surprised to see that it was decorated rather basically with plain white and black, save for a closet filled to the breaking point with designer clothes. Emily shoots Leo another quick glance before starting to rummage through her desk.

"Really, Emily, I swear it's alright. You don't need to pay me." Leo said.

"I know I don't need to, but I want to. And I know you won't take my money, so..." she trails off, grabbing something from her desk and chucking it to Leo.

Leo caught the small object out of the air. It felt plastic in his hand. He looked down to see an unopened condom, and his eyes went wide. "Emily..."

"Brandon can fuck whoever he wants, apparently. So... then so can I." she said firmly. "But only if you want to."

Leo thinks it over for a second before smiling. "I'd love to."

Emily giggles, removing her hoodie, followed by the shirt underneath, and then finally by her yoga pants to leave her in very expensive looking lace black underwear. She climbs onto the bed as Leo strips down to his own blue boxer briefs. Emily peels her panties off, tossing them aside and spreading her legs to reveal a hairless, pink pussy.

Leo grinned, lowering himself to face level with Emily's pussy, closing his eyes as he gently kisses and slowly licks it. Emily moaned softly, tensing her legs as she got more and more wet. Leo's own cock grew hard in his underwear, throbbing against the fabric. The speed and pressure of his licks begin to speed up, now flicking his tongue over Emily's clit.

"Fuck. Yes." Emily groaned, grabbing her phone and opening the Snapchat camera. She began to film Leo eating her out with her one hand, as she ran her clear acryllic nails through his hair with the other.

Leo looked right into the camera and smiled, precum starting to leak from his tip. He slowly began to suck on Emily's clit, inserting two fingers inside of her, moving them in and out.

"I... oohhhh... don't want fingers! I want... ahhhh... that dick!" she groaned.

Leo listened, sliding his underwear completely off, straightening himself up for Emily to see every inch of his bare cock. He looked into her eyes as he rolled the condom onto it.

"Fuck. That's way bigger than Brandons." she grinned eagerly.

He climbed on top of her, using his right hand to guide his tip inside of her. He only pushed in a couple of inches, but she was already moaning hard. Leo slowly moved his hips back and forth, stretching the petite brunette nice and wide.

"Jesus Christ! Fucking give it to me, please. I can take it." she begged, and he obliged.

Leo sped up his thrusting, causing Emily's legs to shake. She, however, continued recording several videos for god knows who. Leo grunted with almost every thrust, gliding in and out of her pussy.

"Yes! This is what real fucking dick is! Feels so fucking good!" she cried out. Her bed was now rocking hard as Leo railed her. Her legs locked behind him as her small titties bounced wildly. "I'm gonna fucking cum!" she exclaimed.

Leo only started to fuck harder. He could feel himself getting closer as well, even through the rubber.

Emily cried out in ecstasy, her legs almost vibrating in pleasure, and similar noises escaping her mouth.

Leo slowed down to give her a bit of breathing room for her to calm down. "I'm close too." he groaned.

"Cum on my face! All over!" she begged, still in bliss.

Leo pulled out, quickly removing the condom fron his cock and positioning himself closer to Emily's face. He jerked himself off quickly, precum flying from his urethra. He let out a loud moan before cumming all over Emily's face. It got on her lips, her forehead, and some even in her hair, while the remainder dripped onto her chest.

Emily laughed in glee, taking a selfie of herself with all of Leo's jizz on her face. "Thanks, Leo. So much. I really needed that."

"I should definitely be the one thanking you." Leo laughed back, standing up and wiping himself off with a nearby tissue.

Emily reached onto her bedside table as Leo began to dress himself, grabbing her wallet for real this time. She pulled out three $100 bills, forcing them into Leo's hand as he finished getting dressed. "Take it and say thank you." she laughed.

Leo graciously accepted the money, stuffing it into his pocket with a smile. "Thank you." he parroted.

Leo left Emily's house, getting into his car and driving away as meanwhile, she was sending the videos that she took of them to her two friends. Leo wasn't thinking about that all, though. He had a textbook chapter to read.