My Boring, Shitty Life Ch. 10

Riley is just starting out in life, but thus far, is unimpressed. He's still in high school and having trouble finding himself in a world where everyone around him feels like they have it all together. In the past few weeks, he's joined a motorcycle club and started wearing his grandfather's legacy cut, gotten his first tattoo, rescued a damsel in distress, crushed on a few different girls, and gotten into a few fights. Recently, he was used and abused by the older woman next door as repayment for saving the damsel. There's also a party on the horizon. Things will heat up bit by bit along the way. All characters mentioned are over the age of eighteen, because, reasons, and as always this is a work of fiction.

It was finally Friday. Matt and I were getting ready for the party when his sister Kelsey poked her head in the room. "Awe. Don't you look cute. Getting all dolled up for your boyfriends at the party?"

Matt threw a pillow at her, but she closed the door just enough to block it as we all laughed.

"Hey Kelse!" I greeted her, still chuckling. "You wanna come with?"

She pushed the door open, cocked her hip to the side, and scrunched up her face. "To a high school party? Hard pass." I looked her up and down as she leaned on the door frame. She was wearing purple silk pajamas with low cut shorts and sliding her foot seductively up and down her calf.

Matt gave me a 'dude, no, what are you doing?' look. I ignored him. "C'mon. It'll be fun. I'll even let you sit in the truck with me. Matty here can sit in the bed."

She smiled. "Fun as putting my baby brother out sounds, still no. I'm over high school. You boys have fun." Our eyes locked and the look she was giving me spoke bounds. She knew I was checking her out, and wanted me to know that she knew. She was flirting, just without saying it outright.

I teased her. "Your loss then tutz. Matty and I are ready to raise hell. Guess I'll just have to take someone else for a ride tonight."

She looked me up and down curiously as Matt chuckled. "Since when are you so confident?" She asked.

Matt jumped in, "our boy here is on the rise Sis. They grow up so fast." He placed his hand over his heart, trying to look proud before chuckling again.

She looked at me questioningly, but kept her thoughts to herself. "Ok then boys. Call me if you need a ride. No drinking and driving Riley."

I nodded. "Wouldn't dare tutz." I smirked at her raised eyebrow as she backed out into the hall.

Two hours later the party was in full swing. I held true to my promise, but amended the rules slightly. I figured a beer an hour would be fine, and I was just cracking my second of the night.

I had been studiously avoiding Brett tonight, and was pretty successful to a point. Matt and him had been arguing in a corner, while the cute hostess cheerleader twirled her hair talking to me.

Bianca, Heather Sinclaire, Heather, and Bianca's cousin Brittany were all having a girls night, but said they might be stopping by. Darcy and Michelle were both working, so Matt and I were pretty much free and clear to see what party life was like without dealing with our ongoing relationships. It was a view of what life had to offer, and I was leaning towards staying single just to keep this momentum going. Matt was being a good boyfriend, spending most of his time talking to dudes and brushing off the occasional interloping female.

I had always admired that about him. He was loyal, and Michelle was lucky in that regard. Most high school guys didn't have that kind of fortitude.

Brett was a clear example of the typical douche. He was flirting and grabbing at anything with two legs and a pussy.

My cheerleader hostess identified herself as Naomi. She had red and black streaks in her blonde hair, a low cut black top, and a black and yellow pleated plaid skirt on. I had just commented on her long French braid as she fiddled with it. "It's fun to play with." She told me.

I smirked at her as I finished my beer. "Looks like it." I replied.

Someone bumped her from behind pushing her up close to me. Her hands landing on my shoulders as she looked over her shoulder. It was clearly an intentional move on the part of her unnamed wingwoman. They giggled and I put my hands on Naomi's hips.

We started dancing right there in the kitchen. Her hands lightly scratching at the back of my neck, while her eyes consumed mine.

Our dance was slow, sensuous. I found myself staring as she nibbled on her lip. Her chest pressed up against mine. I pulled her close. I leaned in and kissed her, following the pressure of her fingers on my neck. It was steady, our tongues intermingling as she sighed into my lips. We continued our dancing, pausing occasionally to kiss, let her hair out, kiss some more, and then we both got a little handsy.

I followed her as she led me away by the hand. I noticed people were watching us, but Naomi ignored them, winding us through the house and up the stairs.

I closed the bedroom door behind us and Naomi forced me against it. Her kiss was hungrier, and my hands landed on her ass under her skirt. I applied pressure to her cheeks, lifting her up and spinning around so her back was flush against the door.

She used the door for leverage as she thrust her hips forward, rotating them. The effect was untenable and my cock raged against my jeans as she forced it to grind into her pussy.

Her lips were sweet, tasting like cherry and her nails scratching at my scalp was driving me wild. I spun again and walked her over to the bed, setting her down gently. Her hands removed her pink panties with a flourish as I undid my belt and lowered my zipper. I was basking in her only a second later watching her hands grab at her loose hair as I thrust inside repeatedly.

As she moaned, her hands slid up the front of my shirt, lifting it before gasping and dropping them. "Oh fuck. Is that-ah. Is that a tattoo?" She panted. In answer, I lifted my shirt over my head. Her nails raked across my torso. "I knew-ah. I knew you were bad. Ah. Oh fuck."

I doubled over her and increased tempo, loving her ever increasing pants as she proceeded to run her hands up and down my back. "Mhmm. Mhmm. Ah. Yes. Mhmm. Oh fuck. Riley. Yes."

My hard-on was unceasing, but I knew I was nearing a massive explosion. My hands lifted her shirt and I captured her nipple with my lips. She moaned as I increased my depth inside of her. Slamming hard while tugging at her nipple, I placed my hand over her mouth to quiet her down.

Subdued, but not silenced, I listened to her muffled "mhmm. Mhmm. Mmmhhmmmmmm." Her walls compressed around me as her lubrication doubled.

I looked into her eyes, just returning from the back of her head. She nodded, so I increased pace and depth duly. My hand released her and she grabbed onto it, pulling it to her chest and interlocking her fingers. Her grip was right as she 'mhmm'd' her way through another orgasm. Feeling her cumming again brought forth the climax I had been avoiding. I groaned and unleashed inside of her.

Her hand held mine firmly and didn't seem to want separation. Our eyes locked as my cock deflated. "Holy fuck Riley. Jesus. That was delicious."

I kissed her lips tenderly. "You're so special Naomi. That was really incredible."Her cheeks flushed in embarrassment and her eyes looked sad. "What's wrong?" I asked.

She pulled herself away and watched me like I was a hunter and she was the prey. I was zipping my jeans when she commented, "nobody's ever said something like that after."

I chuckled. "Yeah well, nobody's ever made me feel like that before either."

She smirked a bit, "you're special too Riley." The hurt look returned. "I know you probably think I'm a slut, but-"

"Don't do that." I replied, shaking my head. "Don't put yourself down like that. I never said you were a slut." A solitary tear fell from her eye down her cheek. I reached over and wiped it away. "I said you were special. I meant that."

Naomi pulled me in for a hug and I could feel she was crying a bit into my chest. I held her even as she started laughing. "What's up?" I asked.

She pulled away to look at me, I took the opportunity to put my henly back on. "You're totally different from every guy I've been with. I mean, you jumped in the sack with me, but that's nothing new. You just like-. I don't know."

I gave her an amused, confused look. "Care to try that again?"

She laughed, finally covering up her expansive chest with her shirt. "Ok so. You've got a tattoo, which is totally cool." I nodded, smiling. "Then there's this." She reached into my lap and kissed me briefly. "There's tons of girls into you, and you're still not like, a total jerk or something because of it."

I pulled her into a hug again. "Thanks." I said. "I never know if I'm doing or saying the right things. I'm still convinced I'm a loser, but I appreciate what you're saying. Guys need a bit of positive reinforcement now and then too."

She nuzzled into my neck. "Keep it up Riley. Don't be breaking hearts, and definitely don't turn doucho on me. Kay?"

"Doucho?" I laughed.

She hit me lightly on my chest. "As much as I like this, we've got to get going. I've got a party to run remember."

I chuckled and pulled her up off the bed as I stood. I kissed her softly and she sighed heavily. "One thing I should tell you." I leaned back to look at her. "I've already got accepted for college in Hawaii. I'm not looking for love right now."

I kissed her hard before pulling her into a hug and whispering into her ear. "Naomi?"

I asked.

"Yeah?" She whispered in return.

I pulled her away and looked into her eyes. "I'm only eighteen dude!" I said much louder.

We both laughed our asses off before heading out the door.

Naomi led me down the stairs by the hand before a friend of her rushed up and dragged her away. I watched as they giggled together and Naomi smacked her friend lightly on the arm.

I turned away and went looking for Matt so we could get out of here, but before I could find him I noticed a silhouette of what looked like Michelle disappearing down the basement stairs. It was odd, since she was supposed to be working, but I followed, figuring that Matt was probably down there as well. It took me a couple minutes to make my way down there as one of my buddies grabbed me to have a beer on the way.

Nothing prepared me for what I found when I entered that room. The lights were all off, and it looked like there was a movie playing, so I figured it was a group that was chilling out. The party hadn't quite died down, but I understood the chill atmosphere was more in line with some people's comfort levels. My eyes hadn't quite adjusted yet.

That's not what I saw however, when my eyes finally did adjust. There was no group, only two people, one guy on the couch, and a girl kneeling between his legs. Her black hair was bobbing up and down as the guy held a fistful. I stood there for a second as my mind took in the scene, then I saw the scrunched up face of the guy getting his 'mind' blown.

The lights turned on suddenly, as I felt a presence at my side. Dreading what was about to happen, I felt the heat radiating off of my best friend Matt, as Michelle lifted her head and saw us. Her face was in anguish, knowing she'd been caught.

Brett sat there, dick hanging out, wearing a triumphant grin.

I had thought previously about this party, and what possibilities it could hold. I had thought that my life, my boring shitty life, was finally getting started. Matt, he looked like his was at an end.