My Boring, Shitty Life Ch. 16

New intro.

Riley is just starting out in life, he's still in high school and starting to find himself. He's prospecting for a motorcycle club, wearing his grandfather's legacy cut, has a dragon tattoo, started building relationships with the women around him, and gotten into a few fights. Things will continue heat up bit by bit and as always, all characters mentioned are over the age of eighteen. This is a work of fiction.

You never know whose path you'll cross in life, and seeing as how tangled up my life has become, I was starting to wonder what the point of it all was. Why are we here? Where are we going? That sort of thing. I had started taking my life into my own hands, but where would that lead? I had no idea. Lucky for me, I didn't have to ruminate on it long.

Hearing the doorbell, I made my way downstairs and opened it up. My neighbor from across the street beamed a heavenly smile at me. "Young man." She greeted, stepping inside without an invitation. She wore a navy blue sundress, and I couldn't see a bra underneath.

"Ms. Duchette." I replied, watching in amusement as she turned around flustered.

"How do you know my name?" She asked warily.

I chuckled, walking passed her and retrieving an envelope before handing it to her in my kitchen. "This was delivered to us yesterday by mistake. I was going to bring it over today, but here you are."

She rolled her eyes. "Ugh. There goes the mystery. What's your name?"

I took her in my arms without warning, kissing her passionately, "wouldn't you like to know?" I asked, thoroughly enjoying flipping the script on her.

She melted into me briefly before shoving me backwards into the counter, clearly trying to reinstate herself as the aggressor. She dropped to her knees, cackling. "No. I. Would. Not."

I was rock hard from then on, as she slammed her mouth onto my shaft repeatedly. She purred, and I gripped her hair roughly before taking over her face fucking. I wasn't going to let her lead this time. Her throat was bottomless, and caressed my cock with saliva and flesh warmly. I pulled her up sharply, without warning, and turned her to face the counter. Lifting her dress, I found that she had forgone panties as well, and she was dripping with excitement.

I wasted no time, forcing myself into her, slamming my hips against her delectable rear end. She coo'd at my brazenness, as I pounded away at her sloppy pussy. "Oh! Yes! Yes! Fuck me! Fuck! Yes!"

I gripped her hair for leverage as I beat her snatch like a madman. She came. Then she came again.

My dick was throbbing as I used my other hand to squeeze her massive tit from behind. I willed myself to hold on just a bit longer as my neighbor's legs shook violently in another orgasm. Former will be damned, I erupted into her unashamedly as I pulled her by the hair and kissed her.

Her back arched as she moaned against my lips. My strength failed me, causing her to plant herself face first on my counter as I drew back.

She stayed in that position as I pulled up my jeans and fastened them. "See you soon Ms Duchette." I told her, walking away from her for once, instead of the other way around. I had no idea how long she took to gather herself.

The following Wednesday, things with Brett and I heated up considerably. I was just coming back from lunch after eating with Darcy, and found him snarling at Matt and leaning over him as Matt was getting something from his locker. I couldn't hear what he was saying, but by Matt's defeated posture and the fact that he wasn't looking at Brett, just staring into his locker, I'd had enough.

I yanked Brett back by the shoulder, garnering the attention of the passerby's. "Leave him alone Brett!" I growled at him.

Brett looked ready to fight, but then switched to his smug smile. "Sure thing Riley. Whatever you say."

Not the response I was expecting, but as I watched him walk off I saw our new principle tapping her expensive high heel with her arms crossed. I shrugged at her and turned to Matt. "You okay buddy?"

He nodded, trying to hide the tears on his face. "You shouldn't provoke him. It'll only make things worse."

I was confused by his response as he shuffled off defeatedly to his next class. I was headed the other way thinking about it when Darcy sent me a video from the rumor mill that had already been taken down. Her recording efforts with the rumor mill was spot on as always.

The video showed Michelle laying on her back naked, with a dick pushing in and out of her pussy. She was clearly loving it.

I thought Brett had been holding a homemade porn over their heads, and maybe that's why Matt was so subdued. That thought went away as I saw another dick slipping into her mouth, and heard Brett's voice laughing about what a slut she was. Brett was clearly holding the camera, and it tilted up to show Martin as the other guy. The camera angle panned over what must've been the inside of a hotel room, to show Matt sitting on a nearby chair in tears. His hands were duct taped to it, and that's all I could make out before the video cut off.

Darcy texted one word to punctuate exactly how I was feeling. 'DUDE!'

After that, the cat was out of the bag. Michelle openly flirted with guys on all sides, while Matt retreated into hisself. I followed him home, but he refused to talk to me. His sister Kelsey met me in the driveway to get up to speed. She cried in my arms afterwards while I held her.

The worst part for me was Bianca. She looked like nothing had happened. She ignored Michelle and Brett's open flirtations, and kept up her own with me. I cringed every time I looked at her. I know she liked drama, but this was all a bit too much.

School was like a war zone, I couldn't walk the halls without getting shoulder checked by Brett or one of his posse. I grit my teeth and tried to bear with it all. Rhett didn't want me going off in the hallways, and emphasized that he wanted me to finish school without any more incidents.

By Friday, I had had enough, and was ready to fight the next person who so much as looked at me the wrong way. My adrenaline was spiked, so I knew it was only a matter of time.

I knew going to the party everyone was talking about was simply out of the question, but Naomi quickly alleviated my doubts after inviting me out. "Ew! No. Not that party. My place. I'm not talking about Hank's thing."

I shrugged. "Alright I guess. Long as Brett won't be there."

She nodded, grinning brightly. "He won't. It's invite only." She gave me a parting kiss. "See you at nine!"

I watched her skirt swaying as she danced away to go cheer for tonight's game.

I got to the party later than I intended, as Trash had me washing Tess' mustang last minute. She and Brittany giggled together watching me, but otherwise didn't give me the time of day.

Naomi opened the door a crack before seeing me and ushering me inside. I checked her out as she walked off down the hall in high heels and a silk robe calling out, "ladies! Look who's here!" I followed her into her living room and gawked at the scene before me. "It's a lingerie party!" Naomi giggled.

My heart hammered in my chest as I counted five nearly nude cheerleaders all looking at me. I didn't know how to stop my eyes from swiveling from one girl to the next. They were all dolled up and sitting in a circle drinking out of red party cups. Tits! Ten Tits! Ten perfect, barely legal, cheerleader tits!

The girls had saved a seat for me in their circle on the living room floor. Naomi introduced me, though I already knew most of them. "You already know Irene," she giggled, "this is Becca, Savanna, and Ally. Guys this is Riley."

I waved dumbly, before grabbing a cup from Becca and letting the fruity beverage quench my thirst. I could taste the alcohol in the mix, but it was a sweet and downplayed concoction. "It's really good." I told them.

"It's strong too." Ally informed me.

"So what's the plan then?" I asked, trying to keep from seeming too eager.

"We're playing truth, dare, or drink!" Becca told me excitedly.

I smiled. This was going to be fun. "Ok. New round? Who's first?"

Savanna spoke up, "well, you! Truth or dare Riley?"

"Truth."

She conferred with Ally while I watched her abs twist in her black lingerie. "Who are you dating right now?"

I chuckled. "That's easy. Nobody. Ally, truth or dare?"

"Truth."

"Who here is dating someone?"

She paused, looking over at Irene. "Uhm."

I took a nearby pillow and chucked it at Irene. "Hey! What the hell?!" She asked.

I shook my head at her. "You're at a lingerie party without your guy?! With just me here? Come on, what gives?"

Ally came to help me out, "truth or dare Irene?"

She rolled her eyes. "Ugh. Truth."

"What he said. What gives?"

Irene took a sip of her drink before she responded. "It's not like I don't want him here. Naomi had this idea that it would be fun if it was just the girls and Riley."

I raised an eyebrow in Naomi's direction as she shrugged.

Irene kept the game going. "Truth or dare Savanna?"

I watched as the tension built, Savanna was thinking it over. "Da-Truth! Truth."

"How long have you and Ally been fooling around?" She asked.

My eyes went wide as the two cheerleaders blushed. They looked like they were conferring silently. "Uh. About six months." She shrugged, my pants were feeling tight all of the sudden. "Riley. Truth or dare?"

"Truth."

She and Ally whispered together then Savanna asked, "does it bother you that Irene has a boyfriend and if so, why?"

I gave Irene a look that told her as much. "Yeah. It does."

"How come?" Savanna prodded.

I shrugged. "Well, I'm not one for labels, but if you're going to use them, they should mean something. If I was DATING someone, I'd want to know if this was her idea of fun with friends."

"EVERYBODY DRINK!" Naomi yelped.

I listened, but had to ask, "why?"

Becca elbowed me. "She does that when she thinks things are getting awkward. It's a house rule."

I chuckled. "Ok. Irene, truth or dare?"

Irene finished her drink and answered while pouring a new one. "Truth." Becca elbowed her. "Alright! Dare. Jeez."

I grinned. "Give me your phone and unlock it."

"Ooooh!" The girls all giggled.

Irene was hesitant but did as she was dared. I took the phone and saw her most recent messages were to a guy named Patrick. She referred to him as Baby. "This him?" I asked, showing her her phone.

Irene nodded, and Naomi chuckled into her drink as I called him up.

He answered on the second ring. "Hey Babe! What's up?"

"Hey man, don't freak out. My name is Riley and I'm at a party with the cheerleaders."

"Yeah? Why do you have Irene's phone?"

"Well, I'm the only dude here, and I found out you're dating Irene here. So I figured one more rooster in the nest would probably be alright."

He stayed silent for a minute. "Did she say she wanted me there? This thing is sorta new. I don't want her to think I don't trust her."

"Listen dude, I get that. But she wants you here, the party was invite only, so she felt bad but didn't tell you. I'm inviting you so it's cool now. I just don't think it's fair to you to miss out, especially since you guys are still new. Ya gotta talk to make it work, ya know?"

I handed the phone over to Irene so she could close the loop and we started another round without her as she did so.

"Keep things tame until he gets here." I told the girls. "It's only fair."

Things were all PG-13 for the next twenty minutes or so until Patrick got there. I smirked at his wide eyed look when he came in. I had probably looked the same.

"Alright Pat! You're up!" I told him, shaking his hand. "We've been keeping things civil waiting for you. Truth or dare?"

Patrick downed a drink. "Dare! Definitely."

"I dare you to make out with Irene."

He chuckled and didn't hesitate while we cheered them on. "Naomi, truth or dare?"

"Dare..."

"I dare you to play duck duck goose!" He told her, making us all laugh.

Naomi went around the circle, touching the tops of everyone's heads and chanting duck, before reaching down and copping a feel on Savanna's breast. "Goose!" She yelled, hurrying over to her spot while Savanna chased her. Seeing them jostling around in their lingerie had me stiff, and I'm sure Patrick was feeling the same way. Naomi took her seat, "Ally, truth or dare?"

"Truth."

"How many people in this circle have you gone down on?" Naomi asked.

Ally went beet red, before shaking her head and taking a drink rather than answer the question. Savanna nudged her arm playfully. "Hussie!"

I looked around to see everyone smirking their own sly smiles. "Riley, truth or dare?"

"Truth." I replied.

"How many girls have you slept with?" Ally asked me.

I shook my head and took a drink. "I'm not saying."

"Dude! Are you a virgin?" Pat asked me incredulously.

"No." Naomi and I answered at once, causing a chorus of 'ooohs' from the gathered party.

"Becca, truth or dare?" I asked.

"Truth."

"If you could have anyone, who would you want to sleep with?"

She blushed slightly, "uhm. Is it too late to change my answer?" Our boos told her it was. "Fine. Uh. Well overall? Ryan Reynolds."

"And in this room?" I prodded.

"Uh uh." She shook her head. "That's two questions. Irene, truth or dare?"

This is the point in the night where everything turned. "Dare!" Irene challenged.

"I dare you to make out with any person here of your choosing, other than Patrick."

We all looked his way to see him nodding excitedly. "Go on babe! Do it!"

"Oh I will! But in the meantime, your dare is to take your dick out and stroke it while I do."

Holy shit! I thought.

Irene didn't wait for him to comply as she crawled over to Ally and pulled her in for a kiss. I watched as the two of them moved their tongues together. Irene's ass swaying in my direction.

"Riley! I dare you to play with Naomi's pussy. Get her off before Irene and Ally are finished." Pat barked, dick in his hand.

Doing as I was dared, I stimulated Naomi's clit and whispered in her ear. "I want to fuck you so bad right now."

"Oh fuck!" She squeaked.

As I got her going, her hand shot out to grasp my cock in my jeans. Everyone in the circle was flush with arousal, as we all participated in our own way. Irene stopped kissing Ally, and switched over to Savanna while looking at her boyfriend out of the corner of her eye. Becca was watching Pat as he stroked his erection while Ally's hand crept over Naomi's thigh, joining mine and really getting her worked up. I sucked on Naomi's ear, causing her mouth to open in a gasp. Ally took the opportunity to stick her tongue in and start making out with Naomi.

"Oh fuck!" Patrick exclaimed. I looked over to see Becca's head bobbing up and down in his lap.

"Hey!" Irene yelped. Pushing the girl aside and taking her place. "That's mine!"

Patrick leaned back and watched as his girlfriend did her damndest to suck his soul out of his body.

"Cu-Cumming!" Naomi gasped, relinquishing my jean clad cock.

I stopped what I was doing to let Ally finish her off, opting to sit on the couch and pull my pants down. Becca saw me and crawled over, dragging Savanna's hand from her pussy and pulling her over to me.

The two of them crawled up onto the couch in a kneeling position to stroke my cock together and press into my face with their lingerie clad breasts. My hands ran down their backs to cup their asses in my grasp while my lips worked back and forth sucking skin and silk.

Naomi joined us, facing away from me, and replacing their hands with her hot pussy. We locked eyes over her shoulder as she quivered and rolled her hips. I felt a tongue lapping at our joined lower half, and lips sucking on my balls. I wouldn't last long, but I held out longer than Naomi did. Her thighs clenched Ally's head as she moaned out in orgasm.

Becca gently pushed her aside, straddling me, and giving me no rest. Her depths welcomed me as she pulled Savanna in for a kiss. I watched their tongues intertwining as I fought off my orgasm.

Naomi and Ally had fallen to the floor in their excitement, and were grinding their pussies together while they kissed. Irene sat astride Patrick on the floor, riding him to the gates of heaven.

When Becca came, I nearly did too, but Savanna playfully shoved her away before sticking my cock into her throat. My hand hadn't left her ass. Becca cuddled into my side watching her friend blow me softly. She was clearly trying to keep me on edge but not allowing me to go over.

My orgasm sufficiently staved off, Savanna straddled me herself and lodged me deep inside of her. She remained motionless, except to thrash her hand along her clit aggressively while looking into my eyes.

Her brow furrowed as a massive wave hit her. I bucked my hips, pounding into her from below as she came atop of me. "Dare you to cum inside of her." Becca whispered.

Savanna nodded encouragingly at me and I couldn't hold out any more. My erection was strong, but the churning need to cum was just too much. I allowed myself to finally let go as Becca kissed my neck. Feeling my hands pulling her close, Savanna leaned in and started kissing me as I emptied myself into her voraciously.

The room grew quiet. A few of us nodded off as we recuperated and I awoke to the door slamming as Irene and Patrick failed in their sneak out attempt. I quietly extricated myself so as not to wake the sleeping cheerleaders.

Naomi pressed her lips on mine as she showed me to the door. "See you next time." She whispered quietly.

I kissed her excitedly before making my exit. "You're on!" I told her, all the while thinking that my life, my boring shitty life, was finally getting started.