A Night in Montana – Anal – Free Sex Story

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“Seriously, man? This sucks,” I groan as my buddy Kyle pulls up to my ex-girlfriend Belle’s house. Every year since we were 15 Belle has a massive house party for her birthday, and her 21st birthday was no different and definitely the biggest one yet. Belle and I broke up three months ago after four years of a toxic relationship. I couldn’t do it anymore, couldn’t handle her rage fits of jealousy when she saw me talk to another girl, her crazy mind games with me. It wasn’t worth it anymore, and I’m pretty sure she was fucking her professor on the side.

“Dude, she’s going to be so black out she won’t even notice you. Just get drunk and avoid her.”

“Whatever,” I roll my eyes as I slide out of the passenger seat and head up to driveway to Belle’s parents 8,600 square foot mansion I’ve spent so much time in. I can hear music pumping through loud speakers from inside the house and wrapping to the back yard. Groups of people stand around the front of the house smoking joints and cigarettes, the smell of smoke permeating the air. I suck a breath in and push past them into the open front door to sweaty bodies wall to wall. With Kyle behind me, we push to the massive kitchen that’s stocked with about a hundred bottle of liquor and various mixers all around. I instantly grab some whiskey and fill a good third of a SOLO cup up with it, splashing some Coke in afterwards.

“Hey, Auggie,” I hear a sultry voice behind me. I whip around to see a platinum blonde I hooked up with a while ago standing in front of me and I cannot remember her name for the life of me.

Maddy?

Marcie?

Maybe Jessica?

“How’s it going?” I lean down and kiss her cheek, feeling eyes from all around looking at me, probably wondering what I’m doing at my ex’s party.

“It’s going pretty good. It’s been a while,” she smiles at me, taking a sip of the clear bubbly drink in her cup.

“It has,” I tell her, leaning into her ear, “I’ll catch you later,” I say and slink off away from her, not caring for any small talk at the moment.

I’m annoyed, I’m irritated and I’m pissed off that Kyle didn’t tell me this is where we were heading. I take a large swig of my drink as I walk down the hallway into the massive foyer that wraps around to the open living room. I spot a few girls looking at me, huddled together and shoot them a wink and smile. I take another long sip of my drink and scan the crowd for someone I know. Anyone to distract me right now since Kyle already found a piece of Ass he’s most likely taking home. And tonight, I don’t care about getting my dick sucked or getting laid, as long as I make it out of here without a scene.

I feel a hand smack my shoulder and I turn around to see my very drunk friend, Miles, sway back and forth with a Corona in his hand.

“You’re the last person I expected to see here,” he slurs, shouting over a remixed version of Post Malone’s Rockstar.

“Yeah, dude, me too,” I yell back, pouring more of my drink down my throat.

“Have you seen Belle?”

“No.”

Miles laughs, shaking his head and then tells me he’s been eyeing this black haired girl in the corner and to wish him luck. Pursing my lips, I lift the cup to cheers him and watch him slink towards her. Feeling a buzz, I push further into the crowd where I say what’s up to a few other girls who catch my arm, begging me stay and dance with them. I hear Belle’s drunken laugh coming from above me at the mezzanine and I glance up to see her talking to some total toolbag who looks like his name would be Tyson. I feel suffocated and need to top my drink off so I push back into the kitchen where I just exchange my SOLO cup for the whole bottle of Jack Daniels and slip down a dark hallway I know connects to the glass conservatory.

Walking into the dark greenhouse, I walk past all the plants and bookshelves Belle’s mother treats like children and out into the empty backyard. I take a sharp inhale of the fresh air and bring the bottle up to my lips as the motion sensor lights turn on to reveal a tiny blonde sitting with her back to me. Her open back top reveals her smooth, tan back with loose curls falling against it. I take a swig from the bottle and take a step forward, just as she turns towards me, noticing the light turn on. Her familiar face smiles at me, as she wipes a small tear off her cheek.

Belle’s best friend, Montana, sniffles before saying, “Hey August.”

“What are you doing out here?”

“Just getting some air,” she sighs, turning back around.

“What’s wrong?”

“I didn’t expect you to be here.”

“Yeah, you’re fucking telling me,” I roll my eyes, “What’s wrong?”

“Nothing. Belle can just be so fucking mean,” Montana sniffles again. I pull a cigarette out with my Free hand and then light it, exhaling the first breath of smoke.

“That’s for damn sure,” I tell her, walking over to sit on the outdoor daybed across from Montana. Taking another drag of my cigarette, I hold the bottle out to Montana who takes it from me and takes 3 small pulls, crinkling her face after every one. I look at Montana’s thin fingers wrap around the neck of the bottle and for a split second I imagine her fingers curled around my dick like that.

I shift in my seat a tiny bit, watching her set the bottle down between us. Montana has always been a fucking babe and I’ve definitely had thoughts about fucking her, but it’s been impossible with Belle as her best friend. I shake my head, trying to get those thoughts out of my head as Montana sighs again. I take another drag of my cigarette and then hold it out for her as well.

“So, what are you doing here? Isn’t this weird?” Montana reaches up and takes the cigarette between two fingers, bringing it up to her lips as she purses them around the filter and breathes in.

“I have no idea. Kyle brought me here and didn’t tell me where we were going before I got into his car,” I roll my eyes, grabbing the bottle.

“Are you going to leave?” She asks, taking another drag of my cigarette.

“Maybe.”

“Well, I hope you have a good night if you do,” Montana exhales loudly, looking down at her black wedges that make her toned legs look so fucking sexy. I can see straight down her low-cut shirt into her cleavage with her leaning over like this to talk to me. I take another pull out of the bottle to distract myself.

“Maybe I’ll stay and talk to you a little longer. Try and cheer you up,” I shrug.

Montana gives me a soft smile as she crosses her fit legs and tugs at her white pleated mini skirt. The motion sensing light turns off, leaving us in the dark except for the glow from the lights on in the house. I like it better this way.

“I’d like that,” she says softly, passing my cigarette back. I tap the ash off of it and ask her if she’s still seeing this guy, Xander, I saw her hanging around a bunch when Belle and I were together, “No, not anymore. He was fucking like 4 other girls behind my back so I told him to get lost a few weeks ago.”

“Shit, sorry to hear that,” I murmur, rolling the cigarette between my fingers before I take another drag. I hand the bottle to Montana again who takes a swig from the bottle, shaking her head.

“That’s okay. It wasn’t serious or anything, but that’s just skeazy,” she says. I say nothing and finish off my cigarette before ashing it out and walking it over to a small trash can around the side of the daybed before I go and sit back down across from Montana.

Maybe it’s the whiskey, or being single but I don’t remember Montana ever being this Hot. Thoughts of her pouty lips around my dick invade my head. I try to blink them out but feel my dick starting to get hard in my pants.

“Come here,” I finally say, patting the spot next to me, “That way we can share this bottle easier.” She gets up and comes to sit right next to me with the bottle in her hand, extending her legs straight in front of her. Montana brings the bottle up to her lips and sways a little bit, the whiskey finally starting to hit her a little harder. She twists and sways her feet back and forth, in tune with the music from inside trailing faintly outside.

“Truth or dare?” she finally asks, setting the bottle in my lap. I chuckle and think for a moment, not even remembering the last time I played this game.

“Truth,” I say, taking a drink.

“Are you sad about Belle?”

“Not really. It was over a long Ass time ago, we only stayed together for the comfort.”

“I thought so,” Montana sighs, and then shifts to lay down on her back, looking up through the open canopy of the bed.

“Truth or dare?” I ask.

“Truth,” she smiles.

“Are you and Belle really best friends?”

“What?” Montana snaps her head at me before sitting up carefully, “Of course we are, why would you say that?”

“Well she treats you like shit, and I know for a fact one of those girls Xander was fucking was Belle. Just seems weird you’d still call her your best friend,” I shrug, taking another pull from the bottle without looking at her. Montana’s mouth opens like she’s about to say something and then she snaps it shut.

“It’s complicated,” she says softly after a few seconds, dropping her head to look at her knees.

“Yeah, it always is with you guys.”

“We’ve just been friends for so long. I can’t stand up to her, you know how she is,” Montana says quietly again without raising her eyes. I roll my eyes and hand her the bottle.

“So you’re just going to let Belle Van der Waal walk over you for the rest of your life?” I snap at her, surprising myself with the edge in my voice. Montana stays silent as she drinks from the bottle. Montana sniffles again and keeps her head down. I suddenly feel bad, so I place my hand on her bare thigh just below the hem of her skirt and use my other hand to lift her face to mine.

“I’m sorry, all right? That was mean as fuck,” I sigh. Montana taps on the neck of the bottle, sniffing again.

“Did Xander really fuck Belle?” She asks me quietly and now I feel like a real grade A asshole. I just nod my head, dropping the hand I had on her face and watch her take another huge pull from the bottle, “That’s fucked up.”

She raises her head to look at me, her gray eyes shimmering from either tears or being slightly drunk. She pauses for a second before letting out a sharp laugh, tossing her head back.

“Truth or fucking dare, August?”

I give her leg a squeeze, “Dare,” I grin at her. Montana sets the bottle down on the concrete between us and taps a finger on her chin, staring into the distance like she’s thinking hard.

“I dare you… to give me goosebumps,” she finally says, lowering her voice and raising an eyebrow at me.

I laugh under my breath and push my hand even higher up her thigh until my fingers run along the edge of her underwear near her vulva and lean over close to her ear.

“That’s too easy, Montana,” I breathe against her lobe before kissing behind her ear as my fingers run down to the inside of her thigh, inches from her lace covered Pussy. Montana gasps sharply and yanks away from me, eyes wide. She rubs her arms and giggles nervously, hiding the shivers on her arms. I pull my hand out from under her skirt and lean back, chuckling. I run my hands down my face, feeling my hard on stretch under my pants, heat rising through my lower stomach. I exhale and quickly glance at the mother in law pool house across the property. Montana shakes her body out and reaches down for the bottle quickly, taking a long drink before passing it over to me. I set the bottle down on my hard on, trying to shift it in my pants a little. My heart pumps hard against my chest as I swig from the bottle, a million things pounding through my head.

“Okay, well. Your turn,” Montana finally giggles again. She pulls her extended legs in and leans back on her arms in the day bed. I turn my head to look at her, outstretched with her top sliding up a little to show her flat stomach.

“I dare you to go to the pool house with me,” I say. Montana’s eyes go wide again before a smile starts pulling at her lips, “Can you keep a secret?”

“Yes,” she whispers. I climb onto the daybed and crawl off the opposite side of it, taking Montana’s hand with me so we don’t set the motion light off again.

I tell her to take her shoes off and then we quickly run to the French doors of the pool house. I reach to the top of the frame and pull out the small key I remember Belle using when we used to fuck in here and open the door, ushering Montana in before me as I shut the door behind us. Montana drops her shoes down by the front door and turns on the standing light by the door before turning to me.

“Wanna go to the bathroom?” I jerk my head towards the bathroom in the corner, stepping closer and towering over her.

Montana keeps her eyes on me, looking up as she nods. She grabs my hand and pulls me into the bathroom, flipping the lights on. I shut and lock the door behind us, watching her turn around to face me. She licks her lips as I take a step toward her, a teasing smile crossing my lips. Montana raises an eyebrow at me, flipping her eyes to look at the zipper in my pants before back up to me. I roughly snake my around her waist and pull her closer to my body, feeling how warm she is. My dick pulses in my boxers and I feel a pull in stomach. I’m so fucking Horny and she is so fucking Hot. Montana’s hand reaches out and drags down my chest, leaving a trail of fire down my abs.

“Promise not to tell anyone?” I groan, closing my eyes for a split moment. I dig my fingers into her side, waiting for her answer.

“Yes,” she breathes before standing up on her tip toes and slamming her mouth against mine.

My other hand grabs around the back of her neck and I pull her closer, moving my lips against hers. Montana moans on my lips and works both her hands underneath my shirt and up my sides. I inhale sharply and then drop my hands to her tight Ass, lifting her up to place her on the countertop. My lips don’t leave hers as I slip my hand into her hair and get a fistful of it, using my other one to massage her tits. Montana flicks my lip with her tongue and uses it to slip into my mouth, ushering me to do the same. She runs her fingernails down my back and I push my hand up her skirt to the very top of her thigh where her panties are. She sighs and uses her teeth to pull at my lip. I pull away from her and give her upper thigh a hard squeeze and use my other hand to yank her head backwards so she looks directly up at me. Montana digs her nails into my back gently, rolling her hips towards me. I rub the inside of her thigh with my thumb, making eye contact, my eyes hard.

“Are you going to do everything I fucking say?” I ask her, my voice low and stern. I release the tension on her head to let her nod.

“Yes,” she breathes, flicking her eyes down to my lips.

“Good,” I snap at her and reach in to kiss her again.

The warmth in my lower abdomen starts creeping its way higher up my stomach, my dick throbbing so hard against my pants. Montana sucks on my lip and then pulls away to kiss my chest and run her hands to the front of me and pulls my shirt up and over my head. She kisses my jaw and trails down to my neck with her lips and I drop my hand from her hair. Montana moans against my neck as I run my newly Free hand under her skirt and grip the sides of her panties, yanking them down her legs aggressively. She watches the Hot pink lace drops to the ground and slowly lifts her head back up to me. I yank her body closer to mine so her naked Pussy‘s right against the bulge in my pants under her skirt. I growl against the top of her head and push her harder into me, feeling her roll her hips against my dick gently. Montana gasps sharply and I feel her fingers edging the top of my pants.

“Get on your knees,” I command her, pulling her off the counter.

Montana slips off easily and drops down to the white rug in front of me, looking up at me with her huge eyes. I use a hand to rub the top of her head right as she reaches forward and undoes my pants, pulls the zipper down and works my pants and boxers down just until my cock pops out right to her nose. She gasps sharply and then smiles up at me, reaching to take my base in her hand. And like deja-vu, Montana wraps her pouty pink lips around my dick, swirling her tongue around the head. A deep exhale escapes from my chest and I run a hand down my face, shivers going down my body.

“Ohh fuck,” I groan quietly, reaching both my hands forward, placing them on the back of her head. Montana uses her right hand to work the bottom half of my dick as her mouth works the top, my hands guiding her. Her other hand wraps around my thigh, holding her drunken self steady. I watch her tiny face go back and forth on on me, coating me with her sweet, sticky saliva. I push her head a little further, aching to feel the back of her throat. I moan as she takes me in her mouth and squeeze a handful of her hair, pulling her back and forth a little further. Montana lets a small moan escape from her nose and within two minute I have the whole length of my cock in her throat, her nose tapping my pelvis with every thrust.

“Fuck, Montana,” I grumble and feel Montana struggle, starting to pull back so I push her into me a little bit more for a second and then let her up for air. I hold her head steady, a fistful of hair in my right hand as she inhales several times for air, and then grins up at me, using the back of her hand to wipe her mouth as my dick hangs right by her face, “Get up,” I say, pulling her up.

Montana climbs back up to her bare feet and I push her back up against the counter, moving my hand from her hair to the back of her neck. I use my Free hand to push between her thighs and circle her clit, my dick pressing between our bodies. She sighs, rolling her eyes to the back of her head. She reaches up under my arm and squeezes my shoulder, holding tightly onto me. I lean down and start kissing her neck teasingly, sliding two fingers up and down her dripping wet slit.

“You’re so fucking wet,” I snicker in her ear, massaging the other side of her neck with my fingers, “You just can’t hold back, huh?”

“Auggie…” she whispers, her eyes still closed. She reaches and strokes my dick softly as I suck on her neck, teasing her clit with my fingers again.

BANG! BANG! BANG!

Both our heads slam towards the locked bathroom door, eyes wide. Montana turns back to me quickly, her eyes filled with panic, going back and forth.

“Auggie, fuck, fuck,” she says as quiet as possible, nearly mouthing the words. I slam my hand over her mouth and bring my other one with a finger up to my lips shushing her.

“DUDE, AUGUST, ARE YOU IN THERE?” I hear Kyle’s voice shout from the other side of the door. I sigh with relief and rolls my eyes, “DUDE!”

“Fuck off man, I’ll be out in a little.”

“What are you doing?!” Kyle yells and I can tell he’s pretty drunk.

“I’m in the bathroom, Kyle, fuck off!” I yell back, my eyes staying on Montana. She keeps shifting her eyes back and forth on mine, eyebrows furrowed together in worry. I work the hand that’s not on her mouth back between her thighs, and against her slit again. She tries shaking her head but I push a finger into her tight little Pussy as I nod my head.

“C’mon August, let’s go get drunk!”

“Kyle I’ll be out in a fucking little bit, god damn!” I shout, plunging my finger deeper into her. Montana sighs softly into my hand, relaxing against my body. The other side of the door is silent for a few seconds and I think we’re in the clear before Kyle speaks up again.

“All right, man, I’ll see you soon. Just make sure Montana puts her shoes back on when you’re done with her in there,” He laughs and his footsteps fall away before the light coming in from under the door crack shuts off and the front doors slam behind him.

Montana’s wide eyes scream worry as I take my hand off her mouth and put it on the edge of the counter right behind her, fingering her slowly. She reaches down and stops my hand gently.

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