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Jackson Hole Resort

"Three friends indulge in a fantasy during Christmas vacation..."

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Competition Entry: Winter Break
There’s nothing quite like looking out the window – first thing in the morning – and seeing a blanket of fresh snow that dumped during the night. This definitely could be a ‘fuck my life’ moment if you hate winter and the snow that accompanies it. And, for Cale, it definitely was, but it was also a nice reminder about his upcoming skiing trip with a group of friends to Jackson Hole Resort in Jackson Hole, Wyoming.

The four of them – Rachel, Kelsey, Cale and Brian – had planned the trip for Christmas Break a few months back as a way to escape the bland Oklahoma winter. Not that the winter is good or anything, but outside from the annual ice storm, there’s not much action regarding snow. They wanted to go to a place where snow lasted more than a few days.

The four friends attend Oklahoma State University and have been close friends since they were in high school. None of them have ever dated, but each guy has slept with each girl – and that was a result of shitty dates or a horrible hook up. They’ve been able to confide in each other about everything and that’s what made their bond so strong.

“How many guys do you plan on fucking while we’re in Wyoming?” Cale asked Rachel about two hours into the sixteen hour drive to Jackson Hole.

“Depends how hot the guys are. I know, at the very least, I’ll be fucking two guys,” she replied with a wink, all four of them knowing exactly what she meant.

“Me too,” Kelsey chimed in as she looked to Rachel. They shared a devious smile, both knowing they were going to fuck Cale and Brian regardless of their own sexual endeavors.

***

“Wow, this is a really nice cabin…” Kelsey said, yawning as they pulled into the driveway of the cabin they’re lodging in for the week.

“Yeah, my dad got a really good deal for us. Apparently he grew up with the guy who owns this place,” Cale said before they got out of the car.

Cale’s dad happened to be really good friends with David Fjestad, owner of the Jackson Hole Resort. They were staying there for next to nothing.

“That’s pretty cool…” Kelsey said before giving Cale a quick once over and heading inside the cabin with her bags.

The four of them quickly settled into the cabin as each one took claim to the room they were sleeping in. Cale took the master bedroom which happened to be located downstairs between the kitchen and living room. Brian took one of the two rooms upstairs, while Kelsey opted for the room next to Cale and Rachel claimed the room next to Brian.

The first night

Everyone was unpacked, the refrigerator stocked full of alcohol and food they’d need to have to survive the week, the hot tub primed and ready for some serious action. And once everyone was ready, the drinks began to pour and the hot tub gradually began losing water.

It’s truly a weird concept that people get stupid and careless when they drink. And, for some strange reason, the four college students seemed to fit that persona. The more drinks that were consumed, the more messy they became. One smartass comment and the water began to fly. By this time, everyone was well buzzed enough to not care that water just ruined their drinks.

The guys, at this point, were well beyond self restraint as they unabashedly checked out their friends. The two girls were actually reveling in it, wanting it to continue, or maybe more. Maybe, just maybe, the girls wanted them that night. Kelsey made it obvious she wanted Cale to fuck her to oblivion, but was she really going to lay it out on the line for everyone to see? Why not? It’s not like they haven’t had sex because the other one couldn’t find a substantial date or fuck partner when the other one was available. What would it hurt? After all, they would be doing each other a favor the first night.

***

Are you fucking kidding me? Cale thought as he awoke to the sounds of a girl being royally fucked.

He listened in a little closer and heard the familiar sounds of Rachel’s moans. From the sounds of it, Brian was shafting her hard and deep.

Good for you, buddy…

But this gave him an idea. He reached for his phone and quickly sent a text to Kelsey.

You awake?

He only had to wait about a minute before his phone buzzed, signaling he received a message. He quickly opened it to read her reply.

Yeah, kinda hard to sleep through her loud moans. But you should get your ass over here, I wanna see who can be louder…

Cale quickly jumped out of bed before making his way to Kelsey’s room. His dick was at full mast by the time he reached her bed. He didn’t waste any time. He quickly stripped down before sliding into bed with Kelsey.

“That bitch made me so fucking wet…” she said before shifting underneath Cale as he pulled back the blankets. She grabbed a hold of his cock and began furiously pumping it in her small hand. “Already hard and ready to go for me, mmmm…”

“Damn right I am. I can’t believe she woke me up. But I’m sure you would’ve had she not…fuckkkk…” he moaned out as the head of his cock met the opening of her very wet cunt. He easily slid inside her and wasted no time in fucking her as hard as he could.

“OOOHHHH, Fuck yes!” She screamed out as he drove hard and deep inside her, stretching out her walls with every forceful thrust. She was determined to be louder than her best friend upstairs.

***

“Do you hear that?” Rachel asked, breaking her concentration as she heard the impenetrable scream from Kelsey.

“Sounds like you have some competition now,” Brian said with a wink before almost fully withdrawing his cock and slamming back inside her pussy, her ass shaking with the violent thrust as he took her from behind with her on all fours.

“Oh, fuck! Fuck me harder, Brian! Make me SCREAM!” She let out a loud scream before her hand dove to her aching clit, furiously rubbing it as she was rocked by an incredible orgasm.

From there, the fight was on to see who could be loudest that night. Kelsey happened to prevail, but only because Brian came a little sooner than he had planned to.

Two nights later

The second day of the trip was primarily used for recovering from the night before. However, sex had somehow managed to slip its way inside the daily routine – not that any of them were objective to it or anything. Kelsey quickly claimed Cale and they ended up spending most of the day in her bed as they quickly discovered each others’ needs and tendencies.

Brian and Rachel were a little more casual about things, but another couple rounds of sex did take place when Brian walked in to the bathroom while Rachel was showering. He thought it would be funny to sneak in the shower with her and scare her. All that did was cause flying fists and then their wet, naked bodies to come into close contact. In turn, that led to a lot of fondling, which led to hot sex with her wrapped around him as he sawed in and out of her before he deposited his cum inside his friend.

That night was fairly quiet – movies and cuddling was pretty much the highlight of the night before everyone went to their respective rooms for much needed sleep.

Cale enjoyed the sex with Kelsey, but he also wanted to fuck a girl he’d never see again. Besides, he and Brian had plans of tag teaming a girl while Kelsey and Rachel were fucked by random guys. And for the guys’ plan to work properly, they needed to make sure they were able to convince a girl to fuck them both, and they need to make sure they found at least two guys to keep Rachel and Kelsey occupied while they made a total slut out of a random girl.

The easy part would be finding two willing guys to fuck their friends. The challenge, however, would be finding a girl with the deep, insatiable fantasy of being taken by two or more guys at the same time. One of two things could happen – Cale could find the girl, talk her into coming home with him, and then talk her into having Brian join as well. Or they both could just talk the damn girl into fucking them both so she knows – and is fully aware – of what’s to come for the night.

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Of course this all easier said than done.

***

The four friends made it back to the cabin shortly after 2am with Cale holding an ice pack against his left eye.

“I can’t believe he hit you,” Kelsey said, holding onto him as they sat on the couch.

“He should’ve left you alone the first time he was told to do so,” he said, removing the ice pack and inspecting the place where Justin had punched him. “That damn prick…”

Brian and Cale approached Kelsey just a minute after Justin came back with her drink. Justin thought he was going to be the one to bed Kelsey that night. Little did he know, Cale had already placed his claim on her. Words were exchanged and next thing anyone knew, Cale was struck in the face. Brian pulled Justin away and struck him before Justin hit a table and then was escorted out by a bouncer. The bartender gave Cale an ice pack before they left.

“Oh well, but thanks for saving me from him. I really had no interest in fucking that douche…” she said as she hugged him before kissing him on the cheek.

“Any time, babe…so were you planning on fucking anyone at all tonight?”

“Uh, I was hoping too, but that may not happen now.”

“Why not?” He asked as he turned to face her.

“Well,” she began as she turned her face from his gaze, “I wanted to try something I’ve never done before, but I’m not sure if that’s going to be possible…even though I heard…that…ah, gosh!” Her face turned bright red as she struggled to find the courage to spit out her fantasy.

“What?” His face breaking into a smile.

“Well…one of the girls you were trying to hit on came up to me and said you and Brian were trying to get her to come back her with you guys and have a threesome…I, um, well…kinda told her that she should do it or I would…” her face turning an even deeper shade of crimson, “she told me to go for it…”

Cale’s face lit up. He wanted her if all else failed, but wasn’t sure if she’d be willing to take on both of them. If it wasn’t going to be her, then they’d make their attempt on Rachel. And if that failed, well, they were completely fucked as far as their plan was concerned.

“Do you want to?”

She turned to face him and with a coy smile, she replied, “I most certainly do.”

“Good…” he smiled before pulling her into him for a deep kiss, his hands roaming her slender body. “Let’s go get Brian and make this happen,” he said, sporting his hard on and taking her by the hand as they found Brian and Rachel in the kitchen.

“You might wanna put your hard on away…” Brian said as they entered the kitchen.

“You still down to double team a girl tonight?” He beamed at his best friend.

“Ummm, who?”

“Kelsey…she said she wants us to fuck her.”

“No shit?” He looked Kelsey up and down. “You really want that?”

“Yes, I really do!” Kelsey’s shyness completely went out the window. “Do you want to join in, Rach?”

“Nah, I’m good…not really my thing, but I’ll definitely watch!” Rachel said, her face turning red as well.

“Let’s do this then!”

They wasted no time on getting things started. Cale immediately began undressing Kelsey before he quickly stripped himself down. He pulled a chair to the center of the room before sitting down on it and pulling her into his lap with her facing him. He kissed her deep before sitting her on his cock, his length sliding deep inside her soaked cunt.

“Ooohhh, I can’t believe this is gonna happen!” She moaned out as she took all of his cock.

She began furiously riding his cock, overcome by the complete lust she was feeling for the guys that were going to completely take her. Over and over again, she slammed down on his hard shaft before beckoning Brian towards them. Once he was within reach, she grabbed his cock and began stroking it.

“Oh, fuck! Come closer, ohhhh, I want you in my…fuck! Mouth!” She tried to say, but had a hard time talking between her moans.

Brian moved closer to Kelsey before she hungrily sucked his cock into her mouth, moaning all around his shaft as she rode Cale as best she could while his fingers were buried in her ass. She was truly lost in the moment, reveling in the potential pleasure that was soon to be added as she thoroughly lubed his cock with her saliva. She couldn’t wait to have him in her ass, to have the feeling of being full, to be stretched open. The thought of that caused her pussy to tightly clench around the throbbing cock she was riding.

“My ass, now!” She demanded with slutty filth as she came to a stop so he could work his spit-soaked cock into her most forbidden hole.

He slowly sank his shaft inside her puckered star, inching deeper and deeper inside her ass as he let her adjust to the invasion. It had been awhile since she last had a cock in her ass so it was slightly uncomfortable for her until she adjusted to the massive intrusion. It didn’t take long until she was ready to go.

“Fuck me already! Both of you!” She demanded as she tried to pull Brian deeper into her ass. “Fuck, yes!”

Cale held her still as the two guys began to fuck her, both building a steady rhythm until she were plenty used to being double penetrated. They could feel each other through the thin barrier and, at first, it was kind of awkward, but they also realized that they needed to be OK with it if they were to continue to fuck Kelsey.

“Oh, fuck, fuck, fuck, fuck! This is fucking amazing!!” She shrieked out, as she looked back at Rachel. “You have no idea what you’re missing out on, Rach! Fuckkkkk!” An orgasm racked through her body as she tightly clenched both cocks that were inside her. The sudden orgasm seized all movements of her body, causing her to rigid, as her friends took her hard and fast.

“This is fucking hot…” Rachel moaned as she continued fingering herself while she watched her three friends fuck right in front of her. She sat on the kitchen counter, one leg hanging off while the other was on the counter itself, while her fingers were busy in her aching cunt. She wanted to join in, to be fucked like that, but she wanted to keep it strictly as a fantasy to use on the nights she fingered herself when she had no one to fuck.

Kelsey was consumed with the pleasure of being totally full. The only thing missing was the fact that she didn’t have a cock to suck on. That would’ve just completed the filthy cycle, truly making her a slut at the moment. Oh how bad she wanted it. How so very bad she wanted to be stuffed completely full of throbbing cock.

“Oh, fuck!” She screamed out again as the slutty thoughts ran through her head.

Cale and Brian kept simultaneously fucking Kelsey on that chair, Cale on bottom, while they kept it simple. There was really no need to switch things up considering the intoxication level of all three of them was a little higher than they all would’ve liked. The three of them became lost in what was going on, consumed in the total bliss of the filthy acts taking place. But they knew it couldn’t go on forever, it had to eventually end.

The moans filled the air as all four of them strived to cum together. Each guy planned to fill the hole they were respectively inside. Hearing Rachel moan out her approval from the kitchen counter was enough to spur on each guy to cum deep inside the girl that was becoming a slut – whether or not she’d actually be a slut for anyone but them would still be up for debate.

“Fill me up! I wanna feel both of your guys’ cum filling me full!” She moaned out her filthy demand, wanting and craving to feel their seed splash against her insides, completely satisfying her slutty needs at the moment.

After twenty minutes or so, each guy grunted their approval, shooting rope after rope of cum inside her before slipping out of her tight holes for her to clean them up.

Jackson Hole Resorts opened a lot of doors for all of them, especially Kelsey as she were able to fulfill one of her fantasies. Rachel ended up fucking a random guy to set her number at two. Kelsey decided she only wanted Cale for the remaining time they were there. Brian slept with a random girl, but then later found out that she had a boyfriend. Talk about an awkward situation.

They all returned to Oklahoma happy and refreshed as they all had hoped would happen.

Published 
Written by jhmik_88
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