The Best Damn Si Trip Ever

When Mark woke up he saw cars speeding past him on both sides of the car. In the seat in front of him was John and to the side of John was David, both of whom were fast asleep. John's dad was in the driver seat, exhausted as hell after driving since 4 A.M. He knew it would pay off though as they could just start to see the mountains and it was only ten o'clock.

Mark was looking forward to the coming weekend. It was his junior year spring break and him and his two best friends were headed to Colorado with John's dad -- the coolest guy you'd ever meet. John's family owned a cabin in Vail and the three would spend the weekend skiing all over the mountain.

Mark, John, and David had been best friends since the beginning of high school. They played football together and were practically inseparable on the weekend, unless it was to go fuck a girl or something. They always went to parties together and slept at each other's houses to the point that they had their own toothbrushes there. They had fun together, but they couldn't wait to get out of their boring city and get a chance to make memories for a lifetime.

They had plenty of activities planned for the week. They had an ounce of weed and a bong and some joint papers in Mark's bag, two handles of some fancy vodka in David's bag, and that was all before John's dad had stopped at the dispensary. John also claimed to know some famous rich-kids whose families had cabins up in Vail. According to him, the girls were always down to fuck since they usually didn't have to deal with the guy after the vacation is over.

Mark was happy as he slowly drifted back off to sleep, the easiest way he knew how to keep himself busy. When he awoke, Mark saw what seemed like a winter wonderland. Snow-covered pines covered the mountain above and below the windy road that they were on. By that time, David and John were awake as well but were too preoccupied with the picturesque seen to notice that Mark had woken up.

"Hey sleepyhead, finally woke up I see," John said after a minute in a playful tone.

"How long have I been out?"

"It's noon and we're almost to Vail guys. Do you wanna stop somewhere to get lunch or just go to the house first?" John's dad chimed in.

"I say food first, I'm starving," David said.

"Me too," echoed John.

"Agreed," Mark said, and it appeared that the vote was unanimous.

After about ten minutes, their car pulled into the village of Vail and arrived at one of those restaurants that serves breakfast all-day and just calls it "brunch". They ate their food in a hurry and decided to walk around for a bit and look at the shops.

John's dad went into a men's shoe store that looked more aimed towards middle-aged men so the three kept walking. About halfway down the strip of shops, they walked past a sex shop with some interesting displays.

"Ha look at that," David said giggling at the sex swing used to tie up and fuck people while they are hanging from the ceiling.

"I bet you'd love to be tied up in that," John said, giving David a weirdly seductive look.

"Shut the fuck up weirdo," David said, half-mad but half-laughing, and the three all laugh it off. Those kinds of comments were nothing new from John. John was a super dominant guy in everything he did -- sports, school, games, relationships -- to the point that he always had to kind of sexually belittle other guys by saying things like "when I fuck you" or "come suck my cock." But, John was a super straight guy in every other regard. He had fucked so many girls but could never stay committed to one. That was likely because girls were always all over him since he was the hottest guy in the school. He had a beautiful set of abs imprinted into his olive-tan skin that looked perfect on his hunky 6'3" frame. Most people had heard the rumor about John that his dick was ten inches when hard. To John's friends, the ones that had known him for so long and seen him get out of the shower and such, that wasn't just a rumor.

The three continued to stroll around the shopping area until they finally bumped into John's dad near the exit.

"You guys ready to go?"

"Yeah," the three said in unison.

"Alright, how about a trip to the dispensary on the way home?" John's dad proposed.

"Hell yeah, Dad, that'd be awesome!"

The group made their way back to the car, hopped in, and headed to the dispensary that was located about 20 minutes away. When John's dad came out, he had the widest variety of edibles and weed candy the teenagers had ever seen. They then headed off for John's cabin and the true start to their week at last.

When their car pulled into the driveway of the stately house, John's friends remarked at his understatement calling the place a cabin. The house was big but in no way over the top. The real nice part about the house was just how luxurious it was.

They unpacked the car and took their stuff inside to figure out the rooming situation. John explained that there was a basement with a pool table and movie theater, a main floor with the kitchen, dining room, living room, and three bedrooms, and an upstairs that had two big rooms: one was another living room type area, and the other was a big room with five beds.

It was decided that the three would take the big room upstairs and leave the main bedrooms for John's dad. They lugged their stuff up to their room and had a short-lived fight over who would have what bed. Just as they were getting their stuff settled and starting to unpack their things, John's dad came in the room.

"Hey guys. One of my good buddies from college is in town staying on the other side of the village. He invited me over for dinner and a drink or two so I think I'm gonna head there in about 30 minutes."

"Alright, cool, sounds good Dad."

"Do you guys want me to order you a pizza or something? I feel kinda bad just ditching you guys here."

"Yeah a pizza would be awesome. But don't worry about leaving us here, go have some fun. We have plenty to do to keep us busy," John said and he was right.

That answer seemed to be enough to John's dad and he headed out of the room to go call a pizza shop. Right as he left, the three gave each other a "we have the perfect opportunity to do whatever we want" kind of stare.

"Shit, well this night sure did get a hell of a lot better," David said.

"What should we do?" Mark asked.

"I say we get fucking hammered," John said as he unzipped David's bag and took out one of the massive handles.

"I am completely with you on that one. As long as we can smoke a little weed though too," Mark said.

"I'm not one to complain about smoking weed or drinking. I'm down," David said, agreeing with his two other friends.

"I'll go grab some chasers, we probably have some pop in the basement."

John came back a few minutes later double fisting some two-liters of Sprite. Almost immediately, John popped the top and party stopper off the handle and started to drink. They each took turns with the handle, each taking a few pulls before John's dad shouted something from below.

"See ya boys. I'm headed out. Don't have too much fun," John's dad said while laughing and thinking back to how fun his high school days were.

They continued to drink for about thirty more minutes until each of them was sufficiently drunk but starting to get bored.

"You guys wanna go smoke some weed?" John half-mumbled.

"Hell yeah let's go," Mark said as he stumbled over to his bag to grab the bud and the bong.

John led his friends down the windy spiral staircase to the main floor and then down another to the basement. John walked to the back where there was a door to the outside and opened it up. Mark loaded a bowl and the three sat down at a table under the deck that was shielded from all of the snow. After each had taken a hit they wanted to continue but were starting to get pretty cold.

"Hey is that a hot tub?" David said, point to what was none other than a hot tub about a hundred feet away down the steps and in the middle of the backyard.

"Hey, you didn't say that you had a hot tub. If I would have known I would have actually brought my swimsuit," Mark said.

"Yeah, fuck dude."

"Chill out guys. I've never even really used a swimsuit anyway, usually I just go in my underwear," John said, trying to calm his friends down.

"I say we have another bowl or two then we go hop in because I am fucking freezing," Mark said.

The three agreed and quickly smoked their next two bowls. John advised that it would be best to take their clothes off inside and leave them there so that they didn't get any snow on them. The friends collectively stripped down to their underwear and Mark couldn't help but to catch a little peak.

David was wearing a pair of American Eagle boxers that just barely showed his soft dick pointing out. David was handsome but he wasn't anything too special. He had a mop of brown hair on the top of his 5'11" frame and was as pale as the snow outside. He had a nice body though and was muscular from his time spent swimming as a kid. His best feature though was his thick ass that perfectly complemented his figure.

John on the other hand was wearing a pair of white Calvin Klein boxer briefs that perfectly outlined his bulge. John had a thick happy trail leading down to the seam of his underwear and a light coating of upper chest hair. John could have been a model because he was just that damn hot.

Mark, if forced to choose, would probably have fallen somewhere in the middle of John and David on the spectrum of hotness. He had short blonde hair and a sexy blonde stubble. He was tall, muscular, and had a nice set of hair leading to his bulge, perfectly displayed by his tight Tommy Hilfiger boxer briefs.

Lacking their inhibition, the three made a mad dash for the hot tub. Mark jumped in first, followed shortly after by David. John lingered though, and in his drunkenness, decided that his underwear was unnecessary. As soon as he pulled down his underwear, his soft but still very large cock popped out and hung confidently among his trimmed but thick pubic bush.

"What the fuck are you doing bro?" David said.

"What? A guy can't have a little fun?" John said as he splashed into the hot tub in all of his nakedness.

"It's just a little weird dude. Keep away from me with that thing though, it could poke your damn eye out."

"Well if it's so weird then why were you staring at my dick long enough to see how big it is?"

"It's not like it's really a secret. The whole school, hell, maybe even the whole damn world knows how big your dick is," Mark chimed in.

"True," David and John both said in unison.

Tensions eased and the three friends continued to enjoy the hot tub and its effect on their already altered states. Mark was staring off into the distance just as he started to feel something near his thigh. He looked around for a second, thought nothing of it, and kept looking off into space. Then, for a second time, something touched his thigh and moved up towards his dick. He looked down.

"What the fuck bro?"

"Chill out I'm just messing around," John said.

"Yeah well you don't have to put your fucking foot on my cock."

"Well I may be wrong, but it looks to me like you liked it," John said, motioning towards Mark's slowly growing cock.

Mark looked suddenly flustered and tried to cover up his dick and think about anything else in the world to make him soft. John sat up so that he was standing in the hot tub, his semi-hard cock just above the water, and started moving towards Mark. Mark continued to stay sitting and John stood in front of Mark and put his hands on the edge of the hot tub and on either side of Mark so that he was encircling him. David looked on and began to be turned on while his confusion grew as well.

John reached out and grabbed Mark's cock and slowly began to stroke it underwater. By a minute or so later, John's hand would reach out of the water to reach Mark's fully erect length. The odd scene continued for what seemed like hours to Mark, but was actually just a few minutes, without barely any talking at all. Finally, David initiated the talking while he stealthily jerked off his cock.

"You guys wanna maybe take this inside? My hands are getting super clammy."

The three friends got out of the hot tub and ran inside as fast as possible. They dried off and decided that they should probably shower. They walked upstairs to discover a pizza on the doorstep that they must have missed while being outside. Before showering, they ate their pizza and the sexual tension had seemingly left the room.

Once they were done eating, John explained that there were bathrooms in every bedroom so it would be the fastest to all use separate showers. They all headed their separate ways to their separate showers. David and Mark finished around the same time at their showers downstairs and walked up the stairs together with their towels wrapped around their waists.

When they got upstairs, they discovered John on his bed, furiously jerking off his monster cock with his eyes closed. He opened them just as David and Mark got in the room.

"What's up guys? Sorry, I'm all horned up after that little hot tub session I just have to get off."

"What the fuck bro? Why are you always acting so gay?" David said.

"Don't act like you didn't like that shit. Both of you were hard as rocks. Mark was while his dick was in my hand and so were you David while you were trying to jerk off in the corner."

"I... well.. I mean.."

"Shut the fuck up and come put your lips on my cock," John said. David didn't move, he just stared at him. Finally, his drunken temptations took hold and he made his over to John's bed, dropping his towel and exposing his hard cock in the process.

David put both knees on the bed and sat in front of John. He slowly grabbed his cock after minor coaxing from John and started jerking him off. In the meantime, Mark was intrigued and dropped his towel and sat next to John as well.

Finally, David put his lips around John's fat cockhead and began sucking his first cock. He slowly sucked up and down until he got his rhythm. He tried to envelope all of John's dick that he could, but because it was so thick he could only get maybe three inches of him in his mouth.

While David was busy with John's cock, Mark grew harder by the minute and started to feel up John. Staying with the theme of John constantly making the first move, John went in for a kiss and started to make out with Mark. He pressed his tongue into Mark's mouth in a slow and sensual wrestling match with Mark's tongue.

David continued to jerk off John's cock but mover over to suck Mark's meaty rod. After a few minutes, John started to take command over the situation. He got up from making out with Mark and moved behind David. John put his large hands on David's muscular and defined bottom, and with a second movement gave it a hard smack. All David do in response was to just moan. John leaned over and gave David's freshly showed asshole a lick. Then, John started to eat out David's ass just like he would with any girl's pussy. By the end of it, he had David moaning like he would have any girl too.

As David continued to suck Mark's cock, John entered one finger into David's tight hole. David yelped, but he soon adjusted. Over time, John slowly entered another finger, and then a third until he had David practically begging for a cock in his ass.

"Fuck, David, I'm... I'm... I'm about to cum," Mark moaned.

David was in no way phased and continued to suck Mark's cock. Mark looked like he was about to explode, and he suddenly let out one final scream. Jet after jet of cum hit the back of David's throat, all of which he swallowed. He continued to suck on Mark's cock until long after he came and there was no cum spared.

Just then, John ran over to his bag, unzipped the front pocket, and grabbed a clear bottle of some kind of liquid out of it. He hopped back up of the bed, opened the bottle, and squirted some of the liquid onto David's virgin hole.

"Ah, lube. I see you were prepared for something like this to happen," Mark said and winked at David.

David covered his cock in the lube and set in on David's hole. "You ready to lose your v-card Davey?"

"Uhhhh, yeah, I really want to. But please, just go slow, I just don't want it to hurt," David said.

"No promises," John said as he slipped the head of his thick cock into David's tight ass hole.

Immediately, there was screaming and pleas to stop. John would have none of it and got his friend to calm down and told him to take deep breaths. He was determined to cum in his friend's ass. When the yelps of pain finally subsided, John slid more of his length slowly into David. He finally had all of his cock inside of David and let it sit there for a couple of minutes.

When David seemed relaxed, John knew the fun had just began. He started thrusting into his friend, slowly at first, but soon started to gain his pace. He increased his pace until he reached his rhythm, marked perfectly by the sound of balls slapping throughout the room. After a bit, John knew it would not be long before he came.

John increased the speed of his thrusting until David was screaming from a mix of pain and pleasure.

"Fuck yeah baby, I love that nice virgin pussy. I'm gonna cum all up in your pussy you little bitch till my cum is foaming out of your mouth."

John kept pounding David's ass until he could hold it in no longer. John's seed filled the depths of David's ass as John continued to fuck David through his orgasm. This made David reach his edge too as he started to cum all over the bed without touching his dick at all.

John slowly removed his cock and watched his cum drip out of David's asshole. By this time Mark was recharged and ready to try fucking a guy for his first time too. He didn't even bother to lube up his cock as he moved behind David. In one swift motion, Mark thrust all of his length into David's newly established cum dumpster of an asshole.

Mark pulled David's hair and rapidly thrust into David, making his screams turn more into ones out of pain than out of pleasure. Due to all of the excitement of fucking his first ass, Mark wasn't able to keep it together for long at all.

After a few minutes, he knew he was about to cum. He pulled his cock out of David's ass and moved towards his head. David, expecting to receive Mark's load in his mouth, open up his mouth and moved towards Mark's cock.

Mark slapped David. "Keep your mouth closed you little bitch. I'm gonna make you look like the fag that you are by blowing my load all over your face."

Mark increased the speed at which he jerked off his cock, his breathing increased, and he grabbed David's head with one hand to hold it in a stationary position. After a minute, he finally blew his load all over David's face.

The first jet hit David's forehead and hair, the second went right on his eyes, the third on his mouth, and the last few over his chest. David was painted with cum from head to toe. John, David, and Mark then began a three-way kiss, sharing each others saliva and exchanging Mark's cum. After a bit, the kissing stopped, and the three best friends layed in bed naked while trying to comprehend what had just happened.

"Damn, that was fun," David said.

"Yeah, I didn't know that we had such a little slut for a best friend," John said.

"Hey I didn't know till just now either, but damn I really love cum," David responded.

"Well, I'm sure as hell looking forward to the rest of the trip I don't know about you guys," Mark said.

The three friends all agreed with that statement. After a while, they got out of bed, took a group shower instead of solitary ones, and headed out to the backyard to smoke another bowl before the night ended. Damn, it was gonna be one fun trip.