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A Beach Vacation, First Night

by Pappa Jack


The four young men had been friend and roommates for the past two years at Valdosta State University. The time had come for the end of school and graduation. They had planned to celebrate with a quick vacation to the beach before they had to jump into the real world.

They were all ready for a break from school and needed to do some drinking and some fucking. Each one had nothing but sex on their mind. You could smell the maleness in the air as they talked about getting naked and getting off.

Heath was a 21 year old Psychology major, but far from a bookworm. He was a handsome 5'8" 165lb hairy otter type of man. His uncut dick was a full 7 inches and filled up his jockstrap that he insisted to wear. Heath was the brains of the group; however, he was not the leader.

Jeff was 20 but looked older. He worked summers in construction for his father. His physical experience gave his 6'2" 180lb body a firm and tight "5 day a week workout" gym look. Jeff dreamed of becoming a real estate king. He could do almost anything and was good at what he did. Jeff was a dark complexioned, summer blond with a beautiful thick 8 inch cut cock with huge low hanger balls.

Jackson (Jack) was the leader of the group. He was the oldest at 24. He had spent time in the Marines after high school. He was back in college as a criminal Justice major; he had an interview with the Georgia State Troopers. Jackson was a rugged looking man with the attitude to match. At 5'10" and 195lbs, he was all muscle. Jack was never a modest man, thank the marines for that, but he had reason to show off his thick uncut 6 inch dick that was kept clean shaven. He was proud of his short cock that must have been a "grower"

Travis' most noticeable feature was his beautiful flowing dark red hair. He graduated tops in his class in the department of chemistry. His 6'frame and standard issue 21 year old body was a pleasure to look at. Travis had a cut cock also, but he was a shy type of person and none of the others had ever seen him naked.

All four had going through a long list of girlfriends, but none were ready to make a commitment. Their attitude was that there was way too much to experience than getting married and having kids. They were ready to enjoy life and have some fun. Never, in the two years that they had roomed together, had there been any indication that there was any type of sexual attraction between the men. Without a doubt, they were 100% straight.

Jackson had made reservations at the beach for four nights and got a great deal on a two bedroom condo. The four friends packed light into Travis' Ridgeline and made the quick short drive to Pensacola Beach. Upon their arrival and check in they began to realize why they got such a good deal on the condo.

There were two bedrooms, but only two beds, one a double and one a king. The view was of a parking lot and not the Gulf. The entrance was on the third floor without an elevator. A TV in the living room was far from being HD. On the positive side, the condo was clean and the air worked well.

First item of business was for the men to decide the sleeping arrangements. Jack tried to keep the group from being too mad by telling them that during the stay, they were not going to spend too much time in the condo. They would be spending most of their time at the beach and at the clubs.

"Sure, Jack" Heath said, "but we do want to have a place to bring girls back to"

"Okay, I understand that, and we will work out a system." Jack commented.

"Seems to me that there are two beds and four of us; there is a sofa-sleeper that can accommodate a person. Thus, option one, two of us will have to sleep with each other in the king bed or option two; one of us will be sleeping on the floor." stated Travis factually as he looked at Jack.

"Well I am not going to sleep with anyone, and I am not going to sleep on the floor for the same money that I have paid as someone who sleeps in a king-size bed." Jeff blurted.

"That makes sense to me too." Heath chimed in.

Travis reasoned, "The one who made these reservations ought to be the one sleeping on the floor.”

"Hell no!" exclaimed Jack. "There should be another solution, if we will just think."

The men sat at the kitchen counter, drank a cold beer and thought about their situation. Jack was under the gun to come up with a working solution so that his friends would be happy and have a good time. He offered a fair and equal remedy to the problem.

"Let's have a competition for the king size bed each day. The winner will sleep in the big bed and can have privacy for fucking his guest. The loser will sleep on the floor and the other two will have a bed and a sofa." Jack grinned.

Heath thought about the proposition and always wanted to know the details before jumping to accepting the deal. He wanted to know what kind of competition and what the time frame would be for the winner to have the king bedroom.

Jeff offered, "We could have any kind of competition from a beer drinking to a piss off contest." Then he added, "I think that the loser should have to do more than to just sleep on the floor."

"Really?" Jack questioned, "Damn, What the do you have in mind?"

"Shit, Jack, I don't know. Use your imagination. I guess that the loser could be our houseboy for the night" Jeff snapped.

"Well that’s not a bad idea. I like that added element." replied Jack. "What do you think guys? Good idea?"

Travis offered that the deal be for 24 hours and that the competition be selected by the loser of the night before so that they would select a challenge that would be to their advantage.

All drank to the deal and came up with a plan for the first challenge. A jack off contest! Circle jerk style, winner determined by volume, not a race for first shot. There would be a porn movie playing and each could take their time but must be witnessed by the others when they shot their load into a glass. Each glass would be measured and the one with the most jizz would get the king bed for the night and the one with lest would be the houseboy for the group until tomorrow at this time.

Travis was a little reluctant about doing this, but after a couple of beers, he was willing to go the distance. After all this was graduation celebration. His friends were shocked to see him uncover his soft cut 9 incher.

"Man, where have you been keeping that monster?" Jack joked.

Travis responded, "I have had this for a long, long time, but during high school the gang would give me a hard time about my meat, so I decided to keep it to myself."

"Shit," Heath said, "I am fucking glad that we didn't decide to have a longest dick contest."

"Time is wasting men, I’m ready to get this over with so that I can hit the beach and bring some girls back to my king bed." Jeff said.

The TV was turned on and porn was popped into the DVD. Shirts came off, pants came off. There they stood, three in boxers and one in a fresh jock strap. "You can't jack off with these shorts on my friends!" Jack taunted as he stripped off the last of his clothing. The others followed suit.

With in a couple of minutes, all four dicks were at attention and the boners were being stroked with pride. This was a first for the four friends. Their apartment at school allowed for private bed rooms and a common area. They were totally involved in their school work that they never horsed around with each other.

When the porn got to the hot spot, all men started to make little noise that indicated they were not even aware of the others were in the same room.

Heath was the first to blow his wad and caught ever drop of his hot cum in the glass.

Jeff was next to bust a nut. He too caught his sperm in the designated glass. Already, the two were making comparison of their prized gifts.

The last two men to shoot started jacking faster and faster until both shot their hot steamy cream at the exact same time (Seems that Jack and Travis got turned on at the thought of jacking off with another man.)

The glasses were lined up on the counter and started the process of measurements. The winner is . . . JEFF--without question. And the loser was close but decisively . . . Jack.

Thus, the Master of the day was Jeff and Jack was to serve as the houseboy. Heath and Travis decided on their beds and got settled in for the day. Swim suits on and off to the beach on the "hunt" for their prize capture.

Jeff instructed Jack "Take my luggage to the masterbedroom, boy."

Jack bent down to gather his pants to get dressed when Jeff firmly said, "Do what I asked you to do FIRST boy." That is when Jack realized that things were going to be different for the next 24 hours.

"SIR, Yes SIR" was Jack's reply. Jack did as he was told and then he asked for permission to dress to go to the beach.

"Permission granted." was the answer that Jeff gave.

Night came and the guys went to the nearest and loudest club for a few drinks. Very little action and not very many good looking women. They decided to return to the condo and rest up for a full day tomorrow. After all, there were there for a full week, there was plenty of time to fuck around.

Once back in the condo, Heath and Travis decided to see how good a house boy Jack was. They made demands on him to bring them a drink or put this away. Nothing really demanding, until Jeff told Jack that he was not in Uniform. "The house boy will always be in the same uniform every night" Jeff claimed.

Jack asked, "Sir, may I ask, Sir, what the fuck will that uniform be? Sir"

Heath then spoke up and demanded that the houseboy uniform be a jock strap. Everynight the house boy had to wear the same jock strap as the night before and it was not to be washed--all week long. The reaction of disgust from the three others was priceless.

Heath was breaking free from his shell and enjoying the relaxation at the beach. The booze was helping him to loosen up.

Jack put on the jock strap and marched around the room for his buddies to see. They clapped in approval. Bedtime came and Travis found his bed, Heath was on the couch and Jeff went to the masterbedroom and called for Jack to come in and told him that he was to sleep on the floor beside the bed just like a little puppy. Jack did as he was told.

Jeff told Jack that there was a way that he could share the bed, but it would cost him. Jeff reminded Jack that tonight was his turn to have to masterbedroom to "fuck his guest" as agreed before. Jack was astonished at the request and stated that he was happy on the floor.

"You don't understand, boy" Jeff said in a deep commanding voice. "get into this bed now, boy"

"Sir, . . . yes sir." was Jack's humble reply.

Jeff was naked and wanted Jack to play with his dick and give him a hand job. When Jeff had shot his load at the handy work of Jack, he reached down and took Jacks hand and rubbed the cum into his chest.

Jeff had a huge smile on his face as he driffted off to sleep. Jack was just happy to have a bed to sleep in. The two of them woke up the next morning like lovers, in each others arms. Their friendship had gone to the next level.

Jack begged, "Please, Sir, don't tell the others what happened here last night."

"what happened here? I Don't have any memory of anything" was the reply from Jeff.

As the morning progressed time came for the next challenge and Jack was the one to name the activity. He selected a simple came of high card. The one who is delt the highest value card is the master and the low card is the houseboy.

Jack opened the deck of cards and shuffeled them with the flair of a vages dealer. Four cards face down in front of each of the boys. Jeff's card was an 8; Heath got the Jack of spades; Travis was dealt the King of hearts; now for Jack's card. . .a 5.

"Damn it to Hell" Jack shouted. "How the fuck could I lose at my own game?"

All three were laughing their Ass off at his reaction. "This is going to be a great vacation after all." Travis bosted.

To be continued . . .


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18 Gay Erotic Stories from Pappa Jack

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