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The Wager

"The embarassing payment of a lost wager turns out have several twists and turns"

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Author's Notes

"This is definitely a different sort of story. While there is no actual sex that happens during it, I find it to be very sexy. Since it kind of doesn't fit into any real category, I decided to list it as a "Humor" story and bump up some of the sarcastic bits. <p> [ADVERT] </p>I doubt that anyone will be rolling on the floor with laughter, but hopefully it will elicit a chuckle or a smile here and there."

As Nick approached the Coquina Beach changing cabanas, he saw that Max and Jay were eagerly waiting for him. They both smiled and laughed from the moment that they saw him, clearly eager to collect on the debt that Nick had owed. Jay made an overexaggerated waving motion that looked as if he were flagging in an aircraft on a landing deck.

Nick took a deep breath. He knew that he was in for a rough day, at least the next hour or so of it. Putting on a brave face seemed like the best way to deal with the situation. Max and Jay would surely heap on the punishment even heavier if Nick were to protest or try to hold out on “payment.”

Both of the guys were wearing long swim trunks and sandals. They each had a t-shirt tucked inside of the waistband of their trunks that dangled phallically between their legs. Max also had a backpack slung over his shoulders, presumably containing whatever devices were needed to extract the payment of Nick’s debt.

“Beautiful day at the beach, isn’t it Nickles?” Jay chirped.

“Yeah, and who would have thought that it would be this busy during spring break? I guess you are going to get to make a great first impression on a lot of people today,” Max added.

Defiantly, Nick responded, “Yep, I see a lot of cute girls out there. I am sure that some of them will like what they see.”

Eager to kick things off, Jay unzipped Max’s backpack and rummaged through it. After a brief search, his eyes lit up. With a wide smile on his face, Jay extended his closed hand toward Nick.

Nick placed his hand underneath Jay’s and a shiny, bright yellow piece of cloth spilled onto his hand. Nick almost dropped it and he scurried to gather it up and quickly conceal it in the front pocket of his shorts.

“We picked that out just for you, my friend,” Jay remarked. He was clearly quite pleased with himself.

“Time to pay up, Nicky!” Max declared.

Nick slowly walked to the changing booths. He ducked down, just to make sure that nobody was inside before he attempted to open the door. After stepping inside, he hooked the flimsy, little latch on the door. As he turned his back away from the door, he removed his backpack and tossed it on the ledge at the back of the booth.

He, once again, took a deep breath. His mind contemplated why he had ever agreed to that stupid bet in the first place.

It was roughly a year prior when Nick had made the wager with Jay and Max. Nick was a lifelong Boston Celtics fan and they were facing the Golden State Warriors in the NBA finals. Jay and Max were the typical “bandwagon fans” and given the success of the Warriors in recent years, they were currently rooting for them.

After a bit of back and forth, the boys had agreed that the loser, or losers, of the bet would have to be paraded around the beach during spring break while wearing a Speedo. It seemed like a good bet for Nick to accept since he would essentially get twice the payment that they would.

Unfortunately for Nick, he would lose the bet. Since the finals concluded in June, the boys would have to wait until the following year to collect on the bet. Nick hoped that they would forget about it, but they clearly did not.

He reached into his pocket, pulled the Speedo out, and tossed it onto the shelf next to his backpack. He unzipped the backpack and felt like it was best to just “rip the Band-Aid off” in one go.

Nick slid off his sandals and removed his shirt. He tossed the shirt into the main pouch and placed both thumbs inside the waistband of his shorts. In one motion, he removed both his shorts and underwear. After “stepping out” of them, he tossed them into the main pouch as well.

Standing there “bare-ass naked” with his back to the door, Nick reached down and grabbed the bright yellow Speedo. As he held it up, he immediately noticed two things. Firstly, it seemed to be quite small in size. Secondly, there was the Speedo name both across the rear of the swimsuit and on the front hip. That seemed to be pretty standard from what he had seen, particularly the one on the front. What made it unusual was that the letters were all erratic and multi-colored.

Nick had to smile. The guys really did “get him” this time. It was obvious that the lettering was a “Pride” reference. Nick shook his head in disbelief as he did a “face-palm.”

Distracted by the logo, Nick went ahead and tried to put the swimsuit on. He nearly toppled over as he tried to pull it up. It was getting really snug and it was barely past his knees. He took the Speedo off and looked for the tag, only to find clearly printed that it was waist-size thirty.

Nick had played sports with the guys all of his life. Max was tall and fairly slender while being reasonably muscular and strong at the same time. Jay was fairly short and skinny, but he was lightning-fast. Nick, however, was more of the big, sturdy, powerhouse type. He would have ideally worn a size thirty-four if not a thirty-six.

They had well and truly set Nick up. He remembered back to when he protested having to purchase the Speedo that he would have to wear to pay off the bet. He should have realized that something was wrong when they were so eager to volunteer to buy it for him.

“You guys!” Nick shouted.

They approached the door “all smiles” as they clearly realized why they were being called over.

“This is a size thirty. I can’t fit into it!” Nick protested.

Max piped in first, “Sorry, dude. I just picked up what I would have ordered for myself, minus the rainbow logo of course.”

Jay was the next to contribute, “Not me. I would have got a twenty-eight. I like mine nice and tight so I can show off my big, thick slab of meat!”

“Can we do this another day? I need to get a swimsuit that fits.” Nick appealed.

“Sure, Nick. I don’t think that would be a problem. But we will have to bump up the payment from one hour to two,” Max countered.

Jay chimed in, “Yeah, that seems totally fair.”

“Never mind!” Nick fired back. “I will make this work.”

“They are supposed to fit tight. That’s how you will set a new world record in the one-hundred-meter freestyle!” Jay added.”Less resistance is a good thing.”

Nick grabbed ahold of the swimsuit and tried to pull and tug at it as hard as he could, hoping to stretch it out as much as possible.

He decided to give it a second try. It didn’t get really constricting until it got to his mid-thigh. Nick gave it one last hard pull and got it roughly into position. The fabric was very stretchy, so it seemed like he could make it work, but the elastic around the leg openings was extremely tight.

Nick worked his fingers inside of the leg openings and tried to stretch them out. As he did, he tried to work the swimsuit up and into place.

It was probably as good as it was going to get. There was a significant amount of exposed butt crack in the rear and Nick’s limp cock was pointed directly upward, looking like it was being strangled by the swimsuit. Deciding that things looked a bit too explicit in the front, Nick elected to tuck his cock as far down as he could. There was a small pocket of space down there since the leg openings fit so tightly.

He put his sandals back on, zipped up his backpack, and grabbed ahold of it. As he approached the door, he gave himself one last look-over. He definitely looked like ten pounds of shit stuffed into a five-pound sack.

Nick unlatched the door and stepped out. The boys were eagerly awaiting him. Max immediately let out a howl that drew the attention of everyone in the vicinity. Max and Jay continued to cackle and howl like a pack of hyenas for what felt like forever. It quickly became one of those contagious situations and even Nick couldn’t stop laughing. Max even fell down to his knees and Nick wondered if he was going to laugh so hard that he would piss himself.

The laughter finally ceased, although Max continued to chuckle and wipe his eyes. “You look great, man! Seriously,” Max exclaimed.

“We need a fashion show,” Jay added. “Come on, darling, give us a little spin,” he remarked as he made a twirling motion with his finger.

As Nick reluctantly spun around Max commented, “Yeah, that’s a lot of crack, man.”

“Hey, wait a minute…” Jay interjected. “Dude, where’s your cock?”

Max immediately responded, “Where’s your cock, dude?”

The two went back and forth for what felt like an eternity until Nick insisted that they get going. They dug through their backpacks and started to set up their relay system. Nick was instructed to wear his earbuds, while Max and Jay followed behind him giving him instructions via their phone. They set a timer to one hour, which was the length of Nick’s agreed-upon punishment. Just as Nick got ready to grab his backpack, Jay intervened.

“That looks like it’s heavy. I’ll carry that for you. Besides, I wouldn’t want to deprive the public of seeing you completely unobstructed.”

Nick handed his backpack over. “Fuck!” he thought to himself.

The guys walked him around for a while. They picked out individual targets for Nick to acknowledge as they passed. The response was pretty predictable. All of the attractive women either laughed at him or rolled their eyes. Most of the men scoffed at him. The only positive responses that Nick received were either from unattractive or much older women as well as gay men who were clearly given the green light by his swimsuit's “Pride” lettering.

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Max spoke into Nick’s headset, “Jay, have you noticed that Nick’s ass is as hairy as it is big?”

Jay mused, “Yes, yes I have. At least we don’t have to worry that it will start to look good after a while.”

Nick outstretched his hand behind him with his middle finger extended.

“Oh, he is salty today!” Max chirped.

“Salty as a sea water-soaked Speedo," Jay added.

As Nick looked back, the two boys were fist-bumping in celebration of their witty banter.

The guys continued to display Nick for some time before getting bored with the entire process. Roughly a half-hour into his punishment, the guys called Nick over and shuffled him off to the side of a refreshment stand that was located on the beach. They both stared uncomfortably at his crotch before commenting about the lack of a bulge in the front of his Speedo.

Max commented, “Seriously, bro, do you even have a dick in there?”

“Ha-ha, guys, it’s tucked down,” Nick responded.

“Like in your ass?” Jay fired back. Nick started to shake his head as if he was indicating that he didn’t want to continue that line of conversation. “Well, pull that thing out of your ass and show it off!”

“That is an excellent idea, Jay,” Max added.

Nick looked around nervously, briefly protesting that somebody might see him rearranging things down there. The guys insisted, however, and blocked off the public view pretty well. When he was finished and pulled his hands away, the guys, once again, burst out laughing.

The distinct outline of his cock as well as “the boys” was pretty unimpressive. His dick was clearly quite soft and it looked as though it was being smothered by the tight fabric. Nick’s face turned bright red. It was easily his most embarrassing moment thus far.

Then Jay chimed in, “Chub it up, man.”

Max’s eyes immediately lit up, “Yeah, that’s good, Jay. Make it rage in there, Nickles!”

Nick’s eyes pleaded for the guys to say that they were just joking, but they simply stared at him as if to say “Go ahead.” He started to gently rub a couple of fingers over the front of the swimsuit. To his surprise, the silky texture of the skin-tight swimsuit actually made for some intense sensations on the underside of his tender cock. That combined with some newfound exhibitionistic tendencies turned his cock rock-hard very quickly.

“Try not to cum!” Jay joked. “Oh, wait…”

“No, no, no,” Max interjected. “I can’t handle that.”

Nick pulled his hand away and looked to the guys for approval. Sticking straight up, his erect cock was getting dangerously close to the waistband of the mid-rise Speedo. In its swollen condition, it took up considerably more room inside of the tight confines of the swimsuit. That constriction left a well-defined outline, particularly of the head.

“Yeah, I couldn’t do that. The top half of mine would be hanging out right now,” Jay bragged.

The guys directed Nick to reposition his cock inside of the Speedo several times before deciding that swinging it over toward his left hip was the best option. Nick was actually relieved by that decision. He had feared that if it remained upright, the head of his cock would begin to peek out as he walked and the swimsuit shifted.

The guys were eager to show Nick off, once again. Even better for Nick was the fact that they had wasted almost fifteen minutes prepping him for his second run. They hurried him back to the beach and their new instruction was for him to try to make eye contact with someone and then direct their eyes downward. The reactions were mostly the same as before, but much more pronounced.

As they walked down the beach, they approached a very diminutive Latino man who was also wearing a Speedo swimsuit.

Max ordered, “Go talk to the dude in the Speedo and ask him how he likes your swimsuit.”

Nick reluctantly approached the man, who was looking in the opposite direction at the time. Once he turned toward Nick, he stared at the front of his swimsuit for what felt like an eternity. He pulled down his sunglasses to make eye contact with Nick. Then he licked his lips seductively and stated that it “looked delicious.”

“Turn around and show him your ass!” Jay exclaimed.

Nick complied, but when he turned back around the man’s expression had changed considerably.

“Yeah…” the man stalled, stretching the word out for an extended period of time. “That’s not really my thing. You know what? You are exactly my friend Carlos’ type. He is right over there. Should I get him?”

“No, no that’s alright. Sorry to bother you,” Nick mumbled as he scurried away.

He was thankful that Jay’s miscalculation freed him from the man’s direct advances, although he was sure that Jay probably didn’t realize what he had done.

The guys continued to make Nick casually interact with random people until they found a new target. There was a bodybuilder-type that was working out on the beach in an attempt to show off for all to see. The guys clearly targeted him because they were sure that he would be appalled by Nick’s appearance.

Nick approached him in much the same way as the previous guy. This guy, however, turned and scoffed at Nick. He seemed slightly aggressive with Nick for bothering him. Once he sized Nick up, though, he clearly thought better of being too combative. While the guy was quite fit and muscular, Nick was a big, powerful guy and it would have been foolish to pick a fight with him.

The guy suggested that Nick should only show off his attributes that were worthy of being shown off and that what he had going on wasn’t working. Then he asked him to leave because he was “scaring off the chicks.” Nick was pretty sure that the girls weren’t lined up for that guy any more than they were for himself.

Nick asked for a “time call” and Max said that there were only a couple of minutes left. They hurried Nick down the beach and found one last target for him. There were two very lovely girls sunning themselves in their bikinis. They seemed to be college-aged or perhaps just a bit older than that. It was Nick’s worst nightmare.

As Nick approached, he recited his line, “How do you-” but was promptly cut off by the girl with long, dark hair.

“Beat it pervert!” she snapped, without even looking in his direction.

Nick looked back toward the guys, but they prompted him to continue on.

“I’m sorry to bother you,” Nick pleaded. “I would just really like your opinion on my swimsuit.”

The girl glanced at him briefly. Then she started to unload on him.

“My girlfriend and I aren’t interested in looking at your boner, so why don’t you fuck off!”

Her voice started to trail off at the end of the line as she seemed distracted by something else.

“Who are those two braying jackasses behind you?”

Nick stammered, “Oh, yeah, those are my friends.”

“Why are you doing this? I can tell that you don’t want to,” she observed.

“I lost a bet,” Nick admitted.

The brunette nudged her blonde-haired girlfriend who had previously been reluctant to even acknowledge Nick. They started to whisper back and forth in the way that many couples do. It was low enough that Nick couldn’t make out much of what they said. He did hear the blonde say “It looks just about right,” though.

“Have you ever had a threesome with two girls before?” the brunette asked casually.

Nick’s eyes grew as big as saucers as he contemplated what she had just asked him. Before he could even think of how to respond the blonde girl started to talk.

“We are a couple. But…sometimes we like to bring in a guy just for fun. You seem a nice guy and just the right size, too,” she said as she pointed her finger at his crotch.

“Sammy likes a little bit of girth, but nothing too oversized,” the brunette pointed out. Suddenly, Nick didn’t feel quite so insecure about his thick, but average-length, cock.

The girls claimed to have a hotel room in very close proximity. They outlined a few ground rules first, such as that Nick was to effectively be their sex toy for the night. There would be no oral sex given or received, at least not involving him. He was required to wear a condom at all times and explicitly told that he wasn’t to get a drop of cum on them or inside them.

“So what do you think, stud?” Sammy asked.

“Okay!” Nick fired back, sounding incredibly eager.

“By the way, I am Danni. Do you need to let your friends know?” the brunette asked.

Nick nodded and returned to the guys. He was all smiles as he tried to explain the situation. The guys, of course, didn’t believe a word of what he was saying. That was until the girls approached them.

“Sorry, boys. We are going to need to borrow your friend for a while. Don’t wait up!” Sammy taunted.

The guys looked shocked.

“That’s cool. Max and I would be happy to join you girls. We could really have a fun time together!” Jay offered.

“Yeah…that’s not going to happen,” Danni responded. “My girlfriend has her eye on your friend...” Danni gestured toward Nick, realizing that she didn’t get his name yet.

“Nick!” Nick enthusiastically offered.

Sammy added, “Thanks for showing Nick off for me. He is exactly what I was looking for.”

Nick quickly grabbed his backpack from Jay and turned toward the girls who lined up on each side of him. As they started to walk away, both of the girls placed a flirty hand on Nick’s backside. He responded by wrapping his arms around each of their sides. The three of them chuckled playfully as they left Max and Jay with stunned looks on their faces.

Published 
Written by SuccubusSlayer
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