Tom, Kevin, and John climbed off the plane into the humid heat of the Dominican Republic for their week long all inclusive vacation. The boys had always talked about taking a trip like this, but until now, there was always something that stopped them from going.
An hour later the boys made their way from check-in to the suite they'd be calling home. Kevin had already taken off his shirt, revealing the pair of grey boxers he wore high on his waist. Not wanting to have such a high tan line, he pushed his boxers and shorts down until his pubes started to show along with a hint of his ass crack.
Tom, who stood behind Kevin was enjoying the view, particularly since he knew Kevin wouldn't be wearing much more that week. The boys arrived at their suite and were surprised to see a spacious living room, three bedrooms, and a large deck complete with a hot tub. The boys dropped their gear in their rooms and Kevin and Tom grabbed a drink while John freshened up.
With John out of earshot, Kevin told Tom it was time to play Naked Embarrassed Tom, or 'NET', and explained what was about to happen. Kevin instructed Tom to strip to his underwear, a pair of white boxer-briefs, as Kevin did the same, stripping to his grey boxers.
When John returned to the boys, he wore a pair of boardshorts very low on his hips, with a pair of black boxer-briefs underneath. John was surprised to see the other two boys wearing so little, but as rehearsed, Kevin explained that they didn't want any tan lines. This made sense to John, but Tom replied that they'd still have tan lines, they'd just be lower down.
Kevin told Tom that tan lines were unavoidable, and he could roll his boxers up his legs, and pull his waistband down to minimize them. Tom then proposed a bet: if at the end of the week, Tom didn't have a noticeable tan line, then Kevin would suck his cock. If, however, Tom did have a noticeable tan line, then Tom would have to suck off Kevin and John, and he'd have to be their naked houseboy at a time, place, and duration of their choosing. Tom would also be forced to go to the clothing optional beach at home until his tan line was gone.
John wasn't sure that he wanted to be involved in this bet, but he had nothing to lose, and either way, he'd get to see one of his friends get sucked off. Tom, having shaken hands on the bet quickly pulled his white boxer-briefs off, throwing them inside before lounging face down in the warm sunlight.
Kevin and John spent a good portion of the next few minutes stealing glances of their naked friends ass. Ten minutes later, Kevin disappeared inside, returning with a bottle of sunscreen. He quietly snuck up on Tom, and squeezed an unnecessarily large portion directly on Tom's ass.
Tom laughed it off and started rubbing the sunscreen in, but Kevin stopped him, saying that he and John would do it, making sure to not miss any spots. John jumped up quickly at this opportunity, in fact, much quicker than he would have liked. Tom hadn't seemed to notice how quickly John responded, but unlike Kevin, Tom couldn't see John trying to adjust the obvious bulge in his shorts.
John's shorts rode so low, that apart from pointing his cock down, his cock would be covered primarily by only his boxers. As the two boys started to massage the sunscreen onto Tom's back, and particularly his ass, Tom's own cock grew to full size, as Kevin massaged his balls which sat between his opened legs.
A minute later, Kevin told Tom to turn over so they could get his front, but Tom refused, not wanting to show his hard cock to John, at least not yet. Kevin reminded Tom that there was a 'NET' benefit of letting them put the sunscreen on for him so no spots were missed.
Tom folded, rolling to face Kevin, who dropped his eyes to his friend's cock as Tom continued to roll onto his back, giving John his first view of Tom's massive cock. Kevin quickly dropped a massive amount of sunscreen directly on Tom's cock which he began to rub all over Tom's body.
John jumped in and paid particular attention to Tom's cock, which began dripping precum that John continued to spread around. Kevin let this continue until he thought Tom was about to blow. Kevin then took to his lounger, and tossed the bottle of sunscreen to Tom and John, saying it was his turn.
Kevin pulled the waistband of his boxers down until it was barely above the base of his shaft, and then rolled the legs of his boxers up into a pouch. The boys quickly got started on rubbing sunscreen onto Kevin, but we're initially hesitant to get too close to Kevin's crotch. Kevin sat up, throwing an arm out, pretending that his eyes had been closed, hitting Tom's still rock hard cock.
As John watched Tom's cock bounce, Kevin reminded the two boys that they'd need to make sure that they got a little under his waistband, just in case it moved. Tom didn't have to be told twice, and he ran his fingers under the waistband of Kevin's boxers, grazing Kevin's cock. John began making his way further up Kevin's legs, his hands now rubbing up against Kevin's balls, which were barely contained in his boxers. As Kevin's cock began to grow, a tent formed in his boxers, pulling them up, causing his balls to become exposed to John's eyes and fingers.
John was caught off guard by feeling his friend's balls, and instinctively told Kevin to turn over before realizing this took away his access Kevin's balls. Kevin now lay on his front and let the boys cover every bit of exposed skin on his body with sunscreen. Just as they ran out of skin, Kevin brought his hips off the lounger, and pulled his boxers down to give the boys access to the top half of his ass.
Tom and John each took one of Kevin's cheeks, and massaged them until Kevin pulled his boxers back up, and made his way inside to get a drink, telling Tom that he was sure he could handle getting John sun screened. John laid down on his chest and waited for Tom to start spreading the sunscreen on him.
Left to cover John alone, Tom straddled John, his balls resting on the seam of John's exposed lower back and waistband. Tom took great care covering John's back with sunscreen. As he finished, Tom went to turn around to start on John's legs. John grabbed Tom's leg, and reminded him to get under his waistband, as John didn't want to burn.
Tom quickly grabbed another dollop of sunscreen, and ran his fingers under John's waistband, reaching down just far enough to feel John's ass crack develop. With all of John's back covered, and Tom still straddling John's stomach, Tom's balls slid across John's skin as John rolled over.
John now looked down his chest seeing Tom's hard cock pointing straight at him as Tom started applying sunscreen to John's chest. John's cock was hard, and rested between Tom's ass cheeks, which gently moved back and forth causing a wet spot to form in John's boxer-briefs.
Tom ran his fingers under the waistband of John's boxer-briefs, running them through John's red pubes. Finished with John's upper body, Tom turned around and moved his ass onto John's chest, leaning forward to get sunscreen on John's legs, stopping only when he reached the legs of John's boxer-briefs.
Tom's position gave John an up close and unobstructed view of Tom's asshole. John was quite enjoying the view, but it came to an end as Kevin walked outside, asking if the boys were having fun.
Both of the boys smiled, their faces turning red from embarrassment. The three boys took their places on the loungers and enjoyed the sunshine, alternating laying on their chests and backs. What didn't change, however, was the direction that John and Kevin faced, being on either side of Tom.
The two boys always faced inwards, taking full advantage of their view of Tom's naked body. When their beers were empty, John volunteered to refill them, but Kevin quickly proposed that Tom go instead, because he'd need practice for his future naked houseboy engagement. Tom told off Kevin, secretly happy to have a chance to show more of himself to John, who didn't argue and certainly enjoyed the show.
A few days passed with Tom sunbathing naked each day, and forced to be naked at all times in the room, as per Kevin's rules for the current game. Tom only put clothes on to eat, swim, and explore the resort, which neither of the other boys seemed to want to do very much of, instead opting for time in their room.
Halfway through the week the boys made arrangements with the local travel rep to go on an adults only extreme excursion of zip lines, horseback riding, atvs, and waterfalls sponsored by one of the local clothing optional reports.
As Tom stood on the beach filling out forms for the group, Kevin pantsed him, yelling at the same time to attract attention to Tom's exposure. Tom was forced to drop the clipboard he held in order to free up his hands to pull his board shorts and boxers back up.
Having just been swimming, Tom's white boxers were near see through, meaning that despite only having been pulled about a third of the way to his knees, little was left to the imagination. Tom's boxers stuck to his legs, making it hard for him to pull them back up, giving Kevin plenty of time to jerk Tom's hips, forcing Tom's cock free and bouncing it around for everyone, their cute young travel rep included, to see.
Tom finally managed to get his boxers on, and then gave Kevin a playful push back onto the chair behind him, before continuing to pull his shorts up, finally regaining his dignity. Tom could see people all over the beach talking about his cock, many showing it's size between their hands as they retold the story to friends who knew they weren't exaggerating.