Todd's Caribbean Vacation

by flyguy91

9 Jul 2018 5647 readers Score 8.8 (90 votes) PDF Mobi ePub Txt


Todd hung up the phone with such excitement in his mind. He was finally going on a vacation. It had been a good year and change since he had been on a decent vacation. He was planning on taking off to the Caribbean with a couple friends for a week. He was just relieved to not have to worry about any type of work and soak up the sun on the beach.

He packed his bag and laid out all the clothes he was going to bring. A few shorts, a pair of jeans for going out, some short sleeved shirts and his swimming suits. He had a few nice speedos that he liked to wear from time to time but those were really to show off. He threw them in just in case.

The next morning, his alarm rang early and he was off to the airport. The trek down to the island was your usual busy crowd at the airport. The boys slept most of the way down. They arrived around noon and headed right for their rental. They had gotten a small beach front condo with a walk out porch to the public beach. Todd just stood at the door and was in amazement of the gorgeous view of the sea, sun, and palm trees. He squinted his eyes a bit, focusing on a man off in the distance on the beach. He wasn’t wearing any clothes! His larger, hairless balls moved from side to side as he walked along the beach and his cock seemed to be just as tan as the rest of his body. This man had spent a good amount of time naked in the sun.

“Is this beach clothing optional?” asked Todd.

“Yea, I think so.” His friend Greg responded. “Even better for us during the day!”

The boys unpacked and decided they all wanted to make their way to the bar for a few drinks. Todd slipped off his clothes and pulled on his swimming trunks. He wasn’t quite ready to break out the speedo. He grabbed his flip flops and headed out the back door to meet Greg and Randy.

They each ordered a pina colada and clinked drinks, toasting to a great start to their week in a tropical paradise. Todd sipped on the cool, refreshing drink and swiveled around on his bar stool. He noticed about 75% of the men and women on the beach were completely naked. He felt a little urge in him to want to do the same. He wanted to know what it was like to be in front of everyone stark naked. He had just recently been to a bathhouse for the first time a few weeks prior and that was very liberating in itself. But how could he suggest a day on the beach completely naked to his friends, without being subject to possible embarrassment?

The boys decided to grab their towels and run down the sand to find a spot to lay out once they had finished their drinks. After a half hour or so Greg suggested to run down and jump in the water. Randy agreed but Todd stayed back. He said he wanted to walk the beach. Todd wasn’t much for swimming anyway.

Todd grabbed his towel and started down the shoreline. It seemed to go on forever. He couldn’t see the end. The further he went down the beach, the crowd of people became smaller and smaller. Finally, he came upon a patch of sand and couldn’t see anyone around. He sat down and just breathed in the salty, ocean air. The rays of sun warmed his chest as he faced the sun and leaned back on his elbows. He glanced around to see if there was anyone following him. Had Randy and Greg seen where he went? It seemed he was the only one who made it down this far. He then decided he wanted to lay out naked as well. So he slowly undid the laces at his waist. Once his swim suit was loose, he slowly worked it down his legs. He felt an uneasiness as the sun touched his ball sack. His cock stiffened a little as it too was exposed to the open air.

He got nervous because of his half mast. He turned onto his belly and laid there for a few moments to hide it. After about 10 minutes or so, it had become soft once again. Todd started to feel very comfortable. He laid his head back and closed his eyes.

A cough woke Todd. He had fallen asleep. “Shit! I am going to be so sun burned!” thought Todd. He rubbed the sleep from his eyes and noticed he was no longer the only one around. About six or seven others were camped out near him. He felt strange. He had never been outdoors and naked in front of strangers. He covered his penis with his hand and looked to see if anyone was staring at him. It didn’t seem to be that way. Todd wasn’t ugly by any means, typical 28 year old. He was 6 foot tall and 165lbs. His build was slender. He had a light amount of chest hair that he kept trimmed and a small, maintained line of pubic hair above his 4inch flaccid, uncut dick. He couldn’t help his bashfulness so he turned onto his stomach.

Now facing away from the sea as he turned onto his stomach, he looked straight at a gentleman about four feet away from him. The man smiled at Todd. “About time you woke up and turned over!” He said to Todd with a light laugh.

Todd smirked and said “I sure didn’t mean to fall asleep. I can already feel the burn starting.”

The gentleman looked to be in his late 50s or early 60s. He had thin, gray hair and a larger belly. Todd caught more than a glimpse of the man because he was also nude and facing directly at him. Under his belly, he had a small dick. His balls had to be twice the size of his flaccid head. He noticed that Todd had been staring a bit. He winked and Todd caught himself staring as well. Todd quickly looked at the ground and off into space to play off the fact he was staring at this man’s naked body.

“You’re going to need some aloe on that sun burn or it’s going to really hurt!” said the man to Todd.

Todd responded, still looking at the sand “Yea, but I didn’t bring any with me. I’ll have to go out later and get some.”

“I have some in my room. It’s right here behind us!” The man pointed back to the row of small vacation condos. “Come on, I’ll grab some for you.”

Todd didn’t know if he should stand up just yet but the man was already making his way back. He stood up slowly and grabbed his towel, dragging it on the ground but conveniently in front of him to reserve some modesty. He had to walk by some beach grass to get to the back door of the man’s condo. He waited outside, however. He did not want to enter a stranger’s condo at all.

The man, still completely naked, walked out with a green bottle of aloe. He looked at Todd, who was now slightly shaded by a palm tree, and shook his head. “You’re very red. Have a seat on your towel.”

Todd laid the towel down right there in the sand behind the man’s condo and instead of sitting, he laid on his stomach. He wanted to hide his nudity and felt much more comfortable with letting the man see only his ass. The man had already squirted a decent amount of aloe onto his hand and touched it to Todd’s shoulder. The aloe was cold on his skin and made him get goosebumps.

“Cold huh?” said the man, noticing the small bumps covering Todd’s back.

“Yea, I wasn’t expecting that just yet!” Todd replied quickly.

The man continued to massage the aloe into his back making his way down and pulling his hands off his body just before Todd’s ass. Just a second later, the man swung his leg over Todd’s behind and straddled him.

“Sorry, I just need a better position if you’re going to lay down like that.” He said to Todd.

“Uhh, it’s ok.” Said Todd. He felt the man’s weight pressing down on his gluts. Todd noticed how he could feel the man’s ball sack against his ass cheeks. Then again, they were at a clothing optional beach so there wasn’t to say this wasn’t completely out of the ordinary.

Todd also felt how the man’s dick head was sitting right at his butt crack. The softness of the man’s flaccid cock pushing against his butt crack felt squishy. He felt a little dampness where the man’s dick head rested and thought to himself “is that sweat or precum?” The thought made him stiffen a little. Luckily, being on his stomach, he easily hid the slight arousal.

“Do you mind if I rub some of this on your legs? You look burned all over.” The man asked Todd.

“Sure, go right ahead.” Todd answered.

The man slid off of Todd’s behind and gently pulled apart his legs slightly so he could sit kneeled between his legs. He massaged the aloe in slowly on each side. He worked his way down Todd’s quads all the way to each toe. When working back up Todd’s leg, he rubbed a small amount of aloe onto Todd’s butt. The man was being quite thorough and as he rubbed Todd’s first butt cheek, he grazed the tip of Todd’s cock, which was poking out underneath him.

This sent a shiver through Todd. The man had just touched his dick. He stiffened even harder but the man seemed not to notice. He turned to Todd’s other leg and did the same downward massage to his toes. He made his way back up Todd’s other leg and up to his butt. As he massaged the aloe into the other side of Todd’s butt, he grazed the tip of his cock once again. This time,  a string of precum had leaked out of Todd’s cock and the man had touched it. As he pulled away, the string lengthened and when it broke, it splattered back onto Todd’s ass crack. He could tell that his ass crack was quite wet from the man sitting on him before and now this small bit of precum.

He hoped that the man didn’t notice his now raging boner. The man kept rubbing aloe into his legs and he seemed to become a little more touchy feely as he neared his ass. Now, as he made his way over Todd’s butt, he let one finger slide through Todd’s butt crack and lightly pass over Todd’s hole. Todd writhed and let out a slight moan. There was no hiding the excitement Todd was experiencing any longer.

“Hmmm seems like you’re really enjoying this.” The man said.

“I’m so sorry, it’s my first time being naked in public in front of people and…”

“Don’t worry.” The man interrupted Todd. “I’m enjoying this view I’ve had.”

The man put a hand on each butt cheek and spread open his crack, exposing Todd’s hole. He leaned over and lightly blew a cool breeze against Todd’s hole. This drove Todd crazy. He moaned a bit harder and the gentleman went for it. He stuck his tongue right onto Todd’s hole and lapped across it. Todd was getting his ass eaten out right there in the sand. He quickly looked around to see if anyone was around to see but the small bit of beach grass separated them from the rest of the public.

Todd lifted his ass slightly to give a better angle to the man who was eating him out quite attentively. The man pulled away from his hole and ran his tongue across Todd’s dangling balls. He reached around and pulled back Todd’s cock and took the end into his mouth and sucked the end, licking off any leaking precum.

Todd was on his knees and elbows now, getting blown by the larger, old man. He looked behind him and the man’s small dick was now a thick, beer can stiffy. His circumcised penis was glistening in the sun as his exposed head leaked a small drop of precum as well. The man reached down on his own cock and stroked it while Todd’s dick was still being worked in and out of his mouth.

Then the old man got up on his knees and spat down on Todd’s already wet hole. The saliva mixed with the precum that had been leaked onto his hole and the man ran his finger over the entrance of his hole. He pushed with his finger and entered just to play and tease a bit. He then poked and prodded Todd’s hole in a teasing manner with his index and middle finger. Once the fingers had been slipping and sliding across the wet asshole, he pushed them in. Todd gasped and felt as the man entered his two fingers in to the knuckle. The man pulled his fingers in and out and in and out until he felt Todd’s hole was adequately lubed up from inside and out.

He pulled his fingers out and Todd no longer felt the man’s presence. He looked behind himself and the man was stroking his own hard cock just a few feet behind him. He got back onto his knees and pushed his dick head into Todd’s ass crack. It met with Todd’s hole and sat there. Todd felt the warmth of the cock head and suddenly he felt the pressure of it being pushed against him.

Todd breathed outward and relaxed to let his hole swallow the head of the intruding penis. The man groaned as he slid into Todd’s ass. He pulled back and when he pushed back into Todd’s ass, he slowly worked the rest of his cock until Todd was taking his whole member. Todd felt his hole stretch. This man was the size of a Budweiser can and he didn’t know how much he could take.

The man pushed in and out and his big, bull balls slapped Todd’s taint as he pushed his whole shaft into him. Todd angled his ass upward allowing him to take in the cock with ease. This same angled matched well with the curve and size of the old man’s cock. It rubbed against Todd’s prostate as he slid in and out. The old man reached down and stroked Todd’s cock as he fucked his ass and Todd couldn’t take it. Todd shouted in orgasmic joy as his cock started to pulse and shoot stream after stream of hot cum. His first shot of sperm flew by the towel and into the sand. As Todd’s cock pulsed out all the cum in his balls, his ass tightened around the old man’s cock.

“Oh fuck, that’s good.” The man felt Todd’s ass tighten around his beer can cock and he slapped Todd’s ass as he fucked him hard.

Suddenly, the old man grabbed Todd’s ass cheeks and slammed into Todd unleashing his orgasm. His huge, dangling balls had tightened up close to his body, ready to ejaculate all their contents. His member, deep in Todd, began to pulsate and shoot rope after rope of thick, sticky cum.

Todd felt the old man pulse inside him. His large belly over Todd’s back as the man leaned forward, gasping as he unloaded.

“Fuck, that was good.” The old man was still leaning over Todd. His cock slowly deflated and slipped out of Todd’s cum-filled ass.

Todd got up and looked at the man. “Thanks. That was really unexpected. How long are you staying in town?”

“About a week longer.” The old man replied to Todd.

“oh good, me too. I gotta run but I will be looking for you.” Todd said to him, as he grabbed his towel.

Todd headed down the beach, towel and swimsuit in hand. When he made it back to their original spot on the beach his friends whistled when they saw him.

“Hey! Looks like you are fitting in really well!” Randy shouted to Todd.

“Yea, who knew you’d be the one to run around naked” jeered Greg. “Where were you, by the way?”

“Oh, just walking.” Todd replied. He kept his back to his friends. He felt a bit of cum ooze from his hole and onto the underside of his ass cheek.

The three smiled and continued laying out in the sun. This was going to be a good week.