Todd's Caribbean Vacation

The week in the Caribbean for Todd went so nicely. He was enjoying the days in the sun and sipping pina coladas at every chance he had. His two best friends, Greg and Randy, also became comfortable with the nude beach behind their condo they had rented and the boys spent most of their time naked on the shore.

Todd, in his late 20s, had a slender build and lightly fury chest. He didn’t shave his pubes down and his hair got even thicker in his ass crack. His dick hung soft at 4 inches. His foreskin hung over the head of his penis, just barely covering it all.

Greg and Randy both had similar body builds. The boys were also in their late 20s and about 250 pounds. Greg’s dick was smaller than Randy’s. It was hidden under a small bit of fat when soft. Randy was definitely a shower and not a grower. Randy’s cock hung at about 6.5 inches and had a loose circumcision. Whatever was left of his foreskin bunched up at the ridge behind his dick head.

The boys all three soaked up the sun and enjoyed the time out together. Todd couldn’t stop thinking of the encounter he had with the old man down the beach on his first day. Every time he thought of that man’s leaking cock teasing his asshole, he stiffened ever so slightly. He had spent all his time on vacation with the other two that he never had a chance to walk down and see if he could find that man again for a quick fuck.

Finally, just before sunset, Todd stood up and decided to take a walk down the beach. The other two wanted to stick behind, so Todd took off down the beach. He kept his sunglasses on so other men couldn’t directly notice that he was definitely looking at all their beautiful packages bouncing back and forth. Todd kept thinking to himself how badly he just wanted to drop everything and move here.

Once out of the busy public beach area, Todd found the small beach front condo where his ass was stretched open by a beer can sized cock. Out on the patio of the condo was the old man and some of his friends. The old man looked over, squinted, and realized who is was. He waved and signaled for Todd to come over.

Todd headed up the sand to the back of the condo to where the men were all sitting around.

“Gentlemen, this is the boy  I was telling you all about from earlier!” The old man said while Todd came closer.

The other men whistled and made small comments of how cute they found Todd. Todd suddenly wasn’t sure if he was comfortable with it all but he laughed a bit nervously and stuck it out.

“How have you been?” the old man asked Todd.

“Oh, just enjoying vacation. You?” he replied.

Todd looked around at the old men. Bears of men they were. One had a thick dick piercing, stretching open his urethra. He fondled his balls in a way older men do when they lounge around. The other had balls bigger than golf balls. They were both clean shaven and kept eyeing Todd.

The men were all talking and getting some conversation going for awhile and finally the older man interrupted.

“Todd, we are having a sort of get together tonight before the others leave for home. Would you like to come? I’d like to invite you as our special guest.”

Todd wasn’t sure what to think. Greg and Randy didn’t have anything planned for them tonight but how was he going to just sneak off to spend an evening with these older men?

Todd thanked them and said it was a possibility he’d stop by but then explained he needed to head back to his friends. The old man winked at Todd as he turned and left.

Todd made it back to the beach where their rental property stood. No one was out any longer because the sun had set. He noticed all the lights were off at the condo where he was staying and wondered if Greg and Randy were out.

“Oh fuck…yea” Todd heard a light moan off to his right side while making his way to the condo entrance. He glanced and made out two figures. He walked slowly over to where he heard the noise. It was blocked by some tall beach grass.

The gasps grew louder and Todd’s curiosity peaked. He squatted down at the beach grass and slowly pulled it apart to see through. It was Greg and Randy! Greg was on his back in the sand with his legs spread open and Randy had his hands pushing Greg’s legs back, pointing Greg’s ass towards Randy.

Todd saw how Randy’s cock pushed into Greg and he was pushing in and out in a rhythmic manner. Todd’s cock started to stir as he saw this. He felt a little weird because he wasn’t sure if he should be watching his two friends fucking. But unless they ran over, they’d never know.

The slaps of Greg’s ass meeting Randy’s hips made a light clapping sound as they picked up speed. Randy reached down and stroked on Greg’s stout cock.

“Oh fuck, you’re gonna make me shoot” Greg exclaimed. Randy let go of Greg’s cock and slowed his thrusts.

“Not just yet. I want you to sit on this and ride me.” Randy said with a dirty grin to his face.

Randy pulled his cock out of Greg’s ass slowly and repositioned himself to lay in the sand. Greg stood over him and began to squat over Randy. Once on top of Randy’s dick, Greg bounced happily on top. Greg’s short penis was hard and bouncing on Randy’s stomach as he took in all of Randy.

“Oh yea, shoot your load all over me as your ride.” Said Randy. Greg’s moans increased and Greg began beating off his dick.

“I’m gonna shoot!” shouted Greg. And Greg slammed his body harder and harder on Randy’s dick and began to shoot cum from his own onto Randy. The first spurt of cum shot Randy right in the chin as the rest covered and soaked Randy’s chest. Greg kept slamming down onto Randy until Randy grabbed Greg’s hips and held him in place and grunted. Randy shot his load deep into Greg and they both laid there in the sand, wet and sticky with each other’s cum.

Todd was so turned on. His cock was rock hard now and he didn’t know what to do. Clearly his friends didn’t want to be bothered so he took the opportunity to head back to the old men’s condo and hang out longer.

His hard boner bounced up and down as he walked the length of the beach back. He hoped it would be completely soft by the time he got back to save himself some embarrassment.

“Hey, you did decide to come!” The old man shouted from a slight distance. About 10 men were all sitting around a bonfire on the beach. All were still naked. Todd took a seat next to the old man around the fire and introduced himself to the others.

“Welcome, Todd.” Said the old man. “We do this every year together and the last day of our vacation we have a small party. We try to invite one person out of our circle of friends to join and be our special guest. I’m so glad it’s you.”

The other men looked over at Todd and nodded in agreement.

“I have to be honest with you, Todd.” The old man started. “I had to tell all my friends of when we first met. Your ass felt so good and when it took in my cock, damn. I’ve been thinking of it all week.”

Todd was not sure if he should be flattered or uncomfortable because this man was talking about fucking his ass in front of all these men.

“Would you mind showing just your hole to my friends? I mean, we are naked to begin with but just a peak at what I got to enter.”

Todd didn’t know what to do. Was he supposed to just stand up and bend over?

“Uhhh, sure?” Todd said.

The man pointed towards a large mattress laying out on the sand off to the side. “Lean over that, it’ll be easier and less awkward.”

Todd made his way to the mattress and bent over. His elbows met the fabric of the mattress and he felt all eyes on him. His cock started to rise a little.

The old man made his way over and slapped an ass cheek. “Look at that beauty, guys!”

Another came over and caressed his other cheek, admiring the hairy hole. Suddenly Todd felt more hands over his ass and he just stood there. The man with the pierced cock got on his knees and stared right at Todd’s hole. He inched closer and licked his tongue across Todd’s asshole. Todd shivered and broke out in goosebumps. The tongue felt so good teasing his hole. The rest of the group came around closer to get a better look.

“Do you mind if they give you a try?” The old man asked Todd.

Todd’s cock was now rock hard and starting to leak precum. He couldn’t think of words to say. He was surprised at what was happening. He shook his head and confirmed he didn’t mind what was happening. In fact, he wanted more.

The old man came and sat in front of Todd’s face where he was bent over. His beer can thick cock was solid and he waved it in front of Todd’s lips.

“Take it in your mouth, Todd.” The old man said. Todd lowered his lips over the head of the man’s penis and slowly swallowed it down.

The man with the pierced cock kept eat out Todd’s ass and the other men around were playing with themselves.

Moans came from everywhere. You couldn’t pinpoint who they came from exactly. Everyone was enjoying themselves.

Then, the man with the pierced cock pulled away and another man stepped in. This time not with his tongue. He pushed his cock into Todd’s hole. It had been a few days since Todd was last fucked by that big beer can cock so he had tightened back up. Todd winced a bit as the cock entered and then he felt the man’s hips at his ass cheeks. He took that man’s cock deep in his ass while he sucked on his old friend.

Another man came up in front of Todd and offered him his cock as well. Todd put his old friend’s cock next to the other man’s and sucked both dick heads. Suddenly he felt a grip tighten around his waist as the man fucking him stiffened and moaned loudly. He felt the pulsing of this man’s cock in his ass. He was unloading inside him. When he finished, he pulled out and moved back. Another man lined up and spit down on his cock. Todd’s ass was already lubed with plenty of spit and one load of cum. The man entered him and thrust hard into him.

That man didn’t last long at all. He groaned and moaned and slapped Todd’s ass as he came inside Todd. When he slipped his cock out of Todd’s ass, a third man came behind and turned Todd over. He pushed Todd’s legs back and pushed hard into Todd’s back entry. His old friend still at Todd’s head, got on his knees and put his cock over Todd’s face. Todd took his old friend’s thick cock in his mouth and his old friend leaned over to take Todd’s exposed cock into his. They 69-ed while the third man fucked Todd’s ass.

Eight more men took their turns fucking Todd in the ass. They alternated between watching the hot scene and playing with themselves and fucking Todd’s ass and mouth. Todd’s ass felt full. He could sense whenever warm cum slid from his asshole down his ass crack as it leaked out. Everyone was spent after unloading in him. Finally, the man with the pierced cock came up to Todd’s ass again. He lowered his face down to his hole and licked at Todd’s opening. Todd couldn’t hold all the cum in him and some leaked out onto the old man’s mouth. He slurped it and enjoyed the taste of cum from 9 other men all mixed together.

He stood up and pushed his thick piercing against Todd’s hole. What a different sensation, Todd thought. The man pushed through Todd’s opening and began fucking him. The ring made a gentle glide inside Todd’s ass and made a textured rubbing against Todd’s prostate as he fucked him.

Todd stiffened even harder and enjoyed every inch and every thrust from this old man. The sensation of his prostate got stronger and stronger. The amount of precum Todd was leaking increased and it was soon flowing almost steadily out of the tip of his cock.

“Fuck I´m going to cum.” Shouted Todd.

The old man thrust harder and harder until the last second. Once Todd’s cock began its initial orgasmic pulse, the old man pulled his cock out of Todd’s ass. He grabbed Todd’s cock and aimed his cum at his own dick. Todd shot rope after rope of sticky, warm cum. It covered the old man’s pierced cock. When Todd’s orgasm subsided, the man reentered Todd’s ass with his cock covered in Todd’s cum and began fucking him hard. The man closed his eyes as he got close and finally unleashed his thick load into Todd as well.

When he pulled his cock out of Todd, all the men around stood in awe. They thanked Todd for their chance to fuck him. Todd couldn’t stand up at first. His whole body was weak. His old man friend helped him up. His asshole felt so full but he didn’t want to let any slip out. He enjoyed the feeling of all the cum in his ass.

He said his goodbyes to the men and decided he better start home. He headed back to the rental property where he and his friends were staying. Still horny from what had just happened, he didn’t walk up to the house just yet. He crouched down on his knees and held his hand to his ass. He let the loads of 10 men slide out of him and cover his hand. When his hand was saturated with all the cum, he brought it to his cock and lubed his dick up with all that semen. He was hard as a rock again and jacked off on the beach. When he was fully satisfied and shot his cum once again, he took a quick dip in the ocean to clean off before returning to the condo.

What a vacation, he thought.