Sailing Away

After a beautiful day at sea, the boys all go ashore to check out the quaint little town. Steffen runs into a friend, who runs the piercing shop. With a new PA inserted, Matthew and the family play a game of truth or dare after dinner about the sailboat.

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  • 16 Min Read

The sails were full as soon as we left the little cove where we spent the last night.  Steffen was behind the wheel, naked with his cock swinging between his legs as his sarong stayed below.  It was another beautiful day for sailing as we cut through the baby blue waters of the Mediterranean.  We were all up on deck, drinking beers, listening to music, just enjoying the day of freedom. 

“Matthew, do you want to see if you can sail.”  Steffen asked him.

“Sure!” Matthew said as he got up off the deck and headed back to the cockpit. 

I watched as Steffen gave him pointers on how the wind affected the sails and how to steer the boat according to the wind. And Matthew was picking up on it quickly, so much that Steffen left him alone for a few minutes while he went below and got us all another beer.  

When he came back up, he was quite impressed with Matthew’s navigation and handling of the sailboat. 

“You’re doing a great Job Matthew; now do you think you can hold this course for about 45 minutes?”  Steffen asked.

“Sure, not a problem.  I’m loving it.”  Matthew said as he stood behind the wheel watching the boat soar. 

“Good, your father and I will be right up on the bow if you need us.”  Steffen said as he took my father by the hand and lead him forward. 

I sat in the back with Matthew mesmerized by his cock and balls swing between his legs as the boat rocked through the water.  My cock had been hard for hours just watching him, and if I didn’t cum soon, I was going to start spewing cum without even toughing myself. 

“Hey” Matthew said to me bringing me out of my desire for an orgasm

“What?”  I said

“Look” He said motioning his head forward. 

I got up and looked forward.  Dad and Steffen were up on the bow, I could see dad lying on is back with Steffen atop of him.  You could see dad’s hands on Steffen’s ass as he was moving up and down on dad’s cock. 

“They’re fucking.”  Matthew whispered. 

“I know, and I’m jealous, I want to get fucked too.”  I said looking down at my hard leaking cock. 

“Is that why you’ve been hard for the past hour?”  Matthew asked.

“Duh. Can’t you just tie something to the wheel for 5 minutes and fuck me?”  I begged.   

“No, but I promise when they come back, we’ll go up there, and I’ll fuck you until you beg me to stop.”  Matthew promised. 

“That will be a long fuck.”  I said to my brother with a smile. 

We couldn’t hear dad and Steffen, but we could see everything they were doing.   And it was obvious that Steffen likes to get fucked as much as I do.   He was now on his knees, and dad was behind him, thrusting rapidly into his ass. Fuck I’m horny! 

“Dude, would it help if I let you drink from the tap?”  Matthew said, lifting his cock up with his right hand.

“Oh, fuck yea.”  I said as he turned slightly, and I moved by the wheel and got on my knees. 

His piss was hot and mild due to the beers we’d been drinking.  But it was coming from his cock, and I wanted a cock anyway I could get it right now.  So, I stayed on my knees and drank every bit of piss his cock could spew into my mouth as he continued to sail us to the next port.  

“Does that taste good?”  I heard my father say as I was gulping down the last of Matthew’s warm nectar.  And I wasn’t about to pull away until I swallowed the last of it.   So, I just kept my mouth attached to Matthew’s cock until his stream of piss dwindled to a dribble.  

“Ahhhhhhh, yes it was delicious.  And how was the view from the bow?”  I asked as I got off my knees, noticing my father’s rather plump softening cock. 

“Wow Matthew I am quite impressed with your sailing abilities.  We are directly on course and making good time.  I think I just found myself a first mate.”  Steffen said as he put his arm around Matthew’s neck and pulled him in for a kiss on the cheek. 

“This is fun, I really enjoy sailing.”  Matthew said. 

“Well anytime.  Why don’t I give you a break now, it looks like Mikey needs some attention.”  Steffen look down as did my father and saw my towering cock that was completely coated in slick, gooey pre-cum.

Matthew grabbed my hand and pulled me up to the bow and laid me on his back.  Quickly Matthew shoved his cock deep inside his ass with one thrust of his hips.  I moaned loudly in extasy as he began to pump his ass, with my legs up over his shoulders, fucking me on deck in front of our father and his boyfriend, or should I say fiancé.

“Oh, yea fuck me, fuck hard Matthew, just keep your cock deep inside me……oh fuck yea!”  I moaned as my brother fucked me like he always does.  

He came twice inside me up on the bow as we fucked for 20 minutes or more.  My cock shot off 4 times and I was coved in cum as we walked back to the cockpit. 

“Feeling better Mikey?” Dad asked as he sat next to Steffen who was still behind the wheel. 

As the island of Paxos came into view Steffen started to prepare the boat.  Matthew and I helped with the sails as dad got the lines and fenders ready for the dock.  And just before we were about to enter the harbor Steffen asked me to get his sarong, and for us to put ours on as well, or at least a pair of shorts.  

I came up on deck with everyone’s sarong, so by the time we got to the dock, our asses were covered.  Matthew and I folder ours in half, making for a mini sarong which got a look from Steffen, but he never said anything. 

With the boat secured on the dock, we all helped with the washdown.  Steffen and dad did the deck and the hull, Matthew and I cleaned up the galley and down below. 

“Who’s ready to go ashore?’  Steffen asked as he poked his head into the galley. 

“We’re done down here, let’s go.”  I said. 

“Matthew were you serious about wanting to get a prince albert?”  Steffen asked

“Yes, is there a place on this island to get one done.”  Matthew asked excitedly. 

“Actually, I got mine pierced here, and I’m sure the shop is still open.” Steffen said as he walked down into the galley

“Can I see yours again?” Matthew asked shyly.

“Sure.” Steffen said as he unwrapped his sarong exposing his long hanging cock with the large, heavy metal ring dangling off the end.  

“Can I touch it?”  Matthew said as he reached out

“Sure.”   Steffen laughed. “Just don’t get me to excited, I don’t want to be walking around town with a tented sarong.” 

“Wow….”  Matthew whispered as got on his knees to get a better look and manhandled Steffen’s cock head.

“Will I have to get dad’s permission?”  Matthew asked Steffen.

“Well of course, but it’s not necessary in Greece as long as you’re at least 15 they consider you an adult.  It’s not like the States“ Steffen explained as Matthew got off his knees and stood up.  “Same with sex, the consenting again in Greece is 15.” 

“Cool I can’t wait. Can we do it today?”  Matthew asked

“Can we do what today?”  My father asked as he came down into the galley. 

“Matthew wants to get a PA, and I told him that there’s a place on the island that will do that for him.”  Steffen explained. 

“You really want one Matthew?”  Dad asked.

“So much they are way cool.”  Matthew said

The town was crowded, but mostly with locals.  The tourists were few and far between.  Steffen asked us to wear our sarongs, but he said since it was so hot, we didn’t have to wear shirts.  So, the 4 of us went ashore, wearing only sarongs and flip-flops to check out the port. 

Steffen was quite well known and popular on the island, as we soon found out. Some of them even knew dad.   The town was very friendly, and we got quite a few second looks from guys and girls as we walked around town half naked. 

“Okay are you ready to get your prince albert?”  Steffen asked as we started to walk up this little cobble stone lane. 

“Yea, I think so.”  Matthew answered feeling a little bit apprehensive about have a ring pushed through the head of his cock

We all walked into this little shop with a small showroom in front, and then an opening to the back with a curtain covering the door.  The bell above the door announced our arrival. 

“I’ll be right with you.”  We heard a man say in a deep Irish accent.

To the right was a small display case of different types of piercings.  Matthew and Steffen were looking at the PA assortment of rings, while dad and I just looked the case over. 

“Now keep it clean and used the salt rinse twice a day for a week.”  We heard the Irish guy say as he walked out of the back area with a really hot looking boy about my age. 

“Thank you so much, I love it.” The kid said as he looked down at the silver ring hanging from his left nipple.

“Now what can I do……oh my god, Steffen!” The shopkeeper said  

“Ryan, hey mate.”  Steffen said when he saw his friend and they both hugged, and cheek kissed.  “I thought you left the island.” 

“I did, but it’s to magical to stay away.”  Ryan said

“Don’t I know it.  Last time I saw you, you were in a sling at that underground place in London with a lineup of guys waiting to take their turn.” Steffen said

“Oh, that was a wild night.  I remember seeing you in a room…….” Ryan started to say until Steffen put his hand over Ryan’s mouth. 

“Some things are best kept as memories and not spoken of again.”  Steffen said and they both agreed and laughed. 

Ryan looked at all of us, and Steffen introduced us to his Irish friend.  “So, what can I do for you all.”  He asked. 

“My young friend here would like a prince albert.”  Steffen said as he put his arm around Matthew’s shoulders. 

“Okay, great have you pick out a ring.”  Ryan asked. 

Matthew walked over to the display case and looked again.  There was quite an assortment of sizes and thicknesses.  He asked to look at a few up close, so Ryan took them out of the case. 

“Do you mind if I have a look at your cock, it will decide the gauge we should use for you.”  Ryan said.

Matthew never had a problem showing anyone his dick, so right there in the show room of the store he pulled off his sarong and stood there naked.  As Ryan took his cock in his hand to fit the size. 

“He’s got a nice sized cock; we could go with a 10 or even an 8-gauge ring I think 6 would be too heavy a look for a boy of his age.”  Ryan said to Steffen. 

“Yea, I think he should start with a 10, and if he wants to stretch it later, and can always do that.”  Steffen said, and then they both looked at Matthew. 

“So, this is the one you think?” Matthew said as he picked up the 10-gauge horseshoe piercing and looked it over.  It was the same style that Steffen sported, however Steffen had a larger 6-gauge piercing hanging from his cock. 

“Can I see yours again Steffen?”  Matthew asked. 

Again, right there in the store front, Steffen released his sarong and let it drop to the floor. 

“Well, hello old friend.”  Ryan said as he looked hungerly at Steffen’s soft cock. 

“His is too thick for you right now, but if you want in a few years, I think that size would look good on you.”  Ryan said as he took Steffen’s cock in his hands.  “Oh, the fun times we’ve had!”  Ryan said and then kissed the head of Steffen’s cock. 

“Do you have any questions?”  Ryan asked Matthew. 

“One for sure, how long before I can fuck someone?”  Matthew asked bluntly and then looked at me. 

“That’s the best thing about PA’s, they are very quick to heal, today’s Tuesday, you can fuck on Friday without and problems.”  Ryan said

“Okay let’s do it.”  Matthew said

Everyone went into the back, but I really didn’t want to watch Matthew get a needle shoved through his cock, so I kept looking at the items and thought of the boy who had just got his nipple pierced. And I  fascinated by the looked.  But I would get both nipples done if dad would let me.

It wasn’t 10 minutes before they were done, and they all came back out.

“Did it hurt?’ I asked Matthew immediately.

“Not really.  It’s a little bit sore now, but they said that would only last for a few hours.”  Matthew told me. 

“Can I see it?”  I asked, so he pulled up his sarong and showed me his new piercing. “That is so cool, I love it.” 

“Yea, I have to agree, that looks good on you Matthew.” Dad said and Steffen and Ryan both agreed. 

“Dad, I want to get nipple rings.  Just the small ones but I think they look hot.”  I told my dad.

He looked at me, then at Steffen who just shrugged his shoulders.  He then looked at Ryan for an answer.

“Yea, he’s old enough and it wouldn’t be a bad look for him. And he’s got nice perky nipples which will hold them nicely.” Ryan said as he took both in his hand and twisted them softly. “I wouldn’t go with anything too big, but as he said, he likes the small ones.  I think if we went with a 14 gauge it would be a good look for him.”   

“You really want to do this?”  Dad asked me. 

“Yea, I really do.”  I said and by the time we left Ryan’s story Matthew had a new PA and I had both my nipples pierced. 

Ryan decided to close the shop and joined us for lunch.  I loved the feeling of my new nipple rings and since I wasn’t wearing a shirt it was cool that everyone could see them.  Ryan recommended a small local taverna for lunch which was right around the corner from his shop.  

“So, what are you guys doing sailing the Med, sounds like a great adventure.”  Ryan said.  “I’m quite envious of you guys.” 

“We’ve got about 5 more Islands were going to see before we must head back to Athens. Should take us about 3 weeks or so.”  Steffen said. 

“God I’d love to tag along; Just for a few days, do you don’t need another crew member?”  Ryan said laughingly. 

“That would be so cool if Ryan came with us.”  Matthew said, and I agreed.

‘He was really fucking hot, with his shaved head, and a great body.  I wonder if he’s shaved all over or just his head, and what about his cock. Oh my god his cock, I would love to see his cock.  I bet it’s uncut and huge. And how many piercings does he have, and where!’ I thought as my own dick started to get hard under my sarong. 

“Sure, we leave tomorrow morning at sunrise” I heard Steffen saying…what, wait I was lost in thought, was Ryan coming with us?

“Great I’ll get my gear ready and meet you there in the morning.  I am assuming the dress is the same as our last sail.”  Ryan said with a smile. 

“Yea, not much has changed.”  Steffen said. 

That night was tame for me and Matthew, with our new piercings we had to be good.  So, after we got back from dinner, we changed back into our sarongs and sat out on the deck and got drunk with dad and Steffen.  We were having a great time and then Matthew suggested we play truth or dare. 

“Okay sounds like fun, I guess.”  Steffen said. “Who goes first?” 

“Well since it’s your boat, we’ll give you the honors.”  Matthew said “You know how to play right?  

“No problem, so my first truth or dare will be for you.” Steffen said looking at Matthew. 

“Well to make it interesting I will take a dare.”  He said as both dad and I looked at him like he was crazy. 

“Great!” Steffen said and then thought for a minute. “Ok let’s make this an easy one.  I need you to go get us some ice from that ice machine on the shore, just tell the harbor master to put it on our bill.”  And he pointed to the machine. “Naked and remember not running on the docks.”  

Matthew got up, took a big swig of his beer, and released his sarong.  I watched it fall to the deck, and he stood there so we all could check out his cock, with is new PA hanging off the head.  Dad even whistled.

We all watched him walk slowly along the dock, then up the ramp to the dock house.  He got a lot of looks from other people on their boat, and a few people on shore as he walked to the harbor master’s house.  And within 5 minutes he was back on the boat with a bag of ice.   We all clapped when he boarded the boat.  

“My turn, yes!”  Matthew said. 

“Dad, truth or dare.”  Matthew said sitting there naked not bothering with his sarong. 

“I’ll do a truth?”  he said

“Dad, have you ever watched Mikey and I having sex?”  Matthew asked.  “And if so, when and where, and did you get off watching us.” 

“ahhh well aaahhh” dad stammered

“Come on Mark tell us all the truth.”  Steffen said putting his hand on dad’s leg.  

“Okay but this stays between us.  It had to be about 3 or maybe 4 years ago.  I had just gotten home from a business trip, well at least that’s what I called it, when I was actually sailing with Steffen.” He said and leaned over a kissed Steffen on the lips.  “Anyway, I walked into the house, and no one was home, but then I saw the two of you in the pool.  I didn’t think much of it until Matthew got out and he was naked.  You followed him out of the water, and you were also naked, and had a very big hard -on.  I watched as your little bother got down on his knees and took your cock in his mouth.  You stood there, with a wild look on your face as you pushed his head into your crotch.”  Dad told us.

“Wow dad!”  I said.

“Yea, it was pretty wild, but I still stood there as Matthew brought you over to the lounge chair and you laid down on your stomach.  He spit on his hand and lube up his hard dick and then laid down on top of you.  I was about to go out there to stop you both, but I saw that you were enjoying it so much.  That’s when it changed for me, I wasn’t watching my sons have sex, I was watching two hot kids fuck.   So, like any normal gay man I pulled my now hard cock out of my pants and jerked off watching you fuck your brother.  It was quite obvious that Mikey like to get fucked, you fucked him every which way that night, and I watched you fuck him for almost an hour.  I think I came 3 times.”  Dad said as he finished the truth.

“Wow!”  I said as I looked around at all the tented sarongs, and Matthew’s towering cock with his PA dangling from the head. Having never bothered to cover back up. 

“Dad, it’s your turn.”  Matthew said. 

“Steffen, truth or dare?”  Dad asked.

“Truth” Steffen answered.

“Are you hoping to have sex with Ryan on this trip?”  Dad asked. 

“I’m hoping we all will.” Steffen answered right away. 

It was Steffen’s turn, and he looked at me.  “Truth or Dare” 

“Dare!”  I said brazenly. 

“Drink my piss straight from my cock.”  Steffen said as he got up and pulled off his sarong. 

“Steffen!”  My father protested. 

I looked at him, and then at my dad and then at Steffen’s cock with his huge PA.  I was on my knees in a second, as I reached for his cock and laid it in my mouth as my father watched in awe.  His piss stream began fast, and I quickly wrapped my lips tight around the head of his cock with the PA inside my mouth.  Oh my god it tasted so good right from his cock, much better than the other night when he gave it to me in a bottle.  His stream was so hard at times, I had to use my mouth as a reservoir until I was able to swallow what I could and then drink what I had stored in my mouth. But I had sucked down all his piss until his bladder was finally empty. 

“Oh, that was good.”  I said as I got up off my knees. 

“Where the hell did you learn to drink piss.”  My dad said, and I looked over at Matthew.

“Don’t blame me, I just let you drink mine.  You’re the one always begging for it.”  Matthew said.

“True, I love to drink piss dad.”  I said

“Do you want to drink mine?”  He asked

“Fuck yea dad, seriously?” I asked excitedly.  

He got up and dropped his sarong as well. I again got on my knees and opened my mouth as my father aimed his cock and began to piss into my mouth.  It was a fun and wet night for sure. 

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