Captured By Gay Pirates

By: Mr. Max


Erotica Story Genres:


Edwin yawned as he looked out from the crow’s nest over the open water. He was tired of the sea. Tired of his life in the British navy. Because he was a fourth son, he had little choice but to be gainfully employed as his brother would inherit the title from his father. He sometimes wondered why his parents had bothered to sire children beyond the usual heir and a spare. But, then, his parents had probably just enjoyed fucking. It wasn’t something he really could understand. He had been to brothels and been balls deep in maids before. He had cum in them or on them, depending on the establishment’s rules, and yet, he had found it more messy than pleasurable. If it was an acquired taste, he didn’t think he would ever really enjoy it as his co-crew seemed to. Every time their ship docked the other men rushed off to the nearest bar and brothel. He was more than happy to stay behind and guard the deck.

“I think there is a ship in the distance. Do you see that?” his partner in the crows nest asked.

It was in fact, a ship flying a skull and crossbones flag.

Though Edwin’s Captain tried valiantly to outmaneuver it, they were soon overrun.

Edwin pulled his rapier from it’s sheath. He knocked two pirates off deck before meeting another one who crossed swords with him. The pirate across from him was broad shouldered and his bare chest showed through the rips in his shirt. The pirate wore a black bandana and an eye patch. And, he met Edwin’s sword with his own. The two men exchanged blows, but, the pirate was stronger and faster. With a flick of the pirate’s wrist, Edwin was disarmed. Edwin dropped to his knees before the pirate, closed his eyes, bowed his head, and waited to die. Instead, he felt rough hands on him and a rope binding him in a hog tie position. He opened his eyes but suddenly, he was blindfolded and he felt himself being carried. He was being taken prisoner!


Isn't it time to treat yourself?

Lelo Ora 2

The World’s Most Sophisticated Oral Sex Simulator


Edwin felt himself being tossed onto a bed and then his blindfold was removed. The pirate who had bested him was standing strong, looking down at him.

“Please… I don’t know anything. Torturing me would be fruitless. Please, have mercy and just kill me instead,” Edwin said.

“Our parents would never forgive me if I ended your life,” a familiar voice said.

“Reg?” Edwin asked in astonishment. Reginald, Reg, was his milk brother. He and Reg had nursed side by side at the same tit as babies. Edwin’s mother hadn’t believed in nursing her own children so she had hired a wet nurse. Then, when the boys were old enough to be off the tit, Reg and his mother had continued to live with them as servants until Edwin had left for the navy. He had thought Reg and his mother would still have been in his parents’ employment, though it had been years since Edwin had been home.

“The one and only,” he said removing his bandana and eye patch. His patched eye wasn’t damaged as Edwin had feared but it was still the mismatched green to his other blue eye. A feature, Edwin realized, that would have made Reg stand out. “You’re lucky it was me who got to you first. The captain doesn’t usually take captives. Too many mouths to feed and coffers to share plunder with. But, I’m his first mate and I expect he’ll understand. Especially once you’ve spent some time in his bed.”

“Bed?” Edwin asked. Now, he was really confused.

“Come on Edwin. Haven’t you realized yet that the ladies don’t do anything for you. A bit of pussy will do in a scrape, but, you are like me. Our cocks can’t fully get hard for a chit. Now, a nice cock on the other hand, that is a different story entirely.”

“I don’t understand…”

“You will brother. You will.”

Reg dressed Edwin up in clothes from his own bureau though they fit him loosely, and they made their way to the Captain’s quarters that evening as the moon was shining over the ship. The captain had a lamp lit but the room was still dim when they entered.

“Windham, this is my milk brother, Edwin,” Reg said. To Edwin’s surprise, the Captain didn’t look a day over thirty. He was muscled and broad, much like Reg was.

While Reg had brown hair, Windham had hair that was a sandy blond and blue eyes that sparkled in the lamplight.

“A little thin for my taste,” Windham said thoughtfully rubbing the stubble on his chin.

“A few months on this ship will muscle him up,” Reg said.


Let's try something new, shall we?

Lelo Ora 2

The World’s Most Sophisticated Oral Sex Simulator


“And you are sure he is one of our kind?” Windham asked.

“I’ve known since we were boys that he didn’t want a thing to do with any woman. It’s blokes he likes. Even if he doesn’t know it yet,” Reg said with a smile.

Could they be right? Edwin wondered. He had never really thought to try fucking a man. That wasn’t how he had been raised. It had never occurred to him that the reason he found sex with women so dull was that what he really wanted was to fuck another man.

“Well, take off those clothes and let’s see if what you have is worth the cost of feeding you,” Windham said. Edwin gulped but did as he was asked and disrobed. He stood naked before Windham and Reg and to his surprise, his cock grew to it’s full length as they stared at his nakedness.

“Not bad,” Windham said with a nod. “Not bad at all.”

Reg stepped forward and put his hand on Edwin’s cock. It sent a burning wave of heat through Edwin’s body and for the first time in his life, he truly felt desire.

“Well, where do you think he will fit best?” Windham asked.

“I say we put him in the middle and see what he likes,” Reg said with a wicked smile.

“Alright then,” Windham agreed as he unfastened the belt to his pants.

Soon, both men were naked around him and Edwin’s cock felt as if it might explode right there. Of course, he had seen naked men before. But, those men had not been ones who were planning to do dirty things to him. Things he wanted them to do.

Reg dropped to his knees before Edwin and bent forward to take Edwin’s cock into his warm wet mouth. Edwin let out a groan as his cock was encompassed in the heat of it. No brothel maid’s mouth could compare to Reg’s who skillfully began to take Edwin deep into his throat then withdraw him until only the very tip of his cock remained between his lips.

Edwin felt Windham step behind him and he felt the tip of his cock press against his ass cheek.

He looked back at Windham with anxiety and anticipation as he watched Windham take a bottle of olive oil and pour it on his cock. The lamplight reflected off the oil, giving his cock a shiny sheen.

Then, he felt Windham grab his ass cheeks and push them apart. He felt the cock at the entrance of his ass. Windham pushed it into him slowly. It filled him and stretched him. At first, Edwin wasn’t sure what he was supposed to think of it all. Then, Windham withdrew his cock and thrust it forcefully into Edwin’s ass. This time, Edwin felt a wave of pleasure flow like an electric shock through his balls and his cock. It made the feel of Reg’s mouth fucking him with his mouth all the more pleasurable. He reached out and grabbed Reg’s hair. Holding his face close as he plunged Edwin’s cock down his throat and then withdrew it.

Windham began thrusting his cock in Edwin’s ass to the same rhythm as Reg was taking him in his mouth.

Windham’s hands were on Edwin’s hips as he thrust deeply into him. Edwin could hear Windham panting and he realized he was panting too. His skin against Windham’s was covered in a thin film of sweat.

Then, he heard Windham groaning and he knew that Windham was close. He didn’t want it all to stop. It felt so good. So much better than any whore he had ever fucked in any brothel.

Reg sped up at the same time Windham did and Edwin thought he might just leave his body with the intensity of the pleasure. He moaned loudly and leaned into Windham who was riding his ass, hard. Then, he felt his balls contract and a wave of pleasure ran over him and he let it all go. The room spun and he closed his eyes as he lost himself in the pleasure as his cock pulsated and cum spilled from it and into Reg’s mouth. As Edwin started to come back to himself he heard Windham grunt and he felt Windham’s cock in his ass pulsate and he could feel the hot cum filling his ass.

Windham pulled out of him and Edwin felt uncomfortably empty. He wanted his ass filled again.


Ready to upgrade your pleasure?

Lelo Ora 2

The World’s Most Sophisticated Oral Sex Simulator


Reg was staring at him and smiling.

“See, my brother, I told you,” Reg said.

“You were right,” Edwin panted. To his surprise, his cock was getting hard again. Hard and ready for more.

“Well, you were right about this one,” Windham said with a smile as he reached out to stroke Edwin’s cock. At his touch, Edwin’s cock was again at full attention.

“So, do you want to fuck my ass?” Windham asked. To his surprise, Edwin found that he did want to. Very much.

“And, I will fuck yours,” Reg said with a smile.

Edwin was ready and filled with desire. Reg handed him the olive oil and Edwin covered his cock in it.

“Is that enough?” he asked Windham.

“Always put on as much as you think you will need, and then add just a little more,” Windham said bracing himself against the nearby bureau and leaning over it slightly.

Edwin positioned himself behind Windham and spread his ass cheeks. Then, he positioned himself at Windham’s asshole and pushed inside.

Windham let out a groan.

“Oh God, what a nice big cock you have,” Windham said with a pant.

Edwin could hear Reg covering his cock with the olive oil. Then, Reg was behind him. Then, inside him.

Reg thrust forward and then Edwin thrust forward as well. His ass was filled with Reg’s cock and his cock was filling Windham to his balls. He watched as Windham grabbed his own cock and began to pump it roughly with his hands while Reg and Edwin thrust together in unison with Reg’s cock withdrawing from Edwin’s ass at the same time that Edwin was withdrawing his cock from Windham’s ass. Then, he would thrust forward to fill up Windham’s ass just as Reg’s thick hard cock filled him.

Time seemed to stop and Edwin let himself get lost in the sensation of pleasure.

Then, he heard Reg moan and stiffen against his back and he knew Reg was cumming in his ass. The thought made Edwin so aroused that he felt the wave of pleasure overtake him and his own cock began to pulse and spill.

He heard Windham groan and he watched thick white cum squirt from Windham’s cock and onto the floor in front of them.

Slowly, Reg withdrew his cock and then Edwin withdrew his.

Windham turned to Edwin.

“Get a bucket with some water and get that cleaned up. I make sure my crew have plenty of work to do. You are planning on joining my crew aren’t you? It would be a shame for such a thick cock and tight ass to have to walk the plank.”

“Aye Aye Captain,” Edwin said, giving Windham a salute.