This is the third chapter in the story of life of a cabin boy in the days of pirates.
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Life With the Pirates - 3
When the cook and I had finished cleaning the galley he told me that I was free to go back to the Captain's cabin. As I walked out into the evening air the breeze felt great against my almost completely naked body. It was only nice for a few seconds as the cool wet air started cutting through me and my body began to shiver. The Captain was watching and ordered me to get inside before the sea breeze make me sick.
I hurried into the cabin and was happy to get out of the wind. I had stopped shivering but was having to carefully find my way around the cabin because there were no lanterns lit inside the room. I bumped into the table and chair and finally found the cot and lay down waiting for whatever was to happen next.
The door opened and a little light came through the doorway was the Captain stepped in and then grunted something about not having lighted a lantern. He lit the lantern and then moved over to a table and pulled out some piece of clothing. He tossed it to me and told me to put it on and then to lie on the cot and not say a word. It took me a few seconds to figure out that what he had tossed me was a silk slip that women with money ware underneath their gowns.
I fumbled around and was able to figure out how the slip went on and then pulled my wrap off and lay down. The Captain had pulled all his clothes off and I was able to see that his cock was not hard. He moved to the side of the cot and again told me to not say a word and to do everything I was told.
He leaned over and started kissing my neck and ears. I had never been kissed in this manner and it was sending shivers throughout my body. The Captain had started rubbing his hands on my stomach and chest. The slippery feeling of the silk on my body was giving me a raging hard-on. The Captain continued to kiss my neck and caress my chest for a good five minutes. Then without warning he kissed me full on the mouth and as I opened my mouth he pushed his tongue inside. I had no idea what to do but when he started sucking my tongue out of my mouth I decided to try the same.
The shivers running up and down my body had increased and the silk material was not helping me. I thought that if he didn't stop soon he would find a wet spot where my crotch was located. He pulled his mouth from mine and slipped the shoulder straps of the slip down as he closed his mouth around one of my nipples. I know he had to feel the shivers that went through my body. As he sucked and nipped at one nipple he pinched the other one with his hand. I was starting to moan as his attention to my body had taken all control of it from me.
He reached down and pulled the bottom of the slip above my waist as he pulled my leg up to where he could slip his hand into the crack of my ass. He started applying pressure to my asshole as he continued to work on my nipples. As the tremors ran through my body he would push his finger deeper in my asshole. He was now pushing his finger in and out of my asshole as he rotated from my nipples to my neck and then my mouth. The faster he got with his mouth and tongue the faster he also got with his finger.
I felt as if my body was completely detached from my brain as it started humping and pushing against his finger and mouth. I was about to scream out from all the sexual pressure he had built up in me, when all at once he stopped and rolled over on the cot beside me. He looked at me and told me that I could do whatever I wanted.
I pulled the slip completely off as I spun around and swallowed his cock. I was going at his cock as if it was the last meal I would ever have. As I was bobbing on his cock he had placed his finger back in my asshole and was slowly sliding it in and out. He moaned a few times but I could tell he was holding back. I was pretty sure that he was not going to cum in my mouth and my asshole was really burning for some more attention.
I stood up on my knees and then straddled him as I lowered my ass down onto the head of his cock. There was some pain but again my body had taken over and I was now forcing all of the Captain's cock deep inside me. When it was all inside I started bouncing up and down but this didn't seem to give me the feeling I was looking for. I placed my hands on the Captain's chest and then started pumping my ass up and down as the rest of my body remained as still as possible in that position.
This allowed my prostate to rub against his cock every time I moved up or down. He noticed that I had found the position that I was looking for as he reached up and started pinching my nipples. Each time he pinched I got a surge in my balls and I thought I was about to cum at any moment. He reached down and lifted my cock and balls up off of his pubic hair and started thrusting his cock up at me as I drove down on him. This caused his cock to go even deeper inside me.
Without a warning my cock started shooting cum that was traveling from my cock and landing on the Captain's face. He was still holding my cock and balls up with his hands and it had caused my cum to shoot out at him. When he noticed the raining cum he started pumping even faster into my asshole. He was not trying to cum but to make me cum with more force. When my cock had stopped showering him I figured I would be through but to my surprise the desire to impale myself on his cock was even stronger.
The Captain noticed this and from the look on his face was amazed as well as I was. He let me continue my fucking of his cock as he called for the man standing outside his door. The man came in and for a second just froze as he started watching the action. The Captain told him to go get Old Joe. I didn't know who Old Joe was but I was too busy trying to fuck myself to death on the Captain's cock. Again I was cumming as my cock sprayed my cum all over the Captain's face and chest.
The door opened and an old looking man that I had not seen before walked into the room and shut the door behind him. He moved over to the cot while watching the action between the Captain and myself. The Captain told Old Joe that he was about to cum but he had somehow turned me on and didn't know how to turn me off. He said that when he did cum that Old Joe could take his place and let the boy fuck for as long as he could. While he was telling Old Joe this, Old Joe had leaned over and was licking the cum from the Captain's hand and had managed to suck my cock into his mouth.
This caused my cock to explode again, as so did the Captain. I felt him thrust into me even harder as he was empting all the cum he could from his balls. This caused me to cum again and this time Old Joe sucked all the cum down his throat. I had slowed down a little but was still riding the Captain's cock even though it was beginning to soften. Old Joe removed his pants with one quick flip of his hand and started to lie down next to the Captain. I was not able to see his cock but figured he was at least as large as the Captain was.
The two men pulled me off of the Captain's cock and positioned me over Old Joe. I felt the pressure as his cock started to enter my asshole. I then realized that there was a lot more pressure with Old Joe than there had been with the Captain. As I continued to slide down Old Joe's cock the pressure of my asshole being stretched even more became apparent. I screamed a little as Old Joe pulled my hips down on him as he thrust the last of his cock inside.
There was some pain but the desire to continue to fuck my ass on something was even greater. I started pumping up and down again and that lovely wave of emotion started sweeping my body again as my cock stood up. The Captain had moved to the side and was watching as he grabbed my cock and pointed it toward Old Joe's face. When it erupted most of the cum landed right in Old Joe's mouth as he licked at it and swallowed it down. Watching this only made me pump faster which in turn rubbed my prostate faster.
Old Joe looked over at the Captain and told him that he had found a live one. He said that when the men got restless that he could get me going and probably satisfy the whole crew and still want more. The Captain just nodded his head as he agreed with Old Joe. I was half way listening, as my cock wanted even more relief. This time when I came I all but passed out as the room got dark, but I could still hear Old Joe as he grunted while he pumped his cock inside me.
I blinked my eyes a few times and was able to see the Captain and Old Joe as they both were watching me. Old Joe said he thought that I had probably had all I could take for a while, as he rolled me over and climbed on my back. He started fucking my asshole faster than I thought was possible. I then felt Old Joe's cock swell just before he started cumming inside me. It seemed like his cock would never stop as I could feel the cum leaking out my asshole around the sides of his cock.
Old Joe finally stopped pumping and rested on my back. When he started to pull his cock out I yelled out in pain. It was if his cock was stuck in my asshole and I begged him to let it go soft before he tried to remove it. The Captain and Old Joe both looked down at his cock and noticed that when he tried to pull out, that my asshole was gripping as if it wasn't going to let go. He pushed back into me and said he could wait, but he hoped that my tight hot asshole didn't get him completely hard again.
As he laid there on my ass the Captain and he talked about what had happened. The discussion had centered on the muscles in my ass cramping up around Old Joe's cock and they weren't sure how long it would be before he would be able to remove his cock. I just laid still enjoying the warmth of Old Joe's body lying against my ass and the hot rod of a cock deep inside me. Old Joe tried a couple more times to pull out but the reaction of my ass was the same.
The Captain finally had us slide up on the cot where we could just relax. He found a bottle of wine and started drinking and then laughing at the situation. He started comparing us to a couple of dogs that had gotten tied together. The thought must have been funny to Old Joe as he started laughing along with the Captain. He then told the Captain that he had fucked a lot of men and women along with most animals, but this was the first time he had not been able to leave when he wanted to.
The Captain had moved around to where his cock was right in front of me and I noticed that it had started to grow a little. I leaned forward and sucked his cock into my mouth as Old Joe started telling about some of the wilder fucks he was involved in. He said that when he was a younger man, he had sailed on a ship where the Captain had used him to fuck the men they had captured. He then proceeded to tell me in particular why he had been used instead of someone else. He said that because his cock was so long and thick that it caused a lot of pain if it is forced inside an asshole without any lube. I pulled my mouth off of the Captain's cock so I could ask him just how large his cock was. He said that it had been measured to be as long as the length of a grown man's arm from his elbow to his knuckles. He also said that it was almost as large as most men's arms.
My mind was running wild as I imagined a man with his arm all the way up to his elbow up my ass. Then again that would explain the fact that my ass muscles had clamped down on his cock and didn't want to relax.
Old Joe then told us of the many men he had ripped open with his cock before they finally told his old Captain what he wanted to know. Old Joe said he really didn't like hurting men in that way and just loved it when the men were able to take his cock without being harmed. He told us of times when he had told the men to continue to scream so he could continue to fuck them. He said he had made a lot of them cum before they would give up information.
The whole time he was telling us these stories I had continued to suck on the Captain's cock and my own had gotten hard again. When I felt the Captain was close to cumming I reached down and started jerking my own cock. The both of us came almost at the same time. As I swallowed all of the Captain's cum, my asshole was squeezing each time my cock squirted. Old Joe timed my contractions and with one swift jerk he pulled his cock out of my asshole with a little scream from me. I could feel the warm cum as it ran out of my asshole.
Old Joe patted my ass and told me he would be honored to fuck my ass anytime I wanted it. He also said that he would always be careful because it was apparent that my asshole would not be able to take much more. I turned around to take a good look at Old Joe's cock. My imagination was not far off as I looked at the largest cock I had ever seen. It was soft but still hung almost half way down his thigh and was larger soft than mine was when it was hard. I was also impressed with the set of balls swinging between the man's legs. Each ball had to be as large as a lemon and they hung almost as far down as his cock did.
My mouth had started to water and my cock jumped as I was feeling that desire again. The Captain noticed and moved in between us and told me that tomorrow I could have all the sex I could handle. Old Joe looked at the Captain in a questioning manner. The Captain told him and me that by tomorrow we would be at some island, which I had never heard of. Old Joe apparently knew about this particular island. The Captain then proceeded to tell me that just about all pirate ships stopped to take on supplies. He also told me that there were no women on the island and a young smooth boy like myself could get rich or in my case get a lot of supplies for the Captain's ship.
He went on to tell me that I would be taken onto the island and for a fee I would do whatever the men wanted me to do. He said that the men would be screened so that I would not be in any real danger. The Captain also said that the owner of the supply house was a big old fat man who loved to get his hands on fine young boys. He had never been known to hurt any, but when he got really aroused he had been known to go for days before he let the boy go. He had also been known to try and buy any good boy he could, but the Captain wanted me to know that no matter what the man offered that I was not for sale.
All the talk of sex had recharged me and both of the men could tell how I was feeling. Old Joe said he had all he could stand for the night as he left the cabin. The Captain told me to move over on the cot and he would see what he could do about giving me some relief. He climbed on my back and pushed his cock inside me. He fucked me for a long while, but would not let me on top. He said he was not up to that again. He slowed his pace down and was able to relax me enough that I drifted off to sleep, dreaming of hundreds of men with all size cocks and all of them wanting my asshole.