This is the 4th chapter to my ongoing story. All comments are welcome at chartoe@aol.com
Cowboy To Pirate 4
The next morning the sailors were busy getting ready to head back to the Island and I was watching when Captain Jack asked if I wanted to go along. I literally jumped at the chance to go to the island, not to get off the ship but just go to the island. Captain Jack told me I could go along but I should be careful.
It only took a few minutes for us to get to the island and I helped unload the barrels for the water and some big baskets for the fruit that we would collect. The next few hours were nothing but a lot of work as I helped knock down coconuts and cut down some bananas. The others continued to fill the barrels and carry them back to the boats. We were all taking a break and wandering around before having to go back to the boat. I stepped off into the trees to take a piss when I was grabbed by a couple of dark skinned men that were wearing almost nothing.
One put his hand over my mouth so I couldn't call out as they pulled my arms behind me and within seconds had them bound. A piece of a vine was tied around my head and pressed in my mouth which allowed me to breathe but that was about all. I was pretty scared since I had no idea what was going on. They both got still for a few minutes then hurriedly pushed me further into the trees. I was having a hard time keeping up but they continued to push me further and further from the beach.
They finally stopped and as I tried to catch my breath I noticed that both of their little grass loin clothes were standing out in front. I felt a hand on my ass and quickly turned my head to see a third native. This one was bigger and had on a very colorful headdress. He smiled at me and squeezed my ass even harder. I wanted to yell out but the binding in my mouth wouldn't allow me.
The apparent leader of the three mumbled something that I couldn't understand and the other two moved away and started chopping away at some small trees. The other native continued to squeeze my ass and even started using both hands. He was spreading my ass apart and digging his fingers down in the crack of my ass. One of the other natives said something and when I looked around they had managed to place a small tree trunk between some others and made a crude wooden sawhorse.
I was pushed toward the other two as they stepped up and pulled me over by the contraption they had created. My arms were released but were quickly grasped. I was forced to lean over the pole as they retied my hands to the small trees on either side of me. Once one hand was tied the native leaned across me to help with the other and I could feel his hard cock rub across my ass. It was a bit frightening but exciting at the same time.
The leader stepped up and with one hard tug pulled my pants down from my ass. He pulled my right leg up and pulled my foot out of my pants. Once he let my leg go they attached some more bindings to my ankles and stretched my legs apart. Once they had finished I was tied over the small tree truck with my legs spread and my ass exposed to whatever they wanted it for.
I felt a finger being forced inside me and winched when the finger pressed its way inside my dry ass. Something was applied and the finger slipped right in. I felt a couple hands on my ass just before I felt the first cock spreading its way inside me. I tried to rise up to release some tension but the bindings were too tight. The native started fucking me real fast and I knew at the pace he was going he wouldn't last long. I felt him tense up but he quickly pulled out as the other native stepped up and replaced him. This native had a little fatter cock, as my ass was forced open even wider. He too was fucking me real fast but pulled out before shooting his load.
The big native moved up behind my ass and taking each cheek in his massive hands squeezed them hard before spreading them as far apart as he could. It felt as if he had my asshole spread open as well. I felt the head of his cock rub against my asshole and knew he was the largest of the three. He started a low deep moan as the head of his cock eased just inside my asshole. He thrust forward and groaned as I gasped for air. This guy was intent on fucking me hard and had a good start to it. He pulled his cock all the way out and gave me just a few seconds to catch my breath before he rammed it all the way back in. He did this about ten times as he told the other two something and I felt their hands grabbing either side of my ass cheeks and spreading them as far as they could.
This guy was trying to fuck as much of himself inside me as he could. His balls were hanging low and began slapping against mine as he picked up the pace of his fucking. One of the others had leaned against my arm and I could feel the wet stream of pre cum as he ground his cock against me. The native fucking me started mumbling something real deep as if he was cussing and let out a couple of groans as his cock erupted inside me. He slammed into me a few more times before pulling his limp cock out of my ass and stepping back.
The other two almost fought as they both tried to fuck me at the same time. I could feel the hot cum running out of my ass and down on my balls as one of them managed to get his cock inside me. My ass was so loose the he started pressing my ass cheeks together as he pumped into me. He only lasted a few strokes and pulled out, to let the third one finish off in my ass. Just as they started to leave me tied up one of them reached down and released one of my hands. This allowed me to slowly release the other bindings and gave them plenty of time to disappear into the jungle.
I managed to find the beach just as they were beginning to spread out to look for me. The sailor in charge came up to me and wanted to know where I had been that they had been ready to go back to the ship, but wasn't wanting to tell Captain Jack that I was gone. I gave him a story of being lost and he commented from the looks of me that I looked like I had been stumbling around for some time.
I managed to fall down in the water a few times while we were pushing the boats out to deeper water. Really did it to wash off some of the cum that was leaking out of my asshole. The guys just laughed at me and helped me up. We made it back to the ship but all was quiet as we got closer. The guy in charge had us stop rowing as he looked around the ship. All at once several men showed up at the side of the ship and ordered us to put down our weapons and come aboard. We did as we were told and slowly climbed back up on board.
As we stepped onto the deck we were grabbed and our arms were tied behind our backs. I noticed the other ship that was a few hundred yards away. There were some men unloading mostly the water and fruit that had been gathered earlier. Some of the pirates climbed down into the boats we had been in and very quickly were rowing away toward their ship. I heard some moaning and turned to see Captain Jack tied to the rail in front of the steering wheel. His pants had been ripped off and it was apparent he had been used several times by some of the pirates. He actually was getting fucked hard by a big pirate when I noticed him. This pirate was having no mercy on Captain Jack's ass, as he slammed into him as hard as he could.
Captain Jack appeared to be in some pain but when I noticed his hard cock jumping around I knew he was just letting the pirates think he was in pain. There was one pulling his pants back up and another that was standing in line waiting his turn. I noticed the one fucking him tense up and at the same time I saw the white stream of liquid shoot from Captain Jack's cock. The pirates couldn't see his cock, which probably helped the little act that Captain Jack was putting on.
The one pirate pulled his cock out of Captain Jack and wiped it on his shirt as the other one started swinging his 8 or 9 inches around so Captain Jack could see. Guess he figured it was really large and would put a little fear in Captain Jack. They are just lucky they had not stripped Fred naked and they would have seen what a real big cock looks like. The guy moved behind Captain Jack and with one quick movement has his cock buried inside. Captain Jack grunted but I was sure I saw a little smile come across his face. The pirate must have been really worked up as he quickly started grunting and shooting his load.
The captain of the pirates yelled out some orders and they started leaving the ship. Within just a minute or two they had left us there with our hands tied behind us and Captain Jack tied to the rail. It took about five minutes before someone managed to get loose and started helping the rest of us. Fred went up and untied Captain Jack and helped him toward his cabin as the other sailors started checking out the ship. The pirate ship was moving out of site and our small boats were floating back toward us. One of the sailors dove into the water and started swimming toward them.
I headed to Captain Jack's cabin but stopped short when I heard the familiar sound of ass being pounded by someone. As I got close to the door I heard Captain Jack telling Fred to fuck him harder. He said the others had only managed to get him hot and he needed to be really fucked. Fred grunted as I heard his thighs slap into Captain Jack's ass. I figured I would go see what was happening around the ship and let Captain Jack and Fred alone.
The sailor had managed to swim to the boats and was slowly rowing them back one tied behind the other. The others were looking to see what had been left on the ship as they yelled out what they had found that had been missed. The sailor that had headed the party to the island was yelling out orders as some of the men started preparing for a return trip to collect more water and fruit. He noticed me and said that I should stay and help the cook clean up while they made another run to the Island.
I went back to Captain Jack's quarters and when I didn't here any noise I tapped on the door. Captain Jack asked who it was and told me to come on in. Captain Jack was still leaned over his desk with Fred's cock deep inside him. I stopped when I saw them but Captain Jack told me to get a bucket and rag so I could clean them up. I did as he said and they both remained locked together. When I returned neither of them made any movement and I wasn't sure what I was too do, but Fred's big round ass was giving me a hard on.
I took a rag and started cleaning the cheeks as he relaxed under my attention. Soon he spread his ass and I made sure to clean the sweat off of him that had run down the crack of his ass. He seemed to like me rubbing his asshole too as he swayed ever so slightly as my hand and the rag passed between his ass cheeks. I moved down and got both hands on his huge low hanging balls and as I pulled down on them I started pulling his soft cock out of Captain Jack's ass. There was a sucking noise just before his huge horse cock dropped out and started swinging back and forth.
I noticed the cum dripping off of his cock and dropping to the floor just as I reach out and pulled the cock back until I could wipe it clean with the wet rag. He stepped back and turned toward me as he let me clean him thoroughly before stepping away. When I looked back at Captain Jack's ass the cum had a path from his gapping asshole, down his balls and was dripping on the floor. His asshole was spread open and it appeared to be swallow and all pink and puffy. I gently rubbed the wet rag around it to the satisfactory moans of Captain Jack.
I managed to clean his ass and balls before he turned around and offered his cock to me to be cleaned. He was getting his energy back and before he pulled his cock away I felt it start to grow a little. He said I could finish the job later as he got dressed and said he had to go see what needed to be done on the ship. Fred left and said that the pirates had missed most of their supplies since he kept it hid away so none of the guys on board would be tempted to steal it.
When we got back upon deck the two boats were all ready on their way back to the island and there were only a few guys moving around. Captain Jack had me get another bucket and clean off the deck where the pirates cum had dropped along with some of his own. We spent the next couple hours cleaning up and waiting for the party to return from the Island. We could smell the food that Fred had been preparing and we were just waiting for him to call us to come eat.
By the time the sailors returned from the island we had filled our bellies and they went about eating while we put away the fruit and fresh water they had brought back with them. We were fastening the boats securely to the deck when someone yelled out from up in the crows nest. We all looked up at him and then across the bay in the direction of where he was pointing. Off in the distance we could see the dark trail of some smoke rising into the sky. We couldn't see what was burning but there was no question it was probably done for.
Captain Jack started yelling out orders and the men went scampering in all directions as the anchor was pulled up and some sails were lowered. At first I could only detect the slight movement of the ship but very soon the sails filled with air and the ship seemed to lunge forward. We were moving fairly fast and the smoke stream was becoming larger. The sailor up in the crows nest yelled out that there were two ships, one burning and the other just near by. Captain Jack asked him if he could make out anything about the ships but he replied he couldn't. We all went forward staring out hoping to see whom the two ships belonged too.
As the two ships got in sight the one that was not burning turned in our direction and the sailor yelled out it was Captain Walrus's ship. Captain Jack had a relief look on his face and I assumed that we weren't in any danger from them. As the ship got closer Captain Jack had them run up some flags and I noticed the other ship did the same. Both ships dropped their sales and started slowing down as they drifted closer and closer. Once they were close enough, sailors from both ships started tossing hooks attached to ropes across to the other ship.
The ropes were pulled tight and tied up as the two ships were pulled closer and closer together. Once the they were beside each other some planks were placed between them which created a bridge. I heard the voice of the other ships Captain as he hailed to Captain Jack. He told him he was coming over and to hold our ship still. This caused a little uproar among the sailors as Captain Jack moved to the bridge. I watched as this man they called Captain Walrus stepped upon the bridge.
He was not very tall but he was a big fellow. He probably weighed twice what Captain Jack did and he had a couple sailors steadying him as he crossed the bridge. Once on our ship Captain Jack shook his hand and gave him a big hug. They started chatting about how long it had been since they had seen each other. Captain Jack finally got around to asking about the burning ship.
Captain Walrus told him that they came upon them and they tried to board his ship but they were waiting for them. He said they had no trouble fighting them back and decided to just burn their ship and turn them loose in their little boats. Captain Walrus asked if they had hit us and Captain Jack told him what happened. Captain Walrus thanked him for the fresh water and fruit they were able to retrieve before setting the ship on fire, and then laughed.
Captain Jack invited him to go with him to his cabin and yelled for Fred to bring them some food. All the sailors just leaned over the sides of the ships and yelled back and forth at each other. It was apparent that a lot of them knew each other. I sat down not knowing what to do when Fred came back from the cabin and told me that Captain Jack wanted me. I figured he wanted me to clean up some mess they had made with the food so I headed inside.
When I got inside the two of them was just sitting there chatting and Captain Jack motioned for me to come over. He had me stand in front of Captain Walrus as he started rubbing his hands up and down my body. He grabbed my balls and cock a couple of times and then squeezed my ass. He told me to remove my pants as I noticed he started unfastening his shirt. As soon as my pants were down his fat chubby hand gripped my cock and started pulling on it as if he was milking a cow.
He pulled me closer as his shirt opened and I noticed he had breast bigger than most women. He reached inside his shirt and pulled a breast out and slowly pulled my head down to it. He told me to suck on it as if it was own mothers breast. I started sucking and I felt his body jerking a little as my tongue rubbed against his nipple. He moaned and pulled my face in even harder against him as his other hand started pulling my shirt up over my head. He pulled my mouth off of his nipple, which caused a popping noise. He removed my shirt then pulled me back down on his breast.
His breasts were huge and hung down on top of his large stomach. There was a patch of hair in the cleavage, which I reached up and rubbed my hand through. He just moaned as he pushed his other breast up to my mouth. I took turns going from one nipple to the other as he pulled me into his stomach. My cock was hard and leaking pre cum on his stomach, which he seemed to enjoy.
He pushed me away and told Captain Jack that we needed to use his desk. Captain Jack cleared everything off of the desk and said it was no problem. I noticed he had pulled his cock out and was slowly jerking it as he watched Captain Walrus remove the rest of his clothes. He had his back to me and I just stared at the size of his naked ass. I was thinking his ass was so big that I could probably fall off in there and get lost. He waddled over to the desk and turned around as he laid back on it.
He motioned for me to join him as he spread his legs. I could see the head of his wet cock poking just out of the mound of fat beneath his belly. He was so fat that he had no balls hanging but only a dark round area where his balls probably were and it was stretched tight. He told me to suck on his cock as I moved close. I tasted the sweet pre cum leaking from his cock and pushed my face down on his cock.
It grew even more and was able to fill my mouth even though his mass was pushing back against my head. He moaned a few times and started pumping his massive ass up and down on the table. Captain Jack told me to move down and eat his asshole out for him. I did as he said and quickly found that is pink hole was not as tight as I figured it would be. My tongue slipped in easily as he bucked on the table. He was moaning and groaning as he ground his ass against my face while my tongue darted in and out of him.
He told me to fuck him and fuck him hard. I looked up at Captain Jack and the told me to do as he said. I stepped up and placed my hard cock against his asshole and gasped a little, as it seemed to be sucked inside. The man's pussy was hot and moist as I started pumping in and out as fast and hard as I could. I looked up and watched the ripples running across his massive stomach each time I slammed into him.
He started telling me to fill his ass full of my hot cum as he tried to buck even faster onto my cock. Captain Jack moved in behind me and started pushing a finger up my ass as I pumped away. It only took a few seconds before my cock was shooting with all its might into the big man's pussy. He moaned and said my hot cum felt so well inside him. I pumped a few more times before I felt all the energy draining out of my legs.
Captain Jack pulled me away from the man's asshole and quickly lined his massive cock up and thrust forward. The man's body tried to lift itself up off the table as the cock spread him really wide as it went all the way in. He gritted his teeth for a second then let out a deep breath as Captain Jack started pounding his ass hard.
Captain Walrus started moaning and bucking as he was now enjoying the big cock filling his massive ass. He said he needed something to suck on. Captain Jack told me to get upon his chest so he could suck my cock. I tried to get in a position where I wouldn't be hurting the man but he told me to just sit on his chest and get my cock as close to his mouth that I could. He sucked my cock along with his own ass juices and some of my cum into his mouth as he moaned and his body bucked a little.
I could hear and feel Captain Jack pounding away at the ass while his mouth was nursing on my now hard cock. I could hear the squishing noise as Captain Jack's hard cock moved in and out of the man's asshole. I felt the man's body tense up beneath me and knew he was about to shoot a load. I turned so I could see and saw the first stream as it actually shot out and landed on Captain Jack's cock as it moved in and out. The man kept bucking with each stream of cum and when he had stopped Captain Jack didn't have a pubic hair that wasn't soaked in cum.
Captain Jack dug his hands into the man's massive legs as the rammed his cock all the way inside. His body tensed and jerked as he filled the man's ass full of cum. This caused the man to moan even more as he started sucking harder on my cock. I got lost in all the lust and started fucking his face as hard as I could. It didn't take much before I was filling his mouth full of cum and gasping for air. I looked down at what I had done and was sure I was about to be beaten or whipped. Captain Walrus must have seen the fright on my face as he told me I did a great job and could I help him get back on his feet and cleaned up.
I jumped down and told him to stay where he was as I got the bucket of water that I used to clean Captain Jack with. I wiped all the cum and juice off of his ass and legs that I could bet his asshole would open and contract every few seconds as some more cum would roll out. He finally sat up and told me to move the bucket as he straddled it and almost sat on top of it. He made a face as he forced the remaining cum from his ass. There was a steady stream then only a few drops. I wiped his ass for him one more time before he started getting dressed.
Captain Jack looked at him and asked if there was anything else we might do for him. He said he didn't think so as he pulled his pants up over his stomach. Captain Jack winked at me and told him that he could go get Fred to come service him if he liked. Captain Walrus spun around and said he didn't want that horse cock anywhere near his ass. He said the last time Fred fucked him it took two weeks just to learn to walk right again. Captain Jack laughed at him as he patted him on the back.
We all got dressed and returned to the deck of the ship as Captain Walrus said they needed to head off and he started toward the makeshift bridge.