This is the third chapter in my ongoing story. All comments are welcome at chartoe@aol.com.
Cowboy To Pirate 3
I settled into a routine of getting fucked by Captain Jack every morning, at least once at night and when he felt like it I had to suck on his thick cock. He always made sure we were not where the other sailors could see us but he did like for me to suck on him while we were on deck. The fucking of the other men was still going on but the loud screams had almost stopped and all I would hear was an occasional moan.
I had become use to and looked forward to my fuck sessions with Captain Jack and several times I had started the action which seemed to turn him on even more. Several times he had fucked me for a long while and when I had shot my load he pulled out and left our room. He would return about an hour later and crawl in bed and go to sleep. On those occasions I was sure I had detected the smell of cum on him. I usually would just snuggle up against him and he would push his ass back against me and go to sleep.
It was on one of these nights that I had to find out just what Captain Jack was doing. As soon as the door closed I jumped up and didn't even bother putting any clothes on. He headed straight to the galley and I was able to follow while staying in the shadows. Captain Jack disappeared through the door and almost as quick the guy that Fred had fucked and taken to live with him came out. He noticed me but didn't say a word as he motioned for me to follow him.
We moved around to a small closet like room that was used to store food supplies and he motioned me inside and shut the door. I could see the light coming through the gaps between the planks. He pointed at one and I leaned in to see what he wanted me to watch, as he peered through the one next to me.
We watched as Captain Jack removed the rest of his clothes while Fred rubbed his slick cock with his hands. I reached over and just as I thought the guy's ass beside me was covered with the same oil that Fred's cock was. He pushed his ass back and my fingers slipped right inside him as he rocked back and forth on my hand.
Captain Jack moved over to a table that was in plain site of us and Fred moved toward him. He leaned across the table and spread his legs as far as he could as Fred rubbed his well-oiled horse cock along the crack of his ass. Fred slowly pulled his cock back and placed the head of it against Captain Jack's asshole. At that very moment the guy beside stepped beneath me and pushed his ass against my hard cock. I had no problem sliding my cock inside his very wet and loose ass.
I continued to watch Fred and Captain Jack as the guy fucked himself back on my cock. Captain Jack grabbed the edge of the table to brace himself just as Fred thrust his entire body toward him. Captain Jack's face seemed to swell and turn very red as Fred's cock forced its way inside him. When Fred pulled back we could here the air being sucked in by Captain Jack. The next thrust seemed to slide in easier and Captain Jack moaned as we watched his cock shooting cum against the table.
Fred seemed to become possessed as he started fucking Captain Jack as hard and fast as he could. The guy beneath me started picking up speed as he pushed his ass against me. I could tell by his movement he was jerking on his cock as he fucked himself on mine. I quickly had to start pumping my own hips, as the urge to release a load became very strong. Captain Jack was moaning and rocking with each thrust of that monster cock s it forced its way deep inside him.
Fred abruptly pulled his cock all the way out of Captain Jack and laid it up on his ass. He looked down at Captain Jack and said he was going to make this fuck last a long time. Captain Jack relaxed on the table just as I heard someone opening the door behind us. Before I could say anything a hand was placed over my mouth and I heard my cock make a popping sound as it was jerked from the guys asshole. The sailor told me that if I made a sound he would toss me over the side of the ship and no one would ever know what happened.
As he released his hand from my mouth his other hand went to my wet cock and he gave it a few jerks. Another sailor stepped in and proceeded to thrust his thick cock into the other guy's ass who didn't seem to mind at all. I did hear a little moan as he pumped his ass back at the cock entering him. I sailor holding onto me pushed me forward and I felt his cock searching for my pussy as I spread my legs to make it easier for him.
He moaned as his cock found its mark and entered my ass. I pushed back and he started pumping into me fast and hard. I leaned against the wall and was able to see the action that was beginning to pick back up with Captain Jack and Fred. Fred slapped Captain Jack's ass pretty hard and slid his cock back down the crack of his ass before pushing it back in. Captain Jack was able to take the cock easier this time but it was still a strain on him and again his cock was shooting cum.
When Fred pulled his cock back it looked as if he was going to pull most of Captain Jack's insides out with it before ramming it all back in. The pace was picking up and I heard the breaths of the two pirates fucking us getting stronger too. I guess the sound of one cumming set the other one off as the two of them moaned and muffled a couple of grunts as I felt my own ass fill full of hot cum.
As quick as they had come into the closet they were gone and the other guy was pulling on my cock. He managed to twist me around until he could push himself back on me. I felt some of the other man's hot cum as it oozed out of his sloppy asshole. I was too close to cumming to worry about anything but getting myself off. Just as I looked up I got a glimpse of Fred's body tensing up as he slammed himself into Captain Jack's ass. I knew from the way his body jerked that he was empting his balls inside Captain Jack.
Fred thrust a few more times and his cock appeared to be coated with his own white hot cum. Captain Jack moaned and I noticed a few more drops of his own cum dripping to the floor. Fred slowly pumped his cock in and out of Captain Jack and I could see the steady stream of cum running out and pooling up on the floor beneath them. The sight was too much for me as I grabbed the guy's hips and pumped faster into his ass as my cock started erupting inside him.
I was still catching my breath when he told me that we should go before Captain Jack came out and found me gone. I pulled out of his ass but really wanted to stay just where I was. We stepped out and I headed off to Captain Jack's quarters with cum running down my legs. I managed to clean myself up before Captain Jack made it back in the room. He grabbed a wet rag and I noticed he was washing himself off when he removed his pants.
He told me to move over as he rolled into bed with me and tuned his back to me. For some reason I felt a little braver than usual plus the picture of him taking on Fred's cock had me horny again. I slipped down until my cock was right against the crack of his ass. I wasn't sure what was going to happen but I knew I had to try something. As I pressed my cock in the crack of his ass he moaned and lifted one leg. This allowed my cock to find his asshole but before I could push it inside he rolled over on his stomach.
He told me to climb onboard and I had better do a good job of fucking his ass. He spread his legs and I lifted myself up and lined my cock up with his still slippery hole. I made only one push as my cock slipped inside. He moaned a little as he pushed back against me. That was all I needed to feel as I started fucking his ass as hard as I could. I could here a few moans along with the grunts as I did my best to fuck as much of me inside him as I could.
I started unloading what cum was left in me inside his pulsing asshole. He moaned his approval as I collapsed on top of his ass. I dozed off as I felt his massive back moving up and down as he breathed. Sometime during the night he had revived and woke me by pumping his hard cock deep inside me until he shot his load. He held me beneath him with his cock still inside as he slipped back off to sleep.
The next morning everything was back to normal as we ate our large breakfast and he took his morning treat of my ass. This time he reached around and jerked me off as he got close to cumming himself. I went through the routine of washing him off and when I went to wash his ass he spread his legs and I got to play with his asshole some before he stopped me.
For several days we had been passing by some small islands and Captain Jack told me that they were uninhabited or at least normally they were. He said that some of the natives from nearby islands sometimes would venture over to hunt or something he wasn't sure. I had looked for hours but hadn't spotted anyone or anything. One of the sailors came running up to Captain Jack and pointed out across the water as he handed him a looking glass. Captain Jack took a quick look and started yelling out some orders. The ship took a quick turn and he headed in toward one of the Islands.
I never asked but I guess he knew I was curious and he told me that they had spotted a ship not far away and in these waters it was always safer to avoid any ships he didn't know. It took us about an hour but we managed to pull into a little cove that hid us on three sides. I had noticed that the sailor with the looking glass had climbed up in the crow's nest and kept looking in the direction the ship had been spotted.
The anchor was dropped and a couple small boats were lowered as some of the sailors prepared to go ashore. They took along some barrels and things to look for some fresh water as the rest of the crew went about business as usual. Captain Jack had become pretty excited from all the action and had me pull his cock out of his pants and suck on it. He didn't seem to care if anyone noticed and I am sure several of the sailors took notice. Several times he had gotten real close to shooting but pulled his cock away and rubbed it across my head.
He looked down at me and told me he was about to blow and that I had better swallow all of it and make sure I cleaned him up when he was through. He was true to his word as I felt his cock begin to swell that split second before the head opens its mouth and shoots forth its hot cum. I almost choked on the first blast but managed to swallow several times and take the next three or four as well. His cock started to soften so I made sure I cleaned it with my tongue before placing it back in his pants.
I looked around and noticed the three or four sailors close bye were all sporting hard cocks. Captain Jack noticed them too and told me to move over by some ropes. He had me get on my knees and had my arms tied behind me. He told the guys they could use my mouth if they wanted. The three almost jumped at me as they tried to be first in front of me. The one that won the honors wasted no time at all as he pulled his cock out and pushed it toward my mouth.
His cock had plenty of foreskin and when he pushed it in my mouth I could taste the salt and cum at the same time. I guess he hadn't washed in some time. He grabbed my head and started pumping into my face like there was no tomorrow. I first thought he was going to hurt me but figured he knew better or he would feel the wrath of Captain Jack. The sailor stiffened up just before I tasted his hot cum as it squirted out of the foreskin that was still covering the head of his cock. He pulled his cock out of my mouth and slowly milked the last drops from his cock and made sure they found their way to my tongue.
The next two sailors didn't last much longer as Captain Jack stood by watching. When they had finished with my mouth, Captain Jack stepped up and placed the soft head of his cock in my mouth and told me to suck on it. I did as I was told and within seconds his cock was rock hard again. He pulled it out and told them to untie me. I followed him to the galley and once inside I was instructed to lay back on the table while my arms were tied down and my legs were pulled back toward my chest and tied in place.
The sailors that tied me up started to leave when Captain Jack told them they could stay and have a piece of my boy pussy. The men gathered around and within seconds I felt a finger driving inside my asshole. I winched and someone applied some oil and the pain quickly disappeared. It was only seconds before I felt the first cock find its mark and the pumping in my ass started. It was feeling pretty good but I really wanted someone to pay some attention to my own cock.
I managed to get into the rhythm of the fucking and felt the first cock erupt inside me. The sailor was pulled off and the last stream of cum shot across my cock and balls. The next few sailors were as quick as the first and just when I was really working myself up they would get off. When I looked around there was only Captain Jack and one other sailor who had a fairly large gut on him. He moved up between my ass cheeks and I felt his cock pushing against my now sloppy hole.
He pushed but his cock was not going in as I figured it would. He grinned down at me as he took hold of my waist and with a powerful thrust, forced my asshole to open up for his very thick cock. I gasped from the pain and pressure as his cock stretched me to the point that I thought I was going to be ripped open. He started pumping ever so slowly, as his cock seemed to stretch me more and more. His strokes weren't long and I knew he wasn't very long but was definitely thicker than any cock I had up my ass.
Captain Jack leaned over and grinned as he asked me if the cock in my ass was thick enough for me. I could only moan as it started sending chills up my back and through my balls. Captain Jack moved behind the guy and I heard the sailor moan as Captain Jack sunk his cock deep in the man's ass. The sailor pushed as far forward as my ass would allow him and just stayed there. Captain Jack started fucking him hard and fast, which caused the man's cock to move in and out of my ass at the same time. Captain Jack was fucking both of us at the same time and we were enjoying it.
The sailor on top of me just leaned over and let Captain Jack do all the work and it was bringing me to a quick climax as well. I was about to go crazy wanting to get my hands on my cock and jerk it but was tied and unable to do so. The sailor looked down at me and started adding some pumping of his own, which was all it took. I felt my ass try and tighten around his cock just as the first stream of cum shot through my cock. Some of it landed on my stomach while the rest managed to cover my pubic hair.
I noticed that strained look on the sailor's face and knew he was on the verge and as Captain Jack slammed into his ass I felt his cock pulse and the warmth spread through me as his cock unloaded inside me. He jerked a few more times before his cock became soft and slipped out of my ass. Captain Jack pulled him off of me and rammed his hard cock deep inside me. I could hear the squishing sound as his cock forced the other guys cum out of me. He groaned one time before forcing his cock as deep inside me as he could and holding it there. His body jerked a little with each volley of cum he sent deep inside me. He slowly stood up and pulled his limp cock out of me and it felt like a bucket of cum came gushing out with it. He told the other man to clean me up and turn me loose as he straightened his clothes and left us alone.
The sailor moved over and collected a bucket of water and a rag before moving back to me. He wiped at my ass and legs and managed to get most of the cum off before he stopped and slipped a couple fingers inside me. I looked up and waited to see just what he was going to do. He grinned at me and slowly worked his fingers inside me until my cock started responding. He leaned over and sucked my hardening cock into his mouth. He worked his fingers quickly and within seconds I was ready to shoot a load in his mouth. He picked up his pace with his fingers and he swallowed my cock down his throat.
I bucked a couple times as I shot what little cum I had left in my balls down his throat. He moaned and sucked as he milked the last drops from me before removing his fingers and releasing my cock. He said he liked sucking cock but if the other sailors knew it they would never leave him alone. He finished washing my ass, cock, and balls before releasing me from the ropes. He helped me get my legs beneath me before leaving.
When I got back to Captain Jack he was yelling out orders to the sailors as the crew came back from the Island with fresh water and some fruit. One of the sailors reported to him that they had found plenty of fruit and fresh water and only some old signs of anyone else being on the island. Captain Jack said that he would send a large crew back tomorrow to get as much fruit as they could carry and more water.
The water and fruit was brought aboard and the boats were just tied to the side of the ship as everyone came aboard and Captain Jack told the cook to get the meal prepared. He said he didn't want any lamps lighted so they needed to eat before it got dark. Everyone was hurrying around to get things ready for the night without any light. We had a quickly prepared meal but the fresh fruit was just what most of us wanted.
As it started getting dark the men moved to their sleeping quarters and the sounds of fucking began to come from almost every corner of the ship. Captain Jack told me to get below and gave a few orders as he prepared to follow me. Once inside I removed my clothes and was waiting for Captain Jack as he entered the room. He was out of his clothes just as quickly and moved in beside me. He had me slip down and suck on his cock as he laid back and drifted off to sleep.