This is the second chapter to my ongoing story. All comments good or bad are welcome at chartoe@aol.com
Cowboy to Pirate 2
We herded the cattle into a holding pen at the edge of town and immediately were looking for a place to clean up and get a good meal. The owner was waiting for us when we got to town and said he had everyone's pay and that he needed part of us to carry half of the herd over to another town days ride further. He said he would pay extra for anyone that wanted to go. He told us we could all have a night on the town and decide in the morning.
We collected our pay and John had me go straight to the bank and wire almost all of my earnings back home. He said he didn't want me wasting it or getting it taken from me. Afterwards we got a room and cleaned up before getting some real food. We finished it off and went to the only saloon in town and had a few beers. Most of the people there were from the cattle drive so there wasn't anything to worry about.
The boss came bye and leaned over and wanted to know if I had enough beer yet to loosen me up for a night of fucking. I grinned at him and he knew along with John that I was ready to go. John and I left the saloon as the boss went to the bar to have one more drink. I was feeling the beer pretty good but was able to walk without any help.
We got to the room and I was taking my clothes off before John could get the door shut. He commented about how I had really gotten to love being fucked. I only grinned as I stepped out of my pants and reached to help him out of his clothes. I had not had John's cock inside me since the last time we had a room and wanted to have him fuck me before the boss came up and stretched my ass.
I pulled John to the edge of the bed and sucked his semi hard cock into my mouth as he moaned and grabbed my shoulders. His cock was hard within seconds and I was making sure I got it good and wet for him. He was beginning to fuck my face and I knew it was time to let him fuck my ass. I turned around on the bed and pushed my ass toward his cock. He immediately spread my cheeks and rubbed his cock along my asshole. He stopped and positioned himself for the initial thrust. I pushed back and tried to open up as much as I could.
Both of us moaned out as his cock forced its way inside me and I only felt the hard warmth of his cock going deeper and deeper inside me. I quickly felt those lovely chills shooting through my body and started pumping my ass back on his cock. John grabbed my hips and started pumping in and out of me as fast as he could. Both of us were moaning and groaning when the door opened and the boss stepped inside. John never lost a stroke as he continued his attack on my ass.
The boss moved around to the other side of the bed and I noticed the bottle of liquor that he had with him. He removed his pants in a hurry and his cock sprang up to greet me. I sucked a little of the head into my mouth as he removed the rest of his clothes. The head of his cock immediately filled my mouth and along with the pounding on my ass by John, it was being forced in and out.
The boss reached for a glass and poured it about half full of whiskey as he pulled his cock out of my mouth. He dipped his cock into the glass then placed it at my mouth. The whiskey added a different taste to his cock and he started feeding me more whiskey in that manner. John told him I had never had anything stronger than beer and might not want to give me too much. The boss said he would stop before I had too much. John was beginning to pick up speed and I knew he was close to shooting his load.
The boss grabbed my shoulders and held me still as John slammed himself into my ass shooting his load deep inside me. John stopped and rested as the boss pulled away from my head and made his way around behind me. He took a deep drink from the bottle and handed it to John. As he moved up between my legs he rubbed his cock up along the crack of my ass and coated it with John's cum that had leaked out of my asshole.
He grabbed my hips and gave no warning as he rammed his cock all the way inside me. I gasped as the invasion knocked the air out of my lungs but before I could recover he was fucking me fast and hard. John reached beneath me and gave my pre cum leaking cock a few jerks and it was instantly hard and working toward an orgasm in record pace. Before I had time to even moan my cock started spraying my cum on the bed beneath me.
The boss moaned and said it felt great when my ass squeezed tight around his cock. He started pumping faster and faster and just when I thought he was going to cum he pulled out. He said he decided that he was going to make this fuck an all night thing and took another drink from the bottle. John moved around and placed his cock in his cum soaked hand and offered it to me to lick. I immediately obliged him as his cock started growing. I was really enjoying John's cock when I felt my ass being stretched open again as the boss rammed his cock back into me.
The squishing noise it made as it went in was pretty loud and I squirmed my ass to take all of the cock. I moaned as I felt my cock erupting again as the boss started pumping rapidly in and out of me. When he felt my ass tighten around his cock he slowed down and started pulling his cock all the way out of my ass before slamming it back into me. He continued this for a long time and I was really enjoying the slow and sudden attach of his cock in my ass. He managed to pull out once more to stop himself from shooting.
John moved around and said he couldn't wait anymore as he pumped his cock into my waiting ass. He lasted less than a minute and was breathing real hard when he rolled over on the bed beside me. The boss started dipping his cock in the glass again and feeding me some more whiskey.
After finishing off the glass of whiskey the boss had me move as he lay down on the bed with his thick cock sticking up toward the ceiling. He told me to climb up on top as he took another drink from his bottle. I squatted down as John held the boss's cock where it was lined up with my asshole. The head slid in pretty easy and the boss thrust up and forced the rest of it inside me. I sat down for a second and let my ass relax before I started bouncing up and down on the cock.
I was quickly building toward another orgasm and the boss told me to ride his cock like a bucking horse. The closer I got the louder my moans were getting and the faster I was trying to move. The first stream of cum shot all the way up on the boss's chest and he grunted as he thrust into me hard as his own cum filled my ass. I slowed down as my orgasm ran its course and my cock was shooting blanks. I felt the hot cum leaking out of my ass as John tossed us a towel and I rolled off of the boss's soft cock.
I cleaned us up as best I could before rolling up against the boss. John moved in behind me and as I dozed off I heard the boss say he was really going to miss my ass after tonight.
During the night he managed to wake up long enough to place me on my face and fuck my ass until he deposited another load then drift off to sleep with his cock inside me. John managed to get me from beneath the boss and have his on turn the next morning. I was really loose and relaxed after the night of being fucked and was glad to take a bath even though the water was cold.
John and I decided to help take the cattle to the next town plus it would give us one more night to be together before we decided just what we were going to do afterwards. We started fairly early and were on our way when the owner came by and said he would go ahead and make arrangements for our pay. It was really an easy ride and we could smell the ocean a long time before we could see it. John asked if I had ever seen it before and when I told him I hadn't he said he would be sure to take me to a place where I could see it from a distance and get an idea of just how large it really is.
We had no trouble getting the cattle into the makeshift pens when John decided that we should take a ride before cleaning up. We headed out toward a tall ridge and as we rode I could see the spacious ocean spreading out before us. When we topped the hill all I could see was ocean and was really amazed at the size of it. He tried to explain to me just how vast it was but finally said unless you ever travel on it you really want understand.
On the way back to town I kept thinking how great it would be to sail on the ocean instead of riding around on horses. We found a place to stay after collecting our extra pay and John took me to a place that had a bunch of fish and sea food that I had never seen or tasted before. After sampling some of the things we got a few beers and headed back to the room for a long slow night with each other.
The next morning we got up and John wanted to know what my plans were and I told him I guess I should be heading back home to let my parents know I was all right. He said had decided to take part of his wages and try his luck in the gold fields. We said our good byes and he told me to be careful on my return trip.
I was about to ride out of town when I decided to stop and get some extra supplies from a combination saloon and general store. When I entered I noticed that there were a few sailors sitting at a table drinking and I kept looking at their type of dress. A voice at the bar scared me when he asked if something was wrong with what I was looking at. I quickly told him no that it was the first time I had seen sailors and the way they dress was new to me. He gave me a half grin and said he understood and poured a small glass of whiskey and handed it to me. I started to refuse but he told me it would be bad manners to not except at least one drink.
I sipped it at first then figured it was best to swallow it all at once. The man slapped me on the back and told me that was the way a real man drinks whiskey. He started chatting to me about where I was from and where was I headed and all, as he continued to fill my glass again and again. I was feeling pretty relaxed and believe the guy with me could tell. He asked if I wanted to sit at a table with him while we finished the bottle. I managed to make it to the table without knocking anything over and once I sat down he placed another glass in front of me.
The stench of urine, body sweat and just plain filth woke me up as I began coughing the bad air from my lungs. I was alarmed when I realized my hands were tied behind my back and with the exception of my pants I was naked. I heard others moving about but my eyes could not adjust to the deep darkness. I felt the entire room move and gasped, someone told me to relax that a ship always did that when it was on the ocean.
I asked the man where we were and he said that along with the other men in the room that we had been given a job as sailors on this ship without pay and liberties of course. He said the term for what had happened to me is called shanghaied. He said I would figure it out soon enough as we had been out of port for a couple hours all ready. He said it wouldn't be long before they came down below and started telling us what we had to do. He also said it was probably best to just do what they told me or they would just throw me overboard.
What he was telling me was not helping me feel any better but I figured I would just have to wait and see what happened. We were there in the darkness for a couple more hours before the sudden bright light came through a hatch above us. It caused us all to hide our faces. Some sailor yelled out for us to stand up and move to the ladder. When we made it there, a sailor cut the ropes that bound our wrist. As he cut them he told us to climb up, which we did but each winching from the bright light.
When we were all on deck the man I had been drinking with stepped up and said that we had all been chosen to work for food and bedding on the ship. We would be at sea for a couple months before we made ground again or at least those of us he was talking too. He said that if any of us had plans of trying to jump ship that it was best they do it now because the penalty would be the same no matter when we tried. He said we could take forty lashes from a rawhide whip, which would probably kill us, or jump into the shark infested waters. Since there was no land in sight in any direction we all figured our chances of living were better on the ship.
Captain Jack order us back below deck and said we would be given some water in which to clean the filth off of us and some clothes that would be more comfortable for our trip. We descended the ladder and were all standing around when buckets of water were lowered to us and we were ordered to strip and toss the clothes in a pile. We did as we were told but most of us, including me, were a bit ashamed of being naked in a room of men.
Several of the men were cupping their cock and balls as if they were cold but it actually was hot and humid in what I learned later was called the hole. A couple bars of soap were tossed down to us and the orders to scrub all the filth off was given, then as an after thought we were told to be sure that everyone was scrubbed clean or we would all pay for it. A few of the men grabbed the soap and splashed some water on themselves as they lathered themselves up and then asked someone near them to do their backs.
The rest of us followed suit and I was helped and helped the only guy in the group that was carrying a few extra pounds. I was thinking that after a few weeks of work he would be skinner than most of the men there. I had finished his back and turned around for him to do mine when I felt his hand slide up between my ass cheeks. At first I started to spread my legs then remembered where I was and clamped my ass cheeks on his hand. He removed his hand and whispered to me that I did have the nicest ass there. When he rinsed my back off I turned around to see that he was sporting a hard cock that actually was leaking some pre cum.
We started climbing the ladder when the sailor ordered us back upon deck. He stopped the oldest man in the group and told him he was to stay in the hole and use the water to scrub it clean and to take the clothes and toss them overboard. We were lined up on the deck and a couple of the sailors walked past us and tossed a pair of pants and a shirt and told us to hold onto them.
Captain Jack came down to where we were and started walking past us and looking us up and down as if he were inspecting some livestock. When he was finished he pointed out several of the men and told one of the sailors to take them and they were ordered to dress. They left and there were only four of us left standing there, holding our clothes in our hands. Captain Jack passed by the first two and told the sailor following him that they were to go to the cook. He looked at me and the guy that had washed my back and had a questioning look on his face.
He looked at me real close and asked just how old I was. I told him in a crackling voice that I would be 17 in a few months. He reached over and grabbed the other guy's ass and squeezed it hard as the man tried not to yell out. He grinned and said that both of us were to report to his cabin before he decided which would be his permanent cabin boy. He gave the guy's ass a firm slap as we followed the sailor away.
We entered the cabin and were told to just stand next to the wall as the sailor left the room and shut the door. I looked at the other guy and asked if he had any idea of what was going to happen to us. He said he wasn't completely sure but believed we were about to get our asses fucked. I thought for a second that that wasn't that bad but the scared look on his face wasn't making me believe it.
The door opened and Captain Jack walked in. He unbuckled his thick belt that also held his sword and placed them beside his desk. He looked at both of us and said that he planned on pleasing himself with both of us and the one that he liked the most would become his cabin boy and private pussy boy for the trip or until he couldn't take it anymore and had to be replaced. He stood up and dropped his pants and we both gasped a little as we watch his thick long cock swing back and forth.
Captain Jack looked at me and told me to see what I could do about getting him hard. I moved to him and after pushing the foreskin back over the head I sucked the cock into my mouth. I could feel it starting to harden. He ordered the other guy to come over and bend over his desk. The guy did it but I could tell by his slow movements that he did not want to.
I jumped when I heard the first slap hit the guy's ass and heard a muffled cry come from him. Captain Jack gave him a few more before he stopped and turned his attention to my mouth. He held my head still and pumped his cock into me until it hit the back of my throat and was making me gag. He pulled his cock away and stepped around behind the guy's ass and as quick as he had slapped the guy's ass he rammed his cock all the way inside him. The man couldn't help but yell out and Captain Jack said he liked to know when his cock was stretching a virgin asshole.
The guy had stopped screaming but was trying to catch his breath as Captain Jack slammed into him over and over. I noticed a funny look come across the guy's face as he raised his head up and stopped gasping. His body jerked a few times then his head went back to the desktop. I noticed he seemed to have relaxed and I was wandering what had happened. Captain Jack looked at me and said the guy just found out what it felt like to have a thick cock make him cum. I looked between the guy's legs and noticed the pile of hot white cum that was collecting beneath him.
The guy started whimpering and I thought he was in pain but when I noticed him fucking his ass back on Captain Jacks thick cock I knew he was enjoying the fucking he was getting. My cock was standing tall now and Captain Jack pulled the guy off of the desk and told him to suck my cock while he fucked his ass. The guy did as he was told and pretty soon had me pumping at his mouth. Captain Jack told me not to shoot in his mouth, that he was going to let me deposit my load in the guy's ass.
I was getting real close when Captain Jack pulled his huge cock out and told me to finish myself off in the hot juicy pussy he had opened up for me. When I looked down the asshole almost looked too large to do my cock any good, but it was beginning to close as I pushed my cock inside. The guy moaned so I started fucking as fast as I could. It was only seconds before my entire body tensed and ejected my load of cum. I stepped back a little weak kneed as Captain Jack spun the guy around.
He took his cock and slapped it against the cum leaking asshole before forcing it all the way in. Captain Jack was wasting no time as he fucked the guys ass as fast as he could. I watched as the guy tensed up again and noticed the stream of cum shoot from his cock. Captain Jack growled as he slammed into the guy's ass and held his cock there while his body jerked. He pulled out and slammed into him a few more times before he jerked his cock out of the guy's asshole. Captain Jack said he liked to watch his cum rush out of an asshole as there was a steady stream of his and my cum coming out of the man.
Captain Jack jerked the guy's head up and asked if he wanted some more. I was surprised to see the glazed look on the man's face but he nodded that he did. Captain Jack stepped to the door and told them to send the cook in. When he turned back he told me to move everything off of the desk. He then had the guy lay on his back and pull his legs up in the air. He reached up and tied some straps to the man's ankles and had his still leaking ass spread.
The cook walked in and had to duck to enter the room. Captain Jack said he had a present for him and he could take as long as he wanted. He introduced us to Fred the cook. Fred looked at the man on the desk with his legs spread out and smiled as he started toward him while loosening his pants. I gasped and the guy on the desk tried to look up as the Fred pulled out the largest cock I had ever seen. The only thing my horse had that Fred didn't was length. The cook was just as impressive as his cock with huge arms and legs with almost no body hair. He was some type of Island person similar to the ones I had seen in some sideshows.
He grabbed the guy's hips and placed his cock at the entrance of the guy's asshole. The guy had no idea about what was about to surely rip him apart. Captain Jack sat back on his bunk and pulled me into his lap as he reached around and started playing with my cock. Fred thrust his powerful thighs and his cock halfway disappeared inside the man's asshole. He tried to scream but no sound came out and we all watched as a stream of cum shot about two feet about him. The look on his face is hard to describe, as there was unbelievable pain right along with pleasure.
Fred started pumping, as he was able to force his horse cock deeper and deeper inside the guy. The guy's cock was jerking with each thrust but it was apparent there was no more cum inside his balls to be released. He had this far away look on his face as his body was being pounded on the desktop. I noticed his legs had become limp and his abdomen was moving up and down as the cock entered him. We heard a few moans come from him and it was apparent he was receiving a lot more pleasure than pain.
I had not realized it but I had reached down and was gently milking pre cum out of Captain Jack's cock as he slowly worked mine up and down. I moved down and sucked his cock into my mouth as he held onto my shoulders and moaned while watching the show Fred was giving him. I heard the cook start moaning and Captain Jack told him to pull out and shoot on the guys belly. He pulled me up from his cock and turned me around so I was facing the show and just about the time Fred pulled his cock out, Captain Jack forced his inside my ass. I spread my legs and leaned over to accommodate it.
When Fred's cock erupted it was the largest amount of cum I had ever seen come out of a man's cock. It completely coated the guys cock and pubic hair and was running down between his balls and thighs. Captain Jack almost instantly lost his load inside my ass as he held on tight and pumped a few more times. He asked if sometime I would like that load up my ass. I looked back and him and I guess the look on my face showed the fear of trying to take that monster inside me. He laughed and said that if my friend there could keep Fred satisfied that I wouldn't have to worry about it.
Fred untied the guy's legs and lifted him up on is shoulders and the man only moaned to assure us that he was still living. Fred carried the man out the door with the cum dripping off of both of them. Captain Jack told me to move over to the inside of the bed and get a little rest for now because he said he planned on fucking me several more times during the night. I curled up against him once he got in beside me and dozed off to the gently rocking of the ship.
Captain Jack was true to his promise and three times during the night I felt his cock poking me awake as he rolled over on top of me and forced it in side. I had loosened up enough that I was able to actually fuck back against him the last few times he fucked me. Early in the morning he dozed off with his cock deep inside me. A loud knock on the door woke both of us and Captain Jack yelled for the guy to come in. It was one of the men that had been in the hole with me and he was walking a little gingerly which told me his ass had been used during the night also. He sat a big tray of food down on the desk and left the room.
Captain Jack had me get up and we had plenty to eat and when he had enough he bent me over and took his morning fuck of my boy pussy. When he was finished he told me to turn around and jerk myself off while he watched. It didn't take long at all and just when I was about to shoot he moved up in front of me and had me spray it on his stomach. He rubbed it around with his fingers then fed it to me. He had me get a bucket of water and wash him off before I was allowed to wash myself. He dressed and headed out to see that everything was going all right on the ship.
After getting dressed I was allowed to go topside and look around. I noticed several of the men that were in the hole moving around and doing odd jobs, mostly cleaning around the ship. I did notice that from time to time one of the men were pulled below and I could hear the noises being made by someone getting fucked really hard. After about an hour I noticed the cook was tossing something over the side of the ship and figured it was some food gone bad. Right behind him was the guy he had fucked and he still seemed to have that faraway satisfied look on his face.