This is a totally fictional story about a young cowboy that finds out he enjoys other men on a trail drive and is later thrown into the world of pirates on the ocean. If this type of story is not for you then you should leave before reading. Any comments are welcome at chartoe@aol.com
Cowboy to Pirate
I grew up on a small cattle ranch in the mid west and fancied myself as being a cowboy of sorts, even though I was only in my middle teens. I had mastered all the roping, riding and of course had that cowboy bowlegged strut down too. I was pretty much a full-grown man in size anyway. Had been doing as much work with the cattle and horses as any of the other men that worked around the ranch.
The railroads had come through the nearby town and most of the cattle were being shipped by rail which cut way down on the roundups that came through. I was really disappointed because I had finally gotten old enough that my father would let me go off if I wanted too. We had discussed it many times and he knew that I wanted to go on one.
He got word that there was going to be a big roundup heading out toward California to the gold fields. Some big rancher had gotten the idea that if he could get a few thousand head out there that he would get top price for them. He was looking for cattle hands to make the long trip and was paying good wages. My father said it might be my last chance to get to go on a roundup and it was up to me if I wanted to go. It only took me a couple seconds to tell him I wanted to go.
We made all the necessary connections to get me to this guys ranch a few days before we had to push off. I stayed in the bunkhouse with about twenty other cowboys and could tell by most of their ages that they had been doing this for a long time. I felt really unsure of myself around them but most of them would just give me a hand and show me what needed to be done with the tack and all the other things that were being prepared for the trip.
There were a couple of guys just a few years older than myself, but they looked like they had lived a pretty tough life so far. While we would wash up I noticed that most of them were wearing souvenirs of scares from either fights or mishaps they had been in. I felt a little self-conscious with my almost white body that had rarely been bruised or exposed too much sun. My mother would never let me go without a shirt even when the other hands had peeled theirs off.
It was during these cleaning periods that I became aware of a certain stirring in my jeans that I had not had before. Now I had definitely played with my cock as often as I had been able too, but when it came to anything other than my hand I was a complete virgin. One of the older cowboys had noticed that I wasn't feeling too easy around all the nude chest and guys walking around the bunkhouse in their underwear.
He told me to go with him and help him with some of the gear in the tack room. On our way to the barn he asked me just how old I was and a lot about why I was there. I told him pretty much my whole life and he just listened. Once inside he said he didn't have anything for me to do but wanted to get me away from the others before they did or said something that might get me in trouble sexually.
I just looked at him and he knew I didn't know what he was talking about. He said he could tell by the way I was trying not to look at the other cowboys that I was somewhat attracted or curious about them. Before I could say anything he told me to just listen. He went on to explain that he was not judging anyone but had seen times when a new young guy was taken advantage of and when he decided it was not what he wanted it was too late to make the others stop.
I kind of got the idea of what he was talking about but then wanted to know just what this young guy had gotten himself into. He looked at me and said that it started off innocent enough. He said the boy had gotten a little attached to one of the other cowboys and was always hanging around him. After a week or so on the trail the older cowboy got pretty horny and started rubbing on the boy and before he knew what had happened the young boy was sucking the cowboys cock whenever he wanted him too. This was known by all but everyone left them to themselves.
After a few days the older cowboy had made arrangements for a couple of the other cowboys to join them one night. It appeared that the cowboy had tried to fuck the young guy a couple times but had met with some resistance and it had not happened. On this particular night while the boy was sucking the cowboy the others came up behind them and stripped the boy and held him down while the cowboy took the boy's cherry ass. This was followed by the other two enjoying the boy's mouth and ass.
For the rest of the trip the boy spent most of the nights servicing the cowboys and was even seen at times during the day sucking or being fucked. He had apparently developed a love for sucking and being fucked.
The older cowboy told me he just didn't want me to find myself in a hopeless situation like the other boy. I looked down at the man's fly and noticed it was much larger than usual. I asked him if he had also enjoyed the boy's body. He said he had but only when the boy had approached him and wanted to suck his cock. There was a long pause and the man finally asked if there was anything I wanted to ask.
I stuttered for a second before I asked if he would let me see his cock. He didn't say a word as he started unbuckling his belt. When his pants dropped his naked cock sprang forward through the fly in his underwear. I gasped since it was the first cock I had seen other than my own that was hard. Most of the skin was pulled back over the head with only the piss hole showing through. It throbbed and I noticed a drop of pre cum ooze out and drop to the ground. I started to reach for his cock but stopped when I realized what I was doing.
He told me to go ahead that he didn't mind if I wanted to find out what it felt like. I took the skin and slowly pushed it back as the mushroom head popped from beneath it's hood. He let out a low moan and I noticed his eyes were closed when I looked at his face. The look of pleasure on his face was too much for me as I slowly started jerking his cock for him. After a few strokes he started pumping his hips right along with my hand. I dropped down to my knees to get a better look when he placed his hands on my head. He applied a little pressure but was not forcing my head toward his cock.
I watched the pre cum oozing out and after a few seconds I had to have a taste since I knew the sweet taste of my own. I was not disappointed when I licked a couple drops off of his cock. The sweet taste was similar but a little stronger than my own and before I knew it I sucked the head of his cock into my mouth. He grabbed the back of my head and moaned as he slowly pushed his cock deeper in my mouth. When I began to gag he pulled back and told me to take it easy and I would figure it all out.
I sucked as much of his cock as I could back in my mouth and he started slowly pushing and pulling back and forth across my tongue. The feeling more than the taste had me very excited and my own cock was pressing against my pants. He started picking up speed and I knew he was getting close to shooting his load. He told me he was real close and if I were not careful he would loose it in my mouth.
I was not ready to take a man's cum in my mouth and as soon as I knew he was at the point of no return that I would pull back and jerk him off. I was really enjoying the feeling that I was causing him so much pleasure and was not ready when I heard the first grunt and felt his cock force its way further down my throat as I gagged on all the cum that erupted from his cock.
I pulled off and he grabbed his cock and jerked on it as it spewed a few more streams of cum that mostly landed on my lips and face. I got a taste of his salty cum and was a little surprised that it did not taste near as bad as I figured it would. He moaned a few times and slowed his jerking down as his cock went limp. He said he was sorry about shooting in my mouth but he couldn't stop himself in time.
He told me to stand up and drop my pants and he would help me get some relief that he was sure I needed. I didn't question him as I pushed my pants down and gasped as I felt his firm but soft hands grasping my hard cock. He jerked back and forth and I knew it wouldn't take but a few seconds before I shot my load. He grinned at me as he collected some of his cum from my face and reached down between my legs. He had me spread my legs as his cum coated fingers located my virgin asshole. I wasn't sure what he was doing but the feeling of his finger rubbing my hole and his other hand jerking my cock felt to good to have him stop.
My breathing was getting faster and heavier and I knew I was only moments away from my orgasm. He must have known it too as I felt a finger force its way inside me which sent some pain but a lot of chills rushing through my balls and cock. I had only managed to grunt once before I felt the cum rushing out of my cock and the pleasure overtook my entire body. My cock would erupt as my asshole clamped down around his finger and I would feel weak for just a second. I managed to shoot about seven times before my cock went limp.
I thought he was going to pull his finger out of my ass but he slowly rolled his finger around inside me. I spread my legs even further as he pushed another finger in with the first. I moaned as I felt my cock hardening again as he started fucking my ass with his fingers. He moved around and forced me to bend over as he kept pumping his fingers into me. He wiggled around until he had his underwear off and was standing right behind me.
I wanted to rise up when I felt the head of his cock against my asshole but he pushed down on my back and told me to relax. Just as I tried he rammed the head of his cock inside my asshole. I tensed up and tried to stand but he held me down as he told me to just wait a second and the pain would leave. He started pushing gently against me as the pressure forced my asshole to open and take more of his cock. He kept telling me how great my ass felt as he slowly worked his cock into it.
I was still feeling some pain but it was accompanied with a warm feeling and every now and then his cock sent chills through my ass and balls. It felt as if I was going to shoot at any moment. He reached around and jerked on my hard cock as he said he thought I was ready to really get fucked now. He grabbed my hips and without warning started pumping his cock in and out of my asshole.
The first few thrust was met with a little resistance but very quickly I started pushing and pulling along with him. His cock became very slick and was sliding in and out with ease and all the pain had vanished and with each stroke of his cock I felt like I was shooting a load. I could hear the slapping of flesh as he pounded himself against my ass. All at once I had taken all I could as I felt my second load of cum gushing out of my cock. I moaned with each jerk of my body but he never slowed down and even picked up the pace as he seemed to force all the cum out of me.
He let out a loud groan as he slammed himself against me and held me there for a second as I felt his cock pulsing inside my asshole. He did this a few times before he started a slow pumping and I felt his hot cum leaking out of my asshole. He pulled his limp cock out and leaned against the tack table in the room as he tried to catch his breath. I just squatted and let his cum and my ass juices run out of me. He asked if I was doing all right and all I could do was grin back at him.
As we dressed he said that he would do all he could to keep the other cowboys from getting at me since I was new to all this and they would probably get carried away. He told me that I should try to keep from making any movements that they could interpret as a pass or fancy for them. He also said if I decided I wanted to play around with some of them that I should let him know and he would set it up so I wouldn't be in any danger from the others.
We cleaned up and headed back to the bunkhouse but I was still horny and knew I would be enjoying the old cowboy many more times before this trail drive was over. Once we were underway he had managed to make sure that the two of us were on watch at the same time at night so I could suck on his cock whenever the cattle had settled down for the night. This didn't allow for much fucking.
After a couple weeks we came upon a town that had a couple saloons and whore houses. The boss had decided to rest the cattle for a couple days near by and had given part of the hands one day off to visit town and the rest of us the next night. The old cowboy told me to stay close to him and he would keep me out of trouble. We checked into a hotel room and ordered a bath, which we both needed. I got to suck his cock off while we bathed but he said he was saving my ass for later.
We first went to a little cafe and enjoyed some home cooking before leaving and heading to one of the saloons. He looked inside the first one but said it didn't feel too safe in it so we walked off to the next one. Once we entered he pointed to a table over in the corner of the room and said he would get us a beer. I sat down and was a little uneasy as I noticed some of the local cowboys looking my way.
John returned with our beers and told me to sip it slowly since he was sure I had probably never had any. I took a taste and really didn't like the warm liquid. He told me the taste would grow on me as he took a deep gulp of his. We watched as most of the men sat around drinking and playing cards while we finished our beer. I was only half finished when John got up and told me to finish mine off as he went to get us another one.
Before the second beer was finished I could feel the warm carefree feeling that comes from drinking and was beginning to enjoy it. John must have noticed a change in me as he told me that I should now slowly sip my beer so I wouldn't get sloppy drunk. I did as he said and we chatted a lot about the cowboys in the saloon and what we had been through so far on the trip. At one point I slipped my hand over on his knee and he quickly pushed it away. He explained that a saloon was no place to show any affection for another man. He then said he thought we had spent enough time in the saloon and should get back to the room.
I stood up and almost fell back as he grabbed my shirt and steadied me. He laughed and said my body was virgin to a lot of things. The other men halfway laughed as they watched John lead me out of the saloon. The fresh air felt great on my now hot flushed body. John told me to hold on until we got back to the room before I did anything that someone else shouldn't see. I giggled and thought it was real funny because I couldn't think of anything that should have made me laugh.
John managed to maneuver me up the stairs without making both of us fall. When we entered the room he guided me to the bed and let me fall. While I was lying on my back he removed my boots and pulled my pants off. I managed to sit up and remove my shirt as he undressed himself. I grabbed my cock and was surprised to find it was all ready hard and the beer was making it feel a lot bigger than it was.
John came over and as I reached for his cock he pushed me back and told me that there was plenty of time for me to play with his cock later. He pushed me all the way back upon the bed and then placed himself on top of me. His mouth was a surprise to me as it pressed against my lips. It was my first kiss so I didn't know what to do but as his tongue spread my lips I let it slip in and gently sucked on his tongue. Pretty soon I was returning the favor and was enjoying the feeling.
John's hands had started to roam all over my body and were sending trails of shivers everywhere they moved. I could feel his hard cock pressed against mine and wanted him to do more than just press against me. He raised himself up and started kissing my nipples, which was another feeling I had never experienced. After working my tits over he slowly trailed down my stomach and after flicking his tongue inside my belly button he moved on down toward my cock. I was sure he was going to suck or lick my cock but he went right past it and started sucking my balls into his mouth.
He put his hands behind my knees and spread my legs apart as he worked past my balls and was licking just outside my asshole. All of this was making my head spin and every time I reached to jerk on my cock he would push my hand away. I could feel the pre cum running down my cock and onto my belly. He stood up and pushed my legs back over my head, which spread my ass open for him and had it up in the air.
He placed his mouth right over my asshole and proceeded to kiss and suck on my asshole just as he had done my mouth earlier. My ass was relaxed and felt as if it was pulsing as he started pushing his tongue as deep as he could inside me. I felt the pre cum now dripping onto my chest as he lowered my legs and pulled me to the edge of the bed. He grinned down at me as I felt the wet head of his pre cum soaked cock at the entrance to my ass.
He slowly pushed as I tried to push against him and his cock popped inside. He moaned and lifted my legs higher as he pushed the rest of his cock in. I moaned and felt my orgasm building inside me. He pumped a few times but when he found his cock sliding with ease he picked up the pace. I felt myself getting closer and closer to shooting my load and I guess he could tell as he started slamming himself into my ass. I let out a grunt with the first blast of cum and John kept up his fucking until my cock stopped shooting.
He rolled me over on my stomach and had me get upon my knees and rest my head on my arms. He started with long slow strokes with his cock, which felt great as my body recovered from my orgasm. After a while I had started moaning and was fucking my ass back on his cock as he fucked me. He started picking up his pace and pretty soon I heard him begin to grunt and knew he was about to fill my ass full of cum. It only took him a few more strokes before his cock was swelling and empting his hot cum deep inside me.
"Is he ready for me?" Was what I heard from someone else in the room. I looked back and noticed our boss removing his clothes.
John said I was stretched good and filled with plenty of cum that would help me take on his big cock. I turned in time to get a good look at the boss's cock and even thought it was not any longer than John's it had to be twice as thick. He grinned at me and told me that he would take it easy until I was stretched properly.
He rubbed the head of his cock around my asshole as he collected as much cum as he could on it before pressing it at my little opening. The pressure was building and just when I thought my ass would rip open, the head popped inside me. I gasped and my sphincter tightened around his cock. He slapped my ass and told me to just relax. He pushed some more but my ass was not cooperating as it refused to ease its grip on his cock. He told John it looked like he was going to have to break this ass in even more. With that said he grabbed my hips and with all his might rammed his cock all the way inside me. I yelled out but quickly buried my face into the bed. He slowly pulled his cock back an inch or so before ramming it back inside me. With each thrust the pain became less and my ass seemed to open up even more.
Once his cock was sliding in and out he said he was ready to do some riding as he started pumping real fast. At first I figured I would just pass out but then that great feeling took over and I was racing toward another orgasm. When I did cum the boss said I would do that a couple more times before he was ready to feed me his seed. He was not lying as almost immediately after cumming I felt the pressure building up again. I shot or at least tried to shoot two more times before the boss jerked his cock out of my ass and spun me around.
He ordered me to open my mouth as he pushed the head of his thick cock into it. I could taste John's cum and my ass juices as he started jerking on his cock. He was grunting within seconds and I felt John pushing his cock in my ass.
"Here it comes!" Was all the warning I got before my mouth was flooded with cum. I had to swallow to keep from chocking and managed to swallow most of it. Just at that time I felt John shooting another load up my ass. The boss slowly milked every last drop of cum that he could into my mouth before pulling his cock out and letting it swing down onto his balls. He told me to move over as he crawled into the bed beside us and we all three dozed off.
I was awakened several times during the night as the boss and John took liberties with my ass and mouth. The next morning the boss got up and told John to be sure and have me back with the heard before sundown. John said he would as he rubbed his hand across my chest. John spent the next hour fucking me some more before we got up and took a bath.
We made it back to the heard well before dark and John had told me that the boss would probably be visiting from time to time until the job was finished. He wasn't wrong as the boss made sure he found some trail or canyon to check out with me just about every other day. My ass had become use to his thick meet plus he had managed to pick up something that made his cock real slippery. For the last month of the trip my ass had become well acquainted with the boss's cock and I was still sucking John off when we found the time.