As always, this is a work of fiction. All characters are 18 or older and you must be 18 or older to read it. Do not do things like this, or anything less than fully consensual, in real life and always use protection.
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Tommy's First Cattle Drive
Tommy Wilcox couldn't believe his luck. Sampson Rider's crew lost their newest member on their very first stretch of the cattle drive. The boy just took off in the middle of the night, not even bothering to stay long enough to collect his first ten dollars. Tommy would never be that stupid. Ten dollars was more than his dad made from their last three hunting trips combined. And Sampson himself offered Tommy the job. Ten dollars a month, all the gear and food he needed, plus his very own horse, and a bonus once they made it to Abilene. It sounded too good to be true. His whole life was gonna change. And it did. Before he left, he went to the general store in town and got himself everything on the list. Chaps, new pants, boots, a shirt, bandana, cowboy hat, everything. It was the first store bought clothes he had ever had. And then he joined up with the rest of the crew. It took him an hour to get to the camp and it was dark when he arrived. Sampson greeted him at the camp on horseback. He was probably fifty or sixty or something, but strong looking. He had on dust and dirt covered brown pants and chaps, a rust colored shirt, blue bandana, tan suspenders, a leather belt, a black cowboy hat, and boots that looked like they were made of snakeskin. He was probably seven or eight inches taller than Tommy and outweighed him by at least a hundred pounds. Tommy couldn't see his hair under the hat, but he had dark stubble all over his face. He looked at Tommy and said, "Look at you, barely 18, and a cattleman. Get to bed, son, we got an early morning!" Tommy set out his pallet and fell asleep staring at the stars.
Sampson
I figured we had gotten just about far enough from the kid's house that he wouldn't sprint off if we had a little fun with him. And then the river just made my mind up for me that tonight was going to be the night. I ordered him to clean up in the river and said the rest of us had bathed before we left the boy's town, about a week before. Wasn't true, but it made sure the kid was clean before bedtime and gave us all a sneak preview. I watched him myself for at least ten minutes, giving my johnson a chance to firm up real good. The boy was 18, but not shaving yet and with not a wisp of a chest hair. Not much hair anywhere else either. His ass looked smooth as a babies. And, unlike the last boy, he was petite too. The boy was 5'4 at most and probably a 100 pounds sopping wet. He had decent long brown hair too, almost to his chin. Billy Jackson saw me watching him and asked, "We breaking the boy in tonight?" I shook my head and said, "Don't want another runner. I'm breaking him in. Give this one a few days before everybody gets a ride." Billy spat out his tobacco and looked a little angry, but he still said, "Your choice, sir, but the boys are eager." I nodded and gestured for him to walk away.
Tommy
I was cold under the blankets. I had on the thick long pajamas Mr. Sampson had told me to buy, but they weren't enough to keep me from shaking. I couldn't fall asleep I was so cold. The pitch black was also a little scary. I could hear coyotes or something howling and I wasn't sure what I'd do if one attacked. And then I felt my blankets being lifted and someone crawling in next to me. I could smell him before he talked. Whiskey and cigars and sweat and the stink of the road. Mr. Sampson said, "I've been waiting a whole week for this, son." Then I felt his cold meaty hands around my waist, pulling down the pajamas pants. I said, "Sir, it's cold." He said, "Remember what you said when you wanted this job, son? You'd do whatever I needed and make sure I didn't regret hiring you?" I whispered, "Yes, sir." Then he said, "So just relax, son, and stay quiet unless you want the whole crew taking a turn."
Sampson
I crawled in naked under the blankets and had the boy's pajamas down in less than a minute. I enjoyed the feeling of my johnson against his little butt for a minute before flipping him onto his belly and climbing on top of him. Then I leaned real close in and told him, "Stay real quiet, boy, just take it like a man and it will be over soon enough." Then I spit in my hand, rubbed my cock real wet, and pushed in his tight little butt. And it felt good. The last kid's butt was tight, but hairy. This one's butt was smooth on the outside and silky wet velvet inside. I couldn't hold back, either. In three thrusts, I had my cock buried up to the balls. His whimpering was a turnon, too. He wasn't fighting me at all, just tense and whimpering real quiet like. I started whispering into the boys ear as I fucked him: I'll work you hard, boy, but real men need to juice a cunny or they get ornery. That's what we got you for now. I'll protect you for a few days and teach you, kid, but then it's open season on your little body. Just relax and take it like a lady.
Tommy
I gasped when his dick went up my butt. It hurt, but I knew real men didn't cry. I tried to stay quiet, but even biting my lip I started whimpering. My whole world became the weight of his body on top of me and his cock breeding my butthole the way our hunting dogs bred each other. I whimpered like a puppy as his sweat dripped on my back and he started drooling on my face as he thrust into me. His beard scratched my face as he grunted and shoved harder. And his dick hit something up my butt. I felt myself leak a little out of my dick. And then he grunted and slammed harder again and more leaked out. It hurt, but felt good too. I moved my butt up into his dick, trying to get it deeper, and he laughed. He grunted, "Guess I ain't got to play nice, kid." And then he lifted up his body and slammed it down into me. Hard. My eyes started watering, even as my dick got hard.
Sampson
I preferred a lady any day, even an old loose whore in some cheap saloon. But this kid was tight. His pants had been hiding a real tight butthole that sucked my dick in and squeezed it like a satin fucking glove. But when he started pushing back against my dick, I almost lost it. We had had twenty of these young cowhands by now under us. Most ran. Some just took it the way a man took a whupping. This was the first to shove his ass back for more dick. Sampson had heard there were men who liked it. But all the ones under them so far had just cried and took it. Until now. He reached his hand around to feel the boy's johnson and it was hard and slimy. He let go of the boy's dick. Then he pulled the kid up to his hands and knees, spit in his own hand, and started jerking the boy while he fucked him. He saw his men watching and knew they all wanted a turn.
Tommy
I was still crying. His dick up my butt hurt. It was like a metal rod jamming up me. But it also felt sort of good. When his hand gripped my dick, I could feel myself almost giving it up right then. Then he pulled me up and started really fucking me the way our hounds fucked. But with his hand jerking me. And I couldn't help it. My dick was leaking more and more and then it was building up and then it exploded. My dick shot out jizzum once, then again, then again. It was so intense with him up my butt I could feel my hole squeezing and letting go. And then he groaned on top of me.
Sampson
When his butt clenched around my dick, it was all over. I felt my johnson flood his butthole and just collapsed on top of him. I lay there for a minute, enjoying my dick softening up his hole, and then I pulled out. I got dressed while he watched. The other men were awake. I could see a few pulling on themselves. But I was saving his butt for myself for now. Some of the cattlehands were big enough they might ruin it. But I also I couldn't risk mutiny. I announced, "No cornholing the boy without permission or I'll have you whipped. But his mouth is fair game." Then I went back to my pallet to sleep. We had fifty hard miles to cross tomorrow.