Date: Wed, 10 May 2023 13:42:17 +0000 From: Sam Tudor Subject: Road Trip to Cupcake Ranch/ Part 16 My numbering is getting worse, but this is really the 16th chapter, there being no 12. Now, I could write a 12 and fill it in, but I don't know how to fill it in, so just be happy that this is the 15th story, but numbered as 16. I need an 18 year old to guide my computer work. Meanwhile think of a contribution to Nifty, even as little as a Grande mocha latte with extra sugar at Starbucks. Second Night in Cheyenne Jeremiah and I were in a motel in Cheyenne on our day off. We were ranch hands for the summer, I was a college guy, 20, 6", 7" cut cock, blonde, athletic body, Jeremiah was bigger, white as can be, and really hung, we had seen each other naked in the bunkhouse showers, but, until the night before, had never played with each other; that was a 4 way with another couple in our motel room, but other than some after play we had still never made it with each other. We had both topped the other two guys, side by side over the edge of one of the beds. And, we were both tops, virgin holes, except for fingers and toys. We had talked a lot about bottoming, clearly it could feel awfully good if the guys we had topped were any examples but we were not sure we were ready to try it since we had also seen how much it could hurt, especially virgin holes. We got up with morning woodies, did a bit of grab ass, pissed, shaved, got dressed and went to the diner across the way for breakfast. Cheyenne is a pretty sleepy town in the daytime, it comes alive at night so we made the best of it. We went to the Frontier Old West Museum, and drove around a little, went back to the motel, hung around the pool, and then gave each other the look. "Let's go in, and see what happens," I said. We took off our bathing suits, and were both hard. "Come here," I said, and proceeded to kiss him on the mouth. He did not resist, but, on the other hand, he did not participate much. "I've never really made out with a guy," he said, "it has mostly been fuck'em and forget'em for me."' "OK," I said, "let's try. You've made out with women?" "A lot, back in high school." "Well, a kiss is just a kiss, follow my lead, I will show you how I like it done, and it can be better with guys than with women, just like fucking can be." And so, we did. I led the way I like it. Slow and easy, a little tongue play, more deep tongue play, some sucking on the lower lip which for some people, male or female is incredibly erotic. All slow and sensual. Meanwhile we were exploring each other's bodies with our hands, fisting two cocks, feeling ass, running a finger under each other's balls, feeling the holes, dropping down to suck on the pecs and nips, taking turns dropping further to lick cocks, balls, thighs. He was dripping precum, I don't have much, but my cock head was wet. "Whoa," I said, lets lie down and 69. We did. We sucked each other, I got even harder when I had his cock in my mouth, he was hard as a rock. "Take it slow," I said, "let's make it last, there is not a lot much else to do in Cheyenne in the daytime." "Time to clean out," I said, and got my bulb enema kit out of my bag. "Three rinses out to do it, but we rinse until it comes out clean." I lubed up the nozzle and his ass hole, and gently put it in, aiming at his belly button and then squeezed the bulb. He then shit it into the toilet bowl. Lumps of shit and water. Did it twice more, the last time it was pure clean water. He did the same for me, I was clean on the 4th try. I had some condoms and lube, and got them out of my bag. I greased up my hole and my right index finger and greased up his hole. "One finger at a time, easy, let's each try each other." We laid in 69 position, side by side, leg up, hole exposed, I got a finger in, very slowly, and felt him get one in me. It felt good, but then again, I had had this done to me, a lot. He tickled my prostate, and I felt his, about the size of a walnut in the shell, and round, I massaged it and could see that the precum really started to flow. I got another finger in, he moaned and said, "Hold a second, let me get used to it." "How many fingers do you have in me?" I asked. "Three," he said, "you sure you haven't been fucked? I got them in easy." "I am sure," I replied, "but, as I told you, I have had a few fingers and a few toys up there, but never a cock. Let's keep going, and maybe this afternoon will be the day." "Same here," he said, "but only a few fingers and a small sized butt plug, and even that was not easy for me to take. Once it was in, it was OK, but the initial push really hurt. You know Leroy, back at the ranch, it was his, he has a set of three, small, medium, and big, and sometimes he wears the medium all afternoon, says there is nothing like being on horseback with the butt plug in place." We continued to explore each other's holes for a while, all the while getting them loosened up and well lubricated. "OK," I said, "time to try it. Who goes first?" "Let's flip for it," said Jeremiah. We did. He won to be top first. I got on all fours on the edge of the bed, ass up, and got my mind and body prepared. I was going to lose my virginity, well, as a bottom anyway. He got behind me and put his big cock head against my hole, and pushed gently. It got past the outer ring, "Relax, push out, and breath in," he said. I did. Suddenly it was in. "Hold a minute", I ordered. He did. "OK," I said, he began to move, slow and steady. It felt like I had to take a shit, but I knew that was just the way it felt to some guys, having topped dozens by then. The more he moved the better it felt. My cock was only semi hard at that point, he reached around and played with it and it got fully hard. We fucked for a while, he said he was ready to cum, and I needed to, but we had agreed to switch up, so he pulled out, took off the condom, and bent over. I pushed into him, it went all the way on the first push, and it was great, as fucking usually is. He was moaning, and asking why he had never done this before. "Now I need to cum even more," he said, as he started to cum, hands free, just from being fucked, and not fully hard either. "Shit," he said, "that was interesting, and felt good, but not as good as when my cock is being played with." "On your back," I ordered, I pulled out, he rolled over and put his legs up, I got in, and fucked him hard while playing with his now slippery cock, between the cum and the lube, he got really hard, and he came again, that squeezed my cock, and I came hard, as far up his ass as my cock would go. It was great, I counted 14 spasms, each one shooting cum into the condom. We played all afternoon, trying different things we had heard about or seen on the net, went to the diner for supper, and back in the room, looked at some porn while we played with each other gently. I had to finish myself off, he watched me and did the same. "Rough day tomorrow on the ranch," I reminded him, so we showered, and went to sleep since we had to be on the road by 4:00 am to be back at the ranch for breakfast at 6. "I hope my ass is not too sore to ride today." It turned out that it was ok by the time we got to work at 7.