On a weekend trip with a few friends from college it was decided, after much consternation on my part, that we would all go horseback riding that Saturday afternoon after we had arrived at our cabin getaway in the Great Smokey Mountains. I personally was opposed to the idea because well, I had never ridden a horse before, and I wanted to see the sights, and at the very least go hiking with my own two feet.
I had only recently met these guys at the college job fair earlier that semester, and we hit it off when it was discovered that we had all three come from the same area. They were both Juniors, and they seemed to be the best of friends. They were always together, and they were both funny as hell. John was a tall and athletic, with short dark brown hair and an average looking Irish face. He wore glasses, and played dumb about most issues, but I knew he was smart because he was in a special program for aspiring NASA scientist. Rick was short and a bit more rotund, with a wild looking blondish red hair, often wearing a baseball cap and sporting a big burly beard. He was always playing pranks and keeping John on his toes. Both reminded me of guys from back home, and when we met, we immediately hit it off as if we were long lost friends.
Only in my freshman year of college, I had been on a full-time schedule while waiting tables on the weekends. I still had my clean-shaven face and my Irish good looks, but I felt I was maturing somewhat. Standing at 5’ 11’’ and keeping myself fit going to the gym and bicycling to and from classes, I was determined to maintain my bubble butt even though I was thinning a bit, and my aspirations for sex had gone out the window with my busy schedule.
In fact, I had not come out in the college scene. My interest was purely in older men, and when I met John and Rick, I didn’t even feel compelled to tell them what my bedroom proclivities were because neither of them interested me, and besides it was nice to have regular friends to goof around with.
John and Rick invited me out to a local dive bar after the first time we met. We drank beers and played pool and laughed out asses off the whole time. After that we started texting in a thread to each other. Mostly funny memes and raunchy humor.
One day John and Rick mentioned getting a cabin in the Smokeys for an upcoming weekend, and I stayed quiet. It was nearly impossible to take time off work and school when I could barely afford rent. John and Rick met me after work that next Saturday and drove me to the bars. The weekend mountain trip was brought up again that night after I had had several drinks, and I eventually agreed when they insisted that they were already paying for the cabin and gas, and all I had to do was provide my food and beer.
I apprehensively marked myself off the schedule at work for that next weekend and threw caution to the wind. Having dudes to hand out with and do normal dude stuff was appealing to me. We had all grown up in the south, from middle class rural white families, and it just seemed like a natural adventure for a college boy to go on. Besides I had never really been able to experience the Smokey Mountains as an adult. My mother and I had gone when I was a kid, and I had only remembered the doing touristy stuff.
When we took off that Friday, I had skipped a few classes and was already feeling guilty when the two assured me that it was going to be a fun weekend and that I would be glad that I had come along. The whole way Rick made me laugh telling stories about John and the stupid shit he had done. John would always have a hilarious comeback as if he had no clue why it was so stupid, turning it around on Rick as If he had missed the whole point. I just laughed and laughed. There was never a dull moment with these two.
When we got close to our destination and we started to see the beauty of the mountains, a discussion about our options for weekend activities begun. John mentioned zipline and ATV rides, and then Rick mentioned horseback riding. I was not comfortable with horseback riding. It didn’t seem like the best way to spend a Saturday, riding on a sweaty horse and being scared shitless the whole time. Both John and Rick seemed to disagree, and they spent the next thirty minutes trying to convince me that it would be fun.
After I had been worn out on the subject the car went silent and we drove through the mountains pointing out attractions and mesmerizing places as we headed towards our cabin, stopping on the way for another hilarious adventure in a local grocery store to get beer and food.
When we arrived at our cabin, we had to double check the address a few times because the place was so big. It had a big wrap around porch and several bedrooms, and a big stone fireplace in the middle. A nice size set of brown sued couches adorned the room. We sat out groceries on the big island counter and walked around the whole place ‘oohing’ and ‘ahhing’ as we picked out our rooms.
When we finally settled in, we popped some beers open and cheersed each other from the couch. John had discovered a jacuzzi on the back patio area and we all went out to look at it. This place was beautiful, and we could only see one other cabin adjacent to us on the small winding road. We drank several beers and sat in the jacuzzi until I was conked out from trip. I went to bed early partially dreading the next day, but I knew whatever we did it would be fun. John and Rick had a way of bringing out the best in me, and I slept like a baby on the big queen size bed.
The next morning, I awoke to birds chirping and the sound of bacon sizzling. When I walked out into the spacious main room, John was cooking us up some basic country fair, and Rick was sitting on the couch engrossed in his phone. They both greeted me, and we ate our breakfast sitting on the stools that lined the big kitchen island.
“You ready to ride some horses?” Rick asks me with a mouthful of bacon. “Yeah, I guess so” I answered, still noticeably unenthusiastic. “Come on, it won’t be that bad” John chimed in. I gave them both a slight grin wavering to the twos assurances as they both patted me on the back and made wild grunting sounds in unison.
The incredible views on our drive through the mountains washed away most of my nervousness, and when we drove down a country driveway to a set of large stables that were surrounded by an incredible mountain scene, I was starting to get excited again.
When we got out of the car and walked around the barn, we were greeted by a very handsome cowboy named Bill, that insisted we call him Mr. Bill. He was about forty or so with just enough stubble on his face to drive me wild. He wore a tucked-in denim shirt and denim blue jeans with the trademark belt buckle, and he had on brown cowboy boots, and a brown cowboy hat to match, under which was a bit of longish brown hair trailing behind his ears. He was the quintessential rugged man of my dreams, and he beamed at us with earnest big blue eyes.
While he explained to us what we would be doing and how we were to follow his lead, and how we needed to always listen to him, I stood there gob smacked trying not to think about what I would rather be doing as I watched him lead our horses out of the stables on by one.
When he helped me onto my horse, I felt his touch on my leg and I nearly melted. ‘What a stud” I thought. His piercing blue eyes looking into mine as he steadied the horse and gave me directions. John and Rick were goofing around as per usual, and I was transfixed on Mr. Bill. He seemed to take to me, and when we rode out, I followed close behind him on my horse watching him in the saddle. Wishing I was that saddle.
Mr. Bill started to talk to me exclusively as we made the decent into the trails. He asks me what I did, and I told him I was in my freshman year of college and that I was waiting tables for money. He seemed to be a little more than interested in me, to the point that when we took a break in a large clearing to wait for John and Rick, Mr. Bill ask me if I had ever gone camping before. I said that I had grown up in a rural area and I had camped a bunch growing up, and he seemed surprised. “You don’t look like the type” he said looking at me as we both sat on our horses facing each other. “I don’t?” I said coyly, realizing this unimaginably hot cowboy was getting friendly with me. “What’s with these guys? One of them your boyfriend?” he said with a smirk. I couldn’t believe he had said that, and I didn’t get a chance to answer because at that moment John and Rick came riding up through the woods behind us.
As we made our way through the trails, all I could think about the way that Mr. Bill had made conversation with me. From the very first time he had spoken to me, he seemed to be only interested in talking to me, and John and Rick were oblivious to the whole thing.
When we stopped for a breathtaking mountain view on the final ridge, John and Rick both continued to goof around while Mr. Bill told me about how his grandfather had owned the land we were on as long as he could remember. He said that he had been camping on that very ridge dozens of times and I thought of him out there in the wilderness stoking a fire looking out over those mountains. It must have been an amazing childhood I thought. I also thought about the possibility that he might have been lonely out here growing up, and that if I was reading his signals correctly, he was probably still lonely, and man that made me hot.
Mr. Bill helped me back on my horse as we readied ourselves to ride back and he looked up at me and gave me a sexy rugged dimpled smirk like he knew what I was thinking.
We talked a bit more on the ride back down the mountain, and I eventually got around to tell him that John and Rick were just college buddies, and that they had forced me out there to ride horses, but I was glad they did. He didn’t answer me at first, but when we were out of earshot, while riding next to me he said that he was also glad I had decided to come along.
‘What the actual hell?!’ I thought, did he just tell me he was glad I had come along with those beautiful blue eyes like he was into me? And what about the camping questions? Did he want to invite me to camp with him? Like be outside all night alone with each other? I couldn’t stop thinking about it and when we arrived back at the stables we dismounted and John and Rick were asking me if I had had as much fun as they had, and all I could do was answer with “I loved it, but I think I might have dropped my wallet”
“You what?” Rick said laughing. “Why did you bring your wallet?” John said in disbelief. “I don’t know but I must have dropped it somewhere” I said patting my jeans. Mr. Bill came back from taking the horses into the barn to take off their saddles, and John told him what had happened. “Well, I guess we’ll need to ride out and look for it” he said without much thought. I was looking at him when he said this, and I could sense a hint of amusement in his eyes.
“Well damn, we can wait here I guess?” John said, “No way man that’s a long wait” Rick said and started towards the car. John looked at me as Rick walked away “We gotta get something to eat soon, or Rick will start foaming at the mouth” he said, and I looked at Mr. Bill for an answer. Mr Bill patiently leaned back against the barn lifted up a leg up and placed his boot against the barn to steady himself, and after a brief moment of silence, while I felt around my pants for my wallet for the hundredth time and Rick rifled through the car Mr. Bill spoke up “If you two want I could drive him back down to the cabin after we get his wallet, I’ve got to make a run into town later anyway?”
I nearly lost my composure when he said this, but I was going with it. This cowboy and I were about to be alone in the woods.
John looked at me to see what I thought about that, and I shrugged. “You still have the address on google maps?” John said seeing that I was ready to do what I had to do. I looked at my phone and nodded.
“Not much service up here, but I’m sure we can find it” Mr. Bill said slightly grinning at me as he stood up from his perch and started walking back into the stables to re-saddle up the horses, leaving us to work things out for ourselves. I gestured to Rick that I was sorry with a shrug of my shoulders when he looked at me from the car, gesturing back a ‘what the fuck?’ with his arms in the air as John started walking back towards him to tell him the plan.
I watched them both drive off down the long driveway, feeling my stomach knotting up as I thought about the situation I was in. Here I was at a desolate mountain ranch all alone, as far as I knew, with an extremely handsome older cowboy, and I was pretty sure he was feeling the same way I was about it judging by the looks he was now giving me as he brought out the horses and led mine over to me.
He helped me back up onto my horse and again gently gripped my leg as he put my foot into the stirrup. “You think you might have lost it on the ridge?” he said as he hopped on his horse with ease and then turned her around to face me. “Yeah, it’s probably there where we got off the horses on the ridge” I said thinking about it for a minute.
We rode back through the field we had just come out of and down the horse trail along the Wood line. “I’m sorry about this” I said, “If we can find my wallet, I can pay you for the extra trip” We were riding side by side and he answered back “It’s quite alright, I enjoy the company” now looking back at me with that dimpled cowboy grin. I nearly melted. Maybe I was crazy, but this was the best thing that could have ever happened to me, although I was still apprehensive to the possibility that might be thinking what I was thinking.
We rode back up a big steep embankment that led onto a higher wooded trail, and when we came to the clearing where he had made conversation just a few hours before, we stopped and rested the horses.
He turned his horse towards me rode up next to me “You think you might have dropped it anywhere around here?” he said looking around on the ground before leaning over and resting himself on the horn of the saddle, and then giving me a look I hadn’t seen before. It was like he was trying to read me. “I don’t think so” I said looking around the ground and trying to act like I hadn’t noticed.
“Well let’s get up to that ridge and look around and then we can stop and have some lunch” he turned his horse and started down the trail away from me, leaving me reeling at the thought of having a picnic alone with this guy. I honestly wasn’t sure what was going to happen. I mean he was getting damn friendly with me, but there was a chance he was just fucking with me, and at this point I had been making myself pretty obvious with the signals I was giving. He could have done whatever he wanted with me, and I would have eagerly complied.
As we came into the clearing at the ridge, the view seemed all that more amazing to me, and I started to feel that whatever happened this whole thing would be going into my spank bank.
We got off our horses exactly where we had earlier, and I looked around and immediately saw the missing wallet “Here it is” I said as started taking the horses over to a nearby tree to feed on some prairie grass. I saw him pull an old leather bag off his horse along with an old Mexican blanket and watched him lay it on the ground.
“Alright. Good deal. Here have a seat” he said waving me over as I watched him sit on the edge of the blanket take off his cowboy hat, and pull off his boots one by one. As I walked over I noticed my legs and thighs were aching like hell, I stretched a bit before nervously kneeled next to him.
He handed me a canteen of water and a food bar. “The best I got” he said as I drank the water thirstily while still on my knees. I eventually tried sitting down Indian style to graciously accept the food bar. I opened the food bar, and he sat back and opened his, and we both ate silently as we looked out over the vast mountain ranges that were visible in the distance.
“A far cry from the dorm room” he said to me as we nibbled our bars “It sure is” I said looking over at his body all muscular, his slicked back sweaty hair golden brown and long. I could see that it his tan line underneath his collar, and his face was wind worn. He lay back on his elbow and stretched his legs out, his jeans tight around his solid thighs, the white socks on his feet waving there in the wind.
He looked over at me and smiled as he laid on his back with his hands behind his head “I don’t often get a chance to lie around out here and enjoy the scenery” he said looking over at me with his hands still behind his head, watching me as I laid back, stretching out my legs and then leaning on my elbows next to him. “That’s too bad” I said looking over at him and thinking about how much I’d like to just cut to the chase and get this cowboy pants off. My dick started to harden in my pants at the thought, and I was prompted to sit up in order to hide it.
I turned over to look at him to see if he had noticed, and we both locked eyes. In that moment It was like he had heard what I was thinking, and his hands came from behind his head and he reached down to undo his belt buckle. He unzipped his zipper and sat up and pulled his jeans down, the legs going inside-out as he ripped them off and tossed them to the side, resuming is position laying on his side holding his head up with his left arm while rubbing his bulge, and then looking at me expectantly.
I kicked off my boots and then pulled my jeans off more easily than him, throwing them to the side, and lying back down on my right side to face him. I began to rub my hard dick through my black boxer brief underwear slit, and he reached over between us, and grabbed my inner thigh, and then pulled me closer to him.
I laid back and let him molest me. I could smell his cologne, and hear him breathing heavily as he stuck his hand into the leg opening of my boxer briefs to stick his calloused fingers up into my crack, touching my taint while I stroked my dick with my left hand. As he massaged my hot taint with his fingers, I reached over with my right hand to feel his manhood through his underwear. It was hard and thick, and a perfect length, and I fought my way down through his elastic band to get ahold of it while I opened my legs and let him probe my hot wet teen hole. I pulled away and reached down to pull off my boxer briefs and then remove my flannel and t-shirt while at the same time he was pulling his underwear and removing his denim shirt and undershirt.
Now fully nude I crawled back next to him and took ahold of his cock as he resumed feeling my sweaty wet hole between my thighs. I rolled him onto his back and took in the sight of this extremely hot man laying naked next to me, his chest hairs growing down to his stomach hairs, connecting to his pubic hairs. I followed the trail down to his musty crotch where I was holding his big thick manhood. It was pulsing in my hand when I gave it a thorough licking from base to head as I positioned myself below him, coming up between his legs, my knees in the brush and dirt. He laid back and put his arms behind his head and watched me as I looked up at him for approval. I put his whole manly dick in my young supple mouth and began to suck on it, still looking up at him. It was in my mouth for a few moments when he laid back and grabbed my head with both hands and moaned out an “Oh shit!” like he was about to come. I stopped, not wanting it to end, and I looked up at him arching his back, his heels digging into the ground, and his balls dangling there in a patch of delicious hair. He pulled my head up with both hands and I relented. I then slowly climbed up on top of him, kissing his stomach and then his chest as I I did.
He quickly rolled me off of him, and then laid me on my back before I could kiss him on the lips. He crawled on top of me and then got up on his knees in between my legs. He spread my legs wide apart, spit on his fingers, and then aggressively started feeling in between my young college boy buns, probing his fingers into my wet hole, as I laid back and stroked my cock watching his big strong arms come up next to me on both sides to brace himself as he crawled on top of me to work himself into me, my legs wide apart, my back arching as I let it happen.
Our eyes locked when I felt his dick tearing its way into my sweet young hole, and we both grinned at each other and started to giggle. He was looking at me like he had wanted to fuck me his whole life, biting his lip when it started to go in. I started burning from the lack of lubrication, and I grabbed both of his wrist that were gripping my sides, and started scooting back. He kept driving himself into me, and it started to go in more easily after a bit. I scooted up and off it, and then I turned over to let him the full view of my ass from behind.
The sight of my sweet bubble butt rising up in the air in front of him made him howl, and he smacked it as he got up close behind me, grabbing ahold of it with both hands and spitting on his dick before feeding it into my shaved smooth hole.
The blanket that was once underneath us was now crumpled up, laying way off to the left, leaving us on our hands and knees in the grass and dirt, my young limber body now stretched out face down and ass up ready to be broken. When I felt his dick going in me, I cried out, gripping patches of weeds, and feeling my face in the dirt. I lied there helplessly, feeling his manly hands squeezing my big round buns around his cock while he slowly pushed his mighty oak into my thirsty teen trap. It was at that moment that I finally knew what that saddle felt like.
He bucked me like a only a cowboy could, and after a few minutes my legs gave in, and I laid down all the way, my hard dick in the grass, my body itching and twitching as he drilled his cowboy cock into me, his sweaty body on top of mine, the stubble of his chin rubbing on my shoulder as he panted, grabbing both of my arms and squeezing them for support while he grinded his thick cowboy cock into me harder.
I felt him start to cum and I demanded that he cum inside me “Fill me up Mr Bill!” I moaned as he got back up on both hands and started to fuck my harder than before. I felt him seize up and then I felt his warm semen start to rush into my insides as he gasp, and then started to move it around slowly inside me, making sure he had released the whole load before pulling out.
“Damn son! That some seriously sweet ass you've got there!” He said, rolling off and fetching his undershirt to wipe his dick off. I rolled back over next to him and jerked myself off, cumming instantly while still covered in grass and dirt “Oh fuck Mr Bill” I said while I was cumming “That was so fucking hot!” He grinned at me and watched as I shot a huge load all over myself. When I had finished he tossed me the undershirt he was using, and I wiped up feeling a bit embarrassed that I was so not ready for what had just happened .
We both stood up sweaty and naked, and brushed the grass and debris from ourselves before getting dressed. If this was what cowboy life was like, I thought, then I was ready move to the country. I mean this was the hottest thing I had ever experienced. The whole thing. Hot older cowboys into young twinks. Sex outdoors. Horseback riding. I was hooked. How wrong I was to try to get out of this adventure.
After getting dressed and drinking most of our water, we mounted up and rode back silently, occasionally catching glimpses of each other, both of us grinning while thinking about what had just transpired. He now had the look of a rowdy teenager to me. So damn handsome too.
When he drove me home in his big pickup truck that afternoon, he told me that he had not ever been that intimate with another man before, but he had always wanted to. I ask him what made him think that I would go along with it, and answered that he knew that I had purposefully left that wallet out there when he questioned me on the ride to the ridge. “I just knew at that moment that you were wanting it as bad as I was”
We were at that moment pulling up to the cabin and I looked over and gave him a devious grin “Well it worked, didn’t it?” I said as he parked the truck. He reached over and grabbed my thigh and squeezed “It sure did, now you’ll come on back to the ranch and see me again wont you?” I scooted over and gave him a peck on the cheek, and then slid back over the other way to open the door and climb out. Before I closed the tuck door I looked up at him and I answered “Next time we’re gonna need a bigger blanket”. He gave me a big grin and waved me on, and at that I closed the big tuck door behind me. I walked bowlegged up the cabin stairs and waved back at him as he backed his truck out of the driveway. At that point I needed a shower more than you could imagine, and that Jacuzzi was going to come in real handy that evening, but the truth is I would have gone back out on that ridge and did it again if I could. The serious question now was how did I get myself into these situations? Well the only answer I can give, and Its one that you might have guessed by now, is that maybe, just maybe, I’m am just that lucky ;)
This is a true story. The names and places have been changed
