A Silly Little Cowboy Story

I saw him from across a bar on Halloween. He was dressed as a cowboy, the most stereotypical one you could think of. And I’ll be damned if I wasn’t attracted to him instantly. There was always something about the imagery of a cowboy that caused a stirring in me. It just seemed like the ideal of old-timey machismo, something that “real men” should aspire to. I aspired to it in my own way I suppose; all those days I spent playing cowboy when I was younger led to me lusting after them now. You could say that the image of a cowboy was a big part of my gay awakening.

I was dressed as a man from an older era, circa Victorian, but I wasn’t going for accuracy. Really I’d wanted to dress as a vampire, but my boss said that we could only dress as something that wasn’t too distracting to the patrons. Working at a gay bar as a waiter sucked sometimes, though if it gave me the chance to meet studs like this, I wasn’t going to complain too much.

I approached him shortly after I sighted him. He was by himself. “Hello sir.” The formal address was partial for my character, and partial because I felt a slight thrill at calling this attractive man sir.

“Howdy partner,” he said. His southern accent wasn’t particularly strong, but I could tell it was real.

“What would you like sir?”

I saw his mouth shift in thought. It made me take even more notice of his facial hair. He had an 80s porn mustache with stubble covering the beard area. This wouldn’t be hot to everyone, but it certainly was to me. Another one of my “things” I guess. “Just gimme a beer boy. Whatever y’all got that’s good.” Boy…he’d called me boy. I wanted him to say it again as soon as it was out of his mouth. The word sounded so hot on his lips.

“Yes sir.” I went to retrieve it as quickly as I could. After checking on my few other tables, I returned. When I did, I saw he had leaned back and casually held his arm on the top of the booth. “Here you are sir.”

“Appreciate it.” He took the bottle from me.

“Will there…be anything else sir?”

“Yeah, sit a spell,” he said, taking a sip.

“You’d like me to…sit, sir?”

“Ain’t that what I said?” He gave me a look, seeming to read my trepidation. “Don’t be scared boy, I ain’t gonna bite ya…’less ya like that.”

Was he actually flirting with me? I thought I must be dreaming for a man like this to even be talking to me, let alone coming on to me. Still, if it was a dream, it was a damn good one and I didn’t want to wake up. “Okay sir.” I moved to sit across from him.

However, he had other plans. “Nah, come sit next to me.” His tone wasn’t forceful, but I could tell he wasn’t asking. Even if he was, I would have done it. After I sat down and he finished another gulp of his drink, he spoke again. “I’ll be a straight shooter with ya. The beer ain’t the main reason I came here.”

“What do you mean sir?”

I felt his hand, the one that was on the booth, fall to my shoulder. “Well boy, I saw you lookin’ at me ‘cross the bar…” He pulled me closer to him. “And I thought ya might like to come with me and I could teach you to” -he looked down to his crotch, then back to me- “ride a horse.” He put his lips very close to my ear and lowered his voice to a whisper. “How’s that sound boy?”

I shuddered at his offer. This man was everything I wanted. He was pushing all of the right buttons, all of the ones that made me a mess. “That sounds like…a dream come true sir,” I said, my voice heavy and breathy. He said nothing in response, only smirked. He had me. He knew that he had me and he’d known that from the moment he saw me across the room. “What’s your name?” I only then thought to ask.

“It don’t matter boy,” he responded. “Tonight my name is sir and your name is boy. Got it?” I nodded. “When are ya done here?”

“I get off in fifteen minutes sir.”

“Well, suppose that’ll be when I get off too. Now…get back to it boy.” Only now did he move his arm from around me.

I moved like lighting the next fifteen minutes, quick and erratic. My head was swirling with all of the thoughts of what I’d get to do later. I needed to be done with my shift as soon as possible. Finally I rushed back to where Sir was sitting.

“I…I’m done sir.” I said, short of air.

“Breathing heavy for me already, are ya?” he joked at me. I loved how he teased me…I could absolutely feel myself blushing as I smiled. “You embarrass easy boy. Cute.” He stood from the table. Only then did I realize how much taller he was than me. I knew he was big, but not that he’d absolutely dwarf me. I swore this man would be the death of me if he kept getting hotter, but I pushed on through. “I got my tab settled with someone else.” He put his arm around my waist, tightly. I was his tonight and everyone would know it. The way he held me all but said that he would be destroying me. I could do nothing to escape his thrall now, not that I wanted to. I was his. “Let’s go.” It was an order, not something you responded to, so I said nothing.

As we exited the bright lights of the bar for the relative calm of the night, he spoke again. “Got a car boy?”

“Umm, n-no sir. I take the bus to work.” I said, still trying to wrap my head around what was happening. My whole body was excited for what was to come, but I couldn’t help being nervous as well. This man had me under a spell and he knew it. Would he use that opportunity to take advantage of me?

“Let’s get us a ride then.” He pulled out his phone and deftly navigated through ordering a car to our location. It somewhat surprised me, as I thought he might have been the type to not have experience with technology or even to not have a phone at all. Perhaps he was usually a different person than he was portraying himself as on that night. But I ignored that thought, wanting to be completely taken in by the fantasy he’d created.

A car arrived for us shortly. I don’t remember the details of the car or driver’s appearance, but the person was nice enough as we got in the back. As I told them my address and the journey began, I noticed that Sir hadn’t once stopped touching me. He wanted me to always be feeling him, to know his touch and presence. Shortly into the ride, his hands lowered. His fingers began to toy with my waistband, lifting it, then lowering it. That’s the most he did, and it drove me crazy. I needed more.

After l looked to see that the driver’s eyes were firmly on the road, I moved forward a bit, signaling that he could have more access. Silently taking the message, his hand pushed into the back of my pants. His fingers drew under the edge of my briefs, slowly rubbing my skin. I lifted myself slightly off the seat, in case he wanted to put his hand inside. Instead, he took the opportunity to hook his fingers under one side of my underwear and moved it between my ass cheeks. He then repeated this for the other side. Before I understood what he was doing, he yanked up on my waistband, creating friction on my hole. I stifled a gasp, to which he gave an amused snort.

His hand came out of my pants and returned to my waist. He gave me a look, one that told me to keep my underwear as he’d put them. I finally understood that I’d done exactly what he’d wanted; he wanted me to show I was submissive to him, for me to do something that told him I wanted it. When I scooted forward and lifted my butt, those were signs to him that he could further dominate me, that I in fact desired to be dominated by him. That left me there, underwear flossing my ass, the constant pressure reminding me who was my master that night and making me think about something else rubbing between my cheeks. I was rock hard for the rest of the ride home.

After what seemed like an eternity, we arrived at my home. The fare was paid immediately and we were wished a good night. I think the driver might have known what we were about to go do. In fact, I’d be surprised if they hadn’t known.

As soon as I unlocked the door and we were inside, he slammed it closed. I looked at him just in time for him to lift me by my ass and push me against the door. His mouth found mine and his tongue shortly invaded it. I wouldn’t say we kissed, I would say he made out with me, grinding against me all the while, and I took it. I wrapped my legs around his frame as well as I could, so I could have more contact with him. Now that I was more stably attached to him, he moved his hands to my back and held me tightly against him. My own hands were laid over his shoulders.

I felt him touch between us, fiddling with the buttons on my shirt. He shortly decided that was too much to bother with and tore it off of me, as I vaguely heard a few buttons drop to the floor. I shook my arms, letting the shirt its self drop as well.

“Mmm, so eager boy,” he purred out between assaulting my mouth. “So willing to do what I want.” He pulled the waistband of my briefs again, reminding me of what I’d done in the car, that I had already wordlessly submitted to him. “I’m gonna fuck you like never before boy. Your ass ain’t ever gonna be the same.” I could feel his hardness below me and I knew he wasn’t lying to me. “I like boys like you. Ones that do as they’re told…that submit without even having to be asked…that know their damn place when a man like me walks in. Good boys.” He stopped kissing me as if to emphasize his next statement. “That’s what you are…a good boy.”

I can’t describe the thrill I got when he called me that. “Yes sir!”

“Say it.”

“I’m a good boy sir.”

“Good boys are the only ones that deserve my cock. I want you to know that. You’re one of the lucky ones.”

“Yes sir. I am sir!”

“You ready to see my cock boy?”

I figured this might be a test of sorts. “Only you decide if I’m ready Sir.”

Sir chuckled at that. “I like that answer boy. Get naked and get on your knees.” He put me down and I scrambled to complete his request. My clothes flew in all different directions. As I got to my underwear, he said “Leave those on boy.” I nodded and descended to my knees. “Good boy. Spread your knees out.” I did as I was commanded. Sir approached and put one foot behind me, between my legs. As I wondered what he could be doing, he leaned me back using a hand on my head. After my back bent a bit, he joined his free foot with his other one. Our legs tied together, his bulge was tantalizingly close. I wanted to put it in my mouth immediately, but knew I shouldn’t. So, I awaited an order; however, it did not come. I looked up at him and he simply started back at me.

Suddenly, I realized this was another situation like the one in the car. I had to show that I wanted him. I reached up to touch his bulge, but he stopped me from doing so. Failing that, I decided that I should use my words this time. “Please sir. Let me see your dick. Let me suck it until you tell me to stop. Let me take all of your real man cock into my mouth and choke on it. Please sir.” He nodded down at me, a sign that I could continue. I brought my hands up again and this time he didn’t stop me. I undid his belt and he pulled it off for me. Then I unbuttoned his pants and zipped them down. He pushed the pants down and they fell. Last were his underwear, which I slowly pulled off. A massive dick popped out and hit me in the face. “Wow…” I was truly awestruck.

He drug his prime meat across my cheek. “Betcha never seen one like this up close boy.” I shook my head. “That’s right. There ain’t anyone that measures up. You’re lucky as fuck. Boys would line up ‘round the block just to be my cum dump. But here you are. I chose you and you get to be even more that. You get to submit to me fully.” He slapped his rod against my face. “So, since I chose to give you my cock, you’re gonna take it without complaining. Understand boy?” I nodded my head. He grabbed the back of my head by my hair, firmly, but not so much that he’d rip any out. “Open wide,” he ordered. I did and he rammed his length down my throat. I gagged of course, but didn’t care. Sir’s dick was in my mouth and I was going to pleasure it.

Just as when he’d kissed me, I don’t know how much I actually sucked his dick. Sir was moving my head and his cock apart, then jamming them back together. I felt more like a passive player in this, just a hole for my Sir to use, but I wouldn’t complain about that. Plus, I was using as much tongue as I could to give him even more stimulation, so I wasn’t doing nothing. He clearly enjoyed it, moaning as he went along.

“Burn that dick into your mind boy.” He said as he continued to use me. “Memorize every little nook and cranny.” A thrust. “Feel the veins riding over your tongue.” Another thrust. “Remember how it feels sliding down your throat.” Thrust again. “And when you’re jerking your dick-“ thrust once more “-you‘ll think back to this. And you-“ thrust “-will-“ thrust “-cum-“ thrust “-for-“ thrust “-me!”

Now I was the one moaning. He wasn’t telling me that I should think back to this, no, he knew I absolutely would do just that. He was certain that this would be my jerk off material for a long while to come…and I already knew he was right.

I needed more, so I knew I would have to reassert my submission to him. Not being able to speak or move much, I looked up at him, my eyes wide and pleading.

“I know that look. You want this up your ass, eh boy?” I nodded. “Well, I can do that on one condition. I’m gonna shove this dick down your throat and hold it there for ten seconds. If you make it to ten, I’ll let you have what you want.” Without so much as asking if I agreed, he did as he said he would. He held my head firmly against him, his entire length in my mouth and throat. “One…two…three…” he began counting slowly. I tried to focus on breathing steadily as he further said, “Four…five…six…” I could tell he was counting very slow on purpose. He wanted to know just how much I would take, if I truly wanted all he could give. “Seven…eight…nine…” he very clearly waited a few seconds. Finally he released my head and pulled out. “Ten.” Before I could do anything, Sir lifted me by my armpits and spun me around. He pinned me against the door again and pushed down on my back, so that I arched it and stuck my ass out.

“I…don’t we need-“

“You want my cum up your ass, don’t you boy?”

He was right, I did. “Yes sir.”

“Good. Get ready, cause you’re in for a wild ride.” He released me from my underwear, giving me a momentary relief, before a giant dick was in my ass. I screamed as pleasure and pain combined. Sir kept one hand on my back, pinning me to the door as he roughly pushed his cock into my hole.

“Aaah…ah!” I gasped out. As if by wizardry, he was hitting just the right spot right out the gate.

“Pushing your button, am I boy?” He delivered more thrusts to the same area, as I made an even louder sound. “Yeah…right there…right…there! Push…push…push that button!” he yelled in a raspy voice. He was really getting into it. “Scream for me!”

I couldn’t help but do what he asked, in both a literal and metaphorical sense. I was seeing white as he plunged into me again and again. By this point the pain was gone; pleasure overwhelmed me. I was in such a state that I couldn’t even think to cum. I wanted to stay as I was forever.

Sir removed his hand from my back and used his body to hold my entire body against the door. It was cold, but it didn’t matter. I couldn’t feel it. My face had gone to one side. Sir grabbed my face without ceasing to fuck me and mashed it against his own. That was all it took for me. I exploded as I panted. Cum coated the door, the wall, and my body.

But Sir didn’t even slow down. “Don’t move boy. I ain’t done with you yet. I’m gonna put my seed in this hole,” he leaned forward and bit my ear, somewhat shocking me, “and you’re gonna take it.” I kept on moaning, my cock already hard again. “Still hungry boy? Fine,” he said as he grabbed my dick, “let’s milk you for all you’re worth.” I already felt close to releasing again. I didn’t even know that was possible.

With both Sir’s hand stroking my dick and his own rock on my ass, the pleasure moved to a whole other level. I thought I must have gone straight to heaven. This was an angel fucking me. Lost in my feelings, I don’t know how long it was until I came again, but it wasn’t long.

“Load number two. I wonder how much cum I wring get outta you boy.” He was silent for a moment. “We’re damn sure gonna find out.”

Again, I have to say I don’t know how long this went on. He fucked me for what seemed to be an eternity, making me drop all my cum.

Finally, he said, “Alright boy, it’s time. You’re gonna get my cum. You ready?” I weakly nodded. “Here it is…here I…cum!” His load filled my ass, making me feel full. He just seemed to keep shooting and shooting, just like a good cowboy. Eventually, he stopped. Suddenly, everything was over. He tapped my ass one last time. “One hell of a session that was boy. Thanks.” He pulled out.

I fell to the floor. “Thank…you…sir…” I said, breathing heaving.

“It’s what I do boy.” He looked at me and laughed. “You’re spent, eh?” I nodded. “I can see why. You just kept cumming the more I fucked you. You may wanna give your dick a rest tomorrow. Here, since I made you like this, let me take you to your room.” He picked me up and I told him where my room was. He walked in and put me gently on the bed. It amazed me that the man that had fucked me so wildly just a bit ago was now so considerate.

I fell asleep quickly. I don’t know if Sir spent the night, but I woke up to find that he’d left. I was still naked and I could still feel his load inside me. Even despite his suggestion, I knew I wouldn’t be able to give my dick a rest that day.

I saw a note on my side table. “Thanks for the hot night boy. I’ll remember you,” it read. Then at the bottom, “P.S. don’t leave your phone password on your desk.”

I was confused as to what he could mean by that, but as soon as I turned my phone on, I got my answer. My lock screen was now a completely different picture. Not of Sir, but of his massive hard dick. Yep, there was no way I was giving my dick a rest. I was embarrassed, even though no one else had seen the picture. I did of course change it back, but the picture was still in my photos. Even now, I still haven’t deleted it.

To this day I haven’t seen Sir again. That disappoints me obviously, but there’s a part of me that appreciates it. Part of the intense attraction in our brief encounter was the unknown aspect, the mystique of a sudden hookup. He was just a strange cowboy that came into my life, gave me some of the best sex I’d ever had, then went on his way. And now I could look back on that experience and have some of the best jerk off sessions of my life….just like he knew I would.