THE COWBOY WAY

Ralph Greco Jr

James had always been a bit cocky; he had reason to be with his clean-shaven, chiseled face, muscular body and successful accounting business. But mixing his usual bravado with his new interest in being a cowboy was proving an unbearable (for those who knew him) combination. I know friends are supposed to allow one another wide berth when it comes to one another’s idiosyncrasies; I had plenty of my own peccadilloes that James had had to deal with in the past (still dealt with), so I knew it was common to go through this with people close to you. But James’s suburban cowboy persona was growing to such proportions I was coming to regret the times we hung out and I had never done so in the ten years’ knowing him. This guy was one of my closest and dearest male friends, but I was becoming desperately exhausted and didn’t want to spend the next few months (possibly even longer) avoiding the guy. His “Yessum, ma’am”s, wearing his Stetson everywhere and the week-long Urban Cowboy marathons wouldn’t have been so bad if we lived in Texas, but in Connecticut it was a bit much.

I hadn’t though, with James dragging me “line-dancing” this night – me line-dancing! – and his cowboy b.s. was at an all-time high. After watching his ass as he walked from my car to his apartment – one of the few pluses of his new suburban cowboy attire was him wearing extra-tight jeans – I drove the ten miles back to my house entertaining my frustrations. As you sometimes do during even the shortest of drives, my semi-buzzed brain started to “buzz” over the many trials and tribulations James and I had weathered since our junior year of college. I guess I was feeling more than a bit sorry for myself. James had once again latched on to something that worked for him (or seemed to) while I was still floundering over my life . . . and still floundering around the outskirts of the unspoken attraction we had had for each other for the past decade. And I guess, if truth be told, I was just a little bit on the other side of horny (OK, more than a little bit) and this mixed with my recent spying of James’s cute ass, his cockiness and my frustrations.

An idea suddenly flushed to the front of my brain. It was so pinpoint perfect I sat in my driveway, the car still running, for a good twenty minutes while I plotted. I realized that I could possibly ease the pressure of frustration over James’s current western ways, cool the heat I was even then feeling between my long thighs and maybe actually want him to play cowboy. It was all a dastardly swirl in my mind, which fueled me to masturbate that night and fall into fitful dreams of revenge on poor sweet James.

“Yeah, come by around eight,” I said to James on the phone the next afternoon. “I’ll make us something to eat before we go to the club.”

Continuing our weekend partying, I knew I had the perfect excuse to get James at my house early. Although I had never treated a man the way I was planning on treating James, the plan I had hatched had me as sexually titillated as I had ever been. I had bought my new “outfit” that very morning, then driven halfway across town to shop in that store in the mall I had never dared walk into before (let alone buy anything in!). I knew not where these sinful ideas were coming from, but come they did and I let the imagined scenario wash over me from my fevered dreams of the night before to me assuring the tongue-pierced salesgirl that I would indeed be back for more toys. I was a woman alive with a singular purpose, albeit a sinister one, and I was tingling – and wet – with the idea that my friend James would soon be getting a painful comeuppance and I was the woman who would deliver it to him. Even rolling the word “comeuppance” around in my mouth made me so charged I stole a few strums across my zipper.

I had busied myself the entire rest of the day with house chores, between more stolen moments of masturbation; I simply hadn’t been able to keep my hands off myself when I passed the new clothes or toys I had bought earlier. Just the simple idea that James had no idea that I was setting an ambush for him made me feel so in control, so dominant, so alive. Every nerve in my body tingled more then it ever had in my thirty-five years.

When I heard the knock at my door at eight, I nearly swooned. I knew how James would be dressed, but I gulped at the idea that when I opened my door and James set his baby blues on me, he would be bowled over by how I was.

“Wow,” was all he could manage when I opened my front door.

I faced my best friend wearing tight black shorts; my heavy bosom pushed up in a buttoned-up leather vest; one-inch heel cowboy boots; and a hat, under which I had gathered my long brown mane. James stepped into my house and just drank me in from head to toe.

“Think you can handle it, cowboy?” I asked, slowly turning to afford James a full long view. I knew my ass looked ridiculously eatable in these tight shorts.

“I can handle anything you throw at me,” he declared, his recently added drawl even more pronounced.

I spied the black riding crop that lay on my couch just a few feet from us.

James and I had been out plenty of times with me dressing hot, so he probably thought I had simply dressed in character to what he’d be wearing. Maybe, he reasoned, I had finally come round to his ways, maybe he even coddled the hope that something might just happen between us, as if I had finally come to my senses and wanted to jump him with my hat on and spurs a-janglin’!

“Judy,” James said, grabbing my shoulders and spinning me to him. For the first time ever we stood so close.

I looked down under the brim of my hat. James was indeed ready; his tight jeans couldn’t lie.

“You want to do this, really?” my best friend whispered as I smiled into his broad chest. “After all this time?”

Breaking from James, hard as that was to do with the heat rising between us, I spun and began to step across the wooden floor.

“I mean you’ve looked hot before, but . . .”

“Yeah, I know . . .” I said, finally reaching my couch. I reached for the crop, with my back to him. I was counting on James being transfixed by the sight of my little ass, the impossibility of this moment. “. . . I now fit your little fantasy.”

“Sure do, cowgirl,” James said as I lifted the crop, inhaled and steeled my nerve. Buying and planning are one thing . . .

“Well,” I said to my couch, as I stood fondling the crop’s black long line, “why doesn’t my little cowboy show me his nice big saddle-horn?”

Cliché of clichés, I knew, as the challenge left my mouth, still I heard James inhale sharply and after maybe five seconds I heard the zipper of his jeans snake its way open; then the flump-flump of his boots hitting my carpet, the shunk of jeans falling. Relying on James’s ego, I had hoped it would take no time for me to get him out of his pants.

“Anytime you’re ready,” he announced and I turned with crop in hand.

I walked across the floor, tapping the crop’s looped head down against my boot. Completely naked now, James stood with his thick erection at a growing half-mast, a wide smile crossing his angular features. I was torn between wanting to jump him – his lean body did look that good – and keeping to my plan. Inhaling slightly, trying to maintain my composure facing this naked man I had always dreamed about seeing naked, I walked up to the guy and said: “You said you can handle anything I throw at ya . . .”

James’s smile faded just a bit (but not his thick erection) as I came to stand but a few inches from him to add, “Well, tonight, cowboy, you are gonna get it all thrown at ya.”

It would have been nice to know at that moment who it was using me for a ventriloquist’s dummy.

“Hop to,” I said. I lifted my arm, reached round and swat James to the outside of his right thigh.

“Hey, Ju . . .” James tried but I swat again, this time across to the outside of his left thigh.

“Get your ass across my couch,” I ordered, reaching back and all the way around my shocked friend. I managed a loud fast smack to the side of James’s bared right cheek.

“Judy, stop a sec,” James protested, his thick lips still spread in a slight grin. “I don’t . . .”

“I thought you were a real cowboy,” I said, dangling the crop off my hip. “I mean if you can’t take it . . .”

“I can take a little spanking from you! I am just surprised is awll.”

Goddamn, there was that drawn-out “awll”, that self-assured cowboy cockiness.

“Kneel across the couch,” I growled, determined to wipe that smile off his face, the drawl from his throat and add some color to his muscular ass.

James knelt and then lay across the front of my low blue couch, managing a quick smirk over his shoulder. I saw his baby blues register surprise though as I closed the distance between us – careful to make sure my boot heels click a’clicked on my wooden floor – then reached back with the crop and connected for the first time.

Szip-whap.

“Ah, mmm,” James moaned, pushing his crotch to the front of my couch as the lightest rectangular welt appeared dead center of his right cheek.

“Too hard for you cowboy?” I asked and reached back again.

I swat James, cheek to cheek, ten times total. Back and forth I gained rhythm (and confidence) as James raised his ass up higher and higher to meet my smacks, as if he were willing the beating, coaxing me to hit harder (which I did). The swats resounded off my pretty beige walls as fat red marks began to form across his beautiful flanks. At no time did my friend make any sound beyond inhaling sharply and at my fifth swat James managed a peek over his shoulder and, as usual, he wore that petulant smirk I had come to know so well. This had never been about hurting him, really, but I had to make the swats hard enough to make sense, to deliver the promise, to make my point known.

“Stay there,” I said, then turned and walked over to my pocketbook near the front door. Reaching inside I found the nondescript black bag and turned back to toss it on the couch to the side of where James lay his head.

“Open it up,” I said, coming back to stand behind the man.

“I think every cowboy should know what it feels like to be a horse,” I added as James spilled the contents of the package on my soft couch cushions. He faced a red butt plug with black “tail” attached and a little tube of something I had never seen (but made me wet the second I saw it): Anal Ease.

“Judy . . .” my best friend started, turning to me then, sitting on the floor.

James had such a little-boy look on his face, such a “why-me-I-haven’t-been-so-bad” cast to his strong chin and high cheekbones. But then I happened to catch sight of that damn black Stetson laying on my carpet, just a few feet from me, and I was assured that what was about to happen, had to happen!

It was all I could do to stand over him, to not squat down and take his cock in my hand, throw off my hat in a classic hair-a-tumbling-down-to-reveal-the-woman-underneath style, not dry hump him right there! James had no way of knowing that I really didn’t expect him to insert the tail (well, not then anyway), that this was all part of my plan to teeter his suppositions about me and therefore maybe knock his cowboy-ness back a few rungs down the ladder. The next few seconds would be telling. If I could get him to submit and ready himself for the tail, then I’d turn the tables finally, try to stop this quivering in my belly and dry the flood between my legs and maybe make us both dinner for real. I wanted to engage his mind more than his body and I hoped the potential of the plug could be enough.

“Just a suburban accountant with delusions of grandeur,” I announced, cocking my hip, staring down at him harder. I raised the crop to my mouth, the long knotted shaft of the thing pressing against my tight vest and heaving breasts. Another few moments I would have taken to masturbating yet again with the thing.

I kissed its looped end then added, “I guess you’re not really all that tough a cowboy, huh?”

“Give me this fucking thing!” James growled, reaching for the butt plug and lubricant. His big eyes were blazing but I smiled with him and, even standing over him as I was, I could feel the heat rising off his thick thighs, his cock now popping on its own in his lap. This might have been all new to him, but James seemed to be enjoying my control, my demanding . . . almost as much as I was.

He stood then and turned and I faced thin, welted rectangles crossing dead center of his tight ass. I could see him struggling with the tube in one hand, the tail in the other. I waited the requisite seconds, knowing that he knew I knew that he was readying himself to obey.

When James began to squat I knew we had both had enough.

“Just wanted to see if you’d do it,” I admitted, then I came from around the side of my best friend and took the plug and Anal Ease from his hands. James stood up fully then and faced me.

“Dinner?” I asked and my friend looked up at me, smiling.

James knew there was nothing more needing to be said. I had gained a foothold, broken him a bit, showed him how ready he was to obey me and in turn revealed so much about me, him and his view on the world.

Maybe this really was the cowboy way.