Cowboy Caper

Hey… I wanna become a cowboy stripper but I’m not sure what to wear, what to say, or even how to act. I know it sounds strange but it’s my passion.

Story Request by Anonymous
Source: Unknown

You know, kid, that’s the kind of wishful thinking that should really not be done so carelessly. Show some situational awareness. You’re in a gay bar. The kind of place that the Pink Fairy likes to lurk at when he has nothing better to do.

I can’t say I know him very well, but let me tell you, that particular mystical twink has a habit of turning people into caricatures of what they wanted to be. Not that those guys ever complain about what they’ve become. It’s not like they know better by the time that the Pink Fairy is done with them…

Oh, nothing. The last thing I said doesn’t really matter anymore. Chances are, by now he’s jerked that pretty little wand of his, moaned out an incantation, and sprayed you in the face with his glitter.

Well, I don’t know if that’s actually happened. But I think the Pink Fairy’s the kind of guy who would do that.

Now of course, the guys that the Pink Fairy plays with have to enjoy their transformation. Don’t be too concerned if you don’t notice anything happening right now. Believe me when I tell you that you’re well on your way, boy.

I imagine you must be feeling a little bit disappointed right now. But just look inside yourself. I guarantee you’ll feel something there. It’s like a warm, fuzzy ball of excitement. You can feel it? Yeah. Just as I thought. You’re in luck, boy. The Pink Fairy has heard you.

Don’t be surprised if you don’t turn out exactly as you wanted. Wishes and ambiguity and all that stuff. But you know what? What does it matter? It’s not like you’ll know enough to regret the wish that you made tonight when you’re done.


The bartender was right. You noticed nothing even after lying in bed for a few hours. But it is on the way to work that you find yourself going out of your way to compulsively buy a ten-gallon hat.

Despite having been a bit of a shy guy for much of your adult life, you give the guy at the counter a wink before you even realize you’re doing it. And before you leave, you make sure to put a little swish in your step, letting him get a good look at your flat little booty.

And then, like you hadn’t just done something completely out of character, you went to work and continued your day as normal.

The next day passed with a pretty similar set of events. Only this time, you bought boots. The kind that you always saw in those wild wild west movies, with the spurs and all.

The day after that you buy a leather vest. Then, a denim jacket. After that you throw out all your stupid pants and replace them with jeans. After that, the shirts go, replaced with plaid flannel button-up shirts. Long sleeves. Short sleeves. Every conceivable type and combination.

Going to bed wearing cowboy booys, jeans, and a leather vest, with your cowboy hat pulled over your head, is something that you’ve made a bit of a habit of.

Every night you lay in bed for ten minutes, palming yourself through your jeans, your cock rock hard in your jock strap now that you refuse to wear any other kind of underwear. You’re aware of the transformation now, and are powerless to stop it. Not that you want to stop it. If anything, you want it to get faster.

It isn’t long before you start jerking off in bed, as well. You’ve always been a quiet jerker, but over the last couple of days, you’ve started groaning and grunting like a true red-blooded American man while pulling your pole.

As the days pass, though, just lying on the bed stops helping the horniness, the arousal in the pit of your stomach. It just wasn’t good enough anymore. And it probably has something to do with the way that your mind has been changing with your body.

The last few days has really put some meat on your back side. It’s almost like your body is being built for riding. The only way that you can really get off is when you’re on your knees, legs spread wide, bouncing your still disappointingly-flat ass up and down like you’re straddling a cock.

And it doesn’t even work if you’re not holding on to your cowboy hat with your left hand and pulling your meat stick with your right. It’s a bit of a hassle, really, but boy do you spray a lot of jizz when you imagine that you’re riding a handsome young man’s cock.

And every night, without fail, when you finally collapse on the bed, exhausted from riding imaginary dick, you rest your head on a cum-soaked pillow and fall asleep licking your cum from the pillowcase.

Assless chaps are your next major purchase. And you replace your cotton jock straps with leather ones. You go in to work and someone asks you if you’ve suddenly gone Southern on them, and you notice that you’ve developed a Southern drawl over the last few days.

You blush, embarrassed for a split second as your old self is reasserted, but you quickly feel the heat bloom in your chest and in your groin. This is exactly what you wanted. You’re so excited that you can hardly contain yourself. You practically knock your coworker down in the race to the restroom to beat one out.

In the employee bathroom, you are just as vocal as when you jerk off at home. When you come back out, your coworkers are looking at you strangely. Some are snickering, others outright laughing.

It’s obvious what you’ve done. The neighbors probably heard you. And there’s someone gracious enough to point out that there’s a smear of cum at the corner of your lip. Instead of feeling humiliated, though, you just grin. You love the fact that they knew what was going on, that they heard you, that they all probably had the image of you jerking off in their heads.

One of your hotter coworkers comes by your cubicle when everything has settled down. He feels you up. Tells you that if you wanted to get your rocks off, you should have just told him and he would have taken care of you.

You sit there, feeling all hot and flustered. You tell him that you’ll think about him next time. When he leaves you realize that you can’t focus on any work at all. Not today. You’re too horny. You don’t even bother giving yourself privacy and just start looking at cowboy porn while palming yourself through your jock.

Waking up the next day, you notice that something is different. You don’t know what until you look in the mirror and see that your face isn’t quite as you remember it. The difference is subtle, but it’s there. You seem more symmetrical. More angular. More masculine.

Your body has changed, too. You’ve been losing fat over the last few weeks, but today you look cut. Your stomach seems a lot more defined. And your ass, which you have always lamented, is looking a bit fatter and rounder today.

At work, you continue to be unable to concentrate. You start beating off in your cubicle to gay porn. You don’t bother being private or being quiet about it. You realize that you feel no shyness and instead want your coworkers to know what you’re doing.

You moan and you grunt, hearing the whispers and the snickering. In between orgasms, you make a genuine effort to try and think about work stuff, but the thoughts just slip through your fingers. Math is hard. Words are even harder. You just find that you don’t care that you can’t think as good as you used to.

The important thing is that you think you hear a stifled moan somewhere in your coworkers’ whispered conversations. It feels good to know that you have an appreciative audience.

The next day, you look even hotter. Your jaw is taking on a masculine defition, the look you’ve always wanted. You’re growing stubble, not enough to make it look messy, but just enough to make you look a little bit rough and tumble.

You nearly cream your pants just looking at yourself. And speaking of your cock, which has always been a point of soreness for you, defintiely looks bigger in your jock. Not by much, but definitely bigger. Although, it’s not like you’ll ever be using it to fuck. You’re just not interested in that.

Coming into work, you realize just how much your attitude has changed, too. You used to be so high-strung, so stressed-out, occupied with being a productive worker and keeping your job. Now that you’re a lot more chill and just go with the flow, you realize how much you’ve been missing.

You can’t really bring yourself to care about all the stuff piling up at your station. All you care about is giving your coworkers their daily show every time you pull it out and start beating your meat at your station.

Day by day the changes progress. But always subtle. Not all that noticeable one day to the next. It isn’t until you look at a picture of your old self that you realize just how far along you’ve come.

Your body is cut. Your muscles are to die for. You have a cock that barely fits in your leather jocks. You are a specimen of masculinity, and your ass is a beautiful bubble that is definitely meant for riding with.

You love watching it bounce up and down on the dildo that you bought a few days ago for riding. It jiggles in such a pleasing way, framed by the straps of your jock. You love the way that the ripples travel over your flesh when you pull on one of the straps and let it snap back down on your skin to make your ass jiggle.

You get fired. But it’s no big deal. You haven’t done any work in weeks, anyway. And it’s not like you can comprehend the work that you need to do, anyhow.

The hottie coworker that’s been helping you empty your balls at work finally comes over to your house. You don’t know what comes over you, but you put on your full cowboy attire, boots, hat, and all, when he does.

You get him on the couch and put on some sexy music with a deep bass beat. Even though you’ve never danced before, much less erotically, this comes naturally to you as you shake your ass in his face and slowly shimmy off your denim jacket.

You pull open your leather vest and reveal your cut abs, rolling your torso to make them ripple. You strip off your pants and let him touch your strong, bulging thighs.

He reaches for your huge package as it dangles in front of him, and you grab the back of his head to grind your cock into his face. He grabs your ass and fondles you when you sit on his lap and work your booty.

You’re so fucking horny by the time that he grabs you, still in your jock, boots, and hat, and slams you against the wall that you’re practically begging for it. He manhandles you and you love it.

He takes you out into the balcony and he tells you that he wants the world to see you like this, he wants the neighbors to hear how much of a slut you are.

He bends you over the railing, the hat mysteriously defying gravity by staying on your head. He slides his cock into your muscle cunt and slaps your ass as he pounds into you, making it jiggle around his thick cock.

You’re in ecstasy. You love this so much you start drooling over the railing, unable to think, unable to move, powerless against his cock. It’s like he’s pounding right into your head, turning your brain to mush.

And when he’s done, you cum. Harder than you’ve ever cum before, spraying white-hot jizz through the gaps in the railing and onto the street below. Being so exposed makes you so hot. After all, you’ve got a gorgeous body now that just needs to be shown off.

But your night is far from done. He drags you back into the living room and tells you that it’s time for you to do what you were born to do. He tells you that you’re going to ride him. And you do. You ride him like a cowboy until your muscle ass is filled to the brim with cum, and your legs give out underneath you.

The next time that you show up in that bare where the Pink Fairy cast his spell on you, you’re no longer the lanky young man staring longingly at the dancers on the stage, in their cowboy outfits, and their impossibly gorgeous manly bodies.

No, this time you’re up on stage leading them, shaking your ass in front of a silver fox who’s more than happy to slip a few ones into your jockstrap and a few fingers into your hole, still loose and leaking from your earlier clients.

You can’t resist leaning in and whispering to him, "Hey, daddy, want a ride?"

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