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Little Sir

I’m at the Prairie.  It has become my stomping grounds of choice for the summer.  Less hassles, less trolls, and, yes, less traffic – as in, fewer dudes to chase about.  But that’s a good thing.  This year, I am not all about the numbers; I’m all about quality. 

Settling into my usual spot in the middle of the prairie, situated on a slight, eastern-facing slope, I am confident that my ass is clean and ready should the opportunity present itself.  It hasn’t.  Not so far this year.  I’ve sucked off a number of dudes, but many days all I get for my time at the prairie is a bit of sun.  I’m okay with that.  I have been rather picky this year.  If there is something about someone that puts up a red flag, I retreat to my blanket and pat myself on the back for actually having standards (for a change). 

A number of the regulars have returned, though a number have also vanished.  Everyone comments about how ‘quiet’ the prairie has become.  Last year, I did not visit at all, and everybody tells me that last year’s traffic was almost non-existent.  There are some new arrivals – in some later post, I promise to give you the lowdown on the new cast of regulars.  Suffice to say, there are more I am unwilling to play with, than play with. 

On this particular day, as I am walking toward the prairie, I console myself, telling myself that there really is no longer any need for me to douche before coming to the prairie, since it appears no one comes to the prairie to fuck anymore.  Still, my ass is ready – it’s the former-Boy Scout in me.  Plus… you never know.

It’s a partly cloudy day.  We’ve had so many of those this year.  Too many storms, too many grey days.  It hasn’t felt like much of a summer at all.  But I’m content and grateful for even a few rays.  As nice as it is, I am amazed that no one else is around.  I’d already been there for a half hour and not seen a soul.  That’s become rather typical this year as well.  Not that I don’t enjoy having the place to myself.

Stripping off my long black shorts, I decide to put on my Pistol Pete jock and a cock ring.   I get the cock ring on and look up.  There, on the far northwestern corner of the prairie is a pale, shirtless dude.  He looks exceedingly young and I assume he is on his way down to the lake to meet some friends.  He moves along the northern side and his movements remind me of the time this black dude showed up out of the blue, in response to an ad I had placed on Craigslist.  He never bothered emailing me, he knew where to find me.  He showed up, walked in, and fucked me royally.  There’s a post on here somewhere about it.  It was the highlight of that summer.

But back to the present…

The grass is high enough where, while I am fairly certain he can see the top of my head, he can’t really get a good look at my body – at least not enough to know I’m naked.  So, I toy with the idea of getting on all fours and turning my ass his direction.  I’m not even sure he’s taken notice of me at all.  Nixing that, I get on my knees and pull on my Pistol Pete.  Looking over my shoulder I check to see if this has gotten any reaction.  Well, none that I can tell. 

He reaches that point where the path he’s on diverges in two directions – one that leads to the lake, the other to the woods to the west of the prairie.  Based on his confident stride and trim form, I am hoping he’s headed my direction.  But to find out, I would have to stand up a bit and peek over the grass, which means getting dressed.  As I weigh my options, I lube up my hole.  Look?  Don’t look?  I decide I definitely want to know.  I’m about to slip on my long shorts, when I hear a voice that says, “You don’t have to bother with that.  I’m okay with it.”

He’s a speedy little fellow. How little?  Well…

He’s about five feet tall, with a tiny waist, smooth pale skin, pink-berry nipples, and not an ounce of fat on him.  He’s wearing a pair of cutting edge frames and his bleached hair is cut military style.  His army-green pants fit him perfectly – snug at the waist and hips with the legs relaxed and full.  I start to drool when I see his black army boots.  

He is young, but not too young.  Actually, due to his height, slight build, boyish face, and perfectly smooth skin, I bet he’s mistaken for a lot younger than he actually is, which, I am going to guess and say 26 years old.  But, trust me, this boyish man does not answer to ‘boy’… ever.

He’s looking down on me, his arms crossed his chest.  It’s then that I notice something that is typically a deal breaker for me: he’s smoking a big fat cigar!

I don't like cigars.  They nauseate me.  Hell, I can barely tolerate cigarettes.  Consequently, if someone lights up in front of me, or wears the telltale signs of nicotine use, it's a no-go.  I don't like the taste.  I don't like the smell.  I don't like the mess.  Now, this is coming from someone who smoked for ten years; someone who wanted desperately to quit from the day he started.  But that was a long time ago and as part of my newly found standards, smokers are, more or less on my no-fly list.  But, yes... I will make exceptions.

But something about this kid ignites something in me.  That, plus the fact that we are in the great outdoors and there is a slight breeze tells me that I probably won’t lose my lunch if he should continue to chaw on that cigar.  He asks me what I’m up to.  I begin calling him “Sir” right out of the box.  He then inquires whether there have been a lot of people around.  I explain that it’s been absolutely dead, and that he’s the first person I’ve seen.

“So, what would you like to do, boy?”

I melt.  “Anything you’d like, Sir.”  I’m staring at the toe of his boots as I say this.  The idea of being dommed by such a tiny little fucker totally appeals to perv in me.

He unzips his pants and spreads open the zipper, revealing a matching army green jock with a nice bulge to it.  My mouth is on it without waiting, without asking.  “Good boy,” he says, as he blows out a fume of cigar smoke.

“Anything, for you, Sir.  Anything”

I don’t work very long on that pouch.  We’re out in the middle of an open prairie, and even though the grass is tall enough to conceal part of me, I’m pretty sure anybody that happens on us would plainly see a half-naked dude with a ball cap with his face buried in the crotch of a cigar-smoking little dude.

I suggest that we go to the woods, for more privacy, and he agrees.  I ask what I should bring with me.  “Whatever you think you’ll need.”

“Do you want to fuck my ass, Sir?”

Yeah, I decide to put it right out there.  Then there will be no unmet expectations.

“If that’s what you want, pig.  You got a condom?  Your hole clean?”  I answer affirmatively to both and he asks, “Is there anything else you want, boy?”

“Just to be of service to you, Sir”.  Again, I stare at his boots.  “And… maybe, if you like, Sir, you could press your boot on my dick.”

He smirks at the suggestion and blows another plume of smoke in the air before walking down the path, toward the west.  I grab my stuff – lube, condom, poppers, shove on my shorts, and quickly follow.  Dude looks as good going as coming.  Tiny fucking waist, and those pants – hot.  I appreciate his swagger and can’t wait to be of service.  I would also love a peek at his ass – bet it’s damn cute.

Once in the woods he asks me if we should go in further.  I tell him I think that would be a good idea. Turns out he’s never been to the prairie before, so I take over and lead the way to a small indent off the main secondary trail.  It’s the same spot where the black dude that answered my Craigslist ad fucked me two years ago.

I swiftly kneel before him, woods to my back, and waste no time unzipping that fly.  I want more of that jock.  He unbuckles his belt and I heft his pants down, revealing that jock in all its glory.  My mouth is on it in a matter of seconds, like a thirsty fool in need of sustenance.  He smells great – clean.  My hands work their way back to his ass.  It feels super fine. 

Little Sir moves that pouch aside and out plops a pair of major balls in a sack the size of a tennis ball.  Again, my mouth knows where it’s needed.  As I lick his balls, my hand moves up to his nips. “Yeah, you don’t have to take it easy on those.”  So, I don’t and am rewarded with the shaft of his cock trying to make an escape.  Eventually it succeeds. It’s nice.  Beautiful to look at.  Seven inches and nicely, nicely thick.  My hole tingles in anticipation.  It’s in for a bit of a stretching.

See, it’s been three weeks since I last got fucked.  Yes, I missed it.  Yes, I had opportunities aplenty.  But nothing ever seemed right.  This?  This is so right; it has my whole body atwitter.

I take that bad boy deep in my mouth, all the way to the root, and am rewarded with a satisfied sound issuing from Little Sir’s mouth, which still has that stogie clenched in it.  I flex my throat a few times and then pull off, running my tongue all round that magnificent helmet head.  Pulling all the way off, I leave my tongue sticking out as a pillow for the head of his dick to rest on.  Little Sir removes the cigar from his mouth and spits on his dick.  My tongue rolls up and toys with the spit a bit, never taking my eyes from his.  Now it’s his turn.  He starts fucking my mouth slowly, soon I’m matching him stroke for stroke, changing up the grip of my mouth, opening up the back of my throat. I know he’s having a good time. 

A good ten minutes passes by, during which I employ all my favorite tricks – the mouth waggle, paying attention to that main vein with my tongue, using suction, using my throat, using my hand, running the palm over the head of his saliva soaked dick. All the while, I’m squeezing his butt cheeks, licking his balls, working his nips.  Little Sir changes up his posture a few times, spits in my face, and on his dick, while continuing to chomp on that cigar.  Mercifully, he refrains from blowing it in my face.  “You taste that cigar on my dick, boy?”  I nod affirmatively, my mouth full, my dick, majorly boned.

He pulls his dick out of my mouth. “All right, pig, hand me that condom.  Go run and check on your gear.  Next time I see you, I want that ass in the air, begging for dick.”

He needn’t tell me twice.  I run back to my spot, shuck down my shorts and hall out my good lube – industrial grade – the kind my butt doc uses!  My hole is good to go and I am just about to return, when I look up to find Little Sir standing over me once more.  “You want me to fuck you out here, boy?”

I consider it, but again, the grass is not high enough and the day is just nice enough that someone may come along and see us.  I tell him I will run ahead and return to the same spot, ready to take his dick.  I take off, and make my way back.  This guy moves fast, so I have to move faster.  I drop my shorts and remove them.  I think my ass looks pretty good framed in my Pistol Pete, so I decide to leave it on.  I’m all lubed up, so I bend over.  As I wait, I grab the poppers and take a good strong hit, one in each nostril.  As I do so, I feel Little Sir’s covered dick press against my hole. “Oh, yeah,” he says, “look at you.  You are a pig, aren’t you, boy?  You want that dick bad.”  He takes his time and it feels amazing – like the world opening up before me. 

Soon, he’s working up steam, pounding my hole.  In a matter of minutes, I take over and begin fucking back on his dick.  Because he’s so short, I resist the urge to arch up.  I tighten and relax my hole, so he knows what he’s got to work with.  “You like that dick, pig?  You like being fucked by a real man?” 

“Yes, Sir.  Fuck yes, Sir!  Use me, Sir.”

Eventually, I decide to test the waters and begin to arch up a bit.  This puts me in an interesting position, for I am now able to fuck down on his dick, due to him being much shorter than me.  This hits me inside in such a way that it causes my body to tremble, in a good way.  It feels fucking hot.  Even though I know he already knows, I tell him as much, and he amps up the tempo and intensity.  We’re both working up quite the sweat.

Then he pulls out of me.  I turn around and get on my knees.  I want his load.  Peeling off the condom for him, I take his cock deep in my mouth once more.  It’s throbbing.  It’s ready.  I pull off.  Little Sir spits on his dick and I play with it with my tongue.  We end the way we began.  “Pull on those balls, boy.”  I do.  In their relaxed state his sack is the size of a tennis ball, but pull down on it and it grows quite lengthy while still retaining its girth.  I yank on them and take him to the point of pain and then release, over and over again, my mouth furiously working his dick for all it’s worth.  Suddenly, he grabs the back of my head and splashes the back of my throat with his seed.  He just holds my head there as I flex my throat around his cock in response to each spasm.  Good.  Clean. 

“Can I come, Sir?”

Permission is granted.  I keep his dick in my mouth as I stroke my meat.  I love the weight of this dude’s cock on my tongue.  He praises me for my efforts and is rewarded with a nice-sized load.  It flies all over the place.  Once satiated, I look down and to my horror I see that my cum has landed on his boots and pants leg.  I don’t wait to be told.  I lick off the cum on the toe of his boot and then suck it off the leg of his pants.  He pats my head and tells me what a good boy I am. 

And I am.

We relax.  I remain on my knees, cleaning him up with my tongue.  He’s in no hurry.  I thank him, watching as he reassembles himself.  Such a hot little fucker.  Then I stand, and realize just how much of a height difference there is between us.  It’s a little comical. 

No kisses.  No hugs.  I head back to my blanket and he walks off toward the lake.

It was perfect.

I rinse out my hole.  Gargle.  Use water and wet wipes and a nice white cotton towel to clean up with.   No one around.  Just me and the sky.  I mentally have to pinch myself.  Did that just happen?  Out of the blue.  Where did he come from?

I wonder if I will ever see him again.   If not, I’m fine with that.  Before we left each other’s company, I made a point of telling him when I am usually sunning myself on the prairie, but if he has no interest in second helpings, that’s cool by me.

I pat myself on the back for being so prepared, despite the odds of anything occurring and vow to always come to the prairie prepared. 

Because you never know when some hot little fucker in army green may show up out of nowhere.

Little Sir?  I salute you.


Ray's Cowboy said...

Love the story.. Is this true or what??


Upton King said...

Ray... I swear it is true. All the stories that I share about myself and my sex life are true. Over the years, I have really put myself out there. More recently? Not so much, hence the huge reduction in sex stories about myself. I'm glad you enjoyed the post. Love your blog! - Uptonking from Wonderland Burlesque

whkattk said...

I think the prairie sounds like an awful lot of .... fun! This post reminds me of my military days - of jacking off with a bunch of buddies out in the middle of the desert, or up on the roof of the barracks.

Koba said...

Umm... Yum! I used to smoke, too. Quit for over 10 years, but now I smoke when I'm on vacation. Stupid, I know, but I'm calling it my mid-life crisis. Happy trails and Happy Canada Day, my friend!