Cowboy #2 – Two Stories


I have this List that I am working on for W.  At his request I’ve created an Excel spreadsheet listing all of the boys and men I have fucked in my life.  It is supposed to be in chronological order, and by name, with at least one fact about each one listed.  It’s slow going, as a) I don’t recall them all in order; b) I don’t recall all their names; c) I don’t recall them all, period; and d) as with every other project I am supposed to work on, I procrastinate until I am threatened with loss of life or limb.  Or some other punishment.  And since W doesn’t play with a punishment (or “funishment”) dynamic, there really is very little to compel me to actually complete it.
(Oh shit, wait, I’m supposed to be a good submissive, right? And a good submissive does things just to please her Top…you know, because she knows it will make him happy.  Uh-huh.  Riiight.  That’s me all over.
Well…maybe I am, a little bit.  So okay, I admit, I do work on it a little bit at a time.  And preen and glow when I do and it makes him happy or turns him on.  Cuz yeah, I am a bit submissive. ~rolling my eyes and sighing~)
Anyway, I’ve already written one story at W’s behest about someone from the list.  And now I am writing another.
The fun part of this one is that it’s masturbation material. For me, not you.  Or maybe you too–I have no idea what you do with my scribblings once I send them out into the wide blogging world. I’d like to think about you all hot and bothered, reading my stories with one hand down your pants–
Anyway.  So the other day, as I lay on the floor with my cunt rings tied open–
What?  I didn’t mention that in my previous post? Oops, bad blogger.  That’s what precipitated all the fucking I mentioned in that post.  Although we ended up on his couch downstairs, it all started upstairs, when he decided to tie open my “cuntflaps” (as he called them) by my rings obscenely, and then use other nasty implements to spread open my mouth and nose (nosehooks are for THE BIRDS!) and finally used clothespins on my outer labia to “pin” me to the floor.  After which he pulled me down on top of him, and, with my rings still tied open to my thighs, told me to fuck him.
It’s at moments like those that his claim that he’s not sadistic is clearly proved false. Know what happens when a girl’s insides–the parts that aren’t supposed to be exposed to the air–are? You guessed it–they dry out.
“Do it,” he said, when I whimpered and tried to pull away.  “Go on.  Hurt yourself.”
So I did.  (Because, you know, I’m a good submissive, remember?)
I pushed him inside my dry, tender, exposed hole, whimpering and whining the whole time.
And fuck me if I didn’t get wet.
Soon I was whimpering and whining because, in spite of my head telling me I shouldn’t be, I was excited.
~ sigh~ I am just so fucking easy.
But this post isn’t about all that.  This post is about what he said to me as I impaled myself on him, feeling my rings pulling me open wider, and getting hotter as I thought about being so utterly exposed, so unprotected, my hole spread wide…
Grabbing me by the hair he pulled my face close to his lips. “Tonight, when you’re touching yourself,” he said, “I want you to think of the next guy on your list.  And when you do, I want you to imagine what it would have been like if you’d been made to fuck him with your rings tied open just like this.”
And I did. Later that night, lying in bed next to Ad, who’d fallen asleep early, I touched myself and imagined what it would have been like…
And because I have to tell the REAL story of the 25th guy on my list, you’ll get two stories in one!

#25 – Cowboy #2

(Yep, there were two of them. NO, not at the same time.  I hadn’t done that yet.)

The Real Story of Cowboy #2

Once upon a time I was living with my older (crazy) sister. I was trying to leave my first husband (trying being the operative word…I left him at least six or seven times before it stuck) and she offered me a place to stay while I got myself situated.  Shortly after I moved in, she decided to leave her husband, and moved to a small, central California town, taking me with her.
Things were not so great living with my sister.  (Note the “crazy” modifier above.) Late one night, after a particularly stressful day with her, I ended up meeting the husband of a friend of hers out at the local honky-tonk. And yes, I can call it a honky-tonk, because it was, and no, he wasn’t Cowboy #2.  He was just a friend that knew how rough it was living with my sister, so he invited me out for a beer to get me out of the house.
Stupid me, I went.  Stupid because I ended up sleeping with one of my sister’s friend’s husband’s friends, “Cowboy #2” of this tale, and that, eventually, ended up being part of the reason I ended up not living with my sister shortly thereafter. Or being friends with my sister’s friend or her husband anymore. See, I was smart enough not to sleep with F (my sis’s friend’s husband), but I wasn’t smart enough not to sleep with C2, who was also married.  And later, when it came out that I had done that, well, it wasn’t hard doing for my sister to convince her friend that I had also slept with F.  (Why would someone accuse her own sister of something like that, especially when it’s untrue? Um, were you paying attention when I used the word “crazy” up there?)
Anyway, that’s another story, and not one for this space.  The story I can tell here is a typical one: F and I had a couple beers, he introduced me to some of his friends, we had a few more beers and they all kinda flirted with me in that way that men do with any girl between the ages of 22 and 50 after they’ve had a few beers. The bar was a typical small town bar, smoky and dark, with honky-tonk on the jukebox, a couple pool tables in the middle and everyone drinking Coors (it was California, after all.)  C2 was no more or less interesting than any of the others, but he stayed later, and flirted a little harder, brushing against me as we played pool, smiling a lazy cowboy smile, and…hell, offered me a ride home when I was ready to go (F was still drinking hard.)
So I fucked him in his truck, straddling him with the steering wheel pushing against my back, at a roadside rest area about 10 miles outside of town.
I don’t recall much about it, to be honest, and can’t remember his name or his face. I do remember his truck had a saddle and a coil of rope in the back. And he wore a cowboy hat. (See how clever I am? “Cowboy” #2.)
Not a very exciting story, right?  How about we sex it up?

The Story of Cowboy #2 – As It Should Have Happened

Unfortunately you don’t get a lot of background in this story, as you did in the first. When I masturbate, I get down and dirty pretty quick, instructions to make up a story or not.  All I see is myself back in that bar, with those men around me.  Three or four of them in their shitkickers and cowboy hats, drinking beer, laughing, eyeing me.  I’m in one of my short short denim skirts this time, a tank top and a pair of outrageously high heels. The kind I never would have worn back then.

And underneath my skirt, my rings are tied open by black silk cords that wrap around my thighs.

As I lean over the pool table (ostensibly to line up my shot, but we all know I can’t play worth squat) those strings are made visible.  I feel the Cowboy come up behind me and lean into me.  I can feel the scratch of his jeans against my thighs, his wool shirt against my back, a boot on the inside of one of my feet.  He holds my leg there, keeping them open without anyone really knowing what he’s doing except me.  I feel a hand on the inside of my thigh, and then, higher. I feel his fingers, rough and callused, brush against my spread cuntlips–

–and stop. I can feel his confusion as he pauses for a long moment, neither of us breathing.

And then his voice, in my ear, “Keep up what you’re doing,” he says. “Act like nothing’s going on.” I feel him square himself behind me (hiding what he’s doing from the others?) even as he edges my legs farther apart. As I pull the pool cue back to take a shot, I feel his fingers probing that open hole, tentatively at first, exploring just the edges of this bizarre configuration that W has put me into, and then more roughly.  His fingers are hard and thick, and in a moment he has shoved one into me.

I feel his cock grow hard in his jeans against the backs of my thighs.

“You fucking little whore,” he says, grinding against me.

And this is where total fantasy takes over and the story loses all sense of reality or focus.  Touching myself, the story becomes jumbled in my head with a story I read once long ago, in fact one of the first pieces of hardcore porn I ever read, in a Hustler magazine I found in my dad’s apartment.  Suddenly the Cowboy is fucking me over the pool table, still fully clothed, with the others looking on. Then they are taking turns, and then, at some point, they are fucking me with the pool cue as well.  This is a recurring fantasy derived from the original story that I read, but now, at W’s behest, it is enhanced by the added humiliation of having my rings and cuntlips tied open.

Lovely.  Nasty and sick and so fucking hot I come in about three minutes.

And that’s the story of Cowboy #2, both real and imagined.  I think we’d both have had a better time if W had been around back then.

2 thoughts on “Cowboy #2 – Two Stories

  1. Hi Jade:
    I just love reading your blog…it’s so fascinating. Look forward to a new installment every day and disappointed when there isn’t
    Keep up the erotic work.

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