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Cock-Sucking Cowgirl
By Katy Terrega

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My cock strained at my jeans as Lissa’s tiny fingers fumbled with the zipper. Her blonde head – cowboy hat charmingly askew - bent studiously over her task until her small hand finally wrapped itself lightly around my now-exposed shaft. “It’s so big,” she whispered softly, looking up at me briefly, her eyes bright in the moonlight.

But then, with a quick smile, she once again bent to my thick shaft as her fingers explored the veins that ran from the base to the swollen tip. Her soft and tentative touch was far more exciting than the feel of a more experienced hand. My cock swelled at the soft whisper of her breath that feathered up and down the sensitive skin of my shaft as she explored my hardness with her eyes and her fingers.

The feel of her tongue tip, when it reached delicately out to taste the tip of my engorged cock was enough to make me groan. My response, coupled with a telling twitch of my excited organ elicited a giggle from Lissa. She’d already told me that she’d never given a blow job before, not even to the guy who’d popped her cherry, and it was obvious that she was enjoying her newfound power.

But not as much as I was, I thought dimly, as her smooth skinned fingertips continued to trace their way lightly up and down my shaft and her tongue now more boldly explored the mushroom shaped tip of my dick. She lapped at the sensitive slit and I heard her giggle again as she had her first taste of the pre-cum that had already begun to ooze out.

Her hands closed more determinedly now around my thickening shaft and I felt the wetness of her lips begin to wrap around the swollen head of my cock. It was a struggle not to plunge the full length of myself into her warm and willing mouth right then and there; the unintentional tease of her feather-light touch had me wanting more, and wanting it right now.

Instead, I let her continue on her slow and deliciously agonizing way, thanking the gods that be for putting this sweet little filly on her knees in front of me.

It wasn’t, after all, how I’d expected to spend the evening. As a volunteer chaperone for the annual East High Halloween Dance, I’d figured more on a titillating but rather boring night spent watching gorgeous young things parade around in skimpy little costumes. And I’d been right about that, there was plenty of jiggling, young flesh for me to surreptitiously admire. I was even getting more than my fair share of flirtatious attention from the little nymphets, dressed as I was in my best equivalent of the Marlboro man, complete with thigh-hugging chaps and tight cowboy boots.

But seeing as how I’m the resident swim coach at East High, and therefore only allowed to look, I’d had my fill of those ultimately unsatisfying cuties by about 11 o’clock. I was getting bored with my limited duties; tasting the punch to see if it was spiked and checking the bathrooms to make sure nobody had passed out.

But then I spotted Lissa. Not that I knew it was her at first, all I saw was a charmingly cute, little cowgirl. Dressed in a short, flouncy denim skirt, with a white cowboy hat and matching boots, she was easily the cutest girl at the dance. I watched, transfixed as she made her way toward the punch table. Captivated by the tiny little titties that bounced adorably under her red-checked halter top, I felt a surge in my already slightly swollen member that only increased as I saw her pointy little nipples poking through the bandana-like fabric.

A little frustrated at all this visual stimulation with no satisfaction in sight, I turned, intending to step out for a much needed breath of fresh air. But then I realized who this adorable little creature was. Turns out I’d seen her before, but she wasn’t my student; as I recalled she’d graduated just the year before. But that hadn’t stopped her from coming to pick up her sister, who was in my last hour swim class, and hanging around and flirting rather self-consciously with me while she waited for her sister to change.

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What I remembered most about her was her endearing way of flushing ever so slightly whenever she managed to make eye contact with me, which wasn’t often. And who could forget how her little bra-less titties barely pushed out the thin t-shirts she always wore to the pool? I’d had many a daydream about sucking on those fine-pointed nipples through that almost sheer cotton fabric.

And here she was, looking just as bored as I was, obviously in need of a big strong cowboy to fetch her a cool glass of punch.

In two strides I was behind her and reaching for two cups. “What’s a cute little filly like you doing in a dump like this?” I drawled in my best John Wayne voice, smiling at her as she turned. My arm lightly brushed her shoulder as I scooped up some punch and I felt goose bumps rising up on her arm. That made me think of her little goose-bumped sized titties but I tried to hide my lascivious thoughts with a warm smile.

I saw that sweet little flush begin at the tip of her nose and spread past the freckles and down on toward that barely-there little halter top. Looking rather embarrassed, she managed to stutter “Oh, I just got volunteered to chaperone.” Her hands indicated her costume, and she shrugged, “I didn’t want to dress up,” she said with a shy little smile, “but my mom made me.”

I just raised my eyebrows at her and said, “So did mine.”

She giggled then, her high voice belying her age, as she seemed to notice my costume for the first time. “Hey!” she said delightedly, “we match!”

“That we do,” I said, resting my arm rather comfortably around her hip while we sipped at our punch. “Only you,” I said with a wink, “look much better than I do.”

“D’ya really think so?” she asked, so earnestly that I ached for her. She dropped her eyes, “I thought I looked stupid.”

Trying hard not to laugh, and noticing that she hadn’t pulled away from my friendly touch, I decided to push my luck. “Honey,” I said, drawing out my fake cowboy accent, “you look sexy as all get-out.”

Her eyes widened for a minute and I thought maybe I’d gone too far, but then a delighted smile spread over her face, along with that oh-so-familiar flush of hers. It was then that I realized that this night might not be a complete bust after all.

Sometime later, after sweet Lissa had shyly admitted that she’d had a bit of a crush on me from the beginning, and after I’d let her know that the feeling was definitely mutual, well, it wasn’t long before we both decided to go out for that breath of fresh air. From there, it wasn’t very long till we found ourselves pressed up against the cool brick of the school, making out like two kids. And it wasn’t long before I realized that my initial misgivings about taking this little girl farther than she wanted to go were completely unfounded. This was one girl who, shy though she was, wasn’t afraid of asking for what she wanted.

Now, her mouth sliding it’s tortuous way down my cock, I was only too happy to give it to her. I groaned again as her lips slowly slid down to my balls. My response to her ministrations seemed to embolden her.

She began to bob her head slowly up and down, pulling my thick cock in and out of her wet mouth. Her small fingers wrapped themselves around my shaft every time her lips slid to the tip of my cock, and even though her movements were a little jerky and inexperienced, or maybe because of that, they were certainly having the desired effect.

“Yes,” I moaned as Lissa’s head bobbed faster. I grabbed a hold of her silky blond hair and her hat slid to the side as I guided her mouth even more firmly on my by now pumping shaft. Gamely she kept up, her small head pulling and tugging at my cock until I knew I couldn’t hold back anymore. With a groan I began shoving myself deeper into her mouth as I felt my swollen balls begin to contract and send my hot jiz deep into Lissa’s tiny mouth.

I was a little worried that she wouldn’t like this strange new sensation and thought maybe I should pull back, but it was too late. To my surprise and pleasure I felt her draw me in even deeper as I pumped her mouth full of cum. I let loose then, spewing my juices down her throat as she sucked at my still hard member. I groaned again as she continued, her little tongue licking and flicking at my still quivering cock. Pulling her to her feet, I turned her around so that her back was against the wall of the school.

“Did I do okay?” she asked, in all seriousness.

“Lissa, honey,” I mumbled into her hair, “you were fantastic.”

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She seemed to sigh in relief, then, and I kissed her, rather harder than I’d intended, but she returned my kiss with a ferocity that made me wonder if her first foray into cock-sucking had perhaps excited her a little more she knew. The way her lithe little body was pressing forward to grind against mine was also rather telling, I thought. And her breathless little moans as I explored her mouth with my tongue confirmed my suspicions that Lissa was feeling pretty darned hot. I thought it was as good a time as any to press my luck.

“Lissa,” I admitted, kissing my way delicately down her neck, “I’d sure like to make love to you.”

“Oh!” she squeaked, whether at my statement or the fact that I’d just taken a tiny bite-sized nipple into my mouth, I wasn’t sure. I still wasn’t sure after she gasped out “Oh....yes!” because at that point I’d sucked that tiny titty deep into my mouth. But as I reached one hand under her flirty little cowgirl skirt and let my fingers crawl across her soft thigh till I they reached the soft and very wet cotton of her panties, I was fairly sure what she meant by her gasping “Oh, yes.....like that.....yes...”

I was sure enough, anyway, to let my fingers gently explore the dampness that covered her little pussy. My fingertip found the protruding tip of her little clitty tip through the material and I rubbed gently on the little nub, eliciting yet another gasp of what sounded like surprised delight. I pressed harder on her most sensitive spot and brought my face back up to hers so that I could whisper in her ear. “Now it’s your turn, little missy,” I drawled, as my finger pressed harder on her sensitive little spot.

As I dropped to my knees in the cool grass in front of her, I heard her gasp again. Flipping her little skirt up around her waist and pressing my face into the dampness of her white cotton, I was rewarded with yet another surprised little squeal. I was pretty sure her pimply high school boyfriend had never done this for her and I decided right then and there that I was going to make Lissa’s first pussy licking a damn good one.

Delicately I pulled her drenched panties to the side and licked at her almost hairless mound. She sighed as my tongue trailed along the cleft between her pussy lips. I probed deeper down and found her to be wet and wide open; my tongue slid easily into the depths of her tight little cunt. I felt her quiver as I moved my tongue back up, stopping to rest on her exposed little clitty. I used my fingers to spread her lips open wide then and let my tongue flick her hardened little nub gently back and forth.

Lissa was squirming underneath me now, her barely curved hips straining to get closer to this new sensation. Her breath was coming in little gasps and I could barely hear her words. “Oh!...yes..........I like that........Oh!” I slid one finger gently into her hot little twat and could tell that, although she wasn’t a virgin, she still had the tight cunt of an inexperienced teenager. She began wiggling against me even more now, as I slid my finger in and out of her dripping box, all the while flicking at her little, virgin clit.

She gave a surprised squeal as she began to vibrate under my tongue and her hands clutched spasmodically at my hair when her body went suddenly rigid. “Oh yes....oh yes......oh yes!” she whispered over and over as my tongue flicked at her spasming little nubbin. Her satisfaction was more than obvious as her agile little body quivered with an earth shattering orgasm.

With one final gasp her shudders stopped and I looked up to see her looking at me, wide eyed and obviously surprised. With one finger still in her pussy I stood up to kiss her. “Did you like that, Lissa?” I whispered between nibbles on her lips.

“Oh, yes,” she said, in her high, girlish voice, “I didn’t know it could feel like that!” Her kisses grew a little more intense now as my tongue probed more deeply into her wet mouth, still tasting faintly of strawberry punch.

“Do you want it to feel even better?” I asked, pressing my engorged cock up under her skirt against her still exposed pussy.

Her answer was more than obvious as her delicate fingers reached for my swollen member, awkwardly trying to guide me toward her hot little twat.

“Here,” I said, stopping her for just a moment. “Let’s try it like this.” And I gently turned her around to face the wall. Bracing her hands on the cool brick, I pulled her hips back until she was bent invitingly as the waist, pert little bottom showing itself under the denim skirt. She wiggled it invitingly as I stroked her long flanks, running my hands up and down her thighs until she began pressing herself rather insistently against my body.

Not needing any further encouragement, I slid my thick dick between Lissa’s willing thighs. She was still wet from her own juices and my cock slithered deliciously between her legs, sliding in and out of the wet cave formed by the meeting of her flesh. I reached around to stroke her little titties while I let myself slip through the damp skin where her pussy encountered her thighs. She groaned as my fingers found her teeny little nipples and began rubbing them.

Pressing her hips back against mine, she writhed under my ministrations, obviously wanting more, until I finally let the tip of my cock slip past the tight opening of her hole. Then she stopped, moaning a little and I was afraid for a moment that I’d hurt her. Until she moaned again, and pushed herself backward, impaling herself suddenly and quite fully on my waiting cock. It was quite clear that little Lissa was ready for more.

With a smooth motion, I pulled my cock out of her dripping pussy and then shoved it back in to the hilt. Her tight little cunt sucked me deep inside of her, stroking me with smooth, wet walls. I felt her petite ass press deliciously up against my balls as I reached the end of my thrust, and I ground myself deep into her as her cheeks spread wide underneath me.

I reached around under the front of her skirt to diddle on her clit some more and found it hard and swollen again, poking it’s way out of the folds of her smooth lips. She gasped as my fingers flicked at the sensitive little tip while my cock stroked it’s way in and out of her tight little twat. In what seemed like two seconds Lissa was cumming again, this time crying out as her pussy contracted tightly around my pulsing organ.

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I continued to thrust into her incredibly tight hole as she shuddered under me, amazed at how firmly her pussy grasped my pumping cock. I held tight to the lean curve of her hip as my strokes increased, until my cock was pistoning hard against her pert little ass and my balls began to swell in anticipation.

With a groan I began to pump my jiz into her sweet hole. Her pussy seemed to be sucking the jiz right out of my straining cock and I pushed myself into her as deeply as possible as I squirted my jiz into her still contracting little tunnel. Pressing her fine ass against me, Lissa managed to milk me dry with her tight little hole until I’d emptied myself completely into her.

I kept myself deep inside of her as we leaned against the wall, our breathing slowly returning to normal.

“Oh, my...” Lissa said, with what sounded like a thoroughly satisfied sigh, a few moments later. “Is it always like that?”

Reluctantly I pulled slowly out of her and turned her around to face me, straightening her little skirt and smoothing out the thin fabric over her tits. “You mean that good?” I asked as I positioned her white hat on top of her pretty, blond head.

“Uh, huh,” she said, her fingers idly toying with my shirt button, her eyes looking expectantly into mine.

Swelling up my chest under her hand, I said, in my best cowboy voice, “Only with a real man like me, little missy.”

She giggled at my posturing and suddenly her face flushed hot. “I’d never done it, you know, those ways before,” she said hesitantly.

“You mean with your boots on?” I asked, and her delighted laughter filled the night air as we slowly headed back to the dance.

It wasn’t until after our chaperoning duties were over, however, that I got a chance to show Lissa that there were, indeed, several other ways of making love. Lots and lots of ways. Although I do have to say that buck naked - except for our boots - was definitely the most inspiring of them all.

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Cock-Sucking Cowgirl
Published by KT Enterprises
Copyright 2006 Katy Terrega – All Rights Reserved
No Portion Of This Story May Be Reprinted Without The Author’s Permission

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