Hailey's Slutty Spanking

Hailey's a pretty woman, too. She's 5'7" and thin at 129 pounds. She has short hair, a very dark brown, but dyed platinum-blond, that comes down just to the bottom of her jaw. Her eyes are blue, almost gray. And she has a fairly wide mouth with full, but light pink, lips. I know she has great curves and breasts, too, but with her almost-baggy blouse, there's no seeing that.

I drop onto my stool with my back to the desk, pulling Hailey down at my right. She's been here enough to know what I want her to do. She drops to her knees. Which has her facing me. I reach down to unbutton and unzip her jeans. "I don't know what slutty things you were up to, and I don't care. You know better than to be tardy with a delivery. Since GrubHub won't punish their delivery-sluts in the proper fashion, we customers have to do it ourselves! I should get a discount for this!"

With a hand to Hailey's shoulder, I pull her forward and lie her across my parted thighs. It does let me feel those pretty boobs of hers as they lie against my left thigh. Hailey lies still as I reach for the waistband of her jeans. I ease her jeans down leisurely to reveal a pair of simple cotton panties. White ones, I see, with baby-blue lace trim and decorated with little blue flowers. They're low-cut, but comfy and modest, almost fully covering her bottom. I let go of her jeans and they fall down around her knees at the floor. Her panties come down the same way, slowly baring the firm and rounded globes now pulled taut as she lies over my knees. I stop those a few inches down her thighs, and that's where they stay. About mid-way between her bottom and her knees.

I caress my hand over her cheeks for a long moment, feeling her silky soft and tight skin. And feeling her firm muscles underneath, with just enough sponginess to them to feel girly instead of manly rock-hard. It's definitely one of the better bottoms for spanking. I caress a little more, feeling Hailey relax at the tender caresses even as I scold her. "It's time you learn to have those slutty little naughty thoughts of yours on your time. GrubHub certainly isn't paying you to let your mind stroll through the gutter! Well, now you've been tardy with the wrong customer. Now your slutty little bottom is going to learn a very good lesson, slut. Ten spankings for that naughty little bottom, slut."

I raise my hand up, about halfway to my highest, and slap down on her cheek. Hailey squeals a tiny "mm." with the slapping swat. As I raise my hand up I see a faint pink hand-print that's already starting to fade. Without giving Hailey a rest, I swat her the same on her other cheek, getting another little "mm" squeal from her. I love her squeals. Hailey has a somewhat deep voice, not manly, but more whiskey. Like Stevie Nicks. That's who I always think of when I hear Hailey's voice. Plus she squeals about just everything.

"One, Ma'am. Thank you, Ma'am. I'm sorry for being tardy, Ma'am." Hailey counts the strokes of her spanking.

I pause for a second, caressing my hand over the skin of her cheeks very gently. With the first little motion, I feel Hailey's body, tensed from the swats, fade into relaxed again. After finishing with her globes, I allow my hand to glide up to her back for an instant. Then it's just the tip of a single finger that slowly traces its way down the crack of her bottom. Hailey purrs from that and doesn't even tense as my finger makes its way across her tight ring.

My finger keeps going down, and an inch later it finds the dense jungle of black fur on her lips. While Hailey's body stays relaxed, I feel her lips twitch just the tiniest bit as my finger strokes down the slit where their edges meet. It goes slow, stroking its way fully down the edges of her lips. Eventually, I feel the small bit of her loose folds, where their edges peek beyond her lips. I know that her sensitive nub is somewhere in those folds. I keep my tease very light, barely touching her, so I don't touch that. Not yet. I trace the line all the way down, to where her lips end and my finger is finally touching nothing but furry pubes. Then it's back up as tenderly and slowly as it went down.

When my fingertip finally makes it out the top of her crack, I allow my hand to return to her back. Then I spend a few sweet seconds caressing her cheeks before I lift my hand once again for her second stroke.

I swat her bottom just as firmly as I did with her first stroke. I swat her cheeks in rapid succession, one right after the other, giving her barely enough time to squeal her yelp after one before the second is slapping on her other cheek and getting another squeal. She squeals just a hair louder this time, her cheeks still feeling the light sting from her first spank. She obediently counts her stroke, number two, this time letting a hint of aroused honey creep into her voice.

I caress her cheeks again, leisurely and tenderly. Immediately she's relaxed over my knees again. I caress her lightly burning cheeks for another few seconds. Then my finger traces its line down her crack, over her slit and back up again. My finger takes its time, the tease being as leisurely and unhurried as it is affectionate and enticing for her.

Now, as my fingertip finishes its stroke, it reverses. Her second swat deserves a second tease to go along with it. It slips down with the same leisurely pace and tender touch until it passes the tight ring of muscle between those cheeks. Then, as soon as it finds her moist slit, it presses just a little more, slipping in between the edges of her lips, but not going any further than just between those bare edges. It continues tracing downward. This time, as it glides through those wrinkled little folds, I feel the tiny stone-like harness nestled in them. Hailey feels it, too. I hear her suck in a deep gasping-half-moan as my finger fleetingly glides across it. My finger goes all the way down, fully out of her slit and into her pubes, before reversing its way back up for another, slightly deeper teasing stroke.

After that line, and a few seconds of very gentle caressing to her globes, my hand is delivering her third spank. Hailey yelps with each the blossoming arousal in her voice drowning out the faint hint of pain from those swats. As she counts her third stroke out, I lift my hand to see the light pink handprints on her white flesh. Handprints that are still light enough that they'll soon fade away.

Her third spank deserves a third tease. I am not hurried. I am enjoying spanking Hailey like this, probably more than she is enjoying being spanked. So I take my time affectionately caressing her tight cheeks. Then I repeat both of the teasing strokes, doing them exactly as I did before, the first one so lightly touching her, the second one touching a little more. Then it's time for her third tease-stroke. This one is the same, only on this one my finger slips a little more between her lips. Far enough that I can feel the heat of her pinkness behind them, and I feel more of those wrinkles. I feel her little nub, too, and feel her body shiver as my finger glides across its top. As my finger slips back up from her lips after the stroke, it has a coat of her wetness clinging to the very tip of it.

Spanking number four, one firm swat on each of her youthfully taut cheeks, finally turns her squeal from "mm!" to "ow!" as my hand slaps down on her already stinging bottom. But I hear the arousal in her voice, even as she yelps out "ow."

And naturally, a fourth spank deserves a fourth tease. After she "suffers" through a full unhurried repeat of the first three that is. This fourth tease is just as light and gentle through her crack. And just as sweet through her lips. Until it finds that hard little pebble between those folds. Once it finds that, my fingertip takes a brief detour on its way down her damp slit. Just enough of a detour to circle around that nub a single time, stroking affectionately around its edges before resuming its trek over the nub and down her slit. On the way back up, it takes a detour as well. Hailey thanks me for the detour by purr a little moan as I'm teasing that nub.

Her fifth spanking brings slightly more strained squealy yelps of "ow!" from her. But the still-light pinkness of the handprints on her cheeks says it's not really hurting her yet. But she is definitely feeling her punishment.

And of course, there's a fifth tease to go with a fifth stroke! It wouldn't be what I've taken to calling a "slutty spanking" if there wasn't as much teasing as punishment in it! Naturally, I repeat the first four teases exactly as they were done the first time. And I know Hailey is wondering just what more this tease is going to add to that fourth stroke. Almost as soon as my fingertip slides in between her lips, I feel the wetness of her pussy. It's there my finger takes a new detour, tracing an erotically tender and torturously slow circle around the rim of its entrance, not slipping into her pussy, just around the rim of those walls. Hailey moans out a long "oh!" drawing it out the entire time my finger is making that circuit. While she purrs that sweetness, her hips shiver a little harder. Then it's down a bit until it makes a second detour around her clit. And back up, now with two detours in its trek.

Her sixth spank leaves slightly brighter handprints on her bottom and gets the first real, but faint, hint of pain in her voice. Not so much she doesn't submissively keep her bottom very still for me to spank, though, just enough of a hint that I know she's feeling the sting of her spanking.

Whatever sting she's feeling, it's forgotten by the time my finger gets near her asshole on its first teasing stroke. I'm sure by now her body knows quite well that she has five very sweet teases coming. And it gets all five of them.

Then there's the sixth tease. I'm equally sure she knows by now there will be a sixth tease. Just not what it might be. She soon finds out. Almost as soon as my fingertip is in her slit for this stroke, it's making its detour around the rim of her pussy. And the very instant it finishes that lap, my finger is straight and stiff as it starts slowly inching its way inside her pussy. I have small fingers, but I'm a small girl. They're as short as they are narrow. But even as short as my finger is, it takes a moment to slip all the way into her very hot, and nicely wet, pussy. A moment Hailey spends moaning a very honey-laced purr as her hips shiver. My finger stays in constant motion, reversing to ease out of her just as soon as it's all the way inside. Once out, it continues its trek downward to tease her clit, then beyond, before reversing up to tease everything all over again.

The seventh stroke adds a little more strain to Hailey's squeals, and darken my handprints up another faint shade. By now I feel the sting in my hand, so there's no way Hailey isn't feeling it in her bottom. But she stays still over my knees. And the tension still ebbs from her the instant she feels my tender caresses over her newly stung cheeks.

She purrs her soft moans almost as soon as the first tease starts its way down her crack. An eternity before my finger is teasing her clit and another eternity before it's teasing her pussy. For the seventh tease, my finger again slides into her pussy, slowly inching in to its fullest, just as it did for the sixth tease. Then it slips back out again, repeating the tease exactly. Only now it traces around the rim of her pussy a second time, which alone gets a good little anxious shiver from her hips. And then it slips into her pussy again. Only this time, my finger isn't still as its inching into her. The tip of my finger wiggles slightly, massaging the nervy insides of her spongy soft walls as it enters her. And as it slips from her a second time. Hailey barely stays still for it. I can feel her struggling not let her hips squirm as she purrs a very sweet, and eager, moan. She knows not to let her hips wiggle during a spanking. I insist that her bottom stays very still for the entirety of a spanking. I insist that she very submissively lies there and accepts the spanking I've chosen to give her. That she keeps her bottom still to make it easier for me to spank it, no matter how much her bottom stings, or her pussy aches.

Now it's time for her eighth spanking. Even though the pinkness of her cheeks shows me that her bottom is feeling the sting of the spanking, I don't ease up on iota. She gets this one just as firmly as she got the first seven, which is about half as hard as I could make them. It's enough for her to yelp a good squealing "E-ow!" as they slap on her tender cheeks, and I feel her body tense as she flinches from the swats. But it's bad, and she loosens right up at the first gentle touch of my caress on her bottom.

Hailey purrs loudly, and very urgently, through all seven of her teases. Those haven't speed up even a hair, either. They're just as leisurely as they were the first time she felt them tracing up and down her body.

As the seventh tease finally ends, I doubt Hailey is thinking much to wonder about the new addition. She's too busy purring loud moans and shivering. And now there's plenty of goosebumps dotting her cheeks to show off just how hot she's getting. My fingertip starts its trek back down her crack. By now her crack is well lubricated to an oily slipperiness with all of the honey my finger has tracked up through it. A honey that leaves a glistening line all the way up between those rounded globes, and coats everything.

My finger takes its new detour atop the tight ring of her butt. Hers is small, but dark purple-brown, and wrinkly with tiny folds of flesh. There isn't a single hair here, her crack always shaven smooth as I demand of my toys. My fingertip presses gently on the edges of her ring, circling slowly around her muscle and massaging it sweetly, right on the edge: the point where her ring curves inward. It never tries to slip into her, only to massage that too-often-overlooked little muscle. Then it's moving downward again, to tease her pussy shamelessly, just as on the other strokes. Her aching, and now throbbing-hungry hard little button as well.

And now it's time for Hailey's ninth spanking. Again she yelps pained "ows," her yelps getting a hair louder, and pants a few quick breaths after this spanking. She counts it off, and then she purrs so happily as the teases begin again. She purrs very eagerly all through them.

The ninth tease begins just as all the teasing treks down her crack and through her lips have begun. I'd hope by now she's been around enough that she has a guess what the newest addition to her teasing is going to be. Or at least a clue. As soon as my finger has finished its circle around the rim of her butt, it slips to the very center of her hole. I press with a steady gentle pressure, and her butt doesn't resist me. Hailey purrs as her muscle allows itself to be gently stretched a little. And as my finger, slick with her honey starts slipping into her bottom. While I feel her muscle snug around my finger, I don't feel it squeezing me or resisting. Just stretched, like a thick rubber band, around me as I enter her there. Just like with her pussy, I allow my finger to inch it's way fully inside her. And with a smooth movement that has my finger seeming to never quite stop, I reverse and slip it back out of her. Then down, to tend to her aching pussy and clit. And back up, teasing everything again before her "rest" ends.

Now it's time for her last spanking. I know Hailey will be glad about that. This time her squeals have not just that note of pain of to them, but I hear a light sobbing creeping into her voice as she counts off this last stroke. A stroke that leaves her cheeks glowing a medium shade of bright pink. It's still nothing that won't fade fairly quickly, but it's also enough that her cheeks will be feeling a pretty decent sting.

Her sobs vanish with the first of my caresses. Her purred moans take over even before my fingertip starts it trek with the first tease. A series of teases she knows will be coming. She gets all nine, just as slowly, and maybe even a hair slower, than last time. And now, it's time for her final tease.

It starts at the instant my fingertip is slipping from asshole. Instead of fully exiting her and moving downward, it reverses for a second slide into her bottom. Hailey purrs. At first, this stroke isn't any different, just an extra one in her backside. Until the tip of my finger emerges from the thick ring of her muscle inside her. No longer surrounded by that tightness, it moves downward a bit, pressing lightly against her insides. The tip of my finger starts massaging her insides with soft, slow, circles. And it's massaging her directly atop those very-excited and nerve-laden walls of her pussy, pressing down lightly, but enough that its massages are felt more in her pussy than anywhere else, as my finger continues sliding deeper into her bottom. Hailey screeches a long and very eager moan. The most sensual and guttural moan I've heard from her yet tonight. My finger keeps going until all of it has slid into her butt, reverses its trek, and slips out of her to continue downward for the rest of her tease.

On it's way back, Hailey gets the very same tease. Except that, as this is the end of her spanking, I can't resist tormenting her just a little more. So once my finger is fully inside her bottom, teasing her pussy with its little massages, I stop the tease. And keep my finger right where it, and go right on massaging her with those teases.

I count slowly and silently to ten. Hailey pants out a louder and more needy moan as each second ticks off. And I can feel the shivers, now so constant it's more like a faint trembling, racking her hips. Once I reach ten, I tell Hailey "You don't want to be naughty now!" then I pause a second. "Now apologize for your tardiness, slut." I keep going, the pad of my finger massaging her tingly-eager nerves.

Hailey more moans out than speaks. "I'm sorry for being a bad girl and being tardy with your supper, Ma'am! Thank you so very much for teaching me such a good lesson, Ma'am! I am never going to forget this lesson, Ma'am! Thank you for spanking me like the naughty slut I am, Ma'am!" Hailey knows I like humility, and too much is far better than not enough. Not enough might get her further punishment! I want her apology to be sincere. In that slutty way, of course. Accepting her apology, my finger starts its trek back out of her bottom.

Once it's finished its trek up her crack, I lift Hailey's shoulder up sliding her off my knees and onto hers. She hurries to shuffle her knees and body until she's kneeling the way I taught her I'd expect. I leave her down as I rise and get a wet wipe for my finger.