Chloe and James

Chloe let go of the hem of her skirt, allowing it to fall at least more-or-less back into place. She was just beginning to try and think of where they were in the scenario and what came next when, quickly, suddenly, with a perfunctory "now then," James had ahold of her shoulders, was spinning her around to face the desk, was pushing her towards it and then bending her over it, pushing her down. Chloe gasped as the desktop came up to meet her and then let out a little sigh of relief as James slowed her and insured a soft landing (after all, it wasn't as if she could use her hands to catch herself!) and then he was pushing her forwards, her breasts compressed, her blouse sliding across the dark polished wood, brief vertiginous panicky sensation as he pushed her petite frame so far forward she felt her balance go, heels leaving the floor and hurriedly rebalancing as best she could on tiptoe. Chloe let out a startled squeak as James grabbed and flipped-up the hem of her skirt, exposing her bare ass to the air...and to its punishment.

There was a pause, which Chloe wondered about for just the briefest moment before realizing James was admiring the view. She'd been self-conscious about her butt for, well, as long as she could remember -- had always thought of it as protruding too far, especially given her relatively narrow hips, had thought of it as a "bubblebutt," despite its muscular firmness. Early on in their relationship she'd been sure James was just flattering her when he'd told her how hot he thought it was, that he found it one of her most attractive features. She'd finally begun to believe him when the relationship had gotten physical, when the almost worshipful attention he lavished on it had at first embarrassed then begun to relax her...to the point where here, a year or so into things, she'd agreed to do a spanking scene with him -- and found herself getting heartily into it.

And now she could feel his hands on her ass, gently massaging her asscheeks, now spreading them, now kneading them, working in a cirucular motion most of the time, starting up near the small of her back, working his way steadily downwards and inwards, towards her pussy...where Chloe felt the glow of their previous upskirt play returning. She shifted a little on the desktop, trying to get a little more comfortable, realized how stiff her neck was going to get if she kept holding her head up like she was and lay it down on the desk, turning her head and almost turning it to the other side as she caught sight of the torn and...well-moistened...remains of her thong lying only inches from her face. She could smell her own scent coming off of it quite strongly, which brought back a vivid replay in memory of earlier-on in the scene...

James stopped his massage just short of Chloe's pussy and changed his technique, now stroking and caressing her buttocks, now tracing a fingertip ever-so-lightly down the cleft between those cheeks...finally reaching, pressing gently, gently against the rear juncture of another cleft...Chloe purred softly in her throat as he stroked this cleft, just a little...

Then suddenly jumped as he jerked his hand away and snapped "Chewing gum in class! Eight strokes!" The blows rained down in rapid-fire succession, alternating cheeks, four on the upper outside section of each, delivered with the slightly cupped palm of James' hand as Chloe yelped and jumped and squealed and writhed.

A pause afterwards, as she caught her breath, felt the spreading warmth in the cheeks of her ass...warmth that, she realized, was already somehow extending to her pussy. She felt herself suppressing the strangest urge to try and push herself at James, to encourage him to resume the spanking.

Not that she had long to wait. "Second infraction: too-short skirt, seven strokes per inch under regulations!"

Uhhm, how many inches under did he say I was? Thought Chloe dazedly. Oh, yeah, two...which makes fourteen...

Chloe jumped at the first swat, and the second, which came right after, and then the third...and then there was a pause. After a couple of seconds the fourth blow came down, this time on the same cheek as the third. Then another pause, and then James' hand was down on the opposite cheek, only gently, caressing it, stroking and lightly squeezing before running a finger lightly down the cleft of her ass before cupping her pussy and gently squeezing her still-swollen labia together. Chloe groaned and reflexively pulled at the tie around her wrists, then found herself pushing herself at James as he lightly rubbed the outside of her lips. She suddenly realized just how much she still wanted the release he'd been so close to giving her while trying to get her to admit out loud she was enjoying herself.

And then his hand was out from between her legs and its open palm brought down sharply on the asscheek he'd just been caressing and massaging. Another blow on the opposite cheek after just a second's pause, then another pause and his fingers were tapping at her...there...once, twice, again, Chloe gasping at the sensation each time.

Then two more strokes, following quickly on each other, this time on the lower inside part of her buttocks -- Chloe could feel the jolts carry through to her pussy, almost like an attenuated version of the taps he'd just been giving. She whimpered softly. And then his hand was between her legs again, a single finger dipping this time into the cleft, stroking up-and-down most of its length, unhurriedly masturbating her as she felt her orgasm beginning to build again. Soon she was rocking back and forth in time with James' caresses, making little noises in her throat as she did.

After only a few moments of this, his hand was again out from between her legs, cupping and stroking first one cheek of her ass and then the other, taking ahold of them with both hands and massaging in a circular motion that had her groaning appreciatively. And then two more blows, Chloe crying out, having gotten lost enough in the moment to almost have stopped expecting them. Another pause for that circular massaging, then two more strokes, then his fingers were there again, two of them dipping between her thoroughly moistened labia this time, sliding forward and spreading her open. Chloe moaned, low in her throat, then cried out sharply as the tips of those two fingers found her thoroughly sensitized clitoris. Once again those fingers pressed into the flesh on either side of Chloe's clit and began slowly moving back-and-forth, again rubbing the skin of the hood over the more sensitive regions it covered.

Gradually James picked up the tempo. Chloe found herself moving with him, rocking herself back-and-forth as well as she could off-balance as she was while pulling and straining at the tie and realizing how much the sensations of immobilization were contributing to her arousal -- and, she was sure, the intensity of her impending orgasm. She began to vocalize as the moment approached, little -- then not so little -- grunts and groans and moans, when once more James' hand was out from between her legs and immediately two more strokes, again on the inner lower quadrant of her asscheeks, making her jump and yelp more than ever as the attenuated force of the blows again carried through to her pussy. The last two blows of this particular punishment, Chloe realized, as James counted aloud "Thirteen! Fourteen!" as he brought his hand down and then stopped.

After a couple of seconds Chloe noticed how much she was shaking there on the desktop, how her breath had begun coming in ragged, shuddery gasps. Her head was spinning as she tried to remember what was next, what infractions remained. She wondered what their punishments would be.

She didn't have long to wait. "As to your next offense, skirt instead of scooter with, shall we say, unnecessarily revealing underpants beneath. Let's see...let's see...normally either of those alone would be a half-dozen strokes. In combination, an even dozen -- plus two more for your incurring both infractions at the same time!"

Chloe tensed in anticipation, a little smile coming to her lips as she waited for the blows to start raining down, no doubt with pauses for...benefits...between them. To her surprise, there was a delay as James continued speaking.

"I couldn't help noticing certain noises you began making towards the end of the punishment for your last infraction. Most unladylike, I'm afraid something must be done about it before we continue. One alternative that comes to mind would be to gag you with the remains of your inappropriate underwear," said James.

Chloe's eyes were drawn to the shredded sodden thong lying near her face on the desktop. He wouldn't, she thought, at the same time wondering whether he in fact would, and feeling not quite sure whether she was more repulsed or -- much to her own surprise -- turned-on by the idea.

"A second alternative," continued James, "would be to have you concentrate on maintaining more appropriate vocalization, say by keeping count aloud of the individual strokes of your punishment."

Chloe said nothing, until James picked up the remains of her thong and went to pinch her nose shut (to force her to open her mouth) and she found herself blurting "I'll count! I'll count!"

James dropped the panties within inches of her nose and commenced administering the next two dozen strokes.

"One!" cried Chloe, turning her reflexive yelp into a word. "Two!" less than a second later, on the other cheek of her ass. It started out pretty straightforward, James spanking Chloe slowly enough for her to count easily, with longer and longer pauses between to feel her up, first massaging her ass then, as the strokes themselves worked their way closer to her genital region, he returned his attention to Chloe's pussy. Teasing, at first, just sliding a fingertip lightly up and down the length of the outside of her cleft for a few seconds before withdrawing his attention from there and returning it to her "punishment."

"Three!..Four!..Five!" Chloe called out, in time with each smack. "Six!"

Back between her legs, now, more intimately this time, venturing back between her labia, teasing at Chloe's entrance, tugging at her inner folds, indirectly stimulating her clit, getting her ever more excited as she groaned and whimpered her appreciation, again pulling at her bonds in a sort of instinctual attempt to join actively in the fun, that attempt's frustration somehow taking her even higher...

"Seven! Eight!..Nine! Ten!..Eleven!," the words coming out in a strange half-choke, half-sob as Chloe fought to retain enough control of her breath to form the words.

And then James was grasping her by the hips and pulling her backwards, away from the desktop a little bit, her weight returning to her feet as she rocked back off tiptoe onto the flats of her soles. She frowned slightly, wondering what he might be up to, then her eyes went wide and she gasped as his hand was once more at her pussy -- in fact immediately and assertively at her clit, this time not from behind, but reaching around and beneath her, two fingers spreading her while the one between them penetrated to the second joint, its base pressing against the hardened little ridge of her clitoris. No teasing this time: James immediately began jiggling all three fingers rapidly from side to side. Almost as immediately Chloe was gasping, moaning, panting, grinding herself as best she could and beginning to babble nonsense as the orgasm James had been teasing her so by withholding so long built and built and built...closer and closer, even closer than before, no stopping it now she was sure of it...trembling now, hips beginning to buck up-and-down...

And then he was stopping. Pulling his hand away yet again. The briefest little pause, maybe a second, both of them knowing what was coming (Chloe not completely sure she wasn't)...

"Twelvethirteenfourteeenn!" Chloe surprised both of them by somehow managing to keep count as the final three strokes rained in rapid fire succession on alternating centers of her asscheeks, crying-out the first two numbers, half-panting, half-gasping the last, glad she had the heavy desk to lean forwards into, to take some of her weight off her now-shaking knees.

For a moment she just lay there, shuddering, trying to catch her breath. Just long enough for her, through the haze, to begin to wonder "what next?"

"Now," James breathed -- almost panted, really -- Chloe noted as she realized the extent to which he'd been teasing himself, too, holding back even as he kept her held-back, "there remains the issue of your...choice as to hair removal. What might be an appropriate punishment for such an infraction? Ah, I know..."

And Chloe, suddenly, knew too, even before the sounds of belt and zipper being undone, even before James firmly grasped her hips, pulling her backwards as he drove forward...

Chloe screamed as he entered her -- surprising them both, she wasn't usually that loud -- fast, hard, all the way. And then that scream was followed by another as James partially withdrew only to plunge into her again, the harsh, jabbing thrust filling her as his cock again buried itself to the root inside her.

And then he was fucking her, hard and fast, not bothering to pace himself or slowly build speed, though Chloe was already so wet it didn't really matter. Again, some part of her mind was struck by how much their play had teased them both even as she grunted and moaned and panted and gasped, pushing back against James' thrusts as best she could from the position she was in as her hands jerked and twisted in her bonds, clenching and unclenching into fists, into claws...Chloe's gaze happened to fall on the shredded remains of her thong. Though the thought of being gagged with her own soiled panties was...maybe a bit much....she found the thought of being muffled or gagged in some way increasing her excitement even further. Definitely next time, she thought.

James wasn't going to last long, Chloe realized, and she found herself wanting him to finish inside her, willing him to, crying out for him to as she abandoned her attempts to actively meet his thrusting and surrendered to his pushing and pulling her by the hips, even harder and faster now -- any second,she thought...

And then suddenly James' thrusts slowed -- nearly stopped, really -- with him nearly all the way inside her. She had just enough time to start to be puzzled -- and just enough time for James to raise a hand to his mouth, unseen by her, and quickly wet two fingers -- and then his hand was once again snaking-around beneath her, expertly making its way between her legs...Chloe screamed yet again -- her loudest and most intense yet -- as his fingers found her swollen, mercilessly teased clit and then his fingertips were lightly, rapidly flicking back-and-forth across the taut hood and then she was coming, coming harder than she could recall ever having done, coming so hard she only noticed her knees buckling as James caught her, held her up, kept her from collapsing to the floor as she jerked and shuddered. She hoped he'd keep holding her like that, not the least because she wasn't at all sure her legs were up to the task of supporting her just yet.

And then he was standing her up, turning her around. When did his cock slip out of me? she wondered dizzily, did I jerk it out of me when I came? Did he come? Gently, carefully he sat Chloe down on the edge of the desk and took a step back, seeming to sway on his feet a little as he did. Chloe started to tip over backwards, caught herself with her hands on the desktop behind her. She realized with a start that her face was wet as she started to catch her breath. Whoa, she thought, talk about intense!

After a moment she noticed James' cock, still hard, and realized that he mustn't have come yet himself. She was just beginning to think in terms of what might be done to rectify that situation when James managed to get himself sufficiently under control to begin speaking again.

"Is that...is that lipstick you're wearing, Chloe?" he asked, his breath catching in a sort of gulped pant right after the first two words.

A moment of silent confusion, then she'd recovered enough to play along (though she wasn't sure yet quite where this was going), "Y-yes...sir," she stammered.

"I do believe it is not one of the colors we allow at his institution, Chloe," said James in his Stern Headmaster voice, "what..punishment...would be appropriate for this...infraction?" he asked.

"Ah! I know just the thing!" he added, just as Chloe was beginning to wonder whether he'd been speaking rhetorically or actually challenging her to come up with something. James slipped his hands underneath Chloe's arms and, not ungently, pulled her off the desk.

Oh God, he's not going to want me to stand up again yet, is he? wondered Chloe. Nope, she realized -- along with, at least generally, what James had in mind as he eased her down...onto her knees...his still mostly hard cock bobbed before her, almost exactly at face-level.

It wouldn't be quite the first time she'd given a hands-free blowjob, Chloe reflected as she parted her lips and started to carefully lean forward, though she had to admit not being able to use her hands was new. She pulled at her bonds, this time deliberately, the better to feel them, clenching her hands into fists as she did. She was stopped short of taking James into her mouth by him grasping her -- gently, yet firmly enough and close enough to her head to keep her from easily moving -- by the pair of schoolgirl-pigtails she'd tied her hair in, in preparation for the scene.

Chloe tensed-up a little and looked questioningly up at James as the head of his cock pushed past her lips. She was a little concerned about gagging, with someone else in control of depth and timing.

She immediately discovered she needn't have worried -- from experience, James had a good idea just how much Chloe could take, and it quickly became obvious he had no intention of exceeding that limit. Chloe relaxed, but maintained eye-contact with James as he began to fuck her mouth.

Unable to use her hands, or even to move her head much, Chloe soon found things getting a little messy as she began salivating in response to having her mouth...filled. Soon she could feel a line of saliva running down her chin, and dripping from it. She began to wish for things to be over soon, not sure she wanted herself covered in drool.

Almost as if on cue, James' body tensed, and began to tremble. Close since about the time he'd first entered her, he was now right on the edge.

This's it, your turn, thought Chloe as, making sure to maintain eye-contact all the while, she did a little something with her tongue -- something she knew from experience he liked and which demonstrated that, if she were a schoolgirl, she was a much naughtier one even than the Stern Headmaster had imagined.

And that was absolutely it. James' hips bucked, Chloe jerked her head back slightly (and a little painfully as her pigtails pulled where he still had ahold of them) to avoid being poked in the back of the throat and as she continued looking up at him saw him make that face, that familiar expression she'd so many times gazed up -- or down, or, on a couple of occasions, over her shoulder in a mirror -- at as her mouth was filled.

There was more of it than she'd expected -- he must've been saving-up, she thought -- and though she managed to swallow most of it the awkward confines of her position kept her from preventing a little bit escaping by the same route her saliva had been taking and, Chloe found, the thought of getting her blouse soiled had her again pulling her head back, this time more insistently and James let go of her pigtails, releasing Chloe's head so she could duck-down and spit the little bit she hadn't managed to swallow (and that wasn't already on her chin) towards the floor.