The Test School Ch. 03

That quickly diverted the Headmaster's attention, as his eyes became fixed on her luscious breasts. Her skin, bronzed almost everywhere had become paler under her bra, her time to even out the tan greatly reduced over the last year. It didn't matter a bit to him, they looked as glorious as ever and he relieved his assault on her pussy for larger targets.

His hands cupped her breasts, thumbs landing and quickly playing with her rock-hard nipples. He got another moan from her, which he took full advantage of to plant his own aggressive kiss on her lips. The suddenness of the assault on both nipples and lips getting a small squeak from her. She thumped him lightly on the chest, not really wanting him to stop but eager to regain control of the situation.

The Headmaster backed off, more from surprise than the force of the blow, and she took the chance to turn away. A few, rather ragged, breaths passed before Ms Smith surveyed her surroundings and quickly her eyes found her desk.

Foreplay completed, now it was time for the main event, she thought, turning to the desk and tossing her bra to join her carefully folded skirt and blouse.

The bra flew, as gracefully as women's underwear can fly, towards its target but in a rare lapse of skill and diligence, it fell short of its destination. The garment landed with a thump a good metre short of its intended destination, ending up lying spread open in a dishevelled mess.

The Headmaster let out a sigh, but the decision was already out of his metaphorical hands, as his literal hand operated on autopilot, swinging fast and purposefully towards the unaware bottom before him.

SMACK!

The blow was louder than it was painful, but it caught Ms Smith entirely off guard and she let out a short, sharp, almost ear-piercing squeal of surprise. Both hands were immediately on her bottom as a defence against further strikes. She spun around rapidly.

"What was that for?" she squealed at him.

He merely pointed at the misplaced bra, as if that was an answer in itself.

"What?" she asked again, still angry.

The tiredness in his eyes seemed to have disappeared, and he placed an arm on her shoulder as he continued to point at the bra.

"Ms Smith, I know you're a rather excitable young lady," he began, voice dripping with mock seriousness, "but I'd be neglecting my duties as Headmaster if I allowed such a lapse in your duties to occur."

She looked into his eyes, curious to see if he was actually serious. He looked serious, though the tug of a grin at the corners of his mouth, a sign she'd learnt to look for after all the time she'd spent with the man, told a different story. Her bottom stung, she was a little bit frustrated she had actually made a mess in her office, and she knew it would delay sexy time, but if he wanted to play this game then to hell with it, she'd play to win.

Her hands left her bottom and moved in front of her crotch, clasping them together and using her arms to squeeze her breasts together. She allowed herself to slouch slightly, lowering her height ever so slightly so she could look up at him with innocent eyes.

"Headmaster," she began, pouting and doing her best to sound like a much younger version of herself, "have I been naughty?"

It was an award-winning performance, and it won another quick smack to the backside.

"Indeed you have, Ms Smith, and I'm extremely disappointed in you." he answered, struggling to maintain a straight face.

"Oh, Headmaster," she began, turning the naughty schoolgirl impression up to eleven, "I'm ever so sorry, please don't tell daddy."

She was good, he'd give her that.

"Under my roof, Ms Smith, I'm you father and I expect you to treat me with the respect I'm due."

"Oh, Headmaster, I mean, Daddy, you are a naughty one." she smiled playfully as she spoke. The Headmaster seemed to be getting back to his old self, and frankly, she was turning herself on.

"That's enough lip young lady, now you can start by picking your bra off the floor and putting it away like a responsible young lady."

"Yes, Daddy, right away."

She walked over to the bra, bending over as far as possible to give the Headmaster a good view of her panties as they rode high between her cheeks. He said nothing, passing up an excellent opportunity to deliver another smack as he eyed her panties. The small patch of dampness, and the delicious curves of her pussy were obvious through the panties, even as she walked her bra over to the rest of her clothes.

"Now come over here, Ms Smith."

She giggled; she hadn't done that in one of these sessions for a long time, maybe she was as tired as he was, or had been.

"This is not a giggling matter, Ms Smith, now come over here this instant."

His voice was sterner than she expected, almost scary, but she knew him well enough the effect was more exciting then terrifying.

"Yes, Daddy," she said, inadvertently letting out another giggle as she moved over to him. "Please call me Wendy, Daddy, I've been very good."

A look flashed across the Headmaster's face and for a second, she wondered if that had been enough to push him over the edge.

"I will, Wendy," he began, apparently not undone by her performance, "But you haven't been a good girl and I'll have to punish you to make sure you understand that."

Ms Smith, or Wendy, made a face and let out a sigh, now what was he going to make her do?

He noticed her hesitation and moved behind her desk, patting it for her attention.

"Quickly, Wendy, or things will only get worse for you."

Her desk had been painstakingly divided into two sections, one with a computer and all her knickknacks, the other was left immaculately clear in the event she needed space to work on a document or something. She'd never imagined the Headmaster would use it to work on her.

She climbed on her desk, hearing it groan traitorously as she put her weight on it, feeling her breasts swinging and the panties chafing after her earlier bending. The Headmaster gave her a moment to settle before he brought his hands up, swinging her legs on the desk and forcing upper body down, positioning her so she was resting on her hands and knees, pussy pointed out towards him.

Wendy felt herself blush, the position wasn't exactly dignified, like a dog on display for her master, and being made to do it on her own desk felt worse. Still, she knew where the situation was headed and playing along would only get them both there faster. She playfully wiggled her bottom as she turned her head to look at the Headmaster.

"Please, Daddy, I'm very sorry."

SMACK!

"EEP!" she couldn't help herself, he'd struck harder, though only from playful to 'slightly naughty.'

"Eyes forward, Wendy," he commanded, waiting for her to comply before he continued. "Why are you here Wendy?"

Because you were tired and horny, she thought but didn't say. "Because I was naughty, Daddy."

SMACK!

She didn't yelp, but her body recoiled from the blow and she felt her breasts swing from the movement, her own pendulums. What a sight I must make, she thought, before remembering how wet her panties already were.

"What did you do that was naughty?"

"I gave you a blowjob," she pouted, her bottom really was starting to sting.

SMACK!

"OW!" she cried, that one really hurt.

"Try again young lady."

Wendy let out a sigh, only mostly out of exaggerated submission.

"Because I threw my bra on the ground."

SMACK!

With a resounding, and embarrassingly damp note, the next slap fell directly on her pussy, far gentler than the earlier blows, but somewhere a million times more sensitive.

"SIR!" she squealed, as the initial pain was replaced by an overwhelming tingle that spread through her crotch and lingered for an awkward few seconds.

"One more try, Wendy, get it right this time."

She rolled her eyes; he was getting a little too into this.

"Because I threw my bra on the ground, Daddy," she answered, sounding sullen and made a mental note to get him back after this.

"Much better," he said, rewarding her with a gentle rub of his knuckles along the damp spot on her panties, getting a low moan in response.

She couldn't help but push herself against his hand as he did so, though that quickly brought the stimulation to an end.

"All right, Wendy, why do you think you should be punished for throwing your bra on the floor."

"Because it's naughty, Daddy."

SMACK!

Blow landed on her cheeks, his hand returned to massaging her pussy through the panties, sending a tingle through her body that did a lot, but not enough, to mask the stinging from her bottom.

"Think harder, Wendy."

She frowned, trying to work out what he wanted, taking his commands a tad too seriously.

"Because I made a mess, Daddy?"

SMACK!

"Harder, Wendy," he replied, back to massaging before he'd even opened his mouth.

Good roleplay, if that was still what this was, is all about going with the flow and while she'd have loved to answer his question, she was out of ideas.

"I don't know, Daddy," she replied, voice dripping with sexiness in the hope it would get her out of this mess and back in business. "I'm just a naughty girl."

SMACK!

The blow to her pussy echoed around the room, and Wendy again squealed in pain, but also in excitement. The impact sent a wave of warmth out from her pussy, down to her toes and fingers, and all the way to her head. Not yet! Her mind screamed, fighting her body's urge to start shivering in delight. It was only then that she noticed the Headmaster had left her pussy alone after the blow, she did her best to peek behind her without getting spotted, but he'd gone.

A sudden pinch at her nipple gave her a hint as he began tugging at her breast, she only found it harder to fight the growing warmth inside her body.

"You're lucky you have such great breasts, Wendy, you're going to need them," he said, regretting the words as they came out, knowing he'd regret them even more when she had a chance to do something about them, but it was too late and he had to soldier on. "Throwing your bra on the floor shows a lack of care and respect.

BITCH! She screamed in her head; she'd shove some 'respect' where it hurt after this was over.

"Sorry, Daddy," her tone was as menacing as possible, he needed to know that was going to cost him. "I didn't mean to be disrespectful."

SMACK!

With one hand still groping a breast, the other hand was only able to deliver a playful blow to her bottom.

"Do you understand how to be respectful with your clothes?" he asked, slightly less confidently after the heap of trouble he'd earnt himself.

"Yes, Daddy, you take care of them and put them away properly."

SMACK!

"Then why aren't you doing that now?"

She had only a moment to be confused, The Headmaster released her breast and moved behind her. A single finger rubbed up and down the wet stain on her panties, before it hooked underneath them, peeling the damp material off its moist host and exposing her pussy to the fresh air.

Wendy let out a small gasp, the sudden cold was intense, his finger brushing directly against her pussy now the panties were gone, felt insane. She shivered, but that only encouraged him and he moved the panties to the side, allowing the lips of her pussy to keep them away as he commenced a gentle massage.

The urge to cum grew quickly within her, as his fingers knew exactly where she was most sensitive, but as she began to tense up, he withdrew them.

"Do you think that someone who takes care of their panties leaves them in this condition?" he asked. To drive home the point he grabbed said panties and started wiping her thighs with them, leaving a smear of her own juices where he rubbed.

"No, sir."

"Sir? You must be starting to take this seriously."

He was so going to pay when this was over.

"Of course, sir, I always take what Daddy says very seriously."

The Headmaster's eyes rolled back into his head for a moment, horny and in the submissive position, she was still scarily good at pushing his buttons.

"Then what should you do with them?" he asked, resumed his rubbing and keenly aware of how quickly she seemed to stiffen as he did so.

"Take them off?"

"Very good."

He removed his hand from her crotch, allowing Wendy to kneel upright and start pulling her well and truly damp panties down her thighs. As soon as they were clear of her waist, the Headmaster moved back in, using his hand to cup her pussy.

It took a moment, but as the heat from his hand, or her own warmth reflected off him, she let out a sigh. All it took was his hand against her, his fingers rubbing against her clit and she started shuddering. Desperate to hold him off, she tried to move higher, but his hand followed her up. The panties were almost at her ankles, but she couldn't do anything with them as her entire body started tingling out of control.

Wendy shuddered, let out a squeak, then just when she felt the heat in her body become critical the hand pulled back, droplets of moisture falling to her desk as it departed. She wobbled precariously, unable to spend time being embarrassed at the mess she was leaving on her desk, but she did manage to regain her composure.

"Doesn't that feel better?" he asked, taking her panties from her. She eyed them as he moved, not trusting where he might put them, or stick them. Thankfully he merely walked over to the rest of her clothing, leaving the panties resting on, and almost certainly leaking on, the pile.

"Much better, sir, thank you." she replied, though as he put her back on all fours, she found herself missing what little protection they'd provided.

He gazed upon her naked form as she rested at optimal hand height and completely available for his use. Her hair fell down the sides of her face, keeping her blissfully unaware of his gaze as he searched every inch of exposed flesh for his next target.

Wendy jumped as a pair of hands slid between her knees, before gently sliding up the inside of her legs. With every movement the hands rubbed her smooth skin, sending first a tickle, then a tingle, then a rush of excitement up her thighs. She could feel her pussy twitching in anticipation as the hands got closer and as they did, she felt them increase the pressure, trying to force her legs further apart.

His hands stopped just below her pussy, close enough that each twinge of excitement from her body brought them into contact with her swollen lips, sending a wave of joy though her, until the hands were withdrawn. He was teasing her, and he was good at it.

She bent her head down, looking between dangling breasts at her crotch. She could make out the Headmaster behind her, his exposed cock right behind her, though still disappointingly far from her pussy.

Her staring was interrupted by the appearance of his hand snaking its way between her thighs. It moved slowly, careful to avoid touching her as it moved, his palm facing up towards her eager body. When it reached its arbitrary position it began moving upwards, sending a tingle of anticipation down her spine as it got closer to her body. The hand landed with a warm smack on her belly, but it was not alone. The second, unseen hand had mirrored the first above her body, landing with a similar warm smack at the very top of her bottom.

Wendy let out a squeak of surprise as her body twinged, feeling herself sandwiched between his hands. The hands began pulling backwards, or down, along her body. She watched the visible hand slide down to her hips, then past her pelvis, until it was resting amongst the stubble above her pussy.

The other hand she could only follow by its touch, as it slid between her cheeks. This hand moved slower, its presence more tantalising. The further it went, the more his fingers disappeared, until only a single finger was tracing its way down her body, stopping just above her anus.

She unconsciously started clenching, her anus winking shut as best she could manage it, showing the owner of the hand exactly what he wanted to see. His hands, or rather his hand and a finger were poised -- one by her clit and one by her anus -- both pushing against her, as though it were possible to forget their presence without the reminder.

Wendy exhaled, just a little, and the hand in her crotch slipped accordingly, coming into contact with the top of her clit. She bit her lip, fighting back the urge to squeal again. With every inhale, her body moved the hand away, with every exhale it brought the hand straight back. Every deep breath she took, brought just enough pressure from the hand to send a jolt of electricity down her legs.

On the other side of her, the solitary finger brushed across her anus, this one drawing yet another squeak and sending yet another droplet falling from her pussy. The finger began circling her anus, riding the ring dividing inside and outside and sending her body into a wave of convulsions as her body tried desperately to close itself off even tighter.

She was about to scream at him to stop, or maybe to get it over with, or maybe even to beg he insert it, when the finger started pushing. A wave of heat rippled across her body, followed moments later by a radiating sting as he forced his finger against her body's design. She fell slightly forward, trying to brace herself against the assault.

Slowly his finger pushed past her resistance, drawing a small giggle of all things from her. Her sphincter closed around the finger even as it continued to push deeper. She could feel it inside her, just the tip initially but growing worryingly larger as she was struck by a wave of cold sweat. Her body clenched around the finger, not understanding that this was not a stool it could expel, but a foreign object that was coming in regardless of what she did, stinging her anus as it kept coming. Her body felt heavy, as all the air in her lungs seemed to empty, she'd been holding her breath without realising it.

"Shit, fuck, shit, fuck, fuck!" she gasped, knowing he was getting exactly the reaction he wanted. The finger kept pushing, already feeling far deeper than any finger could feasibly be. Suddenly the pain spiked, drawing another gasp, as the resistance at her sphincter grew. The pressure against it increased, though the finger inside her seemed to have stopped growing, until his other hand moved lower, brushing her clit for a second.

She squealed again, but the resistance in her anus relaxed for a second and, with agonising slowness, she felt the knuckle in his finger push through, every nook and cranny of the bone prodding against her sphincter, until it fought its way through.

The Headmaster stood motionless for a moment, feeling her boiling heat, her rapid breathing, her racing heartbeat, all through the finger he held inside her. He smiled, knowing how close she was. He brushed his free hand over her clit, feeling her stiffen around his inserted finger in response and he began massaging her pussy again.

"Doesn't it feel better when you're responsible?" he asked, giving his inserted finger an experimental twist, groping her in the most intimate way possible, pushing against her walls but not yielding a millimetre of depth it had gained.

Wendy was in no state to answer as every part of her twitched and shuddered, the heat growing in her pussy and anus overwhelming her legs and arms. She was breathing fast, she'd started doing it to work through the stinging, but now it was about holding herself together. She clenched her sphincter hard against his finger, a sharp pain running up her spine. It would have brought her back from the edge but the Headmaster was wise to her tricks, and he used that exact moment to counterattack, inserting two fingers into her pussy.

They didn't go deep, but they didn't need to. The sudden pressure in her pussy was quickly matched by the pressure in her anus, which only increased the pressure in her pussy again. It was as if both parts of her body were fighting over which would cause the orgasm, ignoring the fact that their owner only had so much capacity for stimulation.