Chapter 5

For Holly Levine, having to strip naked for an inspection was quite normal. Nor was it that much of an issue to do so anymore with an entire three years having passed since her first semester at the St. Margaret’s Academy for Wayward Girls, and seeing as most of her other classmates had to go through the exact same thing as well, having to stand in front of an old and perverted man with her legs spread apart was far from the worst thing she had ever done. Or at least that was the impression she got when the head nurse waved her over towards him instead of one of the more regular stations like everybody else.

Rolling her eyes, she walked over to assume the standard position. Maybe she was just special, she thought sarcastically. Her parents liked to think so at least, which was sort of how she ended up at the school instead of somewhere else. Bother them and their insistence on traditional values. Truly, it was a plague on the soul. It wasn’t as if she was going to get a whole lot of pity here though, since the man standing in front of her seemed to be of the exact same disposition as well.

Richard Evans, his badge read. One of those fancy and laminated ones that they handed out to guests. Possibly that was how he was still here instead of being escorted off the grounds by the guards.

“Stop moving about so much,” he snapped, “And stay still.”

Holly blinked at the sharpness of the order.

“Sir, I just got here,” she said.

“And do you think that gives you an excuse to talk back?” came the reply.

He looked her up and down with the corner of his mouth twisting into a sneer, and very carefully she managed not to point out that she was just trying to state the obvious. Besides, it wasn’t as if it was her fault. Hadn’t he been the one to call her over in the first place, or did he somehow think that she was stupider than she looked? Like sure, she was still only a student so maybe she could give him some credit for that, but there was no way she was ever going to miss the glance that passed between him and the head nurse. And as his eyes traveled up her legs to rest against the inside of her thighs, she couldn’t help but notice the tell-tale shape of the camera already set out.

A Nikkon, a helpful voice whispered, one of the newer professional models that she recognized. Her father used to collect them to take pictures of birds, and then of her later on.

“Well?” said the man.

He tapped his fingers against his palm, and she waited for a full ten seconds before she bothered to reply.

“Well what?” she asked politely.

“Hurry up and undress,” he said.

“Now?” she said.

“When else do you imagine?” said the man, “Unless you think you’re doing yourself a favor by wasting my afternoon.”

He looked across at her again, this time with a glare, and she bit down. What exactly he had planned for her today he never bothered to say, but she could already hazard a guess. Possibly, it couldn’t have anything to do with the fact that the school had just started a yearbook program, and they needed someone to model for a couple of the pages. And since the current medical examination they were going through just so happened to be one of the most important highlights of the year, surpassed only by the reward ceremony where they would finally be allowed a climax, it was with a sense of resignation that she let out a sigh. Bollocks. Just her luck to be standing here while all her other friends were off having their privates teased by a nurse.

A moment passed and then another as the man waited there patiently. Like a hawk watching its prey, and taking in a deep breath she reached over to shrug off the layers of her uniform. Bit by bit the fabric peeled away, revealing the flat curve of her training bra along with her underwear, and each movement seemed to shed another thin piece of her already fragile autonomy from her soul. Then, with nothing but the thin fabric of her panties left to hide behind, she slid free of those as well before reaching over to place her hands on top of her head.

The cool air brushed against her back, and she shivered against the goosebumps that came from the exposure.

“Would that be all, sir?” she said.

It was a dumb question, but she ignored the voice criticizing her inside her head. Honestly, she didn’t know what else she could do. It seemed to matter anyways, however, as he slowly circled around her before reaching over to place a hand against her chest.

“Adequate,” he said, “Though I would have preferred if they would have sent me someone much more representative of the average student.”

“What do you mean?” she asked.

The words fell out of her mouth before she could stop herself, and the man scowled at her again.

“What I mean,” he said, as if she was being obtuse, “Is how on earth do they expect me to get any good pictures when you’re practically a twig?”

He reached over to pinch her with his hand, his fingers roaming over the sharp ends of her nipples along with her nearly flat breasts, and she winced as she bit down on her lips. Her other parts down below weren’t treated any better as he traced over the soft triangle of her vulva, and she felt a slight tingle echo up her spine as he reached over to press against the tiny little bump at the top of her slit. Over and over again like a button, and by the time he finally stopped she could already feel her legs starting to quiver.

Briefly, Holly closed her eyes. The fact that she had just managed to save up enough points for a quick pity rub at the end of the last semester was not at all weighing on her mind. Nor was the fact that she was still another dozen or so points off from even the lowest tier of a ruined orgasm, and if things continued on the way they did, it was going to be quite a while before she would be able to experience anything even close to a full-on climax.

The distant hum of the lights buzzed away above them, and she swallowed hard against the familiar feeling of frustration. Like a dullness inside of her that ached.

“I’m sorry,” she mumbled against the silence, “I promise to try my best.”

For all her sincerity though, the man appeared didn’t appear to notice as he reached over to spread apart her lips

“Do you now?” he said, “And I don’t suppose this is the proof of your enthusiasm?”

He ran his fingers through her folds before holding them up to the light, and she blinked as she watched a thin string of transparent guilt stretch out through the air.

“No sir, I mean…,” said Holly.

“You don’t mean anything,” he said, cutting her off, “Now be quiet and do as I say.”

He wiped his hands before waving for her to start, and she let out another sigh. Back to the usual schedule then, she thought, fuming inside her head. She did manage to keep her anger under control long enough to do as he asked though, and so after taking in another deep breath to calm herself down, she slowly walked over to the examination table to bend over the edge. Following that was the sound of the camera being set up behind her, and she moved her legs apart just a little more so that her bottom was centered in the middle of the frame. Including both her privates and her anus with the tightness of the two openings fully exposed, and then the only thing left to do was to reach back and spread herself apart with her hands.

Click.

The first flash caught her off guard, and she blinked as she felt the light bouncing off the shallow curve of her buttocks and the crevice in between. Like a valley of darkness through which the pinkness of her most intimate places could just be seen, and she bit down on her lips as the man waved for her to continue. Which she did rather obediently as she reached over next to open up the outer edges of her labia, and a second flash glinted off the thin membrane of her hymen hidden just inside the opening of her tunnel.

A soft glimmer of heat rose up inside, and the feeling was a bit like having to stand naked in public. Or having all her secrets shown off to the entire world. Like a perfect little doll just waiting to be used, and she winced as a pair of fingers reached over to peel back the covering of her hood.

“Stop squirming so much,” he said, “And quit leaking all over the place, you’re ruining my shot.”

There wasn’t much she could do about that though. Another hand reached over to push her hips further up, and she frowned as he zoomed in with the camera.

“Sorry sir,” said Holly, “I can’t help it.”

“Can’t help it, or won’t?” he scolded again, as if it was hardly an excuse, “Do you have no respect for your elders? Keep this up, and I might just even get the paddle to teach you a thing or two.”

Someone must have given him a prep talk beforehand about how the academy worked, she thought absently. Her fingers gripped the edge of the bench a little tighter. It took a bit more effort to keep her voice steady against the thought of being spanked in front of everyone else.

“I apologize sir,” she said, “It won’t happen a second time.”

She tried her best to sound sorry. Most of the time, sounding sorry was enough. For all her intent though she might as well be talking to a brick wall since the man simply reached over in the next moment for a plug. One of those small training ones that came with the school’s logo, and she winced as she felt the blunted end of the device pressing up against her rear hole. It failed to enter her, the roughness of the friction rubbing awkwardly against her anus, and it wasn’t until after another couple of attempts that he finally decided to reach over for the lube.

Right, of course. Holly winced. Clearly, this was something that he practiced every day. Not that she had much of a chance to complain since a small press of a button later was all they needed for the vibrations to start up.

“Ah,” she said.

She squirmed, her hips moving forward in a halfhearted attempt to escape, and a few more snaps echoed out from the camera set up behind her. To her surprise though, instead of launching into the usual pattern of stimulation she was expecting, the only thing that happened after that was another soft touch against her privates as the fingers returned to spread apart her labia.

Good, she thought. Let him think that was enough. Never mind the fact that she had to go through something like this every other week, or that the last punishment she went through was an entire hour of detention with a dildo stuffed up her bottom. All five inches of it as well with the base of the toy pressed up against her, and as much as it had hurt afterwards, there wasn’t single girl at the academy who couldn’t take something that simple. Meaning that so long as she was careful not to let her intentions show, then she might be able to get away with it after all.

The man reached over to trace his fingers around her clit again, and slowly the idea lit up light a lightbulb. There was another press, and she let out a moan that was louder than normal. Past that, it was over onto her back with her knees pressed up against her chest and her legs spread apart, and drawing the plug back out again, the man slipped a long string of anal beads up her bottom.

One by one they moved past her ring, each one of the medium-sized spheres measuring out at just under an inch in diameter, and she bit down on her lips as she felt the last one slide past her rear hole.

“Eyes up front,” he said, “And don’t look directly at the lens.”

The words that he didn’t say was that doing so would probably ruin the picture. It was hard to make herself care though as he moved the camera a little closer in towards her crotch. A marker made an appearance, and after a series of quick strokes across her rear, she looked over to find a series of black arrows drawn on both sides with the ends pointing towards her anus. How subtly wonderful. A work of art, even. Written next to it was her name and her grade along with everything else there was to know, which if the words ‘F for Failure’ had anything to say, wasn’t all that much.

“The worst I’ve ever had is a C- in PE, you know,” said Holly.

“And?” said the man.

“So why an F?” she asked.

Frowning, the man reached out to give her a soft tap between her legs in response.

“Because it looks better that way,” he said, “Not that a girl like you would know since the only thing you seem to care about is touching yourself when nobody else is around.”

Click… click… click…

Another series of snaps echoed out as he pressed down on the shutter, and she rolled her eyes. She really needed to learn how to keep her mouth shut. There was another touch across her folds, and a couple more seconds passed like that before she almost forgot to let out a shiver. Good thing she did though since she was rewarded rather brilliantly with a not nice at all smile, and squeezing her muscles down a couple more times for effect, she whimpered as she heard herself moan.

Possibly she was overdoing it, but it didn’t really seem to matter as the man leaned over her for one last shot. Following that was the feeling of being stretched again as the beads were slowly pulled back out, and as the last one slid free, she grit her teeth against the emptiness that lingered inside her hole.

“Ow,” she mumbled, half meaning it this time, “Be more gentle.”

Again though, it was a bit like talking to a wall. Stupid academy and its stupid little yearbook. They even had to bring in a third-party photographer for this, and the worst part about it all was that he had no idea how to even properly touch her. Which meant that instead of the sharp rise to the top that she was used to, the journey was more akin to a car slowly making its way over a broken and uneven road. The destination still grew closer of course, but the journey was somewhat hampered by the thousand little starts and stops. And judging by the swollen state of her labia, she could already tell that she was going to be feeling rather sore by the time it was over.

Better get on with it then, before they ended up taking another hundred years or so to get it done.

“How many more do we have left?” said Holly.

If it was ever going to be as simple as that though, then she would have tried to ask much sooner. The man scowled again as he waved for her to climb back up onto the bench. This time on her hands and her knees with her head pressed down against the surface, and she shifted in place as if there was nothing wrong with having her most intimate places shown off to the entire world. Like a rose, or perhaps a tightly packed chrysanthemum for her anus, though if taking pictures of plants was the theme of the day then she really didn’t want to think of who played the role of the gardener.

“We’ll stop when we’re done and not a moment sooner,” said the man.

“Does that mean you’re going to put something up my butt again?” said Holly.

“Such insolence,” he said, giving her a smack, “Though I wonder how that attitude of yours will turn out after a little touch of this.”

Before she could ask he donned a pair of latex gloves, and reaching over for a familiar looking jar, he unscrewed the top of the lid before scooping out a generous amount of the cream inside with his finger. Then, pausing only to set the container down, he applied a generous amount of the substance over the smoothness of her folds. All the way down from the pinkness of her clit to the opening of her tunnel, and after another pause to gather up some more, she winced as he moved over to do the same thing with her anus.

A gloved finger circled around the edges of her ring before pushing inside for a couple of quick thrusts, and she bit down. Slowly, the coldness of the gel gave way to the softness of warmth before the first embers of heat started to show, and then…

“Ah,” said Holly, for the third time in a row.

This time, the gasp that she let out was much more genuine. More than she was willing to admit. The man chuckled behind her, and she grit her teeth as her clit let out another throb. And not just because it had been quite a while now since her last climax since as much as she prided herself on her ability to resist, there wasn’t a single girl at the academy who could withstand the effects for long.

“Finally starting to feel it now?” he teased, “Or do you still want to keep up this pointless charade?”

“Right,” she mumbled, “As if this is even enough.”

Despite her bravo though, there was no mistaking the tremor in her voice as it leaked out. Like the whimpers of a well-worn pump, and not at all because the rest of her energy was being spent on keeping her hands where they were. Her fingers tightened down a little more in frustration as they gripped down against the edge of the bench, and she let out a shaky breath in turn. The last thing she needed now was another trip to the Headmaster’s Office for the crime of trying to touch herself where she knew she shouldn’t.

Her plans were somewhat ruined in the next moment though as the fingers returned to her labia again, and all of a sudden the world seemed to slide out from under her feet at the softness of the touch.

“I…,” she said, “Ah, can you…”

“And why ever?” he said.

“Because you don’t understand,” she gasped, “I can’t… it’s not…”

She tried again, but the words just wouldn’t come. Another series of spasms hit her, and she groaned as the frustration rose up. Like a throbbing deep inside her that hurt, and if only she had something to clench down against then maybe it would feel just a little more manageable. There wasn’t though, and so there was nothing she could do but swallow down the misery of having to stay bent over on all fours with her bottom lifted up.

The man reached over for the camera, and she closed her eyes against the sudden humiliation of the ordeal. Before it was much more bearable when her mind was still in control, but with the artificial arousal of the aphrodisiac now making its way through her system, it was hard to think of anything except how long it had been since she had last felt any relief at all. At least an entire year now, if not more.

The memory of the previous reward ceremony drifted through her mind again, of her standing naked with her panties stretched out in front of the entire school, and she closed her eyes against the thought. She hadn’t even been allowed to use her own fingers back then. Instead, there was only the frustratingly light touch of a feather as it gently coaxed her clit out from underneath its hood, and after another sixty seconds of torment in which she begged for the teacher standing behind her to please let her finish, the entire thing was over.

“Please…,” said Holly again.

The journey back to her seat was the longest one she had taken, and the cries of the next student in line did nothing to alleviate the misery at all. Especially since there was nothing left for her to do but keep her legs pressed together as she sat down with the rest of the girls. Hopefully, this year will be better. It had to or she didn’t know how she could put up with it anymore, to the point where even a simple ruined orgasm was starting to sound better than another year of frustration and denial.

There was one last touch against her clit, and she whimpered as the man pulled his hand away with a smile. Like the battle was already won, and she grit her teeth at the loss.

“Let’s do this,” he said, “There’s still another dozen or so shots left, but since it looks like you’re starting to realize the consequences of your situation now, I’ll cut you a deal. If you agree to meet for a follow-up session next week, I promise to complete the rest of the session in a much more accommodating manner. If not though, well…”

He held up the next couple of toys in line, a pair of nipple clamps followed by a speculum, and it was only through a sense of despair that Holly found herself considering the offer.

“And if I don’t?” she asked, hesitating for as long as she dared.

“Then the plug goes back in, and I turn the vibrations up to the maximum,” he said, “As it is though, all I need from you is a dozen or so more shots. Preferably with a much more pleasant expression if you can even manage such a look.”

“Like I actually want to be here?” said Holly.

“Exactly,” he said, “Like you don’t mind being naked at all.”

That was, well… she thought about it for another moment. Carrot and stick. That she could probably do. The offer was made even more tempting by the empty enema bottle she had already spotted hidden somewhere under the pile of tools, and as much as it sucked to be edged, it was going to take quite a lot more than that before she was willing to accept an entire liter of soapy water up her bottom. Even if the alternative was a repeat of the exact same thing only a week or so later.

Biting down on her lip, she thought about it for another split second before she finally let go. She was tired, she realized, and all she wanted to do now was to go back to her dorm.

“Alright,” she surrendered, "I'll meet for the follow-up shoot."

She looked over with a sense of dread, but to his credit the man didn’t try to gloat.

“Very good,” he said, “I’ll set something up this coming Saturday then. We can meet at 8:30am and take a break at noon for lunch.”

“Does it have to be that long?” said Holly.

“Well obviously,” he said, “You can’t rush perfection.”

Then with that little piece of wisdom laid out he disappeared back behind his camera, and it took her everything she had to smile. Just a couple more shots now, she told herself. Absently her hands reached down to either side, pulling her labia apart to reveal the delicate opening of her still virgin hole, and she blinked as a flash of light echoed off the walls to reveal the transparent stickiness of her arousal. Her anus twitched down below, winking up at the lens from between her cheeks as if begging to be filled, and she swallowed hard as she **** herself to be grateful. The only saving grace was at least he hadn’t tried to put the plug back into her bottom so far.

Click… click… click…

The halfway point was just a little further on. This time, it was over on her side with her head looking back over her shoulder and her bottom pointed at the camera. The quiet tick of the clock echoed out in half-beat increments alongside the snapping of the shutter, and bit by bit as she blinked against the light, she felt another trickle of fluid flow out past her labia. Her clit stood up again at the top of her slit, feeling as stiff as it always was, and closing her eyes she tried to focus on her arms. And her hands. And her skin. And the beating of her pulse as it echoed through her heart. Anything at all, she thought, to take her mind away from the frustration of her denial.

Taking in a deep breath, she held it in for as long as she could. The cream made an appearance again, and she curled her toes inward. It was an old trick taught to her by one of the upper-class students on how to keep herself distracted. Against the coldness of the touch and the awkwardness of another finger as it slowly pushed its way past her anus again though, matter how hard she tried, nothing she did seemed to make a difference as the throbbing returned.

Besides her, one of the other girls in the room started to sob as she begged for an orgasm that was never going to come. Holly didn’t bother to join in. The following week was not something she was looking forward to at all.