Anal Academy Pt. 03

Even as she slept Holly could not escape the weekend's relentless assault upon her body. Rest brought no respite. In her dreams her ass was filled with an endless stream of throbbing, pumping penises. She awoke abruptly with the vague echoes of a dream in which three men, who all looked like Robert Petat, were fucking her every available hole. As if the Anal Academy was not pushing her boundaries far enough, her subconscious mind was taking things even further. Perhaps, she thought, it was a proof point that she was indeed being trained, that her mind and body were ready for even more. Holly reached down into the space between her legs and found herself soaking wet. She felt violated and betrayed by her own body - but also not unhappy about it.

Holly sat up in bed and looked around - a small shoebox of a white windowless room, unadorned save for a single bed with white linens and a locked door, behind which the Anal Academy waited for her. Yesterday's conclusion came flooding back into her mind. Something off-book had transpired. She never returned to the Mess Hall for dinner with the other women. She wondered if they were all back at the Kennel or whether private accommodations were a routine part of the Night Two program. She wondered how far astray the typical agenda she had wandered. Would she see them again? Was the retreat over for her? Or had it hardly begun?

A knock at the door interrupted Holly's spiraling thoughts, and another in a long line of anonymous black-jumpsuited men walked in, setting down a tray of breakfast.

"I'm not hungry," Holly said. He cocked his head to one side and searched her with his eyes.

"You should still eat." He searched more. "It is good for you."

"I said I'm not hungry. I'm not eating." A devilish smile creased her lips. "Unless of course you're going to treat my mouth the way you guys treat my ass... and fuck my throat with a banana or something until I've swallowed it whole. Short of that I'm just going to pass on breakfast this morning, thank you very much."

The man nervously pawed at the side of the food tray with one foot.

"Well, uh, Ms. Witherspoon asked me to bring you to your, uh, morning assignment after breakfast. So if you don't want to eat, I guess you can just follow me."

Holly stood. "Ok then. Lead the way."

"Oh! I almost forgot." He reached into one pocket and pulled out a length of something Holy could not make out. He then reached up around her neck, and Holly heard the metallic clink of something being latched to her collar. "Welcome to Level Three," he said matter-of-factly as he pulled, and Holly lurched a step towards the door, drawn by the new tether.

It was an actual, literal leash. He had Holly on a leash like a dog.

Holly had assumed that if there were some directionality to the program, this implied ascension of levels that began when every woman was forced to orgasm on the first night, that it would be a more humanizing path. She figured it was like basic training, where everyone was broken down early on so that they could be rebuilt with progress. She had hoped that each subsequent day and session would bring her closer to the surface, closer to Frank - more human and less trained mongrel. But here she was, going down, not up, deeper into a well of animalistic degradation. The process of being treated like a stray dog in need of training was more literalized than ever. She was on a leash and being dragged down the hall one barely volitional step at a time.

With each step the protests and questions drained from Holly's mind. The program was having its intended effect. The more she was treated like an animal, the more Holly's mind and body responded with obedience. She fell in line and followed this man through turn after turn as they traced a path through the bowels of the Anal Academy to some unknown place where the day's fate awaited her.

He opened a door, led her into a room, and without saying a word exited and locked the door behind her. This room was far more sparce than The Pound. Like her room that night, it was unadorned, though larger. Instead of a bed in the corner there was a chair-like device in the middle, but nothing else. This implement was far more obvious than The Muzzle, with its opaque jigsaw configurations. This was a black leather reclined chair, with raised individual leg rests as well as arm rests splayed out to either side. It was very clear to Holly how she would sit and be strapped down here. What was less clear immediately was exactly what would enter which of her orifices in what ways.

Holly was uninterested in waiting around to be told what to do. The start to the path was very clear to her. She disrobed completely, leaving her jumpsuit and underwear piled in one corner. She walked over to the chair and sat down, leaning back and lifting each arm and leg into the spaces clearly designed for them.

She laid there for a moment staring up at the ceiling - legs spread, arms extended out. She heard the room's AC unit kick on, and a gentle breath of air brushed across her exposed pussy, sending a tingled chill up her spine.

Holly looked down and saw that there were retractable straps built into the arm and leg rests. Once again she figured, why wait? She bent down, and within a few minutes had learned how to deploy and sinch the bindings. First her left and then her right leg was secured in place. Then with her right arm she was able to tie her left down, but there was no way to finish herself off. She remained in place for nearly an hour, three-quarters of the way done, waiting for a staff member to complete her bindings.

Holly's gut burned with anticipation. She even felt a little anticipation leak out of her open pussy and drip down her ass. She was ready.

Eventually the door opened without a knock, and Holly heart the footsteps of two people enter the room behind her back. The clicking of heels indicated that one was Ms. Witherspoon, and Holly guessed the other was one of the black jump-suited henchmen. She briefly wondered if that was really the right term for them, henchmen? They probably carried some sort of vague, corporate-speak job title like Training Associate or Dildo Liaison.

"In all my years..." Ms. Witherspoon's voice picked up and trailed off. Her face peaked into Holly's field of view. "I've never seen the start of a session like it. You are an eager one, aren't you?"

Holly did not speak but merely nodded her head in assent.

"Good."

The man appeared also in front of Holly but quickly knelt down below her view and began fiddling with features hidden within the base of the chair. Ms. Witherspoon pushed her glasses up the bridge of her nose and eyed Holly from head to toe. She spotted the right arm, lying in place but unrestrained. She moved to the side and began applying those straps before assessing the other arm and both legs to ensure they were all tight enough. Holly felt the blood drain slightly from her feet as the leg restraints became tight to the point of nearly cutting off circulation to her outermost appendages.

"You are in for quite a treat today, as today is the day that The Whistle becomes your friend and guide. To this point it has been merely an acquaintance, but today you will really get to know one another."

Holly cocked an eyebrow quizzically. Ms. Witherspoon pulled a whistle from her pocket and blew it. The sharp, harsh, but not unpleasant sound filled the room, and Holly winced slightly. When her eyes returned with Ms. Witherspoon's face, Holly found her eyes trained intently between her legs.

"Excellent! Your response is already quite advanced for this stage. I am pleasantly surprised by your progress." Without speaking, Holly again looked at her curiously. Ms. Witherspoon smiled as she decided to spill the beans on what this all meant.

"You see we have come a long way already in training your body as well as your conscious mind to meet the needs of your husband. Today we work more on your unconscious mind. So far you have been, and today you will continue to be, trained to associate the sound of this whistle with the onset of pleasure. Much like Pavlov's dogs salivating at the sound of a bell, the stimulus of this whistle has made your pussy moisten. Within seconds the change was remarkable just now. You'll remember that this whistle has been a small part of all prior sessions, but now we will feature it. In this session, which we simply call The Whistle, you will be made to orgasm. Your master here will place several electrodes over your body and monitor your vital signs and minute electrical impulses within your body that indicate climax. When you blow your load, as it were, he will blow the whistle, and in doing so will further associate this sound with the heights of pleasure in your mind. In this way, your training will be nearly complete."

Holly was astounded. This was going to be a walk in the park compared to the day before - no stretching beyond her capacity, no living at the razors edge between pain and pleasure. All she would have to do is just lay back and cum and let her subconscious mind do all the work of association. This sounded great!

"I see that you are pleased by the arrangement. Don't get too comfortable though. You should know better than that by now. I will leave the two of you to it then, but I will be watching from the Control Room, and I will provide coaching over the speakers as necessary."

The heels clicked their way out of the room, and Ms. Witherspoon was gone. The master by this point had reappeared from his work below and held a large syringe.

"I try to be more efficient with the lubrication process than most, so I'm just going to put this little guy up your backside and inject a bunch of lube from the inside." True to his word, Holly immediately felt brief pressure at her anus before a river of lube filled her and some of the overflow trickled out. The master used his hands to smear it around the exterior of her orifice, coating everything to his satisfaction. "See? Easy right?"

Holly nodded.

"Now, step two. I think I've got just the right dildo for you." He reached below. In his prior preparations he had affixed the chosen inanimate cock to some rigging inherent to the chair's purpose. He pulled out an arching metallic rod that slid out, with the dildo on the end. The rod extended up and back until the dildo was pointing right at Holly's ass. "This way it can't slide out when you cum," he added helpfully. The rod would hold the dildo firmly in place.

The next thing Holly knew, her master was advancing the dildo through the breach of her anus and into the depths within. As he did so he blew the whistle gently, and Holly gasped as she found new enjoyment in this penetration. A ripple of anticipation cascaded into her pussy, and she could feel her clit swelling in real time. Holly began rocking her hips and grinding into the dildo, searching for friction and more fullness.

"Oh don't worry. We are going to get you there soon. Just let me get everything else set up." With that he brought out a small side table and began setting up his supplies. He attached electrodes to various places on Holly's body and attached them via wires to a monitor. Numbers and bouncing wavy lines filled the screen, which were meaningful to the master but incomprehensible to Holly. At the very least he seemed quite pleased with their starting point and grunted his acknowledgement. He put a lanyard with his whistle around his neck, stuck the whistle in one corner of his mouth and murmured out the other side, "OK, let's begin."

From his table the master brought forth a small vibrator and put the tip to rest against Holly's clit. She nearly squealed in excitement. He mashed the 'on' button and away they went together. Holly's loins were quickly filled with pleasant ripples. She paid particular attention to how the vibrations not only stimulated her clit generously but also resonated through her pelvic bones and helped her feel the anal dildo rattling around within her ass even more fully.

This is it, she thought. This is why I'm here. I'm experiencing unambiguous pleasure with something in my ass. I am trained up and ready for Frank.

She was already so filled with sexual anticipation, between the time waiting in the room, the feeling of being bound to the table, the brusque manner of Ms. Witherspoon, and that seemingly magic whistle. She knew it wouldn't take long with a well-placed vibrator coaxing her along. Rings of pleasure encircled her, and Holly felt the familiar precursor tremors to an oncoming orgasm. She closed her eyes and opened her mouth into a gaping O. Her breathing, slow at first, gradually picked up pace until she was panting.

"Oh...... Oh..... Oh.... Oh... Oh! I'm getting close. Is that OK? Can I cum now? Am I allowed to cum? Do I need to let you know?" Holly wasn't sure how this was supposed to work. Her master responded.

"Just let it rip. You don't need to tell me anything, unless that's what does it for you or something. I can see it all on the monitors. I can see how close you are. But yeah, go ahead and bring it. Go ahead and cum."

Holly shook and gasped and the master blew his whistle and continued the sound throughout the duration of Holly's orgasm. The restraints quelled the bucking of her body, and she settled into a relaxed puddle of herself as her climax subsided.

But the master never relaxed. The vibrator did not subside.

"I'm good now; I'm good." She panted. "It's over. You can stop."

He cocked an eyebrow, genuinely perplexed.

"Oh. There must have been some miscommunication. We are just getting started." Stoic, he held the vibrator in place, and Holly was pained by her post-orgasm sensitivity. She squirmed and grimaced beneath the unrelenting stimulation. It felt like acid poured over a wound.

Ms. Witherspoon's voice came over the room's speakers. "Holly dear, you might want to disabuse yourself of the notion that you have any control over when exactly this experience ends. Things will go easier if you release any protests from your mind and your body and accept that you are a blank slate whose only purpose here today is to cum." Holly nodded her assent, gritted her teeth, and closed her eyes as she tried not to think too much about her sensitive clit being mauled by a vibrator she no longer wanted.

Mercifully her master removed the tip of the vibrator from over her clit and began moving it further afield - slowly all around her vagina. It traced a rim around her outer margins before its course slowly encircled tighter and tighter before burying itself within her depths. Holly's sensitivity began creeping once more toward outright pleasure. She relished the feeling of the apparatus vibrating within her, especially as it slid across from the dildo in her ass, a thin pane of tissue separating them and capturing the rapture of both.

When the vibrator emerged outside and found its way to Holly's clit once more, she was ready for it. A moan escaped her lips, followed by a long, soft exhale of breath. The master was more dynamic with his prodding this time, circling the clit, providing pressure from above, pressure from below, and flicking it gently as he moved it up and down the length of her pleasure nub.

The master turned his face to the ceiling and spoke as if to the speakers that Ms. Witherspoon's voice sprang from. "We are back to a six and making good progress now, Ms. W." He looked back down and turned his attention to the work at hand. He adjusted the toy's settings, and it now vibrated faster, harder. He held it in place with his right hand, and with his left he pulled back on the skin and lips of her outer labia. The fingers of this hand then reached further down and pulled back at the hood of flesh covering her clit and exposed her button more nakedly to the vibrator.

This change sent Holly's body into upheaval. She had now fully transitioned across the spectrum of orgasm to pain to acceptance to outright pleasure again. The master stimulated her exposed raw nerves without mercy, and Holly welcomed the assault. She felt her entire pelvis rattling as one - the vibrator, her clit, the dildo in her ass, and the very marrow of her bones seethed in unison. Her body was a symphony playing in time and conducted by her master's well-placed baton. Holly sang out and added her voice to the cacophony.

"Oooooooohhhhh. Oh! Ooooooooo. Ah, ah, ah, ah." Her voice wavered and faltered, as it too rattled with the vibrations subsuming her entire being. Out the corner of her eyes she witnessed the master check his screen and bring the whistle to his lips in response. She must be close.

"Harder!" She called out. "Push it in harder. Act like that's the eraser on the tip of a pencil and you've made a mistake. You need to erase my clit." Her master responded, digging the tip of the vibrator forcefully into her. She felt the appropriate response within her. "That's it. Yes. Erase me. Erase me off the fucking planet." The pressure came even harder now, and there it was. He had pushed so hard that the dam was breaking. A flood of energy surged from her insides, and Holly heard him blow the whistle as she screamed out, "I'm comiiiiiiiiiiiiiing...!!!" He seemingly held the whistle's note for an eternity as wave after wave of orgasm rippled across Holly's body. She began to wonder if it would ever end, if she would be forever trapped within a sarcophagus of her own crippling cum, but as the whistle fell silent the sensations faded, and she returned to a sense of normalcy.

He stopped the vibrator and turned his back to Holly as her panting breaths slowed and she closed her eyes, relishing the post-rapture bliss. She heard a click as the master turned back towards her holding a stopwatch and said, "Five minutes. You have five minutes to recover, and we begin again." He then turned back to the table with his monitor and began preparing for whatever would come next.

Holly wondered how long this would persist. How many orgasms would she have? Could she have? She tried to remember the most times she had ever cum in a day. Maybe two? And here she was at two within the past ten minutes or so. For a moment she wished she was back at The Pound, having her ass stretched by inhumanly large dildos. At least she knew she could take that punishment. She wasn't sure how much more of today's activity she could take without her soul leaving her body.

"Chop, chop. Back to work now."

"Five minutes already?" she pleaded.

"Yes, and I hope it was a restorative five minutes because I will ask much more from you now." He held up a new vibrator. It was a 'magic wand'-style piece. Holly had never used one, although she had seen them used in pornography and had seen them advertised in online sex stores. She had always been afraid of them - that one would be too much for her. For a lifetime she had been contented to get off with small, inexpensive, simple vibrators, and she wondered if this would live up to the hype.

She glanced from the wand down between her legs. Even while strapped in place with limited mobility, Holly could see how grotesquely swollen she was in response to all the stimulation. Her clit stood out above the fray, indecently engorged. Holly wanted her body to signal a retreat and retract within herself to protect her. Instead, she was unimaginably exposed, her swollen clit making itself a larger, more docile target. While her mind feared, her body practically called out, "Here I am. Come and fuck me!"

Her master placed the vibrator's padded head against her open orifice without turning it on. She detected the cool kiss of silicone against her hot, angry loins. Somehow she felt ready already. "Let's begin," Holly said aloud. Wordlessly the master activated the vibrator, and her body buzzed again.

Holly became more welcoming of this assault. She accepted the unrelenting nature of today's activities and allowed herself to receive pleasure rather than be overcome by her body's overstimulation. She breathed out, long and completely, until she felt empty. She held her breath there, dwelling on the sensation of hollowness and the desire to fill herself with air. As she inhaled, Holly imagined herself filling that hollow space with the capacity for more - more pleasure, more climax, more vibrations, more dick in her ass, more of everything.