Anal Academy Pt. 02

Holly awoke, disoriented, uncertain of time or place. She quickly remembered that in all likelihood it was Saturday morning in the Anal Academy, but she still was not sure. She sat up in her bed in her cage but could not see beyond the bars. A sheet of fabric was draped across the top and covered all sides, allowing a small amount of muted light to penetrate her cell. She could be anywhere, any time. She could have been drugged, transported; it could be a week later. Her brain was running circles around ever morbid possibility.

Then Holly heard whispers, the other women. The echoing sound quality told her they remained in the Kennel.

"SHHHHH!" one hissed.

"They hear everything," another.

Silence fell again, with the exception of some muffled scurrying. As Holly oriented herself to her new reality, two additional changes became obvious. First, a straw picnic basket sat within the entrance of her enclosure, a homey corner of red and white checkerboard tablecloth peeking out from beneath the lid.

Second, a collar encircled Holly's neck. She reached up and touched it instinctively, before realizing she should not have, but fortunately this new wearable did not electrically shock her when handled. She felt around its margins: smooth, thick, immalleable metal - though not uncomfortable due to padding that protected her neck. The outer rim was complex, knobs, hooks, places for attachments, and the locking device, but she could not discern the exact purpose of the specific segments and feared for the possibilities.

Whatever it would become, the collar was not now holding her in place, and Holly moved freely as she made her way to the picnic basket. As she stood, she saw that not only had she been collared in the night but also had been dressed in a blue jumpsuit. She approached the basket, a comically incongruent artifact of hospitality at the Anal Academy, and found a note.

Holly,

Here you will find two necessary ingredients for success today. The first: breakfast. We bake the scones ourselves on site! Also, you will discover a bottle of moisturizing oil. Apply a very (very) generous amount on your anus and the surrounding skin. This will prepare you physically for the rigors of today.

Cheers,

Robert Petat

First things first, Holly thought. She emptied half the bottle of oil into the cupped palm of her hand and reached up and under her loins, slathering the oil throughout her ass crack. Ordinarily she would have felt self-conscious about an act like this, but after being forcibly vibrated to orgasm by an anal probe in a room of complete strangers begging her to cum, she had lost her capacity for modesty. With her other hand Holly fed herself scones as she continued applying the rest of the oil. It was warm and strangely soothing.

Holly lay, content, for some time until a clattering of sounds filled the room. A stubborn metallic door was being loudly ratcheted open, followed a rhythmic beeping that indicated construction equipment might be reversing into the room.

Hydraulic whooshes, metallic clanks, and then the surprised scream of a woman to Holly's left. The engine's rumble gradually receded into nothing, and the ensuing silence seemed permanent. Holly wondered if the interruption had been some hallucination until the engine was manifest in the room once again. The groaning of steel came again from Holly's left, but this time it was the cage immediately next to hers, now close enough for Holly to understand what was happening. Some vehicle was picking up their cages and moving them to another location.

Holly was next.

She sat patiently, Zen-like. The engine gave way to silence, gave way to infinitely more silence, gave way to the return of Holly's fate. The rumble came closer, like hot breath on the back of her neck. Holly saw two large blades extend beneath her feet under the floor. It was a forklift.

Hoisted a couple feet above the ground, Holly's cage, and Holly within it, were transported. Where? Somewhere. She could see the tiled floor gliding past underfoot, but all other views were obscured by the drape surrounding her. Eventually she was laid to rest, and she waited. Seconds turned to minutes, which piled up until Holly was not sure how long it had been since she'd moved.

A door opened, and Holly heard the clicking of high heeled shoes walking closer to her. It had to be Ms. Witherspoon, the only woman Holly had seen here other than the inmates.

"I don't usually do this, you know." It was indeed Ms. Witherspoon's voice. She paused but continued walking, circling Holly's covered cage like a shark. "I don't usually get involved in the nitty gritty of these sessions. With expertise like mine, the retreat is best served when I can oversee and guide multiple sessions. But last night you were quite a hold-out. I wasn't sure you'd ever get there. I was worried you were on the precipice of flunking out on Day 1. So I will be personally overseeing your session today to ensure that we remain on track."

The sheet covering Holly's cage was pulled away. She saw Ms. Witherspoon standing there in the flesh holding the sheet. Behind her stood the strangest wall décor Holly had ever seen.

"Welcome to The Pound. This is where we will be holding your morning session. We find that each of our guests requires an individually tailored itinerary to flourish in our program. The first day is fairly set and standardized, but from here out we will be selecting several half-day experiences designed for your particular needs. The Pound is usually a room for guests at more advanced parts of their journeys, but I believe that after what I witnessed yesterday you are in need of the tools here."

Most of the room was again tiled, sterile, but the background behind Ms. Witherspoon was different. It was the most contrasting accent wall imaginable and brought to mind, for Holly, a trophy wall in a massive hunting lodge. Only instead of the taxidermied heads of a hundred animals covering every square foot of the wall, it was dildos of every convenable shape and size. The longer, heavier ones sagged downwards at the tip, drawn by the forces of gravity, and for Holly the effect was one of a hundred fake cocks leering at her - leaning downwards to get a better look at their prey. The metaphor of the hunting lodge reversed in Holly's mind, and it was as if the animals were alive, crawling out of their plaques and threatening to fuck her in the ass. Running along the top of the wall were the letters A through Z, corresponding to columns of dicks beneath each. On the sides, rows were numbered 1 through 5.

It was a fucked up excel spreadsheet.

At the base of the wall in the middle was a black bench with a series of attachments and straps with purposes opaque to Holly. While she attempted to divine its purpose, Ms. Witherspoon held up her tablet, pressed a few items on the screen, and the door to Holly's cage unlatched and swung open. Before she could even gesture towards the door, Holly felt a mild but startling electric shock encircle her neck.

She jumped back and screamed. It had come from the collar.

"Before you walk out that door, you must know that I control you completely, despite the freedom of leaving your cage. I can shock you like that, and worse, any time I like. I will not do so as long as you follow my instructions completely, quickly, and without discussion. Am I understood?"

"Yes."

"Good. As I said before, this is The Pound." She gestured towards the wall. "You will begin by walking over here and standing beside The Muzzle." She pointed to the black bench in the center. Holly rapidly did as she was told, nearly jogging to the bench at the base of the wall.

"What we have here is not a literal muzzle for your mouth. I actually want nothing more than to hear you loudly throughout the experience. That is part of the process. Instead it will muzzle unwanted reactions from your body, like the desire to pull away, run off, or move in any way.

"Disrobe completely and lie on your back with your head resting here." She patted the end of The Muzzle furthest from the wall.

Holly did as she was told. She felt the process taking hold of her. Questions left her mind. The desire to run escaped her feet. With each instruction, each shock, each new implement of domination, Ms. Witherspoon was gradually filling her with obedience. Holly felt neither positively nor negatively about this new reality; she simply accepted it. She unzipped the jumpsuit, which had been placed upon her unconsciously in the night, and let it fall to the floor, a puddle of cloth around her feet. She was now completely nude; her underwear had been removed during the jumpsuit application.

Holly approached The Muzzle, trying to ignore the various appendages and block from her thoughts hypotheses about what purposes they might serve. The bench was only three-quarter length, so when she set her back and head upon it as instructed, her legs dangled awkwardly off the other end.

Holly closed her eyes. She heard the clicking of Ms. Witherspoon's heels on the floor. She felt The Muzzle being manipulated beneath her, parts pulled around, assembled, reassembled. It sounded like a piece of Ikea furniture being assembled on fast forward.

At no point had she been told to close her eyes, but Holly held them shut regardless. It made no difference whether she witnessed the visual preview of what was to come. It was happening all the same, and Holly preferred to wait and take it as it came, literally. She felt her left leg lifted in the air and come to rest on a padded suspension above her. She heard leather pulled and buckled. The leg was strapped down, comfortable, but now immobile. The same sequence repeated for the right leg. The freedoms of Holly's arms were taken next. Each raised to the side and over her head, buckled down with multiple straps in the frozen pose of a precocious girl raising both hands to ask a question in class. Finally the locking mechanism on the back of her collar was married to a fixture within the Muzzle, and she was locked in place.

No questions escaped her mouth because she knew that no answers would be forthcoming.

For something called "The Muzzle" the ergonomics were shockingly comfortable. She couldn't move, much less squirm slightly, but Holly's body somehow felt at home and at ease in her restricted state. She opened her eyes and noted the dramatic contrast of her pale nude flesh against the backdrop of the black leather Muzzle holding her in place. Her legs were up in the air, shins perpendicular to the floor, hips bent inward slightly, like they were in stirrups at a steampunk gynecologist's office.

Ms. Witherspoon walked to the spot between Holly's captive legs, looked down, and nodded approvingly.

"This will do well."

She released a small leaflet at the end of the bench. While Holly's back remained supported, the end of her ass hung slightly over the new ledge, providing greater access to her anus. Wordlessly Ms. Witherspoon placed a latex glove over her right hand and pulled a bottle of oil from a shelf hidden beneath Holly. She provided a generous serving to her gloved palm and, without warning, began applying across every square inch of Holly's loins. She coated the skin, massaging it gently but firmly. Then, with a second palm-full, Ms. Witherspoon's application paid closer attention to Holly's puckered back door. Brusque fingertips encircled her most sensitive aperture. It felt foreign at first but gradually Holly came to regard the stimulus as vaguely pleasant, if unknown - like the first time you hear the opening notes of a good song and aren't sure where it is headed.

The lubed fingers began probing more, applying pressure at the entrance, penetrating to the first knuckle. They rotated, took turns, and more oil was supplied. Holly knew her very insides were being lubricated, preparing her for what was next. Surely this session would not stop at Ms. Witherspoon finger-fucking her ass. The wall of leering disembodied cocks had to be there for a reason. The fingers penetrated deeper, pushing the oil as far as they could manage. Holly released a small gasp as Ms. Witherspoon's thickest knuckle on her middle finger came to rest within the breach of her tight inner sphincter. There was a sensation of emerging fullness that she liked.

"That's enough now." Ms. Witherspoon withdrew her hand and removed the glove. She pulled out a whistle and blew. The sound was the same as Holly had heard the prior night. She pulled out a tablet and pushed several buttons on the screen, shielded from Holly. "Let's start with A3," she said, more to herself than Holly. "That's a nice one."

Ms. Witherspoon departed the space between Holly's legs and walked into the recesses of the room outside Holly's frame of vision. She watched as the unobstructed wall in front of her began to shift and move. The dildo at the far-left side of The Pound in the middle row shifted down, between rows 4 and 5, and slowly migrated into the center of the room, from left to right between the rows, accompanied by a buzzing hum and the occasional metallic catches that hinted at a vast machine behind the wall, controlling the movements of any selected dildo.

It's a vending machine, Holly thought. Columns and rows, numbers and letters. But instead of Snickers and Sun Chips, Ms. Witherspoon could order up a fake dick of any conceivable configuration to train Holly's ass.

Mr. A3 shifted downward once again until it was perfectly aligned with Holly's exposed and lubricated ass. The ground rumbled under Holly as the Muzzle slid forward on some invisible track, bringing the cock head to rest right against her anus. Ms. Witherspoon blew the whistle again.

"No need for any further preamble. It should be fairly clear what the objective is here. Last night we began training your mind. Today we begin training your body. You will be prodded, stretched, molded like a piece of clay. You will be made ready to accept progressively more. Should you feel the need to scream, we welcome it. We find that it releases endorphins that aid in the dilation process."

A mechanical whirring indicated that A3 had been activated, and it slowly advanced, applying gradual pressure upon Holly. She instinctively clinched up, recoiled into herself, but with no way to actually withdraw her body the pressure simply built. Holly took a slow deep breath, in and out. As she released, she relaxed, allowing the intruder within. The dildo sank deeper, and she breathed deeper, pursing her lips as she exhaled vast volumes. Fully within, the advancement ceased. Though still, Holly felt herself occupied. She had not paid close attention to the specifics of A3, too overwhelmed taking in the entirety of The Pound to assess the exact caliber of one object among many. Now that it was within her, Holly thanked Ms. Witherspoon silently within her thoughts. It was generously none too thick, a pleasant starting point. Holly had been worried the training process would be painful, like being split at the seams, but this sensation was a comfortable fullness.

Like a steam engine slowly building up momentum, the piston onto which the dildo was mounted gradually begin withdrawing and thrusting, the strokes shallow and deliberate at first, then gaining pace and depth. Holly focused on her breathing as she accepted a range of new sensations into her world. Her eyes bulged and her breath quickened as she realized that those sensations involved new flavors of pleasure. It wasn't exactly like sex as she had known it, wasn't like fucking herself with a dildo, which she'd done plenty before, but it was pleasant and good nonetheless, and Holly submitted to reluctant enjoyment.

A series of beeps came from behind Holly, a new selection on the tablet. This dildo slowed and withdrew, retreating to its prior spot on the wall. A3 sat quietly now, luridly contrasted against its peers as the only object coated in moisture. From Holly's right a new dildo began making its way to her. She paid closer attention this time, noting an uptick in girth and length. It came to rest between Holly's legs, and Ms. Witherspoon reappeared with glove and lube in hand. She manually applied some to the new appendage. If she found any humor or pleasure in the act of jerking off a rubber dick to lube it up for a captive's barely-semi-willing ass, she did not make it known.

With the press of a button the new cock advanced forcefully, unyielding. Caught by surprise, Holly held a breath rather than releasing one peacefully. Her ass did not protest. It acquiesced with aplomb, but Holly could not imagine taking much more than this. She felt the boundaries of her cavity fully embrace this member as it filled her absolute margins. Rather than pausing at any point, this dildo set instantly into an in-and-out cadence, gliding smoothly but forcefully.

Holly parsed her feelings. She asked her body, is this pleasure? Do I like this? She sank deep within herself. She ceased to inhabit the room and instead inhabited only the sensations thrust upon her. Yes, she thought. I do think I like this. This acknowledgement seemed to loosen her, relax every muscle in her body, including those under increasing strain. She decided to not only accept any one of this Great Wall of Dildos but to willingly invite them in. Fuck me, she thought. Fill me. Open me, pound me, loosen me, expose me, use me, make me.

The sounds of the dildo within her became wetter. There was a sloshing quality. Holly realized with delight that she was becoming so turned on that her pussy juices had spilled out and ran down into her ass. She was self-lubricating for a machine that was fucking her ass, and this knowledge made her moan with relish.

The thrusting slowed and stopped as Ms. Witherspoon beeped away at the tablet out of view, a new selection on the horizon. Holly released a long sign and closed her eyes, awaiting her next gentleman caller. She listened to the mechanical creaks and moans as The Pound shifted itself to present a new implement for her ass. Eventually she detected a nudge followed by pressure, followed by more pressure.

"Oh!" She called out.

"FUCK!" She yelled.

"WHAT THE FUCK?!" She screamed full throated. The pressure was unrelenting and only increasing. Holly wished now that she had kept her eyes open and watched for the size of whatever this was, because whatever it was - was huge.

"Is that it? Is it in?"

No. It advanced further, agonizingly slowly. Holly felt no longer filled so much as she felt expanded to an inhuman degree. It built and built until eventually the head of whatever monstrous dildo was attacking her progressed beyond the tightest point of its journey and found its way into the depths of her ass. Holly experienced a brief reprieve, even if the girth of the shaft below the head was still beyond her comprehension.

Ms. Witherspoon appeared out the corner of her squinted eyes and began pouring oil all across the area - over the exposed portions of the dildo, down Holly's pubis, cascading all around her swollen, gaping hole.

"You were doing so well I thought we might go for broke now," a malevolent glint in her eye. "Usually we progress through a series of five widths leading up to this one, which provides maximal stretch training. But I felt you were ready early," a wink. Holly gave no response but merely whimpered. She closed her eyes, returning to slow, deep breathing. Gradually the dildo initiated its pattern of withdrawing and pushing, so slow that it matched the pace of Holly's breathing. As she inhaled, she was filled, not only by air but by The Pound. She paused as it reached its point of furthest penetration. She released her breath as the device pulled back, as least temporarily.

Seconds turned to minutes, and Holly found rapturous peace repeating the pattern. With each breath discomfort turned to acceptance turned to - pleasure? She thought it impossible to be pushed this far and find, beyond the horizon of her limits, gratification. But there it was.