Anal Academy Pt. 01

Holly sat on her hands in the passenger seat. She had to shove her hands under her ass to hide them from her husband, the driver. They were shaking - trembling, she thought. She was nervous. God, she was nervous. They drove along a bumpy back highway, and she felt the jiggle of her ass as she was lifted off her seat slightly with each bump. Bump, bump..... bump..... bump, bump, bump. This probably wasn't the best place for her hands. It made her think about her ass, and she was trying to keep her mind off her own ass. Ass, ass, ass, she thought. Think about anything but your ass.

A month ago, Holly had agreed to this trip on a whim. She and her husband, Frank, had been having trouble in the bedroom. For years she had been growing progressively less interested in their transgressions between the sheets, but she kept at it because it kept him happy. It never seemed to bother him; he didn't notice that she was never wet spontaneously and needed a squirt of lube to get things started. But something registered, even if only subconsciously. Frank's cock was failing. It was slower to arouse, softer, and sometimes could not be made to finish. Her struggles mentally and his struggles physically had congealed into a stew of discontent.

An idea occurred to Holly; let's try anal! The thought stirred Frank and revived his cock right back to its old self. That night he was as stiff as he'd been in a decade, but it came with a downside. Frank was a well-endowed man, a very well-endowed man. And his endowment simply would not fit within Holly's vault. She tried every relaxation and deep breathing technique she could conjure in the moment. They exhausted the remainder of their lube supply in the endeavor, but Holly's puckered back door remained shut, unyielding to his girth no matter how game she felt.

Despite the failure, the excitement of trying something new resonated with them both. Holly left that evening with a renewed sense of purpose - find a way to fit that big dick up her ass and jump start her sex life with her husband. She combed the internet, magazines, and books looking for tips on how to make anal sex work for them. She tried a few things with a frank-sized dildo she kept in the closet, but nothing worked. Her ass had a mind of its own, and that mind thought "no."

On the verge of giving up - maybe just on the idea of anal, but also possibly on sex in general and her marriage writ large - Holly came across a link for something called Anal Academy. It promised to help reluctant women not only engage in anal sex for the first time but also derive unexpected pleasure from the act. Her session was structured as a weekend retreat. Participants would arrive on Friday, engage in workshops and seminars throughout, and leave on Monday, apparently fully prepared to take on their partners in new and spectacular ways. The dozens of testimonials were glowing. The retreat's owner was singled out repeatedly for praise. Holly toggled over to his bio page on the site.

"Robert Petat is the owner and operator of Anal Academy. He has helped hundreds of women like you overcome their fears and learn to enjoy anal pleasure. Prior to founding the Academy, Robert was a renowned veterinarian and animal trainer. Our methodology combines his prior training expertise with a deep appreciation for human psychology. Satisfaction guaranteed!"

It all sounded unorthodox, but at this point Holly thought it might be worth a try. She convinced Frank to let her go, and a month later they were bumping along back highways on a three-hour drive from their home. The location sure was remote, but Holly figured residents and businesses in more populated areas probably wouldn't stand for something called Anal Academy operating down the street.

She glanced over at Frank. A frown hung on his face. Partners were not allowed to attend the retreat. It was for the women only; "to ensure the utmost privacy and relaxed atmosphere," the website read. Frank thought that was weird and had been having second thoughts about all of this for the past week. Holly echoed his concerns but wanted to proceed any way. Maybe it was not quite as dramatic as all this, but she told herself that the future of her marriage depended on learning to take it up the ass, so she put on a happy face and sat on her shaking hands so that Frank could not read into her uncertainty.

The car slowed. They were pulling up to a gate. A speaker box to the left blared out, "Can I help you?"

"Uh, yeah. I'm here to drop off my wife Holly."

"Yes, we have you on the list. Enter and pull out in the front." A high-pitched beep resounded and the gates opened before them. Holly chuckled aloud when she realized that each side of the gate was rounded and meant to look like left and right butt cheeks, and the cheeks were opening up to let them through the widening crack between. Her laughter stopped when she looked past the gates and saw that the perimeter walls of this retreat complex were built of stone walls topped by thick coils of barbed wire. What are they trying to keep out, she wondered.

They drove up a long gravel driveway until reaching the front of a building that looked like a hotel entrance. A roundabout encircled a fountain with a statue at its center, and attendants emerged as they pulled to a stop under an awning. Frank and Holly stepped out from the car.

"Please, we will attend to the bags for you. If you will, follow me and I will take you to your check in with Mr. Petat." Holly and Frank followed the attendant obediently. They were ushered around a corner, down a hallway, and into an office across the desk from a portly, mustached man. Mr. Petat looked less like Holly's idea of a sex therapist and more like the unholy amalgamation of William Howard Taft and a walrus. She remembered his background in veterinary medicine and wondered what animals he had worked with.

"Greetings! Greetings!" He bellowed. "You must be Holly and Frank."

"Yes."

"That's us."

"Welcome to our little retreat in the countryside. Before we get started with our program and before you go your separate ways, I always like to avail myself to our guests and answer any outstanding questions you may still have. These are unusual circumstances and an unusual place for most people, and I want you both relaxed and comfortable with the plan." He beamed with a gentle happiness and an innate pride in his work. Holly felt instantly at ease.

"Well, I think I understand the concept of the program, but could you provide a few more details? Is there an itinerary?" Holly asked. Petat placed his hands around his belly and chuckled deeply, smiling.

"A good question. A great question! But if I gave you the answer you wanted, the itinerary itself would be less effective. You see, we find that part of the skill of learning to enjoy new things is learning to enjoy the unexpected. If you know what to expect, your enjoyment will be diminished, and we are all about enjoyment here!" Another belly laugh followed.

His answer puzzled Holly, and a silence settled in the room briefly.

Frank stepped in. "I, uh, understand you used to be a vet. What brought you to this line of work?"

"Oh, I wouldn't quite say that. A veterinarian? Not exactly, not exactly, no matter what the marketing materials say. I ran a large kennel, rescued stray dogs, and trained dogs. I trained them for the movies even! I'd wager that just about any dog you saw on your TV screen in the late 90's was probably trained by me. I built a very successful operation and ended up selling my share to my partner. Needed a new challenge, I did. And I wanted to follow my real interests, sex. Love it, love everything about it. And I wanted to share that love with people who needed some help along the way. So I used my earnings to build this place to help folks like you find more pleasure in their own bodies. Even with a figure like mine," he rubbed his protuberant belly for comedic effect, "there is still pleasure to be found. And the ass, oh yes the ass, is the final frontier, often the undiscovered country for good folks like yourselves who make their way to me. Tell me now, what brings you here for this weekend of discovery?"

Holly looked down at her feet briefly, losing her nerve. She looked up and met Mr. Petat's eyes. His face was so inviting and encouraging. Holly began to tell their story, slowly at first, and then excitedly. It felt good to talk about it.

When she finished he responded, "That's good, that's good. You will do well here. This is the right place for you. Mr. Frank, I feel confident that when you return on Monday you will find a very changed Holly waiting for you. Now if there are no other questions, I have a couple of next steps for us." He reached into a desk drawer and pulled out a slender object that Holly did not immediately recognize.

"This, my dear," he said, reaching the object across the desk for Holly, "is a butt plug." He dropped it into her open hands and paused for dramatic effect. "Your itinerary begins now. Through that door behind you, you will find a restroom with everything you need. I want you to apply a healthy amount of lubricant to that little guy, insert it up your ass, and come back in here where you can kiss you hubby goodbye, and we'll send him on his merry way."

Holly turned and searched Frank's face, a mask of frozen surprise spread across hers. He nodded his head and gave an encouraging flick of the eyes towards the bathroom door, prompting her to get up and follow directions. As she walked, Holly felt numb from the abruptness of this transition. Sure, she knew there would be physical aspects to this weekend, but she thought everything would ease in gently with some educational workshops. She had not imagined that step one would be putting something in her ass. She barely felt her feet touch the floor, barely registered the sensation of the doorknob in her hand, as she exited the room as instructed.

Once alone, her mood shifted. She began to feel more pleasantly naughty. Holly lifted up her skirt and pulled her panties down and off. She found the lube, applied a generous amount to the plug, and in doing so began to study the object. It was black, sleek, simple, but something in her gut told her there was more than meets the eye. A complexity lurked there; she knew it. It had a generous base, but the part that needed to go inside her was petite, about the width of her pinky finger. She was relieved, confident it would fit, unlike her husband. Holly reached back behind herself, found the appropriate entrance with the tip of plug, and gently drove it within her.

Not so bad, she thought. Easy enough. Holly was proud of herself. She'd taken the first step.

She wiped the lube off her hand with her panties and grasped them within a balled fist as she walked back into the room. She leaned over Frank to give him a peck on the cheek and stealthily brought her hand into his lap and shoved her used panties into his pocket. Holly winked as she withdrew her head and sat back in her seat. Pleasantly naughty indeed!

"Well, we are off to a roaring start!" Petat's eyes flashed. "Frank, you may leave the way you came, out that door if you please. We will see you back here at 10 am on Monday, when you'll be able to pick up your beloved and get on with your lives together. But for now, please go!"

Frank stood up hesitantly and left with a meek wave.

"Now, Holly." He gestured to a door on the opposite side of the room. "If you will please come with me, I have someone I would like to introduce you to."

On the other side of the door was a woman, seated opposite another desk. She was thin, bookish and severe looking, middle-aged. She radiated a sort of "exasperated librarian" energy with wire framed glasses and her hair pulled into the tightest bun imaginable.

"This is Ms. Witherspoon. She is our lead therapist here at the retreat. She will be conducting your intake examination, and then she will escort you to dinner where you can meet the rest of your cohort for the weekend. Now, if you will excuse me," and he left the way he had come.

Ms. Witherspoon gestured to the seat opposite her, and Holly sat.

"I have read your file. I understand your story and why you are here, but what I want to know is how motivated are you? How much do you want this?"

"Excuse me?"

"Tell me. On a scale from one to ten, ten being the most determined to make this work, how motivated are you?"

Holly thought for a moment, a bit taken aback by this abrupt line of questioning. "Well. I suppose a nine. Maybe a nine and a half." She decided to attempt a joke. "I mean, we're talking about my husband's cock, right?!"

What she received instead of an appreciative laugh was the coldest icy stare imaginable. Ms. Witherspoon was not amused.

"Are you motivated or not?"

"In all seriousness, ma'am, I am a nine. I need this weekend. I need it for my marriage."

A curt smile creased the corners of the therapist's lips. "Very well then. Let us begin." Ms. Witherspoon conducted a wide-ranging interview covering Holly's entire sexual history and a brief overview of her relationship with Frank. At one point, mid-sentence, she brought out a tablet that had been concealed in a desk drawer. Without breaking eye contact or losing the thread of their conversation, she pulled up some app and began toggling through buttons on its interface. Holly glanced down at the desk surface but couldn't make out what she was up to because of the glare and her upside-down view. The conversation continued unabated.

Holly thought she felt something strange. She shifted in her seat uncomfortably. Something had changed between her legs. She subtly rocked back and forth in her seat tryng to discern the difference. She had nearly forgotten about the butt plug she'd inserted earlier. Its gentle, slender curvature was almost invisible to her body. But now she was registering its presence. It felt as if the plug was occupying more space, filling her more fully, like it had grown within her. She flinched at the sensation, and Ms. Witherspoon caught the grimace that rippled across her face.

"Is something the matter," she asked innocently.

"I..." Holly debated telling the truth. She didn't want to admit she was off to a bad start with the treatment program. "I - uh. I think I need to use the little girl's room."

"Right through that door." Ms. Witherspoon pointed towards a door and brought her attention fully to the tablet in front of her. As Holly got up and walked something indeed felt very different. It was like someone had snuck into the room and changed out her beginner's level butt plug for one three sizes bigger without her noticing until now. She spread her feet out and opened up the width of her gait as she walked to accommodate for the sensation.

Once in the bathroom, Holly found a floor-length mirror. She turned her back to it, hiked up her skirt, bent over, and peaked around to look at her backside in the mirror. The base of the plug was still there, and nothing seemed to have changed. That, at least, was a relief. It hadn't somehow burrowed itself deeper and gotten lost up her ass. It was becoming so uncomfortable that she reached behind and grasped the base, thinking to pull it out or at least adjust something in there.

Holly let out a yelp as a surge of electricity ran up her arms. She found herself a moment later sprawled across the bathroom floor taking stock of what had just happened. The moment her fingers had contacted the external part of her plug she felt a shock begin at the points of contact. It ran through her hand and up her elbow and nearly to her shoulder by the time she withdrew her hand and the sensation stopped. Holly was left now with the painful tingling aftereffects.

What the fuck was that, she thought. And where was Ms. Witherspoon? Shouldn't she have charged in after hearing her patient shriek loudly in the bathroom?

Holly stood up and collected herself. She washed her hands at the sink and returned to the room, not even trying to hide her bowlegged walk. Ms. Witherspoon was still seated behind her desk as if nothing out of the ordinary had happened. Holly sat. If anything, the fullness in her backside had increased.

"The strangest thing just happened," she began.

Ms. Witherspoon interrupted. "You should not have done that."

Holly's mouth hung open in surprise. "Done what?" Her voice trailed off into an ellipsis. How could she know?

"You should not have tried to remove your butt plug. You caused it to deploy its security feature, which I'm sure you are well aware of by now. If unauthorized attempts are made to remove the plug, a generous electric shock will be delivered. That was the lowest possible setting, but if you attempt again, you will encounter progressively higher voltages."

"Oh, ok. I'm just trying to process this information." She paused and considered. "So how do I make an authorized attempt? It's just that this thing is getting uncomfortable. Like when I first put it in, everything felt fine. But it's getting really uncomfortable now."

"I thought you would have realized." The therapist cut in again. "Don't you know? This," she held up the tablet, "controls your plug. I've been progressively inflating and expanding it during our encounter. If we just allow that to remain the size it was when you inserted it, we wouldn't be getting anywhere at all, now would we? You told me that your motivation is a nine out of ten. You are going to need to make a lot of progress in the next few days if you hope to accommodate your husband after you return home. We will be preparing and training you in many different ways. Mentally. Emotionally. And to physically prepare you we must begin by dilating your anus. We will stretch the muscles and soft tissues around it for you to achieve your goal.

"I would ask you if you still want to pursue the goal, but I am sorry to say that it's too late. The time to decide has passed. We are at a point of no return. That plug cannot be removed until you have ascended to Level Two in the program."

Holly sat in dumbfounded silence. She instinctively glanced to the floor beside her, where she ordinarily would have set her purse down. Seeing nothing, she leaned over looking for it. She needed her phone. She wanted to call her husband and get him to pick her up immediately. Then she remembered; the entry attendants had taken the bags from the car for her. Hopefully she'd find them waiting in her room later.

"You won't be needing it." Ms. Witherspoon's voice cut through the fog of Holly's internal dialogue.

"Needing what?"

"Whatever it is you are looking for, your phone, your purse, anything in it, lipstick, whatever. Everything you need will be provided. Beyond that, nothing else will be given. In order to ensure that you do not acquire anything unnecessary, your bags have been locked away for the weekend. You will get them back at checkout."

At this point, all conscious thought receded from Holly's brain. She went numb. She could no longer process the information as it arose. She had somehow been kidnapped of her own volition.

And she was pretty sure the plug had just expanded one setting further. She could feel her anus opening. Without her consent, without her knowledge, it was being opened as she sat in an office across from an ice queen from Hell and processed the fact that she had zero control over the next three days of her life.

Silence continued for the remainder of their session. Ms. Witherspoon made no further attempts to engage in conversation. Holly asked no further questions, made no more side glances, and idled in neutral, awaiting what was next. Agonizingly slowly their time together expired.

Ms. Witherspoon stood up. "All right now. It is time to be moving on. I'll take you to dinner, and you can meet the others." Holly followed her out the door and down several hallways. Her posture sagged; she shuffled her feet; the edges of her vision blurred. She had not yet submitted, but she was in the processes of submitting. She could not see a way out.