Caroline the Teenage Bum Slut

Caroline loved this part. Her mother helped her hop up onto the examination table and assume the same position her mother had just occupied. "That's a good girl," said her mother softly as she stroked her cheek with one hand and caressed her backside with the other. Caroline's youthful flexibility had allowed the doctor to adjust the stirrups so that her ankles were actually behind her head. Dr. Michelle insisted this allowed for better access to her back hole. The doctor had meanwhile pulled on a long surgical rubber glove that reached up past her elbow and started to cover it with medical strength lubricant.

"Ok honey, first I have to take out your plug so I can examine you, OK? "Caroline only moaned in response as the 4" plug was slowly and delicately removed from her behind. Once the plug had been removed, Caroline's mother pulled open her daughter's butt cheeks as her anus opened ready to be filled again.

"Ok Caroline, are you ready for your anal examination?" asked Dr. Michelle. Caroline nodded as she looked at the doctor smiling. Dr. Michelle then wasted no time as she slowly pushed her whole hand straight into Caroline's willing anus that readily opened to accommodate the intrusion. She slowly and steadily started to pound the stretched out hole with medical precision, making Caroline moan with pleasure as she enjoyed the feeling of being stuffed. Her mother watched on, smiling and proud, as she held her daughters cheeks wide apart. Dr Michelle had her arm buried past her elbow in Caroline's rectum in no time at all. She expertly used the shape of her elbow to pop back and forth through Caroline's unresisting sphincter to force it open another fraction of an inch. All Caroline could do through the entire procedure was moan and gasp.

The fisting continued for a full twenty minutes as the Doctor got deeper and deeper inside Caroline's bum hole; exploring every inch of her back passage with her fist, forearm, elbow and eventually a good portion of her bicep. The poor girl couldn't help herself and was leaking juices from her sopping wet fully exposed vagina; Dr. Michelle used a sterile medical sponge to wipe up the girls pretty, hairless lips as she continued to work on her ass.

When the Doctor finally pulled her arm from Caroline's anus, she was sweating profusely with a wide satisfied grin across her face. Both women looked on delighted and satisfied at the sight of Caroline's wide gaping bum hole as Caroline lay in the stirrups and tried to catch her breath. Caroline's butt plug was then reinserted and Caroline was helped to her shaky feet.

"You've made some excellent progress, Caroline," Dr. Michelle said as she readjusted her clothes, and her own plug. "I think you're ready for the next few larger sizes of plugs; though not quite ready for the Anal Admiral line yet, but you should be there by the time you're 20."

"Thanks, Dr. Michelle," Caroline answered. "Me and my mum work really hard at keeping me wide open."

"And it shows. Keep up the good work. Now if you'll excuse me, I have some things to catch up on. Naomi can take care of the paperwork and schedule your next appointment. Oh, could you tell Naomi to send Nurse Kelly to my office with my next size; she'll know what I mean." All three women exchanged knowing glances as they left the exam room.

Naomi sat behind her receptionists' desk and greeted them with a smile as they walked up. "All finished up I see."

"Yes. Caroline did great. Could we set the next appointment up for the 3^rd? You should have all our information on file." Susan said as they reached the desk. The back side of the desk was lower than the front and they could see Naomi's lower body now. They were shocked to see Naomi naked from the waist down with her legs doubled up and cuffed so that her heels were touching her butt. She was resting atop a large orange cone with black graded tick marks to delineate diameters; the cone was of course embedded in what had to be her largely distended anus. It was easy to tell that Naomi was open to well over 8" mark by now.

Naomi noticed the direction of the two women's eyes and explained her predicament for the umpteenth time that day. "I was late for work again this morning and I have to sit on the punishment chair all day instead of wearing my usual uniform plug. I've been here since 7:45 this morning, which is why I've sunk so far down on this thing. It's better than being unemployed, and I probably deserve it!" she laughed. "Dr. Michelle tells me that I wouldn't have dilated so much if it weren't for my heavy breasts," she laughed again and squeezed her giant breasts together for added effect. Caroline and Susan joined her.

"If you're worried about the size of your asshole, you're working in the wrong place," Susan came back and Naomi smiled and agreed. "By the way, Dr. Michelle wants Nurse Kelly to bring her next size to her office."

Naomi nodded and picked up the phone to relay the message to Nurse Kelly and returned to her work. A few minutes later, Nurse Kelly walked by holding an 8" Anal Admiral butt plug in her hands like a good French waiter would hold the main course. It was an imposing chunk of latex indeed and all four women couldn't take their eyes off it knowing that it would very soon be forcing open the anal walls of a well stuffed female doctor. "Damn it! You win the bet, Naomi," she said as she passed the receptionists' desk. "I didn't think she'd be ready for me to ram this in her until tomorrow afternoon."

"I think she got a little too excited with us," Susan said as Naomi handed over the appointment confirmation card for Caroline's next appointment.

"Then I owe the two of you!" Naomi stated. "And Mr. Dr. Michelle is in for one memorable anniversary!"

"So, what was the bet for?" inquired Caroline as she and her mother turned to leave.

"Well, let's just say that I'm not the one who's going to be sitting on the punishment chair tomorrow; and Kelly has to move around all day. That's why this thing has wheels!" she grinned, pleased at having won the bet.

* * *

"You did really well today honey," said Caroline's mum.

"Thanks mum it felt so good, I can't wait till next time," replied Caroline.

"How bout we go and get some ice cream now?" suggested Caroline's mum.

"Sounds good, but do you think afterwards we can go to the toy store?" By 'toy store' Caroline meant the local Adult store.

Her mother not only encouraged and nurtured her daughter's anal obsession, but also took her daughter by her own request to adult shops, where she would buy Caroline the biggest and nastiest toys to use on her ass. While Caroline's collection of dildos, butt plugs, stimulators and anal beads was growing more impressive with each passing month, it was still dwarfed in comparison to Susan's. The young bum slut just about always had one of her toys up her ass; that was of course when she didn't have a fist up there.

Her favorite toy however was the rocking sex chair her mother had bought her for her last birthday. It was a rocking seat with a pivoting thrust arm that pounded a large dildo in and out of her ass as she rocked back and forward. She loved it and would sometimes even sit on it and pound her ass as she watched TV, like some people would use an exercise machine.

After they had ice cream, they headed down to the local adult store. Caroline's Mum didn't like her daughter being exposed to some of the sleazy pornography in there, but she did enjoy the naughty feeling of taking her 18 year old daughter still wearing her school uniform, out to buy sex toys to use on her ass. Holding hands they made a beeline for the sex toy section. Caroline looked around at all the toys in various sizes and shapes until something caught her eye.

"Mum what about this one?"

"I don't know Caroline; that's huge. Do you think you'll be able to take it all?"

"I'm sure I could mum," said Caroline, holding up the monstrous butt plug that measured 5.5" in diameter at it largest part.

"Are you sure, I don't want you to be disappointed if it's too much for you to handle."

"I know I can do it, it will be a challenge but I really want to have it up my bum, please mum."

"Ok then honey, if you think you're ready for it lets get you home and get that butt stuffed then, shall we?"

With that they made their purchase and headed for home. Caroline's household consisted of her divorced mother Susan, her 20 year old sister Rachel, and herself. Although Rachel didn't spend much time at home these days as she had a pretty serious girlfriend, she was close with her sister and always willing to help her out with anal play whenever she asked.

* * *

"Come in!" Nurse Kelly heard the doctor's muffled voice through the nearly soundproof door of Dr. Michelle's private office. Dr. Michelle sent a quick glance towards the door as Kelly entered the large room. "Ah, there you are. I'll be ready in a tick", Dr. Michelle said as she stood at her wardrobe and undressed herself.

As always when she got to see her young boss naked, Nurse Kelly sneaked some quick looks at Dr. Michelle's marvelous body; slender but well-proportioned and athletically trained. The base of the massive plug stretching her well-trained asshole was clearly visible between the Doctor's exquisitely shaped buttocks. Nurse Kelly knew from personal experience that that ring of anal muscle could be stretched almost ad infinitum.

The entire image was a breathtaking sight!

The Nurse walked up to a cart standing next to the exam table and placed the black, heavy rubber monster on the cart's stainless surface.

"I was surprised that you were ready to try Mr. Big today," Kelly commented. "I didn't think that you would ask for it until tomorrow," she continued as she donned rubber gloves and turned towards the now naked Dr. Michelle.

"Well, I just feel that I'm quite relaxed down there and I want to see if I could perhaps can go up to even 8.25" by Friday", Dr. Michelle said as she finished hanging up her trousers. "Just think how excited hubby will be at that thought!

"Ready when you are!"

The pretty nurse smiled evilly at the thought of her boss crying and begging for mercy as her husband used her for his pleasure before responding. "Okay then, up on the table please, Doctor!" Dr. Michelle went to her own private examination table and lay down on her back as her underling had requested. She made it a point to 'examine' each and every one of her nurses several times a day on this very table, but only allowed a few select nurses to open her up a couple of times a week. It wouldn't do well for discipline if all of her employees knew what she looked like on the inside!

"Would you like to be strapped down?" Nurse Kelly asked as she helped Dr. Michelle to put her feet in the massively built footrests.

"What a silly question, Nurse Kelly. Of course!" the good doctor said with a hint of exasperation.

Working quickly, Kelly fastened the straps at the Doctor's insteps, ankles, knees, wrists and her finally her waist. Then she adjusted the stirrups' ratchet mechanism until Dr. Michelle was fixed in a wide spread position; even slightly more extreme than the one Caroline had been in just a few minutes ago. Dr. Michelle grunted softly as Nurse Kelly brought the lever down into the final notch.

"Comfortable, Doctor?" the nurse asked politely.

"Not very, but that's not really the point, now is it?"

"Fair enough," responded Kelly. "Now, let's see what we've got in here," she continued kiddingly as she took a seat on the stool in front of Dr. Michelle's widely spread legs and well-shaped ass. She had to bite her lower lip as the familiar sensation of her own uncomfortably plugged ass made contact with the stool's hard surface.

After she had herself situated as comfortably as she could, Nurse Kelly grabbed the base of the humongous plug buried in her boss's sexy butt and tried to extract it. It was like trying to pull out a nail out of a wall. Kelly turned the plug to and fro, but even this required a lot of effort. Dr. Michelle gasped and groaned softly as Kelly's efforts did little more than slightly shift the seized plug.

"I think we need to use the extraction-handle", Kelly announced after several failed attempts. The Nurse stood up and got the screw-in handle out of a drawer. This was not the first time she had to use this gadget to yank something huge out of her employer's ass; it was actually pretty common.

Thankfully, the manufacturers of the Anal Admiral series of butt plugs had molded a connection thread into the base of each plug. While this feature could be used as a fastening point for handles, the primarily purpose of the threading was to fix the plugs onto the Impaling-Chair™; one of the top-selling accessories for the Admiral's line. Since this series is one of the most ambitious when it comes to thickness -- beginning with relatively easy 6" and continuously increasing up to an almost unbelievable 10" -- they are extremely difficult for a girl to handle by herself. This helpful, ruggedly-built chair has a threaded bolt in the middle of the seat which can be turned with a lever protruding at the stool's front. The girl sits down with the plug stuck in her butt, screws it to the stool and can now try to stand up and pull her little -- or perhaps huge -- friend out of her butt.

Alternatively, she can fix her next challenger to the seat, squat down on it with her eager ass, and then put her feet on footrests and strap them down. She can now recline in the straight backed chair and enjoy how her full weight lets her sink down slowly on her beloved latex cone. If she opts for the larger sizes, additional hand straps are provided under the seat so that she can increase the force by pulling herself down with all her might.

Nurse Kelly sat down again and screwed the massive two-handed extraction-grip into the plug trapped in her boss's ass. Already, with the first tentative attempt, Kelly was now able to move the plug clockwise and to pull it out for a few millimeters. Dr. Michelle whined quietly as she felt the acute pain that her tortured sphincter instantly started to emit. "Here we go!" Kelly announced and began to move the handle with brute force. Dr. Michelle braced herself for the coming agony, took a deep breath, clenched her teeth, and tried not to scream out in pain. The suffering was overwhelming. Every single millimeter that her already grotesquely distended sphincter was opened gave her more unbearable misery. Even though her asshole had been kept open for the whole day by the neck of the 7" plug, it was still unwilling to be opened up further to 7.75".

Dr. Michelle groaned with pain as Nurse Kelly violently worked on her ass. Every yank and pull on the handle slowly dislodged the horrible plug little by little, and pulled her sphincter outwards more and more. Despite her years of medical and anal dilation training, Dr. Michelle couldn't help but start to sob and cry pitifully as her anus was distended wider and wider as Nurse Kelly dutifully worked to extract the latex toy.

"It's coming out now, just a little bit more," Kelly tried to motivate her sniveling boss. Then, with a last powerful jerk, the huge black butt-buster came free with a loud, wet pop. Dr. Michelle took a deep breath and let out a short but loud cry of anguish. "Mmmm, that looks incredibly healthy", Nurse Kelly stated as she admired Dr. Michelle's obscenely gaping anus. "Let me just do a quick exam before we move on to this nice black piece of latex over there," Kelly said as she nodded over her shoulder at the significantly larger plug that was patiently waiting for its turn to violate Dr. Michelle's poor, dilapidated rectum. The ruined ring of muscle hung loosely open, roughly the same diameter as the base of the plug that had just been extracted.

The nurse smeared a generous amount of lube onto her elbow-length gloves and inserted both of her fists into Dr. Michelle's still widely open ass. "Ah, yesss..." was all Dr. Michelle could answer to the welcome intrusion. With mighty thrusts Kelly worked her arms in up to her elbows in almost no time. She intertwined her fingers to make one giant fist and pulled out with full force; and then in again in one forceful motion. Soon she was fisting her moaning boss at full speed.

Despite the immense soreness caused by her plug's sheer size, Dr. Michelle still loved her asshole being brutally fisted, above all else. "Deeper!" she commanded.

Kelly smiled knowingly and slowly pressed the bulge of both her elbows deeper into her target. The doctor's ass struggled to open up more, but finally it lost the battle and Kelly was in up to her biceps; back out and in again. As she fucked the doctor's rectum, she pulled her elbows apart to loosen her boss' ass for its real challenge waiting next to her on the cart. As a final preparatory step, Kelly fisted Dr. Michelle alternating with both arms up to the middle of her biceps. This finally brought her over the edge and Dr. Michelle exploded in an earthshaking orgasm.

The nurse was all smiles. "Now you might be relaxed enough to face Mr. Big," she announced as she reached over for the next step in this extreme treatment. After Dr. Michelle recovered her breath and Kelly had lubed the impressive butt spreader, she positioned the 8" plug at Dr. Michelle's tiny ass. "Are you ready for the full 8 inches?" Kelly asked rhetorically.

"Yes, please! I want to take it in me now," Dr. Michelle said calmly, fully aware of the ordeal waiting for her; a self-imposed ordeal at that.

Nurse Kelly began to press the 12" long, gently thickening cone into its target. The plug had sunk just halfway into its new home before Kelly started to notice serious resistance. "This will be slow going", Kelly thought.

Again and again she pressed the cone in to loosen the sphincter. Then she stood up and leaned against the plug to apply more force on it. Dr. Michelle gasped as her ass was spread wider and wider.

Very slowly -- only a tiny fraction of an inch each time Kelly pushed -- the huge plug sank deeper into the heavily breathing woman. Nurse Kelly had a thorough education in extreme anal treatments, learned mostly firsthand from the woman bound to the chair in front of her. Under her increased efforts the plug sunk deeper into the resistant ass. Finally she reached the last third of the horrible toy. With true professional composure, she ignored the despairing moans of Dr. Michelle and focused her effort on further violating the now openly crying woman.

Dr. Michelle had closed her watering eyes and was trying to bravely suppress her screams. Wave after wave of excruciating pain emitted from her tortured rectum as Nurse Kelly relentlessly worked the plug in deeper. She knew that the nurse would show no mercy to her, as she might do to a patient; she had trained her subordinate too well for that. Michelle clenched her teeth and tried to relax her sphincter to yield to her self-imposed fate.

Shortly thereafter Kelly took a step back and grabbed the plug's base with both her hands. Then she leaned forward and pushed the plug in with straight arms. "Push!" she barked to the moaning Dr. Michelle. The Doctor took a deep breath and pushed her aching rectum outward. As Kelly sensed the sphincter relaxing, she pressed the cone in with all her might. Slowly it disappeared more and more. This was repeated until the last inch of the cone was reached. The pain was now excruciating, to such an extent that Dr. Michelle had disappeared into a nirvana that only the most truly gifted anal masochists could ever achieve.

Dripping with sweat, Nurse Kelly pressed the 8" plug with more force into her victim. Finally, after more than 40 minutes of strenuous efforts, just a fraction of an inch was left and the widest part of the plug lay firmly between the doctor's horribly dilated anus. Kelly flexed all her muscles and with a last, vigorous push the plug at long last disappeared up to its 7.5" neck. Dr. Michelle felt blinding agony from the final push in her tortured ass. Wide-eyed she screamed out in immense pain.