Lord Odie's "Caroline the Teenage Bum Slut"

[lordodie]

I thought I would give you guys a tidbit of my early writing.  A few years ago - before I started writing on my own - I took the first chapter of "Caroline the Teenage Bum Slut" and added my own kinks to it.  It was basically a dry-run to test my ideas and it would eventually become my Anal Etiquette series.  I've attached the modified story below.

 

I'm posting it here as a preview, but I'm going to get the original author's permission before I post it to Literotica.  Enjoy!

 

 

 

 

Caroline the Teenage Bum Slut

Adapted by: Lord Odie

 

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is meant as a compliment. Furthermore, all fictional characters in the following fantasy are professionals and good at what they do. So please, don’t try this at home; if such things were even physically possible. If you still insist on trying this at home, please send all pictures and feedback about the experience to myself at: lordodietheauthor@gmail.com. If I can’t stop you I can at least make sure you’re doing it right. Consider yourself disclaimed.

 

 

 

It was hard to deny; 18 year old Caroline Evans loved nothing better than to have one of her friends sticking something big up her butt, whether it was an oversized dildo, a butt plug, a large vegetable or most of all a girl’s fist. Caroline spent all the free time she could getting her ass pounded in some way by at least one of her female school friends at the liberal all girls school she attended.

 

Caroline was a bright student who was liked by her teachers and easily did well in her classes, but it’s what she did between classes with her fellow students and even some of her teachers that made her a true bum slut. Not a day went by without Caroline having as many girls’ fists and other large objects buried deep inside her favorite body part: her loose, often obscenely stretched, bum hole.

 

“Hi Miss Hunter” said Caroline, as she walked into class holding the hands of two of her friends as was normal for her; she almost never went anywhere without at least two of her friends either holding her hands or fondling her behind.

 

“Hi Caroline, how are you?” said a chirpy Miss Hunter.

 

“Fine thanks, Miss Hunter,” said Caroline as she walked into class flirtatiously displaying her bottom to her teacher wearing her usual uniform of the school blouse and pair of dark green ultra short Lycra bike pants that only covered three quarters of her behind and rode right up the crack of her sexy backside.

 

Caroline got away with wearing such revealing clothing since bike pants were allowed as part of the sports uniform; she just wore them all the time. The teachers didn’t seem to mind her revealing attire, nor did they seem to mind when she would frequently walk around the school grounds surrounded by her friends wearing nothing but her blouse and her Mary Jane school shoes.

 

Caroline was an attractive girl and loved to show off her body, she had athletic toned legs that ended in a perfectly formed gorgeous round bubble butt that just begged to be stuffed with something. She had largish round perky teenaged breasts and just a little bit of baby fat which made her look extra cute. It was all topped off by a pretty round face that was framed by her sandy brown hair cut into a sexy bob style.

 

Caroline did her best to pay attention in Miss Hunter’s class, but it was hard as she fantasized about how good it would feel to be on all fours on the teachers desk, with her pants round her ankles and Miss Hunters fist deep inside her ass, with her friends helping as the class watched on. But that would have to wait for now.

 

When the bell rang for lunch, Caroline and her group of five best friends Jodie, Amy, Sarah, Mandy and Jess all headed for their usual spot in a quiet and secluded corner just at the top of the school oval beside a small retaining wall. It was not so hidden that they couldn’t be seen by anyone who wanted to find them, but secluded enough that they could have their privacy. And privacy is what they needed.

 

On the way Caroline’s friends Jodie and Amy held her hands while Mandy followed behind fondling her backside. Caroline loved to parade through the school like this showing off her sexy plump bubble butt stuffed with a butt plug. When she could get away with it, she loved nothing better than to lose her pants and flaunt her bare backside and smooth bald vagina to as many girls as possible. Some girls thought she was just a big slut, but just as many also would’ve loved to have been her girlfriend. She always declined their advances however as she liked to share herself around with as many girls, and women, as possible.

 

Caroline and her friends reached their little love nest as she assumed her favorite position: lying on her stomach with her bottom invitingly poking into air. Jodie started the day’s fun by slowly peeling down her friends Lycra pants to reveal her glorious bum cheeks between which lay a large black butt plug.

 

“Oh my god it’s so big, how does it feel?” said Caroline’s friend Amy.

 

“Mmmm...it feels so good up there, but a fist would be better,” replied a horny sounding Caroline.

 

“Who wants to pull out my plug so you guys can fill me back up?” beckoned Caroline as she reached back with both hands to spread her tones ass cheeks apart.

 

It was her friend Jess that took the lead and slowly pulled out the large plug that measured 3.5” wide at its largest part; by no means her biggest, but certainly filling for everyday use.

 

All the girls watched on as the plug slowly stretched out her sphincter before it finely popped out and her asshole did its best to return to its usual elongated semi-closed position; it’d been years since Caroline’s asshole had been able to truly close. By now the ever present lube had been brought out and was being liberally and lovingly applied to Caroline’s anus by Jodie. Her fingers easily slid in and out of Caroline’s stretched out hole as she applied the lubricant four fingers at a time. It wasn’t long before she had slipped her thumb in and her whole fist had disappeared up Caroline’s delicious backside.

 

Caroline looked back at Jodie with a look of open mouthed ecstasy as her friend started too slowly and rhythmically fist her best friend’s ass, going deeper with each thrust. It wasn’t long before her friend Amy laid a soft kiss on Caroline’s lips that quickly turned into deep erotic French kissing. Caroline loved to make out with her friends in their ass play sessions, which would usually involve lots of kissing.

 

All the girls crowded round gently stroking and caressing Caroline’s body, loving the sight of her distended anus being stretched beyond belief. Amy gently stroked Caroline’s pretty hair telling her what a sexy bum slut she was. After five minutes of relentless pounding by Jodie, Mandy took over and was soon forearm deep in an overjoyed Caroline’s ass. After another five minutes or so of continuous fisting, Mandy’s elbow was brushing against Caroline’s anus on each inward stroke. Mandy would pull her arm out until her fist was tugging at Caroline’s lose ass lips, almost but not quite popping out, before she would sink her arm back into the depths of Caroline’s rectum.

 

Jess was next up and picked up where Mandy had left off; sawing her whole arm in and out of Caroline’s dilated bum hole, wrist to elbow on each stroke. After Jess ran out of steam Sarah pick up the slack. Sarah usually didn’t go elbow deep on Caroline like the others did. She liked to ball up her first and punch it in and out of Caroline’s now gaping ass and watch the worn out anus try in vain to close itself as it was briefly left unfilled and un-stretched. Caroline, enjoying the different sensation, moaned and gyrated her hips to the rhythm of Sarah’s punching fist.

 

When Sarah eventually tired of punch fucking her friend’s ass, it was finally Amy’s turn to violate Caroline’s lovely bottom. Amy really liked finishing Caroline off so she usually went last. She quickly buried her arm up to the elbow in Caroline’s distended anus without meeting any resistance at all. Once buried to the hilt, Amy began twisting her arm and fist around and bumping her arm forward trying to sink the edge of her elbow up her friend’s gyrating ass. When Caroline was really excited and loose, Amy could actually accomplish this feat; as was the case today. All the girls cheered when Caroline’s slutty bum hole finally closed around the base of Amy’s bicep. All Caroline could do was moan loudly while reaching back with both hands to spread her cheeks as wide as she could.

 

For almost half an hour, Caroline moaned and grunted with pleasure as her friends urged each other on to go harder and deeper. It was a wonderful sight, all the girls crowded round worshipping their friend’s slutty loose bum. By the end of lunch break all the girls had had a turn putting their whole arms up a horny and moaning Caroline’s bum hole; Caroline’s ass was a gaping, sloppy mess. The girls helped clean her up and reinserted a slightly larger 4” butt plug. Whatever plug Caroline started the day off with was usually too small to stay in after their lunchtime get-togethers, so Caroline always carried one or two larger butt plugs in her purse. That way her horny butthole could stay pleasantly stretched all afternoon. They then all headed back to class to finish off the school day.

 

*             *             *

 

When school got out that afternoon Caroline said goodbye to her friends and went to meet up with her waiting mother in the school car park.

 

“Hey, honey. How was school today?” asked Caroline’s mum Susan, as they exchanged their usual mother/daughter kiss – which involved more tongue and ass grabbing than was probably appropriate.  Susan was an older version of her daughter, but only grown into her body. Susan could best be described as voluptuous; curves a plenty in all the right places. She was a wet dream for ass-men and breast-men alike. Caroline had some large shoes – and cups – to fill before she grew into her mother’s figure.  Finally their inappropriate embrace ended.

 

“Really good, me and my friends had heaps of fun at lunch,” replied Caroline as she got in the car.

 

“I bet you did,” said Caroline’s mum with a knowing smile. “Ready for your appointment with Dr. Michelle, honey?” asked Caroline’s mum.

 

“I’ve been thinking about it all day,” replied Caroline excitedly.

 

Susan always arranged for both her daughters to attend fortnightly ‘consultations’ with Dr. Michelle at a small privately owned clinic that specialized in the treatment of young women. Caroline always looked forward to the appointments and the special anal examinations she would receive.

 

When Caroline and her mother arrived at the clinic Caroline was still wearing her cute and revealing school uniform. They walked into the clinic with her mother holding her hand as was usual for them. After confirming their appointment with Naomi, the pretty and exceptionally well endowed red headed receptionist, Caroline was asked to remove her clothes and take a seat in the waiting room. Caroline loved this part, as taking her clothes off in a public place was one of her favorite things. Her mother helped her strip off her uniform and then folded it in a neat pile.

 

Susan was also required to strip from the waist down as it was the clinic’s standing policy that all patrons have their backsides available for the doctor’s ‘consultations’ if it was required; and it was almost always required. Caroline was treated to a brief glimpse of what she assumed was her mum’s massive butt plug before Susan finished folding her business suit’s slacks and sat down with her. They then waited and chatted softly for Caroline’s name to be called.

 

It wasn’t long before the door opened and an attractive, dominant looking woman wearing a white medical coat exited. Dr. Michelle was very attractive, had an athletic physic, medium sized breasts, jet black hair and was in her early thirties. As she walked, she was talking to an attractive blond woman and what Caroline assumed was her daughter. The daughter was naked and the mother bare from the waist down, as was to be expected. The daughter was walking slightly bowlegged and was obviously struggling to accommodate something rather large lodged in her bum. Caroline could also see the base of a matching something peeking out from between the mother’s shapely butt cheeks.

 

“Just remember to keep checking Amanda’s plug every night before she goes to bed. If you can force a finger in beside it, she needs to be fitted with a larger one before she goes to sleep. Hopefully, we can get her anal expansion back on schedule again by her next visit,” Dr. Michelle said to the blond mother.

 

“Of course, doctor. I’ll stay on top of her better from now on,” the woman replied.

 

“Glad to hear it; Naomi will take care of the paperwork with your insurance. Oh and Naomi, Schedule Mrs. Hill for an appointment of her own later this week; her plug had a lot of slack in it and I’m running too far behind this afternoon to fit her with a properly sized one today,” Mrs. Hill looked slightly taken aback, but nodded her consent to Naomi.

 

“Just a fitting session, doctor? Or should I schedule Mrs. Hill for a stretching session prior to it?” Naomi asked un-phased at the nonchalant discussion of another woman’s anal dilation – such talked was obviously quite common at the clinic. Mrs. Hill turned a light shade of red from the embarrassment of having the stretching and plugging of her most private hole talked about openly in front of her daughter.

 

“I think both would be appropriate, don’t you think, Mrs. Hill?” Amanda’s mother only nodded her head silently in agreement. “That way we can fit you with a more comfortable plug quickly and get you on your way. I know the fear of having a too small butt plug slip out of your anus in public is something no woman should have to worry about!” With that, Dr. Michelle nodded a final time to Naomi and turned her attention to her next patient.

 

“Hello, Caroline!” Dr. Michelle said as she entered the waiting room. “Come this way back to the exam room. How have you been?” she asked as they followed her back.

 

“Really good thanks, Dr. Michelle.” replied Caroline.

 

“Have you been looking after your bottom like a good girl?”

 

“Yes! Every day, doctor,” replied Caroline.

 

“I’m pleased to hear that,” said Dr. Michelle as they entered her examination room and she closed the door behind them. “As you probably overheard, not all of my patients – or their mums – are as proactive as you.” Turning towards Caroline’s mum, “I know I can always count on Mrs. Evans to have an appropriately sized plug filling up her backside, and her daughter can almost always be counted on for the same!”

 

“Why thank you, Dr. Michelle! I for one never want a plug that I’m wearing to slip out in public. I might die from the embarrassment!” Susan replied, giggling slightly.

 

“Why don’t I check you out quickly before we get on to your daughter’s exam. I need to make sure her caregiver is setting the right example.” Susan nodded emphatically in agreement. “Go ahead and have a seat and put your feet in the stirrups… There we go… Now let’s just adjust these stirrups so we can have a good look at you… Ah! Very nice.” Susan was now lying on her back on the exam table with her legs spread wide at a 90 degree angle, with her ankles almost back to the level of her ears. This left Susan’s bald vagina open for the world to see; or at least just Dr. Michelle and Caroline. Susan’s vagina gaped slightly and it was easy to see her moist inner labia. This wasn’t from it being well fucked; it was due to the stretching of the truly massive plug protruding from her backside.

 

And that nether hole truly was well fucked indeed. The women of the Evans household had always been very open about sex, and specifically anal sex in all its varieties. While most girls in high school giggled at hearing the word ‘penis’ in health class, Caroline and her sister Rachel had already known half the Kama Sutra; at least in theory if not in practice. Seeing her mum spread wide open on display like that was nothing new for Caroline, and she leaned in close to get a better look at the latex monster invading her mother’s rear hole.

 

“Alright, let’s see what we have here,” Dr. Michelle said, sitting down at the foot of the table and taking hold of the base of Caroline’s mum’s wide butt stretcher. Dr. Michelle turned the plug clockwise and counterclockwise while pulling outward more and more forcefully. Susan started to moan and then gasp as the plugs widest part neared exiting her body. Susan’s sphincter was pulling farther and farther away from her body the further Dr. Michelle pulled the plug out. Finally, with an audible pop, the plug came free with only a muffled cry from Susan; her abused asshole not even trying to close itself after decades of self inflicted dilation; the poor hole just gaped obscenely open.

 

“Ah… The Anal Admiral series of plugs,” Dr. Michelle commented as she tried to wrap both her hands around the circumference of the mammoth plug and failed. “I believe this is the 7” model with the 6.5” neck; very serious hardware. I recommend these to all my advanced butt sluts. I wear a similar model to work, although I prefer a larger one for play.” Caroline gasped, loud enough for Dr. Michelle to hear, at the thought of this professional looking doctor, well respected in her field, showing up to work every day with her anus grossly stretched by 7” of latex.

 

Dr. Michelle only smiled and turned towards Caroline. “You don’t think I would have gotten this far, and with such a lucrative practice, if I didn’t practice what I preached, do you?” she asked. “Before I can recommend women push their bodies to their physical limits, I have to know my own.”

 

“You mean, you’re wearing a 7” butt plug right now?” Caroline asked amazed.

 

Dr. Michelle turned slightly red and lost her dominant aura for a moment as she re-lubricated Susan’s heavy plug and lined it back up with the battered asshole for reinsertion. Susan began to gasp and pant as the 7” bulge once again made another of its frequent trips through her yielding sphincter. “Well, this weekend is my husband and my wedding anniversary and we’re going away for a four day weekend, so I figured I’d give him a special present. My husband really loves how tight I am during vaginal intercourse while I’m wearing one of my larger plugs, so I’ve actually been dilating myself more than usual this week in preparation. I’m actually wearing a 7.75” butt spreader. I should be up to an 8” plug by the time we take off on Friday.” Dr Michelle looked dreamily at Susan’s plug as it finally slid home in her rectum once again; thinking more of the pain emanating from her own well stretched sphincter than the pain she was inflicting on Susan. Dr. Michelle shook herself back to the present and her dominant aura retuned instantly.

 

“Good job, Mrs. Evans,” she said releasing the tension on the exam table’s stirrups and lowering Susan’s feet to the floor. “Keep up the good work.”

 

“Now, onto the real exam,” Dr. Michelle said and started by asking some routine and mundane medical questions as she always did before she moved on to asking Caroline about the frequency of her bowel movements, flatulence, how often she wore a butt plug, what size and her daily anal hygiene practices. “Ok sweaty, can I get you to hop up on the examination table for me,” she said finally.

 

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 dexterity 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 a 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. “Dam 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. Caroline had quite a collection of dildos, butt plugs, stimulators and anal beads and just about always had one of them up her 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.

 

*                  *                  *

 

When they arrived home Rachel was there lying back on the couch watching TV; naked from the waist down. One hand was holding her legs out of the way while the other hand was buried up her pert backside as she absentmindedly popped her closed fist in and out of her loose hole.

 

“Hey Rach look what I got,” said an excited Caroline.

 

“Wow that’s huge, do you think you can take all that?” asked her sister, not pausing in her anal masturbation.

 

“Mom’s going to help me do it; can you help too?”

 

“Sure anything for my little sis,” replied Rachel as Caroline slipped out of her tight little pants.

 

“Now honey, first where going to have to get you warmed up, so I want you to go and get an extra large dildo and some lube,” instructed Caroline’s mum.

 

It wasn’t long before Caroline returned with a huge rubber dildo and some extra strength anal lube. As she walked back into the room, she saw her mother kneeling before Rachel as she pounded her fist and arm up her older daughter’s dilated anus and rectum. It was only a few seconds before the younger woman exploded in orgasm. Finally, Susan removed her fist from her daughter and re-plugged the gaping bum hole with the 6” plug laying on the couch next to the gasping woman.

 

“Sorry, Caroline,” said her mother apologetically. “Your sister just needed some release. She can play now.”

 

Caroline smiled knowingly at the pair of older women and then removed the rest of her clothes as her mother sat down on the couch next to Rachel.  She then lay across her mother’s waiting lap. Her mother removed Caroline’s butt plug with a plopping sound and quickly buried her fist up her daughter’s wide open bum hole; while her quickly recovering sister applied plenty of lube to the big nasty toy. Satisfied at the looseness of her daughter’s hole, Susan nodded to Rachel, removed her fist and placed both her hands on Caroline’s butt checks and spread them apart.

 

Rachel, using two hands to grip the monster dildo, started to work it into her sisters well used rear entrance. She guided it in and out till she had 15” of the dildo sliding and out of Caroline’s ass. Rachel always loved the sight of her sister’s cute little slutty pink hole being stretched wide as she begged for more. After 10 minutes or so of getting her ass stretched Caroline asked if she could try the plug now.

 

“Ok honey, if you think you’re ready.”

 

“I am mum, I want to feel something really big up my bum.”

 

Rachel slid the dildo from Caroline’s ass and they made their way over to the chair that they had set the obscenely large butt plug on. Susan and Rachel each held one of Caroline’s arms to balance her as she began to sit down onto the tip of the plug. She continued to push down as it got wider and wider, the strain on her face began to show as she bit down on her lip and pushed harder.

 

“That it sweetheart, keep going... take it all in,” encouraged her mother.

 

“Good work Caroline it’s almost in, you’re doing really well,” said her sister urging Caroline on.

 

“Mmm... it’s so big, but I know I can do it,” huffed Caroline.

 

Her mum and sister started to gently force her down onto the chair, as Caroline looked up at her mother with an open mouthed expression and glazed over eyes, as she could feel her sphincter starting to be stretched to breaking point.

 

“Almost there darling just a little bit more,” soothingly reassured her mother as they forced her down to the very widest part of the plug.

 

Just as she felt she was stretched to her limit the plug slipped into her ass and her backside sat down fully on the chair as her sphincter came to rest around the 5” stem of the plug. She sat there on the chair trying to adjust to the size of the object nestled in her rectum.

 

“Wow Caroline, how does it feel?” asked her sister.

 

“It... it’s good, I feel so full and stuffed back there,” stammered a breathless Caroline.

 

After Caroline had become comfortable with the plug, she decided she would like to try wearing it for the rest of the evening. She walked around the house with a slight waddle as she got used to walking with something so huge in her backside. Caroline helped her mother cook dinner, before they all sat down and ate a nice meal together and then settled down to watch a movie for the evening. Caroline lay on her stomach on the carpet with the big black base of plug obscenely parting the cheeks of her well stuffed backside.

 

[kane73]

Tks. Very nice. Waiting for more

[Redhunt7]

awesome

[colmtzar]

Nice! I knew the original, but.. like DeNiro said: you're good... no. No. No. You're good!

Waiting for the Wilders analdventures...

[dunhill]

Lord Odie's new version of one one of my favorite stories inspired me to write an addendum.

 

I would particularly like to thank lordodie, who revised my text and put it into proper English.

 

 

 

 

“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 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 as 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 out 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 stools 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’ 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 7” neck of the 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 things. “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. An 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 in the heavily breathing woman. Nurse Kelly had a thorough education in extreme anal treatments, learned mostly first hand 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. Dr. 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.

 

“Got it!” Nurse Kelly sighed with relief and satisfaction at a job well done; knowing that she would have to repeat this stretching treatment in less than 48 hours with an even bigger Anal Admiral in order for her boss to meet her goal in time for her anniversary.

 

Gently, Kelly disengaged the ratchet on the gynecological chair and allowed her boss’ legs to come together at last. Slowly, she unstrapped the doctor and helped her to stand on wobbly legs. “Alright, Doctor,” she said reassuringly. “You know the drill. Let’s get you walking so your ass can acclimate.”

 

Even as Kelly began to pull her boss into motion, Dr. Michelle begged, “Just give me a minute to adjust, Nurse Kelly,” and then moaned as the pain from her tortured anal ring shot up her spine as she took her first steps.

 

“Nonsense, Doctor! Didn’t you instruct me just yesterday when our positions were reversed that the best thing for a sphincter’s acclimation it to get the patient walking as soon as possible after insertion of a larger plug?”

 

Dr. Michelle could only nod in defeat as they completed their first lap around her spacious office.  She tried her best to be a strong, independent woman about her situation, but couldn’t help sniffling back the occasional tear as the unbelievable pain wracked her well toned, naked body.

 

After half a dozen laps, Dr. Michelle’s sobbing had subsided.  Another dozen and she could walk without being hunched over or bowlegged.  Soon, her gait was almost back to normal and her usual professional composure was quickly returning.

 

“Thank you, Nurse Kelly,” Dr. Michelle said at last as she broke away from the other woman’s grip and made her way to her wardrobe, now fully in control of herself; despite the reduced pain still pulsing out of her back hole.  “Be sure to clean up.”

 

“Yes, Doctor,” replied the nurse as she busied herself with cleaning up the discarded plug and the gynecological chair.  By the time the office was back in order, Dr. Michelle was once again fully dressed and every inch the sophisticated medical doctor.

 

“Will there be anything else before I leave, Doctor?” Kelly asked when she had finished refilling the large bottle of extra thick anal lubricant on the cart.

 

“Hmm... Oh yes!” replied the doctor. “When was the last time I checked your plug?”

 

Kelly’s heart dropped. “I believe it was yesterday afternoon, Doctor.”

 

“Yesterday? My how the time flies,” Dr. Michelle said with an evil grin as she patted the seat of the temporarily vacant chair with her strong hand.

 

Nurse Kelly only sighed. “Yes, Doctor,” she replied as her fingers worked the buttons of her uniform.

 

Dr. Michelle’s smile widened as she slipped her hands and arms into the elbow length latex gloves while Nurse Kelly stripped.

Edited December 6, 2014 by dunhill

[alongeasy]

Damn hot

[lordodie]

Lord Odie approves of this addendum...

[lordodie]

Alright, after much ado, Dunhill and I - and edited by BlackRockBoss as always - finished this project.  So here it is.  I'll be posting this on Literotica shortly.  Don't forget to head over and vote on my stuff!  :D

 

 

 

 

Caroline the Teenage Bum Slut (Redux – Chapter 1)

Originally by: Jason Hitchcock

Adapted by: LordOdie & Dunhill

 

Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictional character herein may bear is probably intentional and is meant as a compliment. Furthermore, all fictional characters in the following fantasy are professionals and good at what they do. So please, don’t try this at home; if such things were even physically possible. If you still insist on trying this at home, please send all pictures and feedback about the experience to me. If I can’t stop you I can at least make sure you’re doing it right. Consider yourself disclaimed.

 

 

 

Foreword from the Adapting Authors

 

Some of you have probably read the origin “Caroline the Teenage Bum Slut” series of stories by Jason Hitchcock.  If you haven’t, we suggest giving them a read; they’re good enough to inspire a rewrite of the first chapter by a couple of extreme anal loving authors.  You can find it readily enough through a Google search. Jason also has a few other series that are equally as good; “Elizabeth’s Bottom Training” is a personal favorite of mine!  

 

Also, in case you’re wondering, the original author has given his blessing to this redux version.  So enjoy this story and then check out Jason’s other stuff!

 

 

 

*                  *                  *

 

 

 

It was hard to deny; 18 year old Caroline Evans loved nothing better than to have one of her friends sticking something big up her butt, whether it was an oversized dildo, a butt plug, a large vegetable or, most of all, a girl’s fist. Caroline spent all the free time she could getting her ass pounded in some way by at least one of her female school friends at the liberal arts, all-girls school she attended.

 

Caroline was a bright student who was liked by her teachers and easily did well in her classes, but it’s what she did between classes with her fellow students and even some of her teachers that made her a true bum slut.  Not a day went by without Caroline having as many girls’ fists and other large objects as possible buried deep inside her favorite body part: her loose, often obscenely stretched, bum hole.

 

“Hi Miss Hunter” said Caroline, as she walked into class holding the hands of two of her friends as was normal for her; she almost never went anywhere without at least two of her friends either holding her hands or fondling her behind.

 

“Hi Caroline, how are you?” said a chirpy Miss Hunter.

 

“Fine thanks, Miss Hunter,” said Caroline as she walked into class flirtatiously displaying her bottom to her teacher wearing her usual uniform of the school blouse and pair of dark green ultra short Lycra bike pants that only covered three quarters of her behind and rode right up the crack of her sexy backside.

 

Caroline got away with wearing such revealing clothing since bike pants were allowed as part of the sports uniform; she just wore them all the time. The teachers didn’t seem to mind her revealing attire, nor did they seem to mind when she would frequently walk around the school grounds, surrounded by her friends, wearing nothing but her blouse and her Mary Jane school shoes.

 

Caroline was an attractive girl and loved to show off her body, she had athletic toned legs that ended in a perfectly formed, gorgeous round bubble butt that just begged to be stuffed with something. She had largish round perky teenaged breasts and just a little bit of baby fat which made her look extra cute. It was all topped off by a pretty, round face that was framed by her sandy brown hair cut into a sexy bob style.

 

Caroline did her best to pay attention in Miss Hunter’s class, but it was hard as she fantasized about how good it would feel to be on all fours on the teacher’s desk, with her pants round her ankles and Miss Hunter’s fist deep inside her ass, with her friends helping as the class watched on. But that would have to wait for now.

 

When the bell rang for lunch, Caroline and her group of five best friends – Jodie, Amy, Sarah, Mandy and Jess – all headed for their usual spot in a quiet and secluded corner just at the top of the school oval, beside a small retaining wall. It was not so hidden that they couldn’t be seen by anyone who wanted to find them, but secluded enough that they could have their privacy. And privacy is what they needed.

 

On the way, Caroline’s friends Jodie and Amy held her hands while Mandy followed behind fondling her backside. Caroline loved to parade through the school like this showing off her sexy plump bubble butt stuffed with a butt plug. When she could get away with it, she loved nothing better than to lose her pants and flaunt her bare backside and smooth bald vagina to as many girls as possible. Some girls thought she was just a big slut, but just as many also would’ve loved to have been one of her girlfriends. She rarely declined their advances however, as she liked to share herself around with as many girls – and women – as possible.

 

Caroline and her friends reached their little love nest as she assumed her favorite position: lying on her stomach with her bottom invitingly poking into air. Jodie started the day’s fun by slowly peeling down her friends Lycra pants to reveal her glorious bum cheeks between which lay a large black butt plug.

 

“Oh my god it’s so big, how does it feel?” said Caroline’s friend Amy.

 

“Mmmm... it feels so good up there, but a fist would be better,” replied a horny sounding Caroline.

 

“Who wants to pull out my plug so you guys can fill me back up?” asked Caroline as she reached back with both hands to spread her toned ass cheeks apart.

 

It was her friend Jess that took the lead and slowly pulled out the large plug that measured 3.5” wide at its largest part; by no means her biggest, but certainly filling for everyday use.

 

All the girls watched on as the plug slowly stretched out her sphincter before it finely popped out and her asshole did its best to return to its usual elongated semi-closed position; it’d been years since Caroline’s asshole had been able to truly close.  By now the ever present lube had been brought out and was being liberally and lovingly applied to Caroline’s anus by Jodie.  Her fingers easily slid in and out of Caroline’s stretched out hole as she applied the slick lubricant with four fingers.  It wasn’t long before she had slipped her thumb in and her whole fist had disappeared up Caroline’s delicious backside.  The small teenage fist went in almost too easily.

 

Caroline looked back at Jodie with a look of open mouthed ecstasy as her friend started to slowly and rhythmically fist her best friend’s ass, going deeper with each thrust.  It wasn’t long before her friend Amy laid a soft kiss on Caroline’s lips that quickly turned into deep erotic French kissing.  Caroline loved to make out with her friends in their ass play sessions, which would usually involve lots of kissing.

 

All the girls crowded round gently stroking and caressing Caroline’s body, loving the sight of her distended anus being stretched beyond belief.  Amy gently stroked Caroline’s pretty hair telling her what a sexy bum slut she was.  After five minutes of relentless pounding by Jodie, Mandy took over and was soon forearm deep in an overjoyed Caroline’s ass.  After another five minutes or so of continuous fisting, Mandy’s elbow was brushing against Caroline’s anus on each inward stroke. Mandy would pull her arm out until her fist was tugging at Caroline’s loose ass lips, almost but not quite popping out, before she would sink her arm back into the depths of Caroline’s rectum.

 

Jess was next up and picked up where Mandy had left off; sawing her whole arm in and out of Caroline’s dilated bum hole, wrist to elbow on each stroke.  After Jess ran out of steam, Sarah picked up the slack. Sarah usually didn’t go elbow deep on Caroline like the others did. She liked to ball up her first and punch it in and out of Caroline’s now gaping ass and watch the worn out anus try in vain to close itself as it was briefly left unfilled and un-stretched. Caroline, enjoying the different sensation, moaned and gyrated her hips to the rhythm of Sarah’s punching fist.

 

When Sarah eventually tired of punch fucking her friend’s ass, it was finally Amy’s turn to violate Caroline’s lovely bottom. Amy really liked finishing Caroline off so she usually went last. She quickly buried her arm up to the elbow in Caroline’s distended anus without meeting any resistance at all. Once buried to the hilt, Amy began twisting her arm and fist around and bumping her arm forward trying to sink the edge of her elbow up her friend’s gyrating ass. When Caroline was really excited and loose, Amy could actually accomplish this feat; as was the case today. All the girls cheered when Caroline’s slutty bum hole finally closed around the base of Amy’s bicep. All Caroline could do was moan loudly while reaching back with both hands to spread her cheeks as wide as she could.

 

For almost half an hour, Caroline moaned and grunted with pleasure as her friends urged each other on to go harder and deeper. It was a wonderful sight, all the girls crowded round worshipping their friend’s slutty loose bum. By the end of lunch break all the girls had had a turn putting their whole arms up a horny and moaning Caroline’s bum hole; Caroline’s ass was a gaping, sloppy mess. The girls helped clean her up and reinserted a slightly larger 4” butt plug. Whatever plug Caroline started the day off with was usually too small to stay in after their lunchtime get-togethers, so Caroline always carried one or two larger butt plugs in her purse. That way her horny butthole could stay pleasantly stretched all afternoon. They then all headed back to class to finish off the school day.

 

*             *             *

 

When school got out that afternoon Caroline said goodbye to her friends and went to meet up with her waiting mother in the school car park.

 

“Hey, honey! How was school today?” asked Caroline’s mum Susan, as they exchanged their usual mother/daughter kiss – which involved more tongue and ass grabbing than was probably appropriate. Susan was an older version of her daughter, but only grown into her body. Susan could best be described as voluptuous; curves a plenty in all the right places. She was a wet dream for ass-men and breast-men alike. Caroline had some large shoes – and cups – to fill before she grew into her mother’s figure. Finally their inappropriate embrace ended.

 

“Really good, me and my friends had heaps of fun at lunch,” replied Caroline as she got in the car.

 

“I bet you did,” said Caroline’s mum with a knowing smile. “Ready for your appointment with Dr. Michelle, honey?” asked Caroline’s mum.

 

“I’ve been thinking about it all day,” replied Caroline excitedly.

 

Susan always arranged for herself and both her daughters to attend fortnightly ‘consultations’ with Dr. Michelle at a small privately owned clinic that specialized in the treatment of young women. Caroline always looked forward to the appointments and the special anal examinations she would receive.

 

When Caroline and her mother arrived at the clinic, Caroline was still wearing her cute and revealing school uniform. They walked into the clinic holding hands, as was usual for them. After confirming their appointment with Naomi, the pretty and exceptionally well endowed red headed receptionist, Caroline was asked to remove her clothes and take a seat in the waiting room. Caroline loved this part, as taking her clothes off in a public place was one of her favorite things. Her mother helped her strip off her uniform and then folded it in a neat pile.

 

Susan was also required to strip from the waist down as it was the clinic’s standing policy that all patrons have their backsides available for the doctor’s ‘consultations’ if it was required; and it was almost always required. Caroline was treated to a brief glimpse of what she assumed was her mum’s massive butt plug before Susan finished folding her business suit’s slacks and sat down with her. They then waited and chatted softly for Caroline’s name to be called.

 

It wasn’t long before the door opened and an attractive, dominant looking woman wearing a white medical coat exited. Dr. Michelle was very attractive, had an athletic physique, medium sized breasts, jet black hair and was in her early thirties. As she walked, she was talking to an attractive blond woman in her late thirties, and what Caroline assumed was her daughter. The daughter was naked and the mother bare from the waist down, as was to be expected. The daughter was walking slightly bow-legged and was obviously struggling to accommodate something rather large lodged in her bum. Caroline could also see the base of a matching something peeking out from between the blonde mother’s shapely butt cheeks.

 

“Just remember to keep checking Amanda’s plug every night before she goes to bed. If you can force a finger in beside it, she needs to be fitted with a larger one before she goes to sleep. Hopefully, we can get her anal expansion back on schedule again by her next visit,” Dr. Michelle said to the blond mother.

 

“Of course, doctor. I’ll stay on top of her better from now on,” the woman replied.

 

“Glad to hear it; Naomi will take care of the paperwork with your insurance. Oh and Naomi, schedule Mrs. Hill for an appointment of her own later this week; her plug had a lot of slack in it and I’m running too far behind this afternoon to fit her with a properly sized one today,” Mrs. Hill looked slightly taken aback, but nodded her consent to Naomi.

 

“Just a fitting session, doctor? Or should I schedule Mrs. Hill for a stretching session prior to it?” Naomi asked unfazed at the nonchalant discussion of another woman’s anal dilation – such talked was obviously quite common at the clinic. Mrs. Hill turned a light shade of red from the embarrassment of having the stretching and plugging of her most private hole talked about openly in front of her daughter.

 

“I think both would be appropriate, don’t you think, Mrs. Hill?” Amanda’s mother only nodded her head silently in agreement. “That way we can fit you with a more comfortable plug quickly and get you on your way. I know the fear of having a too small butt plug slip out of your anus in public is something no woman should have to worry about!” With that, Dr. Michelle nodded a final time to Naomi and turned her attention to her next patient.

 

“Hello, Caroline!” Dr. Michelle said as she entered the waiting room. “Come this way back to the exam room. How have you been?” she asked as they followed her back.

 

“Really good thanks, Dr. Michelle.” replied Caroline.

 

“Have you been looking after your bottom like a good girl?”

 

“Yes! Every day, doctor,” replied Caroline.

 

“I’m pleased to hear that,” said Dr. Michelle as they entered her examination room and she closed the door behind them. “As you probably overheard, not all of my patients – or their mums – are as proactive as you.” Turning towards Caroline’s mum, “I know I can always count on Mrs. Evans to have an appropriately sized plug filling up her backside, and her daughter can almost always be counted on for the same!”

 

“Why thank you, Dr. Michelle! I for one never want a plug that I’m wearing to slip out in public. I might die from the embarrassment!” Susan replied, giggling slightly.

 

“Why don’t I check you out quickly before we get on to your daughter’s exam. I need to make sure her caregiver is setting the right example.” Susan nodded emphatically in agreement. “Go ahead and have a seat and put your feet in the stirrups… There we go… Now let’s just adjust these stirrups so we can have a good look at you… Ah! Very nice.” Susan was now lying on her back on the exam table with her legs spread wide at a 90 degree angle, with her ankles almost back to the level of her ears. This left Susan’s bald vagina open for the world to see; or at least just Dr. Michelle and Caroline. Susan’s vagina gaped slightly and it was easy to see her moist inner labia. This wasn’t from it being well fucked; it was due to the stretching of the truly massive plug protruding from her backside.

 

And that nether hole was truly well fucked indeed. The women of the Evans household had always been very open about sex, and specifically anal sex in all its varieties. While most girls in high school giggled at hearing the word ‘penis’ in health class, Caroline and her sister Rachel had already known half the Kama Sutra; at least in theory if not in practice. Seeing her mum spread wide open on display like that was nothing new for Caroline, and she leaned in close to get a better look at the latex monster invading her mother’s rear hole.

 

“Alright, let’s see what we have here,” Dr. Michelle said, sitting down at the foot of the table and taking hold of the base of Caroline’s mum’s wide butt stretcher. Dr. Michelle turned the plug clockwise and counterclockwise while pulling outward more and more forcefully. Susan started to moan and then gasp as the plugs widest part neared exiting her body. Susan’s sphincter was pulling farther and farther away from her body the further Dr. Michelle pulled the plug out. Finally, with an audible pop, the plug came free with only a muffled cry from Susan; her abused asshole not even trying to close itself after decades of self inflicted dilation; the poor hole just hung open obscenely.

 

“Ah… The Anal Admiral series of plugs,” Dr. Michelle commented as she tried to wrap both her hands around the circumference of the mammoth plug and failed. “I believe this is the 7” model with the 6.5” neck; very serious hardware. I recommend these to all my advanced butt sluts. I wear a similar model to work, although I prefer a larger one for play.” Caroline gasped, loud enough for Dr. Michelle to hear, at the thought of this professional looking doctor, well respected in her field, showing up to work every day with her anus grossly stretched by 7” of latex.

 

Dr. Michelle only smiled and turned towards Caroline. “You don’t think I would have gotten this far, and with such a lucrative practice, if I didn’t practice what I preached, do you?” she asked. “Before I can recommend women push their bodies to their physical limits, I have to know my own.”

 

“You mean, you’re wearing a 7” butt plug right now?” Caroline asked amazed.

 

Dr. Michelle turned slightly red and lost her dominant aura for a moment as she re-lubricated Susan’s heavy plug and lined it back up with the battered asshole for reinsertion. Susan began to gasp and pant as the 7” bulge once again made another of its frequent trips through her yielding sphincter. “Well, this weekend is my husband’s and my wedding anniversary and we’re going away for a four day weekend, so I figured I’d give him a special present. My husband really loves how tight I am during vaginal intercourse while I’m wearing one of my larger plugs, so I’ve actually been dilating myself more than usual this week in preparation. I’m actually wearing a 7.75” butt plug. I should be up to an 8” plug by the time we take off on Friday.” Dr Michelle looked dreamily at Susan’s plug as it finally slid home in her rectum once again; thinking more of the pain emanating from her own well stretched sphincter than the pain she was inflicting on Susan. Dr. Michelle shook herself back to the present and her dominant aura retuned instantly.

 

“Good job, Mrs. Evans,” she said releasing the tension on the exam table’s stirrups and lowering Susan’s feet to the floor. “Keep up the good work.”

 

“Now, onto the real exam,” Dr. Michelle said and started by asking some routine and mundane medical questions as she always did before she moved on to asking Caroline about the frequency of her bowel movements, flatulence, how often she wore a butt plug, what size and her daily anal hygiene practices. “Ok sweetie, can I get you to hop up on the examination table for me,” she said finally.

 

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.

 

“Got it!” Nurse Kelly sighed with relief and satisfaction at a job well done; knowing that she would have to repeat this stretching treatment in less than 48 hours with an even bigger Anal Admiral in order for her boss to meet her goal in time for her anniversary.

 

Gently, Kelly disengaged the ratchet on the gynecological chair and allowed her boss’s legs to come together at last. Slowly she unstrapped the doctor and helped her to stand on wobbly legs. “Alright, Doctor,” she said reassuringly. “You know the drill. Let’s get you walking so your ass can acclimate.”

 

Even as Kelly began to pull her boss into motion, Dr. Michelle begged, “Just give me a minute to adjust, Nurse Kelly,” and then moaned as the pain from her tortured anal ring shot up her spine as she took her first steps.

 

“Nonsense, Doctor! Didn’t you instruct me just yesterday when our positions were reversed that the best thing for a sphincter’s acclimation is to get the patient walking as soon as possible after insertion of a larger plug?”

 

Dr. Michelle could only nod in defeat as they completed their first lap around her spacious office. She tried her best to be a strong, independent woman about her situation, but couldn’t help sniffling back the occasional tear as the unbelievable pain wracked her well toned, naked body.

 

After half a dozen laps, Dr. Michelle’s sobbing had subsided. Another dozen and she could walk without being hunched over or bowlegged. Soon, her gait was almost back to normal and her usual professional composure was quickly returning.

 

“Thank you, Nurse Kelly,” Dr. Michelle said at last as she broke away from the other woman’s grip and made her way to her wardrobe, now fully in control of herself; despite the reduced pain still pulsing out of her back hole. “Be sure to clean up.”

 

“Yes, Doctor,” replied the nurse as she busied herself with cleaning up the discarded plug and the gynecological chair. By the time the office was back in order, Dr. Michelle was once again fully dressed and every inch the sophisticated medical doctor.

 

“Will there be anything else before I leave, Doctor?” Kelly asked when she had finished refilling the large bottle of extra thick anal lubricant on the cart.

 

“Hmm... Oh yes!” replied the doctor. “When was the last time I checked your plug?”

 

Kelly’s heart dropped. “I believe it was yesterday afternoon, Doctor.”

 

“Yesterday? My, how the time flies,” Dr. Michelle said with an evil grin as she patted the seat of the temporarily vacant chair with her strong hand.

 

Nurse Kelly only sighed. “Yes, Doctor,” she replied as her fingers worked the buttons of her uniform.

 

Dr. Michelle’s smile widened as she slipped her hands and arms into the elbow length latex gloves while Nurse Kelly stripped.

 

*                  *                  *

 

When they arrived home Rachel was there lying back on the couch watching TV; naked from the waist down. One hand was holding her legs out of the way while the other hand was buried up her pert backside as she absentmindedly popped her closed fist in and out of her loose hole. Caroline glanced at the screen long enough to recognize the performance; it was a scene from the family reunion a few months back. She recognized her mother and her Aunt Becky engaged in vigorous anal intercourse. Her mother wore a 6.5” strap-on and was viciously sawing the large dildo in and out of her older sister’s asshole as she lay back on a bed and moaned like a true anal slut.

 

“Hey Rach, look what I got,” said an excited Caroline.

 

“Wow that’s huge, do you think you can take all that?” asked her sister, not pausing in her anal masturbation.

 

“Mom’s going to help me do it; can you help too?”

 

“Sure, anything for my little sis,” replied Rachel as Caroline slipped out of her tight little pants.

 

“Now honey, first we’re going to have to get you warmed up, so I want you to go and get an extra large dildo and some lube,” instructed Caroline’s mum as she sat down on the couch next to her oldest daughter. She repositioned the younger woman slightly before removing the fist that had been working the well-used asshole and replacing it with her own. “Becky always did like it rough,” Susan commented as she established a fast pace with her fist. Rachel began moaning more emphatically as she focused her attention on her rock hard nipples now that her mother had taken over the fucking of her ass.

 

Susan smiled and looked down at her oldest as she approached orgasm. After a few moments she glanced at the TV just in time to see her onscreen self and older sister trade places and begin the rough fucking anew. Her smile grew wider, “I guess I always did like it rough too!”

 

It wasn’t long before Caroline returned with a huge rubber dildo and some extra strength anal lube. As she walked back into the room, she saw her mother sitting next to Rachel as she pounded her fist and a good deal of her arm up her older daughter’s dilated anus and rectum. It was only a few seconds before the younger woman exploded in orgasm. Finally, Susan removed her fist from her daughter and re-plugged the gaping bum hole with the 6” plug laying on the couch next to the gasping woman.

 

“Sorry, Caroline,” said her mother apologetically. “Your sister just needed some help. She can play now.”

 

Caroline smiled knowingly at the pair of older women and then removed the rest of her clothes as her mother moved down the couch to give herself some space. She then lay across her mother’s waiting lap. Her mother removed Caroline’s butt plug with a plopping sound and quickly buried her fist up her daughter’s wide open bum hole; while her quickly recovering sister applied plenty of lube to the big nasty toy. Satisfied at the looseness of her daughter’s hole, Susan nodded to Rachel, removed her fist and placed both her hands on Caroline’s butt checks and spread them apart.

 

“Go ahead, honey.”

 

Rachel, using two hands to grip the monster dildo, started to work it into her sister’s well-used rear entrance. She guided it in and out till she had 15” of the dildo sliding and out of Caroline’s ass. Rachel always loved the sight of her sister’s cute little slutty pink hole being stretched wide as she begged for more. After 10 minutes or so of getting her ass stretched Caroline asked, “Can I try the plug now?”

 

“Ok honey, if you think you’re ready.”

 

“I am Mum, I want to feel something really big up my bum.”

 

Rachel slid the dildo from Caroline’s ass and they made their way over to the Impaling-Chair on which they had set the obscenely large butt plug. Susan and Rachel each held one of Caroline’s arms to balance her as she began to sit down onto the tip of the plug. She continued to push down as it got wider and wider, the strain on her face began to show as she bit down on her lip and pushed harder.

 

“That it sweetheart, keep going... take it all in,” encouraged her mother.

 

“Good work, Caroline, it’s almost in, you’re doing really well,” said her sister urging Caroline on.

 

“Mmm... it’s so big, but I know I can do it,” huffed Caroline.

 

Her mum and sister started to gently force her down onto the chair, as Caroline looked up at her mother with an open-mouthed expression and glazed-over eyes, as she could feel her sphincter starting to be stretched to breaking point.

 

“Almost there darling just a little bit more,” soothingly reassured her mother as they forced her down to the very widest part of the plug.

 

Just as she felt she was stretched to her limit the plug slipped into her ass and her backside sat down fully on the chair as her sphincter came to rest around the 5” stem of the plug. She sat there on the chair crying softly and tried to adjust to the size of the object nestled in her rectum.

 

“Wow, Caroline, how does it feel?” asked her sister.

 

“It... it’s good, I feel so full and stuffed back there,” stammered a breathless Caroline.

 

“I would imagine!” exclaimed Susan. “That’s the largest toy you’ve ever worn!”

 

“I’m so proud of my baby sister,” said Rachel as she leaned over and kissed Caroline deeply.

 

Susan bent down and flipped the lever on the Impaling-Chair to release the plug and allow Caroline to stand up. “Why don’t you sit down on the couch and watch some TV and get used to your new toy?”

 

“Okay, Mom,” replied Caroline as she gingerly stood up and slowly waddled over to the couch. Susan followed her youngest daughter to ensure she made it safely. Having such a relatively large slab of latex up a girl’s butt for the first time could be disorienting.

 

The family reunion video was still playing. Susan’s onscreen self was moaning wildly at the camera as her sister Becky worked bother her fists and forearms into her younger sister’s quivering anus. Susan smiled at the memory of the annual family reunion.

 

“Now, you just sit here and watch mommy play with Aunt Becky for a while. I’m going to go get cleaned up for dinner.”

 

“Okay,” was all Caroline responded as she struggled to find a comfortable position on the couch.

 

“Need a hand, mom?” Rachel asked hopefully.

 

“Oh, probably, Rach,” replied Susan. Her oldest was always so willing to help her mother out anally. “But don’t you have a date tonight?” she asked as she headed to the back of the house and her bedroom.

 

“Sure do. I need to head out pretty quickly, but I have a few free minutes to help you out,” answered Rachel as she followed her mum; admiring the sexy sway of the older woman’s hips and butt as she did.

 

As the pair entered the master bedroom, Susan kicked off her high heels, unbuckled her belt and let her suit pants slip off her hips and onto the floor. Stripped from the waist down, the busty mother of two turned towards her waiting oldest daughter and pulled her in for a long, deep kiss. The kiss lingered for several seconds before Susan broke off and sat down on her bed.

 

“You’ve always been such a helpful girl, Rachel,” Susan said as she lay backwards and pulled her legs up to her chest.

 

“I try, mom,” Rachel replied as she squatted at the foot of the bed to admire the thick disk of black latex splitting her mother’s full ass cheeks. “Is this your 6.5” plug?” she asked absentmindedly as she grasped its base and began to pull outwards. She loved the look of her mother’s anus as it was pulled outwards away from her body.

 

“No, honey. It’s my normal 7” daily plug,” Susan responded as she began to groan at the pain from her straining sphincter. “I’m afraid a 6.5” plug would probably slip right out before lunch.”

 

“Well, we wouldn’t want that!” exclaimed Rachel as her mother’s anus continued to expand to allow the huge plug to slide past.

 

It took a minute or two, but finally the large plug slipped free from Susan’s distended anus for the second time in less than two hours. Susan let out a gasp and a muted cry of pain as the widest part popped past her abused asshole. It took her only a moment to regain her composure before she said, “Thank you, honey. Just put it with the set; I’ll clean it in a few minutes.”

 

“Sure, mom,” Rachel said as she stool, walked over to the chest of drawers and placed the used and slightly dirty plug in line with its brothers. The set of plugs was lined up from smallest to largest – 6” to 9” at quarter inch intervals. It was the full Extra Large Anal Admiral Experience™ set. The smaller plugs hadn’t been used in quite some time, while Susan was still working up to the larger ones.

 

“Alright, mom. I need to head out,” Rachel said, turning from her mother’s array of anal tools.

 

“Have a fun night, honey,” Susan said as she stood up to kiss her oldest daughter goodbye; and cop a feel of her daughter’s fully stuffed ass as she did so. “Should I wait up?”

 

“Probably not. Kristy’s parents are out of town tonight and I’m sleeping over there,” Rachel answered as she broke the kiss and headed for the door.

 

“Well, tell her I said, ‘Hi’ then.”

 

“Will do. Good night, mom!” and with that, Rachel was out of the room.

 

Susan smiled to herself as she unbuttoned her blouse. So it was just her and Caroline tonight then. Too bad that her youngest daughter was probably out of commission for the evening as she acclimated to her new plug; although, that left Susan with a largely free evening. What to do? she thought to herself as she unclasp her bra and allowed her large breasts to be freed at last. Her own back hole yearned for some serious anal play. Dr. Michelle’s talk about obscenely stretching herself for her anniversary had gotten her in a horny mood. Buying that new huge plug for Caroline had only worsened her condition. Coming home to her eldest masturbating to the video of her mother and aunt buggering each other had made Susan horny beyond belief.

 

What to do?

 

Her eyes looked around the room and came to rest on the plugs, and a smile crept across her face. “Fuck it!” she said out loud and crossed to her waiting toys. “If Dr. Michelle and Caroline are pushing their anal limits, I guess I might as well too,” she continued as she crossed the room and picked up the imposing 8” rectal plug. She’d worn this plug in the past, but it was over a year ago and it had been excruciating! “Do I really want this massive slab of black latex in my nether hole tonight?”

 

She glanced down at the plug in her hands and was half surprised to see her hands already absentmindedly lubricating the terrible toy. She laughed softly to herself, “I guess so!”

 

Susan stepped over to her Impaling-Chair and attached the well lubricated dong onto the waiting stud. Squatting down, she lined up the tip of the plug with her still gaping hole and began lowering her body. Susan gasped as her anus slipped down to – what she guessed to be – the 7” wide part of the plug’s massive girth. As she relaxed her legs so that her full weight came down onto her straining sphincter, she asked herself, “Whose dumb idea was this anyway?” She steadied herself as she lifted first one foot and then the other onto the chair’s foot rests. All she had to do was sit back, relax, and let gravity do its work.

 

Susan gasped painfully as she felt her body slip farther and farther down onto the huge plug underneath her ass. She had to wipe her forehead as sweat trickled into her eyes at the strain in her body. “Fuck!” she cried out. “It looks like both Caroline and I will be hanging out on the couch tonight acclimating to our new plugs. It should be good mother/daughter bonding time”, she thought encouragingly to herself.

 

The minutes ticked by and Susan sunk lower and lower. The pain was almost unbearable, but she gritted her teeth and bore through it. Finally her heart jumped into her throat as she unexpectedly fell a few inches and her butt slammed down onto the Impaling-Chair’s seat. Stars flew in front of Susan’s eye for a solid heartbeat; then two; and then she screamed in blood curdling pain, “Oh fuck!”

 

A second later, Caroline’s concerned voice came from living room, “Are you okay, mom?”

 

“Yes, honey!” Susan replied as she put her feet on the ground and disengaged her plug from the chair. She stood slowly; her head spinning from the pain in her violated rectum.

 

Well, this is going to be an interesting night, Susan thought to herself as she slowly waddled out of the bedroom towards the living room. Two naked, horny women sitting on a couch watching homemade incest pornography, and unable to do anything about it!

 

Whose dumb idea was this anyway?

[colmtzar]

Common... more pliz!

[NoRefundUK]

Superb. As always, looking forward to seeing more from you guys.

 

It's a shame that Jason doesn't write more.

[Rubbish]

Thanks for Caroline with her big ass hole,nice story.