Caroline the Teenage Bum Slut

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Blowjob

Caroline the Teenage Bum Slut (Redux — Chapter 1)

Originally by: Jason Hitchcock

Adapted by: LordOdie & FantasyWriter1

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 canlı bahis 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 bahis siteleri 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! bahis şirketleri 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.

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