Caroline the Teenage Bum Slut

It was hard to deny, 16 and half 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 girls 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 fist's and other large objects buried deep inside her favourite body part, her loose 'often obscenely stretched' bumhole.

"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 of 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 round perky teenaged breasts and just a 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 fantasied 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 buttplug, 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 as just 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 favourite position, lying on her stomach with her bottom invitingly poking into air. Jodie started the days fun by slowly peeling down her friends Lycra pants to reveal her glorious bum cheeks between which lay a large black buttplug.

"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 up?" beckoned Caroline.

It was her friend Jess that took the lead and slowly pulled out the large plug that measured 3.5" wide at it's largest part, not 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. 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 backside.

Caroline looked back at Jodie with a look of open mouthed ecstasy as her friend started to slowly and rhythmically fist her best friends ass. 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 pounding by Jodie, Amy took over and was soon wrist deep in an overjoyed Caroline's ass. 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 friends slutty loose bum.

By the end of lunch break all the girls had a turn putting their whole hands up a hornily moaning Caroline's bumhole. When it was all over her ass was a gaping sloppy mess, the girls cleaned her up and reinserted her buttplug, 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 carpark.

"Hey honey, how was school?" asked Caroline's mum Susan, as they exchanged their usual mother daughter kiss as Caroline got in the car.

"Really good, me and my friends had heaps of fun at lunch." replied Caroline.

"I bet you did," said Caroline's mum with a knowing smile.

"Ready for your appointment with Dr. Michelle, hon?" asked Caroline's mum.

"I've been thinking about it all day," replied Caroline.

Susan always arranged for Caroline to attend fortnightly 'consultations' with Dr. Michelle at a small privately owned clinic that specialised in the treatment of teenaged girls. Caroline always looked forward to the appointments and the special anal examinations she would receive. Caroline and her mother arrived at the clinic, Caroline 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, the pretty middled aged receptionist asked Caroline 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 favourite things. Her mother helped her strip off her uniform and then folded it in a neat pile as they sat down and waited.

It wasn't long before they were both greeted by an attractive dominant looking women in her early thirties wearing a white medical coat.

"Hi Caroline, how have you been?" asked Dr. Michelle as they followed her back to the examination room.

"Really good thanks Dr. Michelle." replied Caroline.

"Have you been looking after your bottom?"

"Yes, everyday 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.

The Doctor 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 buttplug and her daily anal hygiene practices.

"Ok sweety, can I get you to hop up on the examination table for me," said Dr. Michelle.

Caroline loved this part as her mother helped her hop up onto the examination table and assume her usual position with her face and chest flat on the soft padding of the table with her back arched and backside pointing up into the air.

"That's a good girl," softly said her mother as she stroked her cheek and caressed her backside.

Dr. Michelle meanwhile pulled on a long surgical rubber glove that reached up to 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 plug was slowly and delicately removed from her behind.

Once the plug had been removed Caroline's mother pulled open her daughters cheeks as her anus opened ready to be filled again.

"Ok Caroline are you ready for your anal examination?" asked the doctor.

Caroline nodded as she looked back 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.

The fisting continued for a full fifteen minutes as the Doctor got deeper and deeper inside Caroline's bumhole, exploring every inch of her back passage with her fist. 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 fist from Caroline's anus, she was a sweating exhausted mass with a wide satisfied grin across her face. Both women looked on delighted and satisfied at the sight of Caroline's wide gaping bumhole. Caroline's buttplug was then reinserted and Caroline was helped to her shaky feet and redressed. They both thanked the Doctor for her time and booked her next appointment.

"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 Icecream 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 daughters 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, buttplug's, stimulator's 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 favourite 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 16 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, till 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 buttplug that measured 5.5" in diameter at it largest part.

"Are you sure, I don't want you to be disappointed if it's to 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 your 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 19 year old sister Rachel and herself. Although Rachel didn't spend much time at home these days as she had a boyfriend, 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 sitting on the couch watching TV.

"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.

"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 and sat on her sisters lap, as she loved to do.

"Now honey, first where going to have to get you warmed up, so I want you to go and get a large dildo and some lube." said Caroline's mum.

It wasn't long before Caroline returned with a huge rubber dildo and some extra strength anal lube.

Caroline then removed the rest of her clothes and lay across her mothers waiting lap, her mother removed Caroline's buttplug with a plopping sound and parted her daughters bum cheeks while her sister applied plenty of lube to the big nasty toy.

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 9 inches of the dildo sliding and out of Caroline's ass. Rachel always loved the sight of her sisters 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 your 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 buttplug 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, your 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 4 " 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.

Caroline awoke the next morning to the gentle shaking of her mother's hand.

"Morning sweetheart, how did you sleep?"

"Mmm ... really good mum," replied a yawning Caroline.

"Ready to take out your plug, so you can freshen up?" asked her mother.

"Yes please," replied Caroline, as she turned onto her stomach while her mother pulled down her covers to reveal the huge black buttplug still nestled firmly between her daughters stunning round globes.

Caroline sleepily raised her backside into the air and rested on her knees. Her mother using two hands slowly began to pull on the huge plug as Caroline's sphincter began to stretch out and become distended. It didn't take long for the plug to slide out, as her asshole had become extremely pliable and loose from being so massively stretched all night. Caroline couldn't help but feel empty as her red swollen anus hung there wide open waiting to be filled again, she loved the feeling of having such a loose ass, it made her feel so naughty and sexy.

Caroline's mother couldn't resist running her finger around the inside of her daughters gaping rectum as Caroline looked back over her shoulder and smiled, enjoying her mothers gentle and loving touch.

"Can we play a bit please mum?" asked Caroline, in the mood for one of her morning fistings.

"Sorry honey, I'm in a bit of a rush this morning but we can have a nice warm soapy shower together if you'd like."

"Looking forward to your sleepover tonight, honey?" asked Caroline's mother as she lovingly scrubbed and soaped her daughters firm young body in the shower.

"I can hardly wait mum, I'm so horny already, Jodie promised me I won't be able to sit down for a week after tonight."

"Lucky you sweety, I'm sure you will be a good girl and take everything they stuff in this little thing," said her mother, as she focused on cleaning her daughters asshole, which was no longer a hole but more like a two inch long vertical slit

After the shower Caroline's mum helped her pick out an insert a buttplug for the day, before they both got dressed a headed out.

Friday's were casual dress day at Caroline's high school and Caroline looked cute as a button when she arrived at school wearing an ultra short light blue polka dotted summer dress and her favourite head band with a pretty pink bow on it. The cutest part though was the pair of tight white cotton panties that were just visible out the bottom of her ultra short hem line. Caroline felt so slutty dressed this way and did her best to bend over at every occasion to give some lucky girls a good look at her tight panty clad behind.

The first couple of classes dragged on as Caroline did her best to entertain herself by flirtatiously playing footsie under the desk with a pretty girl sitting across from her. By third period she was getting really horny and decided to hitch her dress up around her waist and show off her panties to all the girls sitting nearby. When the bell rang for lunch, her third period teacher Ms. Barker asked her to stay behind to have a word. Caroline wasn't sure what this was about and wondered if her flashing had gotten her in trouble.

"Don't worry Caroline your not in trouble or anything," said a kind voiced Miss Barker, much to Caroline's relief.

"The principal has asked to see you in her office."

"Right now?" asked Caroline.

"Yes please Caroline, she is expecting you."

Although Miss Barker had told her she was not in trouble, she couldn't help but feel slightly nervous at the prospect of having to go to the principals office like a naughty girl.

"I can walk with you if you'd like Caroline," said Miss Barker.

"Yes please Miss ... would you mind if I maybe held your hand?" asked Caroline innocently.

"Um ... I guess that should be ok," answered the slightly flustered teacher at the unusual request.

With that Miss Barker took Caroline by the hand and they walked through the school. Caroline loved the looks they got as she walked with her fingers interlaced with the slightly embarrassed teacher. They walked into the school office together and Miss Barker led her down the hallway to the school principal 'Ms. Schmeer's' office. Miss Barker lightly tapped on the partly opened door as Ms. Schmeer looked up from her desk.

"Caroline is here to see you Ms. Schmeer."

"Thank you Miss Barker, that will be all. Caroline, please come in and close the door behind you," said Ms. Schmeer, in her sweet but domineering voice.

Caroline did as she was instructed and walked to the middle of the room where she stood with her legs pressed tightly together and her hands clasped in front of her. She looked so cute and innocent standing there, but Ms. Schmeer knew what a dirty girl she really was.

Ms. Schmeer was a strict disciplinarian in her mid thirties with shiny black hair cut straight at her shoulders and forehead and always wore lots of glossy makeup that seemed to make her skin shimmer. She completed her intimidating authoritarian look by always dressing in tight business skirts and jackets that accentuated and hugged her hourglass figure.

"Remove your panties for me please, Caroline," said Ms. Schmeer matter of factly, taking Caroline aback at first, but she didn't need convincing and began sliding them down her smooth toned legs.

"Good girl, now put them on my desk please," Caroline stepped forward and did as she was told.