Caroline the Teenage Bum Slut

"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?