Anal ruin

anet was a cute girl, 20 years old. She had long dark hair, a bit more than average sized breasts and was about 5 feet, 6 inches.
When she was 15 she discovered the pleasure of inserting objects into her pussy and ass. It all started with curiosity, some candles, cucumbers, apples. At the age of 18 she had her first boyfriend who acknowledged her skills and well-trained holes and started to teach her how to take a man's fist in the ass. It took about 3 months but he finally managed to get his whole hand into her. About a year later she could take his fist with ease - her bottom hole being permanently stretched could swallow a hand with just a little spit for lubrication. The unfortunate event of him dumping her kind of hijacked her daily training regime. She had everything inserted into her which she could possibly find so it was time for her to move on, to look for more.

As usual on Sunday mornings she was reading a newspaper as her glance fell onto an unusal ad:

Rich lady looking for a new maid. She needs to know how to hand-le "things". Move-in to household required. Monthly payment of $5000. Applicants to be interviewed next Wednesday. Call 555-555-1678.

"Sounds like fun", she thought and called the number to make an appointment...


Part 2
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Janet arrived at the mansion. A young woman in a maid outfit opened the door. "You must be Janet", she said, "come in, the lady is already waiting for you." She went ahead. Janet noticed a chain dangling between her legs, barely visible under the skirt. She followed her into a large room. Behind a wooden desk sat an elegant lady, probably in her 40s. She introduced herself as Miss M and was apparently gravitated towards Janet. Both agreed on the terms and conditions and M told her that she would stay and Janet's luggage would be picked up by M's chauffeur later on. M led her way into the mansion's kitchen.

She seemed to have a huge butt, unusually huge for her slim figure. She wore a blouse and a long skirt.
"I'll show you what we have planned for you. And you know... the apprentice is expected to outperform her master", she told Janet.
Then she slowly lifted her skirt. Janet sniffed. There was a slight smell of ass in the air. She couldn't quite figure out where it came from until she saw what was under Miss M's skirt. The first time in her life Janet was really shocked. M's ass could not be called an ass anymore. It was like a ball of flesh hanging between her buttocks which was somehow fastened with a slim black nylon rope. M sat down and started to untie the rope. Now Janet could see that metal rings had been inserted into M's ass lips resembling the holes in lace-up shoes. The ass lips were huge curtains of flesh, probably hanging down 4 inches. As she removed the rope from the last hole her ass flesh started to bulge and red swollen ass meat prolapsed out of her hole. It emerged about 5 inches and then came to a rest, ass juice dripping to the floor. The torn hole was gaping almost 5 inches in diameter.
"See", M said, "I have to keep my guts in somehow. That's what the rope and holes are for."
Then she took a magnum bottle of champagne, put it on the floor and lowered her ass down onto its neck. The more of the bottle disappeared in her hole the more flesh of her prolapse was pressed back into her ass where it belonged. She did not have to use much f***e. M just kept lowering herself towards the floor. Finally, the bottom of the bottle passed her rim and the ass lips rested on the ground, leaving a slimy mark. She stood up, pulling her legs together, the bottle deeply embedded in her bowels.
"That's fun", she said, "but the problem is that such ass dilation results in a loss of muscle power... CATCH IT."
M opened her legs and Janet rushed towards her. The prolapse fell out with a loud plop, the bottle still halfway embedded. Slowly it started to ooze out into Janet's open hands.

With a dirty smirk she said, "I crave the feeling of fullness. Get me that watermelon from the shelf."
Janet took the melon and placed it on the ground. M walked over it and bent her knees.
"Pull my ass lips open with your hands, Janet", M said. M herself grabbed the front lips just below her pussy while Janet grabbed the back lips. When they were stretched almost to the point of tearing, M dropped f***efully onto the watermelon, screaming loudly as it entered her with great f***e, moving into her guts and pressing against her lungs, almost knocking her out.
Panting heavily she told Janet to hold the melon in while she lay down on her back, bending over so that her feet rested next to her head. The melon sunk deeper, about an inch still protruding from her ass.
"Now lace it up", she instructed Janet. Janet took the black nylon rope and laced it through the metal holes in M's ass lips.
"Thighten it up, we don't want to loose anything, do we." Janet pulled as hard as she could to lace the lips together, pulling them over the top of the melon.
Awkwardly M got onto her feet. Janet expected her to have a lot of problems walking but apparently M was used to such abuse. She could walk pretty well, the ball of flesh and fruit between her legs hanging halfway down to her knees. She pulled down her skirt and said, "come on, I'll introduce you to your new colleagues."


Part 3
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M rang a bell. Seconds later the maid appeared who had opened the door to let Janet in.
"This is Cindy. Come on, show our guest what is so special about you."
Slowly Cindy unbuttoned her skirt and removed it. Her pussy was nicely shaven. The chain Janet had noticed earlier seemed to dangle out of her pussy. She inserted her slender fingers into her pussy and pulled the lips apart. Shocked, Janet saw that the chain was fastened to a black plug which seemed to be stuck in her peehole. She started to tug gently on the chain, getting a good grip. Then she pulled harder. The plug slowly moved. The more it moved the more her urethral opening dilated. Then, with a plop, the plug was pulled free, leaving a gaping 2 inch hole. Pee gushed out of it, then slowed down to a continuous trickle. She pulled open the flesh and Janet could see directly into her bladder. The internal sphincter responsible for holding back the urine was barely visible. All what remained was a red ring of torn flesh, rendering her permanently incontinent.
"Cindy enjoys urethral intercourse. The bigger the better. In fact, her G-spot is located unusually deep within the mucuous membranes of her vagina. It's just much easier to get to it from the 'other' side. That's why she doesn't enjoy vanilla sex as much as we might do. Let me show you something."
Miss M opened a drawer and pulled out a flesh colored strap-on dildo about 8 inches in length and 1.5 inches in diameter. She fastened it to her hips and dipped the tip of it in a jar of vaseline. Then she approached Cindy who was now sitting on the edge of a table. M directed the dildo into her peehole and slowly leaned forward. Cindy made a hissing noise and started to smile as the dildo hit her G-spot. Deeper and deeper M pressed until the dildo was fully embedded into Cindy's bladder. Then she withdrew in a fast motion, plopping free. Without any more blockage, urine started leaking out of Cindy's hole. M repeated this several times until she could penetrate Cindy with ease. Then she really started to work on her, pulling all the way out, pushing all the way in. The melon-flesh ball between M's legs dangled forward and backward, stretching the skin of her ass lips more and more. Even the tight rope could not prevent some ass juice to leak out of M's humonguous hole as it was loosened by all the motion. Slime started to drip down onto her legs and a puddle formed on the ground.
Meanwhile the dildo slid in and out with ease, sometimes causing splashs of pee driven out of Cindy's peehole with all that drilling action. After 5 minutes Cindy had an earth-shattering orgasm, cramping for several minutes and almost became u*********s. M slowly withdrew the strap-on. Streaks of slime and bl**d covered it from tip to base.
"We have to plug the mess. Get me that box over there", she said to Janet. Janet gave the box to M who opened it and took out 5 large sized tampons. One by one she pushed them into Cindy's bl**dy pisshole until all had been inserted. 5 strings dangled between her legs.
"She'll be fine, she's used to that.", was all what M had to say about it.
Cindy grabbed the skirt from the ground and started to dress. With wobbly legs and a big smile on her face she walked towards the bathroom to clean her legs, wash away all the piss, slime and bl**d.


Part 4
------

M hurried out of the room, "Let's move on to your next colleague. May I introduce you to Celine, our kitchen maid."
Celine was busy cleaning the kitchen. She turned around as Janet approached her. Janet gasped in awe. Celine was a slim brunette with what must be the biggest tits she has ever seen. They looked like the watermelon M still had tightly secured within the depths of her bowels.
"Not only is she responsible for buying our fruit, making sure we always have some nice melons here. She also provides us with a daily glass of fresh milk. C'mon dear, show Janet what you got.", M insisted.
Celine unbuttoned her blouse, exposing her monster boobs. Janet stepped closer to observe the amazing sight. The tits themselves looked like marble, blue veins showing slightly below the flesh. At the base each breast had been pulled through 3 consecutive plastic rings, each about 1 inch in width and 4 inches in diameter, thus reducing her breasts to 3 inch long tubes. The remaining breast sat on top of that flesh tube, looking like a ball of flesh on a vase. Each nipple was a dark red meat, resembling a tiny finger. They were about 2 inches in length. Looking closer, Janet saw that each nipple had a tiny plug inserted.
Celine grabbed the left nipple with her left hand and started to turn the plug with her right hand. Apparently the plug was a screw securely tightened in her nipple. It's counterpart, a nut, was embedded in the flesh of the nipple. When she had the nipple fully unplugged, milk started to ooze out of the hole. She took a glass from the table and filled it to the brim, handing it over to M. M took a sip and gave it to Janet. "Try it, nothing's better then a glass of breast milk on a hot summer day." Janet tasted some and it was not so bad after all. Meanwhile Celine screwed the plug back into her nipple and wiped the residue milk from her breasts. Then she buttoned up her blouse again and resumed her cleaning duties.


Part 5
------

Next they moved on to the living room. A maid was cleaning a wooden desk. She wore a tight latex skirt and above the skirt her huge belly was visible. Apparently she was 9 months pregnant.
"Carla, turn around and lift your skirt.", said M. Carla pulled her skirt up. Janet could see her grotesquely stretched pussy with the mouth of her womb protruding out of her like 2 inches. A pale beige colored thing was clearly visible, stuck in her womb.
"Carla is not pregnant as you might have guessed. Instead she's training her womb with an inflatable balloon. I think it's about time to finish her training for today.", M explained. They led Carla into a room in the basement. The room looked like a mixture of torture chamber and medical laboratory. In the middle of the room was a gyn table. Holding her huge belly with both hands, Carla stepped carefully onto the table and put her legs in the stirrups.
M inserted the fingers of her right hand into Carlas pussy and womb, twisting and turning the balloon until a valve became visible. She opened the valve and air hissed out of the balloon. Janet could see how her belly deflated, leaving stretch marks on her skin. As all air had been removed, M tugged on the balloon and slowly pulled it free. Being massively stretched for such a long time, her whole womb was a prolapsing mess.
"We need to take care of her prolapse.", M continued to explain while she opened a drawer and grabbed another balloon which seemed to be covered in some sort of mesh.
"See, this mesh is the same material surgeons use to suture wounds and after some days it is absorbed by the body and disappears. The mesh will stabilize her cunt walls and push her womb back where it belongs. Our material here will last about 20 days. Then her next training is due. We will fix the mesh in place with a special glue.", she said as she applied the glue liberally onto the mesh balloon.
Then M inserted a huge horse speculum into Carla's pussy and dilated her to the max. She pushed the womb back in with her hand and then inserted the balloon, making sure it rested just below her womb. Then she removed the speculum and proceeded to inflate the balloon until it was fully inserted and started to bulge. They waited 10 minutes until the glue was hardened and the mesh fixed in place. M deflated the balloon and pulled it out of her cunt.
Amazingly, it worked. The womb did not prolapse anymore and the only thing that remained Carla of her training was a huge gaping pussy and the stretchmarks on her belly.
"Get up and out of here, Carla. Janet, you and I... we will take care of your luggage now... and mine."


Part 6
------

They went to the front door and saw an expensive looking black car arriving. The door opened and a huge man in his 30s slowly emerged from the driver's seat. He wore a black suit and had a shaved head.
"That's Igor, my driver.", M cared to explain while Igor opened the trunk and started to carry Janet's luggage into the mansion. With the last piece of it finally in Janet's new room, M led both of them back to the room in the basement.
M requested Igor to strip. He removed his suit and stood there in latex-like underwear.
"These are special pants, custom-built to keep him well dilated while he is on duty."
She pulled down a bit of the back side. Janet could see that his ass was obscenely dilated around a huge rubber ball thing which was molded to the pants. In fact, it looked like it all was one piece. Then she pulled at the front, exposing the fattest 10 inch cock Janet has ever seen. His urethra was dilated about half an inch and filled with a rubber dildo connected to the pants.
"Actually, we filled his ass and cock with liquid latex and used it for building his pants. It fits exactly in his holes and fills him to maximum capacity.", explained M.
She started to pull the front part out of his urethra. He moaned with pleasure as it finally popped free, followed by a mix of lube and precum. His pisshole gaped and didn't dare to close. It was surrounded by a quarter inch of cock flesh. Then she requested him to push with all his strength, meanwhile pulling at his stuffed backside. It took about 20 minutes until she finally managed to pull it free. What came out was a strange looking curvy object with irregular diameter, probably ranging from 4 to 8 inches in diameter with a length of 10 inches. It resembled the bends of his colon.
Janet could now see that he had the same metal-enf***ed holes in his ass lips as M. Needless to say that his guts prolapsed out of his ass cave as well.

Igor stepped onto the gyn table and put his feet into the stirrups. M mentioned that pain should be combined with pleasure. She opened a closet at the wall and what became visibile was a huge tank of StarLube with a hose connected to it. She pushed the nozzle into the peehole of his soft cock and pressed a button. StarLube was filled into his cock to the brim. M withdrew the nozzle and picked something from a drawer. It looked like a Van Buren sound with a curved end. But it was hollow, like a tube. It was 10 inches in length up to the curve and then had 1 more inches after the bend, pointing inwards.
"The problem with these curved sounds is that they can only be inserted into a soft cock because of the curved tip. Same goes for removal. So we have to be fast because our Igor is quickly stimulated and will grow."
She grabbed his cock and quickly inserted the tip of the tube in his still gaping peehole. His cock bent at an almost 90 degree angle as she shoved the tube deeper into his urethra, twisting and turning it to keep it moving.
Finally, it slipped into place, the tip positioned directly behind his prostate. The other end of the tube was protuding 1 inch visibly from his cock but slowly disappeared as his erection grew.
When it was fully erect, the opening of the tube disappeared in his cockhead. She stroked his dick, bending it left and right to manipulate his prostate. A whitish fluid began leaking out of the tubed cock.
"Cock milk I call it. Now let's get rid of my luggage."

M strapped his feet and arms tight and a lever and a machinery rotated the gyn table so that Igor hung in the stirrups heads down, his ass pointing towards the ceiling.
M untightened the nylon rope holding her ass lips together and stepped onto the table as well. She positioned her ass directly over his. Now Janet grasped what M meant earlier with taking care of her luggage. The melon started to f***e its way out, f***ed by gravity. However, it got stuck after 2 inches.
"Janet, come over here. Unfortunately, I don't have any muscle power left to push and gravity alone won't do. Take the snap-hooks from the drawer and connect our asses, then attach the chains to the hooks and pull."
Janet took the hooks from the drawer. Then she pushed the melon back in a bit so she could get access to the metal rings. Ring by ring she first inserted the snap-hook into one of M's holes, then one of Igor's holes. She counted a total of 10 holes. Then she attached 5 metal chains to the hooks, one in every other hole. She gave M and Igor each two of the chains so they could pull them with their hands, then took the remaining chain in her own and started to pull. They pulled with all their strength, the flesh almost tearing apart. But slowly the melon started to sink down. At its widest point it stuck a little but M rocked slightly back and forth, jumping a little up and down and finally... her scream of relief mixed with his scream of pain as the melon transfered from her ass into his. The red swollen walls of his colon covered most of the fruit. Janet un-hooked the chains and then the ass lips and M stepped down from the table, leaving a gooey trail of ass slime behind her. M turned around and laced his ass shut with the nylon rope she had used for herself. Then she turned the lever again, rotating the gyn table back in place. Igor was now dripping precum fluid constantly, the huge melon pressed hard against his prostate and the Van Buren tube in his cock. He was unfastened and then he grabbed his pants and rushed out of the room.

M rang a bell and stepped back onto the table.
Cindy came into the room, the strings of the 5 tampons in her pisshole still visible between her legs.
"Now it's time for my daily cleaning routine", Janet was told by Miss M.
Cindy connected a shower head to a hose at the wall. The shower head was one of these huge massage heads. She inserted it into M's ass, no resistance at all. Then she turned on the hose and a gush of warm water went into her bowels and then leaked out again. After 10 minutes of gut flushing Cindy extracted the shower head from M's ass.
Then she grabbed a small bar of soap and pushed her clenched fist into M's ass up to the elbow. She slowly removed her fist. It came free and Janet was amazed to see that the soap was gone, deeply hidden in her bowels. Cindy took a thing from another drawer which resembled a toilet brush. Only it had much softer bristles and some kind of connector at the handle. She inserted the brush until the handle almost disappeared in her hole and started to massage M's bowels. Remnants of the shower enema mixed with soapy bubbles spurted out of M's ass, dripping along her flappy ass lips to form a puddle on the ground. Cindy pulled over a cart with a piston and connected it to the handle of the brush. Then she started the machine which slowly removed the brush until it rested just at the entrace of her ass and then slowly pushed it back in until the handle disappeared. Cindy turned a knob which increased the speed of the piston. Soap foam was gushing out of M's ass constantly as the piston rammed back and forth into her for about 10 minutes. As the soap gushing stopped, Cindy turned off the piston and extracted the brush from the colon.
As the brush exited M's ass it started spasming from all the workout, prolapsing almost 10 inches, retracting again, prolapsing...
After her guts calmed down, M took the a fresh nylon rope and tied her ass lips back together, then she stood up and told Janet, "I guess now it's your turn. Get a good sl**p, we'll start to work on you tomorrow. You'll be my master piece. I've needed several years to make my maids the way they are. With all my experience and improvements along the process it should take about a year to turn you into a Cindy-Celina-Carla-M."

100% (16/0)
 
Categories: AnalBDSMTaboo
Posted by fighttheupwright
1 year ago    Views: 4,018
Comments (6)
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12 days ago
And I thought I was dirty! I have always fantasized of huge prolapsed assholes feet long
3 months ago
MOST EVER AMAZING HISTORY ON EARTH
4 months ago
Kind of story we love, thanks for sharing
5 months ago
Wow..I felt my ass throb of desire .. already read this story several times ...
10 months ago
interesting read
10 months ago
Great story! Thanks for taking the time to share it!