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Sex games

Breaking Gertrude

Author: lenop

Date: 10 July 2026

Body modification, Anal, Cruelty, Extreme

  • Font:

Картинка к рассказу

Gertrude was a young and beautiful 20 year old woman. On the outside she seemed normal. She was medium height and very slim. She didn't like to wear clothes which attract too much attention. Her usual wear was jeans and loose t-shirts which were hiding her perky firm tits. In a few words, she was attractive, but she would not stand out in a crowd. That's why it was hard to believe that she was hiding a dark secret. She liked pain.

Gertrude was hesitant for a few months but when she finally decided to apply on the add she was alone at home.

Her hands were trembling a bit when she took her phone, but anyway she turned on the camera and positioned it carefully leaning against a few books in front of her bed. Then she undressed in front of the camera, squatted and started masturbating. After a while Gertrude lifted her left tit with her other hand and bit on her nipple as she started cumming. The pleasure took over her body and released whatever liquid was available in her bladder making her piss on her hand which was still rubbing her clit. Once it was over she leaned forward and stopped the recording.

Still naked, standing in the middle of her bedroom she finally sent the video.

...

The approval came on the next day and found her in the shopping mall. When she started reading the message she got a weird feeling of anticipation in her stomach. By the time she finished reading the list of things that are going to be done on her and the instructions where to go, she could feel her cunt getting wetter and wetter. She immidately sneaked inside the closest changing room she found and started masturbating. The orgasm shook her so hard and quickly that a single loud groan of pleasure escaped her mouth.

...

The facility looked like an abandoned warehouse. She wondered if she got the address right, but anyway she entered inside. The large hall was dark and it seemed empty. Chains and different industrial equipment were hanging and laying around making the scene surreal. She made a few steps deeper in the dark. She looked around. Just when she decided that after all it wasn't real and she was probably scammed only to send a video of her masturbating, she felt a sudden movement. A hand appeared from nowhere and pressed a cloth soaked in something on her mouth. Gertrude almost immediately lost consciousness.

...

Gertrude woke up naked. A bright projector light was illuminating her to a point where she couldn't see anything else around. She was hanged in standing position, her arms high in the air chained to a catena of a crane. Her feet were barely touching the ground and there was something on her neck. It felt like a collar and what she could see a small jar was hanging on her chest between her tits. Gertrude wondered what was it. Then the pain hit her. Her body was finally waking up completely from the sedative. She remembered the message and immediately knew what was going on.

"I wanna see" she said to no one, but she had guessed correctly that she wasn't alone.

A hand appeared from the dark holding a small mirror. Because of the bright light Gertrude couldn't see well the owner of the hand, but she gladly looked down when the mirror was positioned her thighs. She gasped.

"I started here." this was a female voice. "First I cut your clitoris at the base." she was pointing with a small knife while explaining "Then I dug a bit with the knife to remove more of the nerve endings." the voice paused for a second and the resumed "Then I continued with the right side. I removed all of the outer and inner cunt lips and then I did the same on the left side. Finished with this I sewed it up completely"

Gertrude was seeing clearly everything in the mirror. The view was gruesome. The hand moved the knife alongside the wound.

"I made sure that the scar will be horrible."

Gertrude was able to understand that. She liked so much to rub her cunt against cocks, objects or simply to masturbate with her hand. All of this was no longer possible. The opening between her legs did not exist anymore. It was sewn shut pretty badly and the cut off pieces of her external genitalia, together with her amputated clitoris were hanging like a medallion in the jar on her chest.

Then it hit her. The first whip. Immediately after that a second one landed on her skin. She gritted her teeth. In the next two minutes more then two dozens of them had scarred her body. The whistling sound of the whip became a rhythm. Gertrude closed her eyes. Subconsciously she tried to anticipate each and every stroke. Suddenly she felt a deep connection with the whip as she tried to expose her body even more. She twisted and moved making sure that the woman whipping won't leave undamaged piece of her body. This ordeal continued almost twenty minutes and stopped only after Getrude passed out, completely hanging on the catena.

...

SPLASH...

SPLASH...

Two buckets of water and Gertrude woke up. Her whole body hurt. Despite the coldness of the water her skin was burning. What felt like thousands of lacerations, were in fact only about a couple of hundred cuts from the whip.

"Wake up!"

SPLASH...

Gertrude was still in shock when the water from the third bucket splashed all over her.

"Oh darling..." the woman pinched Gertrude hardened nipples "Already impatient... huh?"

"What....... for?" Gertrude voice was hoarse and drawn out.

"For your asshole, of course. Isn't that what you wanted, whore?" the woman laughed. "About twenty people are already waiting in line." she said and disappeared in the darkness.

Gertrude remained alone in the darkness still suspended by her hands. But this lasted only for a couple of minutes.

....

A metal door creaked in the distance. Someone approached her from behind. Two hands grabbed her waist and without any other warning the man shoved in one thrust his stiff and rigid cock up the only remaining hole between Gertrude's legs - her asshole. The fucking was not gentle. The moves were intense and rough. Gertrude knew that feeling. She was there where she wanted - tired, bruised and helpless. She was only a masturbation tool for a stranger. The pain in the shoulders which was killing her moments ago suddenly disappeared, overwhelmed by the force brutalizing her ass. Each thrust pushed her body upwards making her feel weightless. This was not her first time having a cock in her ass, but it was the first time which felt properly - vicious and destructive.

The sperm surged inside her rectum making its way deeper and deeper. The white liquid bathed her insides with tingling pressure, making her shiver with cold sweat. Then suddenly her anus was vacated, left open, cum dripping on the insides of her thighs. She felt empty, as if she had lost the only connection to reality.

Sense of despair overtook her, but luckily for Gertrude it didn't lasted long. She felt another set of hands around her waist and another cock was pushed inside her ass. She cried in pain from the sudden force used on the first thrust, but in the very same moment she felt alive again. This cock was definitely bigger, but it was sliding in and out of her with great ease as her rear entrance was already well greased with sperm.

The third guy fucked her viciously, but it was the fourth one she would always remember. Sharp pain pierced through her body. Gertrude looked own and saw his black hands around her waist. As the initial shock faded she was again able to feel everything. His cock was way bigger then anything she had seen before. He moved slowly, but it still hurt a lot. He was merciful, she was still too tight for him. He made its way carefully until he was fully inside her rectal passage - just over 8 inches of black cock. What was worse it was so thick that her sphincter really struggled to accommodate. The man continued moving slowly in and out working her ass.

Just when Gertrude thought that she starting get used to it, the man flipped. His thrust was so sharp and sudden that it almost split open her anal opening. The next few thrusts were also that vicious if not even more. From that point on this became a battle. The stranger was ramming his meat with the full force he had, lifting her body from the ground for real. Gertrude tried to relax her ass as much as possible, but some damage was inevitable - traces of blood mixed with the semen already lubricating her rear entrance. Although the initial sharp pain had disappeared, the dull senseless feeling in her asshole made her forget for a moment for the whipping and the sewn vagina. Gertude's body bounced with his thrusts and the jar with her amputated clitoris danced with the rhythm.

After a while in this frenzy Gertrude stopped feeling anything. She didn't understand when he started cumming. Endless supply of his genetic material was deposited deeper then ever in her colon. When she regained some of her senses it was because off the strange bruised and hollow feeling starting between her asscheeks and reaching somewhere in her intestines.

Another man took his turn and after him another one. By this point Gertrude was completely numb and lost count. Stranger after stranger took turns emptying their balls inside of her shit pipe. She didn't see even one face. Her only connection with them was the cock in her ass and sometimes a pair of hands.

After a two or three hours of assfucking, Gertrude passed out.

...

Three years later

Gertrude came back from work tired as usual. She undressed and entered in the shower. Most of the scars had disappeared, but a few had remained as a reminder of where the whip had cut deeper.

Back in bed, she felt the usual urge. She needed to cum. Her hand touched the nether region between her legs. Long and wide zigzag scar with a small peehole was the only thing to indicate where the entrance of her vagina once was.

But Gertrude was long used to it. The head of her custom made magic wand passed through her loose sphincter with ease. It has been three years, since this had become her only way to have an orgasm. She pushed the 20 inch toy deeper and deeper, enjoying the buzzing deep in her rectum. She moved the toy slowly in a and out, every time going an inch deeper. Soon she was fucking herself with almost the full length of the toy. Gradually she quickened the pace until her body started cramping and contorting around the vibrating wand. Her mind fell into oblivious bliss as the pleasure waves rocked her body.

Another orgasm later, she was so exhausted that she fell asleep with the magic wand still buzzing and half buried in her rectum.

...

\r\n

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