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The Cleaner (Grumpy Koala x scarlet_rose)

Grumpy Koala

Grumpy Koala

Super-Earth
Joined
Apr 27, 2015
Location
United States
Riley was uncomfortable. He could feel the vile aura in the air. He knew something bad was going to happen. It was that nip in the air. Of course it didn't help that he looked so girly. Too girly, really. Gussied up in cute makeup and wearing the clothing he was. 4" black platform heels, a white cocktail dress with a low neckline, a set of lacy pink panties and a bra, a black garter belt with matching stockings... And his long, silky brown hair was just the icing on the cake. Clipped in his hair was a fake daisy that kept an obnoxious bang out of his face. His green eyes fluttered, long lashes batting as he did so.

To say the least, he made a very convincing girl.

It was a dark night. Too dark. And the path he chose wasn't the wisest, especially with his attire. He picked up the pace, passing a number of dark alleyways. And he felt like he was being watched.
 
Stella had been at a board meeting in her company and was pissed off. The deficit was just too great for her to ignore and she had to let one of the directors go. She was really angry that the man had let things get out of hand like that. It would cost her several millions to correct the mistakes of one simple fool. She would have loved to make an example of him and had thought of Robert De Niro in The Untouchables chanting 'Team play' as she imagined caving in the man's skull. But sadly doing so would have left her with too many ends to tighten.

Instead Stella had convinced herself that she simply needed to fuck the shit out of someone. She made her driver make a round trip through the strip where the prostitutes usually were hanging out. But the shemale didn't see anything she liked. She was getting more and more desperate. She almost overlooked a cheap looking girl walking past an alley as she wasn't in the mood for girly pussy. But at the last moment she realized that the figure was actually a boy. Even if he was very convincing she could always spot sissies even from a great distance. There was just something about them that got her even more turned on. She told her driver to stop and the limo came to a halt. Stella stepped out and looked at the girl. "You need a ride!" she said, making it sound more like a command than a question.
 
Riley looked over at where the shout came from. "Wha~" he stammered quietly, seeing the woman. Fear flooded his mind. His cheeks turned red. Not because of his attire, but because of how he must have appeared. Like a cheap hooker. He just wanted to get home to his studio apartment and lay on his bed. "I... I don't... really," He responded, not wanting to imply that she thought he was a prostitute. Riley, however, was not aiding how helpless he looked by being such a stammering fool. He was tiny, 5'3" to be exact, and had a subtle curve to him. Hips wider than that of a normal male. His face was certainly not that of a male either. Even without the makeup, his features were heavily feminine. Sure, Riley loved dressing like a girl, but sometimes the catcalls and slaps on the ass made him empathize with the women who complain about those things. And his ass certainly was a perfect pair of bubbles, stuffed into the form-fitting party dress. An ass that faced the narrow alley he foolishly stopped in front of.
 
Stella moved closer to the young trap. With her 4 inch heels adding to her natural 5'10" she was almost a foot taller than the small girlie boy. As she moved her hips swayed and her large breasts heaved as she took air into her lungs. She smiled at Riley. The hot trap was just looking so delicious, "So you are playing hard to get? Such a fucking whore. Just makes me more horny." She said as she could feel her panties strain against the growing hardness.

Stella didn't stop until she was under a foot away from Riley. "Get down and suck my cock whore!" she demanded with a voice that was used to getting what it wanted.
 
"What?" Riley whimpered, "N-no! Leave me alone!" This wasn't happening. It couldn't be. He backed away slowly, into the alley way. "I won't do it! You can't make me!" He turned around and ran as fast as he could in heels. But he didn't get very far. The alleyway ended very quickly in a dead end. Trapped. "H-help!" He cried, "Help me! Help me please! I don't want to be raped!"
 
Stella continued to walk towards the trap. She did't care what the whore wanted. What mattered for Stella was what she NEEDED. And she needed to fuck some tight girl-boi asshole. Her long strides soon brought her up to Riley who had the back against a wall now. "You play the role good bitch." She said as she grabbed one of Riley's hands and spun the boi around. "But if you don't want to suck it I'll just fuck you raw." She said as she grabbed Riley's ass under the skirt. It felt so nice and soft, so fuckable.
 
Riley screamed as loud as he could when he was turned around and groped. Molested. Felt up like a piece of meat. "Stop it!" He screamed, "Don't! Please!" He squirmed but couldn't break free. "Y-you don't want me! I've got a penis! You hear that? I have a dick! I'm a boy! No pussy to... to rape. You... you... you rapist!"
 
Riley's screaming only spurred Stella on. She pushed him to the ground and got down on her knees behind him. "Yesss. That's what I need. A good girly ass to fuck." She said as she grabbed the sissy's hair and pulled his head back. She licked his cheek and said, "I LOVE fucking sissies like you." Her hard cock had escaped her panties and was tenting her skirt and rubbing against Riley's ass. "If you spread your ass now I'll go easy on you bitch." She commanded, not that her monster erection would ever be able to do anything easy on Riley's asshole.
 
"What...? No!" He cried as he was pushed to the ground, "Please... stop ..." Tears gently streamed down his cheeks as he yelped in pain as his long hair was pulled back. He could feel the massive dong against his ass, threatening to rip him apart. "No!" Riley yelled, regaining a little composure, "I won't help you rape me, you monster. I... I saw your face! I'll report you to the cops! You should know they don't take kindly to rapists in this town!"
 
The cops were the least of Stella's worries. She had gotten away from far worse than rape before. While still holding on to Riley's hair she used the other hand to rip away the sissy's panties. "Such a lovely ass." and then she spat on it, letting the spit run down the crack.

That was however all the lubrication Riley would get apart from Stella's precum. She positioned the cock head at Riley's entrance. "Come on bitch scream." And then she pushed her massive cock head into the tight and welcoming ass.
 
Riley whimpered as it seemed his rapist didn't care in the slightest that he could turn her in. A yelp escaped his lips as his panties were ripped away and his virgin butt and moderately sized cock were exposed. "N-no..." He begged weakly, cringing at the way she spat on his asshole, "Gross..." His eyes almost flew out of his skull when she started to enter him. He let out a girly, bloodcurdling scream of pain as he was forced open much wider than he had ever been before. "It hurts! Please... stop! It hurts so bad..." The cock inside him burned the sensitive walls of his ass, bringing forth new pains unimaginable. "S-stop..."
 
With a soft and almost caring voice Stella whispered, "Relax your ass and accept it. You are not getting away from it so try to enjoy it." She let her cock head stay in Riley's asshole for a while to allow the trap to realize that there was no getting away and to give him time to get accustomed to the thick invading member. As she stayed there she whispered to him, "you are such a beautiful little girl." As she gently caressed his exposed balls and cock.
 
He sniffled and nodded slowly. This was going to happen whether he liked it or not. As wrong as it felt to sit there and take it, he had to. It was the only way to possibly escape without not being able to stand. Besides... who would know he submitted?

With a light exhale, he relaxed his muscles as much as he could in a situation like this. Of course, his ass was still very tight, and still burned with pain... but the pain was less significant. And he felt his cock harden just a little bit as his rapist's fingers ran along its length.

Wait what??? He thought, Am I... actually enjoying this? It can't be! I'm being raped like a helpless little girl! How could I evert feel pleasure out of this?! But... her fingers feel so nice on my dick...
 
The fact that the sissy's cock were hardening weren't lost on Stella. She took hold of Riley's cock and began to stroke it. And then she began to move in the trap's ass. Slowly she pushed her cock in a little with enough care not to damage the girly boy. She stopped once a few inches of her cock was inside the hot ass. Then she pulled back a little and pushed even further in. She kept this up until she had more than half her cock inside the sissy's hot and welcoming ass. "You like it whore? All whores love my cock." She said, "I'm almost half way into you. Get ready for the best part."
 
Riley grunted, wincing in pain as he was spread apart even more, the huge dick sinking halfway into his ass. His cock hardened to full mast as she stroked him. He felt her massive cock pressed against his prostate. Unintentionally, he let out the slightest moan, and had the tiniest hope that the rapist would go deeper. "P-please be gentle..."
 
Stella was so turned on and horny that she almost didn't notice Riley's weak request. But instead of ramming the rest of the cock into the sissy's ass all at once she just began fucking him. Nothing about having a foot long cock shoved into an ass could be gentle but there was no doubt that Stella held back. She fucked the tight ass and still more and more of her cock entered Riley. At the same time she kept stroking the sissy's cock. She did notice the moans from Riley and smiled to herself. The bitch really liked getting fucked like this. That was better than good.
 
His ass was on fire. The pain was almost unbearable. Riley felt tears well up around his eyes and drop to the pavement. His cock was painfully hard and he couldn't believe that he was so turned on by the violent abuse. By the way he was getting brutally pounded, anally raped without concern for his own safety.

The pain started to fade. The burning started to stop, and he started to feel the pressure of the massive girth splitting him with every thrust. And his prostate was on fire, sending wave after wave of pleasure to his brain. He could barely handle it. His moans started to get louder and louder as his orgasm started to approach. "M-more..." He moaned quietly, "It... feels... ugn..." Drops of precum started to leak out into the rapist's hands. So ashamed, Riley couldn't hold back anymore. The little virgin trap moaned loudly as a few spurts of jizzom squirted out of his cock.

Things started to blur and numb. The only thing he could feel was the violation of his anus. His eyes fluttered as he fought the urge to pass out. He was unsuccessful, and he went limp.
 
Stella could feel she was approaching her orgasm. Her hard cock throbbed with pleasure deep in the sissy's ass. She could feel her entire cock burring deep into Riley as she heard the sissy moan and beg for more. And as she felt the sissy cum into her hand she could hold back no longer herself and moaned as she began to fill the sweet ass with her thick and hot shemale cum. "Fucking yes. You are one hot bitch." She moaned.

Stella pulled out and realized that her whore had passed out. She shrugged and considered leaving the sissy in the alley. But she had really liked the ass and she had liked how the slut had taken to her cock. So she picked up Riley and brought her to her car. She signaled to her driver to open the door for her and she put Riley into the back seat and sat next to her. In the light of the car she could see how pretty the boy actually was. She'd be a nice little toy to have at home. And at that moment Stella decided that Riley was hers.
 
Riley slept dreamlessly for about thirteen minutes before he stirred awake and found himself riding in the back of a car. "W-where am I?" He asked softly, "Agn... my ass is sore... and... why am I leaking?" He reached down and wiped up a bit of the fluid, bringing it up to his face. "Is that... jizz...?" His memories quickly rushed back to him, and he remembered how he was raped brutally and... disgustingly, he enjoyed it a little. At least his body enjoyed it. His mind still felt violated and helpless.

But then it begged the question... where was he? Who's car was that? He turned his head to see the woman who raped him and he jumped, backing against the door of the car. "What the? Why... where am I? Are you... kidnapping me? Oh my god, you are! Please! Let me go! I don't have any skills, I'm useless! I... I... I don't even have a job! And my family doesn't care about me I'm so useless! And now I'm realizing... I'm not making a very good case for myself... please, just let me go..."
 
In the light of the passenger seats of the limo it was easier for Riley to see Stella. His assailant looked at him with a smile and caressed his cheek. "Oh my little sweetie. Don't you worry about a thing any more. I'll take good care of you my sweet little flower."

She moved over and gently stroked his back, "You are mine now and there's no way you are getting away from me. I'll make your life so much better than it ever were before." She said with a sweet voice. "And.." she added, "you seemed to like taking my cock in your tight ass. I'll promise you that you'll be doing that a whole lot more from now on."
 
Riley whimpered softly as he shrunk into his shoulders. He felt like trash. Like a toy. For all he knew, he was a toy now. Doomed to be someone's cock sleeve whenever she needed release. Maybe it wouldn't be all bad. If she was telling the truth, and was actually going to take care of him... a little anal violation now and again wouldn't be so bad...

He perked up just a tiny bit. "T-that's it? J-just a little bit of... butt stuff and you'll... take care of me?"
 
Stella chuckled. "Butt stuff. You are so sweet." She put an arm around his waist and pulled him towards her, "Of cause I'll take care of you sweetie. As long as you are good to me I'll be good to you." Stella realized that her hand was getting soaked with her own cum running from his asshole. She took the hand to her mouth and licked some of her cum from it. "Hmmmm. I love the taste of my cum - here." she put the cum covered hand right under Riley's nose, "Taste your mistress' cum."
 
At first, Riley resisted. But the must if the thick, warm, white cum flowing into his nose td him otherwise. He hesitantly stuck his tongue out and licked the salty morsel off. He tried to hate it... but if was so delicious. He had to have more. But how?

"M-mistress?" Riley spoke up, "Are there other things you want me to do besides... let you... um... do nasty things to my butt?"
 
Stella noticed how much Riley liked her cum. He really was a cum slut, even if he didn't know it yet. But more importantly she noticed how submissively he asked his question and how he called her mistress. "Of cause there are other things sweetie. I want you to look pretty all day long and be my girly sissy boy at my home. I want you to welcome me home with a smile every day and I want you to be happy. And of cause you do have one other hole than your ass sweetie." She realized she didn't know what her new toy's name were. She felt generous and would allow the sissy to either give her his real name or make one up he wanted her to use, "So tell me sweetie. What would you like me to call you?"
 
"By my name, preferably..." Riley said, almost smiling, "My name is Riley. It's... gender-neutral so... I use my name when I'm... well you know." Riley felt a little tumble in his gut when she mentioned another hole. His mouth. That have him an idea. A nasty idea.

"Mistress..." Riley spoke softly, "My... butt was probably really dirty... so... maybe... your... your wee needs cleaning?"
 
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