Riding Winona Ryder

Riding Winona Ryder. By Maddbean (maddbean@hotmail.com)

NOTE 1: I know very little, in fact actually nothing :), about the California legal system – so anything that happens here is pretty much fiction. I apologize in advance for any mistakes. Three of the characters in this story have appeared (at the time of writing) in one other story (“Fun with Mary-Kate and Ashley”). Clay, the leader of a criminal gang of 3, is tall and muscular and looks out for Clem his 350lb ‘baby brother,’ who is somewhat dim and worships his big brother, and Cletus, their cousin; a short, thin, violent man… all are ex-cons who tend to
find ways to grossly humiliate women and girls involved in their robberies.

NOTE 2: This, or any, of my stories are not intended to promote rape or other nasty things; it’s just fiction. I consider this copyrighted, I hope you respect my copyright


“Prison!? Are you kidding me?!” Winona Ryder was livid, screaming at her lawyer after the afternoon’s amazing events. He had recommended that Winona should plead guilty because “the court will give you an easy sentence at worst, you are a famous actress after all. If you go in front of a jury they probably will not be sympathetic. I think pleading guilty may gain you the judge’s sympathy.” However the judge, trying to show she was hard on crime, sentenced the actress to 15 days, 15 days!! in prison; and not some easy cushy facility but a serious prison where her companions would be hardened criminals. Shit!

After the sentencing Winona was allowed to talk to her lawyer in a private room. “Miss Ryder, Winona, I am shocked… this was not supposed to happen…” the lawyer truly was confused.

“What can we do about it?! I can’t fucking go to prison!! Appeal or something!!”

He put a hand on her shoulder, “please, calm down,” Winona shook his hand off and calmed down a bit, “you would still have to do your prison time waiting for any appeal. Which would take way more than 15 days to happen. In any case, there’s nothing to appeal.”

“Yes, but fuck! I just shoplifted! I can’t be put in prison with criminals! What will happen to me?”

That was a good question, for all the lawyer found Ms Ryder to be an annoying client he did not want to her to be hurt and she would certainly be the target of anyone wanting to make a name for herself in prison, not to mention being made some dyke’s ‘bitch’ for 2 weeks. The lawyer made a small smile, he wished he could see Winona being strip searched at the prison.

“Why are you smiling? There’s nothing to smile about?? What about the press? Can we at least get me transferred to the prison somehow so they don’t film me – pleeease?”

“I’ll see what I can do, wait here.” Not that she had a choice. The lawyer left the room, looking for someone in charge; Ms Ryder was right, the press would have a field day with photos of her being placed on the prison bus and he at least could make THAT part of the ordeal easy.

The lawyer returned fifteen minutes later, carrying some clothes and smiling, “OK, we haven’t got much time… get into these clothes,” Winona looked as if she wanted him to leave the room, but he did not leave so she stripped off her dress and put on the jeans, white t-shirt and hooded jacket he had brought, “here’s the deal. There are two buses leaving the courthouse later this afternoon, one will transfer male prisoners and the other female. The female prisoners will leave later. What you will do is go to the garage with the male prisoners and then get on the women’s bus there. You have to pass right by the photographers to get to the garage and they will be looking for you among the women, particularly looking for this dress, so you can slip onto the women’s bus unnoticed – it’s all arranged. Just keep the hood of your jacket up and everything should be fine. I got these clothes from one of the corrections officers.

Winona looked a little happier, but was on the verge of tears, “I guess that’s something… why would they do that for me?”

“You’re an actress, this is Southern California. Go figure.”

So, sometime later Winona was in a line of a half dozen male prisoners, they were a combination of inmates in prison clothes plus some newly convicted men in street clothes. The men all seemed large and menacing to Winona, so she kept the jacket’s hood firmly up and tried to avoid them as much as possible. One man, a tall muscular man whispered to a very fat man standing to him.

“Those fucking little Olsen whores, I should have killed them when we had the chance, who’d a thunk they’d go to the police. Clem, I am glad you’re such a moron that you taped over the video with a Buffy episode – your lust for Michelle Trachtenberg has been rewarded. It’s a shame you didn’t manage to lose all the crap we stole.”

Clem was not too bright and never knew if Clay was being mean or nice. He broached an important subject, “who will I fuck in prison, If I don’t fuck Clementine evey day I’ll go mad,” Clementine was their sister, and their sex slave.

Cletus spoke, “well, hell, fat-boy I’ll miss Clara as well but you don’t hear me moaning. We’ll find us a bitch in prison.” Clara was Clete’s sister.

Clem looked at Clay and smiled as if he had been promised a free pizza, “can we?”

“Yes, lard-ass, we’ll find some sweet teenaged piece of ass for you to ream every day,” despite his hard words, Clay loved his brother.

“I’d prefer a girl…”

“Well fuckbrain, it’s prison… you don’t get girls there. Although sometimes there’s a nice reporter or lawyer or nurse to mess around with, we try to time our riots around the availability of women. We’ll find us a nice boy with a tight ass, now shut up.”

Winona heard the whole conversation and shuddered, she hoped the women’s prison would be better. Winona and the men passed a checkpoint where their names were compared to a list. Winona was last in line and the corrections officer looked at her and winked, “when you get to the garage just get on the women’s bus.”

“How will I know…”

“There’s two buses, get on the one these boys are NOT getting on. Now keep covered, there’s a million photographers out there.” Winona pulled the hood up again and walked down a short corridor, at the end was another guard and she could hear a lot of voices. She walked out the door and in front of her was a path, at the end of which were a bunch of men in uniform, the other prisoners and a couple of buses – and not in a garage. To the left was a chain link fence, on the other side of which were dozens and dozens and dozens of photographers and reporters, she could hear them jostling for position and arguing with each other, “move out of my way fuck face!” and “touch it again and I’ll shove the lens up your ass” and (what Winona wanted to hear) “even if she covers her head, look for a white dress… remember, white dress; they should be out as soon as the first bus leaves.”

Winona kept walking slowly and approached the guards, “Come on pretty-boy, on the bus.”

“No, I’m supposed to…”


“But…” Winona was worried, if she told the man who she was and he made a fuss she was at the mercy of the photographers, but she had to stay off that bus, “listen, sir… I am not supposed to be here…”

“Well boohoo! You’re soooo innocent…,” he looked her up and down, Winona had pulled the hood down so even her hair was not visible, she looked for all the world like a feminine-looking man. The man looked at Winona with some sorrow, “…listen, pretty-boy, they will eat you up inside – unless you want to be gang-raped the first night, the first thing you should do is go ugly yourself up a bit and find a sugar-daddy to protect you. Be careful on the bus, due to some stupid-ass law we have to keep your restraints off in case we have an accident, so if you get into any trouble just holler and I’ll show those boys what’s what,” he winked at Winona, “and maybe if I keep you safe you can return the favour, now… GET ON THE FUCKEN BUS ALREADY!!!” Winona jumped.

“Listen, but I’m Win…”

The guard almost lifted her as she was pushed on the bus, she staggered a bit as she was shoved up the two stairs and through the door, which was slammed and locked behind her. Winona was about to shout out who she was, but looked around – the men were staring at her, one of them winked. By the time she looked forward the bus was moving, Winona sat in the front row and pulled the hood down a bit – shaking all over.

The bus itself was small, painted gray, with 8 rows of seats and bars on the windows (which were tinted). There was no direct access between the drivers compartment, which contained a driver and a guard, and the passenger compartment. There were six prisoners on the bus; the three she had heard talking, Cletus, Clay and Clem, two black guys (who were in prison clothes and were really big, muscular guys) and a hispanic guy sitting all the way at the back.

The bus drove out and was soon on the freeway. Winona looked forward and listened to the three white men, who talked incessantly. At one point the subject came to who they would make their “bitch” and Clay said loudly, “you see this piece of ass in front of us, he thinks if he covers up he can hide from us,” Clay turned to the black guys, “hey, you guys want his ass?” The black guys did not answer, “OK, then he’s mine.”

Clay leaned forward and whispered to Winona, “what’s your name, hot stuff?”

Winona was silent, she was shaking. She looked forward to the drivers compartment and realised that now she was away from the courthouse she was safe from photographers, but before she had a chance to call the driver Clay spoke again, “fucking answer my question…”

Winona mumbled something, trying to keep her voice low.

“What the fuck did you say?” He pulled at the hood, Winona made an effort to stop him, but it lowered over her shoulder revealing her face and hair. Things happened quickly. Both Clay and Winona looked forward; the driver and guard were talking and not paying attention at all, Winona opened her mouth but Clay was faster he grabbed her and shoved her off the seat, knocking her to the floor. He then dragged her back and put two fingers to her eyelids, pressing them hard. Clay hissed, “now listen, bitch, if you make a sound or call the guard it will take him at least 30 seconds, maybe a minute, to stop the bus get here, in that time I can gouge your eyeballs out of their sockets and shove them down your throat. Understand?”

Winona nodded numbly, she was completely and utterly terrifired.

Cletus spoke, “fuck, man, that’s Winona Ryder! That’s who all the photographers were for.”

“Clete, you’re insane…” Clay looked at her closer, “no, you’re fucking right. Fuck!” He looked at Winona, “I don’t know what the fuck you are doing here, but shut the fuck up and we won’t kill you. OK?” Winona nodded again, “Fuck! Winona Ryder!”

The six prisoners were staring at Winona evilly. The two black guys were silent, but they looked at each other and smiled, the hispanic guy made kissing motions with his lips when Winona looked at him. Clay spoke, “now, boys,” the black guys frowned a bit at this, “there’s more than enough for everyone here in fact,” he motioned out the window to the traffic, “looks like we will be stuck on this freeway for a while.”

One of the black guys spoke, in a deep rumbling voice, “fuck, stop talking, let’s make love to this bitch…”

Clay smiled, “listen, we can make love to Ms Ryder right now, or she can put on a show first,” Clay looked at all the men who all seemed to be happy with the idea.

“Ms Ryder, I don’t give a fuck what happens to you, but if you are a good girl we will let you live. Now strip for us, and stay down so they,” meaning the driver and guard, “cannot see you,” Clay bend down and hissed, “and don’t fucking question me, just do what I say – we can just as easily fuck you if you are blind or not or whether all your fingers are broken.”

Winona looked pleadingly at the men, but stripped anyway, soon she was in her underwear and soon after that naked, sitting on the floor with her arms covering herself.

“Spread your legs, whore, let’s see what you’ve got… wider… wider… spread your lips,” he turned to Clem, “oh how the fuck I wish we had a camera.” He turned back to Winona. Now fuck yourself, I want to see three fingers in there.

Winona wasn’t ready for this, but soon go three fingers in. The men were all looking at her and stroking their penises through their pants. Winona was in tears. “Come on, dear, make it look good – pretend we are your boyfriends. I want it to look real.” Winona was an actress and she put on a good show, all the time in terror of injusry, or worse.

“OK, now get on your hands and knees, show us your ass… spread your legs… that’s right… beautiful!… now take your middle finger from one of your hands… yes, that’s right… and push it all the way up your ass.”

Winona sighed, she had been fucked in the ass before, but not like this. She turned her head to look at Clay then sighed, sucked the finger to lube it a bit, then pushed at her asshole, “come on, bitch, we don’t have all day. Do it now or die.” Winona was panicked and did it, she breathed heavily and shoved the finger all the way in. “Now push another finger in, don’t pull the other one out.” Shit, she didn’t even have a chance to lubricate it. Again she did it, sucking in her breath and shoving a second finger in. “Move it around… now push your thumb in your cunt, fuck yourself. When I tell you to stop your thumb had better be wet.”

Jesus, Winona tried to masturbate herself with her thumb while keeping her fingers up her asshole and forget where she was – it wasn’t easy. She did it for a while until she heard Clay again.She did in fact zone out for a while, “let’s see that thumb,” he bent forward and pulled at her hand, “fuck, yeah! She’s fucking wet, what a whore. Come here, dear.”

Clay explained to the terrified woman that first she would have to give all the men blowjobs. She started in the front, with Clay, Clem and Cletus then moved to the black guys and the hispanic guy. She coughed and spat as much of the cum from her mouth between men. The three white men were more violent than the others and forced her head onto their dicks, while the other guys played with her pussy and ass, they all came in her mouth quickly. Next were the two black men who were really big, they both took their time, working their huge schlongs into her cheeks and back into her throat, when they came they pushed her head tight onto their cocks, forcing her to swallow or be choked. The hispanic guy insisted that she should masturbate him all over her face with her eyes and mouth, which she did – almost blinding herself in the process.

Winona was then dragged to the front of the bus and they started in on her pussy. This time she was forced onto the floor, with her ass in the air, and each man took his turn fucking Winona from behind as her head lay on the floor of the bus. By the end all six of the men had fucked her once, and Clay and a black guy did it twice. Winona was now covered in cum and crying and in pain. She looked to her right and through the glass panel in the bus door, which was not tinted, a car filled with teenage boys was looking at the rape – as she watched one of the boys gave her the thumbs up sign.

By now the bus had completely stopped in freeway traffic and the men stopped for a breather, the only thing left of Winona’s that was not completely abused was her asshole; eventually one of the black guys managed to recover and knelt down and forced his way into Winona’s ass, she screamed and cried at first but was soon caught up in the motion. Once he came Winona had little time to recover before another, then another, then a fourth man fucked her ass. The men sat down again and looked at Winona, dripping cum from every hole with her asshole still opened wide. She could not move and was sobbing.

At some point the bus started moving again. Winona was dragged to the back of the bus and the men, as they recovered, took turns doing whatever they liked – which mainly consisted of masturbating on her, sometimes with help from Winona’s hands. Winona was soon covered in cum and lying on the floor. The worst humiliation, just before they reached the prison, the Hispanic guy put his now almost completely soft dick in her mouth. Winona did not know what to expect but tried to pull away as he grunted and started to pee in her mouth, but he held her and forced her to drink most of it, at the end he pulled out and pissed all over Winona’s face, then dropped her to the floor. She coughed and spluttered then passed out.

After the prisoners left the bus a corrections officer frowned and counted… seven went on but six left, the guard insisted there were seven passengers – his brow furrowed; they were only expecting six in the first place. In a small panic, thinking they had missed an escape attempt, he walked onto the bus and looked around and immediately saw the signs of another rape… clothes scattered about, cum all over the floor, and a smell of piss. He muttered, “Jesus, can’t these animals control themselves for one hour…” and then he saw panties and a bra, he soon found Winona in a fetal position, covered in piss and cum and muttering quietly to herself. “Fuck, it’s a woman…”

Winona was taken off the bus, she showered and generally cleaned herself up, then sat naked in a room for a long time staring into space, barely acknowledging all the guards who passed through to look at her. Finally, Winona was given some clothes and let herself be taken to a van for transfer to the correct prison. She was taken to a room and joined by a rather butch looking female guard who pulled on rubber gloves and brought out a tube of some sort of lubricant; she smiled and said, “Ms Ryder?” Winona nodded, “time for a body cavity search…” Winona groaned, it was still only day one and she was so tired.

The end.

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