Ruthless Rosa

[Manbearpig]

Very glad to see this story back. I love it. Thank you!

[Masters_pet]

WOWZA....

i absolutely love it... please continue when you have the time.

[MstDynamic]

Excellent, hope to see continue more to this

[DaniBlonde]

WOW....please keep it coming!

[mandible]

SIX

Chris felt lucky. He snorted at himself as he realised this. How could he feel lucky when he was sitting here so tired - so, so tired - with his face painted black and his hair painted white and only eight hours until he had to be at work?

Well, Rosa still hadn't shown up online and it was 1am, but he had actually just completed his three thousand lines, whereas at midnight when Rosa had said she would be online he had been a couple of hundred short. He had felt a burst of ecstacy and relief when he had written the final word of the final line a couple of minutes ago, but the day had been truly horrific. Rosa had wanted to make his day tedious and awful and she had most certainly succeeded.

After cancelling the planned visit to his mother, Chris had begun the lines. After just a hundred lines he had stared at what he had written, realised that he had to do the same thing thirty more times and felt utterly hopeless. He had actually started to sob, crying real tears. It had taken Rosa only a couple of days to reduce him to this. He felt hopeless, helpless, stupid. How could she do this to him?!

After a few minutes sobbing he had calmed down and been taken over by a grim determination. He would damn well complete these lines and show her! He had put some music on the stereo, set his jaw and begun writing like a robot.

It went well; he powered through another eight hundred lines without even stopping. But then he had a sickening realisation - he did not have enough paper to complete the task! Even with the large filepaper he was using, 900 lines had taken up fifteen complete sheets and he had just a couple left in the pad. Chris had screwed up his eyes in despair. He would have to go out and buy more, with his painted face and hair!

That had been an excruciating trip. He had put a cap on to hide his hair, although it still showed at the back and sides, and after staring at his ridiculous visage in the mirror for a few minutes trying to work up courage he just had to go for it. The middle-aged Indian woman in the nearby store had not said a word as he hurriedly paid for another pad of paper, but there had been a look of puzzled contempt on her face. He had kept his head down on the walk there and back, but had still been able to feel the stares of several passers-by. Chris hated public humiliation.

The feeling of relief when he got home had been huge, and Chris had resumed writing. But by nine in the evening he had realised with a sick sinking feeling in his stomach that he would not make three thousand lines by midnight. His hand was cramping, his entire right arm ached from being in the same position all day, and his pace had naturally slowed. He had also fixed himself a sandwich and a cup of tea at one point when he had still felt confident he could make it, but now he knew that had been time he couldn't afford. All the while, his face felt odd under the black marker ink and his hair was an immovable lump of concrete on his head. At times he had cursed Rosa, feeling what was almost hatred of her for spending an enjoyable day out while making him suffer like this - but those thoughts would always morph into a reluctant arousal at the sheer cruelty she was inflicting on him with such glee.

More than once he had been tempted to simply give up. If he wouldn't finish three thousand, why put himself through the agony of trying to get as close as he could? But he was genuinely terrified of what punishment she might have in store for him and he figured that the closer he got the lighter the punishment might me. And who knew - maybe she wouldn't even really count the lines, just be happy to see page after page and know he had suffered all day. And so he had continued, his hand ever more painful, until he had finally finished just before 1am.

PING!

It was the sound of Rosa signing into the messenger. Chris's heart leapt in a curious mix of excitement, fear, hatred, admiration...

ROSA: Hi there moron!
ROSA: Ahh, still nicely painted I see!
CHRIS: Yes Miss...
ROSA: I'm a little late, but perhaps that gave you time to finish your lines?
CHRIS: They are done Miss ... yes!!
ROSA: Show me.

Chris held up page after page close to the cam.

ROSA: Okay, looks like you did it. You could be a little short, I'm not going to check and I don't really care. HA HA HA!
ROSA: I didn't cae how many you actually did as long as your whole day was ruined by doing them.

Chris's face sank.

ROSA: Awww poor little Chrissy-wissy! You look like you might cry!
ROSA: Okay, I want to go to bed in a minute, I have better things to do than sit here talking to an idiot like you.
CHRIS: Of course....
ROSA: So, get that metal wastepaper bin

Chris fetched it from the corner of his room.

ROSA: Put the lines in. Good. Now burn them.

And so Chris watched the hundred sheets of paper that he had slaved over all day go up in smoke, reduced to ash in under a minute.

ROSA: Now, I am going to bed. You are probably going to want to try cleaning your face and hair, you look RIDICULOUS ha ha!

CHRIS: Yes Miss

ROSA: Work in less than eight hours. Good luck with that cleaning, ha ha haaaa!

ROSA: Oh, and you can expect a surprise at work tomorrow....

And yet again, before Chris could query this latest frightening remark, she had gone.

[mandible]

SEVEN


Chris felt like a zombie when he staggered into the office on Monday morning. He exchanged miserable helloes with a few colleagues on the way to his desk, and could feel himself turning red as he wondered how quickly they would notice his new lack of eyebrows. He also felt as if just by looking at him people could somehow tell what ridiculous, humiliating things he had been doing all weekend.

At least he had managed to remove the marker and whiteout. It had taken the best part of two hours, leaving him just a few hours sleep and hence his zombie-like feeling this morning. Much of the whiteout had come out of his hair with vigorous shampooing, and then he had literally yanked the remaining fragments out with his fingers until careful examination with angled mirrors suggested that he had got it all.

The marker ink had been a struggle. Some came off under the shower and soap, but then he had needed to scrub hard with various rough cloths and sponges. Even then there was still a grey-blackish tinge to some areas of his face, but he had gone to bed anyway, defeated by tiredness. When he had woken there were black marks on his pillow and his face seemed almost completely clean - it seemed that a few hours of sleep with his face rubbing on the pillowcase had achieved what his scrubbing couldn't. Chris felt thankful for small mercies and headed to work determined not to even think about what Rosa had meant when she said he would get a surprise there.

Sinking into his office-chair, Chris looked around at the familiar surroundings of his desk. It was already hard to believe that the last time he had sat here, on Friday afternoon, none of this Rosa business had even been a glint in anyone's eye. His life felt completely changed in the space of little more than 48 hours.

He could feel eyes upon him, and looked up to see Jennifer - who sat directly opposite him - peering closely at his face with an amused and mystified look.

'You've not got any eyebrows !' she blurted out with a little laugh.

'Um.. yeah...' was the best he could manage. He wasn't at his best. Jennifer was a ridiculously attractive girl who every male in the company fancied. Chris was not immune to her charms either, but had long ago decided she was out of his league and not worth the heartache and inevitable disappointment of chasing. Still, the perfectly round breasts bulging under her sweater, the elegantly plucked eyebrows, the high cheekbones, the model-like mouth with its full lips and big white teeth, all that attractiveness made him feel even more ridiculous and humiliated by his stupid browless face than he would in front of a more average person. He also couldn't help reflecting that she had been a good friend of Rosa's when Rosa worked here.

'What the hell happened!?' she asked, still laughing. 'You lose a bet or something ?!'

Chris felt he should stick to one story with everyone. 'No.. it's reeeally stupid, but I got slaughtered on Friday night and for some reason I was in the bathroom and just thought it would be funny to see what I looked like if I shaved them off.....'

His voice trailed off. He felt like a right prune.

'You prune!!' she exclaimed, and then his heart sank as she called out to other girls in the office. In moments Chris was surrounded by amused colleagues and was mumbling his ridiculous eyebrow-shaving story again for their benefit.

---------------------------

A little later, the general amusement at his new look having died down, Chris had his head in his work. He didn't enjoy his job, but it was a relief to concentrate on something and forget about his new circumstances.

A mug of tea appeared out of the corner of his eye. It was being placed on his desk by Jennifer. Her hands were as flawless as everything else about her; smooth skin, long fingers sporting just one elegantly simple ring, and perfect nails with a classy pink-white polish.

'I thought since you don't have eyebrows you should at least have a cup of tea!' she smiled. She was a lovely person, he thought, what factory for perfect girls had she come from?

'Thanks' he said, with a sheepish smile of thanks.

'You know, maybe it could be a new look for you!' she suggested, folding her arms with an amused look on her face. 'We could draw some nice thin eyebrows on for you, add a bit of makeup and you could be one of the girls!'

'Er..... right... um...'

Chris was always thrown when apparently normal girls came out with ideas of humiliation, and there was a slight twitch in his pants.

'Ha ha, don't worry, I'm sure they'll grow back before you know it!' she said and went back to her desk facing him.

'God yeah, I hope so', he said, forcing himself to chuckle.

The two of them worked in silence in their corner of the open-plan office for a while. The tea was good, a touch more sugar than he usually put in but it tasted better for it.

After about half an hour, Jennifer spoke again.

'Hmmm, I just got an email from Rosa, remember her ?'

Chris felt the air rush out of his chest as he looked up. Jennifer's beautiful face was looking right at him and she was grinning.....

[DaniBlonde]

great addition keep it coming

[Manbearpig]

great. i cant wait for the next part.

[mandible]

'Hmmm, I just got an email from Rosa, remember her ?'

Chris felt the air rush out of his chest as he looked up. Jennifer's beautiful face was looking right at him and she was grinning.....

'Um, yeah I remember Rosa. We IM occasionally...'. His voice trailed off, uncertainly.

'Yes, it seems you do!'. There was a light air of hilarity and knowingness in Jennifer's voice. Chris felt his heart sinking. The email icon on his monitor blinked - he had one from Rosa.

'What does Rosa have to say, then?' he asked Jennifer, at the same time as he glanced down and opened the email he had just received. The email was short and not sweet: "I am telling Jennifer a few things. You will do anything she says, Chrissy-girl, or you know the consequences".

Chris looked up, horrified, as Jennifer answered.

'Oh, she just told me about you two having little chats and stuff.'

Jennifer's voice sounded innocent, but there was a grin spreading all over her face which told a different story.

Jennifer glanced round the office, then shuffled her office chair round the side of the desk to be closer to Chris. 'I think I want to see your toenails Chris!' she said, quietly.

His head dropped. He looked at her pleadingly, but she was just grinning. She always seemed so 'normal' - why did so many girls seem to love humiliating men?

He bent down and took off his left shoe and sock, exposing his neon pink toenails. Jennifer giggled quietly.

'Oh they're lovely CHRISSY!' she said. 'Now the other foot!'

He reluctantly shed his remaining footwear, and looked sadly down at the utterly unmasculine, bright shining jewels that were now his toenails.

'Hee hee, I didn't really believe Rosa, but it looks like she was right!'. At least Jennifer was whispering, so as not to draw attention to them in the office. She continued quietly; 'I think I'll hold onto your shoes and socks while I chat some more with Rosa!'

And she swept up his black socks and shoes and scooted back to her desk position. Chris was open-mouthed in shock.

'Jenn?!' he said, in disbelief.

She simply grinned at him. 'I think you better be a good boy.. or girl.. Chrissy!. Just keep your feet under your desk. I'm going to chat with Rosa and then you and me will have a little talk at lunchtime! You can get your shoes back then.'

Chris sat, stunned. Then tried to get on with his work. It was extremely difficult to focus. He kept glancing up at Jennifer, who was typing furiously fast. He knew she must be IMing Rosa now, and he couldn't quite believe this was happening. For what felt like the hundredth time in only two days he felt terrified and completely regretful that he had got into this situation.

After twenty minutes he couldn't take it. He had to contact Rosa. He composed an email:

'Miss Rosa,

hi. Please - this is getting out of hand. It seems like you're exposing me to J even though I have been good so far. Please please be fair....?'

A reply came quckly, inside five minutes:

'Hello Chrissy-girl.

I don't have to be 'fair'. However, I have not exposed you to Jennifer, by which I mean I haven't shown her any of your lovely pictures or IM confessions. I AM however, letting her know that I have complete control of you, and we are discussing the many ways in which she will ensure that you suffer at work as well as out of work. I'm afraid you probably didn't realise that underneath that lovely exterior, Jennifer is just as cruel and evil as me. Oh the chats me and her used to have when I worked there!! You're completely screwed Chrissy. Of course, you can get out of the game if you think I'm being "unfair" - but you know what the consequences would be, don't you?? Now, I suggest you get on with your work - especially since you will be doing some of Jennifer's work too from now on - and don't bother me again. You will go to lunch with Jennifer and do whatever she says. And you will be on cam this evening at 6:30pm, naked and kneeling, with a large bar of soap in your mouth. Bye for now.

Love and contempt,

RUTHLESS Rosa'

Chris felt utterly defeated. He glanced up at Jennifer again, and she caught his eye. All signs of the pleasant, everyday nice girl had gone from her face. She was looking at him with a leering grin of sheer evil. She blew him a sarcastic kiss and let out a low, nasty chuckle.

Chris felt tears welling at the corners of his eyes.

[Manbearpig]

Thank you for bringing this back!!! One of my fav's. Keep it coming

[Bebe_Gurl]

Seeing this just brightened my day! Oh please don't make us wait 4 months for the next installment.

[mandible]

Chris sat oposite Jennifer in the pizza restaurant near their workplace. He was glad to have his shoes and socks on, thankful for small mercies. But Jennifer could not stop smiling that evil-looking smile she had sported ever since Rosa had made contact with her.

A waitress came over. Jennifer immediately ordered and then when the waitress turned to Chris the grinning girl said abruptly; 'Oh, he won't be eating!'. Chris's face went red as the wairess looked at him for confirmation. He shook his head slightly and the young Polish girl shrugged, took the menus and strode away.

'You're paying for mine though, of course Chrissy-girl!'

'Chrissy-girl' made him cringe, and he involuntarily looked around to see if anyone had heard.

'So, Chrissy. Chrissy, Chrissy, Chrissy...'. And she grinned again, broader than ever.

He didn't know what to say, and just shifted uncomfortably in his seat.

Jenn went on. 'Let me tell you a few things. But first, put your hands on your head!'

Chris let out a small groan and looked at Jenn, imploring her for mercy with his expression.

'Hands on your head, Chrissy. I don't think you want me to have to tell Rosa that you disobeyed me, do you?'

In the middle of the busy restaurant, Chris reluctantly put both hands on his head. He sat back in his seat and tried to look more like someone simply relaxing, but it wasn't very convincing. His face was burning with humiliation. Jenn's was burning with pleasure at his suffering.

'Okay, so here's how it is. I'm going to be assisting Rosa in making sure you suffer as much as possible...'

And Jenn went on to calmly explain a few things, pausing only to smile at the waitress when she brought over the food. Jenn explained that Chris would be doing all Jenn's Weekly Collation reports in the office. She explained that he would be coming over to her house at times in order to do various items of housework for her, and that he would be doing so in various 'interesting' outfits. She also explained that this was his last lunch outside the office. From now on, she would be locking him in the stores cupboard (Jennifer was in charge of it and had the only key) each lunchtime with a can of dogfood, which had to be eaten and licked clean by the time she came to release him when the luch hour was over.

'Every day!?' he asked in disbelief.

'Every. Single. Day.' she replied, making a show of taking a delicious mouthful of pizza. 'Rosa was most particular about that.'

Jenn finished eating and rested her chin on her hands. She looked Chris over.

'You have NO idea what terrible things are in store for you, Chrissy!', she giggled.

He swallowed, not daring to speak for he was sure his voice would crack.

Jenn went on, 'You must be regretting getting into this already!'

He nodded, three short nods.

'Oh well!'

Jenn stood up. 'I've got to go to the ladies room. Pay the bill when the waitress comes over. Oh, and - ', she tossed a small item onto the table, '- Put this lipstick on before I get back....'

Chris stared in despair at Jenn's back as her perfect arse wiggled off to the other side of the restaurant to the bathrooms.

--------------------------------------------------


It was almost eight O'clock that evening, and Chris's knees hurt. He was kneeling, staring at his computer and webcam. He had a large white bar of soap clamped between his teeth. The soap kept 'melting' in the warmth and saliva of his mouth, and the taste was disgusting. He didn't dare move, however, because his webcam image showed that he had 1 viewer. It had to be Rosa - she was the only person he had set up to be able to view his cam without him granting permission - yet her icon didn't show her as being online and she had not spoken to him.

And so he knelt, knees aching and mouth filled with the foul soap. Even worse than those physical discomforts was the mental torture. He had been kneeling here since he got hom from work, nearly ninety minutes now. He wanted to have a drink, something to eat, read a book, watch TV, surf the web, ANYthing except kneel here like an idiot. The conflict burned inside him; he knew nothing was physically preventing him from simply standing up, spitting out the soap and doing what he liked. But he also knew, and the knowledge felt like a brick on top of his heart, that if he dared to do that he could face the most terrible consequences.

So he remained in place, kneeling, nude. His feelings went through a cycle of despair, irritation, frustration - but also excitement that he really had found someone so cruel. And then he would inwardly curse himself for feeling that excitement. Being Chris was becoming very confusing and difficult.

Eventually, at about twenty past eight, Rosa's messenger icon blinked into life.

ROSA: Hello idiot! It's been fun watching you kneel there like that while I had dinner, watched a bit of telly etc

CHRIS: Yes Miss.

ROSA: I guess you're starting to realise just how bad this is going to be for you, eh ?

CHRIS: -sobbing- Yes Miss. I don't think I can take it.

ROSA: Ha ha haaaaa!!! Well you always have a choice. Pics to mum, dad, etc. You just let me know when you want me to do that, Chrissy, ok ??

CHRIS: Please.. isn't there some other way... PLEASE?

ROSA: Umm. No.

ROSA: I'm not in the mood to hear your begging right now, Chrissy-girl. Another time maybe, as begging can be fun.

ROSA: But right now, I have other things in mind.

ROSA: I've been checking over that list of items you have. I want you to go and get a tube of superglue.

CHRIS: Gulp. Yes Miss.

ROSA: And your chastity belt. Life is about to get even harder Chrissy-girl........

[striker989]

Great to see that this story is finally being worked on again. Can't wait for the next part!

[Coyote]

Whoooooooooooooooooooooooooooooooooooooooooooooooo ooooooooooooooooooooooooooooo for ruthless rosa awesome story

[mandible]

Chris held up the items to the cam for Rosa's perusal: a tube of superglue, the various parts to the CB3000 chastity device, and the locking plastic tabs for the chastity, each bearing a bold, unique serial number.

ROSA: Aha, the locking tabs, excellent.

CHRIS: Yes....

ROSA: So once one of those is snapped closed, it can only be removed by cutting it, correct?

CHRIS: Yes Miss... they can only be 'opened' by destroying them

ROSA: Right, so there will be no way you can simply change the tab without me knowing from the different number. Excellent.

ROSA: You'll be putting the chastity on shortly, and you will never EVER be removing it without my permission, Chrissy.

CHRIS: Oh... god....

ROSA: Ha haa :-) Yes, perfect. You look so sad and defeated, Chrissy-girl

CHRIS: I am. I really am. I can't believe you are being so cruel to me

ROSA: Ahh, I have barely started. You have no idea!

ROSA: It's fun knowing that I am about to have control of your penis too, for the next... oooh... forty years perhaps!? HA HAA!

CHRIS: Nooooooo

ROSA: Yes. Oh, yes. I'm quite sure you have been 'pleasuring yourself' over the last few days as you think about all this cruelty and humiliation.

ROSA: I'm right, aren't I ?

Chris looked down for a moment, embarrassed. Even now, his penis was at attention.

CHRIS: Yes... I have, I admit it

ROSA: Of course, and I don't blame you... it's about the only pleasure left after all. But I can't allow you that, can I ??

CHRIS: Yes!! You can, please - ! I can have at least that to make up for all that you are doing to me, surely !

ROSA: Nah. Certainly not. I intend to make your life a living nightmare, Chris, so I can't have you jerking off whenever you feel like it.

The matter-of-fact way that Rosa casually discussed her incredibly cruel intentions and plans was hard to believe. Chris was feeling despair again, and his penis was wilting as excitement was replaced by fear and regret once more.

ROSA: Anyway, before we put the chastity on and I explain the rules of that, let's get to work on screwing up your evening.

ROSA: Open the superglue.

Chris sadly took the top off the glue, immediately catching a whiff of its strong fumey scent.

ROSA: NOw... heh heh..... I am so nasty. Start squeezing it all over your hair, until the tube is completely empty.

Chris stared into the cam in disbelief for what felt like the hundredth time since this terrible arrangement had begun.

ROSA: Get on with it. The whole lot Chrissy-girl.

With the slumped shoulders of a condemned man, Chris began squirting the glue all over the top of his head. His friends were all out tonight having a few beers and playing pool, and here he was, naked and putting superglue into his hair.

ROSA: This is so much FUN! I have NO idea how you're going to get that out, or even if you can. You might have to cut it out ha ha !

Chris continued his terrible task until the tube was squeezed flat and empty. His scalp felt odd, full now of little clumps of glued, bonded hair.

CHRIS: Done, Miss. Oh godddddd

ROSA: heh heh, good, enjoy trying to sort that out later. Now.. chastity time...

------------------------------------------

Ten minutes later, the chastity lock was in place around Chris's genitals - a hinged ring clamped tightly in place behind his balls and the clear, hard plastic tube encasing his shaft. Then he showed Rosa the locking tab so that she could note its unique serial number, before clicking it firmly in place.

ROSA: Good boy.

ROSA: Now, let me explain the rules for how you might occasionally be able to masturbate...

CHRIS: yes...?

ROSA: You are allowed to ASK me for permission once each month, on the 28th.

CHRIS: OK

ROSA: In order to ask, you must be on cam and dressed as a nice sissy girl from head to toe. That means: Full makeup, fake nails painted red and at least an inch long, padded bra, a girly top and skirt or a dress, stockings, and high heels.

CHRIS: ohhhh

ROSA: yep, you're never going to masturbate without being dressed that way, EVER! I can't have you feeling like some kind of real man Chrissy-girl! What kind of real man does every single horrible thing that he's told by some girl eh ??

CHRIS: Only a blackmailed idiot

ROSA: COrrect. Now, if you are dressed properly and you ask nicely on the 28th of a month.... I MAY say yes.

ROSA: However, I probably won't, most of the time. If I say NO then you have to pay a penalty, which means you go IMMEDIATELY out and buy that day's newspaper!

CHRIS: Dressed like that ???

ROSA: Durrr - of COURSE dressed like that! It wouldnt be much of a penalty otherwise. You then come back and hold up the newspaper on cam, where I take a picture to add to my files, showing how you dress as a girl quite often. Neat eh ?

Chris was almost sobbing.

ROSA: Now, if I say YES then you will get to take off the chastity device and masturbate to orgasm on cam. Isn't that nice?

CHRIS: Yes Miss... I suppose so

ROSA: Yep, and more pictures for me of course.

ROSA: But there is a catch.

ROSA: If I say YES, then you have sixty minutes to find three people who will message me on IM and also watch you masturbate on cam, at least one of whom must be MALE.

ROSA: If you don't find three people, then you don't get to masturbate and you pay the penalty - but as punishment for not finding viewers, you also cannot ask again for another three months.

CHRIS: Oh.. my... GOD

ROSA: ha ha, neat isn't it? I'm being very kind though - hell, if you do well and are lucky you could get to masturbate as often as six or seven times a year !

CHRIS: Yeah - in full drag and with four people watching me on cam

ROSA: Exactly. No pleasure without humiliation for you, my dear. And other than that, your penis will be in that chastity device every minute of every hour of every day...

ROSA: Understand ?

CHRIS: yes Miss. Oh god, yes Miss

ROSA: well, except when we get it pierced or tattooed that is...........

And once again she signed off without a further word, leaving Chris open-mouthed in disbelief.