Billie Eilish

After a few minutes, the various portable devices gave a subtle ping, and most people pulled it out to see the vote result.

The entirety of the screen was taken up with a window displaying a picture of a young woman, around twenty-one, staring into the camera with a pointedly disinterested look. Underneath it was the woman's name in big bold font.

Billie Eilish.

Now they knew the player, a murmur broke out amongst the guests as they began to speculate on the game. It wasn't uncommon for a single player to be brought on stage, and those challenges were often a bit more intense than the more competition-oriented challenges with two players. The guests immediately began settling bets made during the vote or commenting on the contestant herself.

All the attention directed at one woman was having an intoxicating effect on the guests. Soon though, the excitement of the announcement began to die off, and as the crowd waited for the final preparations to be made behind the closed curtain of the stage, they returned to their previous conversations. After maybe ten or fifteen minutes, the show master ascended the short stairs to the stage and stopped in the middle. One by one, the conversations died down, and a palatable energy of excitement and curiosity began to fill the room. He needed to say nothing to build excitement, the acts themselves would do it. So he milked the silence for as long as he could.

'Thank you all for your patience as we finished preparing the stage for tonight's act. By now everyone knows who the star player will be, I hope you have all had a chance to get any refreshments. So without further delays, let us begin.'

The crowd gave polite applause, as the curtain split down the middle to reveal the majority of the stage. The centrepiece of the scene was a box, carved immaculately from expensive wood on three sides, but the side facing the audience was glass and exposed the lady inside.

Billie was completely nude, with just the steel collar around her neck being the only object she wore. A yellow strap across her stomach secured her to a bench that was currently knee-high but could be raised and lowered as needed. Her arms and legs were below her, resting on and secured to pads touching the floor but secured to the mechanism, putting her in a classic doggy position. She was clearly trying to maintain her disinterested expression, but there was unmistakable fear that she couldn't hide. However, she didn't react to the crowd's appreciative whistles and crude comments. The show master spoke again:

'Billie Eilish, aged 21 from Los Angeles, California. She is here to give her already impressive career a nice boost. That's right honoured guests, this lovely lady, she VOLUNTEERED to be here with us for the coming days. Her box is sound-proofed and the one-way mirror is currently active, so she has no idea she is being watched. Until now, that is.'

He stepped to the side of the stage and pressed a button on his cane. This not only activated the screens on stage and around the theatre but also revealed the audience to her. Billie screamed inside the box, but no sound emerged, and she began thrashing futilely against her restraints.

The Hollywood Director responsible for the camera angles had done his work with great care and love. Every humiliating jiggle from her ample breasts was caught on camera and blown up for all to see. The ass men of the audience enjoyed the camera pointed at her shapely behind, watching her twist and squirm against the leather straps. The main screen, however, was dedicated to a shot of her young pussy, shaved bald for the occasion. Other cameras came online, capturing the scene from more angles. Not an inch was missed. The crowd went almost entirely quiet, as all of them enjoyed this part and none wanted to ruin it by talking over it. As she was silenced by the box, this left the room eerily silent.

After giving the crowd a moment to appreciate the splendour of the chosen player, the show master once more began to speak

'The rules for this game are quite simple. Miss Eilish is going to be shown a series of pictures on the screen in front of her, but they are heavily pixelated. She has to identify what the picture is. She can ask for a hint if she can't make out the picture. But the hint comes at a price. In order to get the hint, she has to make a man cum, using just her mouth. Depending on how good a job she does, the picture becomes a lot clearer, or barely at all. She has one minute to determine whether she wants to make a guess or ask for a hint. If she doesn't choose before the time is up, it is considered an incorrect guess, and we will move on to the next picture. In the end, her score will be revealed, as well as the punishment for any failed guesses.'

As he explained, a box-shaped contraption rose up behind Billie from underneath the stage through a carefully hidden trap door. Once it stopped, it was positioned directly between her legs. and a metallic arm unfolded. On it, was attached a magic wand and whoever controlled the machine adjusted the arm until the toy was pressed firmly against her cunt. The ultra-high res cameras captured every second of it and projected it onto the large screens. When the vibrator was in position, everything remained silent for a few seconds, until a soft hum could be heard from speakers as the powerful microphones picked up even the tiniest of sounds. Billie jerked in place, causing her large breasts to sway violently and a soft moan escaped her lips as pleasure began to flow into her sex.

Billie used what little movement she had to pull away from the buzzing torment. She sighed in relief as the vibrator lost contact with her pussy. That was until the arm moved forward, and the buzzing head was once again pressed firmly against her exposed slit. The operator behind the stage enjoyed playing this delicate game with her - giving her the tiniest relief, only to snatch it away - and so did the crowd. When he felt he'd had enough fun, he pressed a button, and the straps tightened to the point that they dug into Billie's skin and held her completely immobilized while the wand did its work on her.

'Excuse me,' A voice called from the audience. 'There's no countdown.'

'Oh her minute hasn't started, this was all warm-up.' The Show master said. 'What say you, folks? Should we begin? Or give her some more time to think?'

Some of the guests took out their devices to choose from the makeshift vote that had just been brought up, but the majority just sat back and watched as Billie continued to struggle in vain against both the straps holding her in place and the magic wand pulsating against her pussy. The occasional moan or panting echoed through the room as the sex toy was starting to have an effect on the young singer, and it was at this point that the arm holding the wand in place moved back just a little. Before she could stop herself, Billie gave a panicked 'NO' and pushed her hips back to try and follow the wand. The straps allowed no such leeway, and she was helpless as the vibrations reduced, and her growing arousal slowed down. After a second or two, the arm moved forward, until it was mashed firmly against her clit, and Billie let out a piercing wail from the intense pleasure. It lasted only a second before the arm was moved away again, stopping just beyond her reach.

For a full minute, the operator played with Billie. Moving the toy to keep teasing her, always backing off at the last moment, before returning a few seconds later. Billie was growing more and more ****, as she was being kept just short of actually cumming. At last, the show master's voice returned.

'And the results are in. Not many of you made a choice, but that s alright. It seems that you are all quite eager to get started, so let's begin. here is picture number one.'

On a small screen placed in front of Billie, a picture appeared. The same picture was being shown on one of the viewing screens, as well as all of the devices carried by the guests.

'And here is picture number one. If you like, you can use your device to try your own hand at guessing the picture. the sooner you guess right, the more points you get, get it wrong, you will lose points. The guests with the most points can earn some fabulous prizes later on.'

He turned to face Billie, and through the speaker, addressed the flustered and slightly panicking starlet.

'So, now that you have your first picture, what say you? Do you care to hazard a guess? Or do you wish for a hint? your one minute starts now.'

Billie looked at the picture. She had no idea what it was. It was pixilated to such an extent that it was virtually impossible to make a correct guess at this point. She HAD to take at least one hint if she wanted to have even the slightest of chances. As she contemplated her options, the wand was moved forward again, and the buzzing head pushed firmly against her pussy, making her moan in satisfaction and completely derailing her thoughts. A deep and loud moan tore from her mouth as the vibrations almost instantly pushed her right back to the edge, before pulling away. The pleasure, as painful as it was starting to get, served as a cruel reminder of what it was that she had to do. She cleared her throat and spoke up. Her soft voice, amplified to reach even the furthest corners, allowed every single person in the audience to hear her answers.

'I would like a hint please.'

The show master pressed the button on his cane again, and the two-way mirror became a blank piece of glass once more. At the same time, all audio inside the box was cut off, leaving Billie with nothing to hear but her own ragged breath, and the soft pulsing of the vibrating brushing periodically against her pussy.

'It seems Miss Eilish needs a hint before she chances a guess. A smart move if I do say so myself. So let us bring in the person who has also volunteered to help us out tonight. From behind the stage, waiting in a special isolated waiting lounge, walked a man who looked to be in his mid-twenties. he was completely naked, save for an elaborate mask hiding his facial features from any onlookers. The most noteworthy thing that could be said about him, was his cock. It was rock hard, almost impossibly so, and eagerly twitched and swayed with each nervous step he took. On the guest's devices, a message popped up, detailing who the mystery man was.

Finneas O'Connell. 25 years. Singer-songwriter. Most noteworthy detail; older brother of Billie Eilish.

Some murmur began to form among the crowd, and it took the show master a few moments to get their attention back on him.

'Now mister O'Connell, you are here to assist us with tonight's game. For mutual privacy reasons, you have no idea who the player is, and she will have no idea who you are. Your identities shall remain perfectly hidden from each other. For now, at least. I take it you have been instructed on what to do?' Finneas gave a short nod of his head.' Excellent, then I suggest you can start right away, and do enjoy yourself tonight.'

Finneas turned to face the wooden side of the box he was standing next to and quickly found the circular hole at just the right height for his cock to fit through. He took a deep breath to steady himself, and easily slid his cock through the opening. After a few awkward moments, his nerves and anxiety disappeared completely as he felt someone's hot breath against his throbbing member. He groaned softly as what had to be wet lips encircled his cock, and began to slide down his length. Ignoring the growing noise from the crowd, he focused all his attention on the blowjob he was getting. It was sloppy, for sure, but the girl had a good mouth on her and was learning rather quickly in his opinion. It wasn't long until he felt himself nearing his limit. The **** they had given him prior to getting on stage ensure his cock would be hard and ready for the entire night, as well as make it so that he would keep ejaculating no matter how many times he came. They also said that the more pleasurable his orgasm was, the more he would release, and the more intense it would become, for both parties involved. The girl's mouth began to vibrate strongly as he assumed she moaned around his cock. He had no idea what, but it was doing wonders for him.

On the other side of the wall, Billie did her best to quickly suck off the cock that was presented to her. The bench she was strapped to had tilted slightly to allow her better access, and she used that to take that cock as deep as she could. She was by no means an expert, but she had sucked off boyfriends before, so she knew what to do. Halfway through her attempt, the vibrator was pressed squarely against her clit, and she let out a long guttural moan that reverberated around the cock in powerful vibrations. When the vibrator moved away, again at the last possible second, she whined at the loss of contact. But despite the distraction, it wasn't long until he came. She felt his cock swell in size inside her mouth and instinctually tried to pull her head away. The bindings on the bench and the way she was positioned made that impossible though, and she was **** to begin swallowing as her mouth was filled with the bitter taste of his semen.

When he was done, the bench tilted back again, and she was brought face to face with the screen displaying the pixilated picture. The vibrator was pressed hard against her entire pussy, squashing her clit painfully in the process, but it did not activate. In front of her eyes, the picture began to sharpen, not unlike a camera focussing itself. As it did, the vibrator gave a single, short but powerful burst, making her scream in pleasure. Again the picture became clearer, and again the vibrator gave a pulse. Four more times this repeated, and four more times, the vibrator pulsed angrily against her sex, each pulse bringing her dangerously close to orgasm, but never outright there.

Through her sex-fogged mind, she stared at the picture, and even though its shape was still unclear to some extent, she had a good idea of what it was.

'So how was that for a first hint eh folks? I am sure our lovely player enjoyed it greatly, I know this guy over here did. But back to the game.'

He pressed the button again, and the glass became clear again.

'So tell us, do you wish to take a guess, or do you want to go for another hint?'

Billie spoke up almost immediately, though her voice had been modulated through the speakers to hide her identity from her brother.

'I think I know what this is. Is it a bicycle?'

After her answer, the picture in front of her and on the screen around her began to sharpen. After a second, it was perfectly sharp to reveal that it was indeed, a bicycle.

'Oh very well done. That is one point for a correct answer, though, of course, the first picture is always the easiest. But you got it right, so here is your reward.'

The vibrator sprang to life and began to increase in power at a rapid pace. Billie moaned and writhed as the leather straps held her perfectly in place while the vibrator assaulted her defenceless sex. After a scant few seconds, she was using her famous voice to scream and wail like a cheap whore as the vibrator finally pushed her over the edge. Her body thrashed against the straps as the powerful orgasm tore through her. The ultra high-def cameras pointed between her legs captured every second of her pussy convulsing and twitching from the pleasure. After almost a full minute, the vibrator stopped, and Billie finally stopped screaming and trashing as the single most powerful orgasm she had ever had in her young life began to expire. Little did she know that this was only the first. And many more would follow over the course of the night.

She was given little time to recover though, as the small screen in front of her changed to a new picture. As with the first one, it was completely impossible for her to even hazard a guess as to what it was supposed to be, so she did the only thing she could.

'I would like a hint.'

Again, the bench was moved until her face was at the perfect angle to take the thick cock into her mouth. She opened her mouth and was about to begin sucking it when the wand between her legs was switched back on, and her sudden scream of pained pleasure turned into a muffled hum that vibrated along the shaft inside her mouth.

And so she got to work. Dutifully sucking the cock in an attempt to make the picture more recognizable. All the while, the vibrator relentlessly teased her, keeping her as close to cumming as possible. Eventually, she would correctly guess the picture, and her reward was another mind-shattering orgasm that lasted far longer than any she had experienced before. before the whole thing began anew. After the third picture, they told her that they would increase the difficulty since she clearly had no problem identifying the pictures.

Said difficulty came in the form of a stagehand entering the box and attaching a steel rod to the machine. Her wonders of what it was going to do quickly disappeared when she felt something begin to push against her pussy. With a high yelp, a thick, long, artificial cock slid easily into her cunt, and began to fuck her at a steady pace. It, along with the insistent vibrator against her clit, had her moaning and panting in seconds. It wasn't until she was close to cumming that the operator pulled back on the intensity, and the next image appeared in front of her. Little did she know, but the cock fucking her was a perfect replica of the cock she was **** to suck off. Not only was she unknowingly sucking her own brother, but in a way, her pussy was receiving pleasure from his cock as well.

It wasn't until the thirteenth image that she slipped. The continuous teasing of her sex, paired with the frequent sucking she had to do, and the overwhelmingly strong orgasms were starting to wear her down. Her current picture had been especially difficult for her to nail down, and even after several hints, she failed to identify it. The persistent fucking and vibrating of her pussy and clit had worked her into a frenzy of **** sexual frustration as her orgasm kept on building to ever higher intensity, only to be denied at the last moment. As a result, her skill of sucking that cock, which had been steadily improving as she grew accustomed to what the mystery man liked, began to suffer. That in turn gave her smaller and smaller hints, and it was only a matter of time before she guessed incorrectly.

'Oh, I am sorry for you player, but that answer is not correct.'

In front of her, the pixels cleared away, and the true shape of the picture revealed itself to her.

'Now, just as you get rewarded for guessing right, you should obviously be punished for guessing wrong.'

Billie feared what that could possibly mean, but she had no time to dwell on those fears, as the cock sped up faster than it had been for the past minutes. The vibrator increased in strength as well, and Billie let out a deep moan of pure need as the pleasure surged to previously unreached heights. She strained against the straps holding her in place, body shaking, her big juicy tits swaying wildly as she was finally allowed to crest that elusive peak into orgasm. For a split second, pleasure and euphoria flooded her entire being as the first waves of her climax rippled out from her pussy.

And everything stopped.

In one swift motion, the cock pulled entirely out of her quivering cunt, and the vibrator pulled away well beyond her limited reach. Billie's cries of pleasure turned into a strangled wail of disbelief as the orgasm was mercilessly cut off just as it had started. Her pussy convulsed around nothing, each contraction a painful unsatisfying sensation. She trashed futilely in place as tears began to form in her eyes. The sensation was intense, the experience new to her, and she was completely powerless to do anything about it. Vaguely, as her mind tried to keep up with the waves of unsatisfying fake pleasure, she heard the laughs, jeers, and applause through the speakers of the box, and her shame rose tenfold. It took a full minute, maybe longer, but eventually, the mockery of orgasm had ended, and she lay panting heavy on the bench.

The cock was promptly reinserted, and her pussy eagerly convulsed around it. The vibrator resumed its by-now-familiar place against her clit. But it wasn't until she felt something similar press against her anus that she realised she was not alone in the box. The stagehand had attached a second rod, and a heavily lubed rubber cock was steadily pushing against her thus far unused asshole. She shook her head in denial and began to plead for them to not go that far, but the only thing her pleas gave her, was more jeering and laughter, and yet another picture that she had to guess. To her shame though, the ruined orgasm had her entire body **** for some real relief, so when the cocks began to pump in a steady off-beat rhythm, and the vibrations ramped back up, she moaned wantonly and completely forgot about the picture.

'Only a few seconds left before we have to call the next picture a failure as well. Can it be that our player is overwhelmed by this latest development? Perhaps she has never had something inside her anus before, and the sensation is simply too much. Regardless, she had better make a choice now, before we have to punish her again.'

That pulled Billie out of her sexual frenzy, and it was with great effort that she could manage to as for another hint. Not wanting to feel that ruined orgasm ever again, she set about to please the cock with renewed vigour. She was going to give him the best blowjob of his life, and she was going to make it through this.

Finneas meanwhile was having the time of his life. He was told that all he had to do was just stand there and follow the instructions, and have a hot young twenty-something suck his balls dry. But he never in his wildest dreams imagined that that was exactly what was happening right now. She had already adapted to him in a way that each next blowjob was better than the previous one, she learned just that quickly. But whatever it was that had the woman wail in such despair had lit a fire in her. When next he felt her mouth on his cock, there was a noticeable difference. She ran her tongue all along his length, making it swirl just underneath his head as he liked it so much. Then down again, before taking his balls in her mouth, one after the other, and servicing them as well. The near-constant moans coming from her had her mouth vibrate all along his shaft when she began to deep-throat him. At first, she was clumsy, and could barely take half his length, but now, she easily went all the way until her nose touched his pelvis. She had truly become a pro at sucking his cock, and he savoured every second of the experience.

And like that, the night continued. For Finneas, it was one heavenly blowjob after another, each better than the previous. For Billie, it was a taxing and exhausting ordeal as the three toys teased and fucked her to her absolute limit, to the point where she became delirious with need, and only relented when she made a guess. Then, it would result in either an orgasm so strong that it literally wiped her mind clean of any thought save the intense, body-rocking pleasure. Or it would result in another ruined orgasm that was equally painful and utterly unsatisfying but always left her wanting more.

Picture after picture this repeated itself. Until the point where Billie thought she couldn't cum anymore, then still they continued. Her face was a mess of tears and thick streaks of dried semen from where it spilt past her lips. She was actually starting to feel sick from the amount of his stuff she had swallowed, and she was partially amazed by the fact that the guy she was sucking off repeatedly could last so long as well. But finally, things started to slow down. After her last picture was done with, the sex toys slowed down until it was nothing more than a steady, slow presence keeping her aroused and her desires simmering in anticipation for the next orgasm. She had long since forgotten about the audience but was promptly reminded of their presence when they started to clap and cheer loudly, while the show master spoke up once again.

'And that is it for tonight's challenge, honoured guests. Please give our player a well-deserved applause, for she has done extremely well. But now, let's see how she did score-wise, so we can determine her final, grand prize.'

On the main screen directly above the stage, unseen by both Billie and Finneas, two numbers began to count upwards. One in green, counting every picture she had guessed correctly. And one in red, counting the incorrect pictures. The entire theatre became silent and tension filled the room that all present felt. Well, all, except Billie, who was absently writhing her hips against the toys, chasing her latest orgasm that had been steadily building the whole time the show master had been talking. When that proved futile, she opened her mouth and tried to reach the still-hard cock in front of her, as that usually resulted in more pleasure. But the bench was in such a position that it remained just barely out of her reach, and she wined pitifully as the futility of her situation sank in.

'And it looks like the result is in. Well, would you look at that? Far more correct answers than incorrect ones. Though those incorrect ones need to be dealt with. But how to do it.'

The show master walked back and forth on stage, as if deep in thought before he stopped next to Finneas.

'You there, good sir. You have held yourself admirably throughout the night, and more than earned a special reward. How would you feel about getting some one on one time with our lovely player, right here, right now? Just you and her. Free to do whatever you want? You are already more than familiar with what her mouth is like, but wouldn't you like to feel her other holes as well?'

He pressed a button on his cane, and the theatre was filled with the moans and **** pleas of Billie as she writhed helplessly against the toys.

'Just listen to that. She's all but ready to cum, even though she has already cummed so much tonight, she is such a slut that she can easily go for more. And you can be the one to give her what she wants. Don't worry about revealing yourself. We will take ample measures to ensure both your and the player's identities remain hidden from each other. So what say you?'

Finneas was silent for a moment, but the constant sound of Billie's increasingly **** moans quickly won him over. He nodded his content, and the Show master gave a wide smile as if there ever was any doubt.

'And there we have it honoured guests. Our volunteer has agreed to help punish our player for her failures. So let us say that he has fifteen minutes to do as he pleases with the player for each incorrect answer. Now it looks like our lovely player has failed to correctly guess a picture seven times, so that makes one hour and forty-five minutes in which she is all yours.'

Across the theatre, the guest's devices all lid up as a new vote suddenly activated. There were only two options this time.

Allow Finneas O'Connell to freely use Billie Eilish for one hour and forty-five minutes. (1:45)

Do not let Finneas O'Connell freely use Billie Eilish and instead keep her punishment open to be added to a later challenge.

One by one, the guests began to vote.

And that is another challenge. Special thanks to Dissonant Soundtrack for providing the idea, and I hope you all enjoyed it.

The result of the vote is;

in favour of letting Finneas fuck Billie; 3BlackSheep3

In favour of postponing it till later; Pleki

So with a tie, I'll act as a tiebreaker and go with the postponement as well.