DeaDia 15: The Wager

“Hey, I thought you might like this. Or maybe you need if for proof or something.” The message had an attached picture. Ember in her workout clothes. Her sweaty hair plastered to her face, her eyes covered by a black mask, headphones over her ears. Her mouth was opened in a small slit. A sheen of sweat glistened on her exposed neck and abs. The cleavage of her bra was a little darker where she had spilled some water on it, and she could faintly see her hard nipples poke through the fabric. Her legs were spread in the machine. If she looked very closely, she could see a small dark spot in her crotch. She had been so very fucking horny. No, not had been, still was.

She fell down on the couch and ripped her pants off. The yoga pants pooled around her ankles. No time to take off her shoes. At least her panties couldn’t get in the way. That was one advantage of Synth’s task. Her fingers found her wet lips. She wanted to cum. She needed to cum. The first finger entered inside her easily. Two strokes before she added another. Her other hand pinched her hard nipples through her sports bra, before she traced down her tummy.

Her phone chimed. The DeaDia chime. She could just ignore it. Orgasm first, app later. But what if there was an error in her previous challenge. She had seen the challenge completed message, right? The computer voice had told her she had been successful. Another finger entered her aching pussy. Normally, she wouldn’t use this many fingers, one, maybe two was enough, but now she couldn’t get filled up enough. Maybe she should buy a dildo to fill her all the way up? Her other hand traced further down. Another DeaDia chime. Fuck. She really should look. But she also really wanted to cum. Her excitement had been building for too long. The last time she came had been this morning. A part of her was surprised at the thought. She had already orgasmed this morning, normally, she would maybe yearn for another release in three or four days. Not this time. Three fingers in her pussy. The whole day had been filled with activities that either built her embarrassment or her excitement, and most of them at the same time. On the one hand, it was weird. The horniness she felt whenever she thought of people watching her. On the other hand, she didn’t really care. Her finger touched her clit and she let out a sigh. The long awaited orgasm wasn’t far off.

Another DeaDia chime lit up her screen. Even though she didn’t mean to, she caught the notification. “Five minutes left until offer expires.” Good thing she wasn’t interested in any offers. The screen turned black again and Ember saw the reflection of her face in the black screen. Lips parted, hair plastered to her sweaty face. The face of someone who was enjoying herself. A face she had seen before in porn. A face she had seen before in her own clips. She worked her way up to her orgasm. Her pussy making wet sounds around the three fingers that were pistoning inside her. What would the offer be about? Probably some kind of sex toy or something. No, back to her pleasure. In her mind, the fingers in her pussy weren’t hers. They were Luna’s. The blonde gym bunny had pushed her back on the couch before roughly stripping her down and furiously finger fucking her pussy. She’d never had these thoughts about other girls before. Why now? Was it to do with DeaDia? She had completed more than ten challenges so far, maybe her level had increased and the offer had something to do with that? Maybe another gift, like the one Vermillion had sent her. Maybe she should look. Check it out quickly and then get back to her orgasm. Reluctantly, she removed her hands from her pussy, but not before stroking one more finger up and down her slit, a promise for pleasure to come.

*Synth proposes a wager

“Hi Silvia, you must be quite horny after the day you’ve had. If I was you, I would have been masturbating as soon as I came home. But I believe you are better than I am. I believe you are able to control yourself. So I propose a wager. If you can edge five times for me tonight, and don’t cum before midnight, I will make sure that for the next three days you will receive no challenges. If you do cum before midnight, you will be following my instructions tomorrow. The day after tomorrow, DeaDia will continue as normally.

Refusing the wager holds no penalty other than my disappointment.”*

Below the text, there were two buttons. “Accept” and “Refuse”. Ember’s fingers hovered over the refuse-button. That’s what she should do, right? Just refuse this wager, finger herself to completion, and see what tomorrow would hold. But what about the reward, though? DeaDia had already taken a too big role in her life. It would be nice to be able to concentrate on her own life and her own tasks without any distractions. And the pause in DeaDia would include Friday, the day of her first television appearance. On the other hand, Synth wouldn’t offer this challenge without a way for Ember to fail. She’d be able to get to the edge easily, hell, she almost was there before she opened the app. A countdown flashed, counting down from 10. She should refuse, refusing was the smart option.

Her thumb pressed the green accept button.

Three days without DeaDia would be very welcome. No more constant checking of her phone, no more strange rules, no more humiliating tasks. No more random perverts masturbating to her content. She just had to postpone her orgasm until after midnight. She could do that easily. She had enough self-control to keep from cumming for a few more hours. And after midnight, she still could cum. Not because she was ordered to, but because she wanted to.

“I knew you wouldn’t refuse. You couldn’t resist the challenge, could you? Now let’s see if you are as strong as you think you are. The rules of the game are simple; You will try to keep from cumming, and I will do my best to make you lose control. Now, you owe me five edges, so let’s start.

For this first one, let’s keep it simple. Use your hands and your imagination and get to the edge.”

Synth sounded quite confident. They must have a plan to make her fail, but Ember vowed to keep strong. With all the torturous pleasure she had undergone in this week, she was fairly certain that she knew where her limits lay. Her hand moved down to her pussy once again. Even though Synth’s wager had distracted her, Ember was still very wet. If only she had orgasmed before this wager, she knew she would have had a big advantage. Right now, part of her was still looking for release from a very frustrating day. Still, she was in control of her own body. She had to be. Two fingers entered her pussy, Luna’s long digits. Ember put the index finger and middle finger of her other hand in her mouth, imagining it was Luna forcing her mouth open and making Ember suck on her fingers. Then Luna’s fingers caressed down Ember’s body. Trailing a trail of saliva until they found the little nub of her clit. Luna started to put some effort into finger fucking her. Trying to bring her to an orgasm as soon as possible. Ember felt the orgasm build. She opened her legs as far as the panties around her ankles allowed her. Giving the ghost of Luna even better access to her sensitive spots. Her hips pushed against her fingers. Pressure built inside her, yearning for release. A dam ready to overflow, cracks already forming. Luna didn’t stop, Ember was powerless under her ministrations. Almost, the dam started to give way, her orgasm was inevitable. Her Erastos band buzzed. Ember opened her eyes. Luna was gone. She removed her fingers from her pussy.

“That was one. I hope you enjoyed yourself, because that is the goal of this whole exercise. Now, for the next edges, I will need you to collect some items from around your house. Please get the following items for me:

Clothes pegs

A hairbrush

A ruler

Your Niobe device

Oh, and something that can serve as lube could also be useful.”

Fuck, what was Synth planning? It couldn’t be good. But giving up would mean that she lost the wager. Best to just get on with it. She finally got rid of her shoes and her yoga pants. She had a feeling that she wouldn’t be needing those any time soon. For the sake of it, she also removed her sports bra to be fully naked. A few days ago, being this unclothed would have bothered her. She would have looked for a robe or at least a towel to wear. She would have got undressed in her bathroom, only coming out when she was fully covered. Now, she couldn’t give a damn. Who was there to look at her? Her blinds were closed, her door was locked. A few minutes later, she had nearly everything lying ready on her coffee table. A container of clothes pegs, her black hairbrush, the Niobe and a nearly full bottle of lube.

“Sorry, I don’t have a ruler.”

“Do you have any wooden spoons?”

“Yes.”

“Go get one and report back for your next edge.”

Quickly, Ember walked into the kitchen and grabbed a long handled wooden spoon.

“Okay, I’ve got everything.”

“Good. Let’s see if we can get you over the edge.”

“Now, before you get to the next edge, I want you to do something for me. First off, wear your Niobe. Don’t worry, I won’t make it make you cum, that would take the fun out of this game.”

Ember looked at the black device, she had woken up wearing the fake dick this morning. This would be the third time in just as many days that she would part her lips with the dildo. She couldn’t deny that it was expert at making her feel good, though. Her pussy was still plenty wet from her previous denied orgasm, but she still lubed up the fake cock. Easily, it slid into her welcoming pussy. Her walls pressing against the plastic, the front part covering her clit, promising maddening vibrations.

“When you’ve done that, take your hairbrush and slap your ass with the flat of the brush.”

Ember took the brush, this didn’t sound too hard. She bent over from the couch and took a swat at her behind.

“Did that hurt?”

“Not really.”

“Do it harder.”

Once again, Ember hit her ass with the brush. This time, a resounding slap of plastic on flesh ringed around the room. She felt the sting of the brush on her sensitive buttock.

“Did it hurt this time?”

“A little.”

“Then you get a little reward.”

The Niobe sprang to live, the vibrations less than a tenth of the maximum Ember had experienced, but still Ember welcomed the sensation. After a few very short seconds, it died down again. Enough to get her warmed up, not nearly enough to get her close to the edge.

“I’m sure I don’t have to explain this to you, but with the Niobe in your pussy, you have no way to manually stimulate yourself. You still owe me four more edges. If I don’t get them before midnight, the wager will also count as failed. So, with that in mind, dear Silvia, would you like to earn more rewards?”

Why did Synth always want to make these challenges so difficult? Why did they always want Ember to be an active participant in her own humiliation? Because that’s what gets them off, a voice in her head said. They were getting off to Ember’s predicament. Fucking sadist. But somehow, it was hot too, that she had this kind of lure on this unknown internet-person.

“Yes, I would like to earn some more rewards.”

“In that case, before we can start, please accept the Erastos’ Expanded Monitoring settings. It will let me monitor your body during our wager.”

A new popup showed, asking Ember permission to start DeaDia’s expanded monitoring settings. Really, she had not much choice but to accept. Or she could forfeit, but she could give up on the dream of having three days without DeaDia.

“Now, with that done, let’s start. You’ve already gathered some interesting implements, and you might even have more toys lying around. Suggest a usage for them, and I will reward you accordingly.”

Synth really expected Ember to take an active part in her own torture. It was scary. She knew that if she suggested something too easy, Synth wouldn’t let her get to the edge. But she might also suggest something way past what Synth had in mind for her. She eyed the items Synth had her gather. Her eyes were drawn to the clothes pegs. Once, a long time ago, she had experimented with pain during sex. If she was horny enough, she liked someone to pinch her nipples, so a clothes peg on her nipple was the logical continuation. As soon as she had let go of the clothes peg, she knew she had made an error. She couldn’t remove the pinching implement quick enough. That had ended her previous dalliance in combining pain and pleasure. But now Synth had her force some kind of pain on herself. But not the clothes pegs, not yet.

“What if I hit my ass with the hairbrush again?”

“A little boring, but sure. Each slap will earn you five seconds of pleasure. I will set the intensity based on your effort.”

“Okay, I will slap each ass cheek five times.” Fifty seconds on medium should get her closer to the edge. Probably not enough to get close enough, but she’d make the most of it.

Once again, she took the hairbrush. Turned it around and slapped her ass. Five times on her right cheek. She started to feel the sting, her ass felt hot, like it was radiating its own heat. Then she moved to her left hand. This was a little awkward, she was not as ambidextrous as she would have liked. Awkwardly, she tried to slap her left cheek. The blow glanced off. Not hard enough. Once more, this one connected and she felt the sting on her left butt cheek join the one on the right. Four to go, three, two, one.

“I’m done.”

“Well done, here is your reward. Try to be a little more creative next time.”

The Niobe buzzed to life. No ramp up, no warning, one second there was nothing, the next second Ember felt as the fake cock vibrated inside her. She pushed the toy against her pussy with her hands, trying to make the most of the vibrations. The previous edge was long gone and she had to build back up to it. Not easy in this combination of pleasure and pain. The sensations started to build, her pussy the epicentre of her pleasure. And just as soon as the vibrations started, they were gone. Ember let out a sigh of frustration.

She once again looked over the items on the table. Clothes pegs? No, not the clothes pegs. Maybe the spoon? She could hit her ass with it again. Its surface area was smaller. It would hurt more. Maybe…

“I will use the wooden spoon on my tits.”

“Interesting, go ahead. You will get ten seconds for each hit with a high enough intensity.”

She looked at the spoon. Readied it. She should just immediately hit hard enough. No use in being soft on herself. Being soft didn’t earn any rewards.

“Fuck!” she exclaimed. The spoon had hit her hard nipple. The pain was more than she expected. But it started to diminish rapidly. Other side. This time only a small hiss of pain. Twenty seconds gained. She needed more. Left again. She braced herself for the impact. It still hurt. Right. Left again. Right again. Left. She moaned as the wooden spoon struck her nipple. Surprising herself. Was she getting off to the pain? Right. The impact hurt. But as soon as she took the spoon away, a warm glow radiated out from her breast. Two more, she decided. Left and right in quick succession. The pain in her left tit didn’t have enough time to dissipate before she hit the right one. As she fumbled to get her phone to inform Synth. The Niobe started up again, more intense than the previous time. Synth was pleased by her performance. Or it was an illusion, the pleasure so quick after the pain, the contrast increasing her sensations. It did work. She rode her hips against the device. The pleasurable toy. She’d earned it. The pleasure spread out from her pussy. Past her warm buttocks. Creeping up to her poor abused breasts. One hand pushed the Niobe into her pussy, the other was massaging the pain away. It worked. It worked very well. She felt the orgasm coming. It radiated from her pussy. From her warm buttocks, from her massaged tits. If the circles would reach each other, she would cum, she knew it. The Niobe buzzed on, guiding her closer and closer, herding her towards the edge. She could see it approach, could feel it. A little more and she would topple over. Close, so very close.

Fuck, too close. She would cum. She had to remove the device. Allow her pussy rest. Her fingers hooked behind the device, just as it died down. She let go. The feeling of the fake cock entering the few millimetres back inside her made her convulse involuntarily. Close, almost too close.

“Ooh, that looked like a good one. Want to go again?” The Niobe buzzed for half a second and Ember already felt that she was nearly back on the edge. This was a dangerous game she was playing. If the Niobe hadn’t stopped when it did, she would have orgasmed. She was sure of it. Did she want to go again? No, she didn’t, she wanted to cum. No, she didn’t want to cum, she wanted to win. And there was only one way.

“So, what’s next?”

“Another round of pain and pleasure, I think. There’s still an item you haven’t used yet.”

The clothes pegs. Maybe it was time. Her nipples still were warm from her own abuse with the wooden spoon. But there was something there. The combination of pain and pleasure. The undeniable heat spreading after each hit.

“I’ll do it. I’ll put the clothes pegs on my nipples.”

“Good girl. Now, your reward. Every minute you have a peg on your nipple, I will increase the intensity of the Niobe. And if you have clothes pegs on both nipples, I will increase it every thirty seconds. As soon as you remove the pegs, the Niobe will stop and it won’t start up again.”

Ember had already been planning to put pegs on both her nipples, she didn’t think she had an option to choose just one nipple to abuse. One hand absently stroked her hard knobs. The soft touches felt good compared to the sting of the wooden spoon. Just a little more. Her nipples had never been this sensitive. She felt that she might even be able to orgasm just by playing with her nipples. This was a new sensation. One she might explore somewhere in the next three days. The days that she would be freed from DeaDia, just three more edges to go.

With some trepidation, she took a clothes peg from the container. Opened its beak. That took more effort than she was expecting. One more stroke over her tiny tits before she put the wooden peg to her pink nipple. The effect was instant. Pain radiated out from her nipple. The only thing she could think about was to remove the peg again. It hurt worse than hitting herself with the spoon. With the spoon, at least she had a few moments of rest between each swat. This time, it was only the clamp and her nipple. She sat on her hands to prevent herself from removing the clothes peg. She needed to get used to it. She had promised Synth that she would get to the edge with clothes pegs on her nipples, and that is what she would do. After what felt like ages, the first pain subsided and she was able to feel the rest of her body. Just a little bit, everything was overpowered by the clamp on her nipple. Almost imperceptible, drowned out by the pain in her chest, she felt the Niobe vibrate her pussy and clit. Too low to distract her from the pain, way too low to get her to the edge. Synth knew what they were doing. Of course they knew. Starting low and drawing the moment out. The vibrations increased. The step was so small, that Ember almost missed it. If these were the increments, she would be sitting here for half an hour before the pleasure would finally overpower the pain.

She knew what she had to do. Part of her had known as soon as she read Synth’s message. But she didn’t know if she had the willpower for it. The container held more than enough clothes pegs. If she wanted, she could cover her body in the stinging things. But for this, she needed just one other peg. And her left nipple. Even slower than the previous time, her hand went to the container. Took out another peg. Forced it open between her thumb and index finger. The wooden mouth grazed her nipple and she had to use all her willpower not to jump back. No backing out now. The peg closed on her nipple. Agony joined agony. A few small tears formed in her eyes. And then she felt it, the vibrations increased. Still not enough to overpower the pain. Ember sat back on her hands. She couldn’t trust herself to remove the clamps. Once again, the sensations in her pussy increased, and she started counting down from thirty. Distracting herself, focusing on her pussy instead of on her poor nipples.

Ember couldn’t pinpoint when it happened, but somehow, the pain numbed down. It was still there, and whenever she moved, she could feel the pull of the clothes peg bringing all new kinds of pain to her nipples. But it wasn’t as overpowering or distracting anymore. Finally, she was able to focus on the sensations in her pussy. The Niobe increasing and increasing. She felt it build. No rest, no pause, just vibrations that kept increasing every thirty seconds. Bringing her closer and closer to orgasm. Just a little more, one, maybe two increases, and she would be on the edge. She knew it. Her hands went to the clothes pegs. Experimentally, she pulled on her right nipple. Pain and pleasure mixed. Intellectually, she knew this must hurt, but her body told her otherwise. Told her to do it again. So she did. She was rewarded with another increase in vibrations. She’d never imagined that she could cum from this combination of pain and pleasure. She was getting close though. So very close. Pleasure radiated out from her pussy, joined by her nipples. She was so close to cumming. She could just keep the clothes pegs on her nipples. Let herself be vibrated to orgasm. Would that be so bad? She ground her pussy against the toy. She… Was… Nearly…

She janked the clamps from her nipples. New pain, new pleasure. Her hips bucked against the immobile toy. Warmth spread out from her nipples. She stroked her poor, mistreated tits. Rode against the Niobe again. Fuck, she wanted to cum so bad. She felt like she’d earned it with this performance, but she still had two more excruciating edges to go.

“Cutting it close, aren’t you? So close while you still owe me two more edges. Part of me thinks you want to lose. Want to give in to me. But you know what? I’m feeling benevolent tonight, how about some more options. We can do two more edges, where you choose your own implements, or you can choose right now between pain and pleasure. In that case, you will receive one more task from me that will count for both edges. So, what will you do, little Silvia? Are we going to keep playing? Or will the next edge be your last edge?”

She needed to think on this. There had to be a trap. Synth wouldn’t be this forthcoming out of kindness. But it was so hard to think. She was continuously aware of her warm nipples, freed from their painful clothes pegs. Aware of the fake cock resting motionless in her pussy. Aware of the fact that in the last half hour, she had got to the edge three times, four times if you counted her own masturbation session before Synths wager, and she still hadn’t cummed. It would be so much easier to think if she just came. Maybe she should just start crossing off options, until the most appealing one remained. The first to remove was easy, she didn’t want any more pain. Her nipples were highly sensitive and she still felt the glow of her hairbrush on her ass. Two options left. Pleasure or two more edges where she combined pain with pleasure. She had already used everything Synth had made her gather. She might find some other items in her apartment, but she wasn’t sure that Synth would approve of them. She eyed the wooden spoon, she had already abused her ass and her tits. Just one more private part left. She could suggest hitting her pussy with the spoon. The thought made her wince. Even though the pain had increased her sensations, hitting her pussy was a step too far.

“I’m choosing pleasure.”

“I have to say I’m a little disappointed, I had hoped you were ready to choose pain. But no matter. Did you know that next to pain, pleasure can also be very overwhelming? I will show you in your next edge. First off, get rid of the Niobe, this one is all you. Secondly, I’ve seen that you like being filled up while masturbating. Fill yourself up with something that is not the Niobe or your fingers. Send me a picture and I will give you your last instruction.”

Ember removed the Niobe from her pussy, a string of grool between the fake cock and her pussy. All the distractions had kept her from realising how very wet she was. Now, to get something else to fill her back up. She didn’t have any toys. Hadn’t needed them, her fingers had been more than enough. If only she’d bought the same toy Linda had bought, she would be ready. She wanted something round. Something thick enough to fill her up. Her eyes went to her brush. The plastic handle was a nearly round oval, about one and a half times as long as her palm. It was nearly two thumbs thick. Thick enough to fill her up, not too thick to be uncomfortable.

The picture she sent showed the green brush poking out from her naked pussy, her lips closed around the handle, the actual brush part sticking out. Her lips were pink and glistened, her clit engorged. Her wet pussy had readily accepted the implement, her walls gripping the plastic.

“A Hairbrush. You’re more naughty than I thought. I had expected a vibrator or a dildo.”

“I don’t have one of those.”

“We should rectify that. Anyway, here’s your final instruction: Get to the edge and stay there for three minutes. Losing the edge means a forfeit, as does cumming. Have fun!”

Was fun the same as pleasure? Most of the time, for most people, it was. But was it for her? She couldn’t deny that a lot of the challenges she had done had an element of pleasure in them. She had done things she would never have done, experienced sensations she wouldn’t have explored on her own. But was that fun? She was forced to do these challenges. Forced to send pictures of herself in compromising situations. But part of her also liked the attention. Felt honoured that her pictures elicited horny responses by complete strangers. She also felt honoured that two strangers were so interested in her that they would give her challenges each day. It was hard to determine, especially with a hairbrush sticking out of her pussy. A pussy that screamed for an orgasm. After this wager she could orgasm. And then, the next three days, she was free to do as she wanted.

Ember pinched her nipples. Her fingers reviving the sensation of the clothes pegs. Immediately she felt her pussy react. She wanted this, she needed this. While her left hand played with her nipples, her right hand went to her clit. No need for foreplay any more. She just had to get to the edge and hold it. Pleasure spread out. She hadn’t gone far from the edge. She welcomed the sensations. Her left hand dropped down, grabbed the hairbrush, started to move it in and out of herself. She was fucking herself. Pleasuring herself. Her pussy gripped the plastic handle. Reluctant to let the sensation of being filled up go. It didn’t take long before she felt the sensation of an inevitable orgasm approach. Her movements became quicker, erratic. So close, but she needed to get closer. The brush pounding her pussy, her fingers a blur over her clit. She was going to cum, she knew it. She let go. Another orgasm prevented on the edge. An edge where she had to stay. Her finger touched her clit and she jerked towards it. Too sensitive, she would cum. By force of will alone, she prevented herself. She was on the edge. She didn’t know how much time had passed. How much time still needed to pass. The sensations died down a smidgen. That was just as dangerous. She pushed her makeshift dildo further inside her, welcoming the sensation. And let go, pushed again. The microscopic fuck was enough to keep her teetering on the edge. She continued, one time with the brush, another time a small stroke of her clit. Poised on a tightrope. Lose the edge, lose the wager. Cum and lose the wager. There was only the edge. Only the sensation in her pussy, in her body, in her warm cheeks, her hard nipples, her glowing ass. Minute movements to stay on this peak of pleasure. She had to stay here, had to keep edging. The small movements lost their effectiveness, and she increased the strokes of her hairbrush. Almost too much, the sensation immediately overpowering. Her other hand went to her nipple, put her nails to the knob and clamped down. The pain the only thing preventing her from cumming. She couldn’t take it any more. She had to cum, she had to come down. Three minutes must have passed.

Ember let go of the brush. Let go of her nipple. She was at her limit. If this wasn’t three minutes, Synth had won. Ember didn’t care. Her body was exhausted, overstimulated. Every small movement created its own excruciating sensations.

“Well done Silvia! You almost doubled the required time. I’ll be sure to keep that in mind for next time we play this game. You owe me no more edges.”

She had done it! Ember had beaten Synth. She had avoided all the traps. She didn’t need to edge any more. Her hand went to the brush that still filled her pussy. She could remove the handle, no more obligations. Slowly she moved it from her pussy. It started to feel empty, her walls longing to feel filled up. It couldn’t hurt to put it back one more time, just to quench that feeling. Ember let out a moan as she felt the brush fill her back up. Moved back out until it was almost out, pushed it back in. She knew what she was doing. She was fucking herself with this brush, even though she didn’t need to any more. It was just feeling so fucking good. She could masturbate without pressure. She could get to the edge, or even cum, when she wanted to. The wet sounds of the brush filling her pussy filled the air. Her other hand went to her clit. Started rubbing it. It didn’t take long. The accumulated frustration of so many edges without cumming had built up a reservoir. She felt as the cracks of her masturbation ruptured the dam. A tidal wave of pleasure. She humped the brush, humped her fingers. Moaned out loud, not caring that anyone could hear her.

*Wager completed. Winner: Synth