Chapter 8
Does Brian add any punishment?
Just a commemorative photo
"There, now. That wasn't so hard, was it?" Brian's voice was dripping with an obnoxious amount of amusement that only served to further agitate Ali. "As an additional punishment for your little outburst, I'm requiring you to send me a quick selfie. Taken right now, as you are. Send it to me immediately."
He instructed her as she suppressed the desire to yell at him. He wanted a high angle, looking up at the camera. "And make sure you push your boobs out with your other arm. You know the way girls do that, thinking it's not obvious what they're doing. Make it look good for me. Oh, and cleavage must be visible. Take off if you need to, but don't put anything else on. You don't have to look happy about it, but you do have to do it.""
Ali's expression is irritated as she takes the required photo of herself. Hair disheveled from sleep, she pulled on her tank top to expose sufficient cleavage as she snapped the picture. She positively hated that it actually looked really good.
"Oh, and I've decided I don't want you moping around my house all day, so you'll keep your job. Surrendering your income to me, of course. So make sure you bring all your cards and any cash you have lying around when you come. Any time today is fine, just text me when you know. See you later."
Ali groaned and sent the selfie it to him grumpily, knowing her phone would go off soon if she failed to honor the rules of this weird game. The fucking bastard wanted her to work like a ****? And according to the rules, there wasn't anything she could even do about it.
She buried her face in her pillow and screamed until she felt some catharsis. Then, forcing herself to move, she rolls out of bed to get ready for work, trying to pretend as though everything was normal. If she didn't think about it, it was just another normal day.
Her shower was a welcome escape, leaving her feeling clean and refreshed. She'd almost managed to put Brian completely out of her mind as she dressed and prepared herself for the day. That was, until her phone went off again with the same angry notification sound from before.
"Challenge Failure: Ensuring His Satisfaction.
First-time Failure Consequence: Brian will now have the power to increase the severity of three of your rule categories, and you must request a punishment from him for your challenge failure.
Rule Break Consequence: +1 to the consequence roll for failing this challenge again in the future. (Current +1)"
Ali stared at the notification, not quite understanding what she could possibly have done. Then it hit her. He masturbated. He got off without her and she was going to be punished for it, according to the challenge she'd recklessly chosen for herself. No, no, no... that wasn't fair! What the fuck!
Angrily, she called Brian. "You bastard. Can't you go five minutes without touching yourself?"
Brian laughs. "What are you on about? Oh, I see... Well isn't that neat? I do that every morning, love. Really helps keep me focused. But it looks like you're in trouble for it. Shirking your responsibilities already? Tsk, tsk, tsk."
Ali seethed, gripping her phone so hard she worried the case would crack.
He continued. "Well then I guess you should hurry your sweet ass over here as quick as you can, because I'm feeling particularly excitable today. I might just go another round here in a few. Maybe I'll use your photo this time."
She was furious and humiliated at once, and she'd had enough of this. "Look, you fucking asshole. I've never particularly liked you, especially after what you did to Jessica. But this is insane, and hardly fair. You don't get to—"
"Hey. Shut up." Brian didn't raise his voice or shout, but his tone was suddenly firm, authoritative.
Despite herself, Ali stopped talking.
Brian continued, his tone calm. "Alright, bitch. This whole thing wasn't even my idea. You're the one who sent me this whole list of crazy kinky rules. So you know what? I'll decide what we do and don't get to do."
She opened her mouth to yell at him again but he seemed to read her mind.
"No more yelling at me, Ali. That's not exactly my idea of... what does it say here? My 'dream submissive.' Yeah, no. You want to be my dream submissive? You can start by only talking to me in pleasant tones. Nice and polite. You know I basically own you right now? Especially now that you've failed a challenge. Let's see what the rules say... I can change them now. I could make you marry me. Right now. How would you like to be my blushing bride? We could invite everyone you know. How does that sound?"
Ali could practically feel the cold shackle of his authority close around her. No more yelling, no speaking to him impolitely. It was officially a rule, now. If she lashed out at him now, the phone would just beep that she failed another rule.
She took a breath. She really did have to start playing along or it would only get worse. And he was right; she'd technically started this, even if she didn't know it was real.
"N-no. I don't want that.... please." She had to **** the word to come out when she really just wanted to keep yelling at the man. "...I'm sorry. Please don't **** me to marry you. I won't yell again."
Brian's smug smile was once again audible in his voice. "That's better. And I believe you have to ask me something as part of your challenge failure. So. Ask me." He sounded all too pleased with himself. It was going to be absolute **** speaking politely to him at all times.
The punishment. Internally, Ali screamed in frustration; it took all of her self control to remain outwardly calm. "Yes... I've failed a challenge." Taking another calming breath, she added, "Will you please punish me?"
The bastard let her question hang in the air for a few seconds, probably savoring it. Ali's heart pounded in her ears in that long silence.
"Yeah, okay. I'll tell you what. I'll go easy on you this time, since this one isn't really your fault: no underwear for a week. Bra or panties. Socks are okay. Oh, do you have any garter belts? Wait, that's even better. No underwear and you have to wear thigh highs with a garter belt every day. For one week."
Before Ali could respond, he added, "Now, for future reference, Ali: A good little submissive wouldn't think of saying anything right now other than to meekly accept my command. And maybe add something about how you'll do it, or how you want to do better in the future, or how you look forward to pleasing me, yadda yadda."
Another long pause while he waited for her to respond to his absurd request. Ali's deep breaths were the only thing keeping her from screaming at him. She contented herself with trying to give him the least-satisfying response she could. "Very well. I will quit wearing underwear for one week. But I will need to go buy a garter belt and stockings..." Her mind raced until she finally added, softly, "May I have today to do that?"
"Sure. But today doesn't count towards your week and you still can't wear underwear." She could still hear his smug grin.
She hated him already. More even than before. "...thank you. Good bye."
Hanging up, her sustained anger left her as a loud scream, leaving her feeling drained despite it being early morning.
The worst part was that she still needed to gather her cash and rush to his place in case he really was planning to get himself off again before work. If he could trigger a challenge failure just by masturbating... well, she'd just have to make sure he didn't ever feel like masturbating. She grimaced, knowing that was exactly what the challenge meant, and no amount of spitefully rising to meet that challenge was going to be any kind of punishment for Brian.
Sadly, quietly, Ali gathered up every cent of currency she had in her apartment and headed for her car.
What's next?
Fap Roulette Anthology
Anything can happen.
A collection of stories focused on the roulette games found at faproulette.co.
Updated on Mar 26, 2025
Created on Dec 5, 2024
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