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Chapter 5
Challenges...
No reroll.
Ali labored over the selection of challenges. Her imagination ran wild with each one, painting a variety of scenarios. Maybe she was overtired, or maybe she'd drunk more than she realized, but most of them were actually appealing to her lust-blinded brain.
Ensuring His Satisfaction? Ali would be expected to keep Brian so sexually satisfied that he never needed to masturbate or sleep around. And even if he did engage in sexual activity with another woman, Ali would need to insert herself into the situation. His sexual satisfaction would be Ali's primary purpose in life.
She scanned the list until her eyes fell on the words "Indoor Nudity" and she read the terms aloud. "You are not allowed to wear clothes when alone with him unless instructed. Furthermore, he has the right to demand you strip anywhere this is legally permissible! No clothing can be worn again until commanded."
Ali's face felt hot. The thought of being so totally beholden to Brian, the dickhead who'd hurt her friend so badly, filled her with such a shameful sense of **** lust. How could she explain any of this to Jessica? She wouldn't be able to keep it a secret from her friend... but she would have to hide the true nature, and openly defend Brian in all conversations.
The idea of having that conversation felt more shameful than anything else she'd imagined so far. Being Brian's submissive little fuck bunny was one thing, but betraying Jessica like that...
Ali hated to admit it to herself, but the knowledge that it would be a betrayal of her friend, and one that Ali would be helplessly complicit in, somehow made the whole thing that much sweeter. Maybe Ali really was fucked up. Maybe it was in her best interest to have all control over her life put in someone else's hands. Brian was an asshole, but he was successful in life.
Convincing herself that it was crazy to think any of this was actually real, and chasing the dark feeling of twisted delight she found in her imaginary betrayal, Ali clicked Ensuring His Satisfaction and, just because it made the whole thing that much sweeter to make it harder for her to back out, she also clicked Paying Your Debts and submitted it before she could overthink anything.
The screen moved to a summary of her choices.
"Challenges:
Ensuring His Satisfaction: Ensure he abstains from self-pleasure or engaging in any sexual acts with others during your service unless you are involved. Your duty is to keep him thoroughly pleased.
Paying Your Debts: From the time your challenge is active, he will keep a record of what he spends on you, including money you surrender to him as part of your other rules. If you choose to end the relationship at the end of your service period, you must repay this sum plus 2% interest. If you cannot pay this back in half the original length of the service period, restart the relationship with all rolls you had at the end, plus one to each."
Ali shuddered, imagining the extra twist of the second challenge. She'd added it on a whim, but it meant she might never be free of him. And any attempt to leave would mean crippling debt and further restriction until there really was nothing left of Ali but whatever Brian wanted.
The screen displayed a final message.
"All choices final. Your dominant is now being notified of the terms of the arrangement. We hope you enjoy your submissive experience. ~FR"
And then the screen went black, just like that. What an anticlimactic waste of time. Turning to look at the clock, Ali saw that it was nearly 5:00 A.M. and she still hadn't even enjoyed a single orgasm.
What's next?
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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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