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Chapter 4
Which version?
Long Term Surrender
Ali tapped the button for Long Term Surrender. A disclaimer immediately popped up warning her that this could be a big mistake, and to think carefully before... something. She didn't finish reading it before dismissing it to get to the good stuff.
She clicked the "Play Now" button and watched as the screen faded to black and then displayed fourteen ominous words.
"Good choice, Ali. With luck, it's the last one you'll ever have to make."
It unnerved her that the site could somehow know her name, but before she could figure out how to close it, several little 6-sided dice jumped into the screen and rolled around, jostling and bumping against one another.
The first settled on 6.
"Who. The very worst ex among all your friends' exes. This has been determined to be Jessica's ex-fiancé, Brian. He will be notified as soon as possible at the end of your rolls."
Ali tilted her head, confused. All thoughts of masturbation fled. "What?" There was no way this site could know so much. Her name, that she had a friend Jessica, who had a former fiancé named Brian, or that he was a sadistic, cheating asshole who nearly ruined Jessica's life with his gaslighting and manipulation.
Another die settled on a 4.
"How long. 24 months." There was a little paragraph beneath that Ali didn't quite read. Something about another roll in the event that her Dominant wished to end the arrangement early.
"Uh, what? I want to end it. Right now. This isn't funny."
Another die stopped rolling. 4.
"Commitment. At his option, you must relocate to live with him and either resign from your job or surrender your entire income (his choice) and become financially dependent on him."
"Eww! What? No thank you, random web site. There's no way I'm doing that." Ali couldn't find any way to stop the presentation on her screen. The X was missing to close it, and no keys seemed to be doing anything. Besides, now she was morbidly curious about what it was even going to say. The site was creeping her out but she couldn't look away now.
Another die landed on a 5. Ali winced. She had already worked out that higher numbers were less pleasant outcomes.
"Fidelity. You are to refrain from engaging in social conversations with strangers. You may not be alone with any person of your preferred gender (male) without his approval. You may not indulge in any form of pleasure without his explicit permission. You must avoid any media that arouses you. You must abstain from any romantic or sexual activities with anyone other than your Dominant."
Ali began shaking her head as she read the words and didn't stop shaking. "No. No, no, no. That's insane. What kind of weird site is this? Who even made this?" She was still shaking her head when the next die stopped, this time on a 6.
"Romance. You must defend his actions, no matter your personal beliefs and persuade others that you are the ideal couple and conceal the true nature of your relationship from others. You must invest significant effort into gifts, anniversaries, etc. You must engage in public displays of affection and embrace all private activities typically conducted by couples."
For all his faults, Brian was a really hot stud. Jessica had said he was hands down the very best sexual partner she'd ever had, that he could fuck her so well that she'd forget why she was ever mad at him. As she read the line about being required to engage in 'all private activities typically conducted by couples' she couldn't help but bite her lip, finally finding some merit to the fantasy playing out before her. This painted a picture of her being Brian's sexual plaything. His devoted little girlfriend and willing sexual conquest. Despite herself, and despite all the terrible stipulations that went with it, that thought turned her on.
The next roll was a 3, maybe it wouldn't be so bad.
"Control. Hand over your house and car keys; he now controls your personal spaces. Honesty is non-negotiable; you will extend to him the same level of truth as your closest confidants. And transparency is your new virtue. He will be given unrestricted access to your secrets, your social media, and inner thoughts."
Ali's mouth fell open. "What? Now how is that supposed to even work?"
The dice were stopping faster now. Another 6.
"Being the perfect submissive. Craft your appearance to his liking. Your words and actions reflect his desires. Engage in activities he prefers. Dress according to his preferences. Be his dream submissive, devoid of imperfections. Maintain this role consistently, even in his absence: this is your new identity."
Again, a shameful lust rose within Ali. Something deep inside her loved the sexual elements of this bizarre little fantasy game. Being Brian's submissive little sex doll, dressing and acting however he liked, building her entire life around his simple satisfaction... Ali desperately wanted to touch herself. Why wasn't she touching herself?
The next die stopped on 3. Mercifully, a somewhat low number.
"Service. Your Dominant's housework is your duty. Run errands as an extension of his will."
Ali looked down at her glistening panties, soaked through with anticipation. Normally she'd be two knuckles deep in her snatch by now, fingering herself silly. A little warning bell went off in the back of her mind as the last die stopped rolling on her screen.
4.
"Sex. You will engage in any of his non-**** kinks. Mild kinks, light bondage, and swallowing are part of your duties. Anal sex is expected, and all vanilla sexual activities are standard."
Ali barely gave that screen any notice. She couldn't explain why she felt such trepidation about touching herself. Something was definitely wrong but she couldn't put her finger on it. She was starting to panic. With a deep breath, she **** all concern from her mind and, just to convince herself she wasn't losing her mind, **** her fingers down her panties to gently grind against her eager clit. Once the strange mental barrier had been crossed, she was able to enjoy herself freely, relaxing into her chair as she fantasized wildly about Brian, of all people.
The screen changed immediately to review the set of rules she'd rolled. One line was brought to focus over the rest.
"You may not indulge in any form of pleasure without his explicit permission."
"Warning: masturbation constitutes breaking a rule and you will be subject to punishment."
Ali swallowed, hand frozen in place. Was this real, somehow? This random web site couldn't possibly know any of the things it had already shown her. Could it see her? Was this web site actually binding her to Brian in some god-awful way? To become his perfectly submissive little plaything for two years?
She broke out in a cold sweat as the screen faded to black once more, only to light up with more text.
"Challenges. You must select one challenge. You may select two additional challenges to reroll your results, or three additional challenges for two rerolls."
Reroll? Redo all rolls? That sounded like the very thing Ali would need if in fact this whole thing was actually happening. Ali didn't discount it entirely, but her rational mind struggled to accept that the web site had any ability to actually do anything she was looking at.
On the other hand, there were pretty stiff penalties for failing a challenge that were enough to give Ali pause about selecting more than necessary. Even if this was all real, there was no guarantee things worked out any better and then she'd be stuck with three or more crazy challenges she'd have to live with. And the challenges themselves were not exactly for the faint of heart.
But it would give her a chance at a new person altogether, which was her primary concern... or was it? Brian was fairly wealthy, sexually aggressive, and admittedly pretty damn hot, other shortcomings aside. Ali looked at the results she'd rolled; many of them were sixes, including the one that had assigned her to Brian. Would it be worth it to reroll, right?
Of course, that meant selecting multiple challenges on top of the one mandatory choice.
"These challenges are intended to be highly demanding."
Why did this whole dilemma turn her on so much?
Challenges...
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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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