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The Challenge App: Week 2 - Day 10 [With Images] (Patreon)

Published:
2025-09-10 13:00:05
Imported:
2026-06

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Content

Things in the app are changing, and Ollie is starting to play the game a little more strategically. Is there a chance he's actually having fun now? Can he even be called a "he" anymore?

Files

Comments

Cynel

Well atleast s/he didn't get anymore penalties

J

> It was too risky. The punishment for an Extreme challenge… it had to be catastrophic. ...but then there is no punishment listed, we never know what fate Ollie is trying to avoid. Keeping with the app's theme, maybe something to make picking up guys easier? Upgraded tease, flintiness, bisexuality, increased libido, etc... Lots of options that would force Ollie's hand instead of just the promise of a lot of gems.

stger

I wonder if Olli got pregnant from the sex and this is why he might be stuck as a girl?

JohnManTD

i tried something a little different here without the punishment. the app is meant for a woman and doesn’t always have a punishment. the idea here is that ollie is starting to play by the rules more. he wants to get back to normal fast, so he’s willing to go to more extremes and play the challenges if it means earning more gems. in essence, waiting it out means being stuck like a girl for longer.

Infinity TG Captions

Just curious, what site do you use for the images? Love the story so far!

zoietta

I also miss the punishment aspect of the challenges! Obviously this one was a success, so the punishment would be temporary, but I still like the agency loss. To balance out that agency loss, why hasn't Ollie paid 10 of his 25 gems to remove the large breasts punishment yet? Surely he's tired of them by now, even though they've been helpful in the challenges! (If Ollie uses his sexed-up body to save up for a total punishment reversal, he'll put the app away and never touch it again... But if he goes bit by bit, he'll keep failing challenges and never escape!)