OK, so, played it through, and thoughts:

Premise: It's kind of cute, but it doesn't seem to know whether it wants to be rapey or consensual. Some of the boys are really into it, some aren't, and none of them knew what would happen when going in. I don't know if I want it to veer more in either direction or just stay vague.

Story: Enough to get us going, but not so much as to get complicated. It manages to not veer off into weird, insane stuff or attempt to be "epic" or "tragic" like so many furry things do. So kudos for K.I.S.S.

Characters: Shallow, but there's enough there to where we understand them and who they are, and the variety means that most guys can find one or more characters they wanna see get fucked.

Questions: I'm really surprised and pleased at how diverse the questions are. I used to play a lot of Jeopardy and Trivial Pursuit, and I still found myself having to look some of them up. But that brings up the problem, you really have to cheat to win due to the diversity and variety of the questions. I'm sure there are people who could win without cheating, but I'm not sure they're the kind of people I want to hang out with.

Art: It's serviceable. It gets the point across and it's never un-sexy. It could be better, but it gets the job done, and that's enough. Also, no massive glaring broken arm/leg anatomy errors, that's better than a lot of professionally produced hentai.

Conclusion: I had a good time, and probably would have even paid for this if asked. Replay value is lacking (there aren't many outcomes to see) but it's good for about an hour of fun. I'm hoping the creator does more work like this in the future, because it would be nice to have more proper furry "games" to fuck around in. I'm also really pleased to see how much mileage he got out of Ren'Py, which I'd always thought could only be used for dating sims and visual novels.

Suggestions for the future, although I dunno which of these are possible in Ren'Py

1. Allowing the player to select from the cast. I understand that creating your own avatar would be too much work, but letting the player choose from a list wouldn't be too bad and wouldn't change the rest of the game, since the characters all only interact with Jack. Plus then you can fast-forward to a "bad end" if you wanna see a particular character get fucked.

2. Depicting the character sprites inside the cage instead of having the cages in the background. I understand you can't have them interact with the background due to the limitations of the software, but showing them imprisoned, while it would cover up some of their sexy bodies, would at least let us know they're in the cage instead of standing in front of empty cages.

3. More boys, less clothes. Basically have more guys eliminated more quickly so we see more fun stuff. Something to consider in a future version.

4. More extreme-ness, maybe? I don't know if this might turn people off, but seeing the losers do even more crazy, kinky, fucked up stuff might be fun.

In sum, I had fun, and I look forward to more works.