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Yes, I've rented him out a few times. His current like is 35

I think you have enough like for him. If you said you have camp's moral (not Bandit affection, it's not the same thing) more than 25 and Green ending in Northcrest conspiracy event, there should be Belly fun appear in talk option.

Bandit camp morale is 90, I have the green ending on the Northcrest Conspiracy, Harold at 35 like and. . .no belly fun option even after sleeping with him again. I'm so confused

That's weird, have you tried to re-download the latest version again? If you already try and not work, please try to play with these save files of mine. Please read the instruction well to prevent your loss of game procession.

With Harold, is there supposed to be something that tells me I have Belly fun? It's frustrating because all I want is sex in my house with Barrel. I can't even talk to Barrel at the tavern any more, there's no option to go to him

For "Check on what the thug is up to" option, you need to have a love potion in your inventory. And another requirement is the same, you need to play in the green route of Northcrest conspiracy. And for Belly fun, if you sure you have all requirements met, it should be show in talk option like here.

I'm 100% sure I have all the requirements met. Next time I go on, I'll grab three screenshots to show you just how weird it is. 

I'm trying to just get the option with the wrestling with Barrel. He shows up and there's 2 options - fair fight and throw the fight. No matter what I pick, he never shows up at my house in bareshade.


All three things needed for Belly Fun to show up, and nothing.

May I ask, are you play this game in PC or Android?

PC

Have you try playing my save files? It should work normally with my save files.