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Ok, fun with Caleb happened after I clicked Night with Caleb, and it was the alternative to sleeping. Sex with Caleb isn't appearing. I've spoken to both during the day and there are no options that aren't normally there. This is annoying lol. I do have Bernie on 4 hearts tho

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Did you speak to Bernard at night? And congrats on getting that far!

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Yeah. Three times now I've spoken to him at night and each time it just says Night with Caleb. I do it, and then we go to the barn and im given the option for fun or sleep and that's all

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OK I am gonna try and power through but it's gonna be a couple days at least. I'll keep you posted.

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Thanks!

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Do you have 1 heart with Caleb yet? I can't remember if it's from the fireworks or from giving him a treat (both new options in the Patreon version).
The option to talk to Bernard about you having sex with Caleb is in his talk menu during the day in the shop, not in his home at night.
Admit to Bernard that you've had sex with Caleb,  then that night suggest you two spend the night with Caleb, it will start off the same as usual, but then once you 3 bed down for the night the scene will diverge.

Thank you.

Yes, I did all that. However when I choose to go at night, the only options are fun and sleep, no sex. The fun that happens is usually a threesome of sorts, but its not what i was expecting.

So after getting the heart with Caleb, admitting to Bernard during the day that you had sex with Caleb, and then taking the usual picnic to the barn at night, you didn't end up with an oral 3some?

The threesome i had with the "fun" option was that bernard takes you from behind and you have the option to play with caleb from the front or take him from behind too