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1. A function to add that a position could be played as many times you desire, but as soon you choose a later one, that previous position should be blacked-out. For instance if there is a "clothed position" you might want to use more than just once, or something similar, but later on, it would be weird to go back to that one. Instead of just play it once and then have it unavailable.
Yes, this is a thing we already discussed internally. Could be problematic if the "entry position" with no/minimal required arousal is disabled.
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2. Make it possible to take your buddy with you on Holiday. As it is now, I've a couple of threesome ski-scenes that I can't reach atm, just for an example.
Noted. This would raise the price for the flight ticket. Significantly.
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3. When you call your buddy to your home and then hit the town, it feels unecessary that he must ask if he can join you, otherwise, why did you call him? So maybe you could remove that particular feature.
Well, you could need him only for the whore scenes.

Taking your gf or your buddy with you is programmed alike at the moment.
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4. Bigger window for the dream-sequence or an option to at least make it bigger.
Noted.
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And a question, works the buddy-feature at all locations? Bitch, Handyman, Hospital, etc...?
It should. Randomly selecting a scene gets the "buddy with you" flag as input parameter, for any location. That's the reason you can now take your gf to all locations, too. Gf and buddy share code, see above.