I think it's really hot that there is a route where Kenny helps the mc
And if we get the option for a threesome in the future, I'll take it straight away lol
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That possibility was always from the start of the game which required two actions. Derek first tells Kenny of his plans and how Derek reacts with the bullies on the beach early on in the game.
Now the only real question is how to achieve "sharing" of Kasie. Yes, Derek and Kenny talked about Kasie getting pregnant, but I think that was just content reaffirming that there was a sharing plan in motion. No tags, yet, listed about pregnancy but if there is that aspect am sure the dev can slip it in toward the end of the game.
Ok, so when where and how a sharing can occur? Well, that is up to the dev really. If the story line and plot is well thought out, any number of possibilities arise, but first, all the boxes have to be checked so as not to taint the plot and story line. The easiest answer is a major event that shakes up all the relationships. Kasie's current mind set will not allow sharing because she is aroused... however while the three there at the resort a mini event occurred where both Derek and Kenny played around with her a little and Kasie let it happen. Why though? Honestly I think a little of Kasie's timid nature to say no and liking it was the reason behind it. Pretending to be asleep simply allowed Kasie to have plausible deniability. But as to a major event to put a sharing into motion--? Perhaps the boys can save Kasie from a mugger (yah, lame and stupid and not well thought out) but whatever the event is it would have to be traumatic. A lesser event could do it too though.
Instead of the old trope of "Truth or Dare" getting out of hand, the Three could buy a "drinking game." Some folks out there know the type of games like that you find at adult stores. The added advantage of that possibility is the dev can invent the game and have fun with it. Furthermore, if another D&D game night happens before the drinking game and Derek is the DM, it makes the drinking game more viable since all three would be more comfortable. (FYI, why Derek as the DM, simply because Derek is the one pushing the corruption of Kasie and would be less intellectual and more conniving.)
Or it could just start out with Derek and Kasie making out with Kasie thinking Kenny is asleep. Derek gets her very aroused when a Kenny pretending to be sleeping slowly joins in and there is your sharing 3-some with sloppy seconds and the works. And being young the boys would have greater recovery times so while one is recovering the other is busy at it...then around two...three...four... The fun of that is the next day of a Kasie cursing how sore she is from the night before