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There are different options for some of the routes, depending on the choices you make, and other seem fairly set for now. I don't want to spoil it for you, but if you really want to know you can go to the Patreon page for this game and most of the characters have route guides and mention what choices you can make to influence things (when and if that route has multiple options).
I have played all routes so let me of some assistance!
Spencer: You can top and bottom depending on confidence scores (to be on bottom choose choices that are not confident)
Harold: You can only top
Dozer: You can only top
Darius: You can only top
Chester: You can only bottom (atm, if you choose you want to top Chester, you actually skip the sex scene, so I am incliined to believe that eventually all the routes will have both options otherwise this route wouldn't show the option if all it does is skip the scene)
Well to know what I did differently, I'd need to know what others did. There are only a few things that seem to stand out to me.
1) I always supported Dozer and let him know he is huge all over, even his dick (which he thinks is on the smaller side). I also had no problem with me or others checking out his muscles.
2) I checked out Spencer when I visited his place. Later I admitted this to Dozer at the park. As we talked I made a choice and Dozer implied he might be open to a 3 way someday.
3) At the ski lodge, as we worked through the different temperature hot tubs, I let Dozer know I had no problem letting a couple other guys who we in there check out the Dozer's muscles. When we switched hot tubs, I let him know I over heard the 2 guys whispering that Dozer was huge "all over".
All inall, him topping me and then him getting me top him was a really great scene.
Yeah I eventually got the scene as well. The only difference I made in both plays was the conversation during day 21 or day 22 when Dozer is teasing MC and mentions about being on top.
Originally I had the MC reply that he wanted to top Dozer and that led to the scene at the ski lodge with ONLY that MC topping Dozer scene I mentioned in the original comment.
I replayed his route and chose most of the same options as I did originally and the only change was during that topping coversation where this time I said MC wanted Dozer to top. This led to flip flop ski lodge scene (I agree it is a great scene!)