I'm a big fan of the side jobs as the Developer may have Sophia push her "comfort zones" since she will be leaving soon and will probably never see those characters again.
The old men are giving her a sexy nurse uniform to wear, which I'm sure she will since she already seems to have no issues with dressing up and showing off. Since she's already seen them naked and even washed them, I think that the old pervs will take some Viagra beforehand and at a minimum have Sophia watch them jack off. I don't think that Sophia will give her first blowjob here, but perhaps the old gents will trick her into giving them hand jobs. That's the best I think that can happen from that interaction without Sophia crossing that bj/sex line which will of course effect all future scenes.
The tutoring job is a more interesting situation. She has already touched their dicks, "involuntarily" gotten them hard, and even rolled condoms onto them and showed her boobs and panties. Where to go from there? Firstly, they talked about her wearing some sexy lingerie, and we all know that Sophia has no issues with dressing up so I think that at least will happen. Secondly, I think the boys are a little more savvy and less innocent than they let on. Maybe they try to blackmail Sophia into doing more by threatening to tell their mom or even reporting her. They know that she could get in some pretty big trouble and even more so if they were smart enough to secretly record the last session by hidden camera. Oh, man, that would be great. Also, every time Sophia has an interaction it always seems to go a little farther so this one is hard to say. I'm sure she'll dress up and model, I'm pretty sure that the guys will get hard again and since things usually seem to progress a little, will they jack off in front of her, or maybe say that they don't know how to do it and have Sophia "show them how" by jerking their dicks? Good possibility. Only wildcard here is the blackmail idea and if they can coerce her, this could be a pretty transformative scene. Also, Dev could just end anything from happening by having the Mom walk in and stop it all. We'll see.
One thing that I want to point out is that while I share everyone's pain with the slowness of the rollout, if Sophia starts sucking and fucking guys that are not her husband than the game and the story loses everything that makes it great now, the teasing and sexual suspense. Once that barrier is crossed we will have a game that will still be enjoyable but will be totally different.