Some thinking...
Whitney: Pregnancy content with out secret softie of a rebel would be... interesting to say the least.
Dick Whitney I can see being certainly more protective of us, might even have some of their friends watch over us for protection. Do think alone time we could see a Whitney being reserved and kinda freaking out but being a bit more softer with us.
Knocked up Whitney would be PISSED. Mainly because they have to give up smoking and drinking, not to mention probably freaking out. But, we could calm them down and support them, earn more affection, while likely at the cost of them terrorizing us with public lewds. Hell, might even pawn us off as a stud to knock up others... (Can get behind that...)
Invite Whitners over: Comments on our room, should we have invested in stuff. Maybe shows a bit more of a softer side to them than publicly presented. Hell, could even have a event if Yandere Snatch isn't in jail yet and have Whitney catch them and tie them up and wake us up for some lewdy fun among the three of them. (Could be a good moment to maybe get Yanderes to be more open minded relationship wise...)
Dominating Whit: Now, I'm sure that maybe we might eventually get the chance to truly dominate or flip the switch with Whitney (same could be said with Kylar in terms of their jealousy), but I do hope we do get to dominate Whitney. See them submit to us, pleasure us, let us use them to our needs. And we can either return the favor to them for all they have done to us, or maybe be a little kinder about it but still have a firm hand.
Sydney: Pregnancy with our totally corrupt (I mean honestly who the hell keeps this church person pure?) lover is going to be fun as hell, specially with the temple storyline, which I am kinda digging.
Dick Syd: Could go for the holy virgin achievement with them, making all kinds of interesting. Sirrus would be shocked that they are getting a grand kid this young but would likely dote on us and become a second mom/dad to us, spoil us too.
Knocked up Syd: Again, Holy Virgin Pregnancy with Sydney would be epic, specially with Jordan finding out that Syd is preggers. Cause for joy, but Sydney and the MC knowing whats truly up.
Transformation Syd?: Given we can be a number of things, maybe we could help up changing Sydney in some manner? Like Wolfgirl Sydney? Who goes into heat big time and is needy as hell during it? Fun times.