Last word I read from OBD on pregnancy was that there is currently one pregnancy planned to happen at some point. He would not confirm who gets preggo other than to deny that it will not be Jessy. I asked... he said no, not Jessy. So, it is still a mystery for now.
Good luck with Dee! Mama Della and Stan have both earned their white hair, just like my long, white beard and half gray head. Della is most likely past the age of menopause and can't get pregnant again.
I would hazard a guess that is the case with Tracey as well but the "Joe Dirt" ending says otherwise... Speaking of that ending... If you haven't seen it go back to the scene with MC, Jessy and Tracey in her car early in game when they are discussing what to do about JD. If you pick the option to send him to prison instead of killing him (Yes, I prefer to savagely murder him too...) by reporting him to the authorities and sharing Jessy's home video of JD's actions you get a clever little side ending with some beautiful baby bump surprises. It's a light hearted, humorous ending worthy of being named the Joe Dirt ending.
I would greatly enjoy making all MC's girls pregnant, especially Jessy... She would look radiant with a big baby bump to match her bubble bum.
However, per Dimitri aka OBD we will only see one baby bump and he wouldn't say who it will be.
Adventure ever on my friend, Phat
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PS: Maybe it will be Sluggo's wife. Mickey and his ol'lady already have several kids but I don't think Sluggo is a papa yet and she is so fine you KNOW he has to be hittin' that!!! Go Sluggo Go!!!