Automatic Lover:

This is only an idea, but the idea is, that when moving the brown piston downwards inside the cylinder, the (blue) breast cups will suck at the breasts, and simultaneously the (light blue) dildo will grow.
The breast cups are made from e.g. Polycarbonate or another 'hard' & transparent plastic, but the dildo is made from e.g. latex or another highly flexible ( and thus inflatable- ) rubber.
Maybe it will prove a necessity to have two pistons, one for both the breast cups and one for the dildo,  but none the less, I think that the idea will work, when constructed in a proper way...