Does the high temperature cause "melting" of the silicone? If so, that significantly changes its material properties. Does the rest of the silicone get hot, too? Maybe you need to do a thermal analysis first, static second.
If this is a situation that you have tested in real life and you know that it penetrates the silicone, you could apply a forced displacement of the metal part (instead of 14 psi pressure force, you induce a displacement in the metal part and watch the results). This method might work if you know the average depth of penetration.
What you setup in simulation will be what you get. Solidworks may not know about the silicone's change in properties (lower yield stress, etc.) at higher temperatures even if you put in a temperature load into your study. Also, the type of study makes various assumptions for you (Is your study a dynamic study - with nonlinear material properties and such?). Try to think a minute about what you are trying to show by doing this simulation. Then think if you were to solve this by hand, what kind of assumptions would you have to make? That should point you in the direction of the right solver.
I hope I have been some help.