I used to go really heavy on bench when I was younger, I loved it! There was nothing like repping 315 or 405. Years later, my shoulders and joints were tore up! Granted, thats with a lifetime of sports and other impact as well.
Now, I like to use other methods. I use primarily dumbbells for pressing, and usually thats on some incline. I only use weight that I can control and that *does not hurt! If you experience pain while doing a lift, its typically not good. Here are a few pointers:
-Go at a faster pace. Less rest makes your work harder but has many benefits. It will fatigue the muscle faster and give a nice conditioning effect.
-pre-exhausting can work wonders. I do this for chest often with something like the pec dec or some fly machine. Get a good pump, then when you hit your presses, the pump and focus is insaine, despite a little bit less weight.
-still hit your stabilizers if you use machines. You can do a plethera of things, such as face pulls or different holds. I also like to do a lot of bodyweight exercises, like push up variations that work a different type of strength. These are great to incorporate in there. Its a good compliment to machine work if the heavy free weights cause you pain. Often times, these type of things can help to "correct" the issue that is causing you pain. This could be due to a number of things, such as poor posture, muscle imbalances, weaker joints (tendons, ligaments) and so on. Look to correct your weaknesses and imbalances.
Dave Palumbo used to say that its not about the amount of weight that you lift, but the amount of weight that you make your musces "think" they are lifting. Food for thought...
Good luck! Just enjoy what you do and push for gains and progress. Thats what its all about.