I don't think it's so worrisome or that it was necessary to go to the dermatologist, but it can't hurt, certainly. After all, sometimes, a pimple can actually reach a stage where professional is needed.
Anyway, if you want it gone faster or if some residual smaller thing remains after the treatment or something, definitely try out a benzoyle peroxide product. It's the one best thing to apply topically to skin infections, be they caused by acne, ingrowns or something else. You'll be fighting the problem in two ways then.
Also, if you pop it, eventually, and you empty it, completely or not, it's important to apply some benzoyle peroxide product once you're done emptying it. By popping it, you open the door again. Make sure you use it for more effective disinfection, not leave it for the infection to be revived. Generally, that starts a process. You'll be more actively fighting the bacteria, which will accelerate the development of things, and "juice" will form again after a few hours, maybe. Then you'll go with a tissue, re-empty it and re-apply the product. After one or two times of this, leaving it for the day/night will allow you to perform maybe just one last treatment, and gone it will be, and off to the healing process.
And if it happens again, make sure you try the peroxide product first. It does miracles, sometimes. Those huge pimples deep in the skin, on my inner thighs, can be taken care of this way, even if it takes longer. It doesn't deal with the mysterious underlying cause that keeps spawning them in the area, but it takes care of the infection once it breaks out.
Oh yeah, one last thing. I'm not an expert in make-up, but I think I've figured something out. We shouldn't try to camouflage a pimple's texture with make-up. The colour is fine (though not preferable because you put even more stuff that'll block the port), but don't try to hide the bump. You'll need a ton of make-up to manage something, and even then, it will probably be quite gross to look at. Every time a girl has tried to camouflage a bump in their face, I've noticed it and found it "ew". Like the bump is still there, but doesn't look like a pimple anymore; rather like a caky deformation fused on the face. Possibly worse. Unless they were all doing it wrong, I think it's not a good idea to try this.