Hypothetically, if someone is worthy of His Paradise, but enjoy receiving pain as they got used to it or other reasons, would they still not deserve Hell? I know little about Islam, so please do not assume my knowledge of anything and help with tags.
I think I understand what the OP is trying to ask. To clarify, here is my interpretation of the question:
If someone is destined to go to Heaven but they preferred pain, can they go to Hell instead from their own choice?
OK - so let's clear a few things first.
Let's focus on one word - preferred.
In Islam, everything which exists, from molecules, atoms, photons to celestial bodies in the Galaxy are all creations of Allah (God). Other things such as feelings, sensation and preferences are also creations. When someone wants something, it is because God has instilled in that person the ability to want that particular thing or experience, i.e. God put it there.
Falling in love is an enjoyful (for the majority - especially me) experience. God has put that in to place for me to experience it and I have the choice to experience it or not. Just like pain.
So just like in this world, the hereafter is all created by God. And as the comments suggest, the Pain in the hereafter is above and beyond the pain in this world. No one, not a single being will want it. There is a plethora of verses in the Quraan and Hadith which outline the immensity of the hereafter, both good and the bad.
Lastly - Anyone who enjoys pain in this world can be seen as an invalid - someone who is mentally ill. Therefore, the question here is redundant as no one sane would want to experience pain. Such a person will become sane in the hereafter and would most certainly aspire Paradise.
We do not know true and full concept of hell. Examples given in quran and hadiths are to make us imagine or try to understand afterlife. Allah created mankind. If He wants to punish someone, He knows how to punish it. If Allah created someone as enjoy the pain, He will punish him/her with unpleasant things to him/her.