When he asks you questions you do not want to answer, you could reply "that is a personal question which I prefer not to answer."
When he sends you pictures that you consider harassment (is this like pictures of pr0n?) you could reply "that picture is inappropriate."
It sounds like his contact of you is sucking your time and energy as you try to figure out how to respond appropriately. Again you are falling into the pattern of doing what you don't want in order to appease him.
You still have some fear of this person, so realize that this is a chance to work on courage.
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