Where Does It Hurt The Most? - Areas of sensitive skin (i.e., inside your elbow) and near bone or cartilage (i.e., on the top of feet & knuckles) tend to hurt the most. Everyone is different.
If it makes you feel any better, tattoo artists are aware of your questions and are more than happy to answer them. So, don't be shy. Given the areas of the body than can serve as canvases, it'll take more than a simple question to make a tattoo artist blush.
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If your tattoo is to honor someone else or to express your strong feeling to your loved ones, think about the things they enjoy the most and what message you want to pass on. Talk to a tattoo artist whom you respect and ask for suggestions. You don't have to draw the image yourself, but express your true feeling to the tattoo artists and listen to their suggestions.
Another thing you can think of is if you like art. What kind of artist comes to your mind, what kind of artistic design comes to your mind and everything that goes through your head. There are many people who use famous people such as poets, music artists and less. These days, I myself have seen many people use the type of tattoo graffiti on their bodies all the time.