Not all tattoos have to have a story, but all tattoos do have a story.

On the spectrum of tattooed-ness, I'm probably lower-middle.  Currently working on a left arm sleeve, with designs from the Lindisfarne gospels.  Three mid-size pieces lined up my spine (Tara, Odin and the bee-headed mushroom shaman).  A decent chunk of my left calf with a dragon.  Plus a few smaller, older bits here and there.

First question:  yes, it hurts.  Sometimes it's hard to say what 'hurt' is, though.

Second question: depends on what you mean by meaning.

I mean, what is meaning, and does a tattoo have to mean something?

A probability field collapses under observation.  Before observation, a probability field contains all possible paths between two actions, two states, two conditions or locations.  Under observation, the field collapses into the one outcome that is recognizable as this particular moment.

The collapse of probability instantiates this essential moment.  The collapse of aesthetics precipitates poetics:  first as memory, with the psychogeographic valence of quiddity.  The aesthetic field collapses under the vector of mortality, what elsewhere I describe as the vectors of scale.

Most mornings before work, I go to the gym.  Some of those mornings, I will exercise.  others, I will sit in the steam room and sweat out the dual ill humours of melancholy and gluttony.  The smallest movements impress sensation on my skin, like I'm immersed in this hot alchemical retort.  My arms shape  whorls, define swirling patterns  cascading in the steam.

This I think is what it's like moving through the collapsing aesthetic field, the poetic aura.  Getting tattoos is structurally resonant with  the collapse of the aesthetic field, which is probably why it hurts so good.