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It can feel like a snapping rubber band, to a sun burn to being tickled depending on the area you are getting it done. Over bones like the spine, collar bone, ribs or wrists tends to hurt the most for people. Meatier areas like butts, thighs or upper arms tend to be a dull ache for a lot of people. BF ran a full range of 'crap that hurts a lot' to 'stop that tickles' with his back piece. You may also bleed a lot or a little depending on your body set up, any medications you take or if you have been drinking. A lot of artists won't tattoo people that have been drinking because they a) are probably making an unsound judgment and b) they bleed, a bunch, and that can make the tattoo ink not hold in the skin.
BF's artist talked about wanting to give some folks small 'invisible' tattoos (use the tattoo gun without ink) so they could know what it felt like before under going a full tattoo. That might put a few people at ease but it might just be more of a time waster than anything.