Disclaimer: I'm speaking as an older member of the "establishment" here.
Whenever I see someone with a tattoo all I can think of is, "How are you going to feel about that in 10 years, 20 years, 30 years...". Tattoos are very trendy right now. But trends are constantly changing over time. You can change your clothes, the color and style of your hair, the car you drive, etc., and none of those things are permanent. Most people as they get older (me included), look back and laugh and think "I wore that?". But I don't have to wear "that" anymore.
Not so easy with a permanent tattoo. What's a trend now may fade in a few years. I'd think about that before making a permanent change to your skin. Whether or not your tattoo has a story is irrelevant, I won't know it from looking at it. And chance are you aren't going to tell that "story" to everyone who sees it. So people will make their own assumptions of what your ink means. They won't all be favorable.
And yes, seeing someone with a tattoo immediately affects my perception of them. At the very least, I assume they have limited foresight and likely poor judgement.