I have one tattoo, a rose on my upper right arm that I had done when I was 18 (44 now). At the time (mid-80's) nice middle class privately educated boys like me didn't get tattoos (or at least not to the extent they do now). That was a big part of the attraction.
I have never once regretted it or wanted it removed / covered up. I'd never choose that design (off a flash card) now, and it's faded / blurred over the years, but it's part of me and who I was at the time. I've thought about getting another (custom this time) for about the last 20 years but havn't come up with a design I really want. May well get another one at some point.
Re: tattoos / piercings' greater acceptance these days. I work for one of the leading banks and one of the assistant managers (50 year old who spent the first 20+ years of his working life in a sawmill) in my department has arms covered in old school blue ink tattoos (he always wears a long sleeved shirt but they show through) and large holes in his ears (as referred to above somewhere, can't be arsed to look back to see what they are called). There are also a fair few guys in their 20's who are covered in tattoos – they are all fairly junior grades, but based on the AM I just mentioned I don't think their ink will hold them back career-wise….. to a point. I doubt any of our director-level managers have tats but who knows (cf: the partner in a top law firm with a swastika on his head as referred to in a recent thread).
Quite depressing to see the level of bigotry on this thread, though not entirely surprising.