How old were you when...?

[miloandtock1]

Ok I'll bite...

1. How old were you when you first got to pick/out buy your own underwear?
About 14 or 15.
2. Did you want to gravitate toward snug-fitting briefs?
It was the early 80s, and Jim Palmer Jockey Underwear ads were pretty common, so Jockey elance and Micro3 bikinis were my first non-white briefs.
3. Did your parents prefer that you wear something bigger, as in loose-fitting boxers?
Neither said anything, Mom actually encouraged and bought them for me too.
4. If so, how did you deal with that?
5. How did you deal with all of this dressing for gym, as in PE class? Were you different from your friends?
I was not alone, by 8th and 9th grade a lot of guy were wearing them.

Extra credit
What were the circumstances where you got to wear your first strap (as in athletic supporter)?
Only wore jockstrap back in 3rd grade when I took karate/judo lessons. We had to wear one provided with protective cup. Never wore one since.