OK, here are mine:
1. Purchased a silly blowup doll and lube once as gag gifts for a stag. Wasn't that embarrassed until I saw that I knew the checkout girl in the sex store. That was actually embarrassing for both of us.
2. Like many of you, I have been embarrassed purchaing condoms. But the topper of all time was when I purchased a pack
with the girl I'd left the bar with on our way to her place.

Didn't bother me at the time because I was wasted, but these days I cringe when I think about that one.
3. Purchasing my Flames away jersey. Normally not anything to be ashamed of, except I bought it near the end of last season.