Thats great to hear. I think having the confidence to try it occasionally is a perfect place to start. One that becomes more normal then hopefully not wearing a bra wont feel like such a big deal.
I love walking in winter without a bra, being lovely and snuggly whilst its chilly, but also with the freedom feels wonderful!
My gf has small, very cute breasts but quite big nipples. She's very self conscious about them and thought she'll not wear a bra in everyday life, why would she? , she feels she has to at work particularly as one guy is a little over zealous ...
My boobs arent small but my nipples are quite prominent too, I used to feel self conscious about it but now I never wear a bra (in my own time or at work). I think its just one of those things I decided to do and stuck to it, now its normal for me wherever I go. I understand the nervousness, but its best just to take the plunge.
There is nothing more attractive and exciting as some sweet puffy nipples of a good size, on a fairly small breast. It easily doubles the excitement level of their appearance ! And for some girls with only 'A cups,,,those huge nipples can make their breasts look almost double the size that they really are. The magic work of 'wonder bras' and what Victoria Secret can do is not all that bad.. But over all I 'd sure enjoy seeing more braless women, especially those with fit, firm tits,,be they very young nubile girls or older women who have kept them nice, firm, and tight all these years (without a lift or surgery too!). Checking to see if there is a discussion here on this group about surgically enhanced tits and how they look without a bra.
We've never had that discussion on here about fake boobs. Personally i'm not a fan, but each to their own.