I had some stuff to attend to at a nearby larger town. Given that the place I live has about 2 small shops that sell clothes, I thought I would take the chance to go shopping while I was there. So far I haven't really been too bothered about trying more feminine clothes. There are some styles/clothes that I really want to try, but like quite a few women in my family, I'm also quite happy in more androgynous clothing so it hasn't been a pressing issue. Also, money.
I was wearing black jeans that look kind of feminine even though they are technically mens. I also had a brown shirt and a grey jumper which mostly hides my bumps. Though the backpack I was wearing pulls my clothes a bit tighter and pushes the bra cups together a bit more making them far more noticeable. On the way to the shops one guy I passed gave me a sort of odd look, but I don't really know what he was thinking so I didn't care. No one else seemed to notice anything.
I started with some more jeans since I only have 1 that I'm happy to wear. The others are sort of old and past their best. I was fine till I got to the fitting rooms. Women to the left, men to the right. For a moment I froze and panicked. There were 2 staff watching. I should note that I don't really have a 'male' or 'female' mode of presentation. I am just me. So, not really sure of how the people around me were seeing me I went to the mens section to 'play it safe'. No one said anything. Then I realised that if I were to try going to the womens fitting rooms now, there might be questions. After debating it for a minute or two, I decided that if someone said something, then I would just say I went to the wrong rooms the first time in a bit of a derpy moment. I'm usually quite anxious about that sort of thing, but I was there as part of pushing my comfort zone and 'growing up', so I decided not to hide from it.
When I came back later with more jeans to try (the first ones were FAR too small. The label lied, they were NOT 81cm waist) I went to the womens rooms. Same staff said nothing. I came back with a third load of stuff to try (shirts, sports bras and bras) and again nothing. By the time I had finished trying them, it was a few minutes from closing time. I was quite warm and didn't really want to put the jumper back on. Given how well things were going so far, I decided to try going around without my jumper on, which meant the shape of my bewbs were quite visible (esp with the effect of the backpack straps). Bit of risk, but wanting to find the boundaries of what I can do atm overrode the anxiety. Some staff were in the changing rooms to make sure no one was left in there. They just mentioned to put anything I didn't want on the table outside and that the shop was closing soon. No issues

Paid for the jeans and left. Walked around town, waited at the train station and got the train home without any looks/stares/comments. Feeling quite happy I decided to get some cookies from a supermarket on the walk home. I was in the bakery section examining the hardness of the cookies they had left (I find the harder ones have more taste and taste a bit better than the softer ones. Bit over cooked I think. Maybe I just like burnt cookies

). At this point some guy came up to the cookies and suggested I try the milk chocolate ones. Something about them being soft or something. I didn't really hear, I was slightly stunned that a stranger was actually talking to me in a shop, for like the first time ever. I sort of smiled, looked at him for a moment then the cookies he suggested. Since I'm still not confident with my voice I didn't say anything so he continued shopping.
Anyway, wall of text. Just kind of surprised that I ended up going that far (ie: no jumper) and that it went so well. I really didn't have that planned when I left home