Long time reader, first time posting. Just like many others, my chest grew during puberty. Friends would tested me in a joking way when I was growing up. Friends would mention about my chest and female friends would recommend that i should try wearing a bra but I would just brush it off and not let it get to me.
Few years after high school, some friends and I was drinking and playing truth or dare. After awhile when it was my turn, one of my female friends dared me to wear her bra. So I caved in and tried her bra, also I already had a few drinks so I was whatever. I wore the bra for the rest of the night and ended up falling asleep still wearing her bra. The next day after getting up, I continued wearing the bra for a little while after fully waking up. After taking the bra off, I realized that being support is pretty comfortable and wouldn't mind looking into getting few of my own bras. Later that day, messaged my friend that I have her bra. She said to keep it cause I probably had stretch out the ban, so I said ok.
At that point, my mind was open about the bra thing. Eventually I wore my friend's bra here and there around the house to get the feel for it. Btw my friends bra was a 36c and the band was tight. I knew at some point, I'm gonna have to get a proper size. After research, I ordered a few different type online and it was a hit and mis most of the time. After awhile I finally worked up the courage to go get a fitting at macys. I called ahead and let them know what was going on and they was cool about it. When I got there, I approached the sales girl and told her that I called earlier. She said oh ok, and took me to the back to get measured and said not to worry, and thought that it was cool that she got to measure a guy for a bra. She came back with a few and explained what is what and tried all and settled with one. When I checked out, she gave me a few tips and said that after wearing all day, every day that I would get used to it after awhile. I ended up walking out with a 40b and at that point that's what size I looked for when I shop.
After getting properly sized and used to the bra, there was no turning back.
Anyway I'll be post more personal stories in the future in other threads.