5th Grade (10-11 years old):
I started to develop "breast buds" and began wearing undershirts every day after a horrifying conversation I had with my father.
Dad: Are you wearing anything under your shirt?
Dad: Maybe you should.
8th Grade Dance (14 years old):
For my 8th grade dance, I got a gorgeous black dress. It was a halter neck and had a low back, so my mom also got me a bra in a box that could be worn 5 million different ways along with being worn as a halter with a low back. We got the bra at the same time we got the dress, so my mom was able to make sure it "fit" along with being compatible with the dress. The night of the dance, my sister was helping me get dressed and we saw that the bra now gave me quad-boob. My sister and I both decided that this was unacceptable and I went bra-less.
Early to Mid 9th Grade (14-15 years old):
I went from wearing a 34B to wearing a 34DD over a couple of months. My breasts felt like they were on fire from the inside and I was not happy. When my mother took me shopping for new 34DD bras, she presented me with a beige-y, gold-y Olga bra and told me that when she was younger, she didn't have the option of prettier bras until the Olga brand came along.
My mother and I have have different definitions of "pretty bras."
The Rest of High School (14-18 years old):
Even though my breasts continued to grow, I wore mainly a 34DD all through high school. At some point, I discovered 32DDD/F bras and those fit a lot better, but were also a lot more difficult to find.
My first 32DDD/F.
The only time I was ever alerted to the fact that bands smaller than 32 even existed was by a sales woman at Dillard's. We went to get fitted and she told me that I was a 30DD. I was wearing the purple bra in the picture and because the top of cup was slightly wrinkled on my smaller breast, it proved that I needed to wear a 30DD. I didn't believe her because (1) she had no 30 bands to show me and didn't mention anywhere that even carried them, so I didn't think they even existed and (2) my other breast fit the cup. Looking back, I have no idea why she wanted to take me down 2 cup sizes because of a slightly wrinkled cup, but she was, unfortunately, the best fitter I had before I fit myself.
Prom (18 years old):
This isn't as much of a "bra" moment as it is an "alternative-to-bras" moment. I didn't wear a bra to my prom because of the dress, but I did use double-sided lingerie tape. I have the tape that comes in actual tape dispenser as opposed to pre-cut strips and it really worked. A lot of tape was used because I wanted to make sure I wouldn't pop out, but it lasted the entire night with no problems. I currently wear a 28H and I think I was around the same size in high school, so if you're around my size or smaller and can't find a bra that goes with whatever you're wearing--consider lingerie tape.
Picture taken as I dropped my camera.
Summer Between High School and College (18 years old):
I decided that I needed a bra that fit, no matter the price, and decided to go to Victoria's Secret. I had never shopped at Victoria's Secret before, but I assumed it was because of prices and not because they didn't have my size. (I mean, just look at the models. Of course they'll carry small band/large cup bras.) Looking around, I saw that the smallest band/largest cup size they carried was a 34DD. I was slightly disheartened, but I was certain that the bra would fit. (The models wouldn't lie to me.) I put the bra on and I was horrified. I was popping out from the top and the sides and the bottom. I immediately took the bra off, put back on my clothes and left the store in shame.
When I went home, I wrote an angry worded email about how, if they're going to brand themselves as THE lingerie store of America, they should at least carry more sizes (especially small band/large cup). The response I received said, more or less, that there was no business in small band/large cup bras, so they have no plans to carry any in the future, but I should still feel welcome to buy things that they do carry in my size. Needless to say, I have never gone into another Victoria's Secret with the intention of spending money. (I go for the free panty coupons.)
Freshman Year of College (18 years old):
I googled "32DDD bra" and came across this fitting guide. A lot of the links for retailers are broken, but first the worked was for Bravissimo. Since I wasn't sure what my actual size was (my mom measured me as a 28FF and I measured myself as a 28G), I was wary of paying $40-$50 for a bra that may not even fit properly. I looked online for cheaper prices and found BraStop.* My first order consisted of 2 clearance bras that I bought in a 28FF and 30F (the Flirtelle Divine and Panache Tango II Plunge. Neither fit, but I was able to determine that a 28GG would probably fit me better. I did end up buying another 2 of the Flirtelle bras in a 28GG because they were on clearance and those were my first properly fitting bras. I did go up a cup size after wearing them for a few months, so they no longer actually fit, but I still wear them (they haven't completely stretched out yet and I can deal with slight quad-boob).
*I don't mean to make this sound like an ad for BraStop, but I mainly buy from them because they have great prices and were really helpful when we thought my package was lost in the mail. Also, if BraStop isn't having a deal and you want to buy something, look at LoveBras because they have the same stuff along with free UK shipping and half-price international shipping most, if not all, the time.
What are your most memorable experiences?