This is probably going to be a very girlie sort of entry, so if you're a guy with issues, go do something else today...
I hate that they exist. I hate that I have to wear them. I hate that they never fit. I hate that I don't know HOW to make them fit.
My first experience getting fitted with a bra was not pleasant, and none of my experiences with bras to date have been pleasant.
I was thirteen by the time my mom bothered to take me in to get bras. I'd had boobs since I was 11... I don't think my mom was in denial about my growing up; I think she was just too oblivious. Didn't really matter, I guess. She took me into some department store, handed me over to a saleslady and wandered off to do some of her own shopping.
My cousin had already rather gleefully informed me a year earlier that I already had "cooper's droop", which is to say that my nipples point directly at the floor... The saleslady (and I use the term 'lady' with substantial amounts of irony) confirmed this, although she didn't use the phrase "cooper's droop." She said "Well... how odd. I've never seen anyone's breasts do that who wasn't 90 years old." She seemed to find it quite amusing.
I was fitted with a bra. A 34C. In middle school.
I got very, very accustomed to having a bruise in the center of my back from guys snapping my bra-strap.
I got very, very tired of guys putting their hand on the bus seat and scooting closer, so their hand would end up pressed up against the underside of my thigh, and then looking at me like "What the hell is your problem?" when I'd try to scoot away, or ask/tell them to stop.
I got used to the not-so-subtle gropes, "accidental" bumps, and general harassment. I remember Rex S. once leaning over the back of my seat and whispering that he didn't think it was too cold in the classroom, so I must be thinking about him. (It took me weeks to figure out what the hell he was talking about, actually...)
I got used to the jokes... "Guy is dead in the band room with bruises around his face, how did he die?" "Lynn shook her shoulders at him from across the room." "Oh, look, it's Lynn!" "How did you know?" "Her chest came into the room five minutes ago." Har de har har.
When I was fifteen or so, my parents were drinking with my uncle Chris and his wife, Virginia. (Chris isn't actually my uncle at all, he's my Aunt Aradice's first husband. After they broke it off, my grandparents didn't disown Chris. In fact, Chris named his son after my grandfather... I've always thought of them as Uncle Chris and Aunt Virginia... this fact did NOT, however, keep me from rather enthusiastically kissing my "cousin" Henry a few times...) It was late at night, and all the kids were supposed to be asleep.
"So, Howard -" My Uncle Chris says to my dad, "We all know you married Ardelle, but you dated Aradice first."
This was news to me... I snuck a bit closer to the opening of the stairs.
"Yep," said my dad. He sounded rather disgusted. He and my aunt had a long history of not getting along.
"Why?" Virginia exclaimed. "You hate her."
"Yeah, well," my dad said, "I was sixteen at the time, and she had these enormous tits, and all I could think about was getting my face in 'em."
My uncle bursts into laughter. My mom and Virginia sounded horrified in their exclamations of shock.
"Get yourself a stick," my uncle says. "Lynn's built just like her aunt."
Great.... just what I wanted to know.
By college, I was in a 40DD. I stopped buying bras in sizes and just got sports bras. They were more comfortable. I hated all that underwire stuff that seems to always end up stabbing me in the ribs, or digging into the breast. I never could figure out what size I was supposed to wear anyway. Nothing was comfortable, or looked good. I gave up caring about it. I had an enormous, pointless rack. It was just another thing on the list of why I wasn't particularly attractive except for all the wrong reasons.
But you know, I got used to it. I've had more than one lover comment on my boobs, favorably and otherwise.
My ex-husband told me that my boobs were entirely too big, and in his opinion, more than a handful was wasted. I won't repeat what I said back to him because it was entirely too rude.
Guys at the Anime Club once said that I could easily compete with the nurses from Ogenki Clinic. (Go ahead, Google it if you're feeling daring, but don't say I didn't warn ya.)
After I gave birth, I did discover that my weird, ugly, malformed breasts had one great redeeming feature. They were great for nursing. The angle was perfect. I didn't have to do any weird twisting. I could lay Darcy on my lap, and just pop it right into her mouth. Up until she started biting me around 6 months, nursing was the easiest thing about being a new mom.
My nursing bra (which I still have for some odd reason) is a 48G.
More recently, I've been wearing a 44DD, and sometimes a 44DDD.
More than one person has told me to do something about my bra. (Yes, all of them were women... I don't know if guys don't notice, or if they don't care, or if they're just too smart to open their mouths and comment.)
Most recently, Leslie said something about them. I knew the new bras I got back in March (42DD, for those of you keeping track) were getting loose. I was latching them on the third set of hooks.
Once again, I ventured forth to look for something new. The original plan was to go shopping with Leslie and she promised to help me with this bit of women's lore that I can't seem to manage on my own. That fell through because her husband decided that they should sit down and talk about their marital problems on the day we planned our shopping trip.
I don't begrudge anyone the time to yell at their husbands, and certainly not after the weekend she was put through, but it did mean I was back on my own for shopping. And that I now had to take Thomas and Darcy with me (since we didn't have much time to get my shopping done, and I needed to get a new vacuum - long story; my mechanical aptitude was tested and found wanting, and I ended up with parts for the wrong vacuum that couldn't be returned, and the parts I needed weren't made anymore, etc etc, so, $40 later, I have to buy a new freaking vacuum anyway!) I didn't feel very comfortable trying to track down a saleslady (not to mention that I'm still very wary of salespeople and their inability to keep from making me feel like I'm just not normal!) to do a fitting.
I did my own measurements again, and I'm sure that, once again, I did them wrong.
I came up with a 40C.
Unfortunately, with my baconish sunburn, my shoulders have been exceptionally tender recently, and I couldn't tell you if it fits right. My shoulder hurts too much to wear it for more than about an hour. And the material is scratchy. I can't tell if that's my skin being too overly sensitive right now, or if it's just a cheap (not in price, but in quality) bra.