My boobs made an appearance fairly young. I started my period at 11, so puberty hit me way before most of my peers. I can’t remember what it felt like back then. Not needing a bra, I mean.

I remember being so excited to wear the first little trainer bras my mum picked out for me. You know the ones, the basically-not-a-bra bra mums choose because they don’t want to admit you’re growing up yet. Padding or underwire or any racy colours were absolutely not allowed.

I was so eager to wear a bra as it signified being grown up already. It meant being a woman, and desirable. I wanted to make more of my boobs – sculpt them, push them out, show them off. I was so proud to have them, finally.

In my teens, I entered the stage of chicken fillets (bra inserts) and XL push-up bras, and bandeau body-con dresses just like celebs would wear. We watched and tried the pencil test from Angus, Thongs, and Perfect Snogging. We learned how to contour our cleavage with bronzer. We fed off the idea that big boobs were just better. A girl in my year, Abby, was a legend among the boys because her boobs had grown so big and so fast that she had stretch marks. I mean, we all had stretch marks, we just didn’t talk about it openly.

I quickly understood the power of boobs and bras to entice the boys in my year. They all wanted to know our bra sizes. Touching someone’s boobs during a make-out became hot gossip. One of my friends was given the nickname Big Tit Beth by the boys. It was unfair. The name stuck with her for too long.

I remember going shopping after getting my first-ever paycheck at 16. I bought a beautiful blue and white floral print lingerie set. That started years of sprees at La Senza, Ann Summers, and Boux Avenue trying to dress my girls up and show them off to their greatest advantage.

I’d always been happy with my boobs until I first noticed all the pretty dresses at Urban Outfitters floated over the top of slim mannequins with petite chests. Suddenly, everything was designed to skim over breasts rather than hug and accentuate them. Unless you looked like Kate Upton it felt like clothes weren’t meant to fit larger chests.

T-shirts had slogans you couldn’t read over the peaks and valleys of my boobs. Sizing up to fit my boobs meant clothes were baggy and shapeless elsewhere. Clothes that would have otherwise fit me strained and stretched over my chest. My boobs slowly crossed over from perfect to problem.

At this time, going braless was NOT an option. I remember one humiliating incident in particular detail. On an overnight school trip, the teachers let the students watch a movie together in pajamas. My matching pale yellow set was the perfect choice, but it was cold, and you could clearly see my nipples through the fabric. To quickly rectify the situation, I used the palm of my hand to warm up and try to flatten down the nipples that were soon to embarrass me in front of all the boys in school. I needn’t have bothered. Someone saw me doing that, and reported to all the boys that I was weirdly touching myself. I didn’t hear the end of that one for years.

As I approached college, I still loved choosing, buying, and wearing nice bras. But at some point, pink and red lace disappeared in favor of beige and white cotton. The sexy bras I bought in my teens were no longer practical. In my twenties, comfort became king. I yearned for the perfect seamless t-shirt bra or the bralette that would look cute peeking out of a strappy top.

Bras became an endless source of aggravation. They were too tight, digging into my back, my shoulders, and my rib cage. Or they were too loose, slipping off my shoulders every other minute. They showed through my clothes and ruined the smooth line of my back by making my flesh protrude. Taking my bra off at the end of the day became one of life’s small joys.

I’ve noticed in the last few years that start-ups and DTC companies have sprung up and started promising bras that fit perfectly like never before. They’re speaking to me, but I no longer want a bra that fits me perfectly. Actually, I don’t want to wear a bra at all. I want to feel the same freedom and comfort that I do in my home in my pajamas.

Now, summer is here in NYC. The heat has made me braver. The few times that I’ve gone braless in the last few months, it’s been magic. I didn’t feel self-conscious about my back fat sticking out or the band of my bra showing when I raised my arms. I felt sexier because when I moved, my breasts moved with me the way they were supposed to. They weren’t pinned in place. It felt natural.

On the flip side, going braless means getting a crick in my neck from glancing down constantly to see if my nipples are showing. I realize now that this is the only thing keeping me from going braless full-time. I’m clearly ashamed of my nipples. I have sadly bought into the societal belief that visible nipples are somehow inappropriate and people will think I’m weird if I go permanently braless. It’s not just me. One of the top Google searches is “how to go braless and not draw attention.”

More specifically, it’s the fear of my nipples being visible that holds me back. It’s too embarrassing, too revealing, too sexual for polite company. Female nipples are X-rated. They’re also a source of humor. See the Amy Poehler and Chihuahua scene in Meal Girls. It’s so ingrained in me that it’s wrong for nipples to be on show that I don’t know how to let it go.

I just spent a glorious Saturday in a black summer dress, free to move as I please. I don’t know if I’ll work my way up to regular braless-ness. Right now I have a tentative plan to try one day a week braless and go from there. At least that’s a start.

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