First bra

Like many of you, the first bra that I put on was my mother?s. I don?t remember exactly how old I was but I?m guessing that I was maybe 13 or 14. I was already ?borrowing? my mothers and sisters panties out of the hamper and I knew that if I timed things right I had about 30 minutes to myself in the house every day. So, naturally, curiosity got the better of me and one day I hurriedly stripped down and put on the bra with the panties. Well, you can all guess what happened next. So, I did it over and over as often as I could and loved it each time. However I did not buy my first bra until I was out on my own after college living in an apartment. And not only did I buy a bra, but many and lots of other pretty lingerie as well.

Almost 60 now, certainly my own first bras were at college when first living alone at age 22.
My first love affair with a particular bra was with the Wonderbra # 2635?
They were white & black had a simple cup with lace trim but the four way stretch material made you feel wonderful , like a pretty catalogue girl, with a pair of their panties.
If the sizing was a bit off the elastic properties would easily handle it which was not my experience with other brands.
Tried Playtex but found them well made but little stretch, Warner's was not bad but things like Triumph, Vanity Fair etc , did not work for me, these other brands always seemed to have more nylon and less elastane.

I don't remember my first, but my favorite is a black satin long line bra.

My first bra is still my only bra (except for one of my wife's, that I fished out of the trash; I hate to waste anything). Bought a pocket bra and forms, a wig, an LBD, garter, and thigh highs, about 6 years ago at the Glamour Boutique. It was my first step into the CD world. I still have, and wear all of the items I bought that day.

BTW. The bra has 3 hooks. I have always loved the ones with more hooks, and a wider back strap. Probably because I associate them with bigger boobs, which I also love. Oh, that Sears catalogue when I was a boy.

Perhaps two stories. The first involved my mother's only black bra. Clothing way back then did not have any stretch. I foolishly tried the bra on only to snap one of the straps. I freaked out and put it back in her lingerie draw. I am sure she saw it. My mother and father probably suspected me, although they had no proof. They did their best to catch me wearing her clothing. They never caught me, but, I am sure they knew I was the culprit.

The second was about my first bra which was a Vanity Fair vivid red bra. I bought it at Christmas time which seemed a great time to fly under the radar when buying it. At the time my wardrobe on lingerie fit in a large gift box in the bottom draw of my armoire. My wife knew I liked the feel of nylon and together we had incorporated nylon nightgowns into the bedroom scene. She did not know about the bra until our three year old daughter yanked open the draw and then the lid to the box. She pulled out the bra which my wife found. That led to "The Talk" and ultimately to a life of "Don't Ask, Don't Tell." Her memorable comment was "Why would a man wear a bra when he had nothing to pack into it?"

Like so many of you the first bra I ever tried on was my mother's Playtex cotton bra that I liberated from the dirty clothes bin and stuffed with toilet paper to fill the cups.

My first that I tried on was my sister's. Front close, beige. It fit perfectly, I was probably around 12 or so, my sister would have been 15. I think the first that I bought was a blue underwire t-shirt bra and a nice lacy bralette.

Like everyone else I was always borrowing bras from mom or if I went to my friends house I would look for their moms or older sisters.
But I count my first bra as the one I bought myself in the store 🙂
It was from JC Penny, a light pink bra/panty combo that had padded cups and the trim had pretty lace the whole way around it?I guessed and bought a 36b, it fit so good and I will never forget how good it felt wearing it 😍

I rather tend to remember the milestones in my bra journey.

Obviously, I tried on my mom's bras, but these were frumpy & didn't fit.

I remember much more vividly my first real bra - second hand from eBay - which actually fitted. I finally realised that the conventional bra wisdom, that you buy a bra with a band size 4" larger than your under-bust size, was a relic of cotton bras with no elasticity in the band or straps. I logged into the HerrRoom site to get better fitting advice.

My first milestone was that having ordered a 38 A cup, being the smallest, I actually could fill a B cup!

I am now up to a full C+, and it was another milestone to realise that I could not only fill a bra cup, but I am actually a lot more comfortable wearing a bra!

The underwired balconette with a 3 hook deep band has become my favourite for shape and uplift, but there have been some failures too.

Namely, strapless/cross-strapped bras just don't work. The cup shapes are all wrong, and the straps cut across the shoulders when going crossed. The same goes for halter necked bras.

In contrast, I have just got into bustiers, and I think these could become a positive milestone!

The first bra I tried was my mother's. All the elasticity was in the back band; I liked the feeling of it moving against my skin as I breathed.

I think sports bras are popular everywhere, no matter whether you are in America or Asia. I love bras with orthopedic effect – I use them for my everyday runs https://thefluencewoman.com/best-pos...orrector-bras/. I always wear bras at work, but do not wear them at home. The only rule I have is to buy good quality lingerie. I avoid cheap goods.

Having the beasts is what I like and makes me feel more feminine, not wearing a bra.

Well, my first bra wasn?t even an underwired one, since I was just starting to experiment with crossdressing. I didn't really intend to get any sort of cleavage, just an improvement in my ?female? silhouette, since I was wearing barely any shapewear, and I have a very masculine figure (being about 180cm tall and weighing around 100kg). As the color didn't really matter for that, I went for a simple beige bra, with elastics instead of casps. Then I paired it with a pair of adhesive push ups, in hopes that it would hold everything in place?

But yeah, things didn't go very well. I wasn?t able to build up enough volume on my chest, so it looked really off and awkward. I did some research only, looked up some brands of breast forms and planned my budget to acquire them, but I wanted to come up with an alternative to keep crossdressing until I could afford some nice forms. Well, this was the first time, but since it was a total failure, I don't count it. So, let me tell you about the first time I really felt comfortable and feminine while wearing a bra.

It was with a properly underwired bra my girlfriend helped me to buy, which I tested fitted with a few different ?fillings?. I first tested the classic socks, but yeah, they didn?t suit my body type very well. Then, i cutted out the cups from that first bra I've mentioned, and combined it with pushups, holding everything PROPERLY in place. I felt awesome, and my girl even helped me with a ?Cleavage? using some makeup tricks and such. This bra was also beige, but underwired and with actual clasps to better fit me. It was very comfortable, and the push ups/bra cups combo was a nice trick to create some volume.

Nowadays, i?ve managed to get a silicone breast form vest from roanyer. It's a C cup, but it increased my chest so much I had to buy a new bra. It?s a black one this time, with no wires and loose cups, so i can comfortably wear it with or without my forms on.

My first bra was my mom's. but of course it didn't fit properly, but I make due by stuffing it with tissue paper. The illusion was fantastic. By adding a panty girdle and nylons, I was able to achieve a really feminine form.

This thread is invoking such happy memories. I can't actually recall my first time wearing a bra. But I still have the first one I ever bought. I never wear it these days, it is well past best, but I doubt I will ever bin it either.

Can’t believe I’m sharing this. First one was my wife’s that she had me try…she’s bustier, but I’m not a huge chest, so I was able to get it around…had never really worn one or been interested. Wife purchased the next two (white and a black one) and sized them correctly. She put in some water balloons and she said she “strangely liked it”…I said zilch as to not draw attention.

13 when i first tried on my moms bra
Got so ?hooked? into wearing one that I eventually got caught and smacked for it. Coming from a Muslim background it?s not something parents want to see. Eventually moved out at 18 and got better at hiding it and now years later still ?hooked?

My mother was what I called a soft pack rat and saved while not everything, quite a lot and stored old bras and panties in my room thinking they'll be safely stored. Well, she didn't realize she had a crossdressing son and about the age of 10, I got curious and tried one on along with a pair of panties. Well, I was hooked from that time on. I will never forget it.

I still have it, I was able to "Man-Up" and buy it at Walmart's . It's a nice Black Push-Up and I still like it.
Thanks, SuziH

Like others here, the first bra I tried on was my mother's. I didn't have any sisters, so I was pleased when I grew tall enough to fit into some of her clothes. She was short. I bought my first one when I was in my late teens, after trying on one of my girlfriend's bras, which felt amazing-- it totally relaxed me. When my mom passed away a few years ago, I inherited her things and discovered we both wore the same size bra, a 36C.

First bra I ever wore was my younger sisters. I was about 14 at the time, she was 13 and just starting to grow breasts. I have no idea what size it was but it fit.. and felt so nice. I would borrow her panties and bras on occasion from then on. I remember one night she had a girl friend sleep over. I snuck into her room and "borrowed" her friend panty and bra. Just felt so right tho it was wrong to do so.

My sisters are both younger than me and I could never fit into theirs, so, like many of us, the first bra I ever wore was my mothers. When I got to 12-13 years of age we were about the same size and they fitted me perfectly. The first bra I ever owned my wife bought for me. It was a plain skin toned Playtex Cross Your Heart bra. Not fancy, but it was mine. 40 years later I now own over a dozen bras. Many different styles and some with a matching panty. I love my bras and pantys. Quintessential women's wear, They help me feel so feminine.

I don't exactly remember where the/my first bra came from but I do remember keeping it in a wooden box along with rolled up tights.

I was a little bit later than some when trying my first bra. A few months after my wife and I got married. I was curious on what a bra feels like on me. So, when she was not home one afternoon. I put one of her bras on and from there I fell in love with them. However, my very first bra that I could wear around my wife came about 6 years later when I came out to my wife and told her that I like wearing women's clothing. She went out and bought me my first bra. She is a great wife and I am very grateful for her love and support with my crossdressing.

My first bra wearing experience was my sister's training bra. It was blue and had a picture of girl on it. She also had panties that matched the bra. From there I wore her other bras many times. I even hide one or two around the house for my use. I spent many nights babysitting neighbor kids and took advantage of trying on the mom's bras and even a dress or two. I know now that shouldn't have done that but hey what's a guy to do when you are 12 or 13.

Tracy