How did you come by your first bra?

Hi Sarasue, as my crossdressing surfaced when i was 22  it was my wife and i that shopped  together and still do to date 44years on . We have her mum with us full time,but she has known from the beginning also . How fortunate am i ,i love them both dearly. Pyxx.

I have one on now 🙂 , I'm sort of new at dressing. I was buying panties on line and just had the thought to try a bra and then it was like lets try a skirt etc. I do love the padded bra look an feel for sure.....

Lisa.....:)

I was buying lingerie for Christmas for my wife. Always fascinated by panties and bras.....so I picked up some for myself (my favorite Santa gift to myself)....at age 27! Now I shop for myself at any store and on line. Wife and I separated long ago and I have been Veronica for years. Love looking on internet for clothing and especially love my ball gowns.

Dame Veronica

Never had purchased one of my own until a few months ago. “Mine” was destined for a donation. During a violent rainstorm , I was running erands and was a small retail center that was recently occupied by a Ross store. Timing is sometimes everything. Nobody out so decided to try shopping there for  a few minutes. Nerve wracking, first time  shopping in the women’s area by myself. I found my bra and some panties there, correct sizes in about thirty min. Check out was so pleasant In spite of what I anticipated. Grateful for the assistants there. Perfect fits. Lovely feeling, just lovely. 👗

I measured my chest, did a little online research, then headed to one of the superstores. I'm not a big fan of large breasted women so decided that I would probably be comfortable with a C cup. I bought 2 that day with some pads and have never looked back...though I do look down and in the mirror quite often lol

I used to travel a lot for work and it was either  long line bra out of a department store up in Sydney or a lingerie shop in Adelaide. I'm in Melbourne...

But its 40 years ago if its a day and I cant remember which one was first. But I still have the "Adelaide" bra. Its stretched, wrong size now and looks a little ragged.

But its a nice souvenir of "days gone by".

The first bra I remember was purchased at Sears. I had  wrote my size on a list and found the SA. She found the   Longline bra I wanted. I was so very happy 😊. I still love wearing bras even though I no longer have a longline Bra.

Hello Sarasue,        I was in my early twentys, & had just started to go out & by my own clothes. In those days we had a store called BHS, so I was in the girls dept & bought a bra & knicker set [ white with pink hearts on], still have the bra. Have had many different bras sence, but still like to kept my first bra.

love,  Helenmarie

I never had the opportunity to wear one when I first started dressing. In middle school, my older sister was smaller than me by quite a lot. I viscerally hated my step-mother (now she's tolerable, but only just), and I didn't want to be near anything associated with her at all. Later, my girlfriend (now wife) was so petite and tiny, hers wouldn't even come close to fitting - I would have positively destroyed them had I attempted to wear one.

After years of just panties and fantasy, I bit the bullet and went to a Sears WAY far away from my house, and after much wandering, sweating, and freaking out, I bought a matching pink floral print-on-white satin panty and bra set. I raced back home, still shaking and sweating, but this time with the need to get them on my body as fast as possible. I wore that set until they were stretched and worn out, taking it out of hiding every chance I could get, like a junkie desperate for their next fix. By the time they no longer fit properly due to wear, I finally tossed the set out in what I would later learn was purging - I felt like the need to wear those two pieces of clothing was so strong that it was actually affecting my daily life, and that I needed to quit wearing them, full stop. I fought the urge for about six months before buying another set; the beginnings of a cycle that would fluctuate between a few weeks and a few months, until a few years ago, when I just sort of stopped feeling that familiar, overpowering urge. Now it feels different; I want to dress, as opposed to needing to dress. I am more comfortable in being who I am. I don't have anything feminine at all at the moment, but I will be definitely hitting up the shops in the near future, and I'll be feeling good about it when I do!

Hi Gillian.

It seams you discovered the power that bras have or they unlock something deep with in us, I have not discovered what it is but its A powerful force. And as we get older it seams to get stronger. When we add A bra to panties and slips as well as A dress or A soft silky blouse and skirt it makes us feel more complete and at ease. I sometimes feel very sorry for those who have never discovered the joy of crossdressing.

Sarasue

A bra does seem to unlock a mystical feminine power for me that only the sexiest strappy stilettos can also unlock. Getting dressed up (when there isn't enough private time) with no bra just doesn't feel the same. Yet, wearing just a bra under my male clothes lets me wield its superpowers.

The first bra I tried on was my ... mom's ... too embarrassing to say now, all these years later. It took me years to finally have enough courage to buy my first bra, and it wasn't spectacular.

The oldest bra in my lingerie drawer belongs to my wife...it's a bra of hers I used to borrow, one I always had an affection for, and somehow got to her to let me keep when it no longer fit her. It's still one of my favorite bras. Ironically, years later, I gave her one of my sexy bras I had bought when she needed one with a better fit for an outfit.

When I returned to crossdressing in the spring of last year, I didn’t get any bras right away.  My wife had recently asked me to get her some bralettes online from Torrid and loved them.  She can’t dress herself, so she felt they would be easier for her aide to just slip over her head and around her bust.   They looked comfortable and really sexy on her, so I ordered a couple of my own.

OMG, I was almost instantly hooked for life.  No pun intended because bralettes don’t have hooks, at least not the ones I have.  They really do have superpowers.  It’s like this magical embrace of femininity that makes me feel content and at complete peace with my sissy side.  Now I have about a dozen bralettes, in different colors with beautiful lace and floral patterns.  I order them slightly small so that they hold my breast forms nicely in place.

Many nights I’ve gone to bed in just a bralette, bikini undies and pantyhose.  In the warmer weather months, I would lounge around the house like that, with a nice glass of wine.  It doesn’t get any better.  It’s my special comfort zone.  <3

I came by my first bra by mistake. It was more than 40 yrs ago. Back then I bought all my panties and nighties at Kmart. It was never at the store closest to my town but instead one 20 miles away for fear of running into someone I knew . One day I was in the store closest , not for lingerie but maybe the complete opposite , a case of motor oil! I loaded the case into my cart and headed to the checkout, but not before at least walking by the lingerie department . As I passed I noticed a discount rack and in particular a long pink nightgown. I possessed half a dozen short nighties but nothing long and it was on my wish list. I quickly looked at the tag , it was my size and was marked down to like 5 dollars. I decided to go for it and headed to the checkout with motor oil and a pink nightie . I rushed home to try it on . When I removed it from the hanger a pair of panties fell to floor and still attached was a little bralette. Turns out it wasn’t really a nightgown but a matching pink bra and panty set with a long matching coverup all with lovely white lace trim. To my surprise both the bra and panty fit, the whole outfit was so cute and girly . Of course I no longer possess it , probably lost in my first major purge before I married , but it remains one of my favorite purchases ever

My first bra and panties came to me by stroke of luck at the laundromat. I was single and  28 spending my usual Friday night at the laundromat.  It was almost closing time and I found a mesh bag in a dryer containing the panties and bra treasure!  Nobody else here, so I stashed it with my stuff and left. When I got home I found 3 matching pairs in black, red and purple.  The panties fit was a little tight, but I liked the feel of it that way and the bra was a little large but I "filled it".  It was a great addition to my clothes. I only had a dress and skirt from a rummage sale that was not perfect in fit. On my off days, I loved to just wear the panties and bra on really hot days and do housework or reading.