What was the first article of female clothing you bought for yourself? How did it go?

my experience seems a bit different from many of yours. i have lived a girl pretty much since i was 12 and that same year i spent allowance i saved up on a couple of really pretty floral sundresses, a pair of shorts and top, underwear and some cute sandals. i went in dressed a girl already with my big sister and didn't have any issues. this was 13 years ago (i'm 25) and i live in a fairly large, progressive city so maybe it would have been different elsewhere but there's a reason sephora boys are a thing so maybe times have changed?

Mine was a pair of nylon bikini panties in a pink color with a little lace on the front. I was 18.

I clearly remember. It was a bit more than a year ago. I did not have the courage to buy any sort of female clothes in person. Thank God my wife helps me now and we always pretend it is for her ( even if sometimes the difference in size is quite evident).
Anyway the first article was a set composed of a white padded bra and white g string. I had ordered everything online and collected at the shop. I was so nervous and excited at the same time😅. I was 25.

My first item was a pair of high heels, It was exciting and scary at the same time, The sales girl was very nice and made me feel comfortable, I will never forget, now the internet makes it fun and easy,I was 18

The first purchase of female clothing I made for myself was a pair of nylon stockings. It really wasn't a big deal as I had already been buying them for my mom and the SA's knew me by name. It did get interesting a year or so later when I needed longer stockings and started buying different sizes.


Karen

What was the first thing I bought? A grey skirt (C&A). How did it go? Badly, but things rapidly improved from there.

Patience,

It was a skirt. I was about fourteen or fifteen when my mom finally caught me in her clothes. She took me down to Goodwill and told me to try on some skirts to find one that fits. Once we found one she liked we went to the counter and she told me to buy it. She made me wear it on the way home and for the rest of the day. When she saw how relaxed and comfortable I was in the skirt she gave me a training bra, and panties to wear with it. Later then next day she wanted to have a talk with me and I told her how I felt about wearing girl clothes. We made a deal that only when we?re at home alone or I was alone I could dress however I liked.

@?}?-
Michelle

A lovely summery pair of black sandals with stacked heels. How else could I get out of the house? Everything else I appropriated from my mother's and sister's closet.

The first article of female clothing I purchased was pantyhose. The biggest stress was deciding on size. After what seemed a long period of confusion, I chose a pair and bought them. All in all, pretty dull.

It was over twenty-five years ago.
I was staying at a Marriott Hotel near Washington DC, and I went to a mall, that was walking distance from my hotel. In the mall there was a Victoria Secret shop, where I found a nice garter belt, with panties and stockings. I remember that my mouth went dry, as I asked a girl in the shop for help, finding something "for my girlfriend". I also remember that the girl that helped me at one point me gave me "the look", as if it was so obvious that it was for me and not for a girlfriend.

It has been so long ago, I can't honestly remember. I would guess it was Legg's Pantyhose in the plastic egg.
Would also say it had to be at the grocery store. Ya know run out to the grocery store for pantyhose.
But I would be so nervous thinking to myself did I buy enough 'other' items so it doesn't look like the pantyhose was all I really wanted "needed" ;-)

My first purchase was a little black dress. Because every girl has to have one. Right? I love it!

mine was very interesting ....i was almost 16 years old ,,walking down a street full of stores ...something caught my eyes ,,a lingerie store where he placed a label for sale to all items concerning bras , panties ,,,,Yet I was drawn into the store and remembered that I spent a long time deliberately folding and shoosing my favorite ones till I left the store with dozens of sexy panties and half dozen of bras ,,,,the problem was were to hide all these ? that was another story

Late bloomer here. I was mid forties and was in charge of a charity tag sale. I was alone the night before and on a whim picked out several items. Paid for them that night and took them home. A nightgown, a couple of dresses and some bandeau tops. I actually never did more than try them on.
In my sixties, I talked to my wife about wanting to dress for a special party. I had done research on sizes and had a pretty good guess for myself. I went to Alibaba (prices I could afford) and ordered a maroon dress with lace top, body briefer, thigh highs and 3" black heels. My wife suggested block heels rather than stiletto. Smart lady. I also ordered a matching dress for her. Being overseas, this company takes a long time to deliver. While waiting, my wife suggested we go to Walmart and buy me a bra. I was nervous when we started looking for the right size, but before we found it, I was feeling almost at ease. On the way out, she stopped at a panty display and picked out a maroon pair for me. We then went across the street to Goodwill and found one dress the right size. Not the best looking thing, but it is comfortable. The dress and all eventually arrived and fit pretty well, though a bit shorter than expected. Unfortunately, the party never came about before the Covid shut-in.

My first job was working in London a short walk from SoHo. After walking over a couple of times, I plucked up the courage to go into one of the shops there. After a quick browse I grabbed something in my favourite colour. A matching bra and panty. Took them to the counter to purchase and remember the SA saying "You know these are different sizes?". I just acknowledged, paid and hurried back into the anonymity of the street.

Bonus first time: That was nearly 20 years ago, further purchases had been made online.
More recently after laying dormant for a while I have returned to the CD world, and plucked up the courage to go buy something in person. I had gone to the shops early on a weekday. Went in my target shop, browsed around the lingerie section, grabbed another Bra and Panty set. Then spent ages looking for the hosiery section and then searching through for some stockings. They didn't have what I wanted so i gave up and paid for the set. Friendly GG SA didn't bat an eyelid.
I then crossed over to another store and looked through the hosiery section. Again no stockings but at least a pair of hold ups. I grabbed them and headed to the tills. Again nice, friendly GG not phased at all. Both purchases made in cash, both my heart pounding in my chest.

Tilly

The first item I bought was a pair of Keds tennis shoes. This was probably 20 years ago or so. I was at a Target, if I remember correctly, and bought them on impulse. It was close to Halloween. I had a story in place by the time I got through with the rest of my shopping and checked out. Nothing untoward happened, but I'm sure I was shaking like a leaf. :) I imagine most of the Americans on the board are familiar with Keds. They're a simple, canvas tennis shoe. They were very popular with the girls I knew in high school, so had always held a place of importance for my femme side.

Since then, I think a couple of pairs of hose at drugstores were the only in-person purchases. My only proper "shopping trip" was with a GG friend a few years ago. We went to a huge thrift store and I went a bit overboard. Luckily, she was nearly the same size as me, so it wasn't too obvious what was going on - or so I told myself.

Dana

Mail ordered pantyhose At age 51, I bought my first dress at a thrift store.

I think my first purchase was a pair of sun dresses when I was around 20. I remember being very nervous in the store but intentionally taking my time to make sure I got the ones that we just right.

Like many others I also had a terribly lame story in case I was confronted but as I know now to be generally the case, the clerk really didn't care.

I also remember rushing home, putting the blue one on immediately and spending all night in it.

I bought a pretty blue bikini when I was 18. I just had to have it. I used wet sand in balloons to make breasts. I wore it every chance I could. I felt great wearing it..