First purchase

At around thirteen years old, I spent 4 weeks' pocket money on a pair of black stockings. I remember my heart racing as I took them out of the pack and slid them over my feet and up my legs. Forty years later, I still get the same feeling when I get a new set of nylons and I love it.

It was close to 50 years ago for me.
Although I certainly don't remember. I bet it was pantyhose
I got them mail-order from one of those companies that would send them regularly.

Now I don't even think about it. If
I am in a store and see a nice dress, bra, whatever. I pick it up and buy it. Never a word from other customers or store personal. Not sure what they think. And honestly don't care.

For me it was a pair of black tights, many years ago.

Pantyhose, decades ago. I shudder to think how shabby and dirty they must have been before I threw them out, because every little item was like gold to me back then.

My first item was pantyhose I stole from my mom. Then panties I kept from a girlfriend.
First purchases had to be panties. I can?t be sure but remember wearing them under my sweatpants in my twenties. Before that only wore girlfriends or 1st wife?s clothing
My late 20s I shopped eBay a lot and bought heels, nightie more panties and pantyhose
First purchase in a store was nair, nail polish, and some lotions and creams.and Leggs in the shell. Don?t know if they make anymore. I got a look from the clerk and smiled and walked away swinging my hips. Had thing under sweats
eBay was hit and miss. Finally drove to a cd store in Orlando and was very happy. Tried on heels that were perfect. Bought makeup and a wig corset etc.
after I came out to my 2nd wife as a cross dresser after about 9 yrs of marriage and two beautiful children, she completely rejected me. Looked at me with disgust and wanted nothing to do with me. I moved out about 7 or 8 long months later and divorce was final within 90 days. I gave her everything she wanted and she never outed me. As far as I know anyway.
After that I purged Kerrie completely and forever.
But the last couple months she has been coming back and I have been a kinder person and not short with others. Feeling like I found someone I lost.
Sorry got carried away But thats some of the things I bought and have zero from the first 30 years of Dressing

At first I collected a few bits and pieces from the bin at home. I had a collected and secreted a long white slip, odd stockings, a bra and some french knickers.
Once I left home almost 30 years ago, I was very lucky to find a carrier bag of bits and pieces left by a previous tenant. Suspender belt, more stockings and a lovely long black nightgown.
All free.
My first actual purchase was from the ' lady of paris' catalogue which I applied for by post.
I was in a shared flat but I had my own mailbox.
Keeping the cost down I vary carefully chose a pair of plain black stockings, a simple black suspender belt, and a black camisole vest. This combination triggered free matching knickers.

It was such a treat when the simple brown envelope arrived a week or so later.
It was then a few days until I felt safe enough to try everything on in my room.

I still have the camisole. It's a sung fit now but I am lucky to still be able to get into it.
It was another year or so until I gathered the courage to buy anything in an actual shop...

It was 1981 or '82. I bought a pair of pantyhose from a vending machine in Bismarck, ND. A few years later I bought a bra and panty set at either Penney's or sears. I've purged a few times since then :heehee:

When i was in my early 20s, i wore girls jeans, and girls tank tops. I also wore girls sneakers. That was 30 something years ago. Unfortunately i don't still have these items.

Panties from Bali store, my SO was with me. After that it was cami sets from VS. My first dress, full slip, night gown and thigh highs from Dillard's. Beautiful blue floral dress unfortunately it's just a tad to small. I have to admit it gets easier to just act normal, I usually get a SA to help me out. Oh, and a beautiful necklace that my SO is dying to wear. LOL

[SIZE=1]- - - Updated - - -[/SIZE]

Next purchase will be a bra and forms!

First ever was a neat black mini (mid thigh) bodycon skirt from a catalogue. At the time I lived abroad in a large apartment block with a communal mail room. Someone had discarded the catalogue on the mailroom table and I collected it with my own mail for a browse. The model looked very good in the skirt. The skirt looked very good on the model. I liked the skirt and I liked that it wasn't just a pull-on tube but had a zip at the back. Having a zip closure was important and having it at the back particularly so. Even better, it was for the sort of money that I could afford to risk against choosing the wrong size. Best of all, when it arrived, it fit and hugged wonderfully. :) I wore it day after day after work. It gets less use these days, I've more clothes now to choose from, but it still fits. And still hugs wonderfully. :):)

The first thing I bought in person, still living abroad, was another, but somewhat shorter, possibly latex, pink mini that the salesgirl enthusiastically announced was 'hot'. That purchase involved a carefully-timed-for-a-quiet-moment, quick-in-and-out visit to a local boutique (!) whose window mannequins modelled the skirts. I had to have one although this one cost somewhat more money. Seeing it in the window day after day, desire wore me down and I planned my raid. For a while the skirt was fun but ultimately it went in one of my purges - probably for the best. It was a bit young for me even then.

I bought a purple satin playsuit and some cheap makeup. It felt nice but looked ridiculous so I threw it away.
After a while in the wilderness of trying things here and there, I did a M&S click and collect of make up, (lots) underwear, chicken fillets with a wig from amazon.
Stuck to borrowing dresses for a little while but I will never forget the first times in the wig. Truly life changing.

It was a blue and white floral skirt off the dollar rack at a thrift store.

This was four years ago or so. I still have it.

My first was a bra from an outlet store No its long gone I have made and still do make purchases from thrift stores

I was 16 and I purchased lingerie from Walmart lol

My first purchase was a green lace frock, a pink bra and a panty

My first purchase had to have been when I was about 12 or 13. I went to Carson, Peiry, Scott, and upscale department store. I went up to the counter where the hosiery was sold, that was in the day when hose came in a flat box. I bought two pair of jet black stockings and couldn't wait to get home and put them on. I know the lady that helped me knew they were for me but she was very helpful and didn't hesitate to sell them to me.

1985 I was 15 and roe my bike to Valley View mall and went into Victoria's Secret and bought a red satin garter belt and black nylons.

Eight or nine years ago I read a magazine article about women's jeans and how well they fit. On a whim, I went to the local thrift store and bought three pairs of skinny jeans.I took them home and much to my delight when I tried them on I was transported to a level of comfort and sensual satisfaction that I never knew existed.
Prior to that day I had never given much thought at all to matters of clothing. Things sure have changed though!

Not my 1st, but 1st purchase that made your stomach into knots.
Ie 1976 made a phone order from JC Penny which took like a week to come into the store, you had to walk up to the counter in the back of the building and the sales lady would pull order (bag) open it and check off the invoice to verify it was correct. Was my 2nd year in college, had a full body brief, foam forms, panties, bra. I sure back in 1976 they had good employee break room conversations.

I could wait to get to the dorm room to try my purchases on. 1st set of forms provided good shape over homemade forms. But no weight to the foam forms, but was 1976.

Pantyhose at the local pharmacy. I think I was maybe 12. Rode my bike there.

My first purchase was a knee length pink peignoir set purchased by my wife and me in 1972. We were shopping together for a nightgown for me. Yes, I still have it and still wear it. That's not the oldest nightgown I wear. When my wife was clearing out all the nightgowns that no longer fit her she offered to me the first nightgown I bought for her which was in 1971. It is a white midi length peignoir set by Avian. Midi on me; ankle length of my wife. In fact as I am banging away on this keyboard I am wearing the white peignoir and a white Vanity Fair panty.

Outer clothes, yes, because I just bought it a couple months ago. I was at Goodwill and saw the dress I'm wearing in my profile pic. Seven dollars and it still had the Old Navy tag on it for $24.99.

I first purchased underwear many years ago( knickers and tights) which I wore under my boy clothes. My first outerwear purchase was a denim mini skirt.

Way back in the 70s I was a young bachelor living by myself in a small apartment. I had a Macys credit card because I had to have appropriate clothing for work. The bills came in the mail and I wrote a check to pay the bill. Well, one day the bill came and one of the advertising inserts in the bill was for Pam nylon brief panties. They were $3.00 apiece and they would mail them to you. I was excited beyond belief. I splurged and ordered a whole $18.00 worth of panties in white and soft pastels and could not wait for the mail to come. About a week later, a couple of small arrived and I was in heaven. The panties are now long gone but the memory is still there.

Pantyhose at an out of town hotel gift shop.

Wore them once, and destroyed them in the dryer.

Oh well, live and learn.....