The first items I bought for myself would have been panties. But by that time, I had already bought several sets of underwear for my girlfriend as birthday and Christmas gifts, so I was totally confident at buying them.
The first items I bought for myself would have been panties. But by that time, I had already bought several sets of underwear for my girlfriend as birthday and Christmas gifts, so I was totally confident at buying them.
So long ago, I had some heels and a couple dresses as first purchases, but don't remember the order. Just bought them without knowing the size or trying them on.
Now I try them on before I buy, only took like 35 years.
Black garter belt, black stockings and black see thru full cut frilly panties.
It was a dress that I bought when my wife was visiting her family. We lived in NYC at the time. By the time she returned from her trip I purged the dress. By that time my wife and I had already shopped together for nightgowns and hosiery for me. At that time the nightgown and hosiery still fell within the "kinky" bedroom play. The first articles of clothing which I did buy and keep until they were either worn out or outgrown were a full slip and matching panty. The panty is long gone, but, I think the slip is still in storage.
Was in my late 20s, with my now-ex in an off-price store, a 2-pack of thongs so we had his and hers (or, as I'd now say, hers and hers). We enjoyed wearing them, and each other.
(Anyone remember C-Mart in Bel Air, MD?)
More recently, a 4-pack of cotton panties in an Ollie's . Turns out I'm a 7/large, not a 6/medium, so I had to re-buy. Expanded my collection thanks to Kmart going-out-of-business sales. No reaction from the store associates.
I was pretty late in buying my first item of woman's clothing due to me trying to suppress dressing. I bought a skirt and several pairs of tights. I was nervous knowing it was for me, but I had purchased several items for my wife no bother. I can't really remember the reaction of the sales assistant. But one that sticks in my mind is I bought some foundation and went to pay for it and the look was astonishment from the assistant.
My first purchase was a gorgeous under wear set in black consisting of garter belt, bra, knickers and full length silk slip
After I got tired of what I could find in my mother's closets, I walked right into the misses' department of a major local department store and bought an ankle length black skirt and a rather dressy top, white with some metallic silver embellishments. I was probably about 19. I didn't try them on, but I knew my measurements, and they both fit fairly well. The adrenaline was running so high that I have absolutely no recollection of the experience in the store - whether I looked nervous, how I approached the SA, whether they said anything, how I picked out those particular items, and so on. But I succeeded in making the purchase which was all that mattered.
I don't recall ever explicitly discarding that outfit, but I haven't seen it in years. It may still be lurking in the bottom of one of my Rubbermaid tubs somewhere (newer stuff is in the closets).
The floodgates were open after that experience, and many more clothes and shoes soon followed. There was a TJMaxx-like discount store in town that had a particularly fine selection of size 10 shoes, where I became a known regular customer. I still have several pairs that I bought there back in the late 1970s.
Another favorite haunt was Parklane Hosiery at the mall - remember them?
- Diane
I don't remember what I bought as a teenager at this point. But when I decided to fully crossdress, more than lingerie, I saw a satin blouse and skirt for sale at the dry cleaner (i.e., never retrieved or paid for) and I could tell would fit, I purchased it. I still have the outfit.
Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".
My first purchase included a few different items: a white, pleated skirt, a peach-colored top, a pink-tinged dress, and some undergarments.
OMG it has been so long ago i slept since then but i think a pair of nylons at the grocery store or a panty girdle at the Ben Franklin store that i rode my bike to at the age of about 10!
Matching panties and bra. I was around 30 years old. Guess better later than never.
My first purchase was a pair of 4 inch stilettos with an ankle strap.
A pair of French Coffee colored pantyhose at a local drugstore when I was 16(?). Next, about 10 to 12 years later a pair of black Just My Size tights. I still have them after more than 20 years. Don't wear them, they're way too big now. One memory I'll cherish is walking into a Savers and buying my first shirt and jeans, about 2-3 years ago. That was when I decided I wanted to wear women's clothes exclusively for good. It was a blue denim shirt and a pair of Gloria Vanderbilt jeans.
I'm a man. I like being a man. I also love wearing women's clothing. It's my way to show honor, respect and solidarity with them.
Vassarette satin panties. Bought them when I worked retail, but I bought them at the other store across town so no one I worked with would know. This was 1998.
I was in college, ands to that point had only "borrowed" my mother's things. I decided to get a pair of Hanes nylons, and my only option was to go to the local department store. I told the saleswoman I wanted a pair "as a gift", and she put them in a lovely gift box.
hello Patience,
It is amazing how some things stick in our memory - my first purchase was a pair of Pretty Polly 15 Den tights in powder blue from Debenhams.
luv J
First item was pantyhose but I bought them from a company by mail that sent me a coupon. I was single. After marrying, I purged everything including those hose. I thought I would not need to dress.... WRONG! First item I went in and purchased in person was my first pair of high heels. I had already gotten some pantyhose from my wife's collection and a slip and some panties she threw out. I kept those heels for 20+ years but eventually they wore out and were falling apart, even though I had only worn them inside my house and various hotel rooms.
Michellecd9999
Mine was a silky black blouse with a big luxurious ruffle around the neckline and down the front from a shop called Snob. The blouse had been on the display model in the window and I wanted it so badly. I went in (after walking up and down the street a couple of times to pluck up the courage) and asked the SA where the blouse in the window was. She directed me to the rail and advised that the bigger sizes were at the back, so I guess she knew it was for me. It was a bit of a blur going to the register to pay for it but once I was out of the store with my purchase I felt such a sense of achievement.
I think most of us remember our first purchase with fond memories.
Last edited by Crissy 107; 05-22-2020 at 10:06 PM.
Crissy
Yellow bikini bathing suit bottom with side ties. Bought it at the beach and wore it that day. No matching top, I hadn't yet developed the desire for full dressing. This was about eight years ago.
Pantyhose. I was in my early teens and was terrified when buying them. I bought them at the local supermarket. I felt like everyone is looking at me.
Opaque pantyhose.................
Escapism isn't necessarily bad, but is definitely unhealthy in the long term. While helpful in the short term, things will degrade over time. At some point, the escapee will have to face the issue. Things simply blowing over isn't really going to happen in many situations.
I was 18, maybe 1971. I ventured into Philadelphia, wandering through all the major department stores, Wanamakers, Strawbridge and Clothier, Gimbels, until I finally got up the nerve to ask for help. One very nice older woman helped me pick out a full slip, half slip, and some panties all in a pretty yellow, a present for my mother. It was obvious that another saleswoman disapproved, but the one waiting on me seemed to think it was sweet. I still don't know if she believed me or not.
mine was pantyhose from one of those mail order companies,
monthly supply, lol,
How did it go
I would say ok, here I am 45 years later, still dressing and loving it.
my sister's reply when I told her how I prefer to dress
"Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"