First purchase

[Mary Loo]

Official answer is while traveling for work one time in say my 40s? I was halfway across the country and alone and after a few drinks at the bar, went to a WalMart of KMart and bought 2 nightgowns. I think it was January or close to Valentine’s Day at the time and when the cashier sort of gave me a sideways look I answered with the tried and true known lie of they are for my wife for Valentine’s Day.

I went back to the hotel and tried them on excitedly. I still have them, but rarely put them on anymore.

Now, excepting those, only recently have I truly bought anything. From Amazon, 3 dresses, a pair of 3” heels and from WalMart 3 costume necklaces and a shapeware girdle with breast cups and straps that can come undone. In the past all I would do is use an old small belt of my wife’s to cinch in my gut.

That is ALL of my purchases so far.

[kirsten82]

Vanity Fair Briefs were my first purchase. For some reason I got the urge to try them and there was a VF Outlet near our house. So I took the plunge.

[P_Alexis]

My first purchase was some bras, thongs, & a pair of boy short panties. Well the thongs didn't work out so well since my boys wouldn't stay in place. I gave them to my wife.

[Melissa73]

My 1st purchase back early 90s....was at Target. I wandered for awhile around the womens clothing...scared that someone might see me. Finally i grabbed a black thong leotard and realized i needed tights. So scared, but i purchased them.

[ShirleyN]

Yes I do indeed. It was back in 1998. I bought a navy pleated a school skirt and then later on a black hobble skirt. The school skirt I still have unfortunately the other skirt I don't have anymore unfortunately and wish I still had it as it was so comfortable. Both of these were bought from a shop which sadly doesn't exist here in Ireland anymore.

[Jessica Secret]

I've always been obsessed with bridal sleepwear, and my first purchase was at 16, a gorgeous bridal satin nightgown/negligee from Dillard's and on the same day bought another one from Macy's. Heaven.

[Sandrajiggle]

My first purchase in an actual shop was an opportunity I spotted while working away.
There was a hardware store which I went to for bit's and pieces for work.
The shop also sold homeware and some clothing.
I had initially been attracted by a Doreen longline bra. On the same rack were foundation panties.
There were some skirts and blouses too.
I was far enough from home that I felt safe . It was a few days before I actually got the courage to stand by the rack. Check the size information on the packet.
Put the three items, bra panties and a plain dark grey pencil skirt in a crispy cheep fabric, into the basket.
I took everything to the till. I felt strange. Must have been obvious that the clothes were for me. I was even embarrassed that the undies were not sexy in any normal way.
It was also the sort of shop that lacks any care. There was no second glance.
I was handed a carrier bag.
It was going to be another 6 hours of work before I could open the bags and try everything on.


Nowerdays I am happy to shop in charity shop, supermarket and online.

[JulieC]

@Sandrajiggle; That's the bonus of shopping in a place away from home. There's just no consequence. So what if they think you're a crossdresser. It doesn't matter!

[Prazia]

A blue skirt and a pink top from a small local store. I was ecstatic, needless to say! Unfortunately, I had to dump them in the trash after a few months when living arrangements didn't have any privacy to store alternative wardrobe.

[BrendaPDX]

My first purchase was a dress from the Salvation Army. Sadly I don't have it any longer. It probably wouldn't fit me anyway.

[Elizabeth Marie]

My first purchase was a pair of pantyhose, ca. 1978. They went the way of all pantyhose, but it gave me the confidence to continue to buy anything I wanted.

[RachelWCat]

A pair of black faux leather gloves from Marks & Spencer in the UK. Probably early 80s in my early teens. I was terrified and thrilled at the same time. The gloves weren't that great quality and I ended up pinching a pair of my mums!

[Phose86]

My first purchase would be a pair of tan pantyhose from walgreens. I was 21. I was real nervous at the time but kept telling my self to do it. The cashier was a lady in her 40s. She rang me up thinking she was gonna say something but no, not a word at all about them or a look. I was so excited when i got in the car. I do still have the pair in its package. By the way im new here and glad i found this website.

[Karren H]

Mine was in 1969, I was 17. My girlfriend called my up and asked me to pick her up a pair of pantyhose on the way over to her house. We were going over to her grandmothers for a Christmas party. So I stopped by the local grocery store and bought 2 pair of L'eggs in suntan, one for her and one for me. L'eggs had just come out a few months earlier. The cashier gave me a strange look but even back then I could care less what people thought. Pretty sure her pair didn't make it through the night! We were rough on pantyhose!

Do I still have them? Who the hell has 53 year old pantyhose laying around? lol Since then I have grown to hate pantyhose. Thigh Highs or nothing!

[Crissy 107]

Oh Karren, you bad girl ruining that girls pantyhose, LOL

Phose, Nice story, welcome aboard! I recommend letting us know something about yourself in the introduction forum at the top.

[TAG]

Its been so long I don't remember but it never scared me to buy any female items.
I have never cared what others thought. Well maybe when I was a teenager.

[Katherine L.]

I was 24 years old and in the Army at a training course at Fort McClellan, AL. I ended up buying two Playtex bras at a mini post exchange one afternoon. I bought two because for some reason I thought I would give myself away by just buying one. I was terrified that someone would question what I was doing, but no one seemed notice, or if they did they didn?t say anything.