Panties, garter belt and thigh highs.Awesome feeling.
Panties, garter belt and thigh highs.Awesome feeling.
Gypsy skirts at a thrift store in Santa Cruz. Those things were so comfortable.
I was 24 years old and in the Army at training course at Fort McClellan, AL. I ended up buying two Playtex bras at a mini post exchange one afternoon. I bought two because 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.
Well the actual first was panties at K Mart! Outer clothing was a navy blouse with white flowers and a pair of navy slacks from Amazon! They are still in the closet! Panties were purged as they were too small! Hugs Lana Mae
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Everything was black, as I was just grabbing and trying to get out of there. I went to a JCPenney in San Diego (I was there on business and had a half day to kill). I grabbed a pair of hose on the first floor, took the escalator to the intimate apparel section to grabbed a bra, slip and panties. I paid for everything like I was holding toxic waste. Long story short, I put everything on and within an hour, it was in a dumpster. We all purge and it could not be a dumber thing to do. It's just clothes.
Today, I purchased panties in 100% male mode and could not have cared less. Evolution, baby!
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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.
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.
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.
A black, elastic waist full-length skirt, with a 2” wide white lace inset just above my knees, and similar lace at the hemline. Bought it at a ‘Fiesta’ grocery store in Texas, along with general groceries. I still own it, about ten years later, though I shortened it to knee length years ago, by detaching the part below the first row of lace.
The first item I bought was a pair of panyhose and before I put them on I bought some high heels on line when they arrived I put on the panty hose under my trousers and wore the heels this felt amazing and I started to learn how to walk in 4" heels, i bought more panyhose and started wearing to work under my trousers every day amazing.
I started to get the bug and before long i was buying all forms of female clothing and loving the chance to dress
It was a very pretty lace bra and pants set. With a matching slip. I pretended they were for my wife and it went just fine.
I was 25, I found an adult store that also had "stripper" clothes and shoes. I bought a pair of white heels, White stockings and a garter belt, and a very tight dress. I was in better shape in those days! I went in totally male and the girls there had no issues with it at all, they even helped me try things on. I melted.
Hi Patience,. It was probably a Bra or Nylon stockings some 65years ago, >Orchid ..o
o..
Having my ears triple pierced is AWESOME, ~~...
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I was around 12 or 13 and bought 3 pair of girls panties at Kmart. I was VERY nervous to the point my blushing gave me away to the cashier and she made a comment to not be so embarrassed I wasn't the first boy to buy panties for himself. I just froze and stammered they aren't for me and can still see how she gave me a knowing smile.
Can't remember what was first for sure. Either a some pantyhose and stockings for the good will store. Used to find new ones still in the package in older packaging. The women at the check out gave me a funny look. Or it could of been the a couple pairs panties I bought at Sears. The SA was super friendly and tell I was nervous. She then said at the end of the of my purchase. "Oh wait you get a punch card for panties and gave me a few punches and said just a couple more to get a free pair." I think I was sweating by then with the line of people behind me.
The first I bought was a red bodysuit and tights when I was about 14. I didn't exactly buy it myself, though. I had my GG cousins buy it giving the excuse that I was going to be in a high school beauty contest with other guys.
It was a long time ago but it must have been a dress. Our University had a rag week and many of the guys used to wear women's clothes for events so the local thrift shops were accustomed to male students buying dresses, so I was quite open about it being for me. The first thrift store I went to said they were a bit expensive for my situation and recommended another charity shop along the street. These ladies helped me pick out a dress which was in a slithery fabric, had a back zip and was very short They then selected a pair of slingback heels for me. I have no recollection of trying anything on, but these were my only shoes for years. They also offered to find a bra for me but I genuinely didn't want one. I think I got a pair of one-size tights in another store and I was set - I just wore male briefs. I think I went to a dance in the student union in the dress. I had very long hair but did not make any attempt to look like a woman. I had that dress for years.
my first purchase was a short green dress some stockings a bra and garter belt set and lacy white panties i had to put them in lay-awy my wife stood right next to me it was so cool but when i got all made up my wife freaked out told me she didnt want to see me like that ever again .its been 30 years since i bought that outfit i still own the pink bra and garter belt.we have been married for 39 years ,she still cant stand that part of me hell im 62 i need to be me .so i dress when i can .she sees my stuff she ignores it .i guess this is my life till i die but just once to be held as im dressed like she used to .but thats for another life i guess
I only brought the first items for myself only this year, I had spent 25years wearing what I could sneak into for any brief time.
So the first item was online and was some red high heels. In person it was knickers and Bra and went absolutely brilliantly with the sales girl being really nice and not awkward at all. This was just as I had been advised it would go on here and ended in a bit of shopping spree in a couple of other shops also with nightie and skirts being purchased.
Thank you, ladies.
It's funny that the thrift store where I bought my first skirt was two doors down to another thrift store.
The second thrift store had a larger dollar rack but that ended up translating into looking through more things to find the few that worked for me. I'm sure I picked up something there that day too. I just don't remember what, offhand.
What I do remember is once going through the rack as a staff person was adding some things. I was very comfortable shopping for fem clothes by then. The staff guy said the side I was on had more of the female clothing and I just looked at him and said in a deadpan way: "That's not an obstacle for me". It felt good to own it like that. I hadn't come out to any of my friends at the time.
When haters hate, I celebrate!
Wife sewed a skirt for me....that was the first thing I wore as well
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.
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.
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