Your first in store purchase.

[StacyG]

This site keeps taking me back down memory lane. Today with the internet we can buy stuff online easy enough. One of my favorite dressing memories was back in 1985 when i was 15. I had worn all my mother's and sister's panties and lingerie and nighties. They were pretty conservative and I wanted a gartebelt and silk stockings badly. I got on my bike and rode the 4 miles to the mall and walked into Victoria's Secret trembling and terrified from head to toe. I only dreamed about going in there and now here I was. A lady asked if she could help and I said I was looking for garterbelts. She showed me and I grabbed the first one I saw, red and satin. She got me some stockings that had to be silk or nylons. There was no elastic in them like panty hose. She must have known they were for me because we didn't discus size or anything and they fit perfectly.
I remember nervously paying and then having to walk through the mall with a VS bag for everyone to see. Then riding my bike back home fast and furious to try them on and fall in love with them.
After that, it got a little easier. I could go to the lingerie department in sears or JC Penny's and take my time. I could go to TJ Max and cRoss Dress for Less and dig through the bins of satin bikini panties like a kid in a candy store. $3 each or 2 for $5.
Thanks to everyone for making me feel welcome and at home amongst friends.

[Patience]

You're welcome. Hope you enjoy the ride.

I only accepted and started acting on this part of me three years ago.

My first purchase was a blue and white skirt off a thrift store's dollar rack. It was the easiest thing to eyeball for size at that stage. It literally cost $1.00. I still have it.

[CeCe]

Back in the 1980s, I was in a discount clothing store and I noticed a table full of beautiful bustiers at a very cheap price. I had never thought about buying women's clothing before but this was too sexy to resist. They were all for tiny ladies so I found the biggest one, bought it, took it home, squeezed into it and enjoyed wearing it.. Shortly thereafter I saw a store that was going out of business that posted a sign saying garter belts were on sale for $15. Now I had two items. I brought home black stockings from the grocery store, picked up white panties, a skirt and a blouse. It all came together because of that fateful day in the discount clothing store.

[HelpMe,Rhonda]

I can't remember if it was dress or heels or both. Sometime in the 80s in a discount place near Times Square. Had no clue what size dress to get so ended up with one way too big, too afraid to even hold it up against my body.

[jjjjohanne]

After I became brave enough to say, "I am shopping for a skirt for me," I was shopping in a small "mom and pop" clothing store. The sales person was being very helpful. I asked her if she gets a lot of guys buying for themselves. She said, "No." I was her first. She and the other employee told me about another customer who came in on the same day as me. He had a list of items to buy for his wife. His list had sizes and everything. They said they had fun helping him and told him to come back anytime with a list. I asked if the sizes were large. They said yes. I told them that having a "list for my wife" was a common trick used by crossdressers to buy for themselves. I know this is a mere single anecdotal piece of evidence... But, in this case, the sales people had no idea. They completely bought the lie.
(I ended up buying a colorful maxi skirt made out of liquid knit fabric -- so silky -- and a short sleeved top. I wore it out of the store with some shoes I had in the car. They welcomed me to come back.)

[Debbie Denier]

4 pairs of tights/ pantyhose. Enjoyed them so much went back for more . On the 2nd occasion the shop assistant an older lady at the time in her 60s started to discuss different deniers, sizes etc. Looking back I am sure she was trying to embarrass me . I felt she knew they were for me.I just looked listened and took the information in . It didn?t put me off.

[kellyanne]

That's almost 40 years ago but my first female clothing purchases were from a " Love Boutique" and was a black garter belt with panties and stockings.
After that it was the thrift store a few times and then department stores. In those being transgendered was not as well received when buying women's under garments etc and I had a few negative experiences with clerks.
After those times, I started carrying a paper list as a " visual prop" and would present myself with the list and say:
Excuse me please, " but I am here to pick up these items " and show the list with the body language of the " helpful hubby" in a suit & tie since my work required being out and about around the area.
Lookin back - 95 % + were professional and courteous but a few were meanies. Can't say how many knew, had many 50s - 60s really polite ladies , seemed to really want to make you feel comfortable, like a mom, who would fold with care and I think these " mothers" probably knew.


If I had no direct help, I tried to round up my list items and time my counter approach to be solo but there were those times
in the big department stores when a crowd suddenly forms and one is the only male with an arm of panties and bras in the line of 12 - those minutes seemed an eternity

[NancySue]

Like Debbie. Pantyhose. The SA was very helpful showing me different colors and brands. At first, I was a little timid, but she made me feel like it was no big deal. I, of course, bought several pairs. Sometime later, I returned. She recognized me immediately. She suggested thigh high hose. Yes, I bought several pairs, different brands, colors. Looking back, I?m sure she knew who they were for. On my third visit, I asked her what her favorites were. She didn?t hesitate to show me the pantyhose she was wearing, which were Hanes Silk Reflections, Barely There. To this day, HSR are all I wear, which is daily. I prefer thigh highs. At my next visit, I found she was transferred to the makeup department. That?s a whole new story.

[Lana Mae]

It is a swirl as to what was first but...I believe it was my trip to a MAC counter in the mall inside a Macys! I got my transformation and was told to get a color match at a make up counter! Scared and happy at the same time! Got color matched, made up, and the proper make up! Now it is old hat! Hugs Lana Mae

[Stephanie47]

Like most, the first garments I wore belonged to my mother. I did not have a sister until I was twelve years old. I started wearing my mother's full slips and nylon night gowns and went further into her drawers; girdles, bra, hosiery and panties. After I outgrew her clothing there was a long lull. It wasn't until I was married and thought I had been "cured" that I got back into women's wear. I had bought my wife a white peignoir nightgown by Avian after we were married. It was a size medium and it swam on her petite body. I had no idea about sizes. Anyway, one night I tried it on and she walked in on me wearing it in the kitchen. She asked "why?" I told her the truth which was I liked the feel of the nylon on my body.

We were crazy young adults. We went shopping a lot of negligees for her in midtown Manhattan; Macy's, Gimbel's, Saks, Bloomingdale's, and others. Together we bought for myself a knee length pink peignoir which I still have and sleep in regularly. We also bought for me a black floor length gown which has long since gone to the donation pile as the fabric did not have any stretch and the style was somewhat form fitting. That white negligee I bought her? About two to three years ago she was clearing out the back of her side of the walk-in closet. Unfortunately, there were scores of nightgowns that no longer fit her. Sigh! So sad! Anyway, she tossed them all on the bed and told me, if there was anything in the pile I wanted, take it. I was dumbfounded. In a deep DADT marriage since 1983, she told me to take anything I wanted. I think she knew the only one I would take was that white peignoir. I took it and also wear it regularly.

The first garment I bought by myself was a dress while my wife was across country visiting her family. Probably 1973. I wore it while she was away and promptly trashed it before she returned home.

[Karren H]

1969 or 70. I was 17ish. My longtime girlfriend asked me to pick her up a pair of pantyhose on the way over She said it was my fault all of here?s had runs in them, aka crazy sex! Lol. We we?re going to her grandparents for a holiday party. So I stopped at the grocery store and bought two pair, one for her and one for me! Think they were Leggs in suntan. Next purchase was a few years later, eye shadow and lipstick. Always got stares but never cared even back then!

[jjjjohanne]

I was around 22 years old. I still lived with my parents. I was driving home from work and got the idea to buy some pantyhose for myself in a grocery store. I went to a store and got a shopping cart. I traversed that whole store making sure no one was there that I knew. I got things that I would consume, like peanut butter. I saw my 10th grade English teacher in the store. I shopped for another hour, perhaps, until she was gone. I got the pair of pantyhose and carefully selected a cashier that I felt comfortable with. I did it! It probably only cost me $25. HA!

While I was typing this, I remembered another time before that! My high school prom date asked me to buy some white Leggs Sheer Energy pantyhose in size A at the store on my way to pick her up. I decided to go earlier, because I didn't want to be in the store in a tuxedo looking at the pantyhose rack. My plan was to walk past the display, quickly grab the package and keep walking so that no one would notice. The display was on the end of the rack in a grocery store. It was about 2 meters wide and 2 meters tall. There were about 100 options. I passed the rack several times. Eventually, I stopped and searched. By the end, I sat on the floor in front of that rack and looked until I finally found them. Since they weren't for me, selecting them and paying for them must not have been too stressful. I don't remember worrying about it. But, knowing me, I worried about it. I always worry!

[LIKETODRESS2]

The first time i ever bought was panties from Shopko .

[Kitty Sue]

I was 17 when I first bought lingerie for myself. I went to a lingerie store and like, Stacey, I bought a garter belt and stockings. They were black. Of course I told the sale's assistant they were for my, non-existent, girlfriend. Since that time I have gone to loads of different women's stores including VS and frequently tell them I am buying for me. Adds to the fun of it IMO.

[sara66]

I was 28, I went to Denver (8 hours away) to a hanes bali store, I bought a lace body briefer in black and a pair of pantyhose. Scared to death i could not wait to get to the motel and put it on. From then on I went to Colorado every year to go shopping. It took several years before i could admit to the SA's that it was for me. I never had a bad experiance. i sure most of them knew.
Sara

[Bianca Fay]

My very first purchase was a pair of pantyhose that I placed in a shopping cart full of groceries. It was the only item that literally required a PA price check announcement from the pretty cashier.
Most of us stress about buying women's clothing because we think the sales clerks assume we're buying the items for ourselves. In my opinion, we're right. They seem to know!

[gwencd158]

Oh god … price check on lane 3! Been there and almost died. My first purchase was leg warmers and a leotard that did not fit back in 1983. After that, I sold my college text books back to campus for play money and purchased my first wigs from a thrift store - I washed them of course. Borrowed my live-in girlfriend soon to be my wife’s clothes which did not fit. My first clothing purchases that fit were thrift stores, and the first time shoes that fit were Payless! Talk about woman’s intuition, I remember watching tv one night with my soon to be wife..she pulled me into the bathroom and out of nowhere started putting full makeup on me, then led me to the bedroom and told me to put on her leg warmers and a leotard she found in a thrift store that was obviously too big for her. It was the 80s..leg warmers and leotards were big then. We had “fun”. That was the first and last time with full makeup. Lipstick lasted for many years with some allowance for nighties and such, then disappeared completely.

[Cheryl T]

My first was pantyhose.
Sweating, shaking and looking like a thief about to get nabbed as I quickly read the packages to determine the correct size and then searched for it ... In BLACK of course...

[JustJennifer]

Seems to be a pretty common experience... buying pantyhose at the grocery store. I recall going up and down every aisle in the store with my shopping cart, picking up lots of other random items to provide cover, until I could work up the courage to step into the forbidden zone and grab the first thing that looked right. I didn't dare make eye contact with the cashier.

I still get antsy, but I've (mostly) given up the laughably transparent pretense that I'm in a store for something else and just somehow wandered over to the women's section.

[Jessica Strong]

Bought shoes and two dresses - asked for a gift box but got a knowing look from the store assistant.

Was scary and exciting all at once.

More success online now

But was still a rush

[NancyJ]

I bought a white garter belt and nude stockings at what used to be called a five and dime store at a mall when I was probably14. I had gone into the store and looked at them multiple times before buying them. I remember the garter belt was in a cardboard box with a picture on the front. The boxes were hanging on wire racks next to the packages of stockings. I did not understand why I felt so compelled. It made no sense to me to be so ashamed of something that made me fell so wonderful. Wearing that garter belt and stockings felt RIGHT!

[Blonde617]

In my 30’s, week before Halloween, walked into a Lane Bryant to buy some panty hose, as suggested by my GF.

The woman at the counter asked, “Are these for you?”

I replied “No,” and she said, “Yeah, sure.” Blushed bright red.

[Daryl]

Been so long ago, but it was panties or pantyhose.

[freeindress]

One piece swimsuits in large sports stores, to swim in public pools in Paris, then sports bra and matching shorts to run in parks.

[Taylor Dame]

My first experience was purchasing a blue garter belt at Fredericks of Hollywood store - remember them? I'm not divulging how many years ago.