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.

[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.

[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.

[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

[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! :)

[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

[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.

[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.

[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. :)

[JustJennifer]

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

I made a huge mail order purchase from Fredericks of Hollywood when I got my first apartment. Except for the stockings, none of it fit, but I was too embarrassed to try to send it back. (The stockings of course got runs immediately because of my toenails.) Held on to that stuff for 20 years before finally tossing it in the trash.

[WillowHanna]

First in store purchase was 5 panties at Walmart. With the help of my wife we bought 5, in different styles and colors to see what would fit best. We guessed on size and got it right. She was as discreet as possible and it was a very pleasant experience.

[HollyGreene]

I can't remember the first thing I bought for myself, but I had already bought my girlfriend underwear for birthdays and Christmas on many occasions, so when I started buying for myself, it was no big deal.

[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 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.

[Kris Burton]

Holly - I had just the opposite reaction. Like you, I would often buy items for my wife, if i was going to the store she would ask if i would pick an item up for her, pantyhose, panties, whatever. No big deal, and Icertainly did not care if anyone saw me. It was for my wife.

However, when I went to buy pantyhose for myself - a very different story! nervous and excited at the same time, going through the selections to get just the right size, style color I desired. Checking around to see if anyone was looking. I'm completely over the paranoia and nerves now, but I still find it exciting to shop for all manner of clothing!

[lisalove]

10 years old and finally allowed to ride my bike out of the neighborhood. I rode the 2 miles to K MArt and bought a white padded bra, because I wanted boobies and in my young mind that's how you got them. All the g irls were wearing bras and they had boobies.
I got my bra home and tried it on, but the boobies weren't as big as I had hoped. So as soon as I could, I rode up to K Mart again and bought a bigger gold colored padded bra, I was pleased wit htheir size this time.
I still have both bras, I have no idea how they managed to escape my mom's purgings of my stash.

[Geena75]

I was about 20 and went to the Meijer store and bought pantyhose. I was amazed at how it felt to buy a pair that fit. Since then I would have a size written on a piece of paper to make it look like I was buying for someone else.

[Sometimes Steffi]

I don't remember which was the first, but I remember the first 3 (all at Sears, after checking out the catalog):

1. Two leotards and three matching tights
2. A matching set of a bra, panty, cami and half skirt
3. A bra and a long line bra

[GracieRose]

A long blond wig at McAlpins (a long defunct local department store chain) when I was a teen. I saw an ad for it in the Sunday paper and I just had to have it. I drove to a store across town (rather than the local one where my sister worked). I had a "cover story" about how a group of us were buying it as a joke for a girl that hung out with us. In retrospect, I'm sure that the sales lady didn't buy the story and knew who the wig was really for, but she went along with the flow and made a sale.

[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.)

[DebbieCD]

I'd bought hold up stockings before from a super market and while it was exciting nothing compares to buying my gold strappy heels. Buying things is a tricky situation for me since my wife doesn't know and we share a bank account, the last thing I wanted was a query on why I was buying something in a women's clothing shop. At the time I had got a job in the city and had been quietly taking money of the account for lunch and saving some of it. When the time came to buy the heels I was so excited and scared that I thought I was going to be sick. I found what I believed was the right size and queued up to pay with the rest of the women (I was the only male in the shop). I had to try really hard to control my nerves, I paid and I was SO excited about buying them I had to try them straight away in the only private place, the work toilet. That was over 10 years ago and I can still feel the excitement and fear just thinking about it. (and yes I've still got the shoes!) When I think about it now though it was silly, nobody was probably even thinking I was buying them for myself, but in my head EVERYBODY there knew.

Later on I ended up buying even higher black court heels and a skirt from the same shop, (items I still have and wear today) and while they were a buzz, it wasn't quite like that first time. The Pink Fog has grabbed a hold of me BIG TIME now though, so I expect my stash to grow quite a bit over the next few months, every extra purchase is exciting!

[BobbiKay]

My ex and I had some fun with my underdressing. We were in an off-price store (C-Mart) and I found some thongs. She got the white ones and I got the bright blue ones. So my first purchase was a mutual one. Sadly, she moved on for reasons unrelated to dressing.

A few years ago, the urge to dress hit me again. My first purchase was cotton briefs in a couple of sizes, since I had no idea what my size was. Again, from an off-price store (Ollie's). I've moved on to thrift stores. Never had a problem (in the Before Times) asking for a fitting room to try on jeans.

Lately, it's been the thrift store outlets, where the things that didn't sell for $5 go for $1.09 to $1.59 per pound. Never gotten a look or a comment at the check-out.

I always pay cash.

[StacyG]

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

We had them in our local mall up until a few years ago. I bought tons of stuff there. Now they are online. I miss shopping there in person.

[Lorna]

When I was young (1950s) it was not at all unusual for children to buy nylon stockings as a birthday or Christmas present for their mothers. I did it several times. When I was in my teens and had girlfriends, they too sometimes mentioned nylons as acceptable gifts. It really wasn't unusual and caused no embarrassment whatever. Slightly oddly, when stockings gave way to tights it seemed to be different: neither my girlfriend my mother ever suggested a pair of tights as a present and I never bought any for them. However, because I had done it so many times, I never gave any thought to buying tights or stockings for myself and never encountered any suspicion on the part of shop assistants.
Of course, it was rather different with other items of women's clothing and I did find it somewhat intimidating when buying underwear and have no idea whether the sales people knew what I was doing. Subterfuge such as the "shopping list" from a wife or girlfriend seemed to work, especially as I could use relatively small sizes. Only on a couple of occasions did I leave a shop empty handed because of reluctance on the part of saleswomen to serve me.

[sometimes_miss]

I was lucky; had an older sister 6' tall, who went through clothes pretty fast, always storing the 'old' out of style stuff (basically anything from 'last season') in the attic, so I had an extensive wardrobe at the ready whenever I wanted. But of course, the one missing thing, was stockings, as they were tossed out routinely when ruined. So that was my routine item, picking them up when I went food shopping for the family. I always wondered if my parents thought it unusual that I always volunteered to do the food shopping as soon as I got my driver's license. So that first time, I was 17. L'eggs pantyhose. Suntan color, queen size. I would wear that brand for years. The up side, it made me acutely aware of my foot hygiene and toenails condition. I think I still have some of those plastic eggs that they came in!

[Nylon Wendy]

Black stockings when I was about 14 years old and I absolutely loved them.

[Rachael Fernandez]

My first purchase was after I had told my wife how much I liked wearing her knickers. Together we purchased a lovely pink nylon full cut panty at Target.

I loved those knickers so much and over the ensuring 44 years I have ventured out many times to add to my collection.

[Jessica Snow]

I used to go back to Scotland for Easter and summer holidays. One of the highlights was raiding my aunt?s underwear drawer. I?m not sure if it was normal in those days (mid 90s) but she had loads of stockings, suspenders and slips. I was l always careful and put things back folded in the right place.

Eventually I wanted to get my own things to have at home so at the ripe age of 16, I worked up the courage to go to M&S at Cameron Toll in Edinburgh. I knew what size of slip and panties I needed but had no idea about bra size. So some nice sales lady about 40 (which seemed ?old? at the time) asked if I needed help. Gave some bs line about it being for a girlfriend and she was ?the same size as me? 😂 Ended up getting a lacy black and a lacy white one with D cups as she thought it would give a more feminine shape. Loved the way it looked like I had real boobs under a full slip or nightie.

She even asked if I wanted to try it on and I just went bright red and said no thanks. Ended up going back later that week and got a skirt and heels. And I?ve been a Marks girl ever since! Still have the slips but no clue what ever happened to the bras.

[Melissa73]

My first purchase occurred when I was 20 attending college in St Louis I went to Target. I had nervously walked around the store wanting to buy something took me about 45 minutes I finally picked up the phone black leotard with some tights I remember I was excited but nervous and scared. But I did it

[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.

[Amanda77]

My first purchase was a couple of bras and panties. It was the first time i had driven to the city by myself with my own vehicle 🙃 at 16. Bought them at Canadian superstore. Two different styles of bras in the same size wanderbra i think. On my way home I stopped to eat at a fast food restaurant and as it was fall, i put one of the bras on in the restroom under my heavier clothing. Wat a sensation driving home with my very own bra on. It fit not to badly ether.

[lindsayhose]

When I was 16 it was 3 pairs of pantyhose I bought with my own money I was with my mom both scared and excited at the same time

[NjJamie]

Lindsay, did your mom know what you were buying? Please share the details, it sounds like quite an adventure.

[Wendy-Lyn]

Gee... I can't actually recall for certain. Probably panties and/or a bra
and I was probably mortified.

I used to get so embarrassed buying for Wendy-Lyn, but nowadays, if
I want something, I just put on my 'big girl's panties' and simply buy it.

I've bought a few dresses, tops, bras/camis and panties recently, all in
'guy mode' - oh, and a pair of sandals (can't 'do' heels). I know my dress
size (Australian size 14, sometimes 16) which makes things much easier
and less stressful, but if I buy something which doesn't fit I simply return
it for a refund or exchange.

I also bought some makeup the other day (mascara, eye-shadow and
some lip-gloss, also some nail-polish), once again in 'guy mode'.

I've never had an issue with any of the SAs I've dealt with but, although
nothing's been said I'm sure a few have known or guessed that the items
were for me.

While I'd love to go shopping en-femme, I live in a small town (25,000
people) and so would surely be spotted sooner rather than later.

[Rachel Anne]

I don't know if it counts, but back in the day, you could order from the Sears catalog and do an instore pickup. You'd get a card in the mail saying your package was ready, at what store. You'd go pick up the bundle and the cashier would just ring up the total.

I had just got my own place, and my big plan was to live full time over the summer between semesters, so I ordered quite a lot with some money I had saved up. My plans didn't quite work out that way, but it sure was fun.

[Majella St Gerard]

Panties in male mode

[giuseppina]

I don't remember whether it was a girdle or an AIO bodysuit. Both were confiscated.

[Mermaiden]

Stacy?s post, initiating this chain, does a wonderful job sharing the anxiety of the first purchase. I felt I wanted to reach out to her 15 yo and reassure and encourage.
We?ve all been there.

[StacyG]

Stacy?s post, initiating this chain, does a wonderful job sharing the anxiety of the first purchase. I felt I wanted to reach out to her 15 yo and reassure and encourage.
We?ve all been there.

Thanks, but I wouldn't change a thing about that or any of my other awkward shopping experiences. They're all a part of my journey. I eventually got the courage to spend as long as I wanted in the stores browsing and deciding. One day at Sears I was probably 18 and it was Christmastime and mall was packed. I kept going back and forth between a pair of red tap panties and baby blue satin PJ short set with light pink collar and pocket and hem around the shorts. While holding the red satin tap panties, a man walked by and said "That's not your color". I wasn't embarrassed at all. I bought them.
Another time at Mervyn's I found a beautiful teddy that was a metallic blue satin on the front and black sheer mesh on the back. The SA was quite a bit older and was trying to explain that the cups were really small and if the person I was buying them for was big in the upstairs area, she might pop out. She was more embarrassed than I was.
I can relate to so many of the memories that have been share here. I love it.

[StaceyJane]

I bought a skirt from K Mart. I was so nervous, but I felt so happy after I finished.

[RachelB.]

Way to many years ago to remember for sure. I think I bought a dress at Sears.

[Jessica Secret]

A white lacy/chiffon bridal nightgown/negligee from Dillard's, couldn't resist how beautiful and gorgeous it was.

[cosmolovesph]

Pantyhose without a doubt, probably No-Nonsense brand and yes, those first few times were a bit nerve racking, looking back now - who really cared? What you (or I) were buying had zero impact (other than a sale) on the sales clerk and if you purchased in a place you don't normally shop, you'd probably never see that person again. I remember one time I was on the road, went to a Dept store, purchased a few pairs from this store we didn't have at home and slipped on a pair once I got in the car. Made that drive home much more interesting and kept to the speed-limit as I didn't put my pants back on and getting pulled over would then be really embarrassing. :)

[JaneAshland]

Pantyhose of course!

[Lillianna]

My first in-store purchase was a pair of frilly panties and some lace top stockings.

[suezeq]

for me it was a bra with matching panties @ a roll on panty girdle

[Lacey New]

My first in store purchase was in a department store in a large mall close to closing time. I had seen a sale on panties advertise in one of inserts in the Sunday paper. I,was,living by myself in a small apartment so I drove to a mall quite a distance from where I lived and purchased three pairs of Pam nylon briefs, one pink, one pale blue and one white. When the sales associate rang up the purchase, she said remember, pink is for girls, blue is for boys. I was so nervous and wanted to get out of there so I just smiled and was speechless.

[melissa25]

My first purchase was a summer dress when i was traveling through europe, it was the most beautiful, i foget the store but i bought it in italy. Sadly i had to throw it away when i came back home because at the time i lived with my parents and i didnt want them to know

[Sometimes Steffi]

Way to many years ago to remember for sure. I think I bought a dress at Sears.

I still have a video memory of some of my first purchases. If it had been an awful experience, I would have had PTSD as a result.

[Jeanettew]

My first ever was in a Bras and things shop coming up to Valantines day went in and the assistant asked if she could help and I said I was looking for something sexy for my wife so she helped me out bought a bra, panties and suspenders and stockings, she wrapped them nice and i could not wait to get home rip of the wrapping and put them on.

[Rebecca Cross Bracer]

Dozens of pairs of pantyhose before ever buying anything else. Small, fairly discreet, and by far the item I need the most.

[Paula_56]

I was 22 and had just started my new job with a high-tech company in Clifton, New Jersey. There was a dress shop in town that I walked by each day during my lunch time walks. It was an old fashioned kind of place that you don?t see any more, locally owned and operated.

It was the 80?s, so think Designing Women style dresses (sigh). Well, there were all kinds in the window, but one caught my eye --- a blue print dress with a belted waist and lace collar.

After several days, I decided that I had to have it. As it was early October, the Halloween excuse was perfect.

It took several days of trying to even go into the store. I have to laugh now --- like a secret agent I made sure none of my colleagues were out in the area and I doubled back a couple of times in front of the store.

Finally I opened the door and a loud bell deliberately announced my arrival. Sheepishly, I made my way toward the back of the store and a middle-aged lady looked over the rim of her glasses appraisingly. My heart was pounding; my face was red as I stammered out a request for the dress in the window.

She was very pleasant and settled me down. She took my measurements, determined I was a size 16, and pulled a similar dress in my size from the rack. She then proceeded to sell me an expensive bra and then a girdle along with a pair of my first Hanes Silk Reflections, the brand I still wear today. Looking back, I think she saw right through me and was an expert saleswoman.

I walked back to my car and hid my purchase watchfully as if I had just bought something illegal.

I never wore the dress outside my bedroom. The dress and foundations would be lost in one of the Great Purges of the 80?s. However, an important step had been taken in my journey: I bought my first dress!

[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.

[Kathi-Anne]

JC Penney beige tights
Danskin ultra shimmery footed tights,light toast.

[Girly bride]

My first real purchase was a nurses outfit dress with matching silk panties and bra about 20 years ago now Absolutely loved them

[dbweb]

I can recall my first shopping trip, I was working in Midwest area and had to drive about an hour to get to a decent size town with a ladies wear store in it. I was met by a sales lady and asked about buying a gift for my wife, I am sure they heard this many times but when I mentioned I wanted to buy her a very nice bra, it got her attention. Of course she asked if I knew her size, and told her I checked one of her older very plain bras and found the size to be 42B, which would happen to fit me as well as and experienced sales lady would recognize. To make a long story short, she showed me several quite expensive bras, and I did buy a nice lacy version, complaining a bit about the price to which she explained that these were designed to not only look good but also to provide the needed support, thinking that I was an engineer by the way I dressed and spoke, she expected me to understand this. As I left with my purchase, she smiled and said, I hope you enjoy your new bra, my cover being blown as I left the store. In the end it was worth it as I certainly did for many years!

[Phoebe Reece]

It was in Rich's department store in Atlanta (the main store downtown) in 1968. I was a senior in high school and had a part-time job there. I bought a a package of 3 pairs of pantyhose and used my employee discount for the purchase. I was not asked who they were for and I didn't volunteer anything about it.

[Jamie MacFaile]

Gosh, it's been so long; but if I remember correctly it was a pair of Candie's slip on heels; at a big box store, the SA winked at me as I tried them on.

Since then, though, I've shopped en femme at JC Penny, Macy's Kohls, and a locally owned resale shop where the owners took real interest in me.

Janet's Closet was first; bought wigs and a LBD, very helpful folks specifically for CDs.

Now I even grocery shop en femme.

[Angela Marie]

When I was about 12, in 1966 I went into a Woolworths store and bought a pair of red tights (basically what leggings are today). I was nervous that someone I knew would see me. When I got them home I hid them and would wear them when my mother was out.

[Pixie_94]

Maybe it was not too long ago compared to what most tell here, but I remember it was during 2014, around July or August. I used to walk back home from university and I weeks prior I noticed a nice little store in the city, a lingerie shop (or something close), there were a few attempts of going there, but I was often awkward or feeling shy about it, until one day after some classes I stopped before I continued heading home and stopped by the shop, still feeling awkward, but I tried to keep my cool and bought two thongs (wrong size at that time, to make it worse).

It's been quite a while and I don't keep any of that. I still don't know how I got the (quasi)confidence I had to do it.

[Nell27]

Two years ago at a Goodwill store. After much fidgeting around, I picked out a simple knee-length nightgown with lace edges and purple ribbons. Occasionally, I slip it on when my wife is already in bed and it gives me soooo much comfort and peace to wear. 🌷

[LydiaL]

Quite a while ago now, but I believe that it was 3 cotton miniskirts purchased from Ross. The price was right and the pink fog had rolled in. Died one so that I would have 3 different colors.

Of course, that was not near enough, so the binge to buy more ladies clothes was off and running!

[fly2188]

I was at an internship a few states away from home and went to a Walmart and bought panties. I wore them the rest of them summer, but did my first purge before I went back to college that year.

I was so nervous going into the store and felt so uncomfortable walking through the womens section.

[Crissy 107]

Yesterday I was at Walmart and of course I walked through the women’s section. I saw one of us very nervously looking at the multi packs of panties. I smiled to myself that I can remember when that was me. A short while later I saw him on line at a checkout clutching the multi pack to hide it from view, it was the only thing he had. Unfortunately the self checkout was closed for some work.
I felt bad he was so nervous

[jjjjohanne]

I posted previously my first shopping experience for pantyhose in a grocery store. I ended up buying pantyhose in a grocery store several more times. A few years later, I got up my nerve and went into a small, $1 store, and bought a pair of unflattering, silky panties. They were the only thing I purchased. The two cashiers made no comments to embarrass me or to comfort me. It was probably awkward for everyone involved.

More years went by and I went to a mall far from home. I went into a ladies' clothing store. A sales woman approached me while I was near a ladies' underwear display. I asked her a couple questions (not revealing that I was shopping for me). I did not select anything. I shopped around the store some more. Then, after collecting my nerves, I asked the sales lady if they allowed men to try on clothes. She said, "Oh sure!" and started moving with purpose. She took me to the dressing room and sent me in with the blouse that I had. Another sales woman started helping. They started bringing me more sizes and alternative options to try on. I was blown away! I never thought anyone would proactively help me crossdress!! For them, it was not a first time...

More years went by and I went Christmas shopping while wearing men's shorts with skin-tone pantyhose. The next year, I did my Christmas shopping in all women's clothes including shorts, a plain top, skin-tone pantyhose, and shoes (invisible crossdressing!!). A couple years after that, I went Christmas shopping as a man in a skirt. THAT was very stressful! Basically, everyone treated me with respect and tried to ignore the fact that I was crossdressing.

...and, I've gone out quite a few times while dressed pretty since then... (https://joeypress.wordpress.com/)

[Jolene G]

My first in store purchase was a few weeks ago going to Walmart and buying panties.

[Veronica Lacey]

Welcome to the forum, Stacy.

So, so many purchases since the first. I've certainly lost secure recollection of it but I believe it was a white satin camisole and slip, items that were easy to eyeball for size. It would have been the same scenario, Stacy, and same age: ride the bike to the mall with paper route money in pocket, make the purchase, race home with the bag nestled under my jacket. It took me quite a spell as I browsed the store in a complete euphoric, virgin fog of satin, silk and lace. In store my face must have been somewhat flush as I wrestled between nerves and purpose. I even "circled" that section of the mall a couple times sizing up the store to ease my anxiety about going in. I knew that once I was in there was no going back and that I would not be denied. That was quite a few purchases ago...

Became a bit of a personal habit to literally waltz the entire lingerie store several times taking in what I saw, imagining how something would feel and if it would fit before purchasing. Today, indeed, online resources have helped hone in on exact sizing and access to so much more than I could have evert imagined.

[Lacey New]

Jolene, congratulations! Good for you! It gets easier as time goes by.

[MostlyMK]

A red top, black miniskirt, and knee-high gogo boots at Target. My high school was having a homecoming thing that involved crossdressing so it was my first chance to try it for real.

[Emleeboy]

I bought a pair of black thigh high nylons at a Walgreens like place in my early 20?s? at the time i was in college, lived with male roommates who had no clue that i would prance around the apartment wearing them with panties I took from my girlfriend.

[Heather76]

Yesterday I was at Walmart and of course I walked through the women’s section. I saw one of us very nervously looking at the multi packs of panties. I smiled to myself that I can remember when that was me. A short while later I saw him on line at a checkout clutching the multi pack to hide it from view, it was the only thing he had. Unfortunately the self checkout was closed for some work.
I felt bad he was so nervous

That wasn't me you saw; but, I can relate to that poor fellow. My first purchase was at a Dollar General when I bought a 2 pack of Hanes microfiber panties. Then I went to a Kohl's and purchased a pair of Maidenform lace panties. I liked the lace so much more. My next purchase was when I discovered Secret Treasures lace panties at Walmart. I did have 3 or 4 other items I legitimately needed to buy while there. I was a bit nervous when I got in line to check out and had a young female check-out clerk. That was the last time I've ever been nervous making a purchase of lingerie. Yesterday I stopped at a Walmart and purchased 2 lace bralettes and a 3 pack of 'Leggs thigh high stockings - and nothing else. BTW, I only buy the Secret Treasures lace hipster panties as they fit me perfectly and I love the look.

[Raychel]

I think the first thing that I would have bought for myself would have been panties at Victoria Secret
They had some really nice ones back in that day.
Now they don't have anything at all that I like.

But now I can walk into just about any store, browse the women's section, and if I see something I like, In the shopping cart it goes.
I dont look back, or even think twice, No one at all cares what I am buying

[1Ladyjade]

My first in store purchase was a bra and lipstick. I bought them at Wal-Mart I rolled past the bras going real slow trying to find something that I liked. There was a woman standing right where I wanted to go. So I went off and grabbed other things and then came back to find the bra I wanted not in my size. So I rolled around the rack and found the perfect bralette for me. Lot's of lace and black of course. The lipstick was easier to grab. I made the mistake of not looking at the actual lipstick and the color ended the same color as my lips. So I had to go back and buy a second tube. This time I took my time checking the actual color.

[Melanie Sykes]

The first purchase I can remember making was a pair of "Elle" fashion socks from Debenhams when I was old enough to travel to the city on my own. They were powder blue with a small "Elle" logo at the top of each sock. Seems an odd choice of thing to buy now, but at the time it seemed fairly "safe" I suppose. Some time later (still a teenager) I bought a matching set of very pretty white underwear (knickers, bra, suspender belt) for my girlfriend from that same Debenhams store. The sales lady smiled and joked that they weren't really my style. I was able to laugh back without any self-consciousness because they actually weren't for me. If they had been, I probably would have died when she said that. Fast-forward a few days and my girlfriend "didn't want me to think of her in that way", and she asked me to take them back, which I DID NOT. They fitted me very well, and I enjoyed them for a long time, which is more than I can say about the girlfriend.

[Crissy 107]

Melanie, Funny story and perfect ending!

[EricaNG]

A pair of 4 inch black heels at age 16

[SylphDevine]

My first purchase was at a Victoria's Secret when I was a teen. I was sooo nervous, but the salesperson figured it out and was quite sympathic. She helped me pick out a garterbelt, stockings and three pairs of panties.

I was in heaven when I got home and had some alone time. I wonder what ever happened to that stuff?

[Alice92]

It was a red dress. I said it was for my girlfriend, I don't know if the saleswoman believed me. She probably didn't care...

[Karen G]

I don't remember precisely but it was definitely back when I was just a kid, 11 or 12 maybe. I lived in a rather small town but the urge for wearing beautiful clothes was huge. 30 years later, I haven't outed to anyone yet, but I know that nobody really cares about what you buy so I just shop almost as I was shopping male clothing, except for the try them on part.

[Alisonforme]

These black strappy heels

326302

[Brianne_bc]

Highheels were my first instore purchase. I always buy from women though. Just cant buy from a male clerk.

[Beverley Sims]

One early in store purchase was a dress and I was fitted with a bra.

A Hickory Tweenage Bra.

An Aunt bought the items along with a dress for my cousin.

[Philippa Grace]

Hold ups from a supermarket,(Tesco), I usually do the weekly shopping so it probably looked like I was buying them for my SO, but actually no one cared! Now I Always have hold ups in my drawer, and can easily go into any shop and buy all my femm underwear, I am more confident and no one cares.

[Sandrajiggle]

There was a shop near where I was working. They were a sort of homeware store which I had shopped in for homeware. But I had seen there were also clothes for sale. I'd noticed that they had foundation wear.
I thought about getting something for myself for a few weeks before eventually feeling almost desperate enough and having convinced myself no one would care. Set off one lunchtime.
I did start off wandering around the ironing board s, kitchen utensils and general hardware.
From a distance I scoped out the lingerie section.
Without much browsing I put a 36c Doreen longline bra into my basket, then emboldened added a pair of size 14 support panties in matching white. I must have become drunk with the experience and added a black size 14 pencil skirt with out any fear.
At the till the salesperson did not give any suggestions that I was buying anything out of the ordinary.
I couldn't wait to get home to try everything on.
It was a while before I bought anything else. My next items came from a well stocked costume department at work. I didn't need to shop.

[JulieC]

Hold ups from a supermarket,(Tesco), I usually do the weekly shopping so it probably looked like I was buying them for my SO, but actually no one cared!

Many years ago, I bought some pantyhose from a grocery store. The cashier was correct in assuming they were for me, though I didn't confirm her suspicions. She was snide and insulting. I didn't say a word to her. I paid and left. Nowadays, I would take a different approach and have a talk with her manager. It's the only time anyone ever gave me any kind of grief over buying clothes of any kind.

[SexyKerri]

Beautiful shoes

[Cacique82]

The first time i ever bought was panties from Shopko ..

LOL. Same for me. Vassarette. Wish I still had them.

[Fiona Lindum]

First purchase was a pair of tights from the supermarket.

[Itsjustme]

Mine was a simple sleepshirt at Wal-Mart. I was so scared I didn't check that the size on the shirt matched what was on the hanger...I got home and the size was four sizes higher than the hanger said!

[Jessax101]

This is a very popular post as it applies to everyone that has shopped for womenswear and cosmetics. Won?t delve into specifics but first shopped for lipstick, eyeshadow, liner, foundation, concealer, etc. then proceeded to underwear, tight pants, etc. people would glance at me and do second looks, especially at the cosmetics isles, especially when I didn?t exactly know what I needed and how it was used. Checkout clerks looked very timidly and sort of grinning, but didn?t really care. If someone would ask, I would have said my wife sent me for these items, lol.

Don?t think I?ll have to worry about bras and cups cause I will be happy flat.. I work out and pecs show off a bit so I will be happy flat chested. Thanks for the interesting post!

Jess??