What was the first article of female clothing you bought for yourself? How did it go?

[Patience]

Mine was a blue and white floral skirt from the dollar rack in a thrift store. It literally cost a dollar. It didn?t look brand new, but it didn?t look old, either. I felt a bit nervous when I was buying it but the experience was so pleasant I went back many more times, once in full femme, as the thrift store is only a few blocks from where I buy my wigs. I still have it and wear it to lounge around the house.

What did you get first?

[tifftg]

I think I was 13 or 14. I had already been diving into my mother's items for a while and wanted to have something of my own. I walked up to the Ben Franklin store (dating myself) and bought a pair of Leggs Pantyhose in the plastic egg. I was so nervous and so thrilled.

[wendy]

I bought numerous items as my first item.

It was when i was a first year University student, just received a student loan. I didn't know what the word loan meant, but when I got it I noticed my bank account swell so I thought it was like free money. I worked up the courage and headed to K Mart, and bought some shapewear, swimsuits, and early 90s aerobic wear + spandex leggings. I was so nervous as it was the first time I walked around the women's clothing area in a dept store by myself, yet at the same time I felt like a kid in a candy store. It was even more nerve wracking as I headed to the cashier to pay for all of it.

Sadly, and with much regret, I purged all of those items.

[Teresa]

Patience,
My first items were a complete set of Charnos matching underwear , that is , panties , suspender belt , camisole , bra and slip all in a laurel green shade and then chose stockings in various shades . How did it go ? Well I'd written down my sizing and told the SA I wanted to buy the set for a Xmas present for my wife , I showed her the piece of paper with the sizes on telling her I'd checked the sizes on my wife's underwear but if they didn't fit would it be OK the exchange them , most SAs appeared to be happy with that .

Then one day I ventured into a shop in my own town with same story , I stood by the racks of underwear when the SA called across a crowded store to another SA , " Lady's underwear for the gentleman !" The reply came back , " Ask him to wait by the knickers !" I was glowing as red as the underwear I was standing next to but I didn't back down there was a 50% sale on and I wasn't going to walk away empty handed , those two girls really did have some fun with me much to the amusement of other shoppers .

In those days the choice of underwear was amazing with complete matching sets in fabulous colours and you could buy stockings from most shops .

[bridget thronton]

A navy skirt and grey blouse - it was a bit nerve wracking

[JenniferR771]

My first item was a pink prom dress. I bought it at a garage sale. In September. Told the lady it was for a Halloween dress-up party. She offered to let me try it on--but I declined. She said, "You are going to look beautiful in this!" I hid it behind the seat of my pickup for a year. Later in my garden shed. Eventually it was purged when my wife and I had counseling. The "expert counselor" convinced me I had transvestic fetishism. He convinced me to purge to help cure my habit. I soon started to buy a lot more at my favorite thrift store.

[KrissyTN]

I was around 18 and had been dressing for years - mostly female family members, bras, stockings, panties. I remember my Mom had a yellow bathing suit with cups....loved that, with pantyhose and a matching pair of yellow high heels she had! But, I digress. I went to a local mall where they had a "Fredericks of Hollywood" store. I purchased two garter belts, and two pairs of stockings. I still have one of them.

It was a thrilling day!!

[Tracy Irving]

The first thing I bought were a few pair of panties. It was so long ago that I don't even remember the experience so it couldn't have been all that exciting.

[BrendaPDX]

Mine was a dress from a thrift store. It fit "perfectly", if I wasn't already hooked this dress certainly set the hook.

[JennniferMcC]

I think mine was when I was12 or 13. Probably that pair of black hold ups with rhinestone embellishments at the ankle from a department store. Nerve-wracking but definitely exciting!
-Jen

[MaryAnn1963]

Leggs pantyhose in the plastic egg. I was 16 and just started my first real job. I kept them in my car and wore them at work.....

[Star01]

It was some panties and lingerie I bought in an adult gifts store where I could say "it's for her and she is about the same size as me" as the clerk looked me up and down and thought to herself "sure buddy, I have heard that story before and I know this is for you". Shopping anxiety and discrete storage have both been a challenge for me so that's another thing I need to change.

[NancySue]

Nylon stockings and pantyhose. I was nervous 😬. The SA sensed it and was very nice. I couldn?t wait to get home.

[Crissy 107]

I was about 18-19 yo and went into NYC where nobody knew me and I bought panties, garter belt and stockings. Looking back I am surprised I had that much nerve. Unfortunately I dumped them in my first purge.
Whatever you do please do not ever purge.

[gownman]

A Miss Elaine nightgown. In fact nighties and slips are my only CD interests. I have a largish collection of gowns, robes and slips, all soft silky nylon.

[Angela Marie]

When I was about 12 I bought a pair of red tights (would now be called leggings) from the local Woolworth store. As many here have mentioned I was really nervous lol.

[Bea_]

in my mid-fifties i tried on a few pairs of my wife's panties, liked them, and decided to try and buy my own. I ended up in a dollar store and found a small selection of panties on one of the aisles. I grabbed 3 or 4 pairs as quickly as I could without really checking the size. i grabbed a few other 'decoy' items and went to the register. As my cashier was checking out my purchase her face showed pure disgust. I'm surprised that my reaction was less of embarrassment and more of a "screw you" attitude. The panties all turned out to be too small and were purged. Shortly after that i had the talk with my wife. She ended up "taking me" shopping and i walked the store while SHE picked out my first proper panties. She actually surprised me at the range of her taste. I think giving her some control at the beginning has been one factor that helped the relationship as my taste has expanded.

[Dawn P]

I was 18 or 19 still living at home although I owned my own business.Could only dress when parents went out of town.

[Robertacd]

I don't even remember, I am guessing a bra I purchased when I was in college.

Nothing sticks in my mind about it being traumatic or me being overly terrified.

[kimberly c]

Panties, garter belt and thigh highs.Awesome feeling.

[Jenny22]

It's been sooooo long ago, I don't remember!

[Micki_Finn]

Gypsy skirts at a thrift store in Santa Cruz. Those things were so comfortable.

[Katherine L.]

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.

[Lana Mae]

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

[Kandi Robbins]

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!

[HollyGreene]

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.

[HelpMe,Rhonda]

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.

[cdinmd206]

Black garter belt, black stockings and black see thru full cut frilly panties.

[Stephanie47]

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.

[BobbiKay]

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.

[dominique]

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.

[Tanya silk stocking]

My first purchase was a gorgeous under wear set in black consisting of garter belt, bra, knickers and full length silk slip

[Diane Smith]

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

[alwayshave]

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.

[Elaina]

My first purchase included a few different items: a white, pleated skirt, a peach-colored top, a pink-tinged dress, and some undergarments.

[Kay J]

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!

[Michele14]

Matching panties and bra. I was around 30 years old. Guess better later than never.

[GenevieveF]

My first purchase was a pair of 4 inch stilettos with an ankle strap.

[Denice]

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.

[Cacique82]

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.

[MysteryWoman]

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.

[jacques]

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

[michellecd9999]

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.

[helenejo]

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.

[Crissy 107]

I think most of us remember our first purchase with fond memories.

[JenniferWhenCD]

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.

[Karmen]

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.

[mbmeen12]

Opaque pantyhose.................

[susan2010]

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.

[Raychel]

mine was pantyhose from one of those mail order companies,
monthly supply, lol,

How did it go :heehee:
I would say ok, here I am 45 years later, still dressing and loving it. :heehee:

[Linda E. Woodworth]

A pair of Leggs pantyhose bought at a Hotel gift shop when I was traveling in another state.

I figured I was far enough away from home nobody would recognize me!

[joanne51]

When I look back at all the clothes I have bought (mostly online), the one item that stands out as my first purchase without being mistaken for a Xmas present has to be a LBD.
To make the experience even more memorable was that I had to take it back and change it for a bigger size. I was so determined to have that dress that I overcame the embarrassment and was prepared to admit to the SA that it was for me. Lovely dress.

[April Rose]

I'm not sure but I think it was a garter belt. The one that really stands out, from around the same time, was a white nurses uniform. I got the notion in my head that it would be easier to buy because I wouldn't have to deal with color choice. I was really nervous, and the lady proprietor saw right through me, and was clearly enjoying herself. To her credit though, she helped me pick out a dress that looked good and fit well. No, I did not try it on.

[JenniferR771]

When I got up the nerve to go to a retail store not thrift shop. I bought a well-padded bra at Big Lots. But the next customer in line (who was with her 12 year old daughter), teased me. "I hope, that is not for you!"
She asked if I were a drag performer, on stage downtown.

[ShelbyDawn]

The first thing I bought, I honestly don't remember, It was probably something at a thrift shop.

The first thing I bought that I do remember was a bra at JC Penney. I had found it online and didn't want to wait to get it, so I waited until about minutes before closing and ventured into the location not far from my house.
I found the bra I was looking for. When a sales associate approached and asked if I needed any help, I said I had found what I was looking for.
She then said that the other men that shopped here and had bought that bra usually got the matching panties and she would be more than happy to show me where they were, and offered to show me a few other items she thought I might like as well.

Needless to say, I was blown away with her casual acceptance and, while it did make future ventures a little easier, I still get nervous shopping in person.

[Pixie_94]

I don't even have to say what exactly for it to be considered part of a fetish when it got discovered.

Buying it went smoothly, having it was stressful at times.

[Patience]

I don’t think anyone here will chastise you for naming the article, Pixie, but it’s up to you.

[Crissy 107]

Shelby, What a great shopping experience, I would have been back there the next week.

[Pixie_94]

Okay, it was underwear, two thongs, which were the wrong size by just a little.

[Maryannginger]

Spandex dress/bra and i have a really nice feminine figure in it if i stuff a bra.

[BTWimRobin]

Hi Patience,

As you may, or may not, know I was a late bloomer, finally admitting to myself, last year, I needed to let my feminine side out. About a year ago I went on my fist shopping excursion and I wrote about it here: "https://www.crossdressers.com/forums/showthread.php?264672-The-World-Did-Not-End-Today-It-Got-Better"

[darla_g]

I would think technically its some clothes , a nice flouncy skirt & a top that i got to do a Halloween costume. How cliche can you get? Forgot where these came from

[Ericka_d]

Probably a pair of womans jeans. At that point. I wanted some thing I could also wear as a male.

I went to the department store. Located the jeans, and grabbed a few pairs. Then headed to the fitting room. Found a pair I liked. Paid for them and left.

Its been almost 10 years since. I was nervous then. Now I can buy any thing female related. With out even caring. Probably because I'm more comfortable with who I am now.

[NancyTO]

I think I was 13 or 14. I had already been diving into my mother's items for a while and wanted to have something of my own. I walked up to the Ben Franklin store (dating myself) and bought a pair of Leggs Pantyhose in the plastic egg. I was so nervous and so thrilled.

Same here. Walked to the grocery store 20 minute away, and was nervous sweating like crazy when I brought the Leggs to the check out counter.

[Kimberly A.]

My first article of women's clothing that I bought was a pair of pantyhose..... It went VERY well! LOL

I've always loved pantyhose and always will. :D

[VtVicky]

A nylon slip from Sears Catalog right after I got an assignment to England after my least favorite wife and I separated. I can remember the fear and tension I felt going to the base post office to pick up the package. Totally safe but still pretty scary.

For you kids in the audience, the Sears catalog was what guys my age used before the invention of the internet.

[Crissy 107]

Vicky, Many of us here remember the Sears catalogue not to mention the weekly inserts in the Sunday paper. Simply heaven.

[Marianne S]

A good question here is what was the significance of that first item we bought? Isn't that what's really behind this question?

If we had little or no access to women's clothing before, then that first purchase might have been what excited us the most, or what we needed the most to start feeling feminine. It's not surprising that so many members' first purchases were of lingerie or underwear of various kinds: "intimate apparel," as it's so delightfully called. Though that doesn't have to be the case. It could be more about the enjoyment of looking "outwardly" female.

But others like myself may already have had access to women's clothing and underwear from a close relative. If so, that "first purchase" reflects something else. Like a first expression of personal taste, for example. In my case what triggered me into crossdressing was putting on my mother's floral skirt at the age of twelve or thirteen, but that quickly exploded into wearing her skirts, blouses, and dresses, and naturally all her underwear: her slips and bras, nylons, girdles and panties. Everything.

So what was missing? It was the desire to look like the girls of my own age, the girls who especially attracted me as a young teen. My parents clothed me well enough as a boy, but I didn't have much money to spend on girls' clothes. These were relatively expensive in relation to my adolescent budget, which didn't even cover things like all the records that I wanted. (I trust that many here are old enough to remember "records"!)

I wrote that before I read Vicky's comment. I've got to giggle at her mention of the Sears catalogue, It ain't that old! I think they discontinued the printed version in the 90s. "Records" disappeared when CDs made their entrance, half a generation earlier.

So my own first purchase was a simple white blouse similar to some worn at the time by the girls in school that I so much admired. And yes, you bet I was nervous when I went in to buy it, facing a sales assistant over the counter at a small local store. I was asked no questions, but I imagined her asking me "Why are you buying thia?" "Well, it's for my sister!"--a sister that I never had. I had to guess at the right size. Luckily I wasn't far off.

Anyway that's what's attracted me more often than not to particular items of women's clothing. Nothing outrageously erotic, "different," bizarre, or "over the top," but mostly the desire to look and feel like ordinary women I found especially attractive, and to wear what they wore--even if today I'm "old fashioned" in my preferences!

[sara66]

I bought a black lace Bali body briefer from the Playtex/bali outlet. I was so scared I thought I was going to explode. I printed a pic from their web site and wrote down the size for my "wife". The Sa could not have been nicer. I think she did realize it was for me, but nothing was said. Its funny how many things for "costume parties" and for my "wife" I bought before I was married. Now I just tell the SA's its for me. Most of them think it fun to help me find stuff.
Sara

[Lacey New]

Panties. I lived by myself in a small apartment And I had to buy decent clothes for my job. So I shopped at Macy?s and had a charge card. When the bill came one time, there was an ad for panties enclosed. I filled out the form and bought 3 pair of Pam nylon hipsters and 3 pair of Pam nylon briefs all six pair were white, pink or pale blue and had a nice lace waistband. I remember the first time I wore a pair under my trousers to run a simple errand to the grocery store. I was convinced that there were X-ray machines everywhere and that the panty police would be waiting outside to haul me off to jail.

[AndreaJay]

The first thing I ever bought for myself was a wrap-around satin mini skirt and a denim mini skirt. I still have the denim skirt, but I purged the satin one a short while ago in a clear out.

[JennyMay]

For me, it was a denim skirt off of eBay. Skirts have always been important to me. They seem to me To be THE feminine garment. Interestingly it was the ?buying it for myself? that was significant. Up to then my wife (I am blessed with a supportive and understanding wife) had bought things for me when I had asked or as gifts. Buying it for myself seemed to make it more ordinary and accepted, a step towards self acceptance. I never bought something for myself in a shop where a face to face encounter was required. I wonder if I will ever have the courage to do that?

[Ceera]

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.

[FairyCrossdresser]

I have two answers to this. The first item I owned (but which was bought for me) was a school uniform. When I was in the process of getting my head around my cross dressing in my teens I was referred to a counsellor who pushed the idea of ?full immersion? so I was dressed as a girl full time for a good while.

My first born addiction (although it has expanded considerably since) was skirts and for that reason, the first item I bought myself was a purple pencil skirt.

[Crissy 107]

The first item I owned (but which was bought for me) was a school uniform. When I was in the process of getting my head around my cross dressing in my teens I was referred to a counsellor who pushed the idea of ?full immersion? so I was dressed as a girl full time for a good while.

There must be more to this story, please tell.

[FairyCrossdresser]

Hi Chrissy

Basically, when I was around 11 My urge to cross dress arrived on the scene. Obviously, as a child I didn?t have access to any of my own gear and consequently ended up trying on my sister?s clothes whenever I got the opportunity. What I have found (and which was certainly true at the time) is that if I don?t dress for an extended period of time the urge builds, and a bit like putting a battery on charge, the only to release that feeling is to dress.

Now I thought I was being really clever leaving everything exactly as I had found it, but mother?s being what they are, mine caught me out on a number of occasions (albeit, not in the act).

At the time, I would have given anything to have stopped. My mates at school would chase anything in a skirt and so it was a source of great distress that I was more interested in wearing skirts. It was much more a compulsion than a hobby (even today I am driven primarily by the urges but am more accepting of it).

Anyway, due to my distress, I was referred to a counsellor who (after a number of sessions, determined the best course of action was ?full immersion? in the hope that I would lose interest and consequently I found myself dressing as a girl both at home and at school.

Naively, I tried to just be a boy in a skirt at first but I was naturally shunned and with my parent?s insistence, I realised my only option was to become one of the girls. Within only a few weeks I had gone in school from being a typical lad playing football and talking about girls to one of a gaggle of girls doing each other?s hair and makeup. For the last couple of years of school I was more or less transgender.

It was partially my own fault that I had found myself in that situation but for the sake of my own sanity as much as anything, I just had to embrace the role.

It is probably the reason I am so confident publicly now; once everyone knows, there is no point hiding it any longer.

[ShoeziQ]

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.

[BLUE ORCHID]

Hi Patience, :hugs:. It was probably a Bra or Nylon stockings some 65years ago, >Orchid ..o:daydreaming:o..

[Wendy99]

Wow that was 60 years ago, I went into a lingerie store and brought a matching tan bra, panty, and half slip, it was nerve racking. For dresses and skirts I sneaked them from my sisters.

[mylilsecret8]

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.

[Jessica S]

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.

[susanmichelle]

The first item was a really beautiful black Brooks leather dress with sleeves that were open and thin 1/2? crunched straps and zipped up I might add it literally fit me like a glove. Oh to be able to wear a size 7 again. In 12?s nowadays but can always diet some.

[mmandy31]

i went into wal mart and bought my first panties and pantyhose when i moved out of parents house what a thrill to go panty shopping

[Sallee]

Its been a while but I am guessing a bra. It went fine I gave them money they gave me the bra easy. NO body cares as long as you are polite and pay for the item Whether you buying clothing, female hygine products or anything as long as you pay.

[Amy Lee]

I bought a pair of Pantyhose at JCPenny when I was about 17. The SA was about my same age and asked me if they were for me...being brave, I told her yes they were! She said "cool, I bet you would look nice in them!" I must have been 10 shades of red, but it was such a thrill!

[RachelWCat]

I was probably around 15 at the time and had been wearing my mum's and sisters clothing for a while but I wanted a pair of leather gloves of my own. I remember waiting until around Christmas to get them at Marks and Spencer so that if anyone asked, I could say they were a gift (that ridiculous paranoia still follows me to this day!) I remember being so nervous looking through the women's department for these gloves. It's ridiculous thinking about it now. Needless to say the cashier didn't give a hoot who the gloves were for. Soon after that I discovered the East of Eden range of mail order catalogues and didn't look back.

[Asew]

A longline bra from a lingerie store in a plaza when I was 19. I was super nervous and told the sales assistant I didn't need any help. When I went to pay she asked if this was for my girlfriend and I said yes. She said girls my age usually don't like these and I said I know she will like it. I didn't buy anything else until a couple years ago. I was too nervous.

[Brandi17]

For me I believe it was a pack of panties, followed a few months leggings that I would wear in my room when I was alone.

[Lily88]

I think some tights when I was a kid but can?t remember the details! When I was 19 bought a pair of purple ballet flats off the shelf...bought cash because I was panicked about showing my card with my name on...got to the till and couldn?t find the cash...got very flustered and paid on card then got home and found they didn?t even fit! Needless to say I?ve got (a bit) better at shopping now!

[Christina89]

When I was 21 I bought some bras and panties as well as some yoga pants from Lane Bryant online. I was so nervous it wouldn't arrive on time and my mother who knew, but didn't approve would find it. Thankfully they came after she left for work and I spent the rest of the day wearing them knowing that a weight was lifted off my shoulders.

[JennasPanties]

I had been wanting a cute little black sheer thong with a pink bow in front and thigh high stockings for several years. Not sure how it even became that but it had to be my first purchase. Bought everything in person, not realizing what a feat I had just completed. Ran home, shaved my legs for the first time and tried everything on. I was about 22.

[Sally Paradise]

I bought some panties from Soma. I?m married so I assume they saw my ring and figured I was buying for my wife. The big takeaway from the experience for me is that sales staff generally don?t care who is buying, as long as it helps their daily sales. I buy women?s clothes pretty frequently in person while in drab and have ever since that first time.

[ClairFlair]

Soma, is remarkably friendly as a store policy. I shop there all the time (platinum member). They let me try on in either drab or fab mode.

[Rachel19]

Hi
The first thing i pruchased (online) was a bra,panties and suspenders,naturally the bra didn`t fit,but quickly learnt.I did this because my sister was getting suspicious.Now a few years later i go out fully dressed and made up and purchase what i want from lingerie departments and nobody looks at me twice

[Crissy 107]

I bought some panties from Soma. I?m married so I assume they saw my ring and figured I was buying for my wife.
I doubt that, SA’s especially ones who have been around can read us like a book. You went to the right store to shop but beleive me they figured they were for you.

[Sally Paradise]

Could be. It was my first time so maybe I was a bit naive. These days I think it?s pretty obvious when I?m shopping that it?s for me and no one really seems to care.

[Michelle1955]

At 64 do not remember the 1st purchase but the one that stands out was in the mid 1970’s and placed an order at Sears back then it was by phone. I was at college and decided I needed my first set of forms back then they were foam and c cup, order a full body brief, a few more panties.

I picked up the order at Sears. Was a thrill to have my 1st foam forms and 1st full body brief.

[Jeanettew]

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

[Jane G]

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.

[bobbi1957]

for me it was a green dress from a charity shop a female friend was with me and held it up to me to see if it fit . that was an amazing day

[manemami]

I have purchased bra panty set for myself

[Stevie Lane]

In my late teens, when I had a few weeks wages under my belt from my first job, I went a bit mad. It was approaching Christmas and I thought that that was a good excuse to be buying clothes for my imaginary girlfriend. So off I went to my local shopping centre and bought a short black n white pleated tartan skirt, a black party dress and a red one, two sets of bra/panties/suspenders (one practical and one sexy), black hold-ups and a few pairs of skimpy knickers and finally a pair of shoes. All from different shops. The only person that gave me funny looks, that I noticed, was a young girl (of about 8 who was with her mum) who starred at me in a shocked and bemused way as I browsed through various thongs and g-strings. So there I was walking down the high street on my way to the bus stop with all these bags like some Sloane Ranger. To anyone that knew me, this would have seemed quite extraordinary behaviour as I was possibly the shyest person to ever walk the Earth. But buying all these girls clothes didn't seem to faze me at all. I enjoyed it and felt quite confident and natural doing it. I felt far more relaxed than when buying guy clothes. It was a good Christmas.

[Genni]

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.

[Katiedreams]

Stevie.

Christmas is great time for shopping.

Just by whatever you desire. It is all for presents.

- - - Updated - - -

First item was cheap red bodysuit, around 12-15 years a go.

Top bad it was 4 inches too short. :)

That was one-time purchase till recently.

[susan54]

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.

[Allison Chaynes]

Panties, in college. I was still super nervous about buying anything, so I went to a part of town where no one wpuld know me. I think it was a Big Lots.

[cpt2669]

It was a one piece swimsuit. Can't remember what it looked like. I bought it when self check out was a new thing. I remember being nervous as hell. When I got back in the car I looked in the mirror and my ears and neck were red like a sunburn.

[Cdsissymtl]

The first time I bought a merry widow, garters, panties, stockings. It was for Valentine?s Day. it was easier to tell the clerk that all that sexy lingerie was for my wife.
I still remember being so nervous, and the clerk telling me at the end of the purchase, after she did the ?gift packaging? that my wife was very lucky!:o

[krissy]

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:daydreaming:

[Fullerton]

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.

[joanna4]

I was around 17 this was about 10 years ago, I bought a pair of used leather knee high boots with stiletto heels from a thrift store. Lady/owner treated me very nicely at the register. Years later when I got had a large wardrobe, I came back fully dressed and donated them back to the same owner.

[Ressie]

It was around 1984, I was traveling the US with a band so I didn't have to worry about running into anyone I knew while shopping. I picked up a bra and panty set at Penneys IIRC and I also bought a men's flannel shirt in order to be less conspicuous. I wish I still had that bra/panty set. It was hot! Can't remember what town it was, but it was probably in Iowa?

[dtride]

I brought a pair of high heels, it was very exciting, after that is started to get easier to buy clothes

[Alex1967]

Some polyester knickers - bought with other shopping from the supermarket. Really nice pink with glitter bits and Wonder Woman in them

[candykowal]

I was 16 and with my first paycheck, I went to Goldblatts drygoods store as I did with my Mother many times.
I looked around the juniors section and spotted these pretty Easter dresses in pastel colors.
They came with lace gloves in matching colors and were lined in a satin fabric.
And there it was...size12 beautiful powder blue, this is so exciting!
I skipped with dress in hand to the nylon area for two pairs of Leggs (pantyhose)...they came in a egg shaped containers.
No big deal paying for purchases for girls stuff as I was with Mom many times in this department.
I did get a curious look from the cashier, this 16 yrs old long hair buying a Easter dress, she asked me something and I just said yes and nodded.
I was totally in the pink fog, paid cash for my purchase, got a special handled hanging bag (surprise!) and couldn't wait to get home!
I was a little loose in the hips but I filled the darts with the cups of the longline....It looked so fancy...looking in the mirror I thought, is that me?
Still wish I had that dress, wore it many time as Mom would allow me to dress up when Dad was away from work.

[VivianNewkirk]

I'm a late bloomer and didn't start dressing or shopping for dresses until I was an adult. My first women's clothing purchase was a set of lace panties in various colors. That was online, so not much of a challenge. The first thing I bought for Vivian out in the real world was some costume jewelry plus a pretty summer straw hat (which was on sale and totally an impulse buy). By that time I was comfortable with the idea of shopping for women's things and neither I nor the shop clerk lady batted an eyelash over it.

[Peggie Lee]

The first women?s outerwear ( except for bra?s) was 2 women?s blazers black and green because they fit better than a man?s. I wore them for several years and no one ever noticed.

[Patience]

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.

[Michelle_G]

I was probably in my late teens when I bought my first item of ladies clothing. It was a black ribbed knit leotard. There was a blue sports bra type top that went on first and when the bottom leotard part went on the shoulder straps went over that. The leotard part was very low cut down to just above my navel and had high cut leg openings. I also bought some tights to go with it but unfortunately never had the legwarmers. Hey, it was the '80s. :)

[Alana Westenra]

Oh I had a boring as hell office job in my early 20s where I spent hours looking at hosiery on eBay, building lists and then finally getting some black sheer thigh-highs shipped. I was SO THRILLED when they arrived I tore through the packaging and jammed them on only to be confronted with the reality that 'One-Size Fits-All' for women absolutely did NOT apply to tall athletic male frames :doh::doh::doh:!! They had runs almost immediately but the rush of even buying them was still totally worth it! Years later and much internet purchase-savviness accumulated, I'm totally spoiled by the number of resources for good quality women's clothes and CD-specific pieces that I have access to. If I had any real gumption, I'd have become a seamstress... maybe someday!

[Cheryl T]

My very first purchase was a pair of sheer black pantyhose.
It was so nerve wracking. First standing there reading the package trying to decide what size to buy, then trying to decide what style. Lastly actually presenting it to the cashier and having to pay for it.

[Rayleen]

I remember going to zellers to bye panties. was nervous at the cashier . the clerk lady said that will look good on you and she looked pissed.

I found thrift stores had more choice and less worry of bad service .

[DTelia]

Wife sewed a skirt for me....that was the first thing I wore as well

[susanmichelle]

The first item I ever bought was a Brook all swead leather dress size 7 zip up in the rear with holes cut out in the upper sleeves and straps above. It was a beautiful dress and actually the first time I got caught as it had to be zipped on and off by a friend they where there when I put it on but not there when it came to removing it. There was no way possible for me to reach the zipper and was stuck until someone freed me as it was like a glove fit. Tight but still a perfect fit. Oh to have the figure and that dress again. It was also about 4 inches above the knee and I had a pair of black velvet 4 inch heels to match it.

[Crissy 107]

I remember going to zellers to bye panties. was nervous at the cashier . the clerk lady said that will look good on you and she looked pissed.

This happened to me the first time I bought nail polish but the cashier just smiled after she said it and so did I.

[jasmine1995]

my experience seems a bit different from many of yours. i have lived a girl pretty much since i was 12 and that same year i spent allowance i saved up on a couple of really pretty floral sundresses, a pair of shorts and top, underwear and some cute sandals. i went in dressed a girl already with my big sister and didn't have any issues. this was 13 years ago (i'm 25) and i live in a fairly large, progressive city so maybe it would have been different elsewhere but there's a reason sephora boys are a thing so maybe times have changed?

[Staci]

Mine was a pair of nylon bikini panties in a pink color with a little lace on the front. I was 18.

[Gia]

I clearly remember. It was a bit more than a year ago. I did not have the courage to buy any sort of female clothes in person. Thank God my wife helps me now and we always pretend it is for her ( even if sometimes the difference in size is quite evident).
Anyway the first article was a set composed of a white padded bra and white g string. I had ordered everything online and collected at the shop. I was so nervous and excited at the same time😅. I was 25.

[dtride]

My first item was a pair of high heels, It was exciting and scary at the same time, The sales girl was very nice and made me feel comfortable, I will never forget, now the internet makes it fun and easy,I was 18

[Karen RHT]

The first purchase of female clothing I made for myself was a pair of nylon stockings. It really wasn't a big deal as I had already been buying them for my mom and the SA's knew me by name. It did get interesting a year or so later when I needed longer stockings and started buying different sizes.


Karen

[Suranne]

What was the first thing I bought? A grey skirt (C&A). How did it go? Badly, but things rapidly improved from there.

[Sissy_Michelle]

Patience,

It was a skirt. I was about fourteen or fifteen when my mom finally caught me in her clothes. She took me down to Goodwill and told me to try on some skirts to find one that fits. Once we found one she liked we went to the counter and she told me to buy it. She made me wear it on the way home and for the rest of the day. When she saw how relaxed and comfortable I was in the skirt she gave me a training bra, and panties to wear with it. Later then next day she wanted to have a talk with me and I told her how I felt about wearing girl clothes. We made a deal that only when we?re at home alone or I was alone I could dress however I liked.

@?}?-
Michelle

[KatieV]

A lovely summery pair of black sandals with stacked heels. How else could I get out of the house? Everything else I appropriated from my mother's and sister's closet.

[Solange]

The first article of female clothing I purchased was pantyhose. The biggest stress was deciding on size. After what seemed a long period of confusion, I chose a pair and bought them. All in all, pretty dull.

[praderas]

It was over twenty-five years ago.
I was staying at a Marriott Hotel near Washington DC, and I went to a mall, that was walking distance from my hotel. In the mall there was a Victoria Secret shop, where I found a nice garter belt, with panties and stockings. I remember that my mouth went dry, as I asked a girl in the shop for help, finding something "for my girlfriend". I also remember that the girl that helped me at one point me gave me "the look", as if it was so obvious that it was for me and not for a girlfriend.

[ronny0]

It has been so long ago, I can't honestly remember. I would guess it was Legg's Pantyhose in the plastic egg.
Would also say it had to be at the grocery store. Ya know run out to the grocery store for pantyhose.
But I would be so nervous thinking to myself did I buy enough 'other' items so it doesn't look like the pantyhose was all I really wanted "needed" ;-)

[DianaW]

My first purchase was a little black dress. Because every girl has to have one. Right? I love it!

[rian]

mine was very interesting ....i was almost 16 years old ,,walking down a street full of stores ...something caught my eyes ,,a lingerie store where he placed a label for sale to all items concerning bras , panties ,,,,Yet I was drawn into the store and remembered that I spent a long time deliberately folding and shoosing my favorite ones till I left the store with dozens of sexy panties and half dozen of bras ,,,,the problem was were to hide all these ? that was another story

[Jacke]

Late bloomer here. I was mid forties and was in charge of a charity tag sale. I was alone the night before and on a whim picked out several items. Paid for them that night and took them home. A nightgown, a couple of dresses and some bandeau tops. I actually never did more than try them on.
In my sixties, I talked to my wife about wanting to dress for a special party. I had done research on sizes and had a pretty good guess for myself. I went to Alibaba (prices I could afford) and ordered a maroon dress with lace top, body briefer, thigh highs and 3" black heels. My wife suggested block heels rather than stiletto. Smart lady. I also ordered a matching dress for her. Being overseas, this company takes a long time to deliver. While waiting, my wife suggested we go to Walmart and buy me a bra. I was nervous when we started looking for the right size, but before we found it, I was feeling almost at ease. On the way out, she stopped at a panty display and picked out a maroon pair for me. We then went across the street to Goodwill and found one dress the right size. Not the best looking thing, but it is comfortable. The dress and all eventually arrived and fit pretty well, though a bit shorter than expected. Unfortunately, the party never came about before the Covid shut-in.

[TillyCambiare]

My first job was working in London a short walk from SoHo. After walking over a couple of times, I plucked up the courage to go into one of the shops there. After a quick browse I grabbed something in my favourite colour. A matching bra and panty. Took them to the counter to purchase and remember the SA saying "You know these are different sizes?". I just acknowledged, paid and hurried back into the anonymity of the street.

Bonus first time: That was nearly 20 years ago, further purchases had been made online.
More recently after laying dormant for a while I have returned to the CD world, and plucked up the courage to go buy something in person. I had gone to the shops early on a weekday. Went in my target shop, browsed around the lingerie section, grabbed another Bra and Panty set. Then spent ages looking for the hosiery section and then searching through for some stockings. They didn't have what I wanted so i gave up and paid for the set. Friendly GG SA didn't bat an eyelid.
I then crossed over to another store and looked through the hosiery section. Again no stockings but at least a pair of hold ups. I grabbed them and headed to the tills. Again nice, friendly GG not phased at all. Both purchases made in cash, both my heart pounding in my chest.

Tilly

[Just Dana]

The first item I bought was a pair of Keds tennis shoes. This was probably 20 years ago or so. I was at a Target, if I remember correctly, and bought them on impulse. It was close to Halloween. I had a story in place by the time I got through with the rest of my shopping and checked out. Nothing untoward happened, but I'm sure I was shaking like a leaf. :) I imagine most of the Americans on the board are familiar with Keds. They're a simple, canvas tennis shoe. They were very popular with the girls I knew in high school, so had always held a place of importance for my femme side.

Since then, I think a couple of pairs of hose at drugstores were the only in-person purchases. My only proper "shopping trip" was with a GG friend a few years ago. We went to a huge thrift store and I went a bit overboard. Luckily, she was nearly the same size as me, so it wasn't too obvious what was going on - or so I told myself.

Dana

[Alice Torn]

Mail ordered pantyhose At age 51, I bought my first dress at a thrift store.

[KimH]

I think my first purchase was a pair of sun dresses when I was around 20. I remember being very nervous in the store but intentionally taking my time to make sure I got the ones that we just right.

Like many others I also had a terribly lame story in case I was confronted but as I know now to be generally the case, the clerk really didn't care.

I also remember rushing home, putting the blue one on immediately and spending all night in it.

[Natasha.k]

I bought a pretty blue bikini when I was 18. I just had to have it. I used wet sand in balloons to make breasts. I wore it every chance I could. I felt great wearing it..