What was the first item of women's clothing you bought for yr self?

[Krystina]

American Eagle Mary Jane pump from Payless

I own these shoes or some iteration of them. My first items were panties, then stockings. Shoes and dresses came roughly 15 years later

[Amy07]

Pantyhose, Leggs, in suntan then black. Years later I'd get cool shoes and dresses.
Pre-internet was tough.

[tanya_cd]

Black 6" stilettos. Oh yeah ;)

[CarolBrown]

First and only clothing I bought (so far) was a black 36c bra, black panties and a black slip from BHS many years ago, these have long since been purged, due to me trying to walk away from my inner girl...

[AngelaKelly<3]

I bought a skirt/blouse combo. Pretty simple, but I'm a simple gal ;)

[Heatherose]

First item was panties, but my wife bought them. I first bought a redhead wig around Halloween.

[CourtneyJamieson]

I started with my Mom's wig and dresses. Progressed to my SO lingerie and dresses. When I finally decided to establish my own wardrobe I started it out with a black garter belt, panties, bra, and silk stockings from Frederick's of Hollywood. I made sure I checked the mail first everyday until my package arrived. Of course I then immediately followed it up with black pumps and had to then order a brunette wig. This was all back in the mid '90s. Not alot has changed.

[Jayne]

Black silky suspender and panties with pair black stockings, then a pair of black sandals to wear with them.
Also very nervous I was 18 in a ladies underwear shop in Sheffield.
I have never looked back :)

[brenda_s]

Why, pantyhose of course! Easy to purchase and give that instant femininity to the legs (at least).

[jjacobson]

Panties and lovely silk pantyhose :D

[Bruce64]

A Black spandex and nylon panty by Warner, I still remember that, was the best underwear I had ever wear.

[Steve]

Hot pink panties

[Tina Davis]

Pantyhose for me.

[Steve]

After actually thinking about this on, the first thing i bought wasnt actuall panties but a steel boned corset. I bought it because i have a back problem and from time to time i need something that locks my back in place. This is the only thing that does the job, plus give me a nice femme figure and a 24" waist when laced really tight

[Jenn_8B]

My first item would have been panties closely followed by pantyhose.

[gabyklein]

My first buy was a pair of high heel shoes.

[Jackie27]

The first thing I ever bought myself was a pair of silver shiny stockings when I was about 13.

[Belladdresser]

I feel really guilty about it, but I stole a cheerleader uniform when I was in high school. It was tight, but I squeezed into it. I would stare at myself in the mirror, jumping and spinning all afternoon. I was sad when I got too big for it.

[Genni]

The first I bought was a red bodysuit and matching tights. It was lost to a purge after I began dating my wife-to-be. Purges are terrible events lol. I bought a similar pink leotard and contrasting blue tights some years later that I still have and trot out on occasion.

[Lorileah]

I feel really guilty about it, but I stole a cheerleader uniform when I was in high school. It was tight, but I squeezed into it. I would stare at myself in the mirror, jumping and spinning all afternoon. I was sad when I got too big for it.
so you didn't buy it (as the OP asked) and sounds like you were too big when you took it. I am just imagining the cheerleader who was out hundreds of dollars

[Allison Chaynes]

I am certain it was panties but I can't remember details.

[laurenp245]

A denim skirt, loved that thing!

<3 Lauren

[Marjory]

A pair of red t-strap flats, 1958, heels came about three years later.

[Andrea2656]

42D beige microfiber bra. This was before I had breast forms and I liked the fact that I got some shape from the microfiber. Now I much prefer unlined bras.

[DEANNA57]

Thigh high an heels I'd ask ready been given the out fit

[CallmeAlice]

Panties from Walmart

[binair10]

My first item were a full white slip from Tesco`s in 1967. Then nothing until the 80s. Now, I am out every tuesday shopping. Bra`s last week at BHS, panties from TJHughes tomorrow. All in male mode. Past caring what the SAs say or think.

Julie.

[Kiersten]

Mine was a black full slip from Kmart.

[Gina Torres]

Bought on the line. Pink bikini top and silver leopard mini skirt.

Bought in person. A teal lace chemise in my favorite store... Wally Mart. :D

[Megan Nicole]

Panty hose! Finally got the nerve when I was in college to buy a pair of Leggs Sheer Energy at K-Mart. A girl I was dating had a pair and I thought they felt so nice. Found out it was pretty easy to do, so bought several other pair and styles thereafter. My big haul was when I had just graduated college and had my first job. I sent in an order to JC Penny and scored multiple pairs of hose, bras, slips, panties, shoes, etc. all in one swipe. It was heaven!

Meg

[tommi]

Wonderbra in AA cup my wife was even with me she made me purge and slammed me back into the back of the closet
I loved that bra

[AmyB]

Matching bra & panties, the sales girl looked at me funny when she asked me if she could help me. So I said they were a prank birthday present for a friend.

In hindsight, I should have just said, yes, I am a cd, can I go try these on

[threeheavenshigh]

Soft satiny panties!

[Adriana]

A pair of nude sheer to waist pantyhose. Also, picked up a pair of patent red and black 4 inch high heels....ahhhh the memories.

[renae.lake]

For me, lacy "Joe Boxer" panties from K-mart that were too big, and a push-up bra that was too small. I'm still a little surprised I was able to work up the nerve to go in there. These days I much prefer to buy lingerie online; I'm still working on getting the sizing thing right, though.

[Annette_boy]

A pale blue baby doll nightie set from Woolworths, I loved it.

Hugs Annette

[Jessicae]

Thigh high stockings at a convenience store. I was scared to death, but the sales clerk didn't say a word. Had to drive 1/2 the way across town to do it.

[JessiFoxx]

I was too shy to buy panties, I was only 12 after all. My first purchase was a pair of very girly Jordache jeans.

[shortskirt87]

A pair of hoop earrings. I had already had them pierced when I was around 12 (cool skater kid times lol) and I would dress up in my moms clothes while she wasn't home. I'd often try on her earrings, but if anything was missing, she would know. I remember riding my bike to Walmart which wasn't very far away and buying some big hoop earrings. I absolutely loved them! I have no idea what happened to those now lol.

[Matterhorn]

L'eggs pantyhose from a supermarket. I have definitely upgraded since then!

[shawnsheila]

I pair of nylons from a corner grocery/liquor store I worked in when I was 14. I remember fibbing to my boss and telling him it was for my mom. I think it was 1990 at the time

[paintmepink]

Shawnshiela, you are hooottt.

first item was makeup. Prior boss was working, and she seemed taciturn and shocked at this.

[nikkiwindsor]

A long-sleeve, navy blue gymnast leotard...it hugged me in all the right places!

[Dee-anna]

mine was sheer black tights , panties from kmart & hi cut bikini from surf shop when i back packed Australia as a 21yo

[wanda66]

Black bra and matching hi cut panties

[Rosemary+]

A pair of pantyhose when I was about 13 y/o and I'd wear them to bed each night

[Melissa B]

Satin panties, then on to stocking, then bras. I love them all.

[StephanyT]

A white lace bra, so far my favorite!!!:)

[Raychel]

Honestly I have no idea. That was a very long time ago. If I had to guess I would say pantyhose.

[gabriella1964]

I bought my first pair of shoes by myself....waited till nobody was looking then tried them on only to have a bigger woman come by well i had them on.....oh well i lived...lol

[Cd_scarlett]

No doubt it was panties. But heels are more memorable. As soon as I discovered a size that fit it was done for me. the ultimate piece of feminine clothing.

[TracyUK]

For me it was a matching bra, panties and half slip when I was 17 from a shop next the office I worked in.

[Abbey11]

For me it was shoes, followed by more shoes, that's when I had my moment of inspiration and my life improved.......I needed to buy a dress and that's exactly what I did. That was a fantastic day xx

[MonctonGirl]

The first one that bought NEW in a STORE was a pair of jeans.
But online I suppose it was a pair of boots or breast forms.

[iTz Janet]

My FAVORITE clothing: Leggings!!!! OMG I love how they fit on me!

[Samantha981]

nylon satin panties from Victoria Secret. then more panties. Started with bikini's moved on to thongs. Now some of both

[Alice-n-wonderland]

For me it would be pantyhose, then one thing lead to another.

[AshleyJames]

Panties from Wal-Mart.

Yup same here, well actually a few pairs of thongs to be exact. Figured if I was going to do it and get some, I might as well pick up a few. And I still have them today.

[JaniceP]

A Pink Garter Panty when I was 12.

I then went to a stockings shop (this was 1961--No Big Box Stores then) and told the pretty Sales Girl that I was buying them for my sister, I was very nervous so I think she believed me.
I remember asking for seamless, size 11 long, the stocking then all came with Reinforced heel & toe.
Like a bolt from the Blue, I found the nearest restroom (Boys, by the way), went into a stall, took off my boy undies and socks. Donned my pretty Garter Panty and smoothed my nylons up my legs and attached them to the garters.

[GenevieveF]

I bought a pair of 4 inch, peep toe black heels with ankle strap, long gone in a purge.

[Georgette_USA]

Janice
Mine is similar. In the Chicago suburbs, about 12, went to a WT Grant in a neighboring town. Bought a pair of patterned tights/hose. Did wait till I got home and snuck them in thou.
Didn't have to borrow mothers stockings. I had managed to get a pair of girls flats also from somewhere else. Looked like any other teen at the time. Started to feel like I was one of the girls finally.

[Diversity]

It was either panties or a bra for me. My first dress was bought on-line.
Di

[Eva Skarlatova]

Tights! If I should try again - tights! My last bought item - tights! :)))) I could buy tight just to store and to enjoy :) Some kind of fetish....

[karen inside]

shoes!! a pair or heels that fit perfectly!

[LacieMarie]

I bought a full set from matching bra and panties and a cute blouse and skirt and open toed black 4 in heels.

[Milly1410]

A pair of pumps, a top, a skirt and of course, a bra and a slip

[RylieM]

A unfortunately wrong cupped bra (corrected my mistake) and a thong.

[HollyGreene]

Panties.
I found it really easy because for some time I had often bought underwear for my then girlfriend as birthday and Christmas gifts.
We wore the same size, so it was easy to buy an extra pair for myself, and it was fun having matching pairs, too.

[CherylFlint]

Full fashioned seamed Cuban Heel nylons.

[karen inside]

"I bought my first pair of shoes by myself....waited till nobody was looking then tried them on only to have a bigger woman come by well i had them on.....oh well i lived...lol" :gabiiella1964

Oh god.. thats too funny!!! (sorry, opened a bottle of riesling for myself after painting my toenails-good thing it was after)

[rebecca_ns]

Black satin pencil skirt at sears when 1 was 12. Funny thing is, I still have it.

[Annamarie B]

After wearing lots of my Mom's stuff it was time to finally buy some of my own. That ended up being pantyhose, something which Mom didn't have, and something still somewhat new at the time. I still remember shuddering with pure delight as the sensations of wearing them flooded over me. I also remember that it took a little bit of time to make sure that the back seam was lined up with my back seam!

[PattyT]

White female sneakers which I bought through catalog sales over the phone and had sent by mail, general delivery. These sneakers were the rage at that time. The first pair didn't fit, as I had no idea of female sizes. The second pair fit. I had always been interested in female attire and constanly browsed asnd collected catalogs and adds about female clothing, but had never bought any. I worked my way up through female sleeping wear and then to other items.

[~Katelyn~]

It was a pair of stockings for

[Lilly 40C]

Pantyhose. A week later panties and a month after that a bra.

[CONSUELO]

A very pretty black half slip from a small independent lingerie store. Those stores don't exist any more, or at least very few do. I wish they were still around and I wish I had kept that half slip. I still have some clothing that I bought a long time ago and hardly wear. When I come across them it is such pleasure as the associated memories come flooding back.

[Stephanie47]

I have to agree with Consuelo. When I sort through my lingerie it brings back some fond memories. I fondly recall a business trip to Vancouver, WA that was for six days/five nights. I went out before my trip and bought two floor length nightgowns. One was a white gown with spaghetti straps. The other was a red sleeveless floor length gown. It was in October. I was able to sit around in the evening watching the World Series and the presidential debates. I still have both gowns. On a trip to Aberden, Washington back in 1979 I did find one of those lingerie shops owned and operated by two young women. I still have the Vanity Fair camisole and half slip in rose pink. That's one way to start a lingerie collection that numbers over four hundred slips.

[Dana44]

For me it was stockings. I still love them. Then it was panties, a skirt and a bra.

[Krististeph]

Way too many year ago.

Not counting mail order...

A white printed boat neck leotard and pink tights- ala 80's Jazzercise outfit. 1986 or so. It was a cute outfit. Never wore it as much as I should have.

[lisa_vin]

Cinnamon-colored Legg's pantyhose with reinforced toe! I loved looking down at my toes and seeing the darkened, reinforced area that cemented the fact that I was wearing pantyhose! :battingeyelashes:

[lyndsayalexis]

Panties and panthyhose a year later bras and high heels

[rachelatshop]

I was in my early 30's. I was window shopping to kill time while on a business trip, when I saw in window set of patterned tights and leotard. They were just like the ones that I had first become fasinated with being worn by my high school crushes. And just had to buy a pair.

[lauren21403]

Bra and pantyhose, I was 22.

[Emma 1973]

Bra and panties for me, then it all kinda snowballed :)

[Mykaa]

seems if memory serves me, bustier with garters panties and stockings, of course I had to have the pumps as well.

[ChristinaMarie50]

I bought a really nice dress, light pink. I wore it to death!

[Danielle001]

I was 16 and at the grocery store picking up a few things. There was an aisle with nylons and tights and I just couldn't resist. I quickly grabbed a pair of white tights off the shelf and threw them in the cart. I got home super excited to try them on, but soon discovered that in my hastiness, I actually bought little girls tights. I was barely able to pull them up past my knees! Oh well, you live, you learn!

[ZelenaCD]

Panties! Well, I bought Stay-ups and a sexy satin chemise also♥



ZelenaCD

[MissVirginia-Mae]

A playtex "I cant believe its a girdle" girdle and a support bra.
Still love remembering my early days :love:

[Sonyla]

I bought a very nice silk maxi dress the first time.

[Amalie]

Panties is where it started, then came the nighties, stockings and cheap wigs.. then the hunger kicked in (it's never enough).

Although this was mail orders, my first in store was pantyhose.

[Geraldine1947]

First item of lingerie I bought was a pushup brassiere from Playtex, many years ago. Apart, of course, from my weekly shop for stockings and tights. Once I started buying I was hooked. I always love, and can't resist, a nice lacy full slip.xxx

[1263kimberly]

Panties and panthyhose then more clothes and makeup and wig

[Leohose]

Danskin leotard matching tights
Extra pair tights
Cap leotards

[Lucey]

Found that ordering through the mail was as easy as opening a Montgomery Ward catalog and finding the women's clothing section when I was a teen. My first order was some panties and not long after a night gown.

It was sad to see the day that Montgomery Ward first stopped it's catalog business and then closed the outlet doors. We use to have some great departments stores in the area, Zayre's, The Fair, Bradlee's to name a few. And now all there is left is Walmart. :sad:

As Bob Dylan sang, The Times They Are A-Changin.

[Jess6887]

The first item I brought well I brought more then one thing haha. I Brought a long pink satin nightie and a short blue satin nightie with a bra and panties, I then went to another store and got stockings a wig and the next day brought breast forms. I sleept in that stuff every night was amazing

[Half-CD]

First thing I bought was a pair of tights. So exhilarating!

[suit]

I used to fill out catalog order sheets, but there was no way I could have made the order, paid for it ( when your 12 ~14 seemed like $ 60.00 worth of girdles would be soooooo great!) and picked an order of girdles with out help and or getting caught . I had to get my licence, borrow a truck ,get some cash be for I finally bought a couple of "firm girdles"and I was soo curious I bought 2 that sounded like they would be great from a downtown foundation shop . I think i burned them the night following trying them on , they were for the totaly blown out tummy's and were more like wicker baskets with satin trim ,than anything I ever expected any one to tolerate . a week? a month ? later i ordered stuff from sears. that stuff might have had a month be for 2nd purge burn. But they were much softer and friendly to sleep in .

[1263kimberly]

pair of stocking and top and skirt

[Seana Summer]

My first purchase was a pair of Leggs Silken Mist pantyhose, size Q. They were dark brown I think the color name was mahogany? They were a little too small, and I was quite a bit smaller then myself, but they were not making size Q+ yet, at least not that I knew of.

I remember how nervous I was as I stood there at the rack studying the size chart and hoping the biggest size was big enough!

Until then I was wearing my sisters cloths

[JaniceP]

Good for you. I find this is the hardest item for me to buy.

[Devone]

Two push-up bra's 38C and a pair of black sexy panties. Devone

[LIKETODRESS2]

THe first ting i bought was a pair of panties and a bra

[gabyespinotv]

red panties and a bra, wich was actually a 34C and it was huge

[soha]

I bought a thongs, mostly of time I wore under my pants
I pleased by wearing them.

[uwho1976]

very first thing I bought in store for myself were silky stay ups

[Mindy Fey]

Black bali brief panty in the mail thru amazon when in I was in college. Was nervous it would arrive when I was in class and roommate would figure out what it was.

[Laura28]

Bra and Panties at a store was so nerverous felt everyone in the store new it was for me i was about 18 or 19.

[Karine]

The first item I bought was a pair of wedge sandals. I was really nervous in the store and I said that i have to disguise for a party (I really don't think the SA buy it). I really liked to try them on and walk with them.

[kkaye]

I bought shoes, shoes and then more shoes then my dresses out numbered my day to day work clothes. The only thing that has stopped me is that, I dress my s.o. in my favorite things.

[colector381]

for me it was just recent a black 'wet look' tube skirt it said fau leather but I have my doubts

[Sister Rachel]

I bought a pair of tights for my mum, then just had to try them on ... and kept them until my step-mother found them in my coat pocket :(

But the first thing I actually bought for ME ( mail order) was a skirt, wide loose calf-length poly-cotton, big flowers on black design :)

[marlacd]

Hmm, my first was so long ago.What sticks in my mind is a white bra & matching panties. Early in my dressing career, I just couldn't get brave enough to buy anything myself. Getting married is when I got brave. My ex couldn't find nice looking bras for herself. I did, I learned to ignore others, in my search for her. Then it just didn't bother me.

[ThereseW]

Panties at Target, on sale five for $20, Gilligan and OMalley brand. The next day I went back and bought 5 more!

[Fiona123]

5 pack full cut (I'm a big girl) cotton panties. I'm wearing a pair now.

[CCDTanya42]

This is a good one -- Hard to differentiate between things i bought for me and things i bought for GF that were for me. Making her be the naughty girl i wanted to be.

I bought stripper heels for gf in size 6 but shortly after worked up the nerve to buy size 11s for me. Think that was first stuff

[PrivateXDresser]

Panties. I especially love Jockey's No Panty Line bikini. They are better than any underwear I've ever worn!

[Virginia1983]

I dressed in my mothers clothes and makeup. The first cross dressing things I bought was a red lycra dress from a fetish store in town and women's cigarettes - Eve 120s.

[Anjana]

red padded bra, panties and a nightgown

[Alexa CD]

Does a wig count? The first thing I bought myself was a long brown straight wig, so that I could see what I looked like with long hair and know what it might feel like. I had always wanted one. My first actual pieces of clothing are two pairs of knee high socks, one in grey and the other in black, I really like the look and feel of them. After that I bought a really cool grey crop top and a black skater style skirt. All that stuff makes for a pretty nice outfit on it's own even.

[Tabitha_Sinn]

A pair of wine colored high heels :-)

That was 24 years ago!

[Ina Girdle]

The first thing I bought in person was a girdle at a Sears store when I was about 20. I walked up and down the main pathway going through the "Intimates" department until there appeared to be no one in the firm foundations area, so in I went. As I fumbled through the display rack of Sear's brand, boxed, long leg panty girdles trying to locate the largest size, a sales lady came up and asked if she could help me....I managed to blurt out a "No thank you, I just found what I was looking for." and grabbed the biggest girdle I had located up to that point. I felt like my face was on fire and glowing bright red, as I placed the cash in her hand at the counter and thanked her. My heart was pounding as I headed for the door. When I got home I managed to proudly SQUEEZE into my new purchase, If I only had a few more minutes of browsing I am sure I would have found a better fitting one.

Ina

[Tabitha_Sinn]

I felt like my face was on fire and glowing bright red, as I placed the cash in her hand at the counter and thanked her. My heart was pounding as I headed for the door.

Ina, I felt *exactly* the same as you the first time I walked through and purchased from the intimates department! Now days, I don't even know what I was so embarrassed about. It doesn't phase me anymore. The sales people usually just assume I am purchasing items for a girlfriend or wife.

Although I once had a sales person laugh at my purchase of panties and nair. She said I was a "good boyfriend". I just smiled and said thank you :-)

[LisaJ1]

A pair of heels and still have them.I was 16 when this happened

[budlinda2]

Stockings,Then a french maids outfit. I wore it to work on Halloween and won first prize for best costume of 100.00...shock the hell out of me LOL!

[ZenladyCD5]

Had to be a pair of tights. I don't even remember the color or the brand.

[starydziad]

pantyhose in local shop

[ronda]

Victoria Secrets bra and panties back in the 70s

[TSKimberly]

Random costumes at a porn store. As for real clothes, was able to get some black jeans, white top, black vest and stuff. Winter clothes basically.

[Jessica S]

3 pair of panties from Sears. SA gave me a panty card with 3 punches on it and I think the fifth one you either got a discount or free.

[MissVirginia-Mae]

An all-in-one girdle from Stuarts department stores

[CONSUELO]

An amazingly popular thread. Yet not surprising considering how emotional and important that first approach to buying your own things. I still remember the face of the young SA who helped me purchase that cute black half-slip with the stunning lace. She really was not sure if it was for me or someone else.

[Desiree2bababe]

I'm sure it had to be the Farrah Fawcett wig I fell in love with, then it was a baby blue silk cowl necked dress, heels, and hose. Probably swiped my sisters bra. God I felt like a million dollars in that wig and dress.

[Amanda7]

A lace Garter belt (black) and black back seamed stockings!

[~Darla~]

Panties was the first item I bought alone.

[Jodi M]

Mail order from Sears. A long leg panty girdle and a training bra as I was rather young and had no boobies.

[Kelly63]

It was pantyhose , I bought them with the premise they were for my wife. I wrote the details on a note and asked the sales lady to help.

[Rita Leigh]

The first two items I purchased as a teenage were silky pastel baby dolls nighties with full cut panties. I took them on a three week vacation with other young people and dressed whenever I had a chance...it was heavenly.

[aliceharvey]

Panties from zellars i was so nervous i almost didnt go through with it

[jacques]

hi,
a pair of red Mary Quant tights
luv J

[dana digs sweaters]

A white softly padded bra and a white cotton bikini cut panty at age 12 from Kmart. In October under the guise of Halloween ;-)

[Piora]

Black garter belt, black panties, black stockings.

[yidnah87]

It was about 4 years ago when I bought a pack of Fruit of the Loom hi-cut bikini briefs. I've since moved on to more interesting styles.

[gabyespinotv]

red bra and panty set!

[lemon_meringue_tie]

A pair of daisy duke-esque shorts, lol.

[TheHiddenMe]

A good colored top from the discount racks about 12 or 13 years ago.

[NancySue]

Thi Highs.....Hanes Silk Reflections...Barely There. The sales lady was very helpful. I think she sensed who these were for. (smile) I came back a week later and bought Hanes Silk Reflections pantyhose. The same sales lady was there. I almost left, but as we know the "urge" is strong. After paying for them, she asked if there was anything else she could show me. By then I knew "she knew". So I asked her to show me a bra and panties. There was no one around. Then...surprise, she asked me if I'd like to try the bra on. I stuttered...well, I think it will fit OK. She said if it didn't fit, I'd have to return it...so I said OK. She took me to a changing room. Just as I got my shirt off, there was a knock on the door. She said she had something to show me. She brought in 4 other bras she thought I'd like...a padded bra. a push-up bra, and two lacy black underwires. I started to put the push up bra on and struggled a little. She offered to help. I was in heaven. I bought all four bras, three pairs of Vanity Fair panties more Thi Highs. Couldn't wait to get home.

[Janine cd]

Many years ago I bought a baby blue nylon night gown with lace trim at the neck and hem. It was the most heavenly purchase at the time.

[susmitha]

It was a bra - panties set along with a negligee.

[Daryl]

Been so long ago. Was either panties or panty hose.

[Davina4587]

Along with so many others it was a lingerie set.

think i was about 18 and it was a white bra matching panties and suspender belt and white stockings

[crossdlalam]

I brought cup bra.....and lot many panties

[mickynylons]

My first item was a pair of cantrece pantyhose that I bought...saying that my sister sent me in to get them because there was no place to park ;)

[Samantha54]

A leotard and tights to sleep in. I was probably 14 years old.

[Emma or Darren]

A pair of brown faux leather leggings
Emma xx

[Joan58]

Over 35 years ago I bought my first pair of thigh high stockings, Sheer white and they felt so sexy on my legs

[Rain Kensing]

A pair of heeled boots from Target that I fell in love with when I saw a friend wearing them back in when I was a senior in high school. A few months later I wore them to school during our last week. Ask mom if I could wear a pair of her jeans and she said she yes. I got a lot of complaints on them. I still have them and they fit. :)

[realdesired]

Red lingerie

[JamieG]

I was 23 and living in an apartment on my own for the first time. So, I ordered a black fishnet catsuit from an Adam and Eve catalog. I ordered a white lace long sleeve catsuit from the same catalog shortly thereafter. The first thing I bought in a brick and mortar store was a leotard and tights from a Halloween shop. Unfortunately, I purged all of this when I married my wife 8 years later.

[MissTee]

That was many years ago, and it was a nylon (faux silk) nightie. I was so nervous. Back then all shopping was bricks and mortar or mailorder. Didn't dare mailorder for fear the postman might out me. Inside the store, I think I circled the women's department thirty or more times before I worked up the courage to wade into it. Once in, I found the cutest pink and lace adorned nightie decorated around the neck with flowers (yep, I still remember.).

To cover up my tracks, I took the nightie off the rack and went immediately to gift wrapping and had it wrapped. Bought a Mother's Day card, too, since it was only a week or so away. I think I floated out of the store with my purchase, knowing I had fooled everyone into believing it was a gift for my wife and not really for me. Oh, and I had my very first, never-before-worn, my size, my taste, pink nightie.

[Elizabeth G]

I had to think about this for a while but I finally remembered - I was about 14 or so and it was a purple leotard that I bought for "my sister" at a flea market. That was almost 40 years ago.

Beth

[Dana44]

I had to think back and it was panty hose that i bought in my younger years for my fist purchase. LOL I like thigh highs now and have 1 pair of panty hose.

[Jeny_rj]

Pushup Bra.... from Walmart!!!!

[Melissa McLachlan]

A white bra, I had no idea how sizing worked at the time and it was little tight

[barbara gordon]

in the late 80"s i would buy bras and panties for my high school girlfriend. I really would give them to her . ,but I used to always try them on first befor wrapping them up .

Sometimes just to play she would dress me in her underwear . It was very light and not so often . She never really knew that I loved to dress nor how serious of a passion it was for me .
Eventually , around 1990 or so , the "WONDER BRA" showed up in stores and it was awesome! I had to have one for myself !!.
I bought one for her and secretly bought one for me . Funny is that she rarely wore hers . I wore mine every chance i could!

[Julogden]

Pantyhose and panties. Being 6'5" tall, I had no idea as the where to get any other women's garments that might fit, and I was underdressing only at that time anyway.This was in 1969 and things were a lot different than today.

[Janine cd]

I remember walking into a K-Mart store in the early 1970's and buying a blue nightie and a pair of matching blue sandals. I felt as if heaven had opened up for me. Soon after, I returned to buy a wig , panties and a matching bra.

[giana4u]

Pantyhose in a supermarket along with groceries I didn't really need.

[CatchQueen]

The root of all evil: pantyhose

[Lilly 40C]

A red lace bra and panty set.

[Sephone]

Black Dress and high heels. :)

[wanda66]

A pink nightgown and panties to match.

[Matterhorn]

L'eggs pantyhose in the grocery store. I liked them so much I went back a few days later for several more pairs

[SarahBJackson]

A little over 4 years ago, I went into a shoe store for brown shoes. The mens shoes are in the same aisle as the size 13 womens. I picked up a pair of black pumps, put them on, and bought them immedately and forgot about the ugly brown mens shoes. I wore them in the car all the way home, a one hour drive.

[kathy chelan]

when I was a teen I would sneak into my sister's closet, when no one else was home, and try on her shoes. I also made a point to always know where she kept her current bathing suit, also a pink leotard she usually had.
I was briefly engaged to a girl about the time of my college graduation and could wear a pair of her high heel (wedge) sandles. I could wear most of my first wife's things. When we separated, I was very desperate and worked up the nerve to go to a department store at a Houston mall and my first-ever purchases were a very nice sexy two-tone brown swimsuit and pair of kitten heel whte peep-toe pumps. But the shoes turned out to be too narrow and too long so I returned them. A few years into my second marriage my first purchase was a pair of black ballet flats at Walmart and later that year a pair of 2-inch black heel pumps at a resale shop. The clerk's assistant who was bagging things asked me if they were for me and of course I said no they were for my wife. Those began a small stash of things I kept hidden which were later found by the wife and all tossed out angrily. Later a second stash was also discovered and she tossed those things out also. A few years later she also left me. I Have been freely indulging my crossdressing urges since. My most enjoyable purchase was one time at a payless on west Westheimer, I found a hair of 3-inch white heels with decorative flowers that were a size 10 which were just the right fit, and the only pair left, marked $22.oo, discounted to only $9.oo. I was all in drab, but I pranced all around the store in them to the delight of myself and the two young sales girls as well; it was mid afternoon, on about a Thursday or Friday, approximately 7 years ago.

[ztockingz]

Black stockings and a garterbelt.

[lovetobedani]

It was definitely pantyhose mixed in with all my other groceries at the supermarket.

[Rachel Anne]

I got a whole wardrobe...ordered out of the Sears catalog. Probably $200 worth of stuff. I was finally living alone and wanted to fill the closet.

The next time I upgraded to Penny's

[Imeni]

Umm, the first thing I bought using someone else's credit card? It was some sort of chemise and some discount brief style panties from... sears? But the first thing I actually went into a place to buy for myself after much panic and stress? A wedding dress. And it didnt even fit. It was just cheap. And thats been about it. Most of the stuff ive gotten from my bigger lady friends have been materinaty clothes, a few bridesmaid dresses that havent fit, a wig i never use and a few cheaper nighties i got on sale that i use when i want to feel pretty. Its horrible. I'm bad at being a crossdresser. I think i might need to give my card back in at the desk. D:

[Michelle123]

It was definitely pantyhose mixed in with all my other groceries at the supermarket.


Ha Ha. I bet many us us did that one...

[Kendra Sue]

A panty girdle from Woolworths

[krissy]

Mine was a matching pink bra and panty set with garter belt a nice lacy black full slip and a nice soft silk dress and hose. i dont fit them any more but i still own them lol

[Jane277]

Mine was a black satin teddy, and heels

[ellbee]

I have no idea to be honest

Ditto! :o

[Terrafora]

According to Amazon my first purchase of girls clothes was a woman's hoodie, jeggings (which were slightly big) and a waist cincher which I got a medium instead of a small by mistake.

The next order was crotch-less lace underwear and false eye lashes (Which I've not really had the chance to wear yet)

[misschris]

Fun thread! 3 pair of panty hose bought through the mail in 1985 from and ad in the Sunday paper. I had just rented my first apartment alone.

[BecomingMichelle]

Actually bought I can't remember. Choice items I purged and miss terribly yes. Now when I was 13 I shoplifted a pink babydoll nightie from a dollar store. It was the first item I felt was mine.

[Tracy Irving]

I bought a few pair of panties that I wore out and (sadly) had to let go of in order to downsize.

[susancheerleader]

A skirt. :) (from eBay)

[DIANEF]

Bought a nice bodyshaper and stockings from Debenhams (a major UK retailer), thing is, lots of other guys were in there buying stuff aswell which made it a little easier for me. Otherwise use mail order.

[Lana Mae]

Panties! But unlike Laurana I bought them in K Mart!! And like Michelle3 a 5pack of size 6 which was too small!! If panties is too boring, next was a Cortland long leg pantygirdle with lacy cuffs on the legs!! Then breast forms from Janet's Closet and a pair of bras from K Mart!! Then a long lacy sleeved midi dress from Blairs!! And then... Hugs Lana Mae

[nikinylons]

Legg's Sheer Energy Pantyhose and still wear them today, except now I order them in bulk at a discount price from their website. Nothing beats a great pair of Legg's :)

[dolovewell]

January 4, 2006

Bra at Victoria's Secret at a mall in Abilene, TX

I still remember the exact date because it was the same night Texas won the Rose Bowl against USC.

[itsgonnabepretty]

Panty hose from the local Rite Aid.

[brenda girl]

a dress from sears

[sara66]

A black lace one piece body shaper for Bali & a pair of black dkny pantyhose.
I was scared to death. I hardly could get out what I wanted to the SA.
Sara :heehee:

[jennifer0918]

A pair of black pumps that were a size too small for me.Bought them in my guy size 12 and it's 14 in womans

[Kathie Pantyhose]

a pair of Legg's pantyhose. I put them on in the car while in the parking lot in the middle of the day and went to work with them on under my pants.

[krissy]

For me it was a green silk dress some seamed hose and a pink garter belt and pink lace panties and pink bra came as a set

[redtea]

it was 3 pairs of black panties at once.

1- being a brief
2- being a hipster with a nice band of fabric around the hips
3- being a thong

None of these were too great though, they were good at the start but they didn't stand the test of time once i discovered the bikini cut style.

[CartoonistChick]

It was a Kathy Ireland black ribbed turtleneck sweater and I do believe also an Icelandic-looking winter scarf...

[RainbowDash]

I bought a Princess Peach outfit from Super Smash Brothers. Using my own measurements, I ordered a cosplay outfit from China. It took 3 weeks to a month, but when I put it on, I loved the way it looked on me, and I was almost wishing that I were her.

[Sometimes Chelsea]

A 3 pack of panties. Turned out to be the wrong size. :sad: All that internal freaking out went to waste.

[Maria Darkspace]

Caress 401 4" heels, a dip dyed tank mini dress (charcoal), and 38C breast forms. Pink nail polish the following day.

[Lucy23]

Almost three years ago I bought a black bra, panties and garter belt set together with stockings. And a day later I bought my first high heels to complete the look :) Although I tried to keep my composure by telling myself that it was almost Christmas so it would look like I was buying a present, deep inside I wanted to back out and run for the hills.

[JustJoni]

My first was pantyhose (off-black Hanes Silk Reflections). For an actual garment, I bought a grey and black sweater dress from the Goodwill store. When I dressed I was always about a decade behind due to shopping in thrift stores.

[fun4metoo2004]

A high waist girdle, and pantyhose.

[ImJessicaNow]

Black thong and a camo gstring. I wore both to class in highschool but was worried Id be outed when bending over

[Steph54]

Nightgown

[Becky Blue]

A beautiful green thin knitted top, I bought it for my first night out so I would have it as a memory.

[leotard fan]

a blue leotard...

[Della]

A white, satin sting bikini with pink hearts. It was Valentines day--a good alibi for a boy of 18.

[Charlotte1971]

A short grey sweater dress from goodwill.

[GenevieveF]

A pair of 4 inch, black open toe heels with an ankle strap. Sad to say I purged them years ago.

[RaquelAtwell]

A yellow and white stripped bikini. Was a tad small though.

[Mark B]

same day I bought a pair of black strapped 4" heels. Then went next door and bought two pairs of hose (one pantyhose and one pair of stockings) and then went to the next store and bought 3 pairs of thong panties.

[Abbey11]

4inch stiletto's and like others they did get purged ☹️

[Christina D]

I just started dressing a couple of weeks ago by using my girlfriend's clothes. We're fairly close in height and weight, so most of them fit me fine, but of course I want clothes that I can call my own. Also, she's more of a blouse and pants kind of woman, which just doesn't make me feel feminine enough. So, yesterday I went to Target to buy my first dresses.

Admittedly, I went a bit overboard. I bought 6 dresses totaling about $160. I doubt I'll keep them all though because I was too scared to ask for a dressing room, so I grabbed 2 mediums, 2 larges, and 2 extra larges having no idea what sizes mean when it comes to dresses, let alone knowing what size I am! I tried them on when I got home and still don't know what looks good on me. :-(

[Allison2006]

I believe mine was a pair of No Nonsense black sheer to waist pantyhose and it was when I was probably 19 or 20. Up until then I had only worn my mom's or my sisters.

[BaliGirl]

A black wirefree bra and forms from The Breastform Store.

[Aunt Kelly]

OMG, too long ago to remember for certain, but I think it was a girdle. I think they were referred to as "sport girdles" or something like that. Brief-style, with garters.

[Jeanettew]

I bought Some 6" Black High Heels

[robbieatbest]

Black satin French knickers - I still have them but they aren't very comfortable (they still fit though).
Robbie

[Beverley Sims]

An elasticised waist skirt,when I was sixteen.

I still have it and it still fits.

Just. :-)

[Nora_H]

A colorful maxi skirt. Lol

[Satin Girl]

A pair of black pantyhose and black lace panties, said it was for my girlfriend but had none at the time. Many years ago so no Internet shopping around then, would have been a lot less scary :)

[ElvenPrincess]

Since teenager, I always bought ballet Tshirts and used them normally as a boy. As I danced at the time, it matched perfectly.
I also had some yoga pants.
It was a perfect way to enhance my inner female self. :)

[Julie MA]

I started with skimpy mens underwear, and transitioned to womens underwear. They never felt right until I bought a gaff. Love the look, but it can get annoying eventually.

Went to a CD store, Glamour Boutique, in Auburn MA and bought the whole package, pocket bra, forms, garter (love them), thigh highs, dress, wig, etc. I buy shoes at Payless because I can slip in, try them on when no one is looking, and sneak out.

[MissEllie]

The first items I bought were a black suspender belt with matching seamed stockings, a 5" pair of high heels, a lacy brief and a red dress. Safe to say, I felt amazing wearing the outfit :lovestruck:

Ellie xx

[Erin77]

Red satin ruffle bum panties.. loved them!! Wish I still had them but that was soooo long ago. :).

[Nonya Biznis]

I don't get much out of the clothing and dressing unless another woman has worn it, so I "borrow' or have clothes donated. Slips and pantyhose sometimes are hard to 'borrow' or have donated so I had to buy them at times.

- - - Updated - - -

oh yea. SHOES! Size 12! had to buy shoes!!!

[DarLynn]

For me it was a black leotard tights and sheer wrap skirt leg Warmers and ballet slippers

[pinkcapri]

Right after I got my first pay cheque in my first job after college, went straight to a lingerie store and bought the most sexy lacey & colorful sets of panties and bra ( I think I bought 3 sets) and ordered a B sized silicone breast form, and my journey of wearing panties and bra started. I have never worn a men's underwear since then, it is now 27 years. At some point I bought few Manties (panties for men) but did not like them as they did not provide that soft & silky, low rise and smooth butt hugging effects that I get from VS panties.

[Judy-Somthing]

As a teen I had a lot of access to women's clothes so I didn't need to buy any.
But if I remember correctly the first thing I bought was my first wig and 40 years later I still have it.
It's the one item that served all the Purges.

[ReallyLauren]

My first thing was a pair of tan high heel sandals.....it was an amazing feeling to have something of my own after being a long time "borrower".

[Jenniferxcd]

A matching bra and panty set

[jami]

leather skirt suit

[gownman]

A short Miss Elaine nightgown

[Dana44]

Stockings were my first thing I remember buying.

[karrin]

vanity fair panties ravissant 15712

[Johninabra]

A bra at J. C. Penny's

[charlotte449]

A short leather skirt and black knee high boots.

[SarahBJackson]

My first item was a pair of knee high nylons. I wore them secretly at a meeting that I had to attend. A couple weeks later, I bought my first pair of heels, the first items that I couldn't hide!

[gownman]

a short Miss Elaine nightgown

[Kathyxd]

A black 36B Wonderbra from Marks & Spencers

[Miss Mandy]

The first item...I was working at Sears in the electronics department. It was right across the aisle from the ladies lingerie department:) One night at closing, as I was leaving for home, I told the manager letting me out that I left something at my register...I walked back and diverted to the lingerie section, pulled a lace all-in-one from the rack and stuffed it down into my pants. I quickly exited right past the store manager with beads of sweat rolling down my face:) I was a teenager at the time and ready. to take chances like that...I had never shoplifted before or since.

The first item I purchased were fishnet stockings from a Frederick's of Hollywood store. I was 18 at the time. The plan was going well until I walked out the door of the store and met my uncle in the mall. He was staring at my paisley pink bag...luckily nothing was ever said!

[GirlyKayla]

I got a 1950s swing dress off Amazon and was so lucky it actually fit me because I guessed my size. (It's the dress in my profile pic)

[StephanieM]

Panties from Walmart is the very first items I bought.

[mona lisa]

Pantyhose.

[Linda Kay Scott]

It was 1972. I Bought a cute blue wet look windbreaker with shiny silver buttons. It looked fabulous with white bell bottoms. I was 12. I used my allowance money.