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

[herhis]

A pair of black boy short panties from jc pennys website.

[Helena93]

The very first women's clothing item I bought were black sheer pantyhose. I remember being very nervous and sweaty, because I didn't want to be 'caught'.

[ShirleyN]

Short navy pleated skirt followed by a long black pencil skirt.

[Sarina Curtis]

Panties of course! After that a pink floral print one piece dress that I could barely get my arms through.

[Diane Taylor]

The first item I ever bought for myself was what I used to refer to as a "Beginner's Kit". nylons, panties, and heels.

[Spiritfox]

It was 2 pairs of panties. I went to a department store, picked theme out when no one was looking, and used self checkout so I didn't have to go to a cashier

[stephenie3756]

It has been so long ago I can't remember. Whatever it was, it was purged a long time ago. I remember ordering the grab bag from Fredericks of Hollywood catalog back in the day....the excitement of opening the package and seeing what beautiful clothes from Fredericks I just received was awesome..

[Swimtran]

I had been stealing stuff for years, but I never found fancy lingerie, which I was really aching for. So at some point, I couldn't take it anymore, so I made up my mind to go to a lingerie store (this was around Christmas, 1995, I'm pretty sure, so online options didn't really exist, and in any case, I didn't dare have mysterious packages shipped to the house I shared with my parents and brother). I pretended it was for my (non-existent) girlfriend. The clerk helped me out, didn't let on whether she knew I was shopping for myself. I picked a white lace teddy and garter belt, and white fishnet stockings.

I had just around that time accepted my crossdressing, and was taking some new and exciting steps. I shaved my legs for this outfit, for the first time, and then had to hide it from my family for weeks. Ironically, I also met a girl who threw herself at me while I still had stubbly legs, and had to hold her off for a few weeks until I could be "presentable" again. I didn't dare reveal my secret. I ended up dating her for a couple of years, and she never found out.

[Robyn2006]

Insane as it now seems, the first femme item I ever bought was a bra from an advertisement on the back of some magazine. Things were so difficult way back when. Good lord!!!

[Brandybea]

Oh My..it was so long ago, but I still remember it. I was to pick up my parents at a train station and got into the town early and did a little shopping. I found a taupe with black lace bustier, panties and stocking set. After buying I immediately found a bathroom and put them on under my drab. What a wonderful memory...picking my parents up...driving them home and being so sexily dressed under!

[mikeb75]

It was on yahoo stores(when Yahoo was a power house back in the late 90s) a blue leather skirt and at the same time I bought a a pair of white heels

[SaraCanonmill]

Technically, a cardigan from Hot Topic that they for whatever reason didn't sell a male version. I consider my first thing to probably be a pair of platform creeper heels though shortly followed by a dress to go with it and a skirt.

[Patrica Gil]

13 years old I bought my first pair of nylons. Pantyhose were not around yet.

[Paula2]

A pair of black heals.. I have been "all in" ever since 👠

[Kendra Sue]

A panty girdle from Woolworths. I was about 14. I always borrowed my mom's playtex rubber panty girdles. Yellow with holes. The smell was exquisite. That was enough to make me excited

- - - Updated - - -

Yes, I have resorted to stealing stuff on clothes lines. Now I own my own stuff.

- - - Updated - - -

I would love to try on dresses but I am too scared to ask. I did try on a pink pair and a red pair of panties in a store and of course I bought them.I tried on a jacklyn smith pantygirdle at kmart. I got so excited I jacked off in the dressing room. Ofcouse I bought it.

- - - Updated - - -

My wife owns a black leaher skirt that excites me from time to time. I would love to go out walking at night while wearing it

[Scarlett398]

I really don't remember it's been so long ago. But I will tell you that the last purchase I made was my all time best ever! Five skater skirts for 24 bucks and that black one with the shear pattern on the bottom of the skirt that all you girls loved is a real knock out! And like I told you girls, it was purchased at Plato's Closet - my favorite consignment shop - and it still had the original $29.99 Forever 21 price tag on it! Personally, I would have paid close to twice that amount for that beautiful skirt. And the four other skater skirts were cute as a button too! You can see all five of them in the Shopping and Fashion area under a thread with my name in the title of the thread. Most of you girls have already seen them and gave me the two thumbs up on them.

But If I had to guess on my very first purchased CD item, I would guess that it was a five inch high heeled pair black Mary Jane style heals - you know the ones with the strap across the top of the foot. Not a tacky pair of Mary Janes but a real sexy pair of them!

Take care girls and have a wonderful week....XOXOXO Scarlett :love:

[Trione]

A pair of butterfly lace panties at Ross's. Then the SO got me a nightie at VS and it was on from there.

[Jeanettew]

It was valentines day so i went into Bras and Things and bought a red Bra and Pantie set, stockings, slip and a corset, the salesperson said lucky wife, i couldnt wait to get home

[terri-joe]

A white sleeveless sundress. Inner wear, full slips. Both online. Just recently a pantyhose from a supermarket. Maybe i am imagining but i think the cashier was having a weird look at me.

[Swish]

Bought hundreds of pairs of pantyhose and panties, and several bras. Started buying skirts and blouses and even a few dresses for myself at Christmas time, when it was most plausible to be shopping for gifts. Had a few askance looks about the sizes especially from the younger sales women but tried to pull it off with confidence and eventually just came not to care as much. Got outright snickered at at a Bali outlet in the States when I was purchasing bulk pantyhose in a large size, by a young clerk who I thought was absolutely beautiful up until that blatant display of callous inner ugliness. First purchase that stands out was a bright red faux wrap silky polyester dress from Sears. Still have and wear it. Delicious. I swear I have developed almost as much of a fetish for purchasing women's clothing for myself as wearing it. It is very exciting and thrilling.

[phlover]

A nice pair of stockings (it was around 40 years ago... hehe). ^^;

[jami]

pantyhose & leather skirt suit

[Tina Post]

Lingerie ..... panties, bra and hose.

[Sami Brown]

I don't remember much about the first under things because it has been so long and online. I do remember the first time I shopped in a store. I bought two skirts from a second hand store. One was short and lacy. The other was longer and more conservative.

The checkout process was so nerve wracking that I almost puked! It was a good first learning experience though. That is when I discovered that most people don't care.

[CDJoyce]

Black bra and pink panties

[gender_blender]

I bought a bikini as my first purchase.

[miki s]

I recently took the big step of buying my first dress and I'm obviously new to this because I can't figure out how to reach behind to zip it up fully.

[Nancy Richards]

My first item was a loose fitting night gown. Felt like a dream that feeling is still as good tonight as that first night.

[helenejo]

A black silk ruffle blouse. It had been displayed in the window so I had to ask the sales assistant where they were on the racks. She showed me and then said "you may need a size 18" so she obviously realised it was for me.
Outwardly my face went red from embarrassment, inwardly I was excited beyond belief :)

[countrygirl]

Bra, panties and pantyhose.

[7ftEmily]

A bra. Ended up buying it a band size to small and bought my second bra and purchase the following day haha.

[Rachelle70]

Thigh Highs! ;)

Rachelle

[VeronicaV]

A pair of drugstore Leggs pantyhose in white when I was 13. I was so scared, but a thrill at the same time.

[droopydog]

A leotard

[Gendersoul16]

In private; a lingerie teddie. In public, a halter top......age 23. Of course I had Jordache tight jeans and Frye boots, could be considered unisex. The halter and styling my hair did it. Oh and lip stick!

[5150 Girl]

Casting aside the cliche of pantyhose, my first real buy was my big floppy denim dress which remains one of my favorites, and navy pumps. The pumps I soon ruined trying to make them black with liquid shoe polish. However they were soon replace with a pair of white pumps, which I liked better anyway.
That dress and the white pumps were the ONLY clothing items drab or fem, in that room (note disclaimer) to survive the house fire I had back in '96.

[wantstocrossdress]

I think this thread needs a poll to tally the replies. A graphic or numbered display would be helpful as well.

Poll (https://goo.gl/4Vffi0)

Results (https://goo.gl/vKjJhc)

276547

[longblood]

I guess it was a one piece swimsuit. First time buying it as a teen was such a thrill

[Stephanielawrence]

Like many others My first item was a pair of pantyhose! Then it was lingerie, I purchased black Merry Widow set with black stockings. Shortly after it was a pair shoes, the rest they say is history (and thousands $$$!)! I love shopping for Stephanie!

[AutumnNC]

I purchased a ugly purple bridesmaids dress.....But I loved it!

[Adelaide]

Panties and a long haired wig. I do NOT need that wig anymore...and hope I never will!!!!

[Amy559]

My first purchase was a satin cami and pj shorts set along with a lace bra and panty set. I still remember the rush I got from buying them! I was in haven

[Sharry]

Those from online shop :)
276730
and they didnt fit. lol

[jennifer0918]

Black pumps

[Nic J]

It woz some silky capri yoga leggings. They feel great & my wife thinks my legs & behind look really good in them :)

[AileenCD]

I bought a nice silk cami at a thrift store, and the same day a nice padded B-cup bra and another lace bra from a department store. I had shopped them on line and went in with a list. I was having trouble finding them, and some ladies who were shopping were very helpful, thinking that I was a clumsy husband sent by his wife. :)

[Sami Brown]

Haha, I have used that clumsy husband ploy before!

Sami

[Kyle20]

I would purchase bras and panties on line. The first store store purchase was a grey maxie skirt and navy blue vee neck top.

[LeannS]

a top and a skirt from Walmart Had my eye on the items for a few days had to wait till I got paid to bring them home ok now they are home where do I keep these fun times a few years ago oh no wait still is I think I need a shed with a loft lol

[Susan Thomas]

I was going through C-130 aircraft commander upgrade training at Little Rock Air Force Base. After working up my courage, I went to the Safeway and purchased a pair of pantyhose. The feeling of slipping on my first pair of nylons was exquisite! Of course, I did feel very guilty.

[MaidMarguerite]

It was a leopard print monokini, in a metallic pink. I got rid of it in a purge I did upon entering college thinking that I would give up the lifestyle...still regret that decision :/

[Jen84oh]

The first items I bought was pantyhose and a thong but the pantyhose were too small

[Costume]

A very 80s looking peach bridesmaid's dress from a charity shop. I couldn't even zip it up properly, and I'm slim. But it was my first foray into the world of all things bridal!

[Alana58]

A pair of pantyhose was the first lingerie, then a pair of heels and finally for clothing, a skirt and blouse.
Here is the skirt277809277809

[Jamie 65]

Skater skirt

[NylonSissy]

ALways had a thing for Pantyhose. Looks Like I am not the only one who had pantyhose on top of the list :)

[Rebecca60]

That's usually the reply I get.

[Angie G]

My first item Pantyhose And I don't even remember what the next item was.:hugs:
Angie

[Seemsman]

First thing was girdle then pantyhose and panties

[NikkiS]

My journey started with believe-it-or-not a simple female-form fitting winter jacket. It was just like an opening in a water dam! And now the whole town is flooding! haha! :-)

[ChanDelle]

A pair of small gold hoop earrings for pierced ears.

[Robbiegirl]

A Baby blue Babbydoll nightie with ruffly bikini panties. I felt ADORABLE wearing it

[kimdl93]

Ah yes, another flashback. Without a doubt, the first purchase was a pair of Legs Queen size sheer support stockings. I put them in the grocery cart and hoped that the clerk wouldn't think much about it. Years later, a clerk in the lingerie section at Dillard's complimented me for knowing the size and color stockings my wife wanted. She had a little grin that suggested she was in on my secret.

come to think of it, I'm surprised that she didn't say something like "your wife must be tall too"

[Iris Tse]

A really really bad wig. I do remember having fun with it though since I had no sense of what I wanted to see in the mirror. Looking back at my pics, i looked scary and awful!!! LOL.

[ginapoodle]

Oh that's easy, Leggs Sheer energy pantyhose...the old style in the actual egg...loved them, they were better back then...

[Amanda Monica]

Ahh, for those of us old enough...Leggs Sheer energy pantyhose in the classic "egg" container. Burned into my 70s childhood memory. Went to the corner (A&P) store to buy a pair for "my mom". No issues since I had actually done so as part of my usual gopher duties previously. But this time they were diverted to yours truly. Must have spent hours trying them on when no one was home.

[prene]

That was so long ago.
I think pantyhose but not sure.

[Christina Page]

I believe it was a pair of crotchless fishnet pantyhose that I bought in college.

[Maria_mtf]

Padded bra in pink, double padded bra in black and blue lace sleeved midi tight dress. From Amazon so technically all arrived at same time

[Susan Thomas]

I was a 1st Lieutenant going through training to pilot the C-130 at Little Rock Air Force Base. I found myself in the Jacksonville, Arkansas Safeway. This was when pantyhose were very popular. I put the pantyhose and a six pack of Dr Pepper in my cart. I thought the Dr Pepper might distract the clerk from my pantyhose purchase. It was scary and exciting at the same time. Thinking about getting drummed out of the Air Force if I were discovered as a crossdresser, but slipping on the nylons was exquisite!

[Whinlatter]

Hold up stockings, from Sainsburys!!

[Tracy Ann]

Pantyhose! One winter I shaved my legs and they got cold. asked wife to borrow a pair and I was hooked. Wife got tired of it after awhile, so I stopped. Now I'm working back in that direction one step at a time.

[Dana44]

Stockings for me. Love them on my legs. Winter time only. LOL

[CD Tammy]

A pair of tights.

[Michellette]

Black lacy panties and leggings. I wore them under boys clothes back then.

[Melissa73]

The 1st thing I purchased was at Target! I wandered the store what seemed like forever! Finally got courage to look at the lady clothes, eager to make a purchase! I bought a thong leotard and tights! Raced home to try it on

[Robyn16]

First thing purchased was online, pantyhose and a skirt

[drEdge]

The first thing was a red bra and some black and pink cheeky panties.... at walmart! And I still love that bra to this day. I was also extremely nervous and lied to the cashier saying they were for my gf :P

[lmildcd]

It was either knee highs, panties, pantyhose or a pair of shoes. I don't remember. The four items that I listed is what I started with.

[Shelly Lynn]

Panties and pantyhose I already had a bra given to me

[Brie84]

My first piece of clothing was a maxi dress from Walmart. Was very scared to venture into the womens section, but got the courage to do so. Picked up the dress and went to the self-check line. Now I have no fear wandering through the womens section.

[Paula Michelle 77]

I believe my first item was either a cute little pink with black trim bra and panty set or some strappy heels. Either way it's fun to dress up occasionally ;)

[xandralovesleather]

Oddly enough, it was a leather skirt!

[suit]

Panties and pantyhose I already had a bra given to me
ooh let's hear the story of who gave you a bra , and did she have you model it for her ?

[SusieSmith]

OMG... was it for me or my wife... just can't remember...

[suit]

:heehee:

now didi any one ever wish they could buy something like this ?279792
Imagine a corset bult in with a zipper to hide the workings! yummy!
speaks to the few fetishes i suffer with, Now just add this key system to the zipper 279793
and laced zipped and locked into your taboo finery....try not to get caught when your hands get sweaty as your SO is due and you find that built in weight reducing rubber corset might have cramped your shoulder s a bit and reaching the key...damb dropped it .... "hi, need help ? ", she asks ...you look really cute, hope you just getting dressed , I love to see how you spend your "personal time" did I mention snug dresses and corsets make picking things up off the floor ..time consuming!
280373280374

[Petra-CD]

My first thing I bought out by myself shopping was a bra from the Deb. I was 18 and very gothic. Black with pink skulls printed and trimmed in frilly lace. I still love the goth look some 15 years later.

[Joanne Rice]

Vanity Fair panties were the first thing. After that, it was everything from wigs to heels

[priyasweet]

Bra and panties from walmart lol. Now I have a small collection from amazon :)

[Luci]

Bra and panties from Walmart

[SaraLin]

Trying to remember that far back (40+ years)...
The first thing I can remember buying was a pink, terrycloth-like fabric, sun dress/ beach cover up type outfit. It had a skirt that came well above the knees and felt *SO* good when I had it on.

It fell victim to the first wife's "she-found-my-stash" purge.

[randilipps]

Hi All,
my first cross purchase was panties from Amazon. I have several panties and Thongs a couple are my favorite but the don't carry them any longer.
I have purchased a bunch of articles from Aliexpress.com Delivery time is long. But the prices are wonderful....

[karenph]

no nonsense pantyhose from the drug store

[susancheerleader]

Hmm. My first piece of women's clothing I bought myself is either a gymnastics leotard or a cheerleader skirt. I don't remember what came first.

[Hicuts]

A Playtex 5 pounds thinner longleg panty girdle.

[Sami Brown]

I may have posted something else earlier, but I forgot about what was truly my first time until this past week. I was in New Orleans on business and decided to go to a lingerie boutique. I bought a peach colored camisole. This was about 1985 or so. At that time I was just curious about what it would feel like, and it was wonderful. I wasn't very serious about crossdressing then, but I had completely forgotten about buying that over 30 years ago.

[Janine cd]

Mine was a baby blue nylon and lace night gown. It was so smooth against my freshly shaved legs. The feeling is still clear in my mind forty years later.

[ricki4678]

Panties. Red crotchless panties. Very sexy. I bought them because of my gay lover. He liked men in female apparel. Here I am many years later with a closet full of female clothing. Oh well, life goes on

By the way I cannot view my profile. Does anyone know why that would be?

[GinaSkirt]

My first item was a skirt. I definitely have a love of skirts very versatile with blouses/shirts, but recently into dresses.

[Ronnica]

Pantyhose, that's where it all started for me.

[Faith Noel]

First thing I bought was a white garter set, complete with hose an. Panties. So long ago now it would be considered vintage. Lol

[Cherylgyno]

Jane. My first was pantyhose. I believe the year was 1971. I was so nervous that the cashier had to help me count my money out. Back then I would like and say that I was shopping for a GG. For the last 25-30 years I have been honest.

[Ashleyrobyn831]

First thing I actually walked into a store and bought was a pair of black patent leather pumps. But the first "clothing" item was a long denim skirt.

[Jessica_Proton]

String bikini Joe boxer satin panties yellow with a smiley face!

[Sandra_Dodds]

Leaving aside the numerous pairs of pantyhose I bought, my first clothing purchase was a lined black pencil skirt. I loved the way the lining would slide and feel over pantyhose covered legs.

[Susan Smokes]

The first thing for me was a pair of leggings and a bra at kmart.

[Keichan]

A pair of suede leather grey ankel boots that I still absolutely love. I wear them in guy mode as well as they are somewhat gender neutral-ish. :)

[Renee36c]

matching panties and bra

[RachelCD4]

A pair of black 5" spiked heels...from there I was hooked

[alesha]

The first item of female clothing I actually owned was a pair of red heels from Payless. I somehow managed to convince my sister to get them for me. I forget what pretense I used but we got them for me. The first thing that I actually bought for myself was a pair of black hose and garter belt. It may have come with panties, I don’t remember. I bought it mail order (I think from a cd place) and had to wait 4-6 weeks for delivery. It came on my birthday and we were going out for dinner. I wanted to stay home and stay in my room so I could try them on but my parents were insistent on going out so I stuffed them down my pants and when we got to the restaurant and I excused myself to go to the bathroom where I put them on. Suffice it to stay, that was probably one of the best birthdays I ever had.

[dressupdallas]

A red dress I bought on Walmart.com.

[xdress408]

The first thing I ever bought was a pair on Leggs pantyhose.

[Venessa_48]

The first items I bought for myself of course pantyhose! That was easy, the first time I bought clothing I used the excuse it was for a Halloween costume party so the SA was really cool and she helped me with everything. She thought I was really into it because I was wearing pantyhose already. I told her I wore them so I could try on shoes with the costume. Little did she know.

V

[josie_S]

Oh god who remembers anymore? LOL

Seriously I'm trying to make my brain remember and I CAN'T...how depressing!

I *do* remember some cute strappy sandals and these cute navy blue baby phat jeans and cute black top that I wore with them! I'm sure that, and a not so great wig, might've been the first full outfit I bought for myself. I was traveling for work and had to get out of the hotel room so I went for a drive and gassed up my rental! I asked the woman behind the counter of she "could tell" and she didn't know what I meant...then I told her and she was so surprised! OMG I was on cloud nine! so of course I went back to the hotel and stayed inside :cry:

[Robin2005]

Panties. Long story as how that ended up and I will post that story up later.

[Megantg]

I bought a babydoll and a bra/thong set, however I saved myself from embarrassment by buying them online!

[Julie Slowinski]

L'eggs Silken Mist Control Top Pantyhose - Off Black. I was 22 and it was a few days after I came out to my girlfriend at the time (the first person ever). It was in a 7-11 and was so scared I almost pissed myself. Got the Indian cashier to put them in a brown paper bag. On the way home they sat in the passenger seat with the awkwardness and excitement of a first date, that is until I had to pull over open the little carton and feel their softness. I had just shaved my legs for the first time the day before, so putting them on for the first time was like a long awaited trip to heaven ...

[Morgan lace]

I wa 17 when I bought my first things.
A Black satin 3 piece set. Bra panties suspenders. From Miss Selfridges
I was so nervous, when the sales assistant (I'd say she was I her mid 30's.) asked me what size, I replied, I don't know what size I am.

It was a very busy Saturday but the sales assistant took me to a changing room and measured me (over my clothes). She then got me the right items and rang it up. She was really helpful and put me at ease.

When I got home, I found 3 extra pairs of panties and a pack of stockings.

[ShoeziQ]

White high heels with an ankle strap. Then I bought a grey dress. Then a black bra and pantie set. Now it's just ridiculous.

[Melissa&Proudofit]

I remember the first thing i bought, that was three pairs of those satin panties, one light blue, one violet and one red pair. The young lady serving looked at me and asked me jokingly, were they for me, where without think i said yes, she went bit red then apologised for asking. She was quite cute, so i never minded anyway.

[MissAmber]

The first thing I bought myself was a pink pair of satin and lace panties from Victoria's Secret before that I just wore my wifes things

[freeindress]

A blue and turquoise sports crop top and matching hot pants.

[Sarah S]

Blue satin panties

[racheldresses]

panties, mini skirt and blouse. All in black. Soon replaced by basque, stockings and panties, again all in black. Next came some heels. Guess the color?! And then a little black dress....hmmm there's a definite theme here.

[Kayliedaskope]

Rachel, maybe your goth side is showing.

[colourmannn]

A bra and girdle from the Sears catalogue

[racheldresses]

Rachel, maybe your goth side is showing.

It took me a while to realize that I could look feminine in colors other than black. Though even today most of my wardrobe is black. I do love black lace.

[Fiona Lindum]

Tights and knickers from Marks and Spencers.

[MsKim2888]

For me its a long black tube dress with black pantyhose.

[DelilahGurl]

Hmm.. that I actually bought for myself?
It would have to be a 3-pack of the prettiest lace panties ever.
Peach, mint green, and navy blue. They fit perfectly and made my butt look awesome!
:)

D

[Ginni]

My first purchase was 3 pairs of pantyhose. I bought them at a department store. The young lady behind the counter was very nice and helpful. It was a very exciting experience, but felt natural.

[pedalgirl]

The first item I ever purchased was a pair of black high heel pumps. Got home dying to wear them only to discover for the first time the difference in mens and womens shoe sizes. I was to embarrassed to take them back and exchange them. So disappointed.

[jamienoir]

I haven't posted in awhile but will do so more.

About 12 yrs old I bought some cheap red designer panthose from Woolworth. From there I justed started buying more stuff. I had a wardrobe in a few months.

[karrin]

a 3 pack from sears no seams antron111 nylon pink, blue and yellow in size #6 ahem! quite a while ago lol they fit quite nice, I liked myself in them especially in pink ;)

[renaej7]

The first thing I bought was a white satin lace bikini at Belks when I was in the 9th grade. I was so nervous, I actually called the store and asked the clerk to put them aside for a gift person. The emotion I felt going there and during the purchase was so overwhelming but I got through it.

[Carrols]

A black Lace Maidenform bra, 34B, and matching panty. I could fill out the bra back than! Now I've had to go bigger in both band and cup!

[2B Natasha]

I bought three items at once. A pair of black stir-up pants with a very pronounced seam in the front ( still love that look BT w ). A package of knee high nylons and a pair of patent leather black sling back flats with a pointy toe. Wore it once I think; freaked out that I would be seen and tossed it all. I was 18 at the time.

[michelleg]

A black and green satin chemise that was sheer on the sides and barely there in the back, after wearing it a couple of times I had to get a pair of heels to wear with it.

[Stephanie43]

Four items at once. Black skirt, pink and black blouse, high heels to match and thigh highs (the ones where a garter belt is not needed).

[ShirleyN]

Not sure if I already said this but it was a long black pencil skirt and then a navy knee-length pleated skirt.

[Charlotte7]

I'll always remember the first thing I bought. It was a grey, front pleated skirt from Littlewoods. I was very nervous when I bought it. I was sure that everyone, not just in the shop, not just in the shopping centre, but every sinsgle person in the whole town was watching and staring as this man bought a skirt. It was a horrid skirt but it was 'my' skirt.

[JaneinFL]

Blue and white polka dot swimdress here.

[binni101]

If I remember correctly, the first clothing I bought were black and tan stockings :)

[Christina89]

The first items I bought myself were 3 pairs of boyshorts panties from Lane Bryant. I was nervous about going into the store, so I ordered them online.

[Nastasha]

First job, first paycheck ... first panties. Gitano panties at Walmart, drove 1 town over and spent half my check. Money well spent IMO.

[Doaranna]

My first items were bought by a gg-gf, so I had no real idea of fashion or sizing ... so I went to a cross dresser boutique in Ft Lauderdale ... with a T-gf and bought the store out! But I always to put on my favorites first every time I dress ... garters and black stockings and the bra with forms. Such a wonderful feeling!

[Kendalli]

Online, Yandys lingerie. A while selection of panties and three different kinds of bras.

[Michelle1955]

Sears catalog order (1975) picked up items at store order desk. panties, bra and foam forms. Took courage to walk intoSears and the order desk.

[suit]

yes! but way safer than having it delivered to your house!
I bought a bunch of stuff from sears long ago , and with in a week i burned the lot
wrong size not what i expected and shame with a dollop of self loathing .
but damb if it was not all was bought again...and then some ...x 10

[Marianne S]

I think what I bought first was a white lacy blouse. It was similar to one I'd seen on a girl I liked and found attractive. I felt nervous going into the store in my mid-teens, but I went through with it.

It's interesting to see how many people made underwear of some kind their first purchase. I imagine it makes a difference whether a CDer starting out young has access to clothing (however secretly) from a mother or sister in their home. I was lucky in that respect. Before ever buying anything, I found I was able to wear my mother's skirts, blouses and dresses--in fact as a slender teen I had to pin her skirts a little tighter to make them fit--and needless to say, I enjoyed wearing all of her underwear as well.

[Metalsissy]

I just recently started buying via Aliexpress. You can get so much for just a few bucks. So when I bought my first clothes it was about 10 items or so, cointaining shoes, stockings, panties, babydoll and 2 sets of formal womens clothing.

For some reason, they always send the packages to a pick-up point. Everytime I went to pick up a package I felt kind of ashamed. One of the employees at the pick-up point is a former classmate and almost every package containes the descreption “womens clothing”.

[Babbs]

BRA !! I go to bed every night wearing my d cup bra filled with my d cup breast forms....I just love bras and boobs, lol

[Jasmine Rose]

The very first item I bought was an emerald green silk camisole. That was from a catalog, and I never had to worry about what anyone else thought of me when ordering.
The first item I bought in a brick and mortar store was a matching black bra and panty set from Victoria's Secret. I remember telling the sales woman there that they were for my girlfriend. I'm sure that she saw right through me. She gave me a very knowing look, and said "you have very nice taste".
I have never bought anything in person and actually indicated in any way that it was for me. However, I have learned to stop offering up information. The less you say, the less chances for the sales clerk to say or think anything about what you are buying.

[JenniferZ]

The first item I bought was pantyhose. That was many years ago and I still love the feel of stockings and pantyhose (among other items).

Jennifer

[ToniG]

Was in the 70s. Shoes and pantyhose. Definitely No internet then. ! Toni G..

[Denise S]

Aqua colored Victoria Secret satin pajama set, I was shaking when I walked out of the store.

[fantasticsix]

A black leotard from the Back To School section of a local superstore when I was about fourteen. It took ages to pluck up the courage to pick of off the rack and take it up to the register. I've loved leotards ever since!

[Monique65]

Back in the 70s I bought a black lace bra and matching panties at Penny's. I told the SA they were for my wife.

[Kimmie WJ]

My first purchase was simply a pair of black tights.

[ricki4678]

crotchless panties

[Emily Barton]

286660

It was this dress! I must have been about... 16, 17? I walked into town, into BHS and over to the dresses. I was so incredibly nervous! I didn't go far into the shop before I saw it - I guessed a size and grabbed one then legged it to the counter. I remember I trod on the bottom of it in my hurry because I was just holding it by the hanger like a doofus!

Anyway, I got it home and hid it away then tried it on that night when everyone was asleep. It fit perfectly and is still my absolute favourite dress. It's been with me a long time! :daydreaming:

[Christinne87]

I bought the whole kit at once, but the first to arrive was some beautiful pointed heels. About 4 inches. I miscalculated the size and was a size too big and made them difficult to walk in.

[Dana44]

It was thigh highs for me. followed by panties. Then a a skirt and a top.

[Aunty_Hazel]

It is a beautiful dress, Emily.

My first purchase was a pencil skirt and a pair of hold ups.
I meant to buy a top too, but I lost my nerve.
(I already had underwear, which I'm embarrassed to admit I had stolen)

[Leslie Mary S]

Weirdly enough, the first thing I bought for myself were a set of size '8' forms, and size '9' forms over the internet. what size I wanted depended on the outfit.
Prior to that, I would get a GG friend to do the buy either at a thrift shop for dresses (never underwear or sleep clothing), or over the counter for underwear or sleep clothing at a Big Box Store. She is a size 38 DD bust. I am a 42 and with the forms a D.
Also I was frequently doing sewing. Making an extra set of Frilly panties just took a bit more time. Also I was making outfits for my wife, two daughters and son.

[Rollermiss]

Wow a lot of you purchased pantyhose as your first item. Does it have to be a new item purchase. Mine was a competition skaters leotard/dress costume I found it at Goodwill. It was actually one of the girls on my competition team at the rinks. We used to car pool to practice. One day her and her mom picked me up. It was right on top of bag of other cloths next to me in the backseat. I asked what's all this stuff for, Her mom said, I am dropping it off at Goodwill. I always loved those costumes and she was about the same size as me. plus being a fox. I waited a week. found it on the rack and bought it.

Kelsey

[Jane G]

Quite forgot I posted this thread. It's been fun catching up on all the recent replies.

Emily that dress is just so you.

[Devi SM]

I dressed as woman when a boy with mom's stuff but then, married I just for accident start wearing my wife's panties, thing, she knew but not this was part of my cding, neither I knew, but lately I began buying my own panties together with my wife's panties, thongs...

[Devi SM]

My first purchase was a pair of pantyhose. I almost hyperventilated when the cashier couldn't scan the code on the package & had to ask for a price check over the PA system!!!
I turned extremely red & I'm certain that she realized the hose were for me. I still get embarrassed when shopping but I think that's part of the thrill.


Your comment made me remember that I began buying lingerie for my wife. It was a specific store on women's lingerie at the downtown in the city in my country. I used to give long explainations to the SA that were always women. Now I realize that I was preparing myself for later when I began purchasing panties for myself so I didn't have all that thrill you experienced...

[Leslie Mary S]

. . . Snip. . .
"However, I have learned to stop offering up information. The less you say, the less chances for the sales clerk to say or think anything about what you are buying."

Very good advise.
My dad taught me; :"The world loves a good listener" At that time I was a young teen and constantly talked and butted in , and interrupted others.

[SarahMarie]

My first purchase was little T-Shirt bra from Kmart My moms where why to big and my sister wasn't old enough to have bras yet. I was about 13 at the time. My mom let me stay in the van while she went grocery shopping I ran into Kmart. I remember right after buying it and hiding it in the Mini Van my mom came out with the groceries and then wanted to run into Kmart real quick to get me a new pair of jeans. As we where checking out I was so nervous that the cashier same one I checked out with was going to tell my mom.

[Drew GB]

I liberated my first bra from the laundry room of my apartment complex. And I think before that I tried some of my mothers stockings which were so thrilling to put on. In fact once in jr high I was home alone on a Saturday so I snuck in and put on a pair of her pantyhose then threw on my jeans and headed into the backyard. While out there one of our new neighbors heard me playing around and decided to introduce herself. I got so nervous as if she could tell what I was wearing under my jeans. But the conversation went on in a normal fashion until she invited me up to her apt to meet her BF. Not to be rude I agreed. I felt so... naughty. Here I was in their apartment and all I could think was how glorious my legs felt.

Having said all that I know I have not properly answered the question of this thread but it was a story I have wanted to tell for a very long time. Really the first thing I bought myself were a pair of 3or4 inch black heels in high school. Purchasing them was not odd as I lived in Hollywood and their were shops on every block running down the boulevard that cater to drag queens and cross dressers. I wonder if they are still there these days.

The heels were for my first Rocky Horror picture show. Which I was going to attend as a Monty Python Lumber Jack. I got the whole outfit, Flannel shirt, Jeans, Plastic Axe, and heels. But sadly when the night came I chickend out and did not wear the heels in front of my friends. 😞

I am pretty sure I still have them. Where is the only question...

[Kiara]

About 25 years ago I bought a nice leather skirt for myself, but my sister found it in my chest of drawers so told her it was a surprise gift for her birthday. Still a little upset that she found it but she had no right to go through my things.

Oh well, live and learn I guess.

[gunta]

Silver earrings, four 2" chains with stars at end in each ear

[krissy]

My first things were a matching pink bra and panty set and a pink slip and a green silk dress i had to wait for two weeks to get out of layway but wow

[jasminemaine]

Panties. Definitely panties.

I vividly remember shopping in DeLand Florida as a young crossdresser, and nervously walking into a department store (can't remember the name), and buying satin panties.

It took years to overcome the nervousness of purchasing clothes. But I have no nervousness anymore.

[Sallee]

I am guessing since it was more years ago than I'll admit. A bra from a discount department store. NO questions from anyone but lotsof embarressment for me. But what a rush
Simple pleasures I love em

[Rebecca60]

I am guessing since it was more years ago than I'll admit. A bra from a discount department store. NO questions from anyone but lotsof embarressment for me. But what a rush
Simple pleasures I love em


My first purchase was a pair of pantyhose. I almost hyperventilated when the cashier couldn't scan the code on the package & had to ask for a price check over the PA system!!!
I turned extremely red & I'm certain that she realized the hose were for me. I still get embarrassed when shopping but I think that's part of the thrill.
I will always be a pantyhose-girl

First item that I purchased for myself was a black stockings and garter belt. The women SA told me to be careful..

[EllenJo]

My first purchase was a pair of panties and some thigh hi stockings. It was years later before I began to fully dress.

Hugs
Ellen Jo

[CatchQueen]

Pantyhose...and they weren't even that special in hindsight...but I got a massive kick out of the whole thing back then.

[CaseyAdams]

This thread really makes my brain throb - where did I get all those clothes!!! First purchase was probably a black pair of tights. First of many, I should say, as it is so hard to find the perfect ones.

[~Renee~]

Under the cover of Christmas, a wrist cuff. Cheap piece, but its my piece and I love how it makes me feel every time I put it on.

[banzini]

Mine was a pair of suntan Calvin Klein pantyhose.

[Deanna11]

I would have to say a bra and leggings online from Sears, my first in store purchase was a cute pair of shoes!

[cdintraining25]

Probably a dress and maybe some cute panties, It's been so long I can hardly remember.

[Jamie390]

It was a blue bathing suit from sears. I'd wear it in our pool after my mom and dad went to bed. It got purged years later when I got married the first time.

[Frannie7]

First thing I bought was a pair of 4" heel sandals. At that time I would wear my wife's clothes but her feet were too small. Eventually, I have bought my own things.

[Juliana817]

When I was about 17-18 I went to Victoris’s Secret around Christmas and after years of narrowing finally got myself a bra, panty, garter set...and of course some stockings.
All black and couldn’t wait to wear them!

[Thumbelina]

The first time I actually bought for myself was in preparation for the first time I went "out." I couldn't be passable under the best of circumstances to I wanted to go with something that could at be least marginally considered "unisex." I opted for a skin tight pair of stretch jeans in bright red, a purple satin top, and a pair of high heeled black boots.

[valerie anne]

A black bra from a charity shop.

The elastic was shot,and it offered no boob support, but my straps were visible under my shirt!

[Asew]

My first crossdressing purchase was a red wig during halloween.

But my first clothing purchase was about a year later. It was a longline bra at a lingerie store. I felt bad lying saying it was a for a girlfriend. And she told me girls my age wouldn't like it. I always wondered if she knew I was buying it for myself. I was planning on buying shoes and a dress or skirt that day but got too nervous after the first store. I haven't purchased anything since.

[ShyLibrarian]

My first crossdressing purchase was a red wig during halloween.

But my first clothing purchase was about a year later. It was a longline bra at a lingerie store. I felt bad lying saying it was a for a girlfriend. And she told me girls my age wouldn't like it. I always wondered if she knew I was buying it for myself. I was planning on buying shoes and a dress or skirt that day but got too nervous after the first store. I haven't purchased anything since.

Delectable, smooth, white camiknickers/camisole panties at the US Navy Exchange in West Ruislip, a NW suburb of London, UK. Had many happy times in them and sometimes wore them over a pair of bikini panties. However, the elastic eventually stretched and I was losing weight so they would (blush) fall down from time to time

[Jemima]

Gosh.....I have thought quite a bit to remember what that was :) I am not 100 percent sure but there is a very high chance it was stockings. I can't remember the brand or color or material though.

[nikinylons]

I've responded to this already but worthy of doing it again for you girls who haven't gone through the entire thread. My first was L'eggs Sheer Energy Suntan and Jet Black control top pantyhose, which I still wear on a daily basis today. Then a teddy and dress at Walmart. Then I found Fredericks of Hollywood for my first wig, 4" pumps, dresses, and long satin gloves. Now I order almost everything from suddenlyfem.com because they make clothes that are designed to fit men's broad shoulders and body structure. Ya, they aren't cheap, but high quality, feel and look great, and easy to work with. Pantyhose are still the core is this girl!

[MissVirginia-Mae]

A full figured bra, control bottom and pantyhose from Jordan Marsh

[JaniceP]

Pretty Pink Garter Panty and RHT Stockings.
I was 12 yrs. old, went to the washroom, took off my boy undies and socks then donned my pretty Girly things.

WHAT A RUSH!!

[Jenn26]

My first purchase was bikini panties from Target. The practical side of me came out. I wasn't sure what style I would like nor the sizing. So I went with plain white panties for my first purchase.

[Joanna447]

A short black leather skirt. :)

[t-girlxsophie]

Full outfit for my first ever time out meeting others like me.red/black floral print shift dress,sparkly cardi and strappy heels.

[Betsy]

Having never crossdressed, I recently went looking to buy some shoes that were attractive, comfortable, light and open. I found that men's shoes tended to be heavy, more closed and unattractive. After extensively looking online and in shoe stores I pretty much gave up on the men's shoe search. I realized that what really was trying to find was men's shoes designed like women's shoes. Feeling pretty uncomfortable I decided to look at some of the women's shoes at my local shoe store. I found and bought a few pair of sandals that I liked a lot and began wearing them. They looked so much nicer than the clunky sandals I had been wearing! Based on this success I next I bought a pair of flats.... then nylons.. and then the panties. I'm hooked!

[Kay J]

I was about 10 went to Ben Franklin 5 and dime bought a pantie girdle. Bet the same wonder what the heck.lol

[Patience]

A skirt from a thrift store. It cost a buck.

I still have it and it's one of my favorites.

[sabrina1955]

It's been a long time, (40yrs??) but I think it was a long nylon nightie, and I used to hide it in my pillow case. Don't know if mum ever found it.
Sabrina.

[Megan Rice]

I bought a pair of black pantyhose size medium tall I was so nervous they were too small and I destroyed them just trying putting them on

[faltenrock]

I really have to think, because I buy so much. I think it's a black floral short dress, in my picture gallerys.

[BrendaPDX]

I think my first purchase was a pair of stockings, the kind that had to match your shoe size.But the first that "did" it for me was a dress with a side zipper, it fit so well, I just stared at myself in the mirror, I just couldn't believe that she was me! Wow blast from the past, Thanks for the memories. Brenda