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

[Jane G]

Mine was silk bra and panty set, from House of Frasor along with a white nylon slip. I was so nervous and bought them as if for my girlfreind. What a fantastic and memorable day that was.

[Elli87]

I bought a babydoll dress and a thong white mesh with little hearts printed all over it. I was in uniform I said it was for my girlfriend, but the sales ladie knew my girlfriend was the same size as me.

[SillyGirl]

Most of my early stuff came from girlfriends. The first thing I bought myself was a pair of 4.5" single sole, black stilettos. They are a classic pump, slightly pointy toe but not too much. I still have them, I still have trouble walking in them. 4" is about my limit for walking naturally, any higher than that and I get that can't straighten the knee fully silly girl walk. Regardless, they're sexy shoes and I love wearing them.

[Jane G]

I bought a babydoll dress and a thong white mesh with little hearts printed all over it. I was in uniform I said it was for my girlfriend, but the sales ladie knew my girlfriend was the same size as me.

You know I think they see straight through the pretence a lot of the time.:eek:

[Ceera]

My first female clothing purchase was two 4-packs of string bikini panties, and later that same week a steel boned under-bust corset, which I took back the very next day and exchanged for a full corset, because the under-bust one gave me way to much 'muffin top'. I didn't have to talk to anyone about the panties, but actually admitted to the SA at the corset shop that the corset was for me, even though I was fully en-drab.

[Melanie 0339]

The first items I brought myself was some white lacy stockings and suspender belt with a pink silk night slip dress. I spent most evenings when I was single wearing these, they made me feel very girly and pretty. xxx

[BLUE ORCHID]

Hi Jane, It must've been over 55yrs. ago I think that it was a bra and a pair of nylons.:daydreaming:

It was at a SS KERSGE 5&10 Store, They were the founder of K-MART.:hugs:

That had to be back in the late 50s' when I was 16.and just started driving.~~~>Orchid ...:)...

[Tracii G]

I have no idea to be honest

[Elli87]

yup It was after that I decided to quit pretending in a place like L.A. or Tel Aviv it's very easy to just go and buy what you like in Drab or Femme. Where I live now oh boy, had an interesting time at sally's hair supply yesterday

[Steph_CD_62]

A matching black bra and panty from Victoria's Secret.
I remember being so nervous and telling the lady that it was for my wife.

[RADER]

A Long line Pantie-girdle. It was super tight and flt great.
Rader

[StacyCD]

A pair of purple pointy-toed stilettos that hurt my feet terribly but looked awesome! The price of looking pretty?!?!

[Samantha2015]

Well, if pantyhose count as clothing that was my first purchase.
But the first true article would have to be the black patent
5" stiletto pointed toe pumps I ordered from Fredericks of Hollywood.
Had them for about 21 years before they fell apart. Of course they were
never worn outside but had many indoor miles on them.

[Cara Lacey]

I had a lot of things I "borrowed" , but the first thing I actually bought was a front closure, 36C bra from Klein's Department Stoe in Blur Island, IL. in 1976.

One sales woman was very helpful, but another just glared at me the whole time.
It was such a rush I went back the next day and bought 2 more bras and matching panties.

[Laurana]

Panties from Wal-Mart.

[Alice_2014_B]

High heels
:)

[Lily Catherine]

A pair of women's skinny jeans, without even hiding that they were for me, before I ever went full girl mode. I still wear such jeans in guy mode; they're awesome.

First ever lingerie proper: 6 pairs of thigh highs, all black, and a tiny white petticoat that fluffs out like a tutu.

[SharonDenise]

I bought while in high school one of those Golden Playtex Magic Controllers that were made of rubber or latex from Marshall Fields. I purged and then I think I bought a second one which I also purged. I came home from college and bought a floor length nylon peignoir which I wore at nights and kept hidden in a drawer. I wore it in from of my future wife who approved and the rest is history.

[Jamie Christopher]

Mine was a pretty matching bra, panty, camisole, half slip and teddy in peach with cream lace from a discount mall near Chicago called "A Cut Above" and still have them... Luxury!

Jamie

[IamWren]

The very first item was a pair of nylon pantyhose that my Gunnery Sgt recommended all of us in our unit (about six of us) wear on our a 15 mile hike the battalion was scheduled to do. He said it would help compress our legs and help with circulation and help prevent blisters.

I don't recall it doing either of those two things. In fact, I think the nylon made my feet itch and gave me a blister.
Maybe he was hazing us. :|

[Maria 60]

The very first thing for me as far as I could remember was a pair of pantyhose from a corner store. The funny part was, not being asked by the Chinese worker but felt like I had to explain I told him I was painting and had to use the pantyhose to strain the paint, he was so nice that he told me to wait and then handed me a bag with about ten pairs of pantyhose telling me that they were from packages that ladies open and don't buy them or from packages that came damaged and he can't sell. I thanked him and had pantyhose for a while. I think about it now and laugh.

[BillieAnneJean]

A pair of silver glitter sequin platform peep toe pumps. With ankle straps.

Then a navy blue velvet long spaghetti strap column dress with rhinestone straps and a matching bolero jacket.

It has all grown logarithmicly since then.

Such Fun!
Billie

[bridget thronton]

Skirt and top

[Peggie Lee]

Pink fuzzy house slippers.

[Gabby6790]

I think the first item might have been a amazing pink pushup bra and thong from VS. Unfortunately, the Thong didn't fit at all and soon lost the bra in a mini-purge. After a couple sizing wrong puchases the ones I will remember are the 5 platforms I bought on ebay that fit perfect. They are amazing but super impractical and then a few week later I nailed my size on my first purchase of skinny jeans at Target. I was so happy they fit and felt great.

[Lily Catherine]

@aBoyNamedSue: while at least banned by certain commanders during basic training, tights are said to help reduce groin abrasions for long marches. Never used them during my mandatory national service though.

I run in legging-like tights rather than pantyhose, they are rather effective as far as compression goes.

[IamWren]

Hi Lillian. I run in legging like tights as well sometimes. I bought them last winter to take a little of the bite away from the cold air.
Also like you I wear girls skinny jeans while in guy mode, too. Again... another thing along with my cotton boy shorts that my wife really likes how they look on me.
So if I'm wearing girls' cotton boy shorts, girls skinny jeans and NineWest girls mid calf boots.... am I cross dressing when I go out? Or am I a guy who just looks better in girls clothes.
I think I may need to rethink my idea that I don't go out in public wearing girl clothes. :)

[AngelaYVR]

A black suspender [garter] belt and stockings. I can still remember the thrill.

[Brandy Mathews]

Jane,
I was the same way. Was at a Victoria Secret store in the mall and was so damn nervous too. Told them that I was buying things for girlfriend. Think that they knew different though.
Probably gave it away by the way that I was looking at things.
Hugs,
Bree :)

[lostinmyworldcd]

Black pantyhose and a blue jean mini skirt ..... I already had access to shoes and bras and tops..... I was a nervous wreck buying the mini skirt from a second hand store .... the pantyhouse wasn't a big deal as I got polish and fake nails in the same purchase . Throw in a few household things with the latter at a brand name drug store and the funny looks aren't as common . Men buy their wives /GF 's stuff quite frequently there .

[Jennie2]

As far as a recall 2 pairs of sexy black thongs, I've still got them however they are a bit tatty now they have been worn a lot.

[pamela7]

i bought myself and my wife to be matching thongs :-)

[Georgina]

It would have been in the seventies, and probably was a full slip which I still have.

[Cassandra*]

It started out with tights. My ex talked me into wearing tights under my pants when we went ice skating. It was a cheep pair from woolworths and eventually it transcended into hitting woman's stores. My next item was panties. Now I'm all in.

[JeanetteX]

Stockings and a garter belt. The stockings were ruined a long time ago but I still have that garter belt somewhere in drawer.

[lynda]

hi my first , was a girdle , from the bra and girdle factory in n J . love peace Lynda

[jami]

My first was pantyhose,and I love them

[Keely]

It would have been a bra and panty set.

[alice clair]

I remember going to K Mart and feeling like every woman in the store was watching me in the lingerie section and trying to figure out my size in panties. I ended up with a size 7 which is what I still wear many years later. Now I go in and get whatever I want and I don't give it another thought. I try on tops and jeans or skirts and even dresses if I want right in the store with no embarrassment at all. But yes my first purchase was panties.

[Angela Marie]

Incredibly self conscious as I walked into a Woolworths (yes i'm aging myself) and bought a pair of red tights. I was about 12 years old so I had to hide them at home.

[Maryesther M.]

A modest 19" A-line miniskirt in navy blue with centre box pleats front & back with scarlet reveals. I discovered then that UK size 16 fits me perfectly. I shaved my legs as I had no tights and enjoyed the buzz.

M.

[geek]

The first items that I purchased that could readily be identified as distinctly female was a few different graphic tees. You can tell because of the cut that they're not mens tee shirts.

[Lacey New]

I bought several pair of nylon Pam panties from Macy's. I was not sure of my size, so I got a couple of size 7 and a couple of size 6 hipsters. Back then, the 7s were too large and the 6s were fine. They were very similar to the current Hanes Her Way nylon panties of today - although I have not seen hipsters in quite a while

[Teresa]

Jane,
I think my first buy was a Charnos matching set of bra, suspender belt, panties and slip all in a laurel green colour and smoke grey stockings. I'd worn suspenders and stocking before belonging to my wife but to have your own that you could put away in your own space was exhilarating !
What spoiled the whole thing was the man hair, it just had to go !

[I Am Paula]

My black patent stilettos.
I bought them in about 1980. I didn't think I was a crossdresser, much less transgender at the time. I just wanted them. I sometimes wore them late at night, thru two marriages to women, whom I was too chickensh*t to come out to. They were an important part of me, and lived in my golf bag LOL!! Those shoes kept me sane as my GD started developing. I didn't know it, but dissonance was building.
Sometime around 1990 I came out as a gung ho crossdresser. Still didn't know transition was in my future, but I knew I was more female than male. Those shoes saw me thru hundreds of visits to the gay neighbourhood, and walked the pride route a few times. The insoles of them fell apart, and I carefully lined them with duct tape. Sure, I had lots of other shoes, but my patent stilettos somehow symbolized my true nature.
In 2012 I made the big, and final decision. I had to transition.
During a closet clean out, I was purging some of my older, somewhat tacky, clothes from my gaybourhood days. I was almost fully transitioned, and very full time. I pulled the black patent stilettos from my closet, looked at them with some nostalgia, and tossed them into the black plastic bag.
I didn't need them any more, but they had been an important part of my life.

[DMichele]

My first purchase of women's clothing was probably around 1971, and as best as I can recall I bought lacy panty(ies), garter belt and stockings. I haven't had a garter belt in a long time, and have been thinking about adding it to my wardrobe.

[Krisi]

Other than a dress from the thrift shop for Halloween many, many years ago, it would be a set of four Ahh Bras from an eBay vendor. My wife wasn't happy with her sports bras and wanted to try Ahh Bras so I ordered her a pack of four. When they came in she said "Are those my new bras?" I said "No, they are addressed to me so they must be mine. I stripped down and put one on in front of her. I suppose that was the beginning of my "coming out" to her.

[CynthiaD]

The first I remember is a pair of black lace panties. There were other things before that, but they were purged and forgotten long ago.

[JeanW]

for me I guess was pantyhose also (way too many years ago) as many have expressed fear and shame top of my feelings then. very long time later (about 6 months ago) 2 panties and my very first ever blouse

[JenniferR771]

I bought a pink prom dress for "Halloween" at a garage sale. Then a cute suit and shoes at Salvation Army, Halloween again. Then...a well-padded Vasserette bra at Big Lots, (34-B). The snoopy lady in line behind me said, "I hope that's not for you!" Boldly, I told her I was a crossdresser and it was indeed for me as we walked out of the store. She asked if I was an entertainer or a singer with a stage act.

[Diane1950]

First it was pantyhose and a nightie, which are the easiest things for a guy to buy, right? I mean, whose SO hasn't asked him to pick up a pair of ph for her? And a lot of men give their ladies lingerie as gifts.

After that there was no stopping me LOL and I'm still buying practically everything in sight.

[~Joanne~]

A pair of cheap, nasty, saggy pantyhose from woolworth's and I believe they were only 99 cents. I was around 16 and taking them up to the lady at the register was terrifying.

[CarlaWestin]

Hi Jane, It must've been over 55yrs. ago I think that it was a bra and a pair of nylons.:daydreaming:

It was at a SS KERSGE 5&10 Store, They were the founder of K-MART.:hugs:

I bought a white longline bra from Montgomery Ward when I was about 18. I'd gone shopping with my mother so often that I just walked up and paid for it saying it was for my mother. When I was much younger, I was fascinated by the pierced earrings at SS Kresge. I would use my $1.00 allowance every Saturday to buy my mom a pair secretly wishing that I had pierced ears..

[JRZSHORE]

A pair of bright yellow nylon bikini panties

[steph_2015]

3 pack of thongs loved them then and still today got to be my favorite undies :)

[abby054]

A pair of L'eggs pantyhose in the right size. They did not survive my first and only purge,

[irene9999]

Bought from a crossdresser shop online:

-pink mini skirt
-white top
-bra
-cheap wig

[ringedjohn]

My first buy was a light-weight pantie girdle. I still remember the thrill of putting it on for the first time.

[Midasgirl]

Two pairs of women's satin pjs, one pink and one green. Had to take a wild guess on the size, but luckily got it right. Have to say, got very nervous going up to the till to pay - was convinced the woman behind the counter would know they were for me. But no reaction.
Then went straight home and turned myself into a girl.

[Robin777]

It has been quite a few years ago, I still remember what I bought. I fell in love with a Vanity Fair camisole and half slip that is in a shade of blue/green. I also bought my first bra that was matching. I still have the camisole and half slip even if they are a size or two too small. I will never get rid of them. I think the bra may be around someplace. Before that it was the wife's hand me downs. That was just the start.

[Kandi Robbins]

On a business trip to San Diego, had an entire afternoon to myself. Found a Penney's and bought a pair of pantyhose, a slip, panties and a bra. All were black and I was just guessing on sizes. As was typical back then, I quickly disposed of all of it after trying them on briefly. What a waste!

[Tammy Lynn Tx]

Too many years ago to be sure, but It was either panty hose or a cute red dress that had a chest bib. I loved that dress and wore it until I gained too much weight

[LadyInRed]

this time around and last, sexy undies :)

[Robin414]

OK, It was a Sun Ice ski jacket, it was a 'womans' jacket but really kinda androgynous...that was in '86 (just before Sun Ice was the supplier for the '88 winter Olympics in Calgary) OMG though, it was sooo cute...and comfy!!!

[sometimes_miss]

I think it was a camisole and tap pants set I ordered through the mail when I got my first dept store credit card. We used to get some little advertisement with each monthly statement; one day an ad came, I just checked off the size, and mailed it back with my check. A couple weeks later, it came. Mint green with white lace trim. Mine all mine. That set off the realization that I could order stuff through the mail without anyone knowing what I was buying. Within a year, I had started dressing in my own girl clothes for the first time, no longer would I be borrowing things from my sister's old discarded last year's castoffs.

[Adriana Moretti]

wow cool question.....i can remember it was this really cute dark blood red flare mini skirt, and bra set made of pvc that had a matching garter belt. I used to love that little stripper outfit xoxo when i bought it i was like...."Do you have a gift box?? "

[Stephanie47]

One evening my wife found me standing in the kitchen in one of her nightgowns. It was a white long peignoir. She asked me why I was wearing it. I told her the truth. I liked the feel of nylon. We went shopping for my own. I cannot remember which one we bought first. It was either a knee length pink peignoir or a black floor length gown. The black gown had no stretch, so it is long gone. So much for losing that physique of a 25 year old. I still have the pink peignoir after 40+ years. Her white nightie is still hanging in the back of the closet. I had actually bought it for her as a present, but, I was not too learned on sizes. It was actually too big for her at the time.

[Jane G]

My black patent stilettos.
I bought them in about 1980. I didn't think I was a crossdresser, much less transgender at the time. I just wanted them. I sometimes wore them late at night, thru two marriages to women, whom I was too chickensh*t to come out to. They were an important part of me, and lived in my golf bag LOL!! Those shoes kept me sane as my GD started developing. I didn't know it, but dissonance was building.
Sometime around 1990 I came out as a gung ho crossdresser. Still didn't know transition was in my future, but I knew I was more female than male. Those shoes saw me thru hundreds of visits to the gay neighbourhood, and walked the pride route a few times. The insoles of them fell apart, and I carefully lined them with duct tape. Sure, I had lots of other shoes, but my patent stilettos somehow symbolized my true nature.
In 2012 I made the big, and final decision. I had to transition.
During a closet clean out, I was purging some of my older, somewhat tacky, clothes from my gaybourhood days. I was almost fully transitioned, and very full time. I pulled the black patent stilettos from my closet, looked at them with some nostalgia, and tossed them into the black plastic bag.
I didn't need them any more, but they had been an important part of my life.

That's such a great round up of how such little things can change our lives. Thanks.:)

[steftoday]

Wow Paula. That was a great little tale... Thanks for sharing it.
With my age, I'm pretty certain it was pantyhose as well.

My, what a tiny egg shaped package started...

[Dana44]

Jane, for me it was nylons, then heels to go with them, then bra and shucks that lead to skirts then blouses then dresses. I purged like four time and wished I never did that. makeup, panties and all of my heels and skirts. Bra's. I was pretty good at that time on dressing and whenever i was alone it was the first thing I would do.
Its funny but I went through an operation when I was forty four back in 96. They had to crack me open and fix my intestines. Bad one... I had extra intestine length and it kinked. Almost passed. But when I finally woke and was able to look at my self. I had on white thigh highs with a frilly top. It took about three weeks and I was able to get up and walk a little each day walking more each day to get back on my feet. I always had on those stockings. So I asked the doctor about it. He said you need to wear them so that blood clots do not come up your leg. I asked how long I need to wear them. A nurse was there also. He looked at me and said, "You can wear them whenever you want." Oh my to hear that...

[joanna4]

It was a pair of boots from a thrift store back in 2008 when I was 17 years old and just got the car to myself. The blonde lady that owned the place was really nice and bagged them for me and gave a me a discount, total was on $8.

[Jilmac]

Mine was a five pack of pastel panties, a pink garter belt, and several pairs of stockings.

[Staci G]

A pair of jade green pantyhose

[Ninna]

Pantyhose of course.

[taylormercedes]

I bought a white waist cinched with built in garters and thigh highs. Sadly it was lost in one of the many purges, but it used to be my favorite thing to wear when I underdressed

[krissy]

For me it was a matching pink bra and panty set with pink garter belt a white full slip and a nice silk green dress WOW! thanks for making me remember LOL:cheer:

[bronwyneve]

Black satin and lace teddy brought from a department store. I was 19 and had no idea about women's sizing and was very tight fitting. I wish I still had it but was disposed of in one of my many purges over the years.

[flatlander_48]

A bodystocking...

DeeAnn

[TrishaTX]

Panties and I loved them....too bad they were caught in one of my first purges...

[Diane Smith]

TBH, I can't remember exactly what the first item might have been. Probably a pair of pantyhose sneaked into the grocery basket. But my first really grown-up shopping experience, when I was 19 or so, was buying a long black skirt and a companion top, white with silver accents, in the formal wear section of a local department store. It was a pretty sophisticated (and expensive) outfit for anyone of my age, but I fell in love with the look on the mannequin. I don't know what the SA thought, but she offered her help and advice while I was picking it out. Nothing was ever said about trying it on, so I had to estimate the size, and actually did just fine. She checked me out without incident -- I think the bill was around $75, in late-'70s money, and I kept that outfit and wore it occasionally for many years, although I never really had a chance to go out to any event where it would have been appropriate.

Also in those early years, there was an outlet store, similar to today's TJ Maxx but not as big or sophisticated, about a 20-minute walk from my house. It was the only place I knew of in those days that had a good stock of women's size 10 shoes, and was entirely self-service, so you could take them directly off the shelf and try them on without anyone offering to help. I bought a lot of heels there in the day, mostly for $10 - $20 or so. I still have and regularly wear one pair of soft pink leather booties from those days.

- Diane

[Sarah Beth]

In a long involved story I won't go into I was given a lot of stuff by someone when I was a teenager which I managed to keep hidden for years until they tore the building down about the time I headed off to college and I only kept a few things and tossed the rest then.

I went into a huge denial phase about that time and it wasn't until about three years later that I made my first purchase ever in a store. This was in 1973 and I was trying to look inconspicuos in the women's department of a large department store when suddenly from behind me came an SA and who asked if she could help me. I told her I was looking for something for my wife (I wasn't married yet at that time but you know how it goes) so she asked me how big she was and described my girl friend who later became my wife and the SA helped me pick out a skirt and top. The skirt was a multicolored geometric pattern and the top was white. The SA got them gift wrapped for me too. I kept these along with the bra panties and slip I had in a bag in the tool box in my pickup for about a year.

[BarbDriscoll]

A nightgown, under the protective camouflage of Christmas shopping season. And I asked for a gift box, of course.

[Alice Torn]

Mail order pantyhose.

[Sweetalex]

A really short denim mini skirt but I was really young and didn't know how women's sizing worked so it was too small. I still loved it wore it a lot!

Panty hose seem to be popular in this thread, for me they are not that exciting. I much proffered dresses, skirts and heels, things that would make me look directly feminine.

Thinking back I have made some awful purchases around that time! Really bad! But I don't regret them D.... Well most of them.

[Angela.Moni]

A really short denim mini skirt but I was really young and didn't know how women's sizing worked so it was too small. I still loved it wore it a lot!

Panty hose seem to be popular in this thread, for me they are not that exciting. I much proffered dresses, skirts and heels, things that would make me look directly feminine.

Thinking back I have made some awful purchases around that time! Really bad! But I don't regret them D.... Well most of them.

Alex, i also bought a micro mini denim skirt. They were ultra popular at the time. I also bought a pair of platform flip flops that were so IN at the time as well. I felt so chick when wearingt hat combo with bright red pedicure, I absolutely loved it. I was 16/17 at the time.

[Birgitta]

For me it was a pair of black pantyhose.

[tifftg]

Leggs Panty Hose and a pair of heels from Payless Shoes

[Randee]

Sears Black long sleeve leotard and black tights.
It was a summer afternoon when the family was going to be gone on vacation and I would have house to myself for the week while I worked a summer job as a college sophomore. I stopped by a Sears store out of my neighborhood on my way home from work and nervously bought my first long sleeve black leotard and matching tights of my own. With notes drawn up like I was on an errand, I muttered to the saleslady something like "I think this is what she wanted" implying that I was buying for someone else like my sister. I can still remember the titillating anticipation every afternoon driving home from work knowing that, at some time that evening, I would be changing into my feminizing garments to lounge around the house in until bedtime. Tried sleeping but the feeling was too new and exciting at the time to truly relax and sleep through the night.

[Joanne108]

When I was a teenager I bought; a bra, panties, stockings, a corset, a cocktail dress and a blonde wig at a discount store about a week before Halloween. The only comment I got from the cashier was good luck with the costume contest.

[AngieStone]

The first thing I bought was Leggs pantyhose in the egg container

[L'eggs n' heels]

Pantyhose, then high heels.

[ashley-fl]

I was 16 and bought a pair of bikini panties that were black and red. They reminded me of a pair my gf had and I wanted some like hers.

[alwayshave]

Well for years I "borrowed" things from my sisters and mom. The first thing I ever bought was pantyhose. The first item that involved and SA was a silk camisole and slip in 1981/2 from Victoria Secret. They were light blue with white lace. I wish I was still that size.

[L'eggs n' heels]

Pantyhose were easy to come by in the 70s when I was a kid, you'd snag 'em from an Aunt or a Cousin.

[Slipstream]

I too was able to get by on mom and sis' stuff in my younger years. I never really lived on my own and my wife has bought for me for the last 30 of our 31 year marriage. One day back in the early 90's I was in a St. Vincent De Paul store by myself looking for other goodies I collected. Of course, I would always take a nonchalant stroll through the ladies section. In the past I had left behind quite a few "to-die-for" items because of my fear of buying myself. On this day, as I approached the nicely organized bin of undergarments sectioned off for bras, panties and girdles, I saw 3 gorgeous black girdles right on top. They must have just been put there. Two were panty and one open bottom. Lacy beauties with satin panels. Right out of the 60's. All in XL. I had to have them no matter what. I'll never forget it, some big biker dude had to get in line right behind me. I survived and still have them. More importantly, it got a lot easier after that.

[AmyVanessa]

Other than panties or bras, it was my real basic pair of black heels. Then it was two camisoles, the type with a built-in bra

[Bobbi46]

A coral pink slip with black lace round the hem, that first thing gently swishing against my legs set me on the road to where I am now, I will always remember that first feeling as I put it on.

[Sandra119]

A pair if white silky panties

[Tania]

So long ago, but I think it was tights.

[Angie G]

HMG I don't even remember it had to be a skirt or hose.:hugs:
Angie

[DeeNile]

I can remember it like it was yesterday. I was fourteen. My parents had divorced so I spent weekends at my dad's house. I rode my bike up to the local Target store on a Saturday afternoon. I must have stalked the lingerie department for an hour or more before I got enough nerve to grab a black bra off the rack. It took even longer to march up to the check out line and pay for it. I was so nervous and just knew the cashier was laughing at me the entire time. I will never forget the adrenaline rush that came from making that purchase and the feeling of triumph over my fears. It may have been a small step, but it was a HUGE victory. During the entire trip, the only excitement was all in my head. I learned that most people are so self absorbed into their own world that they are oblivious to what is happening around them. This was the early nineties, there was no internet (just an information superhighway) and smart phones didn't exist.

Dee

[Leighcdmd]

Shortly after we were married my wife realized that I liked to wear her panties and, together, we bought a three pack of pastel nylon panties at JC Penney.....in my size. That was many years ago, but remember like it was yesterday.

[mechamoose]

For me it was a bunch of skirts from a 'Savers'.

I have been hooked ever since.

- MM

[jenniferinsf]

my first purchase was a yellow sleeveless scooped neck blouse that i could wear with skinny jeans...thrift store near by

[trishacd]

The first thing i bought was thigh highs,panty hose werent out yet.

[BillieJoEllen]

When I finally saved up enough money and found a place to hide stuff I worked up the courage to finally go out to purchase what I wanted to buy. I stopped at a small dime store in a small town and found a bra and girdle(with garters) that I liked. With my idiotic story in hand I went up to the checkout to purchase these items. I was treated decently. I was very frightened before going up to buy those items. Having built up a bit more courage I went to other stores in other cities. I only bought one item in each store that I stopped at. First was nylons, followed by a slip, then a skirt followed by a blouse and then the ultimate and most embarrassing purchase - a pair of panties. There were three women helping me to buy just one pair of panties. I think they were on to me.

[Chloe1955]

For me it was lingerie from one of those specialised lingerie shops, garter belt, French knickers and cami top in white my fave colour, turns out the shop assistant was a friend of my mom lol

[QueenShorty]

A cute white pair of strappy sandals online from Payless. Unfortunately it was a size too big (at the time I thought I needed to buy a size larger).

[Kaze_]

The first I bought for myself... Its been about two years to the month...

Was a pencil skirt.

[Kathi-Anne]

Pantyhose from JC Penneys.

[nicole01r]

I bought a dress with a white top and kayki skirt and 3 in machramee sandals from Montgomery Wards that the model was wearing in the catalogue. When I got them I tore out the page and pretended I looked just like her! NOT😒

[Lacy PJs]

My first purchase was mail order. I think Roamans had a matched set of bra, panties & garter belt. They came in silver or red; I got the silver ones. But soon after that, I was true to my user name & bought a pink nightgown.

Lacy PJs

[amy canada]

I really can't remember exactly, but it was either a one-piece swimsuit, or a pair of pantyhose that I got at the drugstore. I must've been 15 or so.

[Jaime Noel]

Panties and a pretty lace cami

[Bunty]

Sheer black stockings and a black suspender (garter) belt, from Woolworths.

I was in my mid-teens. I loved the look of women in hosiery, and longed to look that way myself. The only way to get these items was to pluck up the courage and buy them. To slip my own legs into stockings was a dream come true.

[Tammie.J.Swenson]

1st female attire :
VS 38DD FULL COVERAGE RED LACE BRA WITH 4 MATCHED PANTIES. A HIPSTER , STRING bikini, G-string and lace top thong, garter belt and black spider Web stocking.

Most Daring purchase my own String Bikini swimsuit and a female Speedo tback swimsuit Yesterday on a dare from SO GGF.

[jacques]

a pair of tights - Pretty Poly sheer tights powder blue.

[lisa_vin]

The first thing I bought for myself was pantyhose, Leggs' Sheer Energy.

[weyburn]

Bra and pantie set then nylons

[Ally 2112]

A black skirt waaay back in the early 80's then nylons

[Joanne Curl]

Like alot of us, my first thing was that pretty plastic egg- Leggs pantyhose. I got up my courage when I discovered no one cares what you buy and bought panty hose that fit, some mascara and some lip stick. I love makeup!

[Quintaseg]

I actually stole one of my wife's saree.

[ashleyjane15]

A black pair of stockings. I love how they feel on my skin. Now that I am out, I'm going to start a wardrobe.

[Katherine L.]

Playtex 18-Hour longline bra.

[Kaz]

Stockings... hold ups... black.. from some department store in Leeds... that night I shaved my legs for the first time and wore them under my jeans when I went out for a drink with a good friend... amazing... I haven't thought about that for a long while... if only he knew!

Hugs
Kaz

[fun4metoo2004]

Pantyhose. That was the start. When I bought that first pair and put them on. Wow! what a feeling.

[immike]

I thoroughly enjoyed going online&ordering a mini skirt,a silk printed bow blouse,a 4pr.package of No Nonsense pantyhose,and a brand new pair of 4 inch heels

[sue ellan]

panties were the first item that i bought

sue ellan

life is like a roll of tp. the closer to the end the faster it goes.

[NicoleScott]

Lipstick (not clothing)
High heels (not clothing)
Pantyhose

[Krististeph]

Fruit roll up. Grape.

First non-edible item: can't remember. One of the first in person purchases : a white boat neck leotard, with color splotch prints, and hot pink tights. Yes, it was the 80s.

[wendy]

My first women's item :

I went on a shopping spree, a nice front zip swimsuit, aerobics wear (with the spandex foot legging), and some shapewear.

[raeleen]

Pantyhose. Easiest thing to pick up off the shelf. I remember feeling terrified, like everyone in the shop knew I was going to go home and put them on after I left.

No one cared. The clerk didn't give it a second thought. I have never gone shopping en femme, but have now started feeling more comfortable buying girl things. And that pair of Q size L'eggs black hose started it all. :P

[xd-tigger]

Mine was a white, 3/4 length sleeve shirt, and a black and white tartan skirt.

[franlee]

Actually it was 3 pieces at the same time, a bra, panties & full slip. All in white.

[Leohose]

Leotard and two pair of tights from a dance store and pantyhose

[Saikotsu]

A white athletic bra with a front closure. I still have it too.

[Veronica putters]

The first item for me was a nice pair of black stockings and a corset and matching panties :daydreaming: i loved them so much

[Jennifer Medina]

A pair of pink pumps from a self service store similar to Payless but that only sold women's shoes. And I didn't waste any time. The same song that was playing on the car radio when I left the car was still playing when I got back, The Police's "Wrapped Around Your Finger".

[donnawilson82]

Before my late husband/wife came out to me, he had never bought anything for himself. He had always tried on his Mother's, sister's or my clothes. For his first purchase, I took him to Victoria Secret. I knew a couple of the sales associates there and I knew they would treat him well. At first David was very nervous but was soon at ease with his new adventure. We spent over an hour getting him measured and trying on different styles of bras. He ended up buying 2 demis, one push up and one full coverage bra, plus gel inserts. David had such a good time that, from then on, he often went back by himself.

[Paula J]

My very first purchase was a pink fishnet body stocking from a sex shop. God, what was I thinking?? Lol. I started out with lingerie and underwear. Now, I really don't care about that as much. I'm really into nice outfits, shoes and cosmetics.

[PamTG]

The very first article of female clothing that I ever bought was a package of panties and when I got home I realized they were too small and then went again and bought the largest and they were too big, it was a learning curve and I started searching for the right sizes in male sizes and now I think I have it down lol

[kellyanne]

Great question !
I think mine was at age 21...a cheesy black garter with sheer crotchless panties & stockings from an "Adult Boutique".
it seemed sexy at the time... not so much anymore.

[Chancey289]

A shirt, which my ex took. :/

[Jan_Muller]

A pink slip,with panties and a bra the same shade, at Sears. My heart was pounding so loud I was sure the clerk could hear it. I thought every eye in the store was on me all the way to my car.

[freeindress]

In late 90's to early 2000's, a matching set of blue with white trim sports bra and hot pants, then swimsuit, bought online; then had the nerve to buy a few other sports bras and swimsuits in a large sports store; then pre-worn dresses and skirts in thrift stores; then mary janes in a brand shoe shop... All purged between 2005-2006 under mind control from non-supporting ex gf :angry:

[Patty's panties]

A pair of green panties. And then another and another. Now I have, what I think, is a very nice collection.

Patty


A shirt, which my ex took. :/

That sucks.

Peace
Patty

[caitlyn aguilera]

black stockings!!!

[Brandy Mathews]

Pantyhose was my first too. Asked the woman if they could be returned if they were the wrong size for my girlfriend. She just said.....yes, of course, if they are not taken out of the package, just keep the receipt. Lol. Then I actually found a vending machine in a hotel that had them in there. I kept that machine cleaned out, lol.
Hugs,
Bree :)

[wantstocrossdress]

Stockings!

Since they were my first, i didnt have any experience and just asked for the cheapest. I was able to buy 2 then went straight home to try them. When i got home, i found out why they were so inexpensive, they were knee highs! i cut the ends off of one pair, wore them over my thighs, and wore the other but i just did not feel right. i went back to the same store the next day and asked for black pantyhose.

[Dana44]

My first was stockings. Oh my my I like them.

[Hunter]

Just a plain black pair of leggings for me. They don't even fit well, I just kinda guessed my size and bought them.

[Sara Marshall]

The first item I bought was a pair of pantyhose

[Sister Rachel]

Tights in Leeds market when I was twelve. Then fast-forward ten years, a maxi-skirt from Littlewoods (nice floral on black number) , and a pack of three bras which were far too small for me:o

[Scarlett Viktoria]

I think it was just a pair of black tights.

[CourtneyBme]

I bought a bra....

[heatherdress]

Number 1 first purchase item - stockings and panty hose

Summary (as of 9/27):

Stockings/panty hose/leotards/garter 56
Panties/girdle/thong 46
Bra 31
Mini/dress/skirt/hot pants 25
Heels/boots/slippers 19
Lingerie/camisole/baby doll 16
Blouse/top 9
Nightgown 4
Jeans/pants 3
Swim suit 3
Wig 2
Makeup 2
Jacket 1

Notes:
- several purchased items as part of sets (e.g. - bra/panties)
- several noted more than 1 first purchases (all are included)
- price and "easy-to-buy" may be a factor with first purchase
- many remember nervousness and excitement of first purchase
- some still have first purchases
- some made first purchase with "for the wife" excuse
- most did not identify where they made their first purchase
- most did not identify when they made their first purchase
- some made first purchase on line
- several first purchases were wrong size

[Katey888]

Crikey Heather... I bet you have lists for everything... ;) (And I'm jealous of the hot pants... :))

Sooo... bought, rather than 'borrowed', right... :o

Tights - there was a fashion prevalent in the mid-70's for a smokey-grey/blue colour, and some with patterns down the side of the leg... little hearts or diamonds... Quite brings a flutter to my diaphragm just thinking about it now.. :daydreaming:

Katey x

[cdheels]

The first thing I bought Was a 6" pink platform heels :D

[Talyla]

I first bought a 3 pack of floral print cotton thong panties.

[trishacd]

I go to burlington coat tj max , marshalls in omaha,the cutest panties,the best prices ,i have well over 100 pairs,i pick out what i like no mater whos there.

[Amber42]

Pair of pantyhose....then nothing for many years. Then my next purchase was a pair of pleaser platform heels.

[gailbridges]

I bought an outfit.
red skirt, white jacket/blouse that had a dickey. I looked like a middle-aged, high-end real estate agent. It was great.
Wish I still had it.
Went out with the purge.

[heatherdress]

Number 1 first purchase item - stockings and panty hose

Summary (as of 10/1):

Stockings/panty hose/leotards/garter 57
Panties/girdle/thong 48
Bra 31
Mini/dress/skirt/hot pants 25
Heels/boots/slippers 20
Lingerie/camisole/baby doll 16
Blouse/top 9
Nightgown 4
Jeans/pants 3
Swim suit 3
Wig 2
Makeup 2
Jacket 1

Notes:
- several purchased items as part of sets (e.g. - bra/panties)
- several noted more than 1 first purchases (all are included)
- price and "easy-to-buy" may be a factor with first purchase
- many remember nervousness and excitement of first purchase
- some still have first purchases
- some made first purchase with "for the wife" excuse
- most did not identify where they made their first purchase
- most did not identify when they made their first purchase
- some made first purchase on line
- several first purchases were wrong size

[Rachel PT]

Pantyhose and then 5" stiletto pumps (Black patent, of course!)

[Petra1]

A mail-order tank dress was my first purchase. Prior to that, the purchasing was done by my girlfriend at the time.

[JOHANH]

Bra, panties, hose the basics. Finding an old pair of panties I use to wear got me started again. They didn't last long as the elastic was quite deteriorated.

[Charlotte_P]

My first purchase for myself was an online order of panties from VS..now my collection takes up two drawers in a dedicated dresser just for mine and the wife's lingerie.

Charlotte

[Christina Page]

It was pantyhose. Loved the feel of them on my legs. I still love hosiery, but these days I prefer stockings and garters.

[Savannah_Skye]

First item was floral A-line dress from JCP. A few weeks later, went bac and bought two more.

[daphne_L]

Shoes! (High heel pumps)

[CONSUELO]

A beautiful black half-slip with the most gorgeous embroidery. I bought it at a small lingerie store from a young and helpful sales lady. Small, independently owned lingerie stores have all but disappeared which is a great pity.

[Jennypowers]

I think the first think I bought was a bra and panty set in my size. Up until then I was borrowing the wife's :o

[Meg East]

A pink half slip from Kmart. After that I didn't buy much for about ten years and the national economy suffered.

[Staci]

Definitely was a pair of panties. Blue with white lace on the front. Nylon bikinis. Very nervous and exciting.

[amandagurl2014]

Red strappy high heel sandals.

[Nicole90]

First thing was two pair of Legg's pantyhose from Walmart. I was super nervous and used the self checkout. What a rush though. From that point on I was hooked.

[Maxi]

A white half slip.

[Billiejosehine]

The first thing I ever bought were a pair of grey boots from Payless.

[Debbie Satingirl]

A blouse in the eighties that I still have. It has shoulder pads and has silver and cream stripes in a lovely silky material very Dynasty

[Luciana]

I had 24 years old. Yes, it was a long time until I buy my first item... Anyway, it was absolutely ridiculous and totally frustrating for me!

I had left the office where I worked and drove my car till a shopping center big department store to purchase a pantyhose. Then I went to female underwear section and my heart was spanking my chest. I was so nervous to buy the thing and get off of there the faster I could that I didn't pay the proper attention to what I was doing. So basically I picked the first pantyhose I saw, passed in the cashier and vanished. I remember till the day that it was pink and that had the word 'Lolipop' in the package. The 'Lolipop' word should have given to me some clue that I was getting the wrong stuff, but...

When I got in home, I ran to the bathroom and locked the door (at the time I still lived with my parents). I was so anxious that my hands shaked, then I ripped the package just to finally notice that it was a pantyhose for <10 kids! I still remember to have tried to wear it (LoL!) but it even passed beyond my foot!

The next day I just throw it in a dumpster and came back to the same store a bit more relaxed. This time I bought an adult black pantyhose that fitted like a glove!

[LydiaL]

So long ago that I no longer remember exactly what. Yet one of my earliest purchases and a favorite was a black leather mini skirt. Yummy.

[Lexi Moralas]

5"high heel " granny boots"

[TaminaPurefoy]

A bra. Hehe. It was very simple, it was the first time I wore my favorite dress (which I found in a closet and washed it, it fits perfectly on me but probably no longer fits my aunt). Anyways, I wanted to look a bit more feminine, so I bought a bra from a girl who sells underwear to TS people on the internet, so I didn't worry about her reaction. She even helped me determine my size based on my male size. So I bought one with a hit of filling and ended filling it with a pair of socks xD

[Kayla_K]

The first thing I ever bought was a pair of basic panty hose. That was probably 30+ years ago. Back then everything I wore was "borrowed" from GF's or sister. I am 6'4" and I always had to pack myself into their stuff. Was very uncomfortable to wear and therefore very disappointing. I never had the nerve to go out and shop for myself and online shopping didn't exist. I stopped wearing because of this, but still thought about it a lot all these years. Finally... last night.... I got up the nerve to do something about it. I went to the local WM and bought a bra and leggings. I didn't have the nerve to try them on in store. I guessed on the sizing, picked them out, went to self check, and purchased. Wow... my nerves were pumping. I couldn't wait to try them on when I got home. The bra fit GREAT but I was disappointed that the leggings were WAY too big. I can't believe how great of a feeling it was to put on a bra that felt comfortable to me and looked good. Way better then what I used to do. I am so excited about it that today I plan on going out and hitting some second hand stores to see what I may be able to find. Maybe I will even be able to work up the nerve to try on to make sure it fits before I buy. We will see.....

[Della]

A pair of panties with hearts on them. I was 18 and told the checkout they were for someone special.

[wilt575]

I started out wearing my big sisters hand me downs, every thing top to bottom yes everything, did this for so long can't remember first item I bought. Mom did buy me a few things. but I for myself??

[Princess Lexi]

I'll never forget that day a pair of shoes bought them at Payless on my way to my girlfriends house it was 15 years ago I spent the next 8 hours feeling crazy and anxious couldn't wait to get home and try them on omg the fear I felt walking into the women's ille and I thought I was gonna pass out as I walked towards the register

[Melissa73]

fiest thing for me: a white bra and a grape colored nightgown from a discount store (in st louis mo) "Grandpa Pigeons!.....in 1994. I had just returned from a trip to Georiga to visit my brother and his g/ friend, And after having gone almost 2 years with out dressing...... i saw her bra in the bathroom.... and it stirred feelings again! (i had gone so long as i was in college dorm room and was quite busy..

[s.e.al]

Mine was shoes from payless, I was so nervous that it took two trips before I bought them

[Princess Lexi]

@s.e.a.l same place for one trip though but I was out of that store in less then 5 minutes the experience was terrifying I took 10 years until I did it again my sisters had tons of clothes so I survived off them

[lisagurl]

pantyhose was my first buy :)

[AllieBellema]

I bought a wig and a sock hop halloween costume at my local K-Mart near where I grew up. I don't typically buy female clothing in a store these days, but that (and one more halloween purchase soon after) were the only times I've ever bought female things in person.

[Karmen]

Pantyhose. I bought a few more after that and wore them under my jeans occasionally almost for a year, before I bought any other female item. Next in line were nail polish and high heels.

[rachellegsep]

4" stillettoes with open sides but with heel cup and ankle strap in shiny black patent look. Tried them on in the shop with my wife for a fancy dress P party (no guessing what I went as).

[brynnewilliams]

Pantyhose.

[stacifox13]

joe boxer string bikini panties 4 pack

[heatherdress]

Number 1 first purchase item - stockings and panty hose

Summary (as of 10/18):

Stockings/panty hose/leotards/garter 66
Panties/girdle/thong 53
Bra 35
Heels/boots/slippers 29
Mini/dress/skirt/hot pants 28
Lingerie/camisole/baby doll 19
Blouse/top
Nightgown 4
Jeans/pants 3
Swim suit 3
Wig 3
Makeup 2
Jacket 1
Costume 1
Sisters clothes 1

Notes:
- several purchased items as part of sets (e.g. - bra/panties)
- several noted more than 1 first purchases (all are included)
- price and "easy-to-buy" may be a factor with first purchase
- many remember nervousness and excitement of first purchase
- some still have first purchases
- some made first purchase with "for the wife" excuse
- most did not identify where they made their first purchase
- most did not identify when they made their first purchase
- some made first purchase on line
- several first purchases were wrong size
- some can't remember

[Alisonforme]

Pantyhose was the only thing I bought for the longest time.
Then bought a cover-up, scarf, and black heels.

I recently bought a wig, make-up, and gloves. That's when things started getting interesting!

[Herbie]

Panties and nylon stockings

[janetcd2]

had to be high heels

[Majella St Gerard]

Panties, don't remember what color though.

[Sindeycd]

pantyhose & then some shoes

[madcitycdph]

Pantyhose, then dresses.

[Leohose]

Leotards tights pantyhose and extra tights the sales girl made me get matching tights to go with my leotard
They were danskins. So nice

[MissDanielle]

Two Hanes Get Cozy ComfortFlex Fit Wirefree Bras (white and heather gray) and a Hanes ComfortBlend ComfortFlex Fit Pullover Bra 2-Pack in both white and pink.

[kittie60]

White flat shoes,fishnets and a nice 3 piece blue satin nighty. Bought at the same time.

[Laurenlovecd]

I would go visit the Lovers Package store and buy full body stockings and leggings.

[AnnaMarie]

Make up - always had a thing for it.
Went for my lunch break to a chemist well away from where I worked with a 'pretend' list of things for my wife. I was single at the time and had a wonderful evening trying everything out!

[Melody A]

A denim mini skirt from Goodwill :)

[Andrea2656]

White bra and panties from a Woolworths that I never shopped in so I was not a "known entity". This was in the '70s.

[JillSierra]

Black patent leather pumps - 3"

[Karren H]

1968.... It was pantyhose and I was 16 or 17. The girlfriend at the time called me and asked me to stop by the store and pick her up some Leggs in Suntan. We had a date that night. I got to the store and of coarse they were giving me the "you pervert" look when I was picking them out. So I figured I'd buy her an pair and myself a pair a since they already thought I was strange! Lol

[NANNETTE]

A pair of black tights from Woolworths. I was 21 and very nervous, I felt sure that the lady Sales Assistant was giving me dirty looks. I was full of anticipation as previously I had only wore my mothers flesh coloured tights. I was dying to put the black tights on but was very disappointed as they were a thin denier. I purged them the next day but managed to pluck up the courage to go on a spree and buy several pairs of flesh coloured tights in Marks and Spencers. I still craved a really nice pair of black tights and eventually bought an opaque pair in 4o denier. I love black tights still do.

[Angie G]

OMG girl that was so long ago I don't even remember most likely a skirt.:hugs:
Angie

[Linda Stockings]

It was early 1980's. They still sold real Hanes Ultrasheer stockings in nice department stores. I bought all they had in my size in as many shades they had. She asked more specifically about the style, and I asked for reinforced heel and toe, 100% nylon, nonstretch, ultrasheer. I should have asked for fully fashioned with backseams, and full reinforcement on the feet....but this was already blowing my mind to just get this far! The sales associate was polite, friendly, and made smalltalk about how wonderful "real 100% nylons that are "flatwoven" are, how much more smooth, and truly sheer than just about all of the so called "ultrasheer pantyhose". She went on to say how much I was going to love their appearance, their silky feel, and how much I would love wearing them. So much for concocting any story that I was buying them for someone else. I just smiled and went along with everything she had already figured out. She was not wrong. There's nothing like them...if you can find them. Sometimes Ebay? She was about the age then that I am now. She dressed beautifully, wore nice pumps with about 3 inch heels, and I would soon find out...real stockings. She dipped her heel out of one of her nice pumps, noticed that I saw it, and she twirled it, pinning the toe to the floor so that the heel raised up about an inch, and she twirled it rapidly. I had never seen such shoe, stocking, foot acrobatics. I don't know what most GG's would have thought of it, but I was very impressed how nice she looked, and how easily she could take a simple thing and by using it for some harmless flirting, TOTALLY capture my full attention. She had the classiness to not overdo it. She gave me a show of her skill for about 30 seconds while we chatted, and then with perfect timing slid her foot back into her pump making a soft, feminine swishing sound. She smiled and blushed a little and said with emphasis: "isn't that sinful"? I jokingly said "I'll buy however many pair you have left in stock"! She thanked me for the compliment and reminded me that I had already bought all they had in my size. I asked her advice on what's best to hold them up, and she happily showed me a short open bottom girdle, pointing out how much I would like the reliability of the 6 metal garters, and the large, smooth, satin panels front and back. And she of course pointed out how it would flatten my gut (she called it my tummy). She said the silky panels would allow my skirts and dresses to slide smoothly whenever I sat, stood up, or walked. She said that without the satin it may cling and not hang properly, failing to give me "a really nice pretty silhouette from the waist down". What a TRUE LADY. She could have easily brushed me off and told me to find a drugstore to buy "one size fits all" pantyhose. I thanked her for taking such time with me, especially where wearing real stockings is concerned. When I had asked for help, I thought she would sell me cheap pantyhose. And to think it was real stockings that I had tried at about age 4 and became forever hooked. Sorry to be so long winded, but that experience of my first purchase holds deep, very pleasant memories for me. Thanks, Linda

[Jacqueline StGermain]

Pantyhose and a white tennis skirt

[SHINY-J]

253456

This was my first purchase. The entire outfit. Teddy, boots, and armlets... I fell in love the first moment I saw it. And what a LONG time it took for me to finally get it!!! Up until this, my entire femme clothing wardrobe consisted of nothing more than some panties that I had sneaked from former girlfriends or managed to steal from one of my friends sisters room. I know, I know... Not very honorable, but I was a teenager and had no other way.

It was in 1998 when I had just moved into my first apartment where I lived alone. I had actually seen this very outfit and this very picture in a Frederick's of Hollywood catalog I had received in the mail a year or two earlier when I was still living with my parents. I never ordered anything from them, but I did have subscriptions to GQ and and Details magazine and I'm sure Columbia House sold my info to junk mail companies... Lol I'm sure that's a blast from the past for some of you! At any rate, I usually got home first and grabbed the mail when I came in from school and it was just there! I was ecstatic! I'm sure some of you remember, but in those days, junk mail was MUCH more prevalent than it is now... Actually, so we're catalogs! But I was way too scared to order from them though while living with my family as I didn't want to risk a package from Fredericks arriving that was addressed to me!

The very first day I was in my new apartment, I ordered it from Fredericks of Hollywood through the mail. Lol I actually tore out the enclosed envelope from inside the magazine and hand-wrote the product code for the specific items I wanted as well as the color and size. I ordered the black teddy, the armlets and the boots! It was Before the Internet was really mainstream. Even though there were actually few FOH stores in the malls in town, I was WAY too scared to go into one to buy it.

In those days, there really wasn't any way to track packages and delivery times... For weeks, I waited.. Checking every day only to find nothing. Then, one day, I got there about 30 minutes after the normal delivery time, and there was a note from the mailman saying that I had a package that I needed to sign for. I was so upset that I had just missed it and that he hadn't just left it! The note said I could pick it up at the postal annex after 4PM. so I waited for a few hours and then drive to the postal annex to get it, but they said that he had still not returned from his route. The person there said they would be closing soon and that he would have him deliver it the next day... Bummed, but happy that my first new and real femme clothes were finally going to be arriving, I signed the confirmation form to have it delivered.
Thinking he would leave it on the porch the next day. I went about my daily business and Rushed home from work only to find nothing other than the regular mail! By that time the annex was closed. So, I went to the annex again the next day and they told me that he thought that I signed the confirmation for me to pick it up at the annex! At that point, I didn't care because I was there now and could just get it then except that they had informed him of this and it was out for delivery that very day. Problem was, I was at the annex at the same time the mailman was running his route and of course, it was a different mailman because the regular guy was on vacation for the next several days!!! Ugh!!! Keep in mind that is entire time, I'm a closeted CD getting his first ever package of femme clothes... I'm already stressing that the package says "Frederick's of Hollywood" on it and that all of these postal workers are seeing that and making all types of judgements and assumptions about me! Now, I've dealt with several different postal employees and the entire reason I did it through the mails was to be discreet! I'm envisioning the package changing hands and getting tossed in and out of trucks... Getting stamped for delivery/return/ delivery/hold, etc... I'm also worried that the box is getting worn out and is somehow going to come open and the entire contents are going to be visible... Lol I'm convinced that the entire cities postal workers are all aware of my secret now!

They state that it will be delivered the next day no matter what... Of course, I had to work, but I didn't take any chances. I went and got some magic markers, tape, construction paper and left a large note telling the postal carrier to leave the package at my front door. I get home and the note is gone and no package.... I'm beyond frustrated at this point... I flop down on my chair, feeling defeated and like the whole ordeal was a massive mistake and literally seconds later there's a knock on the door.... I open it up and it's my neighbor fromthemapartment next door with a large cardboard box. He tells me that he saw it outside my door and didn't want it getting stolen so he picked it up for me. I was flipping out on the inside because I was convinced that somehow he knew what it was, and now I'd be living here with my neighbor knowing my secret, but I tried to keep my cool. I somehow managed to thank him and wish him a good evening... I shut my door and was completely relieved to find that the box was completely intact and not tampered with at all and that the shipping label was electronically generated and had the senders address only. The package was completely discreet.

I shut all of the curtains, closed the windows, locked my door .. While doing that, I began wondering what else would go wrong... Would it be the wrong size, wrong color, wrong item??... But I opened it up and it was exactly what I ordered and expected! Everything fit perfectly! I literally shook with excitement while putting it on! I ended up cancelling a date I had later that night because I couldn't imagine taking these fabulous clothes off! I was so excited to be wearing something more than just another pair of panties! This was an entire outfit! I loved it so much that I slept in it! Even the thigh high boots! I called in sick to work the next day and lounged around my apartment feeling about the best I've ever felt! I knew was hooked for life. Frederick's had also dropped a new catalog in with my order and I spent the entire day going through it while dressed in my new outfit! Despite all of the worries and stress I'd had about getting that first package, I ended up placing a massive order that very same day! I ordered so much that there wasn't even enough room on the enclosed order form inside the catalog!

I REALLLY miss those days...:sad: not just because I was young and the entire world and life was ahead of me... Of course my body was better back then.. My skin was better back then... I had significantly less responsibilities.. Etc. But the clothing and lingerie from those times were SO much better IMO... At least in terms of what my dressing style is. While the Internet made things much easier and faster to get, the styles have gotten much too drab and boring IMO. I miss the outrageous clothing and lingerie! I miss the exotic and wild designs they had! I miss the shiny fabrics and materials they used like satin, Lycra, Cire', lame', vinyl, PVC, etc... I miss when I could order my platform boots and heels in countless colors! I miss when panties actually looked like panties! They were made of satin or other shiny fabrics! They were also high cut which is a must for CDs! High cut makes a mans lower waist, hips, crotch area appear MUCH more feminine! most of the time, they offered them in both full-bottom bikini briefs AND thongs! Now, it seems like the styling has gotten some much more blah. Everything is microfiber or plain cotton... Gross. Just gross... I honestly can't remember the last time I saw satin panties for sale in a store unless it was a 3 pack of waist control "Hanes her Way" briefs. Everything has changed. Whenever I do manage to find platform heels and boots that they actually make in my size, it's always just black or white... Sometimes red, but mostly black and white only. In my old collection, I had two different styles of platform boots and in each one I had a pair of black, white, silver, gold, red, yellow, light pink, and hot pink. Good luck finding those anymore... In those days, it was much easier to get plus sizes too. Almost everything came in size XS up to 3X. I usually got a size 1X as I was skinnier then, but I also stuffed my bras to make myself as busty as possible. I could get away with an XL if I really loved the outfit though. Now, with my forms, to accomadate them, I have to push for a 2X 3X or even 4X to make my look work. These days, it's much more difficult to find my style in plus sizes and even when i do, it's OUTRAGEOUSLY expensive! The majority of what I get now comes from eBay or websites where I can find sellers that can custom make the clothes I like I'm the fabrics I like. That gets really expensive! Things have changed... But I digress. Back to the point...

You never forget your "first"...:daydreaming: and this was mine.

[Michele14]

Bra, panties, and nighty. So another words like many tothers

[Meg East]

A pink half slip from Kmart.

[Bowmanls2]

A full slip and satin panties.

[Alytv]

Black dress and some slingback kitten heels from a mail order catalogue - good grief, that was a while ago. It was terrifying!

[Irish_Katrina]

Panties, bra, slip, and night gown. Felt sooo good

- - - Updated - - -

Does kmart have decent stuff?

[Steph22]

Panties, I was so excited to have a pair of my own.

[JosieH]

Lace trimmed black thigh highs. So sexy.

[Patty Phose]

Pantyhose.

[gokatiegirl]

Makeup & wig

[denisepascali]

For many years I wore my sisters things but my first purchase was actually a tan pair of high heeled boots

[wendy447]

A short leather skirt and thigh high boots.

[Teressa]

Pantyhose at J. C. Penny

[VAWyman]

Mid calf length skirt and sweater at K-Mart.

[KrissyP]

Panties!

[AprilR]

The first thing I bought was American Eagle Mary Jane pump from Payless. A week later I bought a black corset with a g-string, removeable garters and black opaque with bows that I bought from Torrid.

[Sandie70]

Bikini Panties.

[jeni]

4 in black heel, panties and bra. I was nervous but wa s feeling great once I put it on.

[Judith]

Leggs pantyhose. After that, everything else.

[Edina]

A black long sleeve T-shirt with big decolletage.

[Lovely Rose]

Mine was a white bra, It was like 5 years ago, I bought it late at night so the shop won't be crowded. It was a courageous step for me.

[Rebecca Cross Bracer]

Pantyhose...so many pantyhose!

[brandigirl]

Panties and a silk slip

[Tonya Fox]

It was for a Halloween costume, I bought a black and white corset, matching petty coat, fishnets and a wig. The heels I borrowed from a friend, it killed me to give those back. That was my favorite costume I ever wore.

[Brandy Mathews]

Panty hose, Leggs I believe.

[Carissab]

The first item I bought was panties from Dollar General.

[Mandy_K]

1st item i actually purchased was online and was a Fredericks high slit nightgown/ First store bought items were an assortment of hosiery and a bra/panty set from a local big box store

[Sarah Louise]

A pair of black tights from a corner shop when I was about fourteen. My mother only wore beige coloured tights of which I had 'borrowed' a couple, but I was desperate to try black tights. I remember cycling around the neighbourhood, looking for a quiet shop that sold them. I was petrified, but went in the shop and put them on the counter. The man behind the counter made a jokey comment, I stuttered "they're not for me!" but left with my purchase, very satisfied with myself. I still love black tights!

[lostinmyworldcd]

Legg's black pantyhose , and bright red polish ..... An assortment of fake nails was next .....

[Secret Drawer]

I remember quite clearly because of it being a milestone, and because I waited patiently until I had my drivers licence and headed to the nearest city from where I lived (only 15 minutes away). I bought some nylon spandex leggings (what are now considered yoga pants, not sure what changed?) and a leotard. Kinda wish I had ESP or something and bought a whole pile of them, as they are not as easy to come by as they were in the 80's.

[Allison-chan]

My first item was a pleated skirt from amazon.

[carliestuart5]

pantyhose and a bra.

[1958Candi]

Black thigh highs ... and they are still my favorite item!

[Robinadress]

The first was a purple skirt I had seen on several girls in my school.

I was so nervous before I went into the store. I just grabbed the skirt and went straight to the cashier. She must have seen me being so quick, because she asked if I was shore it was the correct size. I just said yes, paid and left. I didn’t even know which size I was using. The skirt was a little tight, but I wore it a lot.