Your First Purchase

[Victoria P]

Hi,

I'd like to know if anyone can remember the very first purchase of women's clothing and when it was?

I can and mine was a beautiful burgundy/black lace set (panties,bra and matching garter belt) and a light blue teddy with white ruffle lace, all back around 1980 the age of 16 or so that I ordered from
Sears catalog! I took a risk as they called me at my parent's home when it arrived in shop! The things we do lol!

Hugs Victoria xoxo

[Melissa73]

oohhh, my first purchase was at Target. I wandered the junior section for hours... cuz i just needed something!!! Finally, i picked a thong leotard (black). Course i got to thinking... If i was gonna buy the leotard. i needed tights too. Course then i got home and even though i loved wearing it. i learnbed i do not like thogs!! lmao

[Cynthia Anne]

My first was a black bra at a K-mart back in 1969!

[Eryn]

Jockey For Her panties. Bought them in person in male mode. Scared to death. I guess the Gender Gestapo had the day off since I got away with it! :)

[Jocelyn Quivers]

Leggs Silky Opaque Tights Blue Size B, purchased from CVS in the early 90's, and I remember nearly having a heart attack while standing in line and placing them on the counter. I still have this pair as a memento/keepsake/trophy/badge of honor.

[Beverley Sims]

I was ten and I wanted a dress for my "sister", I explained that she was the same size as me.
A couple of kindly old ladies I guess they were at least twenty five years old, talked me into trying a couple of dresses on.
A couple more questions, is she older than you? yes 13 well we will put these on to pad you out.
An hour or two later after helping them play dressup on me, I had bought my "sister" a dress.
About a month later I bought a bra and panties after they suggested I could buy these for my "sister" as a birthday present.
I think my "sister" had three birthdays that year.
The best thing is, "They never knew". Did they? :)

[IngeInCO]

Hmmm hard to remember. I think it was a lavender leather skirt from the thrift store. Only $3

[I Am Paula]

I was living in Spain as a teenager. Often went to London. Without much forethought, I walked around Harrod's and picked out a pleated skirt, some sleeveless tops, and a shopping basket full of underthings. No one batted an eyelash, but I think that was typical British stiff upper lip. I think I was 15. I still had no shoes or hose, but I was in heaven.

[Karren H]

My first was a black bra at a K-mart back in 1969!

Yeah! In 69 when I was 17... my girlfriend asked me to stop by the store and pick her up some pantyhose for our date that night... so I bought two pair.... one for her and one for me! :)

[ArleneRaquel]

My first purchase, other than hose and cosmetics,must have included shorts, top & bra because the first times that I went out of the house enfemme I was wearing those items, plus shoes. This was circa 1968.

[MuzzledJ]

I was ten and I wanted a dress for my "sister", I explained that she was the same size as me.
A couple of kindly old ladies I guess they were at least twenty five years old, talked me into trying a couple of dresses on.
A couple more questions, is she older than you? yes 13 well we will put these on to pad you out.
An hour or two later after helping them play dressup on me, I had bought my "sister" a dress.
About a month later I bought a bra and panties after they suggested I could buy these for my "sister" as a birthday present.
I think my "sister" had three birthdays that year.
The best thing is, "They never knew". Did they? :)

Lol, The things we thought wed got away with unnoticed hey! My first item was some wet look black leggens about a week ago, i wanted some lingerie but slightly embarrassed maybe next time...

[stephNE]

Yes, I remember exactly, it was a bra. Previously my wife/GF had bought things for me, for most purchases we were together in the store. In about 1984, there was a lingerie store near where I was working. I had walked by many times and looked in. Finally one day I got up the courage and walked in to look around. The SA came over and want to help, so I explained that I wanted a bra, but had no idea what size to wear. Another SA came out and the two ladies picked out a couple for me and said they wouldn't let me leave until I tried them on, so that they were sure I had the right size. I took off my shirt and they helped me try them on! I picked out and purchased a Bali Sky. Almost thirty years ago and I remember that day like it was yesterday.

[Ressie]

Early '80s, a matching fushia bra & panty set at Sears.

[Jennifer529]

It was a a pair of white tights from Zellers about 1981 and a week later a black dress from Sears.
The sales lady at Sears asked for a price check (yes on speaker) she said it was supposed to be on sale
I turned 20 shades of red,ahhh the good old days :)

[BillieJoEllen]

I was eighteen and on my way to work in a different city. I stopped at a Ben Franklin in a city betwen mine and where I worked. Sat in my car for awhile and finally got up the nerve to go inside. I milled around a bit and wound up at the intimate apparel counterrs. I looked, saw what I liked and picked out a bra and panty girdle (not knowing my size but as it turned out I made a pretty good guess). When I first went in there was very few people in the store. Of course by the time I got to the checkout it seemed like everyone in town was there. Too late to backout now. Two women waited on me. I told them i was embarrassed about what I was buying and that my mother sent me to get these items. They 'reassured' me that everything was ok and not to feel bad. I then went to the city I worked in and went to five different stores to purchase nylons, a slip, a skirt, a blouse and finally and the thing that scared me the most, a pair of white, plain nylon panties. I was waited on by three women at that store and they all kind of gathered around me and asked me a bunch of questions. They all had these big S___ eating grins on their faces. (Think they suspected anything?)

Then I went to work and put in the longest night of work I ever put in. Couldn't wait to try everything on. Finally was able to leave and found a nice quiet place in the country where I could finally 'dress up'.

That was August of 1966. And it wasn't my last shopping trip of the season.

[Marsha Marsh]

I went to Victoria's Secret for the first time in 1986 with my girl friend. I thought that I was in heaven. The next day I back and bought a bra, panty, garter belt and stocking set in a cream color. I was so "high" after buying it I thought that I was going to pass out right there in the mall. I wish I still had that set.
Marsha

[May(be)]

I'm going to answer twice, just in case
First time- Not sure if this counts as it wasn't for me. I went to the Winter Formal at my school, which was an all guys Catholic school (good education, but I'm not Catholic). I took an inflatable date with me to the prom, but I made sure that she was just as classy as any of the other girls there, so I bought it all- Black satin bikini style underwear, black knee-length dress, costume jewelry. Oddly enough I was totally confident in buying all of this stuff, because I knew it was just for a joke. Confidence is contrary to my normal response to buying fem products. Long story short, I wasn't able to enjoy the gag for more than 5 minutes before she was confiscated and I was forced to dance the slow dances all alone.

First time for me- I bought some black leather 3" heels from a Burlington Coat Factory that were mislabeled and were actually 3 sizes smaller than they purported to be. I was so nervous about buying them that I didn't check the size before I ran out of the store (after purchasing them of course). I had to return them the next day and I did so en femme, which was my first time out.

[outhiking]

My first purchase was a pair of pantyhose, this spring, followed quickly by a pleated skirt. I was in drab, so they were purchased quickly, but I've since been able to slow down, a little bit.

[ChristineReid]

Not clothin, as such, mascara! I plucked up the courage when I was in early teens. Then was soooo disappointed when it was brown rather than black! Cx

Fantastic thread! Loved reading about everyone's experiences... Cx

[Samantha43]

A red leather mini skirt, a black sweater and red high heel pumps back in the early '80's. I believe I still have the skirt. Wonder if it still fits???........hmmmmm.:thinking:

[heatherdress]

A pair of black stilleto heels at Payless.

My wife actually prompted me to buy them. She knew I liked her in heels, we discussed it one day when she was shopping, and she wanted me to experience what it would be like to wear a pair. I went to Payless and got up enough nerve to buy a pair a pair. I nervously held to shoe box all the way home and tried them on at home in front of her. We both immediately knew that I totally enjoyed them. We discussed my feelings further, and she suggested nylons, then underwear, then lipstick, then.....

[Karmen]

My first purchase were black pantyhose and panties. I wore them under my jeans. Soon after that I bought my first sandals with high heels, but I only wore them at home when I was home alone.

[melisss2u]

MY first purchase was stockings and tap pants from a small lingere stop. Must have walked by store hundered times inorder to make sure no one else was in there. and for some reason also had to tell the sales assistant it was all for me. she just trated me like any other customer.

[suchacutie]

This took me a while to figure out, but I think my first purchase was breastforms and a bra to put them in! After trying on my wife's dresses it became clear that I didn't have enough on top so before we moved forward I needed that.

I've not mentioned the heels and stockings I bought before Tina existed and were the centerpiece of the outfit that brought Tina to life.

[Robinkay]

MY first purchase was from Sears.......it was a Black baby doll.
I remember being ask by to lady's who worked in the intimate apparel Dept. who I buying it for and I said my mother :o
I then ask for help they said what type of mother did I have......that would determine what I should buy well at that point I just grabbed one and left on my motorcycle.

[joebee]

My first purchase was black lace top stockings and suspender belt, i remember young shop assistant asking if i would like the matching bra, to which i said yes please, it was then i was put on the spot when she asked me what size my GF was, i went red with embarrassment and said im not sure and i left with only the stockings and suspenders lol.

[Stephanie47]

It would have been in 1972 when my wife and I went shopping together for a nightgown for me. I cannot remember if the first purchase was a pink peignoir or a black floor length gown. I still have the pink peignoir. I think the black gown was outgrown. Both were purchased in mid-town Manhattan. Soon thereafter my wife gave me one of her red peignoir which was not soft enough for her-too scratchy. I concurred and it was tossed.

[Joanne.England]

Hi, I remember my first purchases about 25 years ago. A Bra, panties, suspenders and stockings. OMG, I felt so nervous. SA's must have special training to reccognise us and to treat us gently.

[squiffle2002]

I brought 2 things at pretty much the same time - A white satin slip from Debenhams on Oxford Street in London - I still have it and a elastic waisted hippy skirt from a small shop on the corner of Oxford Street and Totenham Court Road, the seller was very keen on telling me that one size fits all, I thought at the time he was referring to me - I think he was probably just persuading me to buy it for whoever and stop dithering and cluttering up his shop!

This was the early 90s.

[eileendover]

Right after I got my drivers license (age 16), I drove to a nearby Sears. I had a "note from my sister" to buy my first pair of pantyhose.

[tammysmiles]

Fishnet tights from Walmart a couple of years ago. My wife, who up to that point had been always been my shopper (to her enjoyment, as far as she tells me) was laid up after knee surgery. While I did want them to wear, I think that even more I wanted to prove to myself that I could do it!

[Tracii G]

I really don't remember.LOL

[Tara D. Rose]

My first purchases were 3 pairs of panties, and fishnet hose, somewhere around 1979.

[anastasiaprincess]

Short Denim skirt from a charity shop in my city ! I have never looked back:)

[Joanna Maguire]

When I was 14yrs on I bought a Berli Sarong Highwaisted OBG girdle and a pair of stockings with my first pay at my first job I went straight into a change room and put them on That was in 1955

[Diane Smith]

I believe it was a pair of mid-heel pumps at the local Target store. Or, around the same time, it might have been a long black nylon nightgown at K-Mart. That would have been 1976 or so.

Not long after, the first time I asked an SA for assistance was when I bought a long black skirt and a white top that were being sold as a set at Bergner's (a midwestern mid-range department store chain). I didn't try them on in the store, but did hold them up to myself to check the sizes, which really amounted to the same thing as far as outing myself to the SA. Fortunately, they fit fine, and I wore those for several years.

- Diane

[HollyH]

The first purchase I made was a black skirt with dotted with a few small sparkly things about 3 and a half months ago. I bought it at hot topic. I tried on a leopard print skirt, a blue/black plaid skirt, and the black one. I regularly shopped there for male clothes and kinda knew the SA that helped me, and she was really polite and helpful. Later on that week, I found out a guy I went to school with 5 years ago worked there and was also a cd.

[sinderella]

Mine was in 1982 from Fredericks, a black nylon unitard, black thigh hose and garter belt. I go to the very same store to this day and even belong to their email subscription which I find to be very nice...because they usually will offer a free pair of panties (just show the email on my phone to them) or other savings or sales exclusive to smartphone users. The SA's are used to CD's and are very helpful. I've tried on many items and have received their oppinions on the items. Sometimes I get a sideways glance from other customers but they don't matter anyway. I'm not there for them. Sad to say, but I've never got the same reception in Victoria Secrets.

[Avi]

I am assuming you mean in person and not online. Mine was pantyhose at Sears 2 years ago in March. I was ok until the clerk asked me if I wanted the coupons that spit out of the register at the end of the sale. Something I had not thought about before hand.

Avi

[Danielle19]

My first in person purchase was in 2010 and was a ladybug costume that I wore for Halloween that year. But actually clothes were from a second hand store and I bought a pair of leggings, ugg boots, a skirt, a red top to match, and a dress! I've gone back to that store many times with the intentions of buying more but I just can't seem to get a time when they're not really busy.

[erika_kerrie]

Great post!

I was 18, and it was around Halloween so I went to a costume store and bought my first wig, shockingly it wasn't very good :). I was so excited to have a wig. I was very nervous buying it, it was busy but I just grabbed one that I thought I liked and headed to the cash. Once I got home, I immediately tried it on. I was so pumped but the experience that later that night, I took a late night trip to a local department store and decided to buy a pair of heels. I was so nervous when I got there, I was looking for something like a black high heel. It wasn't very busy, and I made sure I didn't recognize anyone around. I walked up and down the woman's shoe aisle for five minutes the I saw a nice pair. I wasn't sure my size so I grabbed a shoe then held it up to my shoe and it was too small. Then finally I found something close to my size, just then a woman in her 30's turned down my aisle just as I was boxing up my shoes, I turned quickly and dropped the shoes right in front of her :( she actually helped me pick up one of the shoes and she said, " oh those are cute" then she handed me the shoes. I said they weren't for me, she smiled at me and I took off :) I managed to buy them and made it home without any further incidences. It was so scared but what a rush :)

[KrissyTN]

My first purchase was 2 lovely garterbelts and black silk stockings....with the seams! This was back in 1980 at a Frederick's of Hollywood store. I still have one of the garter belts!

I was 17 and scared to death, but the opportunity to finally wear a garter belt helped me overcome my fears. I had, up until that point, been wearing panty hose and the occasional girdle with garters.

Thinking about it has me smiling!!

[Tera]

Sadly all mine, including my first have been online. But do I get some credit for picking them up at the store at least? Haha. Regardless, first purchase were these adorable 3 inch black leather wedges, nude stockings, and dress from Nordstrom. Went to pick them up and the dress was out of stock :( But wasn't a total bust because when I put the stockings and shoes on it was almost like being high. And in terms of in person, I've thought of every "excuse" listed here, from my sister even to having a note from somebody but still can't bring myself to go do it. It's like I can't shake the fact that "I know they're for me, so the SA's will DEFINITELY know they're for me." Maybe all in due time as I get more comfortable.

[AngieStone]

My first purchase was pantyhose stw leggs remember it well. It has taken off from there.

[michellecd9999]

My first was via mail. I was living in another city than my fiance'/now wife. I got a mailer with an offer for pantyhose and I filled it in, mailed the check and waited( this was in 1978) The panty hose arrived in my apartment mailbox the day I had a guy friend visiting. I pushed the package back in the box and waited until he left to retrieve it.
The first in person I remember was around 1982 when I purchased white panties, bra, camisole, garters and suntan hose in a department store saying they were for my wife for our our anniversary present. I still have those items (well except for the hose...) and still fit in them!

[connie23]

First that I can remember was a pair of knee high leather boots from The Wild Pair. I was so scared but, I walked right up to the clerk and asked for them in size 10.
I still miss them ....
Connie

[RileyEvans]

The best I can remember my first purchase was from Walmart and it was 2 shirts, one was a AC/DC and the other was KISS, they were black with the lettering in rhinestones.

[sonna]

i was 18 couple of shirts from wally world................. all the wrong size!!

[Laurenlovecd]

My first actual purchase was a real wig. I had been experimenting with a Halloween wig that I purchased for a costume, long curly black hair, looked pretty bad but it gave me some ideas......I started looking online for a wig. I ordered one from Voguewigs and I was so excited to actually try it on. I was shocked and thought I looked really good when I got it styled and put some lipstick on . That's how it all started for me about 3 years ago. My first clothing purchase was a pair of 4" heels from the Lovers shoppe. It was the only place I felt comfortable at that time buying heels.

[betty1253]

Can't remember exactly, but bought several half slips and camisoles in the 70's.

[suit]

When I was 14yrs on I bought a Berli Sarong Highwaisted OBG girdle and a pair of stockings with my first pay at my first job I went straight into a change room and put them on That was in 1955

good for you! I hope they were as good as you thought they would be !

[Slip Affinity]

My 1st actual purchase was a pair of nylon panties at a McClellan dept store ... light green.

[sometimes_miss]

I took a post office box when i was 19, and ordered a camisole and tap pants set that a local department store had nicely included an advertisement for in the monthly bill for my credit card. I suppose it was early in the marketing tracking years, as after that i was deluged with ads for woman's intimate clothing. Lucky me!

[miss robyn]

I didn't have my first purchase til I was in the dorms on my first base, bout 5 years ago. We had a P.O. Box so it wasn't a issue of people seeing my purchases. I would say that I bought a pack of String Bikini Panties and a pack of Bikini style Panties.

[Leann68]

Tracii G , I was so happy to read your post because I was beginning to think my age had caught up with me for I cannot remember my first purchase, I am surprised how trying it is to so many to buy fem things.

[JaytoJillian]

yep, this black halter top---still have it--pic was taken last week

[Angela Campbell]

Wow the first time I purchased anything was so long ago, I cannot remember just one purchase. I can say that at the time I was only interested in the underwear so it was probably panties, a bra and or a slip. But then I can't remember the first time I ever purchased a hot dog either. I have bought so many things that have been purged over the years....some only worn once. I would be able to start my own store if I had them all.

[PaulaDallas]

In 1961, my heart pounding, I got up the nerve to ask an associate at Woolworth's for a bra and panties "for my wife." I had put my guess at sizes on a piece a paper, pretending it was from my wife. The lady was very patient and helpful, launching me into a long lifetime of happy shopping experiences. In 51 years I have never had a bad shopping episode. I learned long ago that there was no need to pretend that the clothes were for anyone else. Paula

[Victoria P]

The best I can remember my first purchase was from Walmart and it was 2 shirts, one was a AC/DC and the other was KISS, they were black with the lettering in rhinestones.


Hi Riley, I almost laughed thinking you had misread my questions,then I realized the rhinestones make them girly correct?

Hugs Vicki xo

[michele60]

My first purchase was Sheer Energy panty hose, ya my haert was pounding big time.:battingeyelashes:

[Tiffini Marie]

A way too short red dress and black heels that were a size to small.

I guess that is to be expected when you have no idea your sizes and buy online!

[krissy]

Mine was a green flower dress silk a pink bra and panty set and garter belt stockings,i had to put them on layaway i could hardly wait for the day to put them on my wife helped me choose them i got them out and wore them with her help but after she saw me dressed she didnt want to do it anymore.said it changed me too much.im not sure why ,she was in a lesbian relatioship before i met her but i was wrong in wanting to dress dont see her logic at all

[veroncia]

I do not remember my very first purchase but I do remember buying my first dress at a thrift store in Frankfort Ky on my way back to Southern IL. No one said anything to me but I got out of there in a hurry.

[Terri Semes]

Mine was Hanes panties at Walmart ,bought many other items since.

[Vanessa5]

My first purchase was panties. Got them at Walmart. Kept on buying and then bought bras. For years it was panties, bras, and pantyhose. Then when I bought my first outfit, the pink fog just rolled in and I had to have more. My first outfit I still have and remember it fondly.

[Melanie Vee]

My first purchase was a little black dress for Halloween when I was 18. Of course, I wore it more than a few times after that.

[jacques]

It was 4 pairs of tights over 30 years ago. Tights (pantyhose) only seemed to be in one colour then - "Amercan Tan", but I found some sheer Pretty Poly tights in pale blue and pale pink, and some Mary Quant semi opaque tights in red and green.
happy days!

[AmyGaleRT]

A white peignoir set, from Sears back in California where I used to live. I got a gift box with it, even though I didn't intend to use it. The set got lost in my big purge.

On the other hand, my first dress purchase (and therefore my first start at really bringing "Amy" to life) was a pair of sheath dresses, one in black, one in blue, ordered online from JCPenney.com. I later learned that sheath dresses really didn't suit me, and donated them as part of thinning out my wardrobe prior to putting it in storage. I have much better dresses now. :)

- Amy

[MeganHenry]

Some cheap Kmart playboy string bikini panties, when I was 16 and could drive in Northern CA. :)

[kathtx]

After "the talk" with my wife early in our marriage she took me shopping for some lingerie. I think my first purchase was a full-length Olga nightgown in light blue. Delightful to wear, and she liked it too :)

[BLUE ORCHID]

Hi Victoria, What ever it was it was almost 60yrs.ago

[mersades]

My first purchase was Halloween 54 years ago when I was 17. I drove many miles to another city and bought a bra, panties, nylons, a garterbelt, and a dress. Then I went to a wig store and bought a wig and a shoe store and got a pair of black pumps with three inch heels. It cost me most of my savings. So there I was with a great costume but no makeup and not a clue how to apply it even if I had some.

I wore the outfit in private several times, never applying makeup, before I purged for the first time.

[Ms. Laura]

My first purchase was a mail order Victoria's Secret LBD in about 1995. I still have it, I'll be sad when it finally wears out. In person, actually before that, as I'm thinking about it, I bought a pair of black heels from a Rich's dept. store. Was fascinated by heels as a teenager!

[joanna4]

My first was a pair of used leather boots. I got it at a thrift store in 08 when I was 17 years old.

[Meghan]

I pair of black, 4 inch pumps that were 1/2 half size too small. I bought them in the middle of downtown Hialeah in 1991. Yikes, that was a long time ago!

Meghan

[rookiemistake]

I bought a pair of patent black pumps from Payless in 2009. I've always had a hard time purchasing in public, but it gets a little easier each time. And it's always still given me that "rush." It's like knowing you're doing something wrong or bad, even though this is natural for me.

[Tina B.]

My first purchase was a horizontal pin striped pencil skirt, of multi colors, in a knit fabric, and a white peasant blouse. I was in my early twenty's. I can't remember the name of the store, Zoye's are something like that, in Southern California, I don't know if they are still out there or not, But the where like a Kmart, or walmart, of today. I still remember how scared I was!

[Cary]

My first purchase was of course a pair of black Leggs pantyhose from Walgreens in 94. I was in college still living at home.

[CarmenSkye]

My first purchase was around this time last year. I went on a mall trip in guy mode and decided to spend my holiday bonus on my first outfit. I bought 3 pairs of panties and a tank from Aeropostale, a HIDEOUS polka dot skirt and my favorite pair of yoga pants from Hollister, a pair of flats from Payless Shoes, and a Super Padded Poof Wonder Bra from JCPenny. I had terrible fashion sense...be easy on me, I was TERRIFIED! Lol

[GondorRachel]

I am pretty sure the first thing I purchased was a pair of black pumps, around 2000. I got them at the Kmart the next town over that was along the bus route that ran near my house. Sadly these shoes are now falling apart and are a bit tight; I may have to finally get rid of them...

[Rhonda Ann]

My first purchase had to have been a pair of sheer energy legg's, I'm thinking in the early 90's. I do remember being nervous and almost backing out. After that first purchase seems the rest came easy.

[APRIL0401]

A pair of pantyhose at a local drug store in 1972.

[weekend woman]

If I remember correctly my first was a nylon night gown purchased at Roman's in Woodbridge Center Mall. I think I was 18 at the time so that was 1970. I even figured an easy way to get it into the house without my parents seeing it. I just laid the package on top of my bedroom air conditioner, went inside and reached out thru the side curtain. Did this many times but only at night.

[AllyCDTV]

Yeah I can remember it. It was a black sports bra I got at a K-Mart about 50 miles from my house. I also remember the look I got from the elderly cashier that rang it up. LOL

[Julogden]

For me it was the summer of 1969, I was 18, and I bought some makeup and a few pairs of pantyhose at a E.J. Korvette department store near my home. I wanted to experiment with makeup and didn't want to use up my mother's, and also wanted some article of clothing that I could stealthily wear under my clothes. I wanted some panties and bras too, but I chickened out.

Carol

[SandraV]

Has to be the nylons I had to run and purchase to replace the ones that belonged to mom that I inadvertently ripped while trying on. Back in the day....

[heathr1]

A denim mini skirt from a charity shop.

[LadyPilot]

No Nonsense pantyhose from Safeway, it was 1984 when I was in the Navy, I drove a few miles away from the base (San Diego) to purchase them. This was the certianly start of more things to come!

[Jessica Young]

Teen girls bra that I plucked up the courage to purchase (from self service) at a local K-Mart, buy most my things online but still do occasionally see things that i like in shops and have to build up the courage.

[psion128]

My first purchase was from Victoria Secret. It was a matching bra and panty set. :D


Hi,

I'd like to know if anyone can remember the very first purchase of women's clothing and when it was?

I can and mine was a beautiful burgundy/black lace set (panties,bra and matching garter belt) and a light blue teddy with white ruffle lace, all back around 1980 the age of 16 or so that I ordered from
Sears catalog! I took a risk as they called me at my parent's home when it arrived in shop! The things we do lol!

Hugs Victoria xoxo

[Lacey]

I was 16, I think it was around 1991. Bought a pair of white Keds with my gf at the time. I had just told her about my dressing. So, she asked me what I wanted most and that was what I wanted. I tried them on inside the Meijers and wore them to her house. I like this thread, haven't thought about that in years.

[alwayshave]

I was about 1978, a pair of panties at Jordon Marsh, now Macy's outside Boston.... I was terrified I would be caught and thrown in jail.

[kendras52]

I went into a Hanes outlet store when I was about 25, and bought 2 pkgs of thigh highs almost black stockings, and also a pkg of panties. When I got to the check out, I handed the salesgirl a list I said I had from my wife. I asked her to check it, to make sure I got the right things, she just smiled (what I thought was a knowing smile) rang me up, and out I went.

[irene9999]

I bought the pink skirt in my profile pic! I was too chicken so i bought it online. Nowadays once in a while I work up the courage and get stuff at the second hand store.

[AmyPool23]

My first purchase was 2 weeks, i got some shiny black leggings, leapord print pumps and the week after i bought some lip gloss. I love it all i want more already!!!

Can anyone recommend a clear lip plumping gloss(one that makes your lips tingle)

[Audrey34]

I began ordering from the Sears catalogues years ago. I remember buying several skirts and a couple of blouses and happy as all out when they arrived. It felt like Christmas, lol!
-Audrey

[MaryAnn40c]

hmmmm I thought about what my first real girl purchase was and I don't remember it was soooo long ago:D

[RachelDenise]

It was 1971 and I was 14. I used my paper route money profits to buy a yellow padded no underwire 34 B bra from the JC Penny catalogue. It ame in the mail to my house, and it didn't fit well. BTW I still don't have breasts!

[*ROXY*]

My first purchase was online, M&S bought 4 pairs of silky knickers and 4 nighties.. (I know, but they were on special offer lol).
I was mid 20's at the time. Didnt' buy much for some years later and my first in person purchase was a striped ponte dress from Dorothy perkins followed by a fuschia ping long cowl neck sweat top and leggings and a cable knit maroon jumper from next and then my knee high boots from Alternativefootwear. Only tried on the boots, just bought the other items and crossed my fingers.. they fit!.
Quick question to those who said 'for my mother'... really ? have you ever known a son buy lingerie for his mother ... I've seen this loads of time and I think to be honest the SA would be more wierded out by a teenager buying underwear for his mum then for himself..

[MonctonGirl]

It would have been pink nylon granny panties....long long time ago.

[Lacey New]

Even though i had "inherited" a couple of pairs of panties from several old GFs, my first real purchases were through the mail. I was living alone in an apartment and I had just recently gotten a Macy's charge card. I made several modest purchases of guy stuff and then when the bill came, there were enclosed, advertisements for Pam panties. Briefs and hipsters both white and pastels. I don't remember the price, but I checked off six pairs. a mix of styles and colors and both size 6 and size 7. Sent the bill away and about a week later, a little brown box came in the mail. Voila! six pair of lovely nlyon and lace panties! I could not get that box opened fast enough. I was way skinny then and even the size 6 were a little large - so I just doubled up. I put them on , rode around in the car with them under my jeans after work, very nervously went to the supermarket imagining that everyone had xray vision and could tell that I was wearing panties under my jeans. It was heaven.

Long gone from one of my may purges though. But there have been plenty more purchases since.

[Maria in heels]

My first purchase was a beautiful pair of patent leather metal tip spike pumps from Fredricks of Hollywood...I still have them "enshrined" in my favorite section of shoes. The first dress I bought was a white tank top style minidress with a peplum fringe around the lower waist from Rainbow Shops near my home...it was exciting and scary to walk in after seeing it in the window, and purchasing it 8 blocks away from my home.

[Jana]

Ha! Bought some panties and a bra at Target at age 17. I was scared to death and it took me hours to (1) approach the women's section, (2) decide what I wanted, (3) work up the nerve to go through the register. In fact, I was so nervous that I also bought a gift box and a birthday card to pretend those purchases were a gift for somebody else. When I got home my mom was like "where have you been, we were starting to get worried" -- this was in pre-cellphone Earth, of course. Fun memories!

[JessicaMN]

A black skirted thong with garter straps and thigh highs from victorias secret my sophomore year of college :daydreaming:

[ronda]

to long ago to remember what i boughtbut i think it was a pair of 3 in heels Hugs Ronda

[Rogina B]

I was ten and I wanted a dress for my "sister", I explained that she was the same size as me.
A couple of kindly old ladies I guess they were at least twenty five years old, talked me into trying a couple of dresses on.
A couple more questions, is she older than you? yes 13 well we will put these on to pad you out.
An hour or two later after helping them play dressup on me, I had bought my "sister" a dress.
About a month later I bought a bra and panties after they suggested I could buy these for my "sister" as a birthday present.
I think my "sister" had three birthdays that year.
The best thing is, "They never knew". Did they? :)

They were great!! Don't you wish that always happened[s]?

[willnotwill]

My absolute first was going to the old Montgomery Wards in Balitmore where you could place a catalog order and wait about an hour and pick it up. I ordered panties, a slip, a dress, etc... The dress was not in stock but I got everything else and took it home and tried it on.

[verysexycasey]

first thing I got was a dress and some shirts from forever 21, easy to get online and if you go to the store just say its for your girlfriend =), you feel akward but you get used it to

[Diversity]

Panties. I loved (and still do) the feeling of them. Stockings were next, and then a bra (under the guise of being a Christmas present for my wife). Shopping is so fun!

Di

[Stormy L]

My first purchase was panties and bras from American eagle and breast forms from an online store I am not ready yet to try and go into the store and actually purchase items from the women department yet.

[Ceri Anne]

I would always buy cloths for my wife.........really.......I had great taste and would pick her out stuff all the time, so when I started buying stuff for me, it wasn't a big deal.....until I started trying it on in the store, that was a head trip the first few times, but since then, no problems. My first time for myself was at Goodwill, just wanted to get my own outfit to see how well I could pull it off and didn't want to spend much...........since then have moved to better quality stuff.

[Aubri]

Let me think....It would have to be the black/green bra and panty set with a set of thigh highs. I drove 40 miles to the "big city" with a couple of friends to go to the mall. Was a rush for me at the time. I wasn't supposed to go there, but dangit, I saved the money up, and come hell or high water, I was gettin my pretties!

[Leohose]

Blue danskin scoop leotard with matching tights the sales woman made sure my tights matched my leotard. She smiled and was very helping

[Billie Jean]

A pair of L'eggs pantyhose from a convience store. That was in 1981. Billie Jean

[Beverley Sims]

I remember buying a skirt for myself when I was fourteen.
The elderly saleslady about 30 I think.. :) Said "You will look cute in that and it is a nice color, do you like it?"
I said "Yes" and melted away with my cheeks burning red.

[Joanie_Shakti]

My very first purchase was from the JC Penney catalog when I was in jr. high school, around 1973. They were a set of three "bandana print" bikinis, one in blue and two red, and a set of three "jungle print" bikinis, which had a leafy pattern and an animal applique poorly sewn onto the hip. I actually still have these, though they don't fit anymore and the elastic is bad on the bandana prints. Besides being a pack rat, they have fond memories to me.

Embarrassingly, my dad found the invoice in the trash and grilled me about it. I made up a lie that I bought them for a friend to give to his mother, which is pretty creepy when I think about it today.

My first in store purchase was the day after John Lennon was shot. I was working two jobs and kind of crazy in the head from no time off. Lennon's death was the last straw and something snapped. On my way to work, I called up my day job on a pay phone and quit over the phone. I then drove to a town about an hour away, where I bought a red with black polka dot skirt and button top. I then went to Payless and bought my first two pair of high heeled sandals. I wore one of the pair as I drove home. The shoes fell apart years ago, but again, I still have the skirt and top outfit. The top no longer fits but sometimes I pull out the skirt to wear.

[SandraInHose]

A pair of L'eggs pantyhose from a convience store. That was in 1981. Billie Jean

Ditto here. I don't remember the exact year but it was either '78 or '79.

During high school I worked in a grocery store that sold No Nonsense pantyhose and I helped myself to a couple pair of those. But the first "standing in line and hoping nobody else comes in the store" purchase was the aforementioned pair of L'eggs at a 7-11.

All I remember was my blood pressure boiling then! Nowadays, I really don't give a darn.

[Gretchen_To_Be]

The day after I came out to my wife, my first purchase was several pairs of No Nonsense Great Shapes Sheers in several colors. That was easy because it was a supermarket with a self-serve checkout. That is probably the most awesome invention for closeted CDs ever. The shoes were more difficult. Went to Payless and invented a story about having to do a charity event--"walk a mile in her shoes" kind of thing. Asked for the highest heels in size 12, because I had read that you needed to add 2 to men's. They didn't have anything nice in 12, but I saw a pair of 5" Kosmic black suede platform stilettos in size 11 and I had to have them. I was sweating at the checkout when I had to repeat the story, but seconds later was in the car with MY FIRST HIGH HEELED PUMPS! It was worth the embarrassment. I wore those shoes for hours that first night in my hotel, trying all the various pantyhose shades. Took pictures and sent them to my wife...and the rest is history.

[Laura28]

Was a wig i got in vegas went into the shop and just got it, didnt try it on just said this one that was a strange feeling back then now i dont care and dont make up storys, hell when out with the wife shopping she holds the stuff up to me all the time. But that first purchase was that was 20 plus years ago, right after that i ordered high heels from Fredricks of Hollywood, back then they had size 13 not anymore. i was lucky back then my wife and i were still the same size a 6, now i am am an 11 and she is a 7???? whats with that ...LOL

[Carmen]

To the best of my recollection...I think it was a white longline underwire bra from Montgomery Wards.
I bought many items from their lingerie selection until they closed for good.
I miss that store.

[Randee]

Black long sleeve scoopneck leotard and black tights from Sears. Was 19 and going to have house to myself all week. Went into Sears store on way home from work, just a baby step to later getting up enough courage to walk into dance wear store and try outfits on in the store with the salesladies help.

[misstracy90]

My first purchase was actually just the other day! I bought a bra, a pack of panties and a nice pair of pantyhose. It feels so awesome.

[Danni]

My first purcase was at Victorias Secret, it was a bra, thong, garter belt and stockings, black of coarse. I was so neverous, even though I had told the sales girl that it was for my girlfriend, I just knew she knew it was for me.

[vixk]

A pair of 4" mary janes from ebay... which then spread into full attire and under-armour...

[lonster]

I think my first actual purchase was a pair of thong underwear, size 5. They fit me well, and I wore them fabulously!

[Annette Anderson]

I have just returned from my local mall.I went into the womans store,it has been there for as long as i can remember,as a teen i went there(circa 1979).They had 50% off signs all over the store, half the store was empty,i asked "are you closing) the girl said "yes"

I bought a couple of tops,but memories flooded my head as i left,the years that have past like a flash of light,the path that i could have taken but did'nt.The doors that i should have walked through and the ones that are shut for me now.Maby it was the world being different back then, i don't know.I wished i could go back and start all over again.But time marches on i guess.

Oh,forgot to answer the question,my first purchase was a pair of Legg's suntan pantyhose size B or C i think ,they came in that really cool plastic egg back then.I was a little to nervous to buy panties with them so i went to a different store for them

[LisaSue]

My first purchase was of l'eggs knee highs, very safe. Next though was a pair of bikini panties called Kikis at Woolworth's, both at age 12. Quite a strange rush it was. That and all other Woolworth's are gone now of course. As is the JCPenney where I bought my first thigh high stockings and garter belt round about age 14.

[lauren_m]

My first purchase was of l'eggs knee highs, very safe. Next though was a pair of bikini panties called Kikis at Woolworth's, both at age 12. Quite a strange rush it was. That and all other Woolworth's are gone now of course. As is the JCPenney where I bought my first thigh high stockings and garter belt round about age 14.

I must have been channeling LisaSue, because I hit the same two stores for my first purchases (albeit at older ages)! I bought a light blue cap-sleeved leotard at Woolworth's when I was about 15, and followed that up with tights and hose from JC Penney the following year.

[felicity84]

my first purchase was a foot length black skirt that had slits on both sides that came up to the knee that set me back $.99. it was a polyester spandex blend and a very thin material that was easy to hide in a stone block that had its opening exposed on top.

my first acquisition was a red pencil skirt that i found at my grandmas house that i smuggled home wearing it around my chest and waist underneath my shirt. i still feel guilty about it

i no longer have either piece but i did enjoy wearing them every now and then

[Rabecca]

Well around 14 years old I bought my first pair of panty hose.
My heart was pounding so hard I could of passed out.
Before that I took some pairs from the hot looking lady next store.

[Lacey New]

I had been borrowing panties from my mother and sister for years before I went to college for quick dressing then undressing and then in college, I wound up with a few pair of panties from girlfriends but my first real purchase was after I got a job and was living a bachelors life in a small apartment.

I had just recently acquired a Macy's credit card and in the statement one month, there was a small add for panties. I think the brand was Pam. They offered briefs and hipsters in some wonderful pastels. All I had to do was check the box for color, size and style. So I did and within days after mailing my payment, I got six pairs of lovely nylon panties in the mail. Needless to say, I got a lesson in sizing. At the time, I weighed maybe 140 lbs and size 7 was like a circus tent but they sure felt good.

[chantelle_white]

My first purchase were some cheap tights (pantyhose) from the local store on the corner. I used to get tights and Immac (Veet) in my teens. If I think back on it the lady must have known, even helpfully telling me there were some other colours to choose from on another rack.

[Carla4Guage]

First item I ever wore I purchased for myself (bra & panty set) at age 58 or 59. Anybody know anyone else who didn't start until in their late 50's? Just curious!

[YorkshireRose]

My first purchases were a black gypsy skirt and a blue summer dress, along with a pair of patterned tights (hose).

[Robbin_Sinclair]

I was ten and I wanted a dress for my "sister", I explained that she was the same size as me. A couple of kindly old ladies ....The best thing is, "They never knew". Did they? :) What a great story. My mind wants to believe that they did, or at least enjoyed helping you.

For me, the article is unremembered because I always approached this from the male who wanted to just try it on for a little while. It was usually ill-fitting. Then it was destroyed because of something that I heard in 12 years of Catholic upbringing.

It was red, I'm sure. A dress for my mother, about my size. She's very tall...and then the eternal 'offhand' remark watching for a facial response from the saleslady, "about my size."

[Ariamythe]

Reading through all these was fun.

The only purchases I've ever made for myself have been a couple pairs of pantyhose over the years. I would throw them in with a large order of groceries so they usually slipped past the disinterested box store checkout girl unnoticed. I always had a grocery list with me, ready to flash it and say "My wife sent me" if I got a look.

I think that if I ever purchase anything more daring than that, I will use the self-checkout at the local box store. There's an added level of security in that.

[Robbin_Sinclair]

First item I ever wore I purchased for myself (bra & panty set) at age 58 or 59. Anybody know anyone else who didn't start until in their late 50's? Just curious! Me. I still wonder how much CD is me, when I read about so many girls who started as early teens. I have such trouble with commitments, even with this. Still, I'm convinced it makes me a better person. My relationship with the world as a male was always confrontational. Even my avatar is telling people what to do. Oye Vie. And I'm not Jewish.

[becky77]

I'm not sure if I can remember, I have been crossdressing since my earliest memories but could only actually go out and purchase something when I was 17 and could drive somewhere myself. I think it was a black jersey type dress, I may have even bought a cheap wig the same day. Strange how that first momentous occasion is not more clearer in my mind.

[CorsetAngel]

It's was late 1999, I had just graduated from High School, and had just gone through a horrible break up with my (then) girlfriend. I had been dressing mainly in lingerie at home, that was my mother's, and had experienced many difficulties with her and my dad noticing any and every time something of hers was "missing".
So I went to the local Victoria's Secret, browsed around for a bit, until I found this black second skin satin Merrywidow/ bustier set on display. It had foam push up cups, spaghetti straps, it had a hidden hook & eye closure along the side, and a little black ribbon lace up back, and garters hanging from its hem. It was gorgeous and I had to have it. I ended up going home (after looking up the price), saved my money for a few weeks, and took my own measurements, so I would know what sizing to look for. I went back, and was praying they would have it in my size (which they did), found it again, and bought it with a pair of black lace top stockings, and two pairs of matching panties. (One a brief style, the other a thong). I loved that Merry Widow, but sadly outgrew it rather quickly.