What were you wearing then?

[sparks]

Since as I've stated before I'm learning lots here about myself and other. I didn't realize how much fun I would have. Some of the fun questions are a little more interesting to read upon so I will try another!
What was the first girly item you decided to wear and if you um borrowed it, who from. I will go first.
I was probably four and I decided punishment for a captured James Bond operative was to be put into women's underclothes. I borrowed Granny's Bra and the punishment was at hand. Oh what a door that opened. Now just look at the fix I'm in!

Yeah I had quite an imagination and still do!

[heathr1]

Wore mother's lipstick and leather skirt without asking:evil:

[bobbi(CO)]

wore my sis's bra and panties

[angie_pacd]

I first started wearing my sisters panties when I was 7 or 8., cute ones back then, nylon, pink, mmmmmmmmm still remember. Then as I got older I started to dress up in all her things, I loved it. I dont know if she ever figured it out.

[Mona]

Ex girlfriend's panties while she was on cruise to Mexico with new BF.

[Casey Morgan]

One more member of the Panty Squad. I don't know whose they were. They were in with my clothes when I took them out of the dryer. A gorgeous pair of blue silk/nylon panties with a white cotton crotch. Whoever they belonged to never saw them again. (I feel bad about that.)

[Jasmine Ellis]

I started wearing my sister's clothes, at the age of 14 years old. I was on my own on a saterday, morning, her door was open, and on the foor was her clothe's, so I tryed them on. Walked around the house of a few hours, and then on every saterday was my day, just couldn't wait.

[TracyDeluxe]

This will sound weird (on this board?, haha!), but I didn't really try anything on. What I used to do when I was maybe 3 or 4 or 5 (don't remember exactly, but waay before kindergarten) was go into my mother's closet, and just stand up inside her hanging dresses. IIRC, they came down to about my shoulders, and I imagined growing up to be just like her someday.

The first time I was actually dressed in female clothing was at a Halloween, and as I have said on other posts, it wasn't good because Mom dressed me in a costume, not like a real little girl, which is of course what I wanted.

Jeez, I'm telling all my secrets here! :blushing:

[Dena]

I almost forgot! My mom had me wear a pair of my older sister's
tights when I was 7 or 8 years old. I was going to ice skating,
and my long johns were in the wash.

[maid phylis]

i first put on my mothers nylons and i never looked back.love phylisanne

[Kimmie W]

My first time came when I was 10 or so. The closet in my room was quite large and extra clothes were stored there. One night while I was looking around in it a white dress caught my eye and I put it on. I knew right away I was on to something

[tammie]

Hi All: My first item of female lingerie was my older sister's black lace cup underwire Vassarette brassiere size 36B. I was home alone and I saw it on the floor of her bedroom and picked it up. I was already hypnotized by the feel of it. When I took off my tshirt and slipped my arms thru the straps I was already getting aroused. When I was able to fasten the band behind me like I had seen my mother do, and felt my "little boy breasts" nestle into those cups and the underwires supporting them I was a full on a crossdresser forever. As I was leaving her room wearing it, I saw the matching lace edged LLPG and it went too. I wore them for 3 days then put them inthe laundry thinking they wouldn't have been missed. WRONG! I was immediately "talked to" by my mother about wearing my sister's lingerie. Despite my denials I was made to promise not to wear her underwear. I think I was wearing a pink Vanity Fair brief of hers at the time too.

The following week I was hot to dressup again so I went to my mothers dresser drawer and discovered slips and garterbelts and stockings too. That was what I was wearing, along with her Playtex bra and pantygirdle when she came into my bedroom to ask if I knew where her slip and garterbelt were. I was made to undress in front of her and she took her lingerie and left me in shame, although she didn't call me names or make any more out of it than that.

It was later that week I came home from school to find my own underwire bra, LLPG, and slip in a shopping bag on my bed. My mother "God bless her" had me try them on in front of her and see that they fit before she cut the tags off. As he would have done for a daughter. Then she made me promise not to wear them out of the house or to let my dad see me in them,and that was the end of it. I was able to dress in my own things for the next few yrs and watch TV with my mother at night. By doing that for me she protected me from the danger of being desperate and stealing someone's lingerie and possibly getting a criminal history.

[Aileen]

My mother's dress, which turned out to be not a dress at all but a romper. I stuck two tennis balls in there where the breasts should be.

[Donna Davis]

My first item was my mothers girdle. I was about 10 or so and I really don't know why I did it but I am glad I did. I moved on to my sisters bras and after I got married,my wifes undies fit real good. She didn't know and when I told her she didn't like it at all. Now I am divorced and have a whole closet full and several draws full of bras and panites. I am dressed in something all the time now.

[SallyH]

Afew years ago I was going through some boxes and found a couple of photos, they are of a little girl with blond ringlets whereing a lovely powder blue party dress white bobby socks and black pat mary janes. on the back is my name and the date 1957, that would make me about two. I wish my mom was still around because I have a whoe lot of questions I want to ask her. Sally

[patty anne]

I was 15 at the time and started "borrowing" my younger sister's panties. Despite being younger, her panties fit as we were about the same size. Wish I had more sister's at the time.

[Foxy Lady]

I was 8 or 9 and tried on my Mom's open bottom rubber Playtex girdle. Slid on some stockings and have been dressing ever since.

[annekathleen]

When I was a senior in high school , I remember one night with my high school sweet heart, she was wearing a white string bikini with red polka dots.
We had just got done fooling around on one of the back roads and I was bringing her home. I asked her if I could have her panties as a souvenier of the night we just spent together. She didnt want to go back in her house without any underwear, so she asked me to wait in the driveway while she ran in for a minute. She took them off and put on another pair and came out and handed me the pair she was wearing. I couldnt wait to get home to try them on. I was hooked. And her younger sister used to leave her sexy panties on the laundry rack in the bath tub. I discovered them one night while using their bathroom. I couldnt resist trying them on, and eventually developed a pattern of taking a fresh pair and returning a pair that I had taken on a previous occaision. And I remember mail ordering a bunch of them for my high school sweet heart but ended up breaking up before I could give them to her. So I had a bunch I could wear until I ended up giving them to my college sweetheart

[Rossie]

My sister panties

[deana cd]

My earliest memory is of wearing my mothers' red full slip. I loved the way the fabric felt against my skin. Soon afterwards I began trying on her bras (which I stuffed with tissue paper to fill them out) and of course panties

[Jessica]

the first items I wore were my mothers bra and panties......knew then I was hooked...........

[Barb Valentine]

At the age of 6 I tried my mother full white slip
after that I use to put on some of her dresses but they were too
long so I cut bottom 6" off (boy did I get crap for that)

[MarinaTwelve200]

12 years old, I was home alone and bravely tried on my mother's lipstick.

Later on I progressed and added her open bottom control front girdle --and hose (using the garters) ---within a year and a half, I was wearing everything.

[SarahHall]

The first thing I tried on was a pair of black lace panties and black leather pumps that belonged to my then girlfriend. It was the most exciting experience. Sarah.

[Helen MC]

I was 12 and it was a pair of my 14 year old sister Anne's white cotton knickers (panties). They weren't a pretty-pretty pair but plain white cotton full briefs with banded cuff leg openings with elastic through these, for British readers they were Cherub brand size 18 or 20 as I recall. To me however they were the Golden Fleece and I was well aroused when I stepped into them and pulled them up savouring the gentle but definite grip of the elastics round my groins and waist, the smooth flyless front and the support of the double gusset (lined crotch for US readers). From then on I would borrow a pair of her knickers to wear every day instead of the Boy's Fronts I was given to wear, only reluctantly wearing them on the days I had to do Gym and PE at school and even ceasing that when I was able to drop PE when I was 15 and I haven't worn male underwear since (I am now 53). I also borrowed Anne's navy blue cotton knickers , these were mostly Montfort brand with the gusset extended up to the waist at the back in a double back panel, though she had some other makes , Cherub, Tenbra, Meridian, Ladybird being a few and I also borrowed and wore some of her prettier panties usually pale blue or pink with a floral pattern and sometimes pairs of my Mum's (Mom's) panties as well which were also patterned but sometimes plain in pastel shades such as pink, pale blue, lime green as well as black and of course plain white briefs similar to Anne's but bigger at size 22, the size I now wear myself these days.

Even now I still often wear white cotton women's knickers similar to the type I have mentioned above and I am wearing a pair as I type this.