At what point in your CDing did you try on your first Bra & Panty

After a bit over a year only, occasionally, into my moms red lipstick, I had a chance when I turned 14. When my parents and sister were gone on a long day trip, I just said , "what the heck" and completely dressed from my skin out, in my mom's hose, panties, girdle, bra, slip and housedress as well as the makeup. Most of the items were from the laundry, so I didn't have to be too careful putting stuff back. That was a fun day, and I got "hooked"--- All "in the closet", so to speak, of course, but that's the way I like it.

It started the moment I put on mom's bra.

I was 9 or 10 when I found my mom?s panties in the hamper. The weird thing is that I had seen them in there plenty of times before but something clicked this time and I put them on. I put them on every chance I could after that. As for the bra, it was at least a year later when my parents would leave me alone. When I would wear both bra and panties it was all over for me. It was a short hop to wearing her girdles, hose and dresses.

Must have been around 6 or 7 wearing and stuffing mom?s bra. Add an open bottom girdle and slip and I was in heaven. Those items were enough for me until many years later. I still cannot fathom what made me make that first perusal into her dresser drawer.

I will chime in here,

For me the underwear started at around the age of 10 with my mothers girdles and pantyhose,
the firm feeling of the girdles was fantastic for me.
It stayed just underwera and lingerie until I got married.
then things got purged and it all ended for a long time.
Eventually it all started to come back. I was in my early 50's by this time.
Only this time it was more than just the panties.
it also included bodybriefers, then on to bras, and dresses. Bought a couple of wigs, (that I never wear)
and so many other things, Now my closet is beyond full. I have been going thru and purging things that dont fit.
Well the things that I can part with. Some things I like too much to let go.

So age 10 for the panties and pantyhose,
50 for the rest.

When I was a freshman in high school, my older sister off to college and I got to move into her room instead of sharing a room with my brother. My sister left behind panties, a couple of bras, a dress or two and some makeup. So I tried everything, although not all at the same time. I didn't do a full dressup until much much later in my crossdressing career

I was about 12 or 13 and it was both of them. They were my first exposure to wearing women?s clothing. I went into my mother?s room and tried them both on. After that it all felt and still feels natural

First bra and panties age 10 borrowed from my sister but this all started at age 4 or 5 my mom and sister would find me when we went to a store they would find me in the lingerie section looking at and feeling the bras and panties. Mom always said I was weird in a special way want to know more pm me

Like most of the others I started with my mom's underwear when i was just a kid. I would stuff her bras with my socks but I felt great.

I was in my teenage years when I first tried on a bra and panty. It didn't last long as I guess I didn't see the thrill compared to wearing a dress. Now these days, I have to have them on if I'm going to dress up, even at home.

About 5 years old, of course mom panties from the bathroom hamper. Her bras about a year or so later even though they were very loose fitting.

I was probably about 11 or 12, I "borrowed" my sisters bra and panties.

Panties when I was 10/11 likely found in the hamper at home. Nothing for a couple years, then hide and seek at friends house, hiding in basement I saw his mom?s panties. Took all my willpower not to take them but I picked them up. They were so pretty. Then nothing until I was working retail at 16. I?d see all the pretty underwear, so I?d go to the other store across town where they didn?t know me and I?d buy them. Vassarette hicuts. Wish I still had them.

I tried on my first bra and panties in my early teens. I loved them because they were garments that were uniquely feminine and made of pretty lace. Fast forward to now and I don't feel dressed if I'm not wearing panties and a bra, and I just love cute matched sets in very feminine patterns and colors.

Gosh I am a 'late bloomer' I must have been in my 40's when I.........
I had been 'into' nylons and thongs for many years, nothing more...
A wonderful friend / girlfriend started gifting me her older outer garments and buying me way too many clearance miniskirts etc etc...
One day I was at her house she suggested I try on one of her bras.. I did get it on, but the band was way too small.
We filled the cups with her panties, but it was not to be. She was like a 32A and I needed at least a 40D or 42DD 40DDD.
It didn't take me/us but a few days until I went from only nylons & panties too everything feminine.
Over the next few weeks WalMart provided Shoes Bra's (foam forms) body shapers etc etc etc...
She opened a door that I never knew existed, and apparently their is no way to ever close that door.
Few years later she 'insisted' I try on her Wedding gown. We both knew it would never fit.
Still she / we wanted to make it happen. It was fun, though after that the gown needed some repairs.

I was probably 12/13 when i tried on my mums bra,panties & tights. Then the next time I added a skirt,then a dress and so it progressed. Fortunately never got caught and as far as I'm aware my mum never found out....or maybe she did but decided not to say anything. It was often said she had want a girl so who knows really. Then from time to time through my twenties & thirties I'd wear a pair of panties when away from home. Until I got together with my now wife when after a while I plucked up the courage to ask to try on a nighty after a while this appeased me but I had to eventually admit I'm might be CD and wanted to try on more things. Its progressed from there......at the age of 50 I purchased (with my wifes help) my first bra. She is very accepting and supportive, will tell me where I've gone wrong,help with make-up,buy me clothing she thinks will suit me. I now have more dresses than her. lol. The only time I've worn her clothing since admitting I wanted to explore more is when we swapped wedding outfits which was great fun but I never would have done it without her agreement......actually when I suggested it she did admit she had wondered how it would look on me.

I would say the first time I dressed up for Halloween. I needed a bra to put something in to look the part. For an age reference I was probably in my mid-twenties. The underwear was and after thought when I realized.
I needed something tight and lightweight to not show through the dress I was wearing. it probably showed a bit but a lot less than guy underwear would. I eventually switched to low rise guy briefs for every day. Everything else just. Seemed too bulky. Abra is not something I wear unless I've got something to put in it. Under dressing as it's called was never my thing

EDIT: I see now I slightly miss read the question but the answer is pretty much the same.
I don't think I put on underwear or A bra until I needed the look. That part was really just a necessity.

I don't know why but when I was young and even at the young age I had something about panties and bras were a very private piece of clothing. I would have only wore my mothers slips because I hated the brand of pantyhose my mom wore and I would wear my sisters pantyhose, she had slips but they weren't as lacy as my moms. Then again the bras weren't as sexy as now, I believe they were called Playtex bras, they were very boring. I was mostly a pantyhose and slip guy but when I told my wife and she didn't want me wearing her things she bought me a pantie and bra set. I didn't tell her I only needed pantyhose and slips but I went along with it and a new experience began. So one could say I wore my first bra and panties when I was in my early twenties.

Probably as a preteen I delved into my mother's lingerie draw. Don't forget the pull-on open bottom girdles and stocking that were also in most women's lingerie draws of the 1950's. However, the first garments I tried on were my mother's full slips that she hanged to dry in the sole bathroom in our apartment.

My first time that I recall was when I was a freshman in high school. At the time, it was all about the experience of doing things around the house with boobs. Wearing my mom's bra with a couple of bath towels rolled up. It got to the point that, when the family would go camping for the weekend, I would stay home alone so I could wear boobs all weekend. It wasn't until about ten years later when I was living on my own that I bought my first bra. Things progressed from there.

For me is was when I found a hope chest in our new home around 1973. There were two Merry Widow corsolettes in there that drew me in so that I had no control but to try them on. They were left by previous owners. They were amazing.

There was a silk petticoat in the crib when I was an infant, which was probably the reason I began exploring my mother's dresser drawers when I was about three years old. But I don't recall "dressing" with any of her undergarments but I LOVED the feeling of silk. However, I'll never forget the inquiry from our neighbor whether I might be available to babysit for her seven year old daughter. It was asked of my mother, not me. I was 12 years old at the time, a rather diminutive boy about five feet tall. This woman worked around the yard in a halter top and short shorts and I was fixated on her curvaceous body... as one might expect an adolescent would be. My mother said yes and I arrived that Friday evening. The little girl was already in bed and the couple left. Almost immediately I went into their bedroom and began opening dresser drawers until I found her lingerie. The first brassiere I ever wore was her bustier with clips running down the front and cups lined with foam rubber. I filled the cups with nylons and was thrilled. I dressed in her lingerie every time I baby sat, eventually trying on some makeup and always finding ways to pleasure myself. That was the beginning of a very long and often troubled journey. I don't recommend it to my friends but when one is bitten by the bug... however it comes into being... it is a good idea to make peace with that reality. I am not a problem to solve...

I started very young (4 or 5) with my sister’s petticoat, then my mother’s slips and pettipants. I didn’t try a bra until I put on my wife’s when I was in my 30’s. I think my first panties was when I bought a pair when I was 19 or 20.

hello Robbiegirl,
first tights when I was about 8 years old - my sister's
first bra when I was about 14 years old - my mother's
first panties when I was 22 years old - my wife's
luv J

I will never look at my upbringing as being a bad one, I'de happily do it again!

My dressing would have inevitably happened, anyhow.

For me it was with my Nanny I'm certain, loved her. She'd be doing the washing and cleaning for us ( as well as her daughters, our secret ) and me being me and her being her. I'de prance about the lounge in one of her daughters dresses or nighties before she then would bath me.

So I started young, and I instigated it all!