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

I beleive i started sneaking around when I was about 11 trying on my sisters dresses. Back in the mid 60s girls wore mainly dresses and with one sister a year older and one a year younger, I had lots to choose from. Everything from party dresses to girl scout uniforms to Tutus ! I just thought it was fun and funny !

Well several years later my mom was folding laundry and there was a frilly blue bra and silky bikini panty set of my older sisters. Without thinking i picked up the bra and started laughing at all the bows and lace and kind of joking about what silly things girls wore. After a minute of this my mother told me if i didn't put the bra down and shut up that she was going to make me wear my sisters underwear ! I was shocked !

Well after that I could not help but wait for a chance to try them on, and when I did they fit perectly and I really realized for the first time that this was something I was going to enjoy for the rest of my life !

So for me women's underwear came later in the game.

Do you recall the first time you were in a bra and panty ?

For me panties were the start, first my mother's and later my wife's. My first bra was one of my wife's and was probably about 20 years ago. It's only since we've separated that I've ventured into my own female clothing that actually fits. I only bought my first dress and high heels a couple of weeks ago.

Don't know exactly but it had to be similar in age to your experiences. Had a sister but she was smaller than me and her bras didn't fit as well as my mother's. When alone I started at about the 12 year old time, give or take a couple years. that expanded into hose with garters, dresses, etc. Always felt guilty but couldn't quit until I went to college and that was for many years. Started again when I was close to 50. Never got caught but wonder if my mom noticed her clothing maybe not as neat as when she put it away.

I do not remember exactly but I was young like 10-11 when I my tried on my sisters and mothers Bra & Panty

I must have started to explore lingerie when I was at least 11-12 years old

I was 4 or 5 when i tried my mom's bra. I was caught by my mom when i was around 8 wearing my sister's panties. Things escalated from there. I don't know when I started with dresses, the earliest I recall was around 10-11ish.
Sara

My mother bought my sister her first pair of panties that were not "schoolgirl panties".
They were nylon and had ruffles around the leg openings.
My sister didn't like them so she stuffed them at the back of her drawer, never to be worn again. Or so she thought.
I wore them regularly and put them in the laundry the day after I wore them. My mother washed them and returned them to my sister's drawer thinking that my sister had worn them.

First bra was not until I was a university student, when I bought one of my own.

I was 5 or 6 when I first wore her panty.
It wasn't long after that that I tried on her bra. My favorite though was a pink OBG with a satin panel and garters. It had hook and eye in the back and a zipper up the side. It felt so incredible to wear.

A few years later I was a bit chubby and jokingly she told me, in front of a neighbor, that she might have to get me my own if I didn't lose weight. If she only knew how much I would have loved that.

Probably about 4 Years old and never looked Back,

My mom and sister wore the most boring, function only bras and panties that I was never particularly drawn to them. I don't think I ever tried on panties until after I was married. In the couple of years of puberty, I would occasionally use find a bra hanging to dry in the bathroom and wear it as something feminine to aim my testosterone for a few seconds. That only happened a few times.

For the first several decades of my marriage, I think I tried on panties a handful of times. I tried on bras even less. My wife was/is well endowed and i just never really got to where i liked the big cups. I was a skinny dude and had no definition in my chest back in the day. Totally flat. In my early thirties, i worked a very physical job that caused me to gain muscle mass and I started going to the gym during those years to add to the improvements. So, I got pecs that have since descended into a fairly passible breasts.

I have my own A/B cup bras and have learned to love wearing them daily.

At 7, nylons were my first experience and to this day, are still#1. Mom?s panties were too big. I tried a bra, but it was too small. Now, retired, I dress every day. I love and wear hose, panties, and bra daily. Very enjoyable.

LOL! For me, the whole crossdressing experience came all at once. I didn't start until I was 69 (72 now) and after purchasing my own pantyhose, heels and kimono robe the rest came in very short order. I'd say the bra, forms and panties came within the first 2-3 weeks of my first foray into the CD world. I guess without the guilt/shame feelings or feeling the need to hide I progressed more quickly than most.

First panty when I was 14, stolen from a theatre dressing room. Shortly thereafter came a nightgown discarded by my mother and some other nightgowns I discovered in a trunk in the attic. Various purloined panties over the next several years. Bought my first bra and panty set ( mail order from Macy's) at age 20 or so.

First time panties & bra when it all started 1982 so 42 years ago for me. A lot of purges over the years but for me never had the thought or urge until 1982. Still a long while and since getting it all figured out in my head haven?t stopped since. It?s until the good Lord finally takes me now. I feel blessed to be where I am now I just wish I?d come to terms with all this earlier in life. But for the remainder I?m set and content with finishing out the remainder content and at total ease which is emotionally great for me.

I really don't remember trying on just a bra and panties. I remember putting them on and looking for a dress to try on. I kept pushing the envelope until I got to where I am today

I don't remember the first time I wore panties. Bizarrely, panties have never had the impact on me that others have experienced. I have panties, and I wear them from time to time, but I prefer wearing pantyhose. I don't like the look of panties under pantyhose either on me or my wife. She never wears panties when she wears pantyhose now, thanks to me :) If I were panties while underdressed, I usually completely forget that I'm wearing them. So, it's sort of like...what's the point?

I don't recall the first time I wore a bra. It was likely my mom's, but I just don't remember. I go my own first bra as a give-away a long time ago. It never fit right, and just didn't feel right. It had no impact on me, crossdressing wise. Fast forward to just a year ago, and with my wife's help I got my first two brand new bras. They both felt fantastic, and I've been hooked (no pun intended) since.

Tried on my mother's bra and panties at about 12-14 years old, and I never looked back.

I was somewhere around 11 or 12 the first time I put on one of my mom's bras. I did this from time to time until I was 15 or 16. I put on my first pair of panties when I was 74. That's when I started CDing. My youthful escapades were something I always attributed to childhood curiosity. I had never considered cross dressing until I started at age 74. It simply never crossed my mind, but, here I am loving everything having to do with it.

You're going to love this, Robbie. I have no idea when!:eek:

Because bras and panties r not all that important to me!:straightface:

I CAN tell u when I first tried on a mask or a silicone suit, tho. But, I'll bet u care as much about them as I do bras and panties!:devil:

I was around 11-12 when I started with my mother’s panties, bras and OBG. I was absolutely in heaven and can remember those times fondly. I also was worried about getting caught but it never did happen.

I was 7, 1959. And I was obsessed with long line girdles and bras. Used to sneak into moms walk in closet when she and dad were having an evening out and out sitter was to involved with my new born baby sister, my brother and what ever was I the TV at the time. Bra, girdle, stockings, heels and a pink baby doll nightie. It was an amazing feeling. Mater of fact I am still obsessed with them to this day.

Somewhere around age 13 or 14 I tried on a pair of full cut nylon briefs that were hanging out of the clothes hamper. Probably belonged to my mother but my sister wore similar ones. That started the whole mess for me. Then, not too long afterward I hit the jackpot and the miracle of having time to myself alone in the house and nylon panties and a bra in the hamper at the same time gave me the opportunity to wear both panties and a bra. I kept looking for any opportunity after that. However, it was not until I was in my 20?s when I was out on my own in an apartment until I was able to buy and wear my own bras and panties.

4 or 5 for panties. I'd say 13 or so for a bra.

I started with my mother’s OBG and stockings at around twelve and soon progressed to my sister’s bra and panties.

Around ten I remember stuffing with socks I do not remember any matching sets.

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!