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

It?s an interesting question, because for some, cross-dressing started there, while for others, like me, it happened much later. At the beginning around my 5-6 years, I dared to wear only coats, hats, all kinds of my mother?s clothes that I could put over my boys clothes (shoes too). When I started to really want to cross-dress, it was because I was attracted to my sister?s dresses and skirts and for a long time it was only that that interested me. Maybe it was around 10 or 11 that I saw my mother?s panties and bras in the dirty laundry bin and tried them on for the first time. They were not necessarily very beautiful and so I rarely put some under my dresses. Then as a teenager, my sister started having thongs or that kind of thing that intrigued me more because I wanted to be a sexy teen girl too. My love for lingerie developed a lot in adulthood when I discovered all the beautiful pieces that can exist but I buy some mostly for photoshoot. The rest of the time, I wear really simple underwears.

As soon as I got my first private residence (an apartment, around age 22). This was in the 1990s. Without knowing anything about clothing sizes, I worked up the nerve to go to Target and buy a matching powder blue bra and panty set. Then I went home, met someone online, and that same day had my first sexual encounter with a man. I wore just the bra and panty. It felt so right to do that, dressed that way.

It wasn’t until I was in college and out of the house. Maybe ~20 years old. I remember wondering, how am I going to afford these pantyhose and panties. Now I have too many pairs to count!

Early 20s, when I first moved in with my (then) girlfriend. She was size FF though so they fit so badly that I don't think it counted!
Despite dressing in other ways over the years, I didn't buy my own bra which actually fitted me until over 20 years later.

My dressing started around the age of 7 when I discovered my Mom's bra on a stack of towels in the bathroom. Been wearing them ever since.....of course panties, pantyhose etc weren't too far behind as I loved the feeling of wearing a bra!

I started when I was 11 with a tube of lipstick, but it wasn't long before I explored all aspects of dressing, including panties, bras, hose, dresses shoes etc. And thank God I haven't stopped yet. Now it's all my clothes.
Melani

Ooh, boy. Tough to pin down an exact time frame, but I remember I was young, 8 or 9 years old, maybe? As others have said, it was my mother's undergarments that caught my eye and I remember being fascinated with the girdles, hose, bras, and panties of the mid-60's! I recall trying on her heels before that, but the other things really lit the fire! As I grew older through my teens, my sister's wardrobe was a great resource to continue to indulge too.

Probably around 13-14 when I tried first bra. Before that I would just do a quickie with a dress. Then when was old enough to be left alone, added the undergarments. A full slip is still a personal favorites.

I started with my sister's panties, when I was about 13. A bra soon followed, then I was down the rabbit hole lol.

Had to be around the age of 7 if not prior with Mother's girdles and then sisters slips. I didn't try on a bra until I learned of the water balloon titty trick which I immediately wanted to show the world, which I did in fact by stealing sisters bra a body suit. Riding the bike around at dark was quite the thrill but not as thrilling as boldly asking the neighbors where the ball field was. Can't believe I did that, wigless no less.

Perhaps 14 or 15, while doing what teenage boys do the most. I had come by a couple I had hidden is a secret spot that may have slipped over my shoulders once or twice. Panties came later, like 22 or 23. Once that became regular, bras followed in short order.

Panties - teens
Bra (that fit) - twenties (probably tried much earlier)

As with so many others here my first experience was with my mother's bra and knickers when i was around 13-14.

As I got older and had more time on my own i progressed to her dress and skirts

I was 11 when I tried on a bra of my mother's that I stuffed with stockings. I later discover a full length girdle , stockings and a silky dress. I remember that image in the long mirror looked so perfect. I felt so guilty afterwards that I didn't dress again till after I got married many years later and the urge returned.

Panties - I was in kindergarten, getting ready for school and no underwear. My cousins came and stayed over with us all the time so we had a dresser with their clothes in it - my Mom went and pulled a pair of panties out and handed them to me. I remember saying "NO WAY, those are girl panties" Mom told me they are just underwear put them on and lets go. So, I did. They were white with little blue flowers on them. I can remember feeling like I had a big secret all day long and feeling sad when I took them off.

Bra - I was in 5th grade, 10 or 11 years old, and would spend the afternoons at a friends house after school every day. One day his mom was doing laundry and had the basket on the couch, I walked through going to the bathroom and saw a stack of folded panties in it. I don't know why but I reached out and grabbed a pair and stuffed them in my pocket. Went home right after that and when I got to my room pulled them out and checked them out, the beige nylon and lace felt so cool slipping through my fingers. I put them on and was blown away by how good they felt. Over the next few weeks I ended up grabbing four more pairs of panties (yellow, white, brown, and another beige pair)and a beige nylon and lace bra that matched that first pair of panties. The panties were size 5 and the bra was 36B. The first time I pulled the bra on I made sure I had the matching panties on too, it felt awesome and when I looked in the mirror I just smiled. I was hooked and wore them until they were too small for me.

I don't think my friend ever knew, but his mom made a comment once about things going missing and having to be replaced while she looked me right in the eye.

I was 11 or 12 the first time I put on some panties. That was the extent of my dressing until 7 years when I put on my wife's bra. That hug was delightful! That event started me dressing in more items.

Wearing my gorgeous aunt's pantyhose, aged 14. She had gone away on holiday and had asked me to look after her cat. One the second morning went upstairs to the bathroom and there was a pair of her shiny pantyhose draped over a chair. (15 denier barely black, can even remember the shade). They felt so beautiful to the touch and I knew immediately that I had to wear them. It was such an overwhelming feeling and the aroma of her scent and woman musk made it even more exciting. Walked into her bedroom and and as I sat on her pink bedspread admiring rows of high heels, floaty dresses and corsets I knew I had to experience more. To be alone in a woman's bedroom, admiring her most personal items only added to my intense excitement. The lingerie draw by her bed was half open and was full of panties, lace bras and silk. It was like I'd gone to heaven as I caressed and touched them. My abiding memory was stood in front of aunt's dressing mirror, wearing her beautiful pantyhose and a black corset. The corset had little buttons in the gusset and as I slowly unclipped them I was totally unprepared for the orgasm that course trough me. I was still shaking a minute later. It blew my mind and that was the beginning of my lifelong love of hose and lingerie.

... 8 in but first was a 1 piece swim suit with a built in bra which melted me

I must have been 15 or 16. I remember very well because the feeling of the panties was "electric" !! It changed my life for ever.

I was about 10. I started with panties. I have 5 older sisters and when my mom did the laundry she would leave a basket of sheets in our bedrooms for us to make our beds.
Quite often while making my bed a pair of white nylon full brief panties would float out which I would put back in the basket and take it were it needed to go. It wasn't long
before I was familiar with handling panties and then the day came were I was compelled to try them on. The first time I tried on a bra, panties, garter belt, nylons, high heels
and a full slip was wonderful!

At about 12 or 13 I was sleeping in the guest bedroom where some older visiting relatives occasionally stayed, the room also served as a sort of secondary closet for my mom's items.

For whatever reason, one night I went looking through the closet and found a bag of pantyhose, along with a pair of black go-go boots. I had worn them a few years before for a church Halloween contest along with an outfit borrowed from the girl next door. I don't remember much about the Halloween contest but I so clearly remember putting them back on that night, for the reason everyone can probably guess. It was no more than a week before I tried to up the magic by trying on bra and panties and by summer I was using every chance I got to get as fully dressed as possible. Add in the occasional "sick" day during the school year and I was trying to live the day as a female, from showering to breakfast in nightie and robe, to an office look and hopefully an evening look before having to clean it all up before the siblings came home.

At around 5, I found my sister's ribbed purple tights in the laundry basket, and I was instantly hooked! They felt so smooth and electric against my skin. Next thing I knew, I was pairing them with a snap-bottom leotard ? I've always loved how leotards make me feel smooth and feminine. Panties weren't a thing for me until my early teens, and even then, it was mostly about what I could sneak without getting caught, now its every day. bras weren't a priority, don't get me wrong, I love a bra & cute top now, but it's always been more about feeling great and completing the look.
:o

I started wearing panties 8 years ago when I began dating CD's.

When I was 9 or 10, I had gotten my hands on a pair of black, lacy panties, no doubt from one of my sisters, that I would slip on under the covers in bed. The lacy aspect felt so good and different, and the black was a stunning contrast to my boring tighty-whiteys.
The day that stands out in my memories, though, happened when I was 12. I was home alone on a Saturday. Everyone else in the family was going to be gone for hours. I was supposed to be reading for a school book report. Instead, I raided my older sister's closet and tried on her clothes for a couple of hours at least. That may well have been the first time I put on a bra.

I started wearing bras about 12 years ago when I was 60 years of age. I started with a B cup size. But thanks to estrogen I have developed into a DD cup. However, I wear men's cotton briefs as I prefer the fit. I have panties left over from my first wife that I have worn only if all my underpants were soiled.

John