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

[Robbiegirl]

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 ?

[mayarose]

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.

[Michala]

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.

[prene]

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

[CrossKimmy]

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

[sara66]

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

[HollyGreene]

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.

[Cheryl T]

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.

[BLUE ORCHID]

Probably about 4 Years old and never looked Back,

[Bea_]

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.

[NancySue]

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.

[Kris Burton]

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.

[Bluesman]

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.

[Susan_Michaela]

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.

[RachelB.]

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

[JulieC]

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.

[Taylor Dame]

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

[Heather76]

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.

[docrobbysherry]

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:

[Crissy 107]

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.

[Karren H]

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.

[Lacey New]

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.

[alwayshave]

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

[Monique65]

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

[Jillcder]

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

[MarinaTwelve200]

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.

[CarlaWestin]

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

[Celee]

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.

[JesseVF]

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.

[Raychel]

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.

[AnelineM]

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

[Christina89]

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

[Stephj]

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

[StaceyJane]

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.

[AllieBellema]

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.

[Chiffon]

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.

[BrendaPDX]

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

[Cacique82]

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.

[ReallyLauren]

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.

[ronny0]

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.

[Freddi]

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.

[Genifer Teal]

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.

[Maria 60]

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.

[Stephanie47]

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.

[Petra1]

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.

[MsEva]

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.

[Visitor]

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...

[susan2010]

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.

[jacques]

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

[Stacy Darling]

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!

[Alice92]

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.

[Sherry Ann Evans]

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.

[Myphoseleggs]

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!

[danniUK]

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.

[KrissyTN]

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!

[Melani65]

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

[Melinda Jean]

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.

[InAnApron]

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.

[Lori Anne]

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

[Desiree2bababe]

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.

[Joannie]

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.

[cosmolovesph]

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

[Davina4587]

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

[rachellegsep]

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.

[Sasha_inside]

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.

[Kelli_cd]

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.

[Wolfords]

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.

[kellyanne]

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

[praderas]

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.

[Dena]

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!

[NjJamie]

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.

[MarciMaybe]

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

[drobert44]

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

[ColleenA]

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.

[JohnH]

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

[Heather76]

The first time I put on a bra I was about 12 years old. It was one of my mom's bras. The first time I put on panties I was 74. That was 4 years ago.

[ssandy]

I wore my mother?s stockings and girdle at about 10. Once you do it and like it you can?t stop. Worst mistake you can ever make is to buy and purge I guarantee you?ll buy again. The feeling is great
And wonderful.

[Crissy 107]

ssandy, Great post and I could not agree more on both of your points!

[Anne63]

I haven't got to the bra stage, at least not yet. However, I've worn panties for several years, largely for comfort reasons, and probably own far more than most biological women. Only recently have I graduated to skirts. One step at a time.

[Jamie Christopher]

About 10 or 11; mom's girdle under jeans to the supermarket, witch leaded to wearing her bras, no coming back after that...

[Claire M]

June 1969 ..... I was in the bathroom and my sister's clothes were in a pile on the floor. I picked up her panties, white cotton with little blue flowers. I suddenly HAD to know what it would feel like to try them on. There was a laundry basket in the bathroom so after that first time it became a regular thing, just trying them on for a few minutes. A week or two later I pulled one of her bras from the basket. Same thing, I just HAD to know how it felt to wear one.

[Nancy44]

I must have been 6 or 7. I just couldn’t get enough of my mother?s nylon panties and slips. I can’t imagine now that this went unnoticed.

[Joanne108]

Wow I might have replied to this question before. I was nearly six years old. And there was some dress up play. I was dared to try on a bra. I did, and I clearly love it because I still find reasons to wear a bra and all the rest of women?s clothing! I am glad I did!

[Nancy44]

I think it was a wonderously silky black YSL bra and panty set just after I started working and had some money to spend. That was an exciting moment.

[Angie G]

I was Very young maybe 11 or 12 years old witch makes it about 65 years ago.

[Allieboy]

I was a latch key child so I had access to my mother and aunt?s clothing for about 3 hours during the week. Always had a fascination with girls and women's underwear. Around the age of 8, I remember going into my aunts room and putting on a nylon panty and finding a slip with a built in bra. A vivid memory for decades.

[shellyc]

I can remember getting caught by the baby sitter in my mothers night gown. Hid under the covers but she saw me:/

[Lacey New]

June 1969 ..... I was in the bathroom and my sister's clothes were in a pile on the floor. I picked up her panties, white cotton with little blue flowers. I suddenly HAD to know what it would feel like to try them on. There was a laundry basket in the bathroom so after that first time it became a regular thing, just trying them on for a few minutes. A week or two later I pulled one of her bras from the basket. Same thing, I just HAD to know how it felt to wear one.
Ahh the common laundry hamper! I see that I was not the only one tempted!

[Katherine L.]

I tried on a bra for the first time when I was 11 or 12 and found one of my mom’s in the laundry hamper. Bras were always my favorite item of female clothing, so since that first time 50+ years ago I have worn them regularly. I wore my first pair of panties a bit later, probably when I was 15 or 16. They don't have the same appeal to me that bras do, so I've worn them much less frequently over the years, but I still do on occasion.

[Sometimes Steffi]

I'm guessing I was about 12 or 13. I was old enough to be left at home alone.

I always had a plan; Surveillance, plan, infiltrate, accomplish the mission, exfiltrate.

My first mission was to try on my mom's panties. I must have tried on one of her bras shortly afterwards.

I used socks to fill the cups. There had been a rumor about a particular girl at school using a sock to, umm, "enhance her figure." The rumor was that the socks fell out when she was changing at gym class. I never could verify that rumor, but on some days her breasts look kind of lumpy. Anyhow, I thought if she could do it, I could too.

[Donnell]

I was eleven. A teen neighbor had me dress up in my mothers panties, bra and girdle. Through that summer it became a weekly thing on Saturday night while my parents were out. It rose to nylons and dresses. My mom's things were big on me. We eventually started dressing me in his moms things. Her size was more petite and sexier too. We moved away after that summer

[Harriet14]

I live in Ireland, to put context on this reply. About 1965, when I was 16, my aunty, who lived-in as a servant in a mansion, with my grandmother ( her mother) had a boyfriend in a town 3 miles away. When aunty wanted to go out at weekend nights, I would stay to mind granny, aunty returned around 2am. One night, as she got ready to go out, I was caught examining one of her long-line bras. Her response was to ask if I liked those, I did venture to trying her ob girdle and nylons. I'm certain she knew. Sadly she moved to England but no going back on my interest. Now have my own slips, corselettes, girdles etc that I wear with my wife's approval at home.

[CynthiaD]

I was 12 when I first wore a bra. This was also the first time I wore a dress. Both borrowed from my mother.

[Michelle1955]

Around 5 at a neighbor house playing with a friend. She and I switched panties and underwear.
Bras think around 10 or 11 .

[NewGirlChloe]

When I was early teens and my sister was at university, I would wear her bras and knickers when I was home alone. Later I began to try on my mother?s bras, but now I have plenty of my own.

[Samantha43]

I was probably 12 or 13. Dang, that was almost 50 years ago!

[SylphDevine]

I was 9 with panties, although I have a memory of being in a crib and having my mom drape a red slip across my body. Anyway, I wore my moms peignoir with her panties and the first time i was so excited! It never occurred to me that she would know I had worn them. They were very subtle, but they let me know they knew what I had done. So after that I protected myself and carefully folded her stuff and put it back. Never heard a word after that and I wore that set anytime I was alone in the house.

When I was 17, my girlfriend showed me all about bras and how to dress properly and use makeup. She liked transforming me into a girl a lot. So did I. It was grand fun.

[countrygirl]

I was probably about 11 years old. Remember trying on a bra and panites and pantyhose. Felt amazing then natural progression was a dress and the rest is history.

[Maid_Marion]

My wife gave me the "green light" for panties when we had "the talk."
I didn't buy a bra until a couple years after she passed away.
A big event going to the nearest Target and buying a black racer back 32AA bra!
It fit perfectly! It was meant to be!

Marion

[Maxine Smith]

It was quite some time ago, but I'm pretty sure a bra is how I started crossdressing in the first place

[Abby-Becca]

I have always known I was transgender for as long as I can remember, I would fashion my own skirts and dresses out of whatever I could find, in only the way a toddler could. Whilst my dad was very transphobic (this was the start of the seventies) and would make extremely hateful comments, mum was more enlightened and actually bought me some girl's knickers and girl's trousers when I was about seven years old.

Abigail.

[Marketa]

When I don't count few times He tried His mom's bra and panties, when he was in early teens and just fooling around I went all in few weeks ago. I ordered all the basic of wardrobe from underwear and bras to t-shirts and skirts. And then I found out my black knee-long summer dress looks AWESOME when wearing with His white shirt that's knotted under my breasts.

[VanessaV]

at age 11, panties & bras from my mother.. the feeling never got lost I then had to steal form other female relatives/friends but then it was very hard to keep them hidden.

[kimjohnsoncd]

Early teens or a bit before

[Traci H]

I know I tried on my sisters and mom?s stuff early on. But it was in early college days that I bought my first pair of panties, a vivid recollection. They were made to look like denim and actually had a zipper up the front. I had to have them and bought them at Treasure Island. Owned by JC Penney?s and long gone now. They eventually got tossed in a guilt purge, but I remember it took me a huge amount of strength to step into that checkout line back then.

Later I stole a pair of pantyhose at a department store I worked at. I would never steal anything, but wanted them so bad. To this day I have thought about sending them the $1.25 to pay for them. Unfortunately after 50 years they were driven out by Walmart. I hope the good Lord can forgive a young guy driven by this desire and society?s negative guidelines.

[josie_S]

I tried on my mom's bra when I was like 10. But I don't think I tried on panties until I was like 12-13. No sisters, so all I could try on was my mom's clothes. But every now and again one of my girl cousins would stay with us for a while or I would stay with them and I loved the selection more because they were sexier than what my mom would choose

[MarinaTwelve200]

After almost a year of just lipstick, One day, at age 13 or so, I had the opportunity when I was home alone so I just decided, to go "Whole Hog" with my mom's stuff in the laundry basket, and a slip and house dress hanging on the back of the bathroom door. Panties, Girdle, hose, bra, slip and dress, along with the makeup. It all actually fit well (just a little bit loose). And that was the routine from then on.

[Jane G]

I used to wear panties to my first to junior School. So about 7 or 8. Though I had played dress up with my, all girl, cousins long before then. Bra would be about 13 or 14.

[SophiaRose]

Panties at 9yrs old. Early teens for a lace bra which was irresistible. I know I realized it was tabu at 8 for some reason. Never knew how I came up with that fear.

[RachelR]

Somewhere around my early teens I first tried on a bra and panties with what I could find around my house. As soon as i could drive I went out and purchased my own set and that was more memorable.