First bra

[Nancy Richards]

Is there a story invoked in your first bra. My first was because of a girl friend at the time. We were kidding around and I asked it felt like she one out of her dresser gave it to me told me to see for myself. I have not looked back it felt so good.

[Cheryl T]

Not the first I owned, but the first I wore.
It was mom's. I had been wearing her panties and decided to go further. It was like a switch was turned and I just felt so ME.
The rest, as they say, is Herstory.

[KrissyTN]

Same here Cheryl - my Mom would leave her bras separate from the rest of the laundry basket in our bathroom and one day I just decided to try it on. I added the panties later on, and at that time I could fit into her 2" high heels. One of my favorites was a swimsuit she had with the pre-formed cups. Loved wearing that! It was bright yellow and it just so happened she had a pair of yellow heels that went with it perfectly! At least I thought so in my limited time and ability to dress back then. ;-)

[Stephj]

The first bra I wore was my sisters. I was ten she easy thirteen. I wore it quite often. My mother caught me wearing it twice. On the second time we had a talk I told her I really enjoyed wearing one and that I liked wearing panties too. She said if I wanted to wear them I had to buy my own. So with allowance I had saved we went to the store. I bought two bras a black and blue along with two pair of panties black and blue. My mother made me tell the sa they were for me. That was forty seven years ago and I still wear a bra and panties everyday. I have twelve bras and to many panties to count now

[sara66]

I was 4 or 5 when i try my first bra on. I was in the laundry room and mom's was in the basket. On it went, hooked like crack.
Sara

[Alexis00]

Took a bra from a laundry basket from a friend’s house that belonged to his mom. Probably age 10 or so.

Had it for a few years until my first purge.

[Karren H]

Mothers bra was the first one I wore, when I was 7. She and Dad were out on the town and the sitter was too busy watching TV and taking care of my brother. In her walk-in closet along with her long line girdle, a pair of nylons and a pink babydoll nightie. They all felt amazing! The first one I bought was in college at a thrift store. We were buying clothes for a hobo parade and they had pile of used clothes in the back room. Besides my male hobo clothing I picked up a bra and corset. The checkout lady didn?t care. Think I paid $2 for everything. That was 1972.

[Crissy 107]

I was 12-13 and I tried my mothers bra and absolutely loved it. I tried on everything else there was also. Who knew I was not alone with this.

[Katherine L.]

The first time I wore a bra was when I was 11 or 12 years old and tried one of my mom’s bras I found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any I could wear. One time she caught me trying one on, but didn’t make a big deal of it. I was extremely embarrassed at the time, but not enough to ever stop.

[Helen_Highwater]

I'm not sure. It could have been one of my mom's Playtex Cross your heart, you know the one's that looked like they were body armour or years later on one of my then GF's.

I've a vague recollection that the first bra I bought was of course too small, red and from Littlewoods dept store.

[BLUE ORCHID]

Hi Nancy :hugs:, Probably around age 4 or 5 with one of mom's bras, >Orchid**0:daydreaming:0**

[Rachel05]

I remember the first one I wore, it was my big sisters, a gorgeous purple lace halter neck bra, I still remember how it made me feel to put that lovely item on and how I kept going back time and again to wear it and each time it felt so good, that was a very very long time ago and still I remember that lovely feeling

[Teri Ray]

My first bra wearing was diving into a rag bin in my home when I was 6 or 7 and finding one of my mothers discarded bra. Put it on and found I liked it. I recall it seemed to be a plaxtex cotton bra not very fancy. After that I began trying more of my mothers things.

[Victoria1]

Same story here. It was either one of my moms or my sisters. It was plain white. I don't remember if it fit or not. I didn't really care. It felt good and I've one frequently ever since.

[GretchenM]

I was 6 or 7. My mother often walked around the house without a blouse and in her bra. It all looked so amazing to me and seemed to sort of flip a switch in me to the ON setting. I was about 7 when I decided I needed to try one of her bras on. "Holy Cow, what is this incredibly wonderful feeling I have?" was something like the way I recall feeling. So many switches turned to ON.

Perhaps it supports the idea that this behavior we have is possibly a predisposition we are born with that, at some point, gets activated. The answers others have given also seems to be that way. But it is just an assumption. Either way though, I suspect for many of us bras are defining with panties being the other thing that is defining. They are the most intimate garments and the most transformative or validating of deeper feelings. Whatever it means I don't know, but it sure is nice. Life without a bra is hardly worth living. :battingeyelashes:

[Amanda77]

My first bra was one of my sisters, I have three older than me. It was a training bra i found in a box of clothes in a storage closet i was playing in for some reason. What a fantastic feeling when I put it on. Had it and others on many times along with panties.

[Diane426]

My mom was always the best dressed women around and from my earliest years I always wanted to dress just like her. She was very classy with her bras and panties. Her dresses were always very pretty and classy. Wearing my mom's cloths made me feel closer to her. Thanks Mom.

[Joyce Swindell]

I don't recall my first bra actually. However, I do know that I have a real obsession for wearing one these days. I'm happy with getting older and actually having more to fill them with as well.

[nicole01r]

My story the same I found an old beige bra of my moms in a built in hamper and tried it on when I was around 8. Finally I noticed it was always in the same place so I found a hiding place in my room and would wear it occasionally at night. I then discovered an old nighty that also was never moved. It had lace straps that were just as wide as the bra straps and made me feel amazing. Since that day I wore both almost every night not knowing how I never got caught but I did have my own room and my 2 younger brothers never came in at night. I took these items to college along with other finds I made and now have 17 bras at last count .

[JenniferMBlack]

I dont really remember my first bra. But then I'm not a huge fan of bras. They serve a purpose of holding forms in place. I was amazed the most comfortable ones I have are cheap ones from Walmart. I actually had to get rid of one if those today. After having it two years the wire is poking through and thats no good.

[Jeremie]

So there is first time in a bra, my first time trying on a bra, and then my first bra... to me, these are all different. When I was really young, 5 or less, I was put in a white bra with a wig and a big straw beach type hat with sunglasses. Make up too but I don't recall what exactly. I remember running through the yard. No clue why my older (10+ years) siblings dressed me up like that... Probably just something fun to do I guess. Had zero impact on me. I was just a little kid.

First time trying on a bra was one of my mom's of course. It was white as well. Since probably 10 or so I've always liked women's clothes. Bra, panties, girdle, slip, one piece bathing suit, dance leotard and tights... all of these experiences were at my parent's house growing up.

My first bra I bought with my GF. Still have it. It's black with a white section along the upper third of each cup, green polka dots, and some green and white trim, and a small green silk bow between the cups. Has matching hipster panties. I love it even though the band size is too small and the panties never fit. Still can't bring myself to try anything on at stores, but would be so much better if I would. Have a fair amount of things that are too big or too small. :(

[MarinaTwelve200]

My mom's laundry hamper when mom and dad and my sister were visiting cousins a couple hours away. I was 13. Since age 12 I was only doing Lipstick when I had a chance----and this time I said "what the heck!---Go for it" SO I did the bra (stuffed with my own balled up t-shirts), panties, a open bottom girdle, a slip, Nylons and a housedress. A scarf around my head (no cheap wigs then) and the red lipstick.-----Unfortunately, My feet were too wide for her shoes.---My first time DRESSED! The breasts seemed especially weird and interesting and my hands kept accidently hitting them. Needless to say, I had a couple of hours of great fun before I undressed and returned everything back to its place.----So I dressed from then on when I had the chance of several hours of "Alone time". ----Never got caught.

[Jennifer in CO]

when I was 10 - my first 'bra' was actually a bikini top. Then the next day my first training bra. My first 'bra' I actually needed? about 7 months into my transition. I was running down a flight of stairs (you know - skipping a step as you "run" down a long flight) and realized close to the bottom that my chest was trying to kill me by jumping off as my new almost "a" cup breast were bouncing up and down. Holy crap that hurt!!

[laurie103]

I was older. Like 22 or something. Woke up one morning after drinking and decided to go for it. So nervous, went to Walmart and grabbed the first one I saw. Took a nap in it early in the day. Baby blue. It was way too big.

[Christina89]

My first bra that I tried on was my mother's. It took me a bit to get it on. But as time went on I got the hang of it.

[Nastasha]

My first bra that wasn’t a quick on and off as the result of truth or dare with my sisters was a friend’s mom’s when I was 11. I used to be over at his house all the time after school and over the summers and they treated me like one of their own kids. We were sitting there eating chips and watching cartoons one day and his mom came out of her room and over to the hall closet. I was sitting in a chair right at the entrance to the hallway so when she walked out I looked down the hall, she was wearing a pair of jeans, no shirt and a bra (beige with lace on the cups) I just stared. She didn’t see me in the chair as she grabbed some tp out of the closet, closed the door and walked back to her room.

I had seen her in her bra and panties a few times over the years, little quick views as we would walk by her door on the way to my friend’s room and I had seen her bras drying on the shower rod and had watched her fold her panties countless times when she was doing laundry. The same was true at my house when my mom and sisters did their laundry or walked around in bra and panties, seeing someone in a bra was nothing new. But that day for whatever reason I couldn’t look away from her bra.

A few days later we were out in their backyard playing after school and I had to run in to use the restroom. My friend stayed outside and his mom was over at the next door neighbor’s house … so I walked back to his moms room, looked up the hall again and then went into their room and looked out the window, my friend was still over in the corner of the backyard so I went over to the dresser, opened the top drawers and found her bra and panty drawers. I looked outside again and then looked in the bra drawer … there it was, a beige bra with lace on the cups.

I had a sudden NEED to try it on, I had to see what it felt like so I grabbed the bra and closed the drawer went to close the panty drawer and again had a sudden urge to try them as well so I grabbed a blue pair off the top, closed the drawer and ran to the hall bathroom. Once I was in the bathroom I stripped down and put the bra and panties on … WOW. Everything felt so right, the smooth cool nylon of the panties, the nylon and lace of the bra, I had never felt so great.
KNOCK KNOCK KNOCK – “Did you fall in or what?” my friend hollered from outside the door, I’m standing there in his mom’s bra and panties and was just frozen. He knocked again so I hollered back that I had a stomachache. He laughed and walked away and then I hear his mom out in the hall asking me if I was OK, she had just walked in and heard me saying I had a stomachache, did I need anything? No, I’m OK, thank you. I was in total panic mode … I’m standing there in her bra and panties talking to her … what do I do? How do I get her clothes back into her room without getting caught?

I pulled the bra and panties off, put my clothes back on and then stuffed her undies into my pants. I waited a few minutes, flushed the toilet and walked out hunched over holding my stomach (actually holding the bra and panties so they didn’t fall out), his mom was standing in her bedroom door and my friend was in the chair by the hallway. Now what? I had to get out of there so I told her I was going to go home because I didn’t feel good and headed out the door and over to my house.

When I got home I went to my room and closed and locked the door and pulled the bra and panties out. I sat on my bed rubbing the fabric through my fingers, feeling how soft and slippery the nylon was and ended up stripping down and putting them back on again.
I ended up keeping the bra and panties and would wear them to bed at night like pajamas hand washing them in the mornings and hanging them up behind my bedroom door to dry. I loved the way the bra felt, a nice constant soft embrace. I was hooked.

[docrobbysherry]

No idea. Bras and panties aren't fetish items to me. They r simple utility items I use for dressing.:straightface:

I can tell u about my first real silicone breast forms and first silicone suit, tho! But, those may be as uninteresting to u as bras r to me!:devil:

[TiffanyMN]

My first bra was when I was 12 or 13 years old. I was babysitting for a friend of my Mom and on her bookshelf she had a copy of "Everything you want to know about sex but were afraid to ask." After the kids were all asleep I started looking through the book. I found a section on fetishes and it was talking about how some people find stimulation through articles of clothing like bras and panties. I had always been attracted to those types of items but never knew why. I went into the ladie's bedroom and tried on one of her bras. It was a simple, soft cup, plain white bra but it felt like heaven when I clasped the back and adjusted it into place. I immediately tried on a pair of her panties. I felt like I just discovered a whole new world and I knew it was something that just felt right. I put them both in my pockets and took them home. From then on I always tried to find a way to get access to bras, panties and other feminine clothing because I wanted to have a whole wardrobe of pretty things I could secretly wear when no one else was home. I ended up throwing everything away in my first purge when I convinced myself it was wrong to wear women's clothes and swore I would never do it again. It was the first of many such promises and purges. Still to this day, nearly 40 years later, I still have a special place in my heart and closet for simple, soft cup, plain white bras.

[HollyGreene]

When I was about 13 I was asked to babysit two girls who lived a few houses down the street. The mother was a very attractive woman and possibly my first crush.
The girls had a dressing-up box consisting of some of the mother's old clothes.
I had a rummage through the box and found a bra, which I tried on.
Of course it didn't stop there. There were dresses, skirts and tops in the box, and even a wig.
I couldn't believe my luck when the babysitting job became a regular thing.

[ronny0]

Boy in relation to others, I was a late bloomer. I was in my mid to late 30's had been wearing panty's and pantyhose (when I could pull it off) on and off for most of my adult life. Had come out to a few girlfriends about my love of panties & stockings / hose / pantyhose. One GF bought me a miniskirt and asked me to try it on. When I did, she suggested I needed something on top and gave me one of her bra's "to try on". Now this woman was like a size 0 and the bra she had me try on fit but was just a little tight??? Looking back, not so sure she didn't buy it for me.... Once I had it on she gave me some panties to fill it out, and suggested that it helped my 'look'. Anyway I was hooked, in a matter of a few months I went from a guy that loved panties and pantyhose to a guy that was now buying everything feminine from shoes to wigs and all in between. Since then it has all grown exponentially. For many years I have had 10 to 20 times more feminine clothing than male. I have maybe 1/5 of a closet with guy clothes, and a spare bed room filled with my female attire. Loving every time I have the chance to dress en-feminine.

[jacques]

hello Nancy,
Although I had tried on bras before I never really took to wearing one until I realized that that dresses hang better if I wore a bra and forms.
luv J

[Mermaiden]

Great stories! My first wasn?t until I was in my 30?s. When my wife was out I?d guiltily wear one of hers. I have clear memories of my mother?s bras, and still get a mild tingle thinking about them, but never borrowed them. In retrospect, wish I had and wish I?d recognized my inclination earlier.

[Krisi]

I grew up in a split level house. My bedroom was a half story below the living room and kitchen and everyone else had rooms above that. Everyone would throw their dirty clothes down from the kitchen into the hallway outside my door.

So, one day when nobody was home, I tried on my mother's bra and stuffed it with socks.

And that led to this! ;)

[SoBrooke]

I don't really remember the first time I tried on a bra but I certainly remember the first time I wore a bra with my silicone forms. This happened a couple years ago and I kick myself for waiting so long! With the girls on I feel so complete and at peace, maybe one day they will be real.

[Lori Ann Westlake]

I know the first bra I ever wore was my mother's. She was my only source of women's clothing when I was twelve or thirteen. And I know it was a white bra. Apart from that, I'm sorry to say I have no memory of the actual event, that glorious "first time" I put on a bra. Instead, I'm forced to reconstruct it in my imagination.

What I do remember is putting on my mother's skirt at twelve or thirteen, which was a huge trigger. After that I wanted to be completely dressed in women's clothing right away, naturally including women's underwear. The next thing I remember was being in the habit of dressing completely in my mother's clothes, the only ones available to me at the time, when I got the chance. There must have been a "first time" I did this, but I don't recall it--which I regret, because it must have been a wonderful feast of new tactile sensations. And logic tells me the first thing I put on was probably the bra. It might have been the girdle and nylons, but it made sense to start from the top down with the bra.

So there must have been that "first time I sat there naked and figured out how to put on a bra, slipping my arms through the straps, discovering it was too hard to fasten it behind my back, slipping it off again, then deciding I could fasten it in front of me instead, and sliding it around before putting my arms through the straps once more and pulling them up over my shoulders. And finally, stuffing the cups with rolled-up socks. (The practice of using rolled-up socks I do remember.) Then enjoying for the first time how it felt to be deliciously enclosed in a bra--before turning to the nylons, girdle and cool silky panties, the full-length slip, and the blouse and skirt. It must have happened that way. I'm sorry I don't remember it, that's all. The best I can do is enjoy thinking how it must have felt, the first time I put on a bra.

[Gilly68]

Like a lot of other ladies have said, my first time trying on a bra was one of my mum's when my parents were out shopping.

It would have been when I was 11 or 12.

My mum's bra's weren't sexy lacy things, but full coverage underwired and designed to give support as she had a big bust (F or G cup I think). Obviously, I had to stuff plenty of socks into it to fill out those cups, but once I'd done that, and slipped one of her dresses on, I felt like a girl, it was a wonderful feeling!

And I've got a thing for underwired bra's to this day, I love feeling the underwires pressing into my chest!

[Stefanie Taylor]

My mother made me tell the sa they were for me.

Do you think she did that to try and embarrass you enough to stop wearing them?

[ShelbyDawn]

I really don't remember the first one I wore but I do remember the first time I bought one in person, I stopped by the JC Penney near my apartment about 30 minutes before closing to pick up a few pair of panties I had noticed had gone on sale, less chance of being discovered, you know.
The lone sales lady in the area came up to me, "the other men that shop here really like the bras over here with those panties, would you like to try one on?" the rest is, as they say, history...

[Brenda Freeman]

The first bra I tried was my mom's after trying on her girdle and nylons several times. Loved how everything felt and looked but out of fear hid it very well. The first bra I bought for myself was way later in life. I called a Lingerie store and explained my interest in buying a bra and the owner had me come in just before they closed and she spent a lot of time with me explaining about bras and we tried several styles and she added breast forms in the mix. I left with 2 bras, on a later visit added breast forms and a wig. She was very nice and said she had a few male customers and told me about a crossdresser/tgirl group. She really opened the door to my future finally exploring my feminine side with out fear or shame.

[MarinaTwelve200]

My mom's---When I decided to do my FIRST full Dress-up at age 13-14, I rescued a white bra from the laundry basket. The rest of the family was out and I would be home for several hours by myself.---I had been doing Lipstick only for about a year, but I decided, all at once, to finally go "Whole hog" since I had the chance. Bra, girdle, panties, hose a slip and a housedress. The fit was good but slightly loose. I stuffed my cups with wash cloths. Makeup was eyebrow pencil and red lipstick.----Needless to say it was quite a HIGH! I also noticed that my hands kept hitting my "boobs" a lot, as my "personal space" image had not adjusted to my new contours. Even though the bra was just a B cup.(Coulda cheated a bit with the stuffing ;)

[Kris Burton]

I remember my first bra experience like it was yesterday - it was about three weeks ago. I guess I'm a "boob noob" (sorry, I thought I'd use that one first.) The CD encounters i had over the years always involved my wifes clothing but never included her bra...I liked the pantyhose and even the panties but somehow the bra although beckoning just seemed a mile too far.
Now that I have finally embraced this side of myself, I have bought all my own clothes, and that included a bra. I used the size guides provided at various sites, and it worked, so I find it quite comfortable. Although it seemed juvenile and silly, did the sock stuffing routine many of you mention you did as a kid, but it did fill it out and and looks OK for now. I get a good idea of the look I am after. Anyway this stuffing routine is not going to be around long...was checking out breastforms earlier today - expensive for the better ones but I know I'll be going there. Any suggestions?

[KymG]

My first would have been one of my mothers, although i dont recall it. Surely she would have wondered where it had gone?
In response to the prev post, go the breastform or breastplate route, its so worth it!

[Rachel Louise]

The first that I wore would undoubtedly have been my sister?s - probably around the age of 12 or 13. I used to ?borrow? her clothes quite regularly and while my initial interest was in her skirts and dresses, it wasn?t long before I wanted to experience wearing the appropriate under garments underneath.

The first bra I owned is unfortunately a much more mundane affair and was bought over the internet aged 17.

[kayegirl]

The first one that I wore would have been one of my sister's, thenot my girlfriend/wife's, The first one I bought for myself would be around 12 years ago when I got my first forms. Of course I got the sizing all wrong, so pulled on my big girl knickers and went to a large Marks and Spencer store, and got a proper fitting. The same was not at all fazed by measuring me, and gave great advice. Been back twice when I have bought new forms.

[AZashleemarie]

I had tried a few on over the years as a kid but my first time wearing one that actually fit right and was fun was in my early teens. I had wore panties and dresses before in secret but then they were mostly my sisters clothes she had outgrown. My parents were out of town and my second oldest sister and I were left alone for a weekend she must have been about 16 or 17 at the time. After a little drinking we were hanging out in the basement where the parents bar area was. I went into the utility room and jokingly put some panties on over my gym shorts (still remember they were black with sunflowers on them). I asked is this a cute look for me and laughed and my sister laughed and said I didnt know I have a little bro who is a crossdresser. That word scared me and made me think I was a freak and I was like I am just joking and pulled them off. She laughed and said "sure you arent". The beer fridge was located in the utility room where and she went to grab beers and came back with a two bras and joked they dont match your undies - I have always found it weird we call them panties but most girls call them undies. There was a purplish one and a hot pink one and she said lets see if they fit. I played dumb on how to put it on so as not to reveal my CD tendencies, she helped me put the pink one on and we went out into the garage and had a cigarette, then I was like okay i gotta take this thing off. She laughed at me and said imagine having to wear one all day. Nothing has been said since and that was many years ago - not sure if she genuinely forgot about it or just chalked it up to being dumb intoxicated kids. Part of me wishes I would have pushed for a full makeover, however I am glad I didnt as it would be awkward if she knew about my cding or mentioned it to any of my girlfriends in HS or college as we went to the same schools.

[NjJamie]

Get yourself to Glamour Boutique, the service cannot be matched! I still remember the 45 minutes sitting in my car trying to work up the nerve to step out but once I did it was awesome beyond words. I was taken to a semi-private room and got to look at a bunch of choices, wanted to try them all! The owner was incredible, measured me and had some ideas, tried a few and chose what turned out to be the least expensive. I have never been talked into the less expensive in any store! He asked what I wanted and was willing to sell me anything but in the end I got a nice pair of triangular silicone filled, D cup and have enjoyed them so much that I went back just a few weeks ago and bought another set in C (I am trying to blend as much as possible, making the most realistic profile is going to be key) plus a very beautiful blonde wig. It was such an awesome trip I headed right over to the nearby mall and waltzed into Macy's like I owned the place.
The store is discretely located on a major road, well stocked and very well run, I hope to go back this week just to say hello and look at a few other items.

[lingerieLiz]

I don't remember the first, but I did have a bullet bra and wore it out It wasn't hard to see the projection.

[Genifer Teal]

Never thought much about the feeling of wearing a bra. At some point I was putting on clothes and needed to enhance my chest. A bra seemed like the logical choice to hold something in place.

[KellyB]

First time wearing a bra was a bit of fun probably 20 years ago, someone had a Santa hat with braids so I jokily wore it and chucked a bra on over my jumper as Mrs Clause.
Wasn?t until years later I discovered Crossdressing and bought a twin pack of matching lingerie, ironically wearing one of those sets today

[Erin Lafleur]

Apart from looking down at my full breasts (love the summertime plunging necklines), I really enjoy occasionally adjusting my bra straps... feels so wonderfully feminine!

[Lacey New]

Like many of you, the first bra that I put on was my mother?s. I don?t remember exactly how old I was but I?m guessing that I was maybe 13 or 14. I was already ?borrowing? my mothers and sisters panties out of the hamper and I knew that if I timed things right I had about 30 minutes to myself in the house every day. So, naturally, curiosity got the better of me and one day I hurriedly stripped down and put on the bra with the panties. Well, you can all guess what happened next. So, I did it over and over as often as I could and loved it each time. However I did not buy my first bra until I was out on my own after college living in an apartment. And not only did I buy a bra, but many and lots of other pretty lingerie as well.

[kellyanne]

Almost 60 now, certainly my own first bras were at college when first living alone at age 22.
My first love affair with a particular bra was with the Wonderbra # 2635?
They were white & black had a simple cup with lace trim but the four way stretch material made you feel wonderful , like a pretty catalogue girl, with a pair of their panties.
If the sizing was a bit off the elastic properties would easily handle it which was not my experience with other brands.
Tried Playtex but found them well made but little stretch, Warner's was not bad but things like Triumph, Vanity Fair etc , did not work for me, these other brands always seemed to have more nylon and less elastane.

[alwayshave]

I don't remember my first, but my favorite is a black satin long line bra.

[Julie MA]

My first bra is still my only bra (except for one of my wife's, that I fished out of the trash; I hate to waste anything). Bought a pocket bra and forms, a wig, an LBD, garter, and thigh highs, about 6 years ago at the Glamour Boutique. It was my first step into the CD world. I still have, and wear all of the items I bought that day.

BTW. The bra has 3 hooks. I have always loved the ones with more hooks, and a wider back strap. Probably because I associate them with bigger boobs, which I also love. Oh, that Sears catalogue when I was a boy.

[Stephanie47]

Perhaps two stories. The first involved my mother's only black bra. Clothing way back then did not have any stretch. I foolishly tried the bra on only to snap one of the straps. I freaked out and put it back in her lingerie draw. I am sure she saw it. My mother and father probably suspected me, although they had no proof. They did their best to catch me wearing her clothing. They never caught me, but, I am sure they knew I was the culprit.

The second was about my first bra which was a Vanity Fair vivid red bra. I bought it at Christmas time which seemed a great time to fly under the radar when buying it. At the time my wardrobe on lingerie fit in a large gift box in the bottom draw of my armoire. My wife knew I liked the feel of nylon and together we had incorporated nylon nightgowns into the bedroom scene. She did not know about the bra until our three year old daughter yanked open the draw and then the lid to the box. She pulled out the bra which my wife found. That led to "The Talk" and ultimately to a life of "Don't Ask, Don't Tell." Her memorable comment was "Why would a man wear a bra when he had nothing to pack into it?"

[Jillian Faith]

Like so many of you the first bra I ever tried on was my mother's Playtex cotton bra that I liberated from the dirty clothes bin and stuffed with toilet paper to fill the cups.

[Dannigirl]

My first that I tried on was my sister's. Front close, beige. It fit perfectly, I was probably around 12 or so, my sister would have been 15. I think the first that I bought was a blue underwire t-shirt bra and a nice lacy bralette.

[KellyMichelle]

Like everyone else I was always borrowing bras from mom or if I went to my friends house I would look for their moms or older sisters.
But I count my first bra as the one I bought myself in the store 🙂
It was from JC Penny, a light pink bra/panty combo that had padded cups and the trim had pretty lace the whole way around it?I guessed and bought a 36b, it fit so good and I will never forget how good it felt wearing it 😍

[valerie anne]

I rather tend to remember the milestones in my bra journey.

Obviously, I tried on my mom's bras, but these were frumpy & didn't fit.

I remember much more vividly my first real bra - second hand from eBay - which actually fitted. I finally realised that the conventional bra wisdom, that you buy a bra with a band size 4" larger than your under-bust size, was a relic of cotton bras with no elasticity in the band or straps. I logged into the HerrRoom site to get better fitting advice.

My first milestone was that having ordered a 38 A cup, being the smallest, I actually could fill a B cup!

I am now up to a full C+, and it was another milestone to realise that I could not only fill a bra cup, but I am actually a lot more comfortable wearing a bra!

The underwired balconette with a 3 hook deep band has become my favourite for shape and uplift, but there have been some failures too.

Namely, strapless/cross-strapped bras just don't work. The cup shapes are all wrong, and the straps cut across the shoulders when going crossed. The same goes for halter necked bras.

In contrast, I have just got into bustiers, and I think these could become a positive milestone!

[giuseppina]

The first bra I tried was my mother's. All the elasticity was in the back band; I liked the feeling of it moving against my skin as I breathed.

[scoteller]

I think sports bras are popular everywhere, no matter whether you are in America or Asia. I love bras with orthopedic effect – I use them for my everyday runs https://thefluencewoman.com/best-posture-corrector-bras/. I always wear bras at work, but do not wear them at home. The only rule I have is to buy good quality lingerie. I avoid cheap goods.

[prene]

Having the beasts is what I like and makes me feel more feminine, not wearing a bra.

[Elise B. wren]

Well, my first bra wasn?t even an underwired one, since I was just starting to experiment with crossdressing. I didn't really intend to get any sort of cleavage, just an improvement in my ?female? silhouette, since I was wearing barely any shapewear, and I have a very masculine figure (being about 180cm tall and weighing around 100kg). As the color didn't really matter for that, I went for a simple beige bra, with elastics instead of casps. Then I paired it with a pair of adhesive push ups, in hopes that it would hold everything in place?

But yeah, things didn't go very well. I wasn?t able to build up enough volume on my chest, so it looked really off and awkward. I did some research only, looked up some brands of breast forms and planned my budget to acquire them, but I wanted to come up with an alternative to keep crossdressing until I could afford some nice forms. Well, this was the first time, but since it was a total failure, I don't count it. So, let me tell you about the first time I really felt comfortable and feminine while wearing a bra.

It was with a properly underwired bra my girlfriend helped me to buy, which I tested fitted with a few different ?fillings?. I first tested the classic socks, but yeah, they didn?t suit my body type very well. Then, i cutted out the cups from that first bra I've mentioned, and combined it with pushups, holding everything PROPERLY in place. I felt awesome, and my girl even helped me with a ?Cleavage? using some makeup tricks and such. This bra was also beige, but underwired and with actual clasps to better fit me. It was very comfortable, and the push ups/bra cups combo was a nice trick to create some volume.

Nowadays, i?ve managed to get a silicone breast form vest from roanyer. It's a C cup, but it increased my chest so much I had to buy a new bra. It?s a black one this time, with no wires and loose cups, so i can comfortably wear it with or without my forms on.

[Janine cd]

My first bra was my mom's. but of course it didn't fit properly, but I make due by stuffing it with tissue paper. The illusion was fantastic. By adding a panty girdle and nylons, I was able to achieve a really feminine form.

[Jane G]

This thread is invoking such happy memories. I can't actually recall my first time wearing a bra. But I still have the first one I ever bought. I never wear it these days, it is well past best, but I doubt I will ever bin it either.

[DTelia]

Can’t believe I’m sharing this. First one was my wife’s that she had me try…she’s bustier, but I’m not a huge chest, so I was able to get it around…had never really worn one or been interested. Wife purchased the next two (white and a black one) and sized them correctly. She put in some water balloons and she said she “strangely liked it”…I said zilch as to not draw attention.

[Al1986]

13 when i first tried on my moms bra
Got so ?hooked? into wearing one that I eventually got caught and smacked for it. Coming from a Muslim background it?s not something parents want to see. Eventually moved out at 18 and got better at hiding it and now years later still ?hooked?

[mollymulligan]

My mother was what I called a soft pack rat and saved while not everything, quite a lot and stored old bras and panties in my room thinking they'll be safely stored. Well, she didn't realize she had a crossdressing son and about the age of 10, I got curious and tried one on along with a pair of panties. Well, I was hooked from that time on. I will never forget it.

[Suzih]

I still have it, I was able to "Man-Up" and buy it at Walmart's . It's a nice Black Push-Up and I still like it.
Thanks, SuziH

[GraceH]

Like others here, the first bra I tried on was my mother's. I didn't have any sisters, so I was pleased when I grew tall enough to fit into some of her clothes. She was short. I bought my first one when I was in my late teens, after trying on one of my girlfriend's bras, which felt amazing-- it totally relaxed me. When my mom passed away a few years ago, I inherited her things and discovered we both wore the same size bra, a 36C.

[DanielleCD]

First bra I ever wore was my younger sisters. I was about 14 at the time, she was 13 and just starting to grow breasts. I have no idea what size it was but it fit.. and felt so nice. I would borrow her panties and bras on occasion from then on. I remember one night she had a girl friend sleep over. I snuck into her room and "borrowed" her friend panty and bra. Just felt so right tho it was wrong to do so.

[Rachael Fernandez]

My sisters are both younger than me and I could never fit into theirs, so, like many of us, the first bra I ever wore was my mothers. When I got to 12-13 years of age we were about the same size and they fitted me perfectly. The first bra I ever owned my wife bought for me. It was a plain skin toned Playtex Cross Your Heart bra. Not fancy, but it was mine. 40 years later I now own over a dozen bras. Many different styles and some with a matching panty. I love my bras and pantys. Quintessential women's wear, They help me feel so feminine.

[Ruby62]

I don't exactly remember where the/my first bra came from but I do remember keeping it in a wooden box along with rolled up tights.

[Amanda07]

I was a little bit later than some when trying my first bra. A few months after my wife and I got married. I was curious on what a bra feels like on me. So, when she was not home one afternoon. I put one of her bras on and from there I fell in love with them. However, my very first bra that I could wear around my wife came about 6 years later when I came out to my wife and told her that I like wearing women's clothing. She went out and bought me my first bra. She is a great wife and I am very grateful for her love and support with my crossdressing.

[IwishIwasTracy]

My first bra wearing experience was my sister's training bra. It was blue and had a picture of girl on it. She also had panties that matched the bra. From there I wore her other bras many times. I even hide one or two around the house for my use. I spent many nights babysitting neighbor kids and took advantage of trying on the mom's bras and even a dress or two. I know now that shouldn't have done that but hey what's a guy to do when you are 12 or 13.

Tracy

[Lori Anne]

My first bra was actually my sister's. I was small for my age, and she was tall for her age, so her clothes usually fit me.

[Amy R Lynn]

I was a young child when I tried on one of my Moms bras. I had to of been 5 or 6. Of course it was so big on me, it did nothing. I didn't buy my first bra until I was in my 30's though. I have spent decades denying who I am. I got a cheap bra for $20-30 from Wal-Mart. It wasn't anything special. However, that was the start to me finally accepting that this was who I am!

[StaceyJane]

Like most everyone else here the first bra I tried on was my mom's out of the laundry. I tried it on, stuffed it with socks, and really liked the way it looked.

[Alexis00]

I was a young child when I tried on one of my Moms bras. I had to of been 5 or 6. Of course it was so big on me, it did nothing. I didn't buy my first bra until I was in my 30's though. I have spent decades denying who I am. I got a cheap bra for $20-30 from Wal-Mart. It wasn't anything special. However, that was the start to me finally accepting that this was who I am!Next - bridal lingerie! Exciting!