First bra

[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.

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!

[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!