10 Years Old With My First Bra. My Mother Was Happy ...my Sister Was Thrilled ...and I Was Addicted.

I was 9 and had been dressing at home as a game with my sister ...and mother, for about a year. The perfect American family. Home schooled, no neighbors, and a lonely 11 year old stepsister who wanted a girl to play with. I had a wardrobe full of girl's clothes and was being taught to be a young lady along with my sister. But i still remember that first bra being held out in front of me as if it was yesterday..I was scared and embarrassed as my mother let it dangle from her hand. it was pink with lace trim and tiny little hearts all over it with a little bow in front. I stared at it as if that single garment acknowledged the loss of my uh, boyhood. I tried to argue against it but my mother left little choice since she had bought it for me so i could be like my big sister. She did say if i wore it through the weekend end and still didn't like it, I could take it off. It was slightly padded and she took her time adjusting it to my chest and shoulders. But when my mother slipped a pastel blue top over me with a matching cotton skirt, my whole body burst into goose bumps. I could see the bra right through my top in the mirror and i thought i would feint from embarrassment. By the end of the weekend ...I felt more like a girl than I had ever had before. My mother was happy ...my sister was thrilled ...and well, I am probably still embarrassed enough to say ...I was addicted
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21 Responses Mar 28, 2012

Perfect family

You never forget the first time. Lovely story and the bra sounded amazing

Hi Kaylee, I remember when, like you, Mommy got me my very own bra with just a tiny bit of padding. I can't really explain why, but the tiny bit of padding, which just gave my profile the merest hint of a bust, was so exciting! I just loved having a little bit of what my mom would call "a figure." Of course, unlike you, I did not go on to live outwardly as a girl. My girlfriend recently bought me a bra, with gel insetrts, which I absolutley love. They really give me the feeling of having my own Breasts. What about you? What size bra do you wear? Have you developed anything up top? If so, how? Xoxo Sandy

What a lovely story, Sandy, and what a great mom you have, buying you your first bra to improve your figure. But even better is now with your girlfriend buying you another bra with gel inserts, do less! I would love to hear more about this. ;-)

After I left home to go to college, my dressing basically stopped. Althoug part of me wanted to stay at home as Mommy's little sissy forever, she was brave and mature enough to send me out on my own. I really grieved the loss of my feminine mentor. Years later, when I met Emily, with her encouragement, I started again. The big question was, should we tell Mother? How would she feel? Would she be happy for me, or maybe jealous that I'm a sense, she had been replaced? Emily handled it (as she does most things). She started by dropping very subtle hints. For example, the three of us would be out to dinner, and Mother would apply her lipstick, and Emily would say, "Oh, that's a lovely shade. Sandy, what do YOU think?" I would blush furiously and answer in the affirmative. A few more times like this, and Mother finally pulled me aside one day and asked me whether Emily knew about my feminine side. I told her everything, and it is been great joy to me that the two loves of my life take pleasure in scheming together to make me more feminine! (And yes, I know how lucky I am!)

Thanks for your response Kaylee. I'm SO curious - when you started to develop Breasts in your mid teens, did you know why? Do you know why even today? Was your mom giving you hormones? If so, were you aware that that's what she was doing? I assume that since you were dressing as a girl full time at that point, that you would have been happy about it.

Back to me, yes, it's been really interesting to me to see how over the years, certain things really intensified my feelings of femininity. Of course, every sissy boy remembers the first time he slipped on a pair of panties. But as you have stated, the first time I put on a training bra, it was literally transformative. The gel inserts were like that as well, because they made me feel as if I literally had Breasts (a feeling I love!) I also felt that way the first time my mother put lipstick on me. Wearing heels for the first time was another amazing, intensely feminine experience, the way it changes your whole posture. And the first time I shaved my legs (with Mother's help) and put on hose, was up there as well.

I'm a sissy, and you're a girl, but the thing we have in common is our love of all things feminine! Xoxox

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The first time I tried on one of my mom's bras I was hooked. I loved the way it felt and the way I looked.

This is an area that has not been sufficiently studied. We know that chromosomes are binary, ie, Xs and Ys. And we used to think that gender was the same. Now of course, we know that gender is more like a spectrum. I wonder how much brain chemistry and hormones vary along with how people consider themselves. And I wonder if that chemistry can literally be altered not, say, by taking female hormones, but by events themselves. Can mommy putting a bra on you literally cause you to produce more female hormones?

Interesting thought dear. My doctor described it to me back when I started hormones as like a balance beam. Some are at the ends, being predominately female or male, but most of us are somewhere in between. From the results of the tests she ran on me it seems I was very close to the balance point. So a low dosage of female hormones pushed me well into the female range.

I have a related question re hormones. I have seen lots of pics of trans girls with their boy parts. (I suspect many of the one where they are large and erect are photoshopped.) Obviously, with a large enough dose over a long enough period of time, the penis shrinks and becomes, um, non-functional. Does the balance beam analogy apply here as well? Ie, is it possible to take female hormones and yet keep your functionality? Was it important to your wife that you retained your ability to perform?

Good questions, dear. Of course I can only speak of my experience, but even though I have been on female hormones for quite a while I am still functional. It takes longer for me to react (love cuddling and playing even more) but given time I am still functional. Of course thanks to my urethral relocation when I do climax it comes out from between my legs, So I am the one, not my wife, who has to get up and wipe or suffer wet sheets. As far as my wife is concerned she loves it!

Urethral relocation!! I have never ever heard of that! Where was it located to? Why did you do it? To feel more like a girl? It seems very, very close to just going all the way and having SRS. Curious to know your thoughts.

It created a new meatus (pee hole) between my legs. It makes it so I pee like a girl which makes me feel more female. And for me it was a good alternative to SRS which I can't afford.

Wow! Do you continue to ********* through your penis, or is that through the new hole as well? So, the only reason for not getting the full SRS is $$?

My ********* comes out between my legs too. My wife loves this because when we make love I am the one who has to go to the bathroom and clean myself or suffer with a wet spot in the sheets.
Money isn't the sole reason though it certainly is a significant part of not getting full SRS. Another is that I never hated my parts down there so I don't feel incomplete as a woman by having them. And another is that my wife loves that little difference too ... referring to it as my "super sized clitty." ;-)

I am fascinated! And so glad you have a lovely and understanding wife!

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I also enjoy wearing bras. And as missymotherandme said, it's more for the feeling of arousal. Everytime I wear women's clothes, I imagine and try to have a perfect and complete female figure.

Anyways great story.

Speaking of Imagination and arousal, my girlfriend and I have a fun game. When she finds something she likes for me (a dress, a pair of heels, whatever) she buy the same thing for herself. Since I am not passable, most of my dressing remains at home. But she will wear one of my outfits when we go out, and she looks fabulous. Instead of looking at myself in a mirror and getting depressed by the reality, I look at her and imagine it's me!!

Well, you know, I have always struggled with the problem so common to many of us - the image in the mirror does not match the image in my mind. For some 'girls,' what they actually look like is not a concern. But for me, it matters. If someone told me I could get dressed and made up and look like, say, Andrej Pejic, I would be out on the town in a heartbeat. But I hate the idea of going out and looking like some drag queen. (Btw this is why so many of my FM stories involve me as an adolescent - before puberty kicks in, I can still pass as a pretty girl. With Mother's help, of course!). Anyway, I am (obviously) blessed to have a beautiful and totally open-minded girlfriend, and so I think my "solution" to my appearance is quit elegant, thank you! I look at her, sitting across the restaurant table from me, wearing the same dress and shoes I have hanging in my closet, her makeup perfect, and I think to myself, "Wow, I look great!"

Imagination fuels the dressing and desire of so many of us. I like to look at a cute girl on the beach or on the street and imagine that's me at that age (when I too could have pulled off passing). Perhaps this is why I remain fixated on being a pre-20 year old girl as well.

We cannot all be as lucky as Kaylee and have our outer beauty match our self-image! Thank God for the internet! As I have told you, Kimmie, I imagine you looking just like your avatar! To me, that is really who you are (gorgeous curls and all).

It's nice to have friends like Kaylee and you who can make my day with one sweet and positive comment. Just like this one. I am blushing!

I suspect that Kaylee has such good friends because she is the kind of person who is smart and sensitive enough to appreciate her friends!

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Hi Kaylee,
I am not surprised at all that your first time wearing a bra left such an indelible mark on your psyche. Of course, your ongoing saga, and unique perspective, is having lived what so many of us have fantasized about. Of course, the reality is always more complex than the fantasy, but still, what you describe is well, exactly as i would have pictured it! i put my first bra on when i was around the same age. It was my mother's, and i was home alone. But i basically had the same feelings you describe - almost a sense of electricity going through me, and this unmistakable feeling that i had somehow instantly become more feminine simply by putting on this garment. i loved the feeling of it 'wrapping' me, almost as if it were protecting me. and i loved standing sideways and looking in the mirror, imagining that i had a ladies' figure. You have written previously that all of these little milestones - pierced ears, tweezed brows, your first panties - all left an indelible mark on you, that you could remember all of these things, but not, say, the first time your rode a bike. The same is true for me, and i would venture, many others. and i would guess it is because of the intensity of the experience. Two more things: first, i wonder if being feminine ever had a sexual component for you. For me, the intensity of the experience was greatly compounded by my feelings of arousal. (In my own amateur psychology, i suspect that difference may be what separates transgender from sissies - the sissy feels a sexual arousal from being feminine, and the transgendered person simply feels that this is what should be.) Second, i mentioned that when i first put on a bra, i looked for curves in my profile. My FANTASY, especially when all the girls around me started, was to sprout my own cute little breasts. But i was not presenting as a girl. What about you? ANd i guess the more general question is, even without breast envy, did you go through male puberty? That must have been incredibly difficult and confusing for you. As you know, i am new to both EP and to you, and i have been reading your story piece by piece. So, i apologize if you have written about all of this and i have not gotten to it yet! xoxoxo Sandy

When I started hormones to feminize my body I now refer to that as my second puberty, but this time I got it right ;-)

wow, Lee! A big step that most of us don't take! May i ask, how old were you? Did you also get implants? Anything else? FFS? i see your name is TGhubby. Are you married to a genetic woman? Did you take hormones before are aftermarriage?
Some of you may be aware, there is a big controversy raging over an Op Ed published in the Wall Street journal condemning SRS, and in particular, blockers and hormones in pre-pubescents. If i were to have gone down that road, i certainly would have loved to have been able to start before male puberty kicked in.

Yes it was a big step dear, but with my wife's support and encouragement hormones were a step I am glad I took. And yes I am married to the same wonderful woman and I am satisfied with the breasts I've grown so no I haven't gone for implants.

So happy for you! She must truly be a special lady!

Thanks dear. Where I know I am lucky to have a wife who is not only understanding, but supportive and encouraging, what makes it even better is that she feels she is lucky to have me.

Not sure if you have been following the adventures of Andrej (now Andreja) Pejic, but there are some interesting parallels (and differences) in your stories. Andrej, of course was known (and labelled as such on the cover of NY Magazine) as the most beautiful boy in the world. He was clearly androgynous, but seemed to be getting increasingly feminine in dress and mannerisms over time. He seemed to be completely free of secondary male sex characteristics (no facial hair, for example) but exhibited no signs of female hormones (ie completely flat chest). To me, there was something erotic about seeing this gorgeous, gorgeously made up face on, well, a boy's body. Like you, he just seemed to be a boy who had been very low on male hormones and kind of skipped male puberty altogether. For those of us in the sissy community (I define a sissy as a genetic boy who loves to be feminine but has no desire to become a biological female) Andrej was a real hero(oine). He would go out, wearing a dress, beautifully made up, looking gorgeous, but did not hide the fact that he was a boy. He was our fantasy come to life, which of course, makes the fantasies more compelling and intense because you think, "Yes, it COULD happen!" Anyway, as you probably know, Andrej recently announced that he recently had SRS. Of course, we are happy for her, and wish her nothing but the best. But for me, and I suspect for many others, there is this odd sense of loss. How do I put it? He was the most beautiful boy in the world, but now is just one more pretty girl. Oh, one more thing. He also disclosed that while not taking female hormones, he has In fact been on blockers since he was thirteen! So, mystery solved. He was not preternaturally feminine, he had some help.

Awesome ... mystery solved!

Hi Kaylee. Yes, I believe his mother was involved. I do believe that his brother and father were also always supportive of him. And yes, I think Andrej has changed her name to Andreja. As I've said, for me, mixed emotions. I am happy she has "found herself" and now feels complete. But we girlish boys who do not want SRS will miss the one of us who was called, "The prettiest boy in the world."

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My family has never known and I only have brothers so I can only imagine how you felt.

It is addicting isn't it! Absolutely nothing screams "girl" more then the mere act of putting on a bra!

Another lovely story Kaylee...!

I wish my mother had been as encouraging and supportive!

wot a lovely letter you were so lucky mum an sis look after you how nice sleep in sisters old nightie can i ask were their times when you got aroused as sister dressd you :):)

You touch me deeply. I love my brother, my mom and being a woman. I started playing dress up with my brother when I was about 9 and Gil was about to turn 7. We lived in a small house, very isolated Gil and I shared the same room, and were about to move him to the couch. In this case, I started it. I imagined that his PJs were rough and got him into some of my old nighties. Since I did most of the laundry I don't think Mom knew, until one day Mom was doing laundry and asked where Gil's P J s were. I had no wriggle room and had to tell about the nighties. We had a long talk and wanted to know if it was OK with Gil. I told her he liked it and she sat there thinking then said it would save on cost of clothes when we had plenty of my nice old ones.

She told me to put him in my old panties with his nighties. I asked, HER nighties. She said she was not ready to say that yet, but asked me to refer to him that way from now on. So I rold Jill that she would wear panties under her nighties now as did I! There was a big NO! but when night came I just put the panties on her. She whimpered and grumbled but finally said they felt nice. The next morning she we stumbled into the kitchen to breakfast and Mom asked how we were. I think she had a troubled look on her face. I said "She's wearing her panties today." Jill asked if she had to and Mom said Just do as your sister says. she lifted Jill's skirt and said my sh sh she looks nice.

Not another thing was said that day and she wore the panties all day. Mom moved out all her boy things and refilled his cubby with my outgrown things.

I have lost Jill. But I helped him be happy, till then

love that story really nice x

My sisters used to dress me up like a Barbie doll & I secretly loved it ! I loved it when they would slip their bras & panties on me & put a dress over my shoulders felt so good !!! Now I have my own big collection that I love to wear all day long whenever I want which is all the time!

I was 6 or 7 & they were10 & 11 if memory serves me right Looking back on that those were good times !

We're I live there is almost always someone home and If I get some time I never get time to hide it and wash of my makeup before there see so its really hard for me althought when I was young my cousin would put me in her princess dresses and I just loved it and when I grew up in p1 we would have play time and not being aloud to dress up with the other girls drove me nuts all I could do was play with toy cars

Kaylee, You are so lucky to have had a childhood that most of only dream about. I wish my mother would have realized what I was doing when I asked her if I could try on her girdle. She just chuckled and said "OK", but it never went any further with her. I did tell her that I liked the way it felt on me and the way it made me feel. I don't know if she ever realized that I was wearing her stuff after that, but I did tell her years later after my first wife and I split up. She didn't seem to be bothered by it, but I got the feeling she didn't want to see me dressed up. You Mom must be an amazing person, don't forget to Love her today !!!

what made you start dressing up first

U are so luckily I only wish my mum could be like that u have the life I dream of

Lucky Girl....

The process of learning began from there and now u are a person who is well versed his own sexuality and mind.. That is the advantage of good begining..

i wish my parents had found out about my crossdressing and that i had been strong enough to tell them. I truly envy you.

Public ridicule i imagine?

I too was 10 years old when i tried on my first lingerie, panties, hoes, powder, lipstick, shoes, etc etc. I never told my mom till this day that i did. I Have not until recently thought about doing it everyday again. I have help from a woman friend to try it again. I am home all the time alone. I have an income to live on that gives me privacy. Yes i will be your friend.

Wonderful that your mother and sister were both so supportive<br />
Hugs<br />

i love this i love putting a bra on and a thin top so it can be seen thank you

What a wonderful story, kewlee. It brought both memories as well as goose boomps reading it. How wonderful for your Mother, but also for your sister, to have you! I can certainly understand where after that weekend you were addicted ... who wouldn't be?