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My first time wearing a bra: How did you try on a bra for the first time?

144 Posts
53 Users
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Posts: 1025
Lady
Topic starter
(@marieclaire2)
Noble Member     London, United Kingdom
Joined: 4 years ago

I was 11 or 12 when I noticed girls at school starting to wear bras.
I got curious and tried on my sister’s bra on the sly (Mom’s bras were too big for me) and enjoyed the experience … a white training bra with a bow.
Over time I tried on her other bras until I could have my own bras.

 

 

How did you try on a bra for the first time?

 

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143 Replies
32 Replies
Baroness
(@annaredhead)
Joined: 11 months ago

Famed Member     Cornwall, United Kingdom
Posts: 1837

@marieclaire2 It was one of my sister's when I was 14. I also put on one of her dresses that same time.

It was white and lacy, I couldn't work out how to fasten it behind me, so I fastened it in front and turned it round.

Hugs,

Anna xx

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@annaredhead
It's really cool to remember the details of your first bra.
Thank you very much for sharing your experience!

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(@coloradog1)
Joined: 3 years ago

Honorable Member     California, United States of America
Posts: 281

@annaredhead same thing with my first time lol. I could never get the damn thing clipped behind my back

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(@geniv_cd)
Joined: 8 years ago

Reputable Member     Minneapolis, Minnesota, United States of America
Posts: 260

@marieclaire2 My first was one of my Mom’s, it was padded and I fell in love with the feeling and the image of my having breasts! Couldn’t wait for my next opportunity to wear a bra from that point on! Happy Woman Face

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@geniv_cd For many, mom's lingerie drawer is Heaven on Earth!

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Lady
(@ria)
Joined: 5 years ago

Reputable Member     Saskatoon, Saskatchewan, Canada
Posts: 330

@geniv_cd Thanks for kindling a memory just like yours. I still look forward to every opportunity to wear my bra.

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(@lauren114)
Joined: 2 years ago

Noble Member     Delaware, United States of America
Posts: 1209

@marieclaire2 I started with my sister's bras.  The first one I tried was a stretch bra that was similar to a sports bra.   The next one was a pretty floral print bra with lace trim.  This one had hooks in the back and I managed to do them behind me.  Not easy but I got it done!   This second one started my love of pretty lingerie which still exists to this day!

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@lauren114 I love pretty lingerie too!

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(@devonne)
Joined: 2 months ago

Active Member     Freedom, California, United States of America
Posts: 4

@lauren114 Isn’t amazing that something like trying on a bra , panties , sexy dress can form a life long passion. For me when Iam dressed it makes me feel sexy , it has all my life . Used to feel guilty , but the hell with it , was told it was part of my DNA , so learn to embrace it ! DeVonne

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(@lauren114)
Joined: 2 years ago

Noble Member     Delaware, United States of America
Posts: 1209

@devonne I'm with you....It's part of who I am so I have just embraced it and I'm a happier person because of it!

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(@devonne)
Joined: 2 months ago

Active Member     Freedom, California, United States of America
Posts: 4

@marieclaire2 I found a bra hanging in one of the changing rooms for our pool . Iam in my later teens at the time , but the feel of wearing it put me over the edge and it became a life long passion for me and to this day in my mid 70’s , dressing gets my motor running. DeVonne

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@devonne Very good!

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Lady
(@briana)
Joined: 2 years ago

Estimable Member     Florida, United States of America
Posts: 67

@marieclaire2 Hi Marie,   as a bored kid at home in the mid1970s, i was about 10or11.   i was looking at the Fredericks of Hollywood ads in mom's Cosmo mags.   for some reason, i felt like trying on her bra.  and panties...and L'eggs...and her slip.

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@briana Very good!

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(@briefgirl)
Joined: 2 years ago

Active Member     Palm Springs, California, United States of America
Posts: 5

@briana Yes I remember looking at my aunt’s Fredericks catalogs she had in her magazine rack. Once when I was about 7 or 8 I tip toed into her bedroom while she was outside and opened her dresser and found a lacy bra sitting on top. I knew how bras were to fit from the catalogs and began slipping it on. I had almost figured it out when I heard her coming back into the house. I panicked and yanked it off as fast as i could and stuffed it back into her dresser. Now I have lots of pretty bras that actually fit me.

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Lady
(@stephanieann)
Joined: 2 months ago

Prominent Member     Northern California, California, United States of America
Posts: 526

@briefgirl 

Beautiful Amazing Story,  not unlike how most of us started ,  a woman's dresser draw or hanging in the bathroom drying .. 

Hugg

Stephanie 👠

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(@elizabethjean)
Joined: 2 months ago

Active Member     Fryeburg, Maine, United States of America
Posts: 6

@marieclaire2 I saw my mom's bras and pantyhose on the bed one day, and they really attracted me. She was a sixties mom, and most of her lingerie nowadays would be considered retro. She had the lace full-coverage bras, slips, full briefs, garter belts, and stockings—until pantyhose became the thing. I began wearing her bras and everything else at about twelve. When I was older and my growing stopped, I chose a 36C bra to wear during my escapades. I still wear that size today. I bought breast forms that complement my average size...not too small or too big...realistic for me.

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@elizabethjean What an amazing experience!

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Lady
(@stephanieann)
Joined: 2 months ago

Prominent Member     Northern California, California, United States of America
Posts: 526

@elizabethjean 

    That was a wonderful amazing experience you had growing up , especially retro style is Awesome ...

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(@cdashley)
Joined: 5 years ago

Noble Member     Oshawa, Ontario, Canada
Posts: 1489

@marieclaire2 Well like most I was around 10 or 11 years young.  Curious after trying pantyhose on I went into my mom’s room and put on a white with lace trim bra and stuffed it with parts of her panties.

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@cdashley When it comes to crossdressing, one thing always leads to another!

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(@cdashley)
Joined: 5 years ago

Noble Member     Oshawa, Ontario, Canada
Posts: 1489

@marieclaire2 It sure does Marie Claire. I agree 100 % as it’s like anything and it keeps evolving with time. What started with trying on my sisters pantyhose to a fully dressing , jewelry, perfume , wigs , shape wear , makeup , panties and bralette daily crossdresser. And I love of second of it. 

 
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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4016

Posted by: @marieclaire2

How did you try on a bra for the first time?

For the first time?

As a naive teenager during what could charitably be called roll-playing games. I got to stuff the bra of a classmate who had admirabley sized breasts for her age.

It wasn't a turn-on for me, though, and I never did it again until two years ago.

 

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@harriette So interesting!

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(@marleneroberts)
Joined: 5 years ago

Honorable Member     Allentown, Pennsylvania, United States of America
Posts: 575

@marieclaire2  I was late to the party. I did not try on a bra until I was 65 or so. We were dressing to go out to dinner. My wife had two of the same bra and two of the same panties. On a whim we decided I should wear a bra and panty. We called it his and hers. We giggled a lot at the restaurant. From then on I always wore a bra and panty when eating out. I also wear them when at home; I am doing so now together with a camisole. Best, Marlene.

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Lady
(@stephanieann)
Joined: 2 months ago

Prominent Member     Northern California, California, United States of America
Posts: 526

@marieclaire2 

 🍒🍒  Don't you wish that's how you start as a 11 -12 years old girl just starting to bud, and you & mom taking you out to get your first bra, as mom & daughter ..  💓

What amazing wonderful experience then having  lunch  that would be . 💓

Every Girls Dream

Hugg

Stephanie 👠 

 

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(@closetcelt)
Joined: 3 months ago

Estimable Member     Kentucky, United States of America
Posts: 89

@marieclaire2 My first bra I tried was an old girlfriend back around 14ish, she left it at my house, and figured why not. I absolutely loved it

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(@sometimessteffi)
Joined: 2 years ago

Estimable Member     Reston, Virginia, United States of America
Posts: 64

@marieclaire2 

It was mom's bra.  I must have been 11 or 12, but old enough to be left home alone.  I put it on the girls way, putting my arms through the straps and hooking it behind my back.

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Lady
(@chellygirl)
Joined: 1 month ago

Trusted Member     Florida, United States of America
Posts: 23

@marieclaire2 I was about 12 or 13. I was home from school supposed to be sick. I went sneaking around my mom's drawers and found matching bra and panties. I put on a on skirt and top i had found as well. I pranced around all day dressed up. Before my sister got home from school I put everything back. I didn't think about being careful and just kind of through the stuff back in there. Not long after my mom got home she came down stairs and wanted to know who was in her room and why her drawer was open and why she had clothes on her closet floor. My sister obviously denied it. So did I. But my mom knew it was me and told me she better never catch me in her things again. 

 

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(@kimberlyannvictoria)
Joined: 3 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 480

@chellygirl I had a similar experience, I had often worn my Mothers and Sisters clothes and wasn't very careful doing it. She approached me and asked me about wearing their clothes. I denied it but she knew what I was doing, Also loved to wear their clothes when I was home sick.😊

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Lady
(@julie51)
Joined: 2 weeks ago

Estimable Member     Chicago, Illinois, United States of America
Posts: 59

@marieclaire2 

Great Topic
My first time wearing a bra was just a couple of years ago I felt the need to try one on. I learned how to take my measurements and ordered a bra online now I have a drawerful of them. I love the feeling of being feminine.

Julie

 

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(@katherineboesemann)
Joined: 5 years ago

Reputable Member     Cape Town, Western Cape, South Africa
Posts: 192

@marieclaire2 I have a feeling that this question has been put before - and also that I once responded to it.

The first time I wore a bra was at the beginning of one of many pasionate weekends when my late wife helped to get me dressed up.

I was probably still deep in the "fetish phase" and had already had a long relationship with panties.

Over time, my inner woman yearned more and more to don all the other accoutrements of femininity (and to assume various traditionaly female roles).

Now my wife (being an enthusiastic supporter) participated and guided me farther along this path, doing my make up and letting me have various items of her clothing and jewellery.

I remember looking at my freshly made up face in the mirror of our vintage dressing table and being delighted at seeing there a woman looking back at me.

It was she who got me into one of her bras - stufed with scarves, etc. - so that I could present a female profile.

She asked me; "How does it feel to have breasts?" and I felt an incredible rush - a sense of being completely a woman and accepted as one.

There was also at the same time a mild sense of panic: a bra is not something easily concealed or pulled off.

There was a vague sense of being "trapped" in female form - there would no longer be just a light flirtation with the feminine or flittiong back and forth between being a man and secretly presenting as a woman.

I could ramble on but will leave you all with that idea.

I must say that my wife's band size was one measurement too tight for me and during her lifetime I also felt the tightness of her bras but since her passing I have acquired bras of my own (correctly sized) and feel wonderful when I wear them (filled now with silicone breast forms) under my blouses and dresses.

 

Love,

Katherine

 

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Posts: 28
Duchess
(@carlalayne)
Trusted Member     Roseville, Minnesota, United States of America
Joined: 2 years ago

For e - it was on a whim. I only have brothers and girl's underwear were a bit of an attractive mystery. I had a same-age female friend who offered to show me hers - which I accepted. After showing me she said that I should try on a bra to get a feel for it. I did and when it was hooked in place I was hooked! Quite exciting. Even now, as a senior, I enjoy the feeling of wearing a bra. 

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@carlalayne What a wonderful experience!

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Posts: 2075
Duchess
(@rozalyne)
Famed Member     Shrewsbury, Shropshire, United Kingdom
Joined: 3 years ago

Hi Marie, 

I was about the same age as you when i tried my first bra on ,it was my older sisters bra, I'd tried her panties on and one of her slips so i progressed to trying on one of her bra's, wearing a bra gives you a feeling like no other, I sometimes wish i could wear one all the time, 

Hugs Roz X 

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3 Replies
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@rozalyne Crossdressing makes us want to try more and more new things!
I also wanted to wear a bra every day!

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Duchess
(@rozalyne)
Joined: 3 years ago

Famed Member     Shrewsbury, Shropshire, United Kingdom
Posts: 2075

@marieclaire2 

I know how you feel Marie, after I'd tried my sisters lingerie on i so wanted to try one of her dresses, then her skirts and tops, I couldn't try her shoes on though we had different size shoes, 

Hugs Roz X 

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(@devonne)
Joined: 2 months ago

Active Member     Freedom, California, United States of America
Posts: 4

@marieclaire2  I like that you said it makes us want to try more new things .For me if I was single dating a mature  trans woman would be and exciting adventure for my self . DeVonne

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Posts: 193
(@jessicacynthia)
Reputable Member     London, United Kingdom
Joined: 2 months ago

I first wore a bra when a girl put a bra on me as a joke. I think I was in my early teens,

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@jessicacynthia What an interesting experience!

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Posts: 812
 Leah
Baroness
(@leah63)
Noble Member     Minneapolis, Minnesota, United States of America
Joined: 7 years ago

I was about 13 or so, found a sexy pink 34C bra that I had to have. the rest is history

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@leah63 I love my lacy underwire bra too!

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Posts: 124
(@kpl58)
Estimable Member     Virginia, United States of America
Joined: 4 years ago

I was 11 or 12 and tried on one of my mother’s bras I found in the laundry hamper.  I would do that relatively frequently, until I was caught by her one day.  Although I was very embarrassed at the time, I don’t remember her making a big deal out of it as I suspect she knew what I had been doing all along. 

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@kpl58 These subjects are still taboo!

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Posts: 485
Lady
(@cherylt)
Prominent Member     Honesdale, Pennsylvania, United States of America
Joined: 7 months ago

I first wore mom's panties at about age 5 and shortly after that tried her bra as well. 

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5 Replies
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@cherylt You experimented too young!

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Lady
(@cherylt)
Joined: 7 months ago

Prominent Member     Honesdale, Pennsylvania, United States of America
Posts: 485

@marieclaire2 Why do you think I was too young? I'm certainly glad I didn't wait until I was 50 to find out how wonderful it is to be a woman.

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@cherylt I just wanted to say that you started earlier than us, who started at 11,12,13 years old.
Well, the important thing is to enjoy every moment!

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Lady
(@cherylt)
Joined: 7 months ago

Prominent Member     Honesdale, Pennsylvania, United States of America
Posts: 485

@marieclaire2 I suppose I was a bit precocious in that respect. First came mom's panties and then the curiosity just got the best of me and off I went. 

By that time I had already wanted to be a girl though I had no idea what it meant other than the long hair and pretty clothes. Just wish things had been as open then as they are now. I'm sure my future would have looked completely different.

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(@clarissa2)
Joined: 4 years ago

Honorable Member     jutland, Denmark
Posts: 415

@cherylt I also started around the age 5, I simply asked my mom to borrow some underwear to play being a fine lady and I borrowed her girdle, bra and stockings. Elastane was not invented back then so it was really a nylon feeling and I looooved it and I somehow felt aroused it just felt so good. I never found out if she knew what was really going on. It was just wonderfull. That's how my lifelong crosdressing started.

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Posts: 7829
(@aliceunderwire)
Illustrious Member     Near Burlington, Vermont, United States of America
Joined: 5 years ago

Hi Marie,

I was 11 or 12 and my mom worked so I had an opportunity to look in her dresser.  After several years I outgrew hers and decided to buy my own.

Alice

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@aliceunderwire Very good!

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Posts: 2036
Baroness
(@ryanpaul)
Famed Member     Outer Eastern Suburbs Melbourne, Victoria, Australia
Joined: 7 years ago

My mothers at about age12. A couple of years later I had a "thing" about strapless bras and cut the straps of a blue one of hers. She did not say much but  I got "the rounds of the kitchen" from my Dad.

He later told me, (the paragon of 1960's Australian "male culture" that he was), that if I kept on wanting to dress in women's clothes, "the boys in the pub would call me a queen". aka homosexual.

Back then, given "pub culture" was at its paramount, at least in his eyes, there was no worse fate that could come your way.

Obviously a/. It did not work b/. thankfully the above no longer applies and c/. other than lunches, I rarely "drink" in pubs anyway.

I should explain, my dear old Dad's way of remembering "Charlie from Bill" was to ask "where does he drink"

Caty.

 

 

 

 

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@ryanpaul If even today society still views certain subjects as taboo - and reacts violently to them - imagine back then.
Parents often react not only by trying to enforce their expectations of their children but also by trying to protect them from social intolerance.

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Posts: 2111
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

I was also about 11 or 12 when I first tried on my mother's bra and panties. It didn't take long before I also tried on her garter belt and stockings as well as one of her dresses. It felt wonderful wearing her things even though it was for short periods of time. I never got caught, or if she noticed she never said anything. A few years ago I came out to my wife and I now have my own femme wardrobe and truly enjoy being my femme self even though it is only at home. 

XOXO
Suzanne

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4 Replies
(@dovemtn2016)
Joined: 1 year ago

Honorable Member     Tucson, Arizona, United States of America
Posts: 313

@cdsue Suzanne, being a woman is absolutely wonderful. At the moment, you are the last posting, so ...why not try to put into words the amazing emotions we all feel as we experience our own sense of being a woman.

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Hostess
(@cdsue)
Joined: 5 years ago

Famed Member     Delaware, United States of America
Posts: 2111

@dovemtn2016 I will have to give that some thought - thanks for the idea 

XOXO
Suzanne

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Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@cdsue Very good!

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(@kimberlyannvictoria)
Joined: 3 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 480

@cdsue Yes once you start wearing Moms clothes you cant stop and you want more!!!

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Posts: 3445
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

I was at about the same age. I had been trying my sisters clothes for years and when I saw them wearing training bras  followed the trend using a little padding. Shall we say things'developed' from there.....

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@ab123 Very good!

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Posts: 370
Lady
(@sf)
Prominent Member     SoCal, California, United States of America
Joined: 3 years ago

Bras, I have mixed feeling about them.  Mostly from the opinions of the women that I have been around all my life.  I was raised by women, married a woman and none of them (including many of my female friends) really have never spoken highly about their bras.  

Having been "tainted" I have tried a bra a few times and have mixed feeling.  They are fun to wear on occasion, but I can see the gals thoughts about having to wear one all the time.

An additional detractor is wifey, she knows I crossdress but draws the line at me wearing a bra, at least for now.  And I will try and respect her wishes.  

Have fun...   Staci... 

 

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@sf I love putting on a bra, but after a while I also like taking it off. But then I feel like putting one on again!

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

Most of the setails are lost in the fog of time. I do not recall in great desire to rry things on. As I recall one day I just decided to wear all of mom's thi gs and dressed head to toe, so a bra was included. It was fun and I thi k I did it one other time and that was it. For a good ten years I ne er thought about wearing anythi g femme, though I always liked nice lingerie on my girlfriends.

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@jjandme Your experience is very interesting!

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Posts: 86
Lady
(@donnacdwi)
Estimable Member     Wausau , Wisconsin, United States of America
Joined: 3 years ago

I don’t recall wearing a bra until I got married. I had enjoyed other under garments like pantyhose. Loved them. But I don’t recall bras up to that point.She was at least a D cup . Her chest size fit me perfect. I would stuff those babies full of something. I so enjoyed how I looked. It gave me such a feminine figure.

Now I wear bras all weekend.

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1 Reply
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025
Posts: 480
(@kimberlyannvictoria)
Honorable Member     milwaukee, Wisconsin, United States of America
Joined: 3 years ago

Hi Marie. I started wearing my sisters and mothers clothes when I was 12. I am not sure who's bra I wore first. But I do remember the first Bra I bought. I was a 34 A cup with a cute bow in the middle that i bought from Sears when I was 16

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5 Replies
Lady
(@marieclaire2)
Joined: 4 years ago

Noble Member     London, United Kingdom
Posts: 1025

@kimberlyannvictoria

The first (own) bra we never forget!

 
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(@kimberlyannvictoria)
Joined: 3 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 480

@marieclaire2 Yes I always remember buying it. It was one of the first female things I ever bought for myself. I remember being very nervous going to the cashier and paying for it. But looking back I am sure they had seen other boys buying bras for themselves

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Lady
(@stephanieann)
Joined: 2 months ago

Prominent Member     Northern California, California, United States of America
Posts: 526

@kimberlyannvictoria 

Your first bra is always so so special,  especially. ( . I was a 34 A cup with a cute bow in the middle that i bought from Sears when I was 16 )  lovely cute teen bra,  With cute bow in the middle,  mine was about the same but with a cute rose in the middle ,  it  felt so amazing  !!

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Lady
(@stephanieann)
Joined: 2 months ago

Prominent Member     Northern California, California, United States of America
Posts: 526

Such a  special special moment ,  in time a gurls first bra ,  something you never forget, the amazing awesome feeling wear your first bra,  even the cute little bow in the middle, 

Special moment,  also your first match bra & panty set !!!

Beautiful 

Huggs 

Stephanie 

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(@kimberlyannvictoria)
Joined: 3 years ago

Honorable Member     milwaukee, Wisconsin, United States of America
Posts: 480

@stephanieann It also was a very intense experience for a young gurl like I was to purchase my first Bra, I can only imagine what the lady ringing up my purchase thought of me at the time

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