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Your first bra
#11
My very first bra and many after that were bought for me by my wife. Up until that time I had just been wearing panties and pantyhose as part of bedroom fun but wearing a bra changed everything as it now became more about exploring my feminine side and things really took off from there. While still part of bedroom fun other things were soon added, dresses, skirts and blouses and of course high heels. But it was getting to wear a bra that had the most effect on me, putting on a woman's most intimate item seemed to instantly shed anything masculine about me and introduced wonderfully feminine feelings that I began to crave. My first bra was a Christmas gift, it was somewhere between lavender and purple and had black lace upper cups and was underwired. It came with matching panties and garter belt so this also became my first time wearing stockings. Great post, everyone remembers their first bra whether you are male, female or those inbetween.
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#12
Quote:everyone remembers their first bra whether you are male, female or those in between.
Oh my, Maid Jennifer.  You've just made me think of something.  Remember back when the girls in your grade started wearing bras?  They were becoming different people, alien beings shrouded in mystery in our midst.  And oh, what fascinating creatures they were.  Sitting behind one of these strangers I'd known since first grade, the impression of her bra strap against her blouse, the temptation then the action as I grasped the strap and snapped it!

I wonder if Jo Anne G. remembers that?  Looking back I can see what a disgusting act it was, an example of adolescent male behavior that shames so many of us here.  This earned me a trip to the principal's office and 5 well deserved swats from Mr. H. (back in the day when spanking was used in schools routinely), but it kinda added to my status among the boys.  I wonder how my life would be different had the punishment been more apt?  Today I'd prescribe a female authority figure wielding the paddle, bottom bared, and in front of the class instead of in Mr. H.'s private office--and then I should have been required to wear a bra to school myself.

I wish I could visit Jo Anne today, kneel down in front of her, and beg her forgiveness.  I finally understand.  I know now that first bras come when girls are undergoing their myriad changes to womanhood, changes I didn't understand then, and still don't completely.  Intellectually I get it, but I can only try to mimic their precious gift I so casually ridiculed way back when.  If only . . .

I recounted my own first bra experience above, but this is really part of the same story.  It's about what bras mean to me.  They are the exterior indicator of transition to womanhood, a journey I longed for for so many years.  And repressed..
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#13
[quote pid='6340' dateline='1493482314']


I recounted my own first bra experience above, but this is really part of the same story.  It's about what bras mean to me.  They are the exterior indicator of transition to womanhood, a journey I longed for for so many years.  And repressed..
[/quote]

You have touched on a wonderful point here, that of when a girl begins to develop and it is a right of passage into womanhood. It's different for us of course but conversations with my wife about her first bra were very enlightening for me. As she puts it she was a late bloomer, all her friends wore bras long before she did and she says she felt cheated and it really bothered her that she didn't have a bra. That is until she all of a sudden went from nothing to a full D cup in what she remembers as leaps and bounds and more than caught up to her friends. For us our bras are maybe not rights of passage but it is a passage nonetheless that leaves much of our masculinity behind.
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#14
That's why I think accepting the embrace of a bra is a far deeper recognition of femininity than wearing panties, Maid Jenny.  To me it means (or meant) a real commitment to my emerging, flowering girl so long hidden inside.
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#15
Surprisingly I can't pinpoint my "first bra"...and ironically, I've come to absolutely adore bras!

I have some early bra memories...firstly, the flimsy, sheer bras that used to come with the bra and panty sets...I had a few of those, but they were really just decorative for the most part...no support, no underwire, no padding...

The first real bras I remember owning were about 20 years ago...my wife and I were shopping for panties for me, and she found them...it was 2 wonderful bras with sewn in gel pads...and they felt wonderful...for the first time in my sissy life, I felt like I had real boobies!

Today, I love bras and wear one everyday...I can't imagine life without a bra!

Humbly,

sissy jamieanne
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#16
I overheard two colleagues talking a while back, one commented that she always looked forward to getting home in the evening and taking off her bra. How different to me!  I cant wait to put mine on! I would have loved to say so and let the cat out of the bag.
I also remember sitting behind girls at school and see the intriguing bra straps although I dont think I ever pinged them as some of the other boys did. I wasnt brave enough to touch girls.
Its long time ago now but I think my my first purchase was not a bra but a basque. I must have developed a fascination for them as a teenager. I remember seeing a lovely one in BHS, white with pink trim, delightfully feminine. After eyeing it up from a distance and checking the queues I finally picked it up and literally having cold sweats as I took it to the cash desk.
Its so long ago I cant remember the thrill of putting it on but Im sure it was wonderful to wear something so girly.
Longing to serve women
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#17
Bras are incredibly exciting when first experienced, and even today are so critical to feeling truly feminine. At a young age you could sort of justify mentally the notion of panties, because boys and girl wore "underpants", and they have made bikinis for men for many years - thus, not so daring. Though nobody would mistake anything in my collection as "men's" underwear. But a bra is different altogether. So classically feminine. Slipping your fingers understood your bra during masturbation for nipple play, is almost too exciting to think about!
Once experienced- too hard to turn away from.
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#18
My Mistress/Wife gave me my first bra. I had been wearing panties 24/7 and she came home and said three was a panty/bra sale on and she loved the pink panties she brought me so she just had to get me the matching bra. I was a bit taken aback at the time but with her "coaxing" I did try it on and soon began to love wearing bras.
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#19
(05-07-2017, 02:40 PM)insearchofme Wrote: My Mistress/Wife gave me my first bra. I had been wearing panties 24/7 and she came home and said three was a panty/bra sale on and she loved the pink panties she brought me so she just had to get me the matching bra. I was a bit taken aback at the time but with her "coaxing" I did try it on and soon began to love wearing bras.

I have always felt that when a woman gives you a bra and especially if it's your first one her intentions are often to get you to experience your feminine side in ways she feels you may be too embarassed to admit to her you'd like to try. That doesn't necessarily mean she intends to fully feminize you but in a way it does mean that she is testing you to find out how far both of you will go with this. I suppose it's kind of like "truth or dare" and for my wife and I this is pretty much how it all began.
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#20
(05-07-2017, 03:23 PM)Maid Jennifer Wrote:
(05-07-2017, 02:40 PM)insearchofme Wrote: My Mistress/Wife gave me my first bra. I had been wearing panties 24/7 and she came home and said three was a panty/bra sale on and she loved the pink panties she brought me so she just had to get me the matching bra. I was a bit taken aback at the time but with her "coaxing" I did try it on and soon began to love wearing bras.

I have always felt that when a woman gives you a bra and especially if it's your first one her intentions are often to get you to experience your feminine side in ways she feels you may be too embarassed to admit to her you'd like to try. That doesn't necessarily mean she intends to fully feminize you but in a way it does mean that she is testing you to find out how far both of you will go with this. I suppose it's kind of like "truth or dare" and for my wife and I this is pretty much how it all began.
I just wish I'd gotten my first bra from my Mom.  Oh, hers was the first I ever wore, but that was me sneaking around and being bad, and it just added to my feelings of guilt and shame that stayed with me for so many years.  How I wish she'd seen my need (perhaps she did but that's another issue) and taken me shopping for my very own training bra.
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