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Your first bra
#1
Getting your first bra as a petticoated male or sissy is something that many of us remember vividly. With panties, there's basically a male equivalent. Even a dress or skirt isn't far off from kilts or tunics. When it comes to a bra, it is utterly female in that women are the ones who have breasts that need the support a bra provides. Granted, there are situations where a male may have need of a bra, such as genetic conditions or gynecomastia, but these are rare.

So how many of you remember getting your first bra? How old were you? Who bought it for you? When and where did you wear it? What were your thoughts and emotions that you had about it? Tell us your story...
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#2
Over the years I "acquired" (stole) a few bras and the guilt of actions just magnified the guilt and shame I felt about my feelings and my desire to be feminine.  As you might guess, these bras didn't fit and that didn't help my self image much either.

Ten years ago I served an online Mistress.  Mistress Sebrina was wonderful in the way she put me in touch with my place as a sissy and my natural femininity.  It's odd, but it was during my first session in diapers that she got me to confess my thieving ways.  I was embarrassed appearing on cam before her in my, now wet, diapers, and then felt as if a weight had been lifted from my breasts as I admitted my panties, my bras, my blouses and skirts were all stolen.  My eyes welled with tears, another new phenomenon for me.

Mistress instructed me to trash all my purloined goodies, so for the next three months my online sessions with her were in diapers.  Then came the day when she ordered me into the corner until I messed them!  I'd never done this.  I didn't want to do it.  An hour later I knelt before my computer cam as embarrassed as I'd been yet in my messy diaper, and Mistress told me she wanted me to appear in panties for my next session--panties purchased by yours truly.

I actually felt pride when I appeared before her in my (MY) new panties.  No diapers!  She inspected my shaved body, had me drop my panties and inspected there too, and we proceeded to cut up all of my boy shorts.  This is when I became a 24/7 pantied sissy.

So what does this have to do with my first bra?

Well, now that I was wearing my very own panties, Mistress gave me the link to a lady in Florida who makes training bras for sissies.  I sent my measurements and two weeks later appeared on cam before Mistress wearing my pretty satin training bra.  It felt so right, I felt so right.  The fit was perfect, everything was perfect.  The lace, the bow in the center, the gentle/firm sense of confinement.  No shame at all, just a warm gentle glow.

And it was my very own bra! 
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#3
Sissy Renee,

Thank you for sharing your story!!

Do you know if the lady in Florida is still in business and making bras for sissies?

Hugs;

Brieanne
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#4
One thing I didn't do is describe my own experiences with getting that first bra. While I wrote about it in the autobiography I put up, it still is a strong memory for me. I remember vividly that first night my mother had me dress up, sitting there afterwards in her clothes talking to her. She wore underwire bras, and I still remember the discomfort of having the wires digging into my ribs under my armpits. When I commented on it, she explained how the underwires gave better support for girls with larger breasts, and that the bra wasn't the right size for me. She joked at that point about taking me to get bras that were the right size so I could see how much more comfortable a properly fitted bra was.

Of course, that actually happened once she found out I enjoyed the clothes and was willing to dress again. Being in the department store, getting handed training bras, and then having to try at least one of them on was a nervous ordeal for me. Once back in the safety of home, putting it on and having my mother help.adjust the straps, hearing her talk about me being the last child to get my first bra, that helped me feel a bit more connected to the other children in our family. I had to admit, the proper size bra definitely was a lot more comfortable to wear, though you knew it was there constantly..

I wore a bra anytime I wore a dress or skirt. I know I found panties to be more comfortable to wear than boy's briefs, so I liked to wear them and often paired them with a bra even though I wasn't in a skirt or dress. The exception to this was when I wore panties to school and I had PE, the thought of wearing a bra and having to change in the locker room was scary. Too many bullies and danger that could come of that! I did wear a bra to school a few times once I had finished the PE requirement, but that was still a nervous time, worrying if someone might figure out what I had on.

I've worn a bra since, but it has been several years now since I last had one on. The last time I wore one was actually because I felt it necessary. My testosterone levels had gone to near zero and I was dealing with gynecomastia and had extremely tender breasts. The doctor suggested ibuprofen for the pain, and I read that a bra could help a lot with it, so I got a sports bra to wear. I found it a lot more comfortable and it helped control the tenderness better than any medication, so I wore it regularly.
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#5
(04-26-2017, 12:20 AM)Richardto Wrote: Getting your first bra as a petticoated male or sissy is something that many of us remember vividly. With panties, there's basically a male equivalent. Even a dress or skirt isn't far off from kilts or tunics. When it comes to a bra, it is utterly female in that women are the ones who have breasts that need the support a bra provides. Granted, there are situations where a male may have need of a bra, such as genetic conditions or gynecomastia, but these are rare.

So how many of you remember getting your first bra? How old were you? Who bought it for you? When and where did you wear it? What were your thoughts and emotions that you had about it? Tell us your story...

I got mine at Woolworth's at around age 12. It didn't fit, but it was silky and I loved the way it felt when I moved.

I think that all boys at about age 8-10 should be introduced to pantyhose and bras, and made to wear them under their school uniforms, and as formal wear for weekend events like shopping trips with their mothers.
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#6
Quote:I think that all boys at about age 8-10 should be introduced to pantyhose and bras, and made to wear them under their school uniforms, and as formal wear for weekend events like shopping trips with their mothers.
Conway has an excellent thought.  Training bras that actually fit are available at that age.  Alas, as so many of us are aware, it's much more difficult for adult sissies to get a perfect fit.  I'm a 42" band size.  Go figure. 

And to answer BrienneK, no I can't find the address of the seamstress from whom I got my first pretty training bra.  The key to that is "seamstress" though.  Sewing is such a nice activity for a sissy, and how-tos are available for everything including custom bras just as pretty as we desire.
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#7
Sissy Renee...I want to say that I totally enjoyed your story of your sissy training with your online Mistress.  I've had the privilege of serving and being trained both in "real life" and "online", and loved both, but I confess that "online training" is a true fetish of mine...I love everything about it...including reading of other's adventures...thank you for sharing it!

Here is a link of an online sissy training story...It's a rather long story, but one of the best I've read...you might enjoy it...

http://www.utopiastories.com/code/show_s...ecid/53554

As for my own "first bra" experience...I'll write of that soon...I need to get ready for work now...

Humbly,

sissy jamieanne
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#8
(04-27-2017, 01:23 AM)Conway Wrote:
(04-26-2017, 12:20 AM)Richardto Wrote: Getting your first bra as a petticoated male or sissy is something that many of us remember vividly. With panties, there's basically a male equivalent. Even a dress or skirt isn't far off from kilts or tunics. When it comes to a bra, it is utterly female in that women are the ones who have breasts that need the support a bra provides. Granted, there are situations where a male may have need of a bra, such as genetic conditions or gynecomastia, but these are rare.

So how many of you remember getting your first bra? How old were you? Who bought it for you? When and where did you wear it? What were your thoughts and emotions that you had about it? Tell us your story...

I got mine at Woolworth's at around age 12. It didn't fit, but it was silky and I loved the way it felt when I moved.

I think that all boys at about age 8-10 should be introduced to pantyhose and bras, and made to wear them under their school uniforms, and as formal wear for weekend events like shopping trips with their mothers.
Conway, who bought you that bra? Did you buy it for yourself, or was it your mother who got it for you. Since it didn't fit, I would assume you got it since most mothers would make sure you had a properly fit bra.
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#9
The local Woolworth's had a lingerie bin (one of many clothing bins) where off-brand merchandise was sold without packaging or labeling. They sold sneakers the same way.

I bought it myself using money I saved from my allowance. It was only about $3, pantyhose then were only about 99c. I really wanted some shoes but I had to wait until I was about 17 for that.

Thank God I grew up in a large city where there was some anonymity and (even in the 70s) some fetish publications that listed resources (and no one cared how old you were when you bought them).

(04-27-2017, 02:50 PM)Richardto Wrote:
(04-27-2017, 01:23 AM)Conway Wrote:
(04-26-2017, 12:20 AM)Richardto Wrote: Getting your first bra as a petticoated male or sissy is something that many of us remember vividly. With panties, there's basically a male equivalent. Even a dress or skirt isn't far off from kilts or tunics. When it comes to a bra, it is utterly female in that women are the ones who have breasts that need the support a bra provides. Granted, there are situations where a male may have need of a bra, such as genetic conditions or gynecomastia, but these are rare.

So how many of you remember getting your first bra? How old were you? Who bought it for you? When and where did you wear it? What were your thoughts and emotions that you had about it? Tell us your story...

I got mine at Woolworth's at around age 12. It didn't fit, but it was silky and I loved the way it felt when I moved.

I think that all boys at about age 8-10 should be introduced to pantyhose and bras, and made to wear them under their school uniforms, and as formal wear for weekend events like shopping trips with their mothers.
Conway, who bought you that bra? Did you buy it for yourself, or was it your mother who got it for you. Since it didn't fit, I would assume you got it since most mothers would make sure you had a properly fit bra.
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#10
Looking back, bras didn't enter my dressing and girly girl inner nature growing up. I know, that seems bizarre. What can I say? I was a different kid- na√Įve more than most.

I recall trying on one of my mom's bras once but I was more drawn to her nighties and slips. Well, panties and pettipants too, but with them I was scared I might leave, well, you know, trace evidence (I am such a girl- even now, some of this really embarrasses me).

Without sisters or other means to get an age appropriate bra, I just didn't go there. After all, I didn't have breasts.

What would have made a difference? Well, if my mom had insisted, I am sure I would have taken to bras. Or if I had developed breasts.

In truth, I never thought about breasts, mine or other girls. As I said, I was na√Įve. It wasn't until I was 23 that I first touched, and then saw, a girl's breast in person.

Had my mom put me in bras, it would have been terribly humiliating. And exciting beyond belief.

In petticoats and permed curls
Miss Kimmi
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