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Your first bra
#1
   

   

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What was it like?


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#2
Buying my first bra was exhilarating! I was 21 and had purchased pantyhose a number of times. Buying a bra was the next step. Obviously a male purchasing a bra was like an oxymoron. Why would a male purchase a bra? "unless....." My heart was beating so hard I thought it would burst through my chest. I had measured my band size and fumbled around until I found one with the smallest cups. It was so embarrassing!
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#3
(05-22-2018, 03:12 PM)GinaV Wrote: Buying my first bra was exhilarating! I was 21 and had purchased pantyhose a number of times. Buying a bra was the next step. Obviously a male purchasing a bra was like an oxymoron. Why would a male purchase a bra? "unless....." My heart was beating so hard I thought it would burst through my chest. I had measured my band size and fumbled around until I found one with the smallest cups. It was so embarrassing!

Your memory made me smile Gina!  Your description of your nervousness while making your purchase is something many of us have lived through...I used to feel terribly conspicuous browsing through Victoria’s Secret or a department store lingerie department, but I’ve learned that my money is welcome in most places and the sales attendants are usually very welcoming and helpful regardless of one’s birth sex!
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#4
sissyjamieanne, Thanks, I think it's this "rush" that is part of the excitement/enjoyment. I've become more relaxed about buying Womens' clothing but there is always that feeling of shame or embarrassment lurking in my subconscious. The last time I purchased a bra I asked the sales Lady where the "24 Hour Cross Your Heart" bras were and She asked "Playtex?" and I thought, well of course, they're the only ones that make that brand, but just smiled she directed me to the display. I found the bra which was on sale and went to the check-out.
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#5
Mine was cheap, chinese made ordered online. But putting it on none of that mattered.
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#6
(05-24-2018, 07:55 PM)summersalmostgone Wrote: Mine was cheap, chinese made ordered online. But putting it on none of that mattered.

Putting on a bra really matters until you get - the hang - the knack - the dexterity to fasten things in the middle of the back unseen.
Well trial and error method - fasten the bra in the front and rotate about the waist and then pull up arms thru the straps and voila.
Have a front fastening bra is "Cheating".
Fortunately the SISSY male does not have the well developed super structure to manipulate out of the way in anchoring the fit.
And the enhancements are easy to insert since they are right up front.

Putting on tops can be an interesting first experience working around those enhancements with limited stretch in the material.

OK Sissy what is taking you so long getting dressed ?
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#7
My first bra was a flimsy sort that came in a panty/bra combination sold at department stores...I loved wearing it and felt so femme and sissy...I bought a couple of more in short order. I have never looked back...I wear a bra most days today, find them comfortable (properly fitted) and feel like something is missing if I'm not wearing one.
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#8
Mistress fitted my first bra.
It was pink lace with padded cups.
It was part of a set including panties and a beautiful suspender belt.

It was not the first time I had worn one for Her though.
To this day She insists that the first time I wear a new bra, that She fits it. She reminds me that it is a totally unnecessary item for a man to wear. therefore it is a symbol my submission to Her and Her dominance of me.
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#9
It is like Sarah Her Slut said it before: " therefore it is a symbol my submission to Her and Her dominance of me"

Ithink that is so right. A bra is at least for me, the most feminine clothing. Only female can wear it without shame, it is so natural for women. Therefore if a male or a sissy wear a bra or is forced to wear one, it is absolute a symbol of submission-

sissy caja
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