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    Anonymous
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    Hi Girls,

    For me bra is the most feminine piece of clothing item in everyday wear. So how did you get your first one?

    When i was around 13 i wore my first bra which i took from my sister. That’s more out of curiosity and excitement of doing it than anything else at that time. It was difficult to me to clasp it and somehow i managed it after some initial struggle. I was checking myself on mirror and my mum entered the room and she saw me.

    I didn’t know how to react luckily for having the best mum in the world instead of shouting at me my mum hey Alex sweety what are you doing?. I didn’t answer her but she came to me and told it doesn’t fit me well so i need to remove it and we i want to wear somrthing from my sis i will have to ask first.

    She bought me a new bra few days later but i didn’t feel the same excitement as with m sister’s one but i really enjoyed.

    After all this time both my mum and sister are really supportive of me and even now buy me bras so i didn’t have take their’s. For who i am today i would like to thank them.

    What about you?

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    • #651486
      Anonymous
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      I used to wear  my sisters bras when I was young she never found out but as I got older I gain the confidence to buy my own from the shop I love my bras I feel so feminine when I wear one

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    • #651433
      Requal Joanne
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      When about 10 years old, my sisters were clearing out their wardrobes and clothing was in a bundle waiting to be put into the rubbish so I took a bra and panties and tried them on.   What a wonderful feeling was had.  I then took another bra, panties, corset, stockings and full slip and hid them in my room.   From then on I dressed in my sisters clothing at every opportunity till leaving home at 16 years.  The next bra I owned was purchased by me at age 32 years and I have owned several bras since then.

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    • #651398
      Jasmine
      Registered On: June 8, 2022
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      I got my first bra I think around 14 to 16 at a store that ain’t around no more called super 10 and it was a white lace bra underwire I believe 36d and given that I have always been roughly 6’2″ since about the age of 13 and I had have a fairly wide chest it worked out perfectly for me even though I just guessed before that I started with my mother’s like most of us did and just kind of worked off of that basis to figure it out from there

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    • #651047
      Anonymous
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      I had tried on sisters and mothers. But I was in late twenties when I first bought one. I went off the deep end after not dressing for years, and bought a maids outfit at a store that sold sexy lingerie among many other items. The sales person was kind and suggested that I would need something to hold things up, she offered to measure me for a bustier. I was shaking and hyperventilating and blushing as she took my measurements and then supervised the fitting. The second time I had gone to a store in mall. I think the sales person just guessed at my size and guessed too  small. I was driving a long distance, wore it stuffed a bit. Felt daring in the moment even though it was dark. After four hours of wearing it….couldn’t wait to get it off….(lost in same purge).I might try a nice soft bralette soon, other than that just vintage ‘cupped’ slips which are lovely too!

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    • #650394
      Debbie Burns
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      Registered On: February 19, 2022
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      My first one was my mothers I would wear her lingerie when I was home alone loved the feel of it on me. I would fill the cups with socks so they weren’t wrinkled. Then I got a bra from a clothes line in the neighborhood that fit perfectly it was nylon and unlined from a nice looking girl that went to the school I attended she was a few years older to have had some breasts but not too much As or small Bs.The next was a bra I borrowed from a girl friend I did give it back and then borrowed another a few times.I would take them from the laundry and then put them back another time. Then at 16 when I was able to drive I went nervously and shaking to the store and bought my first one and some nylon bikini panties,red faced and could hardly talk made my way to the check out and completed my purchase. I think no I know the sales girl knew they were for me.

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    • #650367
      Stephaniewy
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      Registered On: September 24, 2021
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      My first bra was one my wife was throwing away.  I fished it out of the trash, still in good shape.  I slipped it on and knew I had arrived at a certain place.  Not sure what that place is, still figuring it out.  Since then I have come out to my wife and she is very supportive and has bought me a few nicer bras but her old one is still my favorite

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    • #650152
      Jenny Liu
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      Registered On: January 27, 2022
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      It was my mom’s.  Started with stockings, slowly progressed to panties, then to bra, and then the whole nine yards.

      I bought my first bra when I was seventeen at a lingerie store.  Initially, I was kind of embarrassed and didn’t know how to approach it.  Then, I thought of an idea: I was involved in a “school play” and as one of the organizers, had to purchase the “props”, which included panties, stockings, and of course BRA.  From there, I got bolder each time and now it’s just part of my routine.

       

      Jenny

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    • #650125
      Aurora Borealis
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      Registered On: October 25, 2021
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      My first bra was one of my Mothers when I dressed in her clothes once. She was a bit taken aback. LOL! Aurora B.

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    • #650122
      Brielle
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      I borrowed bras from my sisters or my mom. When I had my own place, I had a depatrment store credit card, and they’d send mail inserts for clothes, etc. in the bill. This was years before the Internet and there weren’t even cell phones yet. Anyway, there was a sale on bras, so I got a money order and sent it in. I think I got two, and had them for several years until I was about to marry my wife, and I purged everything before she moved in.

      Brie

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    • #650119
      Sabrina Sistera
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      I started wearing a bra and panties when I was 14 . It was my mom’s underwear ,I was going through her dresser drawers . When I found her bra’s and panties .the smell of the lingerie ,turn me on so I tried them on. My sister walked in on me ,are you wearing mom’s underwear . She closed the door and came back with some of old panties and bra’s and two dresses . She threw them at me ,hear you Sissy boy and stay out of my room. So my sister gave me my first bra.

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    • #650118
      Sabrina Sistera
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      • I started wearing a bra and panties when I was 14 . It was my mom’s underwear ,I was going through her dresser drawers . When I found her bra’s and panties .the smell of the lingerie ,turn me on so I tried them on. My sister walked in on me ,are you wearing mom’s underwear . She closed the door and came back with some of old panties and bra’s and two dresses . She threw them at me ,hear you Sissy boy and stay out of my room. So my sister gave me my first bra.
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    • #650108
      Lisa Leigh
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      Registered On: April 20, 2022
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      My first was from my sisters throw away, out grown pile. It wasn’t great, very stiff cotton bra, a 36B but it became mine. Since I had an idea of how to sew i brought the cup size down as to make it better fitting for my flat chest. I had that bra for years. I did enjoy my mother tricot bras better. They didn’t fit as well, but much softer.
      The first bra I bought was during Christmas 2012. No one cares if your a guy looking to buy woman’s intimates during the holidays. Just ask for a gift receipt! Bought three different types of bras that evening. (Also matching panties the saleswoman said I should buy as well.) First was a front enclosure white T-shirt bra ( became my go to bra) second was a black and ivory satiny bra (my sexy bra) and third was a racing back white bra with front enclosure. All were in 38B, all fit well except the racing back was a bit tight.
      I have had several purging events during my time and all of those are long gone but have fond memories.

      • This reply was modified 2 months ago by Lisa Leigh.
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    • #650104
      Donna Cooper
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      Not proud of it, but I have to confess that I stole a bra from the woman I used to babysit for her kids when I was probably 14 or 15. It was lightly padded size 34 B and had a small embroidered rose on the front band between the cups. I still remember the slightly perfumed scent of it and how much I loved secretly wearing it in my room at night.

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    • #650100
      Anonymous
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      Well, mines kinda funny. I’m a swimmer. Not elite level at all, but decent and can hold my own. Anyway, I swam in high school, and 2 of my teammates were Belgian. One of them had been gifted a “water bra” during a Christmas party my team held. Well, his senior year he decided to attempt a new tradition, one which died instantly as I didn’t swim my senior year. That tradition? Gifting the same water bra again and again. The thing is, I got that thing home and would often wear it at night, often while wearing my mom’s swim wear as well. I had that thing for 6 years and don’t remember what happened to it after I got back from the Navy.

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    • #650088
      Sandy Honey
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      My Mom found some of her panties and a bra in my room and she asked me about them. I told her how I liked wearing them and she told me it was wrong to take her things. A few days later I found some nylon panties and a white cotton training bra in my dresser. She bought me my first bra that actually fit me. I was allowed to wear them at home but not out. As I got older and bigger she would replace them. I do love wearing bras!

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      • #650143
        Lara Tucker
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        What a cool mom!

      • #650121
        Raquel Smith
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        That’s awesome.

    • #650007
      Natalie Jones
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      I unknowingly purchased my first bra when I was 18. It was more like a bralette and it was a very bright pink.
      How did I purchase a bra unknowingly? Well I had been buying my own panties and babydoll nighties for about 2 years. One Saturday evening I headed to Kmart, not for girlie things but maybe the complete opposite a case of motor oil! But before I could leave the store I at least had to walk past the lingerie department. There close to the isle was a discount rack with nighties. I had been wanting a long nightgown and there on the rack was this pink gown draped over a hanger . It was my size and it was like $4. With out looking any further I put it in my cart along with a few other panties that were on sale and headed to the checkout with lingerie and motor oil.  When I got home ( I lived with my parent who would always go to our shore house on the weekends and I’d have the house to myself) I pulled the nightie off the hanger and out fell a pair of panties. As I opened it up I discovered it really wasn’t a long nightie but a matching bra and panty set with a floor length cover up. It was adorable! To my surprise they all fit including the bra. It had cute white lace trim and the whole outfit just felt so wonderful. I would sleep in it like it was a gown. Made fairly cheaply it didn’t hold up but that was the beginning of my love of bra’s and bralette’s

      Natalie💋💋💋

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    • #649916
      Pattie Obarito
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      and then the first that FIT…my first that I was able to keep was from mom, 36C.  lots of room in it.  felt good on my back.

      then one of my classmates moved away.  on a lark, I went thru the house they moved out of.  lo and behold, his sister left one in her chest of drawers, a B cup.  first chance I got, tried it on.  BOOM!  perfect fit!

      long gone now, over 40 years ago.  fond memories.

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    • #263982
      Paula F
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      I wore my sister’s outgrown dresses, shorts, tops panties etc for several years after becoming aware of my feelings about being seen as a boy, all in secret of course.  My mom finally got her first real bra’s with cups and all, and I ‘rescued’ her trainers from the donation box in the laundry.  I had tried them on a few times but didn’t wear them long each time.  But once I had my very own bra’s, finally, omg I was in heaven.  Those trainer bra’s just made me feel so much more girly than the panties and dresses and all the other things.  It is hard to describe how they made me truly feel, but it was definitely good about myself.

      PaulaF

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    • #263922
      Donni
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      Registered On: December 17, 2018
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      My wife gave me my first bra many years ago. I still have it mosty because it means so much to me. 💕

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    • #263919
      Jin Crocker
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      Inherited it from my older sister. She noticed that my breasts were coming in and said something like: “If you are going to go out with those bouncing around, you need this. Sometimes at least.”

      She has been letting me wear her clothes ever since.

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    • #263803
      DeLora
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      I recently purchased my first bra. It took a lot of hunting to find a size that I though was appropriate.

      I had never felt the need for a bra, seeing as I don’t have anything to put in it, however, I figured it would help with the shape of some of the tops I had recently purchased and I did want to try a bra.
      I ended up getting a very plain gray 34B. The cups have foam padding, so hold their shape even without being filled with anything. I am not considering breast forms at this time.
      I do like this little bra and it does help me feel a little more femme.

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    • #263782
      Amanda Sanders
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      First time wearing a bra-10(My mother’s) though I tried on one of her skirts at 4

      first time owning a bra-17. Went into Woolworths,took a guess on my size and bought two bras (black and pink) and two pair of matching panties. The cashier looked like she was going to laugh. Got home,tried them on-perfect fit so I didn’t care if she was going to laugh or not

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    • #263096
      Breanna Leigh
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      I can’t remember…….

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    • #263027
      Erica Gutkowski
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      Registered On: December 21, 2019
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      For me, there were a few “first” bras.

       

      I had been curious about women’s underwear for a number of years when I got the courage to try on my mom’s bra at age 10.  From the very first time, I knew this was something I wanted to do more of.  Whenever I was home alone, I took the opportunity to explore this new-found joy.  After graduating from college, I ordered my very first bra from a catalog.  (Yes, life existed before the internet, lol.) The wait for the bra seemed like forever.  But when it arrived, it was worth the wait.

      Several years after that, when I knew I wanted to take things more seriously, I went to get professionally fitted for a bra.  Sure, I was nervous, but leaving the store with my first two real bras was exhilarating.  Now I can’t imagine a day where I don’t wear a bra for at least a little while, if not all day.

      As Jessica noted in her earlier post in this topic, “When I can feel the straps around my chest and shoulders it makes me feel, not just feminine, but complete.”

       

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    • #262577
      Stephanie Bass
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      Registered On: October 14, 2017
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      <p style=”text-align: left;”>I remember my first purchase very well. Went to Sears with my size and style (longline 36C back then)on it found a sales associate and gave it to her and said I need to find this for my sister. She located it and I made my purchase. She most likely knew it was for me</p>

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    • #262561
      Patty Phose
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      Registered On: May 7, 2016
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      I’ve been wearing pantyhose and heels since I was 4. Ever since then I had dreamed of wearing other things too. Bras being one of them. Unfortunately those were not available to me or no doubt I would have been wearing them.

      I would look in department store catalogues, dreaming of wearing all the pretty clothes I would have someday. I also learned about sizing and how to measure.

      When i bought my first bras, I knew what size I needed. I went to a store, picked out what I liked in my size, bought them, took them home and put them on, along  with my silky sheer to waist pantyhose, sexy stilettos, pretty panties, short dress, pretty hair wig and some makeup. I was living a lifelong dream and fantasy.

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    • #262253
      Cynthia Hughes
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      Registered On: March 12, 2019
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      It was not until after my wife and I had bought a house that I finally went out and bought one.  It was a fairly simple unlined, wide strap, wire-free Wonderbra that we bought at a (Now closed) large chain Canadian retailer.

      We were so nervous and had no real idea of what we were looking for nor did it cross our minds to even measure me first before heading out.  It was kinda a crapshoot and we just went with something along with her size range and walked away with a 44D which actually fit perfect.

      Kinda funny because while cleaning out stuff the other day I came across this bra again in my wife’s drawer as she stole it from me.  It’s pretty haggard looing now but I can’t bear to part with it just yet.

      Bra shaooping is way easier now that I have measurede myself and no longer need my wife to hold my hand when I go out.

      Cynthia

       

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    • #262252
      Diane Marie Rakers
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      Registered On: August 18, 2019
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      I agree. A bra is the MOST feminine item of clothing. When I put on a bra I feel I have been magically transformed into a woman. I love the feeling. I am wanting to be a woman so badly.

      Okay, my first bra. I measured myself with a household tape measure and it said 40 around the chest. Good so far. I don’t want to be a woman who announces herself with big boobs, so I went with a B cup. I also don’t like reaching around so I selected a bra with a front closure. A very good decision.

      Amazon, of course. Locker delivery, of course.

      I have worn both Vanity Fair and Bally. Both very nice.

      When I can feel the straps around my chest and shoulders it makes me feel, not just feminine, but complete.

      I love all of you for openness and respect for each other.

      Jessica

       

       

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    • #261994
      Ruby Smith
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      Registered On: October 17, 2019
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      My wife bought me my 1st bra. She is the best and has helped me acquire a lot of my femme items.
      Hugs, Ruby

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    • #261987
      Anonymous
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      With no female relatives to “borrow from, I didn’t have any bras until after my dressing re-booted about 3 years ago, and I ordered them from Amazon. Later, I ordered from The Little Bra Company, but never found a decent fit until I was fitted at Dillard’s last Summer.

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    • #261979
      K Swim
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      I got mine many years ago through eBay…NEW of course, not used. Although swimwear was my preference then as it is now, I was still discovering myself to see if other types of women’s clothing would give me the same satisfaction. Since I eventually came to accept that I am not a huge bra or panty fan, I eventually got rid of it.

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    • #261946
      Pattie Obarito
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      Registered On: December 25, 2019
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      Found in a pile of used clothes put outside by a neighbor—-covered in snow.   Took it inside, and brrrr!    I tried it on again and again.   Mom must have found it because it disappeared from my (obvious) hiding spot.

      not too long after i took one of hers and found a much better hiding place.

      from this distance in time she had to have known but never mentioned it.

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    • #192462
      Anonymous
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      Not proud of it….but I have to confess that I stole one of my sisters bras.

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    • #192442
      Sarah
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      Registered On: May 11, 2019
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      My wife gave me one of her bra’s for the first one as we are close to the same size.

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    • #185194
      Donna Richards
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      Registered On: January 11, 2019
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      Thank you Erica for posting this. I went into a local retail store (Meijer). I was so nervous! I just guessed what size I was and hurriedly grabbed a 36 B cup off the rack. That same day, I also purchased some lace panties, a pair of skinny jeans (where I also just guessed at my size), along with some makeup. I then went over to the the self checkout lane and waited until it wasn’t very busy. I scanned my items as fast as I could, and got the hell out of there before someone recognized me. Since then, it’s become much easier.

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    • #184866
      Maria
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      Registered On: November 29, 2018
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      Technically my wife gave me my first bra, back when I first introduced her to this side of me but I was only using clothes in the bedroom and she learned to like it. Not so much now, complex dadt/share a little every now and again, at the minute. Its nice but in her size so not really for me but I was only wearing her stuff at this time.

      First bra I actually bought was from amazon, double padded wonder bra, it was too tight on my back but felt and looked amazing I had to keep it. Still my favourite and I have warn it enough to stretch it out so now so it fits.

      First bra I bought in person (drab), and the most exciting was from M&S. I wanted to spend a £10 voucher I had. I found a super soft non wired pink bra, I took a 34aa and 34b into the unmanned fitting room, tried them on it was the softest hug I have ever had, I kept the 34aa. I put the othet one on the did not fit rack, however there was now a SA at the fitting room and she smiled at me with the knowing slook as I walked to the till. I put it on in the car and wore it the rest of the day.

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    • #184734
      Michelle Liefde
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      Registered On: May 27, 2018
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      I have been very fortunate that my wife and I are about the same bra size so she has given me a few of her older bras for now.  Though we do plan on a fitting some day.

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    • #184661
      Michelle Wilmington
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      Registered On: April 17, 2017
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      I 1st one I can really say was “mine” was one I recovered and repaired from the trash formally belonging to my girlfriend. since then I’ve recovered a red lacy bra and pantie set she threw out, nothing wrong with it, I think it may have been a bit small on her. (she has a very large bust). I’ve also purchased two or three of my own.

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    • #184658
      Donna Richards
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      Registered On: January 11, 2019
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      Thank you Erica for posting this. I went into a local retail store (Meijer). I was so nervous! I just guessed what size I was and hurriedly grabbed a 36 B cup off the rack. That same day, I also purchased some lace panties, a pair of skinny jeans (where I also just guessed at my size), along with some makeup. I then went over to the the self checkout lane and waited until it wasn’t very busy. I scanned my items as fast as I could, and got the hell out there before someone recognized me. Since then, it’s become much easier.

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    • #184545
      Annie Green
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      Registered On: May 26, 2019
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      I can’t believe it – I bought my first bra over the weekend.  I bought it online from barenecessities and it arrived today, a black strapless pushup bra with silicone inserts, in 34A.  I’m wearing a bra for the first time in my life as I’m writing this to you.  You’re all so right – it’s a lovely, wonderful feeling!

      I’ve always loved my bodysuits and one of them has a shelf-bra inside it.  That seemed just fine, since my way of being a CD is to underdress.  I still love the all-over hug of a bodysuit and the sense it gives me of stepping into a female body.  But a pushup bra – wow!  And I invested in a pair of black skinny jeans too.  So I suddenly find myself here amazingly enfemme, way beyond underdressing, and it feels so freeing to be Ann.  I’m pretty sure I’m not going to want to slip out of this outfit 🙂

       

      2 users thanked author for this post.
    • #182530
      Donna Richards
      Lady
      Registered On: January 11, 2019
      Topics: 1
      Replies: 40
      Has thanked: 67 times
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      Despite having crossdresserd on and off for 30+ years I bought my first bra yesterday! I’m a quick mover!

      I measured myself beforehand so I would know roughly what size I need. I got lots of good advice and encouragement from friends on CDH. Then yesterday I plucked up the courage to go into a lingerie store.

      I should not have worried. The shop assistant was absolutely wonderful. I tried on a few and left with a beautiful matching set of bra, panties and garter belt.

      Full story on personal crossdressing stories forum.

      Despite having crossdresserd on and off for 30+ years I bought my first bra yesterday! I’m a quick mover!

      I measured myself beforehand so I would know roughly what size I need. I got lots of good advice and encouragement from friends on CDH. Then yesterday I plucked up the courage to go into a lingerie store.

      I should not have worried. The shop assistant was absolutely wonderful. I tried on a few and left with a beautiful matching set of bra, panties and garter belt.

      Full story on personal crossdressing stories forum.

      Hi Sophie,

      That was very smart to measure yourself before purchasing your first bra.  I could’ve saved myself a lot of anxiety if I would’ve done that.

      xox

      Donna

      1 user thanked author for this post.
    • #182529
      Anonymous
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      Got my first bra about 9 months ago; Amazon, and it didn’t fit, so it was donated to Goodwill.  Since then I have purchased a few more, both in-store (self-checkout) and online – and I’m STILL looking for the right fit.  It must have adjustable straps (no problem there), but I still have issues with the cups.  I’m a decent 36A, but a wider rib cage than GSs means further apart breasts, and the fronts aren’t adjustable.

      1 user thanked author for this post.
    • #182526
      Donna Richards
      Lady
      Registered On: January 11, 2019
      Topics: 1
      Replies: 40
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      Donna,

      That brings back memories: I did that once (not my first purchase I have to admit) in a store on holiday. I wanted to avoid attention as I didn’t speak the language, went to self-checkout, paid and…didn’t notice the bra had an electronic anti theft tag. I got much more attention when the alarm went off and I had to lay everything out with my receipt!

      S

      Hi Simone,

      Oh my God!  I would’ve been devastated.  I’m very fortunate that didn’t happen when I purchased my first bra.

      Hugs,

      Donna

       

      1 user thanked author for this post.
    • #181989
      Donna Richards
      Lady
      Registered On: January 11, 2019
      Topics: 1
      Replies: 40
      Has thanked: 67 times
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      <p style=”text-align: left;”>For me, it was high anxiety.  So I went into a local department store (Meijer) and I was so nervous.  I had an idea of what size I was, but wasn’t sure.  I hurriedly grabbed a 36 B cup and threw it my cart, covering it up with other items in my cart.  I also purchased that day some girly jeans, panties and makeup.  Next I strolled over to the U scan area and waited until it wasn’t busy.  I scanned my merchandise as quickly as I could and got the hell out of there before someone recognized me.</p>

      1 user thanked author for this post.
    • #181952
      Kristy Violet
      Lady
      Registered On: April 3, 2019
      Topics: 15
      Replies: 57
      Has thanked: 82 times
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      It was a really long time ago, as a teenager. I believe it was LaSenza I bought it from. Was a solid purple bra and panty set. 32B at the time is what I fit into. Loved that thing. Wore it under my sweatshirt to school. Terrified and excited at the same time!

      Unfortunately it fell victim to my first purge … such a shame 🙁  I definitely have a lot more fun lingerie shopping now though 🙂 No more pacing around the mall 10 times making sure there’s no one else I know within 10km haha.

      5 users thanked author for this post.
    • #181948
      Azalea
      Lady
      Registered On: May 4, 2019
      Topics: 1
      Replies: 14
      Has thanked: 38 times
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      If I remember correctly I wore one when I was 5 and just finished taking a bath. I think it was my mom’s as well.

      2 users thanked author for this post.
    • #181945
      Nicole Box
      Lady
      Registered On: May 26, 2019
      Topics: 8
      Replies: 148
      Has thanked: 163 times
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      When I was around 11 my sister left two bras and some panties in the trash that was my job to collect. I grew up with three sisters 13-4 years older than me. So all their old clothes would end up at our house in our house in storage.

      4 users thanked author for this post.
    • #181382
      Patty Phose
      Duchess
      Registered On: May 7, 2016
      Topics: 0
      Replies: 1839
      Has thanked: 1430 times
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      I went to a store and bought it.

      2 users thanked author for this post.
    • #181106
      Lucinda Hawkns
      Lady
      Registered On: September 1, 2015
      Topics: 6
      Replies: 1381
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      when i got married wife was at work and i tried on one of her bras and the feeling of it was so intense feeling, but i tried on a bra before that was my grand mothers back when i was about 13 or 14 years old. x dressing came back and wanted to feel a bra again, so tried on one of my wife’s bra;s from there i started to buy my own, wife knows of my hobby or desire to x dress and knows i have my own collection of female attire,  more then she does and i wear female cloths more then she does

      3 users thanked author for this post.
    • #181087
      Donna Richards
      Lady
      Registered On: January 11, 2019
      Topics: 1
      Replies: 40
      Has thanked: 67 times
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      Thank you Erica for posting this.  I went into a local retail store (Meijer).  I was so nervous!  I just guessed what size I was and hurriedly grabbed a 36 B cup off the rack.  That same day, I also purchased some lace panties, a pair of skinny jeans (where I also just guessed at my size), along some makeup.  I then went over to the the self checkout lane and waited until it wasn’t very busy.  I scanned my items as fast as I could, and got the hell out there before someone recognized me.  Since then, it’s become much easier.

      5 users thanked author for this post.
      • #182013
        Simone C
        Lady
        Registered On: January 23, 2019
        Topics: 9
        Replies: 182
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        Donna,

        That brings back memories: I did that once (not my first purchase I have to admit) in a store on holiday. I wanted to avoid attention as I didn’t speak the language, went to self-checkout, paid and…didn’t notice the bra had an electronic anti theft tag. I got much more attention when the alarm went off and I had to lay everything out with my receipt!

        S

        3 users thanked author for this post.
    • #180563
      Alice Eliot
      Lady
      Registered On: February 9, 2019
      Topics: 3
      Replies: 57
      Has thanked: 28 times
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      My first bra wasn’t a bra but a good old fashioned full bra-slip (proper hook and eye back fastening) nylon with lace cups. I inherited my bedroom from my sister when she moved to London, and this ‘thing’ was left in a chest of drawers. It fitted perfectly (apart from the cups, obviously) so I knew straight away that I needed a 34in chest bra. Not long after, the first bra’s I bought were a twin pack of lace underwired black/white bra’s from M&S in Lowestoft, complete with matching knickers – hell of a rush, the whole of Lowestoft was watching me! Bra’s fitted fine, knickers were far too big – I’ve learnt since then.

      I really miss full bra-slips, I have a few that I’ve gleaned from E-Bay, but these days I’m a 38/40in chest and they are so hard to find.

      6 users thanked author for this post.
    • #180455
      Ashley
      Lady
      Registered On: May 25, 2019
      Topics: 4
      Replies: 261
      Has thanked: 938 times
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      When I realized that whatever I bought on Amazon it would just come in a generic Amazon package,
      one of the first women’s items I got besides panties was a sports bra. Even though I really wanted a real bra with cups, I was worried I’d just feel dumb with my man boobs not filling it out, so sports bra it was.

      Discovering breast forms and first real bra is a whole different story….

      4 users thanked author for this post.
    • #180423
      Anonymous
      Topics: 0
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      My sister figured out I was wearing her stuff and measured me and we went out and got me some stuff including my first bra. White, lacy trim and a C cup. Then she made me a set of inserts what we now call breast forms out of material on her sewing machine, she’s quite a seamstress. I loved all that stuff and used to dress in it for weekend parties. I met a guy and he had gay friends and we used to hang out there on the weekends. Good times.

      3 users thanked author for this post.
    • #180404
      Sophie Underhill
      Hostess
      Registered On: May 19, 2019
      Topics: 7
      Replies: 36
      Has thanked: 93 times
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      Despite having crossdresserd on and off for 30+ years I bought my first bra yesterday!  I’m a quick mover!

      I measured myself beforehand so I would know roughly what size I need. I got lots of good advice and encouragement from friends on CDH. Then yesterday I plucked up the courage to go into a lingerie store.

      I should not have worried. The shop assistant was absolutely wonderful. I tried on a few and left with a beautiful matching set of bra, panties and garter belt.

      Full story on personal crossdressing stories forum.

      8 users thanked author for this post.
      • #181093
        Anonymous
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        Well done Sophie!

      • #180442
        Anonymous
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        Congrats on buying your first bra yesterday!

    • #180378
      Nikki Dahl
      Lady
      Registered On: July 20, 2018
      Topics: 0
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      I was twelve when I got my first bra. I “borrowed” it from a friends mom. Black with leopard cups. Matching panties too!!

      3 users thanked author for this post.
      • #180438
        Anonymous
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        That was nice Billy

        It is a great place to borrow a bra from 😉

        Any chance you still got it?

    • #180199
      Anonymous
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      I bought my first bra from a local clothes shop when I was around 15. I remember being scared to death. Of course it was the wrong size! Over the years I’ve found my correct size and I love shopping for bras. I always wear underwired full lace cup bras.

      4 users thanked author for this post.
    • #180198
      Natalia K. Lanvaldear
      Lady
      Registered On: May 16, 2019
      Topics: 1
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      I used my cousin’s bras for several years, later then I bought my own from an online store.

      4 users thanked author for this post.
    • #180031
      Anonymous
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      As far a getting a bra that was truly mine…I walked in to Fredericks of Hollywood…asked for a bra fitting and left with 2 beautiful treasures! (This was back in the early 80’s…and even then, there were some store clerks that didn’t bat an eye at a man loving feminine things…and in TEXAS no less…lol!)

      5 users thanked author for this post.
    • #180005
      Genivieve Bujold
      Lady
      Registered On: April 13, 2017
      Topics: 3
      Replies: 99
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      I went to a Lane Bryant store, got fitted by one of the sales girls and bought three, on a sale (buy two get one).

      6 users thanked author for this post.
    • #177320
      Petra Y
      Lady
      Registered On: September 14, 2015
      Topics: 0
      Replies: 15
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      Don’t know when I got my first bra that I could call my own . Tried on my mothers and my aunts and my cousins many times before the age of ten.
      The bra is what it is and what it was all about. I love wearing a bra. My favorite now are two front closure one white and one black. Wear them with what ever else I am dressing in nearly every day.
      I own about a dozen bras now.

      3 users thanked author for this post.
    • #177288
      Leah
      Baroness
      Registered On: June 13, 2018
      Topics: 3
      Replies: 351
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      I first tried on my sisters bra around the age of 10 or so.  Always have loved the look and feel, fast forward a found a couple of different bra’s unclaimed in the laundry room. One was a front hook pint 34C lace bra…loved that one!  I love the 36B size with  smaller cups and need to use bra extenders for it to fit. The bigger bra’s 42 – 46 band size you get such a large cup size that I do not prefer.  For me the smaller band/cup size looks and feels sexier.  I now wear a bralette almost daily, since you cannot see or feel it under my shirt. In contrast a bra even under a thick sweater can be easily felt and seen.

      3 users thanked author for this post.
      • #177296
        Anonymous
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        Yeah Leah

        That’s an advice i would like to take and you have told about that previously as well

        Thanks Love💖

         

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    • #177230
      helenmarie
      Lady
      Registered On: August 1, 2018
      Topics: 11
      Replies: 191
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      Hello  Alex,        When I first started to CD, bras did not interest me, knickers where my thing [still are]. So when I started work in my late teens, I went & bought one, in our local BHS store [all gone now]. I went into the girls department & bought a bra & knickers set, 34A bust. I thought that ladies bras where going to be to big for me, as my mothers bras where quite large, now I know how to measure them. Funny I still have that bra, but have loss the knickers, never mine.

      love,  Helenmarie

      3 users thanked author for this post.
    • #177057
      Anonymous
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      It was my mom’s.

      Bra always intrigued me and when i was alone at home and i wend to my mum’s room and found a simple black bra and tried it. It wasn’t my size and i had real trouble putting it on but finally managed it. Once i was done i felt really excited and later i tried a few others as well. I still sometimes try my mum’s bras and they are really tight on me but at least i can put them on quickly now practice makes perfect. 😜

      4 users thanked author for this post.
      • #177086
        Anonymous
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        That’s nice Tracy  it must have been exciting

         

        2 users thanked author for this post.
    • #176789
      Fiona-Ann Moss
      Lady
      Registered On: October 7, 2018
      Topics: 368
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      How did i get my first bra? well, i went into a shop and bought one! seriously though, i had no idea of my cup size, and being a Girl with a relatively small frame, i did not want a bra that was too big. A 32A or B does for me nicely as that is a training bra size.

      Going and buying it was no problem, working out the cup size was…..

      Fiona xxx

      3 users thanked author for this post.
      • #180291
        Anonymous
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        I will tell you this Fiona because as a Brit you might be the only one who understands. I went into Tesco observed the lie of the land moved into the bra section like a member of the SAS on manoeuvres, picked up a cheap one in a chest size I thought would be correct and a cup size to make me lol like Diana Dors. and beat a hasty retreat to the self service checkout. Not glamorous, not exciting but true. Also not a great fit but it took dressing to another level. Sorry I couldn’t get more Brit relevant name checks in lol.

        Donna x.

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        • #180338
          Anonymous
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          Hi Donna, I’m a Brit and I’ve done exactly the same as you. Now I get most of my underwear from Sainsburys and I’m as bold as I can be. Tanya.

          2 users thanked author for this post.
          • #180339
            Anonymous
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            Thank God for self service checkouts Tanya.

            Donna.

    • #176649
      Caty Ryan
      Baroness
      Registered On: August 27, 2017
      Topics: 119
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      Has thanked: 8 times
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      I wore my mothers as a child/teenager. My first one I bought myself was on an interstate business trip in the 70’sa. Initially I would buy then discard before I got home. (tear in corner of eye). After that as a senior in the company I worked for I could store all Caty’s things in an old wardrobe out in the warehouse.

      Now I have a full wardrobe with most of it in a storage unit and must have at least 20 bras…

       

      Caty

      5 users thanked author for this post.
    • #176635
      Davina Evans
      Lady
      Registered On: March 23, 2019
      Topics: 1
      Replies: 100
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      My first bra was one of my mothers. Fitted when I was young as did her corset.
      Recently I used Google to find how to fit a bra and to work out the cup size. Down to the store to buy, saw a nice black bra. Back home perfect fit! Happiness. Back down next day for one white and one red.
      Now buy from store all undies in male mode no body looks nor worries about it.
      Davina

      3 users thanked author for this post.
    • #176563
      Anonymous
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      I used to work out at a gym that was woman one day and men the next. Found a bra in the locker one day and once I realized, I tucked it in my gym bag. Couldn’t wait to get home to try it on!

      3 users thanked author for this post.
    • #176436
      Roberta Thomas
      Lady
      Registered On: September 15, 2018
      Topics: 63
      Replies: 535
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      Roberta i sincerly hope you will get to wear bras soon and enjoy what we have been feeling

      Good luck with that hon 😘

      Thank you Alex honey.

      1 user thanked author for this post.
      • #176453
        Anonymous
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        Love 💖💖💖

        1 user thanked author for this post.
    • #176348
      Michaela Jane
      Lady
      Registered On: December 9, 2016
      Topics: 30
      Replies: 429
      Has thanked: 552 times
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      I didn’t get a bra until after I lost my wife. I wore hers first but the cup size was wrong for me and I needed extenders for them. In the end, I bought my own bra, off the shelf at Walmart, it was a plain white, underwired, soft cup 42C. I now have seven bras.

      4 users thanked author for this post.
    • #176340
      Marianne
      Ambassador
      Registered On: May 20, 2017
      Topics: 12
      Replies: 464
      Has thanked: 283 times
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      As a teenager  I did try on my mom’s bras a couple of times to make her dresses hang better on me. Fastforward a dozen years and I tried on the clothes of my fiancee in secret. We were the same size back then, so her 38B bras fit me fairly well. One day I was looking at bras in a store and found a heavily padded red super pushup bra with lace overlay in 38B and simply bought it with no questions asked.

      Since then it has been quite a number of bras and everything else making up the complete wardrobe of a modern woman with a good sense for fashion. Until recently I have been wearing 36A bras without breast forms but am currently outgrowing them and now buy 36B. I hope being able to look good in a bikini for next summer.

      • This reply was modified 1 month ago by Marianne.
      6 users thanked author for this post.
    • #176275
      Roberta Thomas
      Lady
      Registered On: September 15, 2018
      Topics: 63
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      Hi Alex.I am really glad you started this topic.I have been crossdressing for many years but have had little experience of wearing bras apart from a few attempts at trying a couple of my wife’s on.That didn’t work out too well as it was too small for me.Since my wife has been fully accepting about my feminine side I have broached the subject by azking her to buy me a bra.I am not sure if she will comply but I will work on her.I am also seriously comsidering breastforms.If I could only workout my measurements that would be a start.Whenever we visit our favourite UK department store M&S I always look at the lingerie sections they have a wonderful array of bras and panties and their range of pantyhose/tights is great too.

      5 users thanked author for this post.
      • #176408
        Anonymous
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        Roberta i sincerly hope you will get  to wear bras soon and enjoy what we have been feeling

        Good luck with that hon 😘

        3 users thanked author for this post.
    • #176158
      Emma
      Lady
      Registered On: March 30, 2019
      Topics: 4
      Replies: 10
      Has thanked: 24 times
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      The first bra I ever Weared was my Cusins  Emerald green velour bra it’s was beautiful I think I was 8 or 9

      4 users thanked author for this post.
      • #176232
        Anonymous
        Topics: 0
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        That was wonderful Emma

        Even most girls don’t get to wear bras at that age

        1 user thanked author for this post.
    • #176147
      Samantha Roarke
      Duchess
      Registered On: April 17, 2019
      Topics: 48
      Replies: 1713
      Has thanked: 6812 times
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      I bought my first bra at a store years and years ago. I measured at home first, then I ran into the store, quickly looking at the bras. I’m sure I was red and sweating, I found a black racer back bra, I was so nervous checking out this was WAY before self checkout. I took my treasured bra home and I still have it  “34-B”. I now have a fair amount of bras mostly 36-D’s. lol wow that was so long ago!

      3 users thanked author for this post.
      • #176236
        Anonymous
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        I see that you really cherish those memories. How i will do that too my first bra was about 10 years ago

        2 users thanked author for this post.
    • #176144
      Anonymous
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      My SO bought my first one for my own. I would use hers, but she bought me my very own for my Bday.

      Chelly

      5 users thanked author for this post.
    • #176109
      Anonymous
      Topics: 0
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      My wife gave me one of her bras to put on for a Halloween party–I think 34D………..white……

      Two weeks later, MY WIFE gave me my FIRST MY OWN Bra—lacy pink, padded, push up, underwire bra in my size 36B………..

      From then on, I bought all my other bras, same size, and we often go and buy bras together !!! My wife doesn’t buy bras for me, nor panties……….she will on occasion buy makeup needs or lotions, or shaving gel and once she gifted me a finishing brush I really wanted !!!  she early on told me I had to be Mikki and  not her !!!  I was totally OK with that !!

      Mikki

       

      6 users thanked author for this post.
      • #176252
        Anonymous
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        That’s cute Mikki

        Glad to hear you have such a great wife

        And thanks for all your support for me i will get back to you 😘

        3 users thanked author for this post.
    • #176107
      Candy Can
      Lady
      Registered On: October 19, 2018
      Topics: 42
      Replies: 145
      Has thanked: 354 times
      Been thanked: 840 times

      I tried my mums bras when I was a kid, but they didn’t fit.
      Fast forward many years and although I had quite a collection of panties and lingerie, no bras.
      That changed when I found out, via the ‘net, how to measure myself for a bra.
      Then I went and bought one from a chain store – and it fit!

      5 users thanked author for this post.
    • #176075
      Lanna Barton
      Lady
      Registered On: May 25, 2017
      Topics: 11
      Replies: 500
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      When I was very young I found mine in a box of old cothing. It was a treasure trove of bras, girdles, garters and nylons.

      5 users thanked author for this post.
      • #176119
        Anonymous
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        I remember that box in my attic. That’s how I got started. 😂

        2 users thanked author for this post.
    • #176325
      Roberta Thomas
      Lady
      Registered On: September 15, 2018
      Topics: 63
      Replies: 535
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      What shirt size are you? If medium then you are probably a 36″ or 38″ chest. If large 40″ or 42″ upward. So bra band size if medium will be 38 or 40. Go for cup size D. If large pick the appropriate band size and go for cup size DD or E. This is because the male frame is larger than the female so breastforms need to be larger to be in proper proportion. There are plenty of posts on CDH covering this – just go back thru them.

      My shirt size is a 16 collar which is medium.Thanks a lot for your advice,so helpful.

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