Later on I’d continued to argue with my Dad, specifically about him making me buy a bra tomorrow, but he was adamant. My sister Chelsea told me they weren’t so bad, which was the attitude she took to almost everything I had to adapt to since the changes started. She was supportive of me and sympathized with me, but I knew she kind of liked it all too. It gave her the opportunity to be a good big sister. She was the only girl in the family since our mother died. When I had my first period last month, Chelsea actually cried and hugged me before giving me a tampon.
I wasn’t able to convince my dad to let me remain braless, so my sister volunteered to take me bra shopping tomorrow. The next day the two of us drove to Lynn’s Ladieswear, and the entire drive I was pretty quiet and brooding.
“Make sure everything fits and everything comfortable. You might think ‘good enough’ but trust me you’ll be regretting it after not long.” She warned me. I rolled my eyes and looked out the window.
When we got there I walked in hesitantly behind Chelsea. There were racks and mannequins covered in panties and bras and nighties and stockings and whatever else. Everyone who worked here and shopped were women. As a guy I’d feel weird in a place like this, but nobody thought anything of it, considering I WAS a girl now. Chelsea walks up to an employee, and older woman.
“Hi ma’am, my sister here needs her first bra.” She said with pride in her voice, her arm on my shoulder.
“Oh, how exciting!” The older woman whose nametag read Debra said “Well you’ve come to the right place! What’s your name hon?” She asked me. I froze, because I didn’t want to tell her my name was Ben. I’d been meaning to decide what to call myself in this situation but now my mind was blanking.
“Betty!” Chelsea chimed in. I looked at her a mouthed ,”Betty??” Betty would not have been my first choice.
“Betty, I’m Debra. Right this way sweety.” Debra said, leading me deeper into the store. I looked back at Chelsea with one more ‘help me!’ expression but Chelsea just waved me goodbye.
Debra led through a gallery of bras.
“Do you know what size you are hon?”
“No, I, uh, I’ve never had a bra before.” I said looking at the floor.
“Oh yes of course, silly me! That means we’ll need to measure you!”
Debra led me into an area with three mirrors so I could see myself from an array of angles. She took out a tape measure and asked me to lift my arms. What followed was a serious of embarrassing measurements, with Debra wrapping a measuring tape across my tits several times from different positions. She told me what size I was but I quickly forgot, but Debra wrote it down for me. She picked out a series of bras for me to try on in a dressing room.
In the dressing room alone with four bras to try on, I thought about how I knew I’d have to do this eventually, ever since my boobs started to appear. I took a deep breath and took to it, pulling my shirt off. I looked at the bras, some of them were frillier and pinker than others. I decided to try the plainest, whitest one there was, with the strange logic that it was the most masculine one. I put my arms through the straps and put my boobs in the cups. Then I reached back to hook it but after a minute of struggle I realized I couldn’t do it. I looked around, hoping to think of something, but then I sighed and asked Debra for help.
“Of course sweety!” She said, stepping into the room. She showed me how to bend my arms to hook it, then to lean forward and jiggle to make sure everything was in place. It was so uncomfortable, especially since I had to look at myself in the mirror while I did it.
“What do you think, comfortable?” She asked. In truth, I had no idea if it was supposed to be comfortable or not. This was the first one I’d ever tried and I had no interest in trying the others.
“Yeah.” I lied.
“Then I think that’s the one for you! Enjoy your first bra, honey! I know it might feel strange now, but soon you’ll start to love it. Breasts are wonderful.”
Yeah right. Breasts sucked, so did my long curly hair tied up on the top of my head and so did my slender, weak arms.