What determines what is best for a person? Is it shaped by their environment, their parents, or themselves? In my case, it was I who decided… at least I like to think that I did, but majorly it started accidentally when a curious teen landed on the website, which wasn’t in their path of usual surfing.
This dates back to me being 18 years old, an experimental and curious teenager living in a boy’s dormitory, who somehow stumbled upon the Victoria’s Secret website. I was drawn to the beautifully embroidered lacy female lingerie sets. My first reaction was not that of a typical guy, but was instead I was immediately overwhelmed by the thought of wearing them. “How would it feel on me? That beautiful lace hugging my body! This would suit perfectly on me!” were some of the thoughts racing through my mind, but as all dreams come to an end, I came to my senses and immediately felt uneasy and questioned my sense of judgment.
While processing those unfamiliar feelings, curiosity got the better of me, and I found myself searching for titles like “Men wearing girl clothes.” “Is it weird for a guy to feel like wearing girl clothes.” etc., and reading up on the answers by others. It led to me having two choices – One was to drop everything in its tracks and never return to this topic. Or the more preferred one “Why not explore it further?”
It was obvious which one I chose, but my overthinking brain raced with possibilities as to what there was to explore. That was when I got the idea to check online to read about how others thought about this, what did they do when faced with similar situations, and how much they progressed going forward, which was much to process. I was at my wit’s end; where could I go? How do I proceed and decide if I should try on a panty or a bra? At that time, my sister, one year younger than me, came to visit. I confided in her, as an experiment. After she patiently heard me out, with a shocked, and yet excited resolve, she stood up and asked me, “What do you want to do now then?”
My answer was, “Read more. Buy some lingerie online and wear them by myself when I’m alone!” She replied, “You don’t know your size, idiot! What if you ordered online and found it to be short or large? Return it and try again? That won’t do”, Facing me, she exclaimed, “You and me are going shopping, let’s go find you your first bra and panty!” Although in fear of public shopping, she had a good point about finding out my size without a measuring tool. Conflicted, she went forward with taking my hand, pulling me along without giving me time to think.
At a mart, we quickly headed to the ladies section, which was surprisingly nearly empty. With me in tow, she didn’t waste a second and quickly headed us to the lingerie section., which thankfully was empty! She took a measuring glance at my body and selected three sets of regular bra sizes 32, 34, and 36 and told me to try them on and let her know which fit perfectly. I was dumbfounded; the section had trial rooms but was flanked by a female assistant, who likely wouldn’t let me in. Reading my mind, my sister shoved a T-shirt in my hand and said, “Wrap them in this and go!” my reply was, “I will do that, but Sis, a small problem….. I don’t actually know how to put on a bra”.
She then grabbed me, and we both made our way to the trial room. The assistant didn’t even glance and let us through. I went inside while my sister stayed outside of the door, guiding me on how to put a bra on. I felt where it rested on my bare skin, the smoothness of the fabric fitting on my chest with ease as if it were made for me!
I came out and we both made our way back to the lingerie aisle. I whispered, “It’s 36 size,” and with a playful look in her eyes, she asked, “How was it Brother; how did it feel wearing a bra for the first time? Want to change your wardrobe to all feminine clothing?” I felt embarrassed, excited, and overjoyed, and my cheeks flooded with hot blood. I said softly, “It was sensational; I felt the fabric clinging to me like it was made for me!” She squealed and hugged me tight. “Now that we know your size, what type of bra do you want?” She showed me different types of bra and their features, suggesting I start with a non-padded bra. I added that it should please be lace, too.
I dreamt of how a bra would feel on my bare skin ever since looking at that website. “I want that one,” I stated while pointing to a purple non-padded everyday lacy bra. She eyed me with a cunning smile and stated that it should have matching panties. I was like, why not? We quickly scanned the aisle for the purple lacy panties, but couldn’t find any! Dejected, my sisters showed me a purple panty (not lace) but made of satin, and as I touched it I felt like I had touched water. We made our way to the payment getaway. I was excited all the way back to my dormitories, and I said goodbye to my sister. She whispered as she hugged me, “Do tell me about how you felt in them, wear them both together and share your experience with me sister!” My face burned as she said the word sister! I felt vaguely happy by that, brushing it off, and I promised I would.
As I went to my room, I locked it, my roommate was away on a seven-day leave back home. It was the perfect moment for trying on my first set of lingerie, I quickly undressed and put them on. It felt like I wore nothing! I hurriedly went to a mirror and looked at myself.
Wow! was the expression on my face. To see how the bra placed snuggly on my chest, the lacy outline brushing off of my skin; it was heaven, I never felt more accomplished or excited before. That day marked the start of everything; how I started to where I am now. I rang my sister up, “What’s the matter? Did you want anything else?” After a moment of silence, I said, “Thank You for taking me shopping Sis!”
“Shut Up!” she laughed, “ Do you know how excited I was when you told me! Ring me up if you need any advice or my help. And wear them and make sure to share the experience, dummy!” “I am wearing them now… and … I don’t want to take them off!” I replied. Laughing, she said, “Welcome to the feminine side my big sister!”
– How was your first experience?
– Which was your first bra? and what is your size?
– What were the problems you faced?
Stay happy and party!
Best,
Maxine
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- Internet sure has other Plans! - August 3, 2024
@Maxine Williams My first experience of putting a bra on occurred when I was not even a teenager, probably only 8 years old. My parents were out and I went into the bathroom to have a shower, and saw one of my mom’s bras hanging up with her other clothes on a drying rack, I think it was the top to one of her swimsuits. I had always felt I was supposed to be a girl and I pulled it down and figured out how to put it on. I was not wearing anything as I was going to have… Read more »