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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
@maximusmax 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 a shower. I stuffed the cups with some socks, tucked my privates between my legs, stood in front of the full length mirror, and realized that was what I was supposed to look like. Here I am today, many years later, after finding I have always been an intersex female, and the memory of how I felt then is still vivid in my mind.
Today, after having several bra fittings over the years, my size is still a 42D. The only problems I've faced, telling the world I was transgender, have been overcome, and I transitioned to living as the woman I was truly born as.
Hugs,
Ms. Lauren M
Well, you landed on your feet with that one. I don't think I'd ever tell my sister, she is very traditional, as is my daughter. My son knows and although he has seen photographs of me, he has yet to see me dressed.
My first experience is as noted in my article on my home page. It was pretty easy going, I wasn't too worried and things just got better from there. My wife obviously knows and we go out together as women.
TBH, it's all been pretty straightforward.
Now there's boring for you 🙂
Becca
Haha that's true, I am lucky to be blessed with an open mind sister. Infact she keeps tab and regularly does ask if I did any other endeavours or something... The excitement she shows is far greater than my own tbh 😂 and I find it amusing!
Hey no fair, every story is interesting for me... I'll look yours up soon don't worry 😂 and also I promise I won't find it boring. And it's cool that the people around you have been open with you.... Not such a case with me tbh... I didn't tell them yet. I will be posting another story soon ☺️
Love
Maxine
Thank you have that lovely post, it qas great fun to read, and what lovely sister you have to be so open and more impprtantly, helpful.
Back in the dark ages...before the internet, we did the samething, only with the Sears catalog. No doubt prior to that othwrs found othwr ways to get introduced to femme wear. Probably just by seeing women and being curious as to what they wear, since crossdressing has been with is through the ages.
For myself, it was a curiosity to wear what women wear and one day I just decided to try on all my mothers clothes and wig, et cetera. It was great fun, but once my curiosity qas satisfied I did not even think about dressing for years. But, once I felt that tight bra and silky panties I was hooked, it just took many years for it to come back to the surface. Like you standing there in yoir locked dorm room wearing nothing but a bra and panty, that moment is just seared in our brains. For me that was nearly 50 years ago, but I remember it in gtrat detail.
Yes yes I do have a great sister 💝 and soon you will hear some more about her!
Ah I am not of that generation 😂 sorry I have no idea what I would do without internet tbh. Although I did also see some magazines and do imagine what the dress/lingerie will feel like on me, so I can totally relate! But yeah the first ever feeling of wearing them is forever engraved in the mind... It's not something you forget ☺️. Love to hear about your further endeavours. Seems like you did enjoy the process too! Tell me about it!!
Maxine
This story is so fun and exciting! Have you expanded further with your sister? I would love to have someone close give that caring advice and excitement. A few years back my wife and I were talking about makeup (she really doesnt wear any) and her daughter (my stepdaughter) does. I said how cool it would be if she knew and would help. My wife seemed to be on board. So my wife went away and I dressed up and had a texting conversation with my stepdaughter. She seemed pretty excited about the idea and I even sent her a picture. She asked my wife was still away about it and my wife panicked and texted me WTH. She ended up telling my step daughter that I was just fooling around and got drunk and was not serious. I apologized briefly the next day. I still think about how cool it would be to go to a store and have help especially with makeup. It has never been brought up again but you cannot tell me she has forgotten about it. My stepdaughter loves drag shows and I think we would have a blast together at them.
Yes I did. I'll soon share my further expansion! It's much more thrilling tho 😂 and tbh I still do find that hard to believe that I progressed this much further in my experiences ☺️.
Wow you did have a crazy first experience 😂. But yeah did you progress any further with the idea? Or are you still pondering how to? Tho you said your wife knows. How supportive is she regarding all this?
Maxine
@maximusmax its a slippery slope and I have learned that if I simply ask once in a while when we are shopping especially if it is difficult for me to do she will eventually buy it for me but it is not often. Ive learned not to wear her cloths as well even though she then gives them to me because she says she cant wear them after I have. (the last one was a two piece swimsuit) I know I could be totally evil about that but I respect her too much. She sometimes gives me clothes she has purged and I have full reign on leggings and sports bras along with a few zyia Camis.
Stacie, I get that too. My wife came home and I was trying her dress on. She flipped out and gave it to Thrift Store. She can never wear it again. The good news she felt so bad, she went out and bought me some dresses.
Thank you for your wonderful story Maxine. You are a lucky girl to have such a fabulous sister. We should all be so lucky. I love how everyone’s stories are so different, yet have so many similarities that we can relate to. I look forward to hear more about your journey.
Love Lea
What a beautiful story! I thoroughly enjoyed reading it on a Sunday morning while enjoying my cup of coffee. More sisters, moms, wives, and female friends need to act like your sister did.
I'm looking forward to your next story!
I wonder if there are stories out there where a sister (or mom, female cousin, somebody) did the same, was supportive, and her brother explored and realized crossdressing wasn't for him.
I've always felt, "They're just clothes (shoes, accessories, makeup) anyway!"
Maxine, you have a great sister! Years ago, I suddenly grew boobs and learned that I was intersex. They were flopping around, giving me an odd shape and doing Snoopy Noses in the air conditioning. At first I tried to hide them but that was only a temporary measure, besides, my nipples chafed and were sore. I was uncomfortable and attracting unwanted attention so I measured myself and went to Kohls and bought 4 bras to corral those pups. About 10 bras later I finally found a bra that fit me perfectly (Maidenform T-shirt bra) and have been wearing them ever since. Thanks for the great story. Marg
You are gifted!
– How was your first experience? - Thrilling, exciting and its the same since last 25 years.
– Which was your first bra? and what is your size? - A red , lacy bra followed by white lacy one. Yes, i tried both back to back in 15 mins. I was 16 probably.. 😀 . I'm 39 A now.
– What were the problems you faced?
None in particular. it is always a secret trying 🙂
I have two "first time" stories. Three years in a row, my kids were in a marching band show out of state, and were planning to stay overnight and return the next day, while I returned the first night. My wife (now ex) was always asleep by late afternoon/early evening so I knew I could walk in safely. The first year I changed in the car at a rest stop when it was dark, and drove home. I almost got into an accident when someone at the last minute decided they would cut me off so they could use the high speed toll lane. The next year I changed in a unisex bathroom at the event, and hoped that the other band parents would be gone by the time I got out. I stopped for dinner at a rest stop, and drove home without incident. The third year, the unisex bathroom was locked, so I had to change in the car (while it was still light out), stop for dinner, and also stop for gas on the way back. For these events, I used an all-in-one, and stuffed the cups with poly fill (synthetic cotton). (The third year may have been after the event described below, so I may have had forms. I can't remember the exact timelines.)
However, what I consider my first time was when I went to a transformation place about 30 minutes from home. I not only got a makeover, I was taught how to do my makeup in the process. After the makeover, and being loaned a more flattering top, we went out to dinner at a local diner. Surprisingly, I was not nervous except for a few moments when I first got in her car, and when I first got out at the diner. Not only did she give me the makeover, I wore my own hair with clip-in bangs (fringes) that she gave me. And she gave me the bra, a black lacy front closing bra, and the breast forms, which were foam and were already yellowing by that point.
I never told my parents, and I havent told (and have no plans to tell) my siblings. My ex and my adult kids know. Two still live at home and I dress in front of them all the time, sometimes partially, sometimes fully.
A few years ago, I bought forms one size smaller which looked better on me. Last year I lost weight due to illness, and I've been using the tighter setting on the bras, but may even be able to go down a band size.
awesome story thank you for sharing
Amazing story! One of the best I’ve read in the last few months.
C💋
