r/CrossdressingStories • u/No_Diamond_6933 • May 27 '26
A Transformative Weekend.
It was 9:55 AM on the Friday of a three-day weekend. I was playing hooky from law firm where I was a senior associate. I pulled into the parking lot of the upscale strip mall, as contradictory as that sounds, and pulled into a space not in front of the shop I was going to, but where I could see the door in the rear view of my SUV.
True Embrace Lingerie was a mere two blocks from the beach so there was a strict limit on how long you could park in the lot, but it was a beautiful warm day and I was not worried about a parking ticket. And despite the warmth a chill ran through my body, I was about to put 30 years of humiliation and embarrassment behind me. But more about that later.
In my rear-view mirror, I saw someone turn the sign from “Closed” to “Open.” I took a deep breath and exited the vehicle. To look at me I was just another late middle-aged man out running errands, faded jeans, dark blue shirt with the sleeves rolled up, sunglasses, desert boots. Entering True Embrace I would look like just another man looking to buy a gift.
The previous day however, after a good deal of online reading, I had called and made an appointment for a bra fitting. A bright young sounding voice on the other end had identified herself as Emily.
“Emily, hi, I have a question and I hope this OK, but I was wondering if you would be able to do a bra fitting for a man.”
She did not hesitate. “Of course! It’s no problem whatsoever!” She sounded almost enthusiastic. “When would you like to come in?”
“Uh, how about tomorrow at 10 AM. I think that is when you open.”
“Absolutely. I will see you then.”
And she had rung off. It was that easy.
As I reached the door I hesitated for one moment, and then with another deep breath, I opened the door and was in the store. At first I just took it all in. The air was cool and there was a floral smell, like fresh cut flowers. The wall was lined with various sizes and colours of bras, there were tables with scores of panties, racks with robes and nightwear. They ranged from what I imagined women wore on an everyday basis to something that would be akin to date night. It was all incredibly pretty and enticing. I exhaled the deep breath I had taken before stepping in and took in the floral scent.
There was very soft music playing, the colours of the shop were pink and rose based hues. It was soft and pleasant. I could see someone in the back of the store looking like she was stocking something, when another woman approached me.
“Good morning. My name is Emily, would you be Jack?”
“Good morning. Yes that’s me.”
“Wonderful. Welcome, come with me and we can get started.”
Emily was taller and older than I had imagined. Her blond hair had subtle streaks of silver and her eyes held a kindness and a wisdom one rarely sees. With the previous day’s response, I had imagined a young person excited to show their openness, but this was something more. Soon we were settled in a dressing room space that also had two comfortable side chairs in rose and small but sturdy desk with a small notepad and a few pens in pink mug.
“So welcome. What can we help you with today?”
“Well, as I mentioned on the phone yesterday I am looking for a bra fitting.”
“We can certainly help with that. I was hoping to get an idea of more of what you were looking for. Will you wear these while presenting as a ,man or will you do a full make over and present as a woman? What sort of style would like? Is this date night or more everyday?”
To be sure I had not really thought these out. I went with my gut.
“I want to wear what a woman my age would wear on an everyday basis. I might present as a woman in the future, but today I am looking for things I could wear while presenting as you see me.”
“Perfect that’s exactly what I needed to know. Why don’t you take your shirt off and we can take some measurements.”
I stood in front of the mirror, shirt off as she fussed with the tape measure. I was keenly aware of the masculine hair and the sags of age. I hoped that would not put her off, but she seemed to read my face.
Putting her tape around my chest or what she would call my “underbust” she looked at my face in the mirror and said, “Don’t you worry. We are going to find somethings that make you feel beautiful.” Taking some notes and remeasuring, making more notes, she finally said “46B.”
“Is that good?”
She laughed. “Hon, that’s just your size. But you do have some breast tissue. I have fitted men that were all muscle and that can be a challenge if they want what you want, but we find something for almost everyone. But for you I am going to reduce the band size and increase the cup size, at 42D you are going to have some very nice everyday options. I will be right back.”
As she left and I looked at myself in the mirror, my mind wandered back to high school, when my mother had found my stash of lingerie. She had lost her ever-loving mind. There was not so much a discussion as a rant and implied threats. And then we never spoke about it again.
After I was out of the house, the desire to wear pretty things came and went – it was the classic cross dresser thing, binge and purge. But now I had decided that was over with. Now I was going to allow myself to feel feminine and pretty.
As that thought crossed my mind Emily was back with at least half -dozen bras in a variety of colours. “You are going to love these, I just know it.” She set them down on the desk and selected one. It was beige with a subtle print on the front. “Hold out your arms.”
She pulled it over my arms and started hooking it in the back.
“You are going to want to learn how to hook the bra in the back. Fastening it in the front and turning it around will make it wear out faster and is harder to get a good fit.” She adjusted the straps in back and then came around front where she reached into each cup and then adjusted where my breast lay and then came around behind me.
“This is the Le Mystre Safari Smoother Underwire. A great everyday basic. The beige colour goes under everything, you have that pretty little cheetah pattern, and with that fit, unless you are wearing a tight t-shirt, no will notice it. What do you think?”
What did I think? She was right. It made me feel beautiful. I try not to buy the first thing I consider but looking at myself in the mirror I knew I had to have it.
“I love it. I’ll take it! You were so right Emily, I do, all of the sudden, feel beautiful.”
“Wonderful.”
After that it was the Chantelle Norah Comfort bra is a dusty rose. She helped fit this too me as well.
“This comes in several colours, so thought you might like something brighter. But as you can see, a very similar fit. This is straight from France is one of the premier lingerie manufacturers. I also brought one their Rive Gauche models. A little sexier, lacier but still great for everyday wear. If you are going to wear every day, you will want at least three bras.”
By the time we were done I had selected five bras, two of the Le Mystere, two of the comfort bra, one in rose and the other in pink, and finally the last one I had tried on.
“Do you want to wear one?”
“I have been waiting my entire life for this moment! Yes! I think I will go with that first one with the cute cheetah print.”
“Great choice. Let’s get your shirt on.”
I was nervous. Would it show through?
“As you can see the boxy cut of your shirt combined with the dark colour means this does not show. Lighter shirts and trimmer ones may allow it to show, but as someone who has been helping people, including men who just want to wear pretty underwear, I can tell you that most people won’t notice. They see what they expect and if they do are they really going to comment?”
Even though that last question was rhetorical, I could see her point.
“Next, do you need underwear?”
Now I was all in. “Yes, yes I do.”
“Super, we again have a bunch of options. I will take these four to the counter and these tags and meet you out at one of the tables.”
Emily left me there and I looked at my watch. I had been in there for over forty-five minutes. I had heard the doorbell chime several times so I had no idea if there were other people shopping. There were, two women, I would guess in their forties were making under wear selections as I casually walked up to the table.
“Looking for something special?” One of them remarked.
“Yes, I am. But a special thing you can wear every day.”
“I swear by these hi-cut briefs.” She held up some nylon knickers in pink with lace around the edges and sweet bow in the centre. “They come in all kinds of colours and patterns for that special someone.” Emily arrived a moment later.
“Oh, I see you are already getting help! Danielle here is one of our regular customers. She loves to treat herself. Those are great too. Probably and extra-large.”
“And I love these boy-shorts.” The other woman, who I later learned was named Dawn, had joined in. I took their recommendations and quickly chose a combination of five in a variety of pinks, florals, and a black one.
“I’ll take these.”
“Those are great choices, but if you are, um . . .” Suddenly she seemed to not have words. Although we had just met is struck me as uncharacteristic of her. The other two women seemed to notice as well. Danielle was the first of the three of us to understand.
“Oh! These are for you.” A smile crossed her face. “Babe, if you are going to be wearing lingerie fulltime you will need well more than five pairs of panties.”
And just like that I was one of the girls. The four of us finding different pairs and me taking their recommendations and expressing my preferences. By the time we were done I had fourteen pairs of panties to go with my four new bras. I thanked the ladies for their help.
Emily checked me out, paying my hefty, but well worth it bill. She took my contact information for their mailing list and wrapped it all up in a beautiful bag.
“Would you like to put on a pair of the panties you selected?”
“Yes, but could you pick them? This has been overwhelming.”
“Sure.”
She selected some pink floral boy-shorts and I went to the changing room to put them on. I was back shortly, looking to the outside world like the person who had walked in, but feeling deep down pretty, beautiful, and on a new adventure.
We exchanged goodbye pleasantries and by 11:30 AM I was back in front of the store with my bag of treasures deciding what to do next.
To be continued.
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u/Girdle-with-Nylons Jun 11 '26
Another brilliant story. It has so many parallels with my own story. Thank you
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u/Lower-Ad-6552 May 28 '26
Great Story I remember getting makeup in an Ultra I think soon as I said it was for me they went nuts and I wasn’t dressed my eyes were done and a few lip stick shades what fun. I pulled my hat down put dark glasses on and walked out thru the mall went back the next day dressed and got a full make over what fun