Bra Shopping

This article was submitted by Torrey Grover, a 50ish occasional crossdresser living in the intermountain west. Although presenting as male, he does have long hair and wears a lot of unisex outfits in public.

For years I had been window shopping at Victoria’s Secret and dreaming of buying a nice bra.  I knew that Monday mornings were the slowest time of the week which would make the clerk anxious to make a sale, and reduce the risk of any encounters with other customers.   My plan was to pay cash, wear something flamboyant but gender-neutral, and have my longish hair in a neat ponytail.

As I looked for the Victoria’s Secret location  on the mall directory sign I realized my heart was racing. I found a drinking fountain then the restroom before walking down the corridor.  I saw the Victoria’s Secret ahead, slowed down, then kept walking.  I went back to the food court to sit down.   I felt that everyone was looking at me as if they could read my mind. I got my mental state back in control and was ready for another attempt. The second time I approached the Victoria’s Secret and walked right in.  I glanced around and saw that the store was empty except for one employee rearranging displays. I started wandering, knowing that before long the clerk would notice me.

“Good morning?  Looking for anything special?” It was now or never. No lying about gifts for girl friends or anything else like that.
“I’m looking for a bra.”
“Do you know what size and style you want?” She was acting like my request was perfectly normal.
“I’m not sure, probably something with small cups but a large band. Maybe a 36 or 38 B?”

She gave me a quick once-over with her eyes and smiled. She opened a drawer and began sorting through the endless piles of bras. I was savoring the experience. Eventually she pulled out a very pretty flesh-colored bra with lace trim and nicely formed foam-padded cups.

“Maybe something like this will work?  It’s a Body by Victoria push-up.  I really like this style.” I decided to go for broke.
“This sounds silly, but do you mind if I try this one on? I’m really not sure of my size.”
“That’s not a silly request.  Of course.”

I followed her back toward the changing rooms with the bra in my hands.  I have no idea what I would have done if we had encountered another customer at that point. She unlocked the white-and-pink door, and I went inside. I took off my shirt and undershirt, slipped my arms through the straps, and struggled with the fastener.

“How does it fit?”
“OK, but a bit tight.”  I had given an honest answer to what seemed a perfectly normal question.
“Let me get you another one.” A moment later I saw a hand drape another bra over the top of the door.
“This one may have a bit more stretch. Is the problem that the band is too tight?”
“Yes. Do you have this style in a 40?”
“Unfortunately, we only stock larger band sizes in C and D cup.  Have you considered a bra extender?”

A moment later she came back and handed  a package over the door.
“These will add a couple of inches.”

I took out a two-hook flesh-colored extender, attached it to the bra, and tried again.  This time the fit was perfect!  I stood straight with my shoulder blades pulled back and admired myself in the mirror. The push-up combined with my own chest fat to give a definite hint of boobs.  The feeling of having my chest cradled in the cups and the fastener against my back was wonderful. I readjusted the shoulder straps to get just the right height for the cups.

I decided I better not push my luck by lingering. I changed back to my shirt and calmly walked to the counter where the girl was waiting.  “I’ll get this one.” “I just wanted to thank you for being so understanding and helpful today.”
“I hope to see you here soon. Here’s a gift card for your next purchase”

This article was submitted by Torrey Grover, a 50ish occasional crossdresser living in the intermountain west. Although presenting as male, he does have long hair and wears a lot of unisex outfits in public.

The following two tabs change content below.

Editor Maxine

Editor at CD Heaven. Publishing articles on behalf of other users.

Latest posts by Editor Maxine (see all)


Leave a Reply

32 Comment threads
4 Thread replies
Most reacted comment
Hottest comment thread
Notify of

A great outcome for what is becoming a quite common experience for many.

Taking those first steps is always hard but, in the long run, it tends to work out better when we are honest and admit the item is for ourselves.

I hope you go back to spend your gift voucher soon Torrey.

Yea gotta go ahead and admit it
The younger SA s are more gender accepting and familiar with other genders as it is part of pop culture

I ve admitted to panties for me on VS online chat
I think they already are familiar with it

Pat Scales
Pat Scales

It is interesting that in my male life as a husband, father, professional all around guy I am virtually fearless. I have a crash through walls personality and nothing causes me any concern at all. I will take on any task or challenge and do my best to prevail.
The idea of walking into a VS store and asking for help in picking out a bra for myself scares the living daylights out of me.
Go figure.

Darcy Bainsley

I’ve had this positive experience from another store I shop at. Unfortunately VS doesn’t sell bras my size. So I shop elsewhere, but if you become a regular it makes the experience so much more fun. The get to know you, what you like, and love to help you.

skippy1965 Cynthia
Trusted Member

I’m inspired by this story and others like it! I think I’ll set a goal of trying this myself before the end of the year! Thanks for writing it!

Maxine Doos

You and me both, Cyn 🙂
Tina Rose

I’m so glad you had such a good experience there. It sounds so familiar. I went my first time to the VS semi-annual sale, fully aware that I was out of place that day, but just as determined to see it through. Now I go regularly to a nearby store, where they know me by sight and by name. They have seen me change since that first time three years ago now. I am no longer out of place. In more ways than one.

April (Pacific Princess)
Active Member

I have had only good experiences when shopping and trying on clothes in guy mode. Most sales people will help you. Last weekend I tried on several dresses, tops and ladies jeans at a thrift store and at a Ross. I always get just a touch nervous around other guys in the store, but never around women. I do 90% of my shopping for feminine attire when presenting as a guy; it’s just never been a problem. But when you do get a very helpful salesperson it’s even a more fun experience! Thanks for posting this Maxine! April

Sara Thomas
Sara Thomas

I’ve also been out bra shopping several times but as a man. I wear a size 38d and I went to Soma in the mall. And the sales lady treating me very respectful as she knew it was for me. And she help me pick out my bra without asking I found a nice pair matching panties. As we were talking and she asked me if I wanted anything else and I said I like to get a tunic. She said we’re about the same size so she went and Found Me one and I love it. Ended up getting… Read more »

Patty Phose
Trusted Member

I’ve been buying my own pantyhose since I was 13. I’ve received help several times from sales people. If they would ask if I needed help, usually I knew what I wanted, but there have been times when I liked a brand and style of pantyhose but I wanted it in a larger size or different color. Sometimes they would ask if they were for me. It wasn’t exactly a secret because usually when I went shopping for pantyhose, I was wearing pantyhose with short shorts. They would often look through drawers and stock rooms to see if they had… Read more »

Tina Allen

I have had great experiences buying bras for myself over the years. Earlier this year I checked out a specialty bra shop on one of my business trips in Michigans’ UP. I went in looked around at all the pretty stuff they had. The of the saleslady asked if I needed help finding a bra. O course I said yes and told her it was for me. I told her the size I needed, 46DD, and she said that many stopped at 44, at least in the styles I preferred. She said I may try on some to see how… Read more »

Amanda Patrick

Amanda P Formaly ( Margaret ) I got tired of the hit and miss of internet shopping. So I decided to step out and purchase in stores. I called ahead first to a shoe store, a hair salon that I knew sold wigs I even had it cut and styled there. and also a bra store. I called ahead and explained who I was in advance and was welcomed at each place. the bra store sales lady even told me about a lgbtq friendly place in a city about one half hour drive from where I live that welcomed everybody… Read more »

Maxine Doos

Great to hear that you had a wonderful time, Amanda.
And wonderful to hear your experiences here have helped with your confidence. 🙂

1 2 3 4
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account