The first part…

As the stories of our childhood used to state, “it all began” when I realised that April 2023 marked ten years since the wonderful professional makeup artist, Michele “R”, had done her first makeover on me, at a block of self-contained apartments in an inner suburb of Melbourne.

There have been quite a few makeovers in the past. In places as far apart as Toronto, Canada, London, UK, up in the Blue Mountains west of Sydney and in dear old Sydney itself.

But the April 2013 makeover was very special. I wore my “Lady Catherine” replica 17th-century ball gown and Michelle made me look like a “High-Born Lady of The Court” aka “Bridgeton!”


Not to mention, a couple of classy three-piece “Mother of the Bride” ensembles and my first-ever full-length, dark blue, formal evening gown. (Which I recently gave to another CD… Boo.. hoo…. it doesn’t fit me anymore.)

What better way to celebrate than by having Michelle make me up again and go out for an “anniversary dinner” IE “One leg of the double.” In the ten years since 2013, Caty has become an adventurous old “bird.” Back in ’13, it was all I could do to sneak out of the apartment in darkness and drive the 120k to my then, rural home.

These days, when time and seasons permit, (remembering that “crossdressing is a winter sport”), she is quite comfy about “going public” in almost any situation, except for anywhere alone on a dark night.

Michelle readily agreed to my suggestion of an anniversary dinner at a restaurant in a middle northern Melbourne suburb. (Sadly, as much as we tried, could not find one that allowed BYO wine… Caty has a good wine collection, but it had to stay untouched.)

The second leg of the “daily double” arose from browsing the net and finding that a lingerie store, roughly in the same area, that freely advertises bra fitting for men—crossdressed or otherwise.

After two false starts, we set a date for Wednesday 10 May, but with so much preparation and travel required, I booked two nights at the same apartment chain; Michelle lives close by this location.

So day one, I checked in, got all of Caty’s gear unpacked, then promptly drove home for the rest of the day and night. The reason being, in as much as I hate the “porky pies” I have to tell my beloved, a one-night overnight stay is easier to explain that a two night. (We have a “DADT”) about Caty in this house. Plus, I had lots of private time to make sure my “bod” was as hairless as possible. Nothing destroys the “M2F” image more than body hair in the wrong places.

Visit Transgender Heaven

I packed everything needed to be Caty in case Michelle could not make it. Otherwise, I would have paid lots of $$ and not been able to get my value for them.

On day 2, it was back to the apartment. Once shaved, showered, and dressed in my lingerie, it was time for Michelle to arrive to do my “day makeup.” I had previously given her my wig, so she could do both hair and makeup.

Day wear was an Arianne bralette and panties, plus Essence (NZ) Cami and 40 denier black tights, with a white blouse, gray boucle knit drop waist cardi, and black below knee skirt, plus a pair of black flats for shoes.

Michelle carries her own collapsible makeup chair. I sat back and once again loved that wonderful, (very femme), feeling of a professional doing your makeup. The entire process takes almost two hours and at the end of it all, when dressed and made up, I felt just plain “bloomin” wonderful!

Down to my car via the lift with the half-length mirrors, (wow, is that really ME!!). Then off to the bra fitting. Ah… the old “Driving when dressed” bit. Seat belt between “my breasts” and feel my arms rub up against them as I turn a corner. Sadly, no “false nails in full view”, I can’t get the “blighters” to stay on these days. Only small sips of water, to eliminate the need for “the ladies”. But with a “suitable container” in the car, “just in case”

Visit Transgender Heaven

Last July, as per my Professional Bra Fitting, My Cups Runneth Over CDH article, I had a fitting at another store in Melbourne’s outer South East. And whilst I loved every minute and bought a lovely “SP” black bra and brief set, the fitting room was only big enough for one person. So, I missed out on the “full disaster” of a fitter being in the room with you and helping try on various bras.

So, with head up, chest out, shorter stride, handbag under one arm, slowly swing the other one, look straight ahead, do not make eye contact unless the “other person” does first, I headed to the store. BTW, no one took the slightest bit of notice of me. Just another woman out and about going shopping on a Melbourne autumn day. In contrast to when we wear male jeans, the slight breeze up my skirt felt great too!

My fitter Tracey was busy with other clients, so I spent some time just browsing all the lovely frillies with a keen eye out for a “Triumph Amourette” underwire bra in my size and style. (My lovely CD friend Dani has a gorgeous black one and I’m ever so jealous)

But soon I was in the fitting room, with the Cami and bralette around my middle, and Tracey fussing over me by bringing various brands and coloured bras and assisting me in trying them on. AHHHHH the “full disaster”. “No, your 18 band is too tight” and “the C Cup is gapping at the top!”

Nature Day 3

In the end and much to my surprise, given I’ve always bought 18C sizes, we did the old sister size bit. Up a band and down a cup. I have a slightly larger set of self-adhesive forms and I was concerned about the future fit with those, but a later try-on at home allayed the above fears.

They did not have the matching brief in my correct size, but I took the plunge and bought the next size down. I was much amused when I was invited to try them on with my existing “unders” still in place.

In the overall excitement of the event, I completely forgot I had my camera in my handbag. Otherwise, there could have been a few pictures to remember it all by!

Fitting completed, new Linga Dore “Daily” bra and briefs purchased, and out into the world I go. Could not leave without walking down “Memory Lane,” Aka the street where the building was located where I spent the “formative years of my nearly four-decade business career. Back then I probably would have even avoided walking past the lingerie store, let alone go in for a bra fitting!

Though, in later years, after another makeover/femme evening dinner out close by, I remember window shopping the same store…

Back to my car and apartment for a glass of leftover red and a nice meat pie for a late lunch. Then a 45 min “nana nap” to be ready for Michelle to come back and touch up my makeup for the evening out.

To be continued…



More Articles by Caty Ryan

View all articles by Caty RyanTags:
5 1 vote
Article Rating
Inline Feedbacks
View all comments
Lorraine Lowry
Active Member
10 months ago

Thanks for sharing with the other girls.

Trusted Member
10 months ago

Caty, I love your writing style and humor.. thanks for sharing your “daily double” ..BTW
You look maaahvelous!!! Leonara

Denise Little
10 months ago

Caty, thank you for sharing, you look gorgeous!

Tiny Tinkerbell
10 months ago

what a lovely start to your adventure outing…can’t wait for part 2….thank you for sharing, Caty…!!!

Would love your thoughts, please comment.x
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?