A Tale of Two Cities

In the words of the so many kid’s novels I read as a child, “it all began” late last year when my beloved partner announced she wanted to do a “girls trip” to Europe; river cruise, bus trips, flights hither and yon, etc. etc.  My immediate reaction was, “oh, how nice to include me,” but of course, given the home front situation that would not be possible!

So I thought I would go in the opposite direction to Canada and the USA, where from my working days I had friends and also family now residing in “middle America.” One of my favorite North American cities is Toronto, home to Paddy Alridge’s “Walk on The Wildside” transformation boutique. So for many a moon, emails went back and forth in the hope I could reprise the makeover I had there roughly 20 years ago. It was also one of my first “outings,” to a female impersonator show.

A major objective this time was to have Paddy do my make up and then go “Caty” shopping in some of the big Toronto department stores; and I had the 27 kgs of male and female luggage to prove my intent. This had all been set up with the relevant personnel in those stores and they were lovely.  All very tolerant and accepting.

Sadly, when I finally got to Toronto, I was still very tired and jet-lagged and it was still very warm, (ie. 26C) on my shopping day and Caty needs stacks of body hair coverage to appear “right.” My makeup would have lasted five minutes under all that lot. So I had to cancel the makeover and shopping trip. Though I still went there and bought some clip on earrings.

Not to be daunted by the lack of lovely lingerie”souvenirs, aka my main reason for going shopping, I went to both stores in Vancouver on the way home and more than made up for the Toronto disappointment.  Gorgeous bra and panty sets, especially from the Hudson’s Bay store

However, to paraphrase some other well known words, “all was not makeover lost,” because when I got home well before my beloved, there was ample time to go to Ophelia Williams’ “Cross Dress with Class,” in a Melbourne inner suburb.

It was my second makeover with Ophelia and whilst the first one last year was wonderful, this time around we went one, (well SEVERAL)  better. Last year it was just for the day, a walk in the park, then a twilight drive home as Caty.  All great stuff.  The walk in the park happened all over again this time, too.

This year an overnight stay close by her residence was organized and therefore allowed much more time to tick the as yet not achieved Caty boxes.  To wit, 1) go shopping as Caty, 2) try on some dresses in the change room, 3) one of a CD’s ultimate fantasies, a “visit to the ladies” in the shopping centre and 4) go out to dinner that evening.

Well folks, Caty “cracked it for the quaddie” (Australian slang for backing four winning horses at the one race meeting) and did the lot. All the while the wonderful Ophelia was there snapping away with my camera and the photos attached are living proof.

I opted for the “corporate look” black skirt and jacket with a mixture of a blouse or top under the jacket.  Underneath of course was my very best lingerie, with the Canadian souvenirs a must.

The whole experience was just wonderful and when it was over, I wanted to do it all over again a.s.a.p.  To feel the weight of my attached breast forms being held so well in a comfy bra, the heels clicking on the shopping centre tiled floor, perfume wafting around my face, suspender tabs holding up my stockings.  The stuff a crossdressers dreams are made of and of course, feel so much a natural part of every one of us.  As those who can and do do it state, it’s all a matter of confidence and making sure you appear as natural as possible.  Dress and act like any female would when she is out; avoid eye contact when you can and if you cant, just smile and keep moving.  Oh and of course, have your feet facing the right way in the ladies!

But sadly, reality gets in the way of such feelings and after a nice dinner in the Thai restaurant not far from Ophelia’s home, it was back to my room and a night in Caty’s PJ’s, and then home next morning.

That location, that suburb, that huge Westfield shopping centre, that “local small shopping strip” with the restaurant….… Until my divorce in the mid 90’s these places were all my “locals” and given my that ex hated my cross dressing with a passion, there is considerable irony here.  After leaving Ophelia’s for my accommodation, Caty even drove past her former “abode.”  The bins were out, lights were on, so “she who always thought she should be obeyed” was home.

A knock on the door at 8.30 pm was but a passing, but very delicious thought!!!

I reckon I can do one makeover a year with Ophelia and will more than likely reprise this one, but the next “CD mountains” are the Transformal conference in New South Wales in May next year and another go at the Seahorse Ball in Sydney in August.

Til then,

Happy dressing.

Caty

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Caty Ryan

"Mature aged" crossdresser living in Victoria, Australia Love all things feminine especially classy lingerie and formal gowns. Have a long standing passion for period wear and own twp lovely replica period gowns, a 1700's and one American Civil war replica. Love to chat via e.mail with anyone with similar interests

Latest posts by Caty Ryan (see all)

• A CD “Daily Double” Bra Fitting and Dinner out, Part 2 - June 30, 2023
• A CD “Daily Double” Bra Fitting and Dinner out - June 7, 2023
• Bra Shopping “My Cups runneth over!” - July 8, 2022
• Nighty Night Nightie!! - June 13, 2021
• Domesti(Caty)ed - April 15, 2021

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