Xpressions Christmas Gala, Oakville Nov 2021.  by Amy Myers

This was an event I’d much anticipated and until a few weeks ago it was still in doubt due to this ongoing and ever changing pandemic, which caused this and most other things last year to be cancelled.

We held it at the same location as before, the Sandman Hotel in Oakville. They do have good facilities and if one doesn’t need or want to go outside at all, there is a Denny’s attached for breakfast and lunch, then the Chop House for dinner. For those in need of more activities there are exercise machines, and a pool too.

The last time this was held was two years ago, and I was only able to go to the Friday night dinner, so missed all of the Saturday fun. Also being what might be called a “New Girl” at the time I had never been to one of these events, so I was doubly looking forward to it this year.

Nature Day 3

We live only an hour and bit’s drive to the hotel so an easy drive and I arrived in femme mode. I mean why not, that’s what this weekend is for, if not to be able to spread one’s feminine wings! The strange thing is when you book with your male name and show up looking like a woman, well so what unless one has a credit card in your femme name, which I don’t.
By now I’ve had several situations like this and it has all been taken for granted. The young woman who checked me in then asked if I was part of the fashion show on Sat night, to which I replied, Yes!

I know some folks don’t like the hit TV show by Rupaul, the Drag Race, and for sure it’s not my style, but it certainly has brought male to female cross dressing into the current popular culture, which has to be a good thing.

We had several hours till dinner so we chilled out for a while, changed and then headed down for dinner. I had about seven different outfits for the weekend and wanted to wear them all.
The food was fabulous, though the service was a bit slow and it took well over 2 hours for dinner. However, we did get to enjoy the company of old friends and made some new ones too, which is really what this is all about, other than the opportunity to live femme for a couple of days.

Saturday I dressed in a different outfit again for breakfast then our Club’s AGM, to which all members are invited and a couple of the new girls joined in, which was great to see.

Crossdresser Superstore

After some discussion about how to increase participation in our events, it was time to fill some empty spots on the board, first we voted in our current president, April for another term. Kudos to April for taking on this role once again.
With Cynthia and Nancy returning as Vice President and Secretary respectively, and my own Sweetie wife, Glenda who graciously agreed to take on the job of Treasurer.

After all of that it was time to get ready for my makeover with Brandi, who is actually a hotel employee Monday to Friday but is also a qualified makeup artist and does that on weekends.

For the first time I had fake eyelashes too! What a difference they made, though truth to tell, I thought they looked a bit strange on me at first but loved them once I got used to them.
I must try to do this again for myself.

She also did an amazing job of redrawing my eyebrows and making them look a lot more feminine, without plucking or shaving, so the end result was fabulous. A good makeover is so nice to have done, and it makes you feel so much more feminine.  She did 5 other girls that afternoon too, so who says you can’t get lucky on a Saturday afternoon!

Then we did some shopping, which was great as I felt like I was on cloud 9 being out and about with the great makeup job.
We wandered around some stores, though many in the nearby outlet mall have closed as a result of the pandemic.
Still there was Laura’s, La Vie En Rose and a few others to explore.


As it turned out we didn’t buy anything at the time but I was taken with a top at Laura’s and went back on Sunday before we hit the road.

Now that is another (short!) story, and another small first for me.
I had been intending to travel home as Amy, and either change in the backseat (who hasn’t done that from time to time?) near home, or slip into my detached garage to change, but my daughter had picked up my son the day before who was then staying at their place, which was only a 20 min drive from the hotel, so I had to be in guy mode for the trip.
So that’s how I went into the Laura’s store. Now I have shopped in drab before with no problem, but this time I wanted to try it on to make sure of the fit

The young sales woman was great when I told her I was shopping for myself, and let me use the change room. No prejudice detected at all. Amazing how far we have come.

Then a coffee and a bite to eat with some chill out time before dinner. Then on with the long grey and gold dress, the matching heels, a few touch ups to my makeup and off to the banquet hall for dinner!

On the same weekend most of the guests staying there were part of a boy’s hockey tournament and as we neared the banquet room a Mom who was taking her young daughter to the pool stopped us and asked why we were so dressed up. I explained it’s a Christmas Party Gala for a group we are members of.  She complimented us effusively on our dresses, and said she wished she could come too! I had to wonder what she would have thought if she had joined us. Now I had been floating a few inches off of the floor all day long, and I’m sure you can believe that put me a bit higher.

En Femme Style

The meal was buffet style and excellent overall, the food was fresh, and tasted great.

Next, one of the founder’s and Vice President, Cythina got up to make an announcement and give out the Miss Xpressions award. This is given out annually to the member of Xpressions who has worked hardest for the group and this time our President, April, received it. April has worked very very hard to keep everything going during these trying times by keeping in touch and setting up dinners, pub nights, now the Friday night socials, etc. Honestly, I can’t think of a more deserving person either. The honor involves a beauty pageant like shoulder banner and a tiara to wear! Lucky Lady!

Then it was time to get prepared for the “work” part of the evening, being a model for the fashion show! We had made arrangements with Mirella from the boutique in Burlington to put on a fashion show as the main entertainment for tonight. There were four of us scheduled to model, April, Cynthia, Claudia and myself, with 5 outfits each, except for Cynthia who only had four.

All of us had visited her shop a few days before to make selections and check the fit of the dresses for the evening. We didn’t have a change room in the banquet room so we all had to troop along the hallway to Cynthia’s room to change. Cynthia’s wife, Christine held the fort there and was on hand to help with zippers and to make sure we looked right before we left for the banquet room to show ourselves off.


It was quite a scramble to get our outfit off, a new one on, hike along the hall, do our parade through the room, then repeat! Despite the “work” of it all it was a lot of fun for us, but more importantly from what we heard later, everyone seemed to really enjoy the show. For those of us who love beautiful clothes, I could simply say,”What’s not to like”?

So a great deal of thanks goes to Mirella for lending us these fabulous clothes to wear, if only for a few minutes. She was also on hand to provide commentary about each outfit, and to keep everyone entertained during the gaps.

We were nothing like professional models, but in a way that was part of the fun for us and everyone else as well. For myself and Glenda it was a wonderful weekend and for me personally a time to live the pink fog for 2 1/2 days. Except I think I’m still in it!

Lastly, but not least by any means, a huge round of thanks must go to everyone who put all the hard work in making this weekend happen, as well as those who came and enjoyed the togetherness.

For those who have thought about this, but have never done it, give it some extra thought for next year and join us for a wonderful weekend. Can’t wait for next year!

Thank you girls for reading my article and hope you had as much fun reading it as I had writing it!

With much love, Amy




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Amy Myers

I'm 60+, hetro, married, and love dressing up! I keep saying and feeling like I'm new to this, but I have dressed from time to time since my pre teens, but just late 2018 it seems to have become of a bigger part of me, rather than just a role I played from time to time. I'm interested in music, cars, photography, and plus other interests.

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2 years ago

You make it sound like so much fun, Amy. I am definitely envious.

Michelle Last
Active Member
2 years ago

Where was this event held?

Michelle McQueen
Michelle McQueen
2 years ago

Wow! What a dream weekend! Thanks for sharing.

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