Amy meets the World, or at least a small slice of it.

Like so many others here, crossdressing has been a mostly solitary pleasure of mine, from pre-teen to off and on through the years. I am fortunate in having a wife who didn’t mind my dressing, but it was only an occasional thing, and not at all extensive. At times though, I did wonder what it would be like to shave my beard and get all made up, but it wasn’t a demanding presence in my mind, not like it is has now become.

Late last year, I was smitten with dressing, and then I started looking around online and found this site. I was so terrified of joining up, actually backed out of signing-up three times, but finally did, and that was one of the best things I did, maybe the best with regards to dressing.

So shortly after joining the Canadian Ambassador and another member, who both live in this general area, they told me about a local CD group called Xpressions. They meet up a couple times a month. My response to this was like, “Thanks girls, maybe sometime in the future,” meaning months and months down the road. Though I was thinking it would be neat to go out en femme, I was still coming to grips with the demands of my femme side, as in, the guy in me not wanting to give up his beard. After all, the beard had been rather like a trademark of mine for going on 40 years. I didn’t really want to be the “Bearded Lady” of side show fame.

Koala Swim

Through a few emails and pm’s with the two girls here, I got more curious about meeting other CD’s and actually being out in the world… a tiny, little bit anyway. Part of the rules for that group is that you don’t have to be a member of the group to attend this particular event, and one doesn’t even have to dress up for it. Also, for those whom cannot dress beforehand for some reason, there’s a private upstairs washroom (women’s, of course) where one can change. I was assured that whatever form I chose to present myself as, I would be accepted. That was very reassuring and seemed sincere.

At this point, I’d made up my mind to attend, but dressing was another thing. As I turned it over in my confused mind, I felt that if I went there, then I HAD to get dressed, no two ways about it! Besides, being the only one in drab in a room full of CD’s and GG’s would be a bit strange, too. Not having the courage, or at that point experience to dress and then drive the 2 1/2 hours, I chose to bring my femme clothes along and change there. I was so nervous at first, but then settled down as I settled in to the long drive.

My worries about the city’s terrible traffic and searching to find parking led me to be almost two hours early!! Even so, I still had time to stop at a crossdresser friendly supply store and buy a few things, such as my first wig and foam breast forms. Not the greatest, but better than the socks I was currently using, and just as important, bought within my budget. I wandered around window shopping as it were, until the time to go approached. I headed back to my car, and the nerves hit me again. Big time now! I worried about crazy things, such as: was I in the wrong place, what if no one else showed up, what if I wasn’t accepted, etc., etc. Keep in mind; I was still sporting a full beard! The meeting place is in an area of the city known to be a bit of a gay village, which at least makes the area one of the more accepting ones to be in. Not that it mattered much, as I was still in drab!

I finally went in, still early, and looked around, gym bag in hand and feeling pretty weird, worse than a first date! After looking so lost, a group of women sitting at a table I’d walked past a couple of times looked at me and asked if they could help. Well, that was that, I had found some fellow Dresser’s!

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I was shown the private room where we would be having dinner and then the washroom where I could change.

So change I did, but OMG, what a time I had of it! The cubicle was so small and narrow with nowhere to really put anything. All of my clothes, both male and female kept falling onto the floor as I put on pantyhose, bra, etc. No makeup or nail polish; by now, I was even more uptight and nervous that I could barely finish dressing. I finally felt ready and gingerly walked downstairs to join to rest, still not very accustomed to wearing women’s shoes.

Once in with the others, they made me so welcome that my nervousness soon lifted, and then after a time, I found I was actually enjoying myself! I met the Canadian Ambassador, who was so nice, the other girl who invited me as well. All the others made me feel very welcome and SUPPORTED. When it was time to get ready to go home, I changed into my male outer clothes, but stayed in my femme shoes, and then slipped my forms in when I got into the car.

To say that evening was a success for me, is a bit of an understatement, and it made me hungry for more!

I think that the reason this went so well was due to a few things. Firstly, the two ladies here that gave me an introduction to a CD/TG club, and then the group being so accepting and kind to me. The venue certainly helped, being in an accepting part of town, and the ability to change on site, as the group had a private room also made things go smoother. The few staff and servers that were there treated us all as if we were just normal patrons, which ultimately, we were. Plus the distance from home I traveled made it highly unlikely I’d meet anyone from my own town there.

Even though those circumstances were extremely important, the most critical thing was inside of me. For some reason, I was ready to take that first, a very tentative step out into the world as Amy. I really didn’t have the appearance to “pass,” in normal company yet. As most of us can’t seem to explain our motivation to dress, I also can’t say what drove my decision to meet the other girls, except to say, I’m very, very glad I did.

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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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Olivia Livin
Trusted Member
2 years ago

You’ve come a long way baby! From your tentative shopping days to now, holy. I would love to meet up with the group as well, it’s the drive part that bothers me. Perhaps as things settle in the fall we could go together.

Olivia Livin
Trusted Member
2 years ago
Reply to  Amy Myers

Thanks Amy
Its the ongoing support from so many within this community that gives each of confidence to try or do certain things and its awesome to see just how often that gets paid forward. The meets ups you attend are an excellent example of that.

Rochelle Mills
Active Member
2 years ago

Wonderful story, Amy. So glad you took the step to meet up with other CDs/TGs. That’s always a refreshing experience!

Stephanie Flowers
Active Member
2 years ago

Amy wasn’t it a wonderful time. I really enjoy meeting you back then and now you’ve certainly done well for yourself and have embraced your femininity beautifully and the confinance. Losing the beard was a good thing and you look fabulous. These evenings with the gathering of so many amazing ladies I do enjoy and feel so comfortable there and always anticipating when I can do it again. I enjoyed being there for you and those emotional feelings that were running through you that night bought back my night just months earlier . Same venue as I walked into the… Read more »

skippy1965 Cynthia
Trusted Member
2 years ago

Congrats Amy.. You will be amazed how quickly your confidence grows! And Steph Flowers-congrats to you too and awesome job mentoring! Now get her to go to Keystone next March lol!

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Jezzebelle Sanchez
2 years ago

What and where is keystone

Paula Malmborg
Active Member
2 years ago

great story, this just gives me more courage to go out thank you

Alicia C
Active Member
2 years ago

congrats on the brave steps. soon it’ll feel natural… like when I was wandering s dept store and +wanting+ to be in gurl mode to shop for some new clothes 🙂

Daisy Marie
Active Member
2 years ago

Congratulations Amy!
It’s a very important milestone to any crossdress, but it is as pleasant in the end as confusing at the beginning.
The most important thing to point out is that you didn’t give up due to your initial fears and didn’t quit the opportunity to enjoy a new adventure in your life. That’s inner growth!

Stephanie Ontario
Active Member
2 years ago

Hi Amy, What a truly inspirational story! I have so wanted to join Xpressions and your detailing of the evening, meeting the girls, the trials and tribulations of the dressing lounge was awesome. I hope I can find the courage to do as you did, and join you and the other ladies for drinks / dinner one evening. The crazy part of my ‘story’ I just went to Additionelle, this morning at 9;30 AM and purchased in drab mode a beautiful faux leather dress that the sales clerk knew was for me. Apparently I can shop for myself but not… Read more »

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