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For me it was shopping at the Outlet shops in the Pocono's.
First time out I went to a bar to watch my friends band. While sitting with his wife, she t old me that her husband also dresses. It came as quite a surprise because we had been good friends for several years and neither of us knew.
First time out, over 13 years ago, I was visiting a dressing service, as I had no clothes, makeup, or makeup skills and wanted to attend a Tri-Ess meeting as what I then thought would be a one-off experience to add to my list of new things tried. I had never met a crossdresser, did not know I even WAS one, but didn't want to make a 600 round-trip drive just to observe, but to experience what it would feel like. After getting dressed and made up I was expecting no more, but the proprietor ushered me out the door, and directed me where to take her. Before I knew where we were going I was being asked by a valet at a fancy French restaurant for the car keys. In shock, I replied in my male voice, then struggled to exit the car in heels I had never worn and had no clue how to handle. It would have made a great Candid Camera video! The next morning she had me drive to a Macy's realized the door entered the dress section, our apparent destination, so immediately sought refuge by ducking behind racks as she scouted out dresses and beckoned me to the changing room. I picked out two dresses which have stood the test of time and remain among my favorites. Not wanting to show male ID at checkout, I paid cash. After that was a Chik Filet full of teens. By the time I eventually got to my meeting that night I had numerous "firsts", most of which caught me, and perhaps others, totally by surprise, looking like a deer caught in headlights..
The real first time that I was dressed in public was in my neighbourhood late at night, but that wasn't a poll choice.
I hadn't said anything to my wife about what I was doing, so when she slept, I got a bright dress and stuck it under my armpit, to avoid my building's security camera. Can't be too careful. It was warm, so I wore comfy sandals, found a dark enough area to hide, then changed, and started wandering around local streets with bare legs while carrying my drab clothes. My god there are too many people in a big city driving or walking around at 2 in the morning coming from all directions! That's scary for an inaugural run! Not sure when I will do that again.
Otherwise, my first experience during the day was in a mall. Not so scary in a crowd, I guess.
my first time in a blue dress at a support group dinner in a public restaurant
Four years old mum dressed up as a lady for a fancy dress competition. I won, got a prize and loved every minute.
First time presenting fully en femme was at a wine bar with my wife and another couple. It was very busy on a Saturday evening. We me them at Santana Row in San Jose, CA. One of the members of the other couple worked at this wine bar and was working that day until 5pm.
It was a lovely evening! Also had to get the courage up to use the ladies restroom for the first time that night. Lots of stuff in a day...
Have fun out there
xoxo
Rayna
None of the categories fit my first experience, so I did not check anything.
My first experience completely dressed as a female was at five years of age, when I served as a flower girl at a wedding. How this came to happen is a very lengthy story, but it did mark my first experience being completely dressed as a female. Prior to five years of age, I had already been showing an interest in many female things, such as wearing my mother's high heels, playing with her cosmetics, having older relatives paint my nails, etc.
Several of the above. Last week, had my first makeover in Las Vegas . I drove to the hotel, checked in and strolled to a restaurant and bar. Then went window shopping. After Amy had worked her magic on me, was totally at ease. It helps to have other sisters with you, and be out in a town like Vegas where you don’t stand out, but are just a part of the “ circus”.
Hi Lanna I've only ever been out En Femme in my car, I always went out late at night because no one can tell that I'm a crossdresser in the dark, I've been out about 3 or 4 times dressed up, one time i parked up in a town not far from where i live and went and did some window shopping, there was no one about and it was wonderful just to walk around feeling so feminine X
Hugs Rozalyn X
My first time out was to a large state park. I walked around a few areas where there were people picnicking and sat by a lake for a while. Got to feel the breeze blow up my denim skirt for the first time!
The one year anniversary of that day is coming up on May 5th and I'm going to put on the same clothes and go back to the park to celebrate. I now live virtually my entire life dressed as a woman so it's been an amazing year.
If wandering along a beach at night in Perth or Adelaide, Australia counts, I guess that would be it. But that was close to 40 years ago and also quite possibly a silly thing to do. =Woman? alone at night alone on a beach? "BTW" My job involved a lot of interstate and overseas travel, so thats how come I was in the above cities on a regular basis.
From my viewpoint I regard my "starting point" as attending a CD group meeting in Perth, again, a very long time ago. The location was out past the airport and I used to stay at the opposite end of the city out by the beaches. (See above). So I got up lots of courage and drove there and back dressed...
But again that was at night.
Since those "good old days", I progressed to going to dressing services in the UK and Canada and going out femme from there to either night clubs, or in one instance driving from Plymouth down to Cornwall (Many "tales of my exploits" can be found in my articles and photos on this wonderful site)
Locally, (Covid notwithstanding) , I get out 2-3 times PA and go bra or normal clothes shopping or out for dinner. Have a big "anniversary dinner" coming up next week. Fingers crossed it all comes off OK.
Not exactly one of the choices, so I choose the mall. I went window shopping in our downtown main street at night. It was quite busy and I was nervous at first, but after passing the first few people without a second glance I settled in and had a lovely walk. I have been out many times since, and never had the least issue.
None of the above. My first time was right in my own neighborhood.
My first time out was at a museum, but that wasn’t one of the choices offered. So I chose grocery store, because that’s where I went the second time. Close enough, I suppose.