Out and about: cherry popping tranny on the loose

Star date August 2014
So we (my wife and I) did it. We finally inflicted Daniella on an unsuspecting public for the first time. Wow, what fun! The evening was a crossdresser/transvestite/trans person/drag queen etc (all protocols observed I hope) friendly party held at a local (gay) club/bar. It was therefore a friendly place to go to for a first time, shy and nervous girl.
The evening was a real clandestine affair; there may be a future for us in military intelligence after all. We got home at 7 pm after a family oriented event. I showered, did a final hair removal and face shave. We then waited for the babysitter to arrive. We said our goodbyes etc and went to the (unoccupied) guest flat on our property where I had stashed my kit and got dressed, painted nails, and did make-up and hair. My wife went to get the car and I locked up and waited outside. At that point disaster struck! The babysitter came out to see why the car was moving (she had expected us to be gone by then and was afraid someone was stealing the cars). I don’t know if she saw me or not as I beat a hasty and slightly wobbly retreat, into the shadows, in my stilettos. Oh well, no point crying over spilled milk.

Pictures taken just before we stepped out the door to go to the car:

First night out
First night out
Cherry popping tranny
Cherry popping tranny

We drove to the venue which took about 10 minutes. I was expecting police roadblock with full body searches at every corner (police road blocks are a feature of life in South Africa), but it seems the South African Police intelligence gathering regarding first time crossdressers inflicting themselves on the innocent public is woefully (and thankfully) inadequate!
We arrived at the club and parked the car we could see a few people who were also crossdressers standing outside the club and that made me feel better; I was very keen to get in.
I got out the car as elegantly as I could (hopefully I didn’t flash the security guard: Paris Hilton has my sympathies) and in we went.
I had made contact with a few of the attendees on Facebook beforehand and they recognized us right off. They were welcoming, friendly and supportive of both me and my wife. I have seldom been made to feel so much a part of a new group of people so quickly. We got drinks and chatted (I probably bored them all with my story of the babysitter, but I suspect they all remember their first time and appreciate the stress involved).
We danced, we talked, we walked around a bit and danced some more. It was great! There was another crossdresser’s wife there so my wife had company too which was very nice.
There was a self-confessed ‘tranny chaser’ (really not sure about that term, it feels somewhat pejorative, but there you go) at the club who looked me up and down but kept his hands to himself, not sure if I should be insulted or not?
At around 11-30 my wife had developed a headache and was not feeling too good (loud music is not really her thing), so we left. I could have stayed as I did not want the night to end but we are in this together so we walked through the parking lot greeted the security guard and got in the car as elegantly as I could.
My wife drove us home and once again the police’s intelligence gathering proved to be far from adequate as we arrived home unmolested.
Once we pulled in to the drive way I reluctantly pulled my jeans and jersey on over my dress, took off my wig and earrings and replaced my stilettos with street shoes. I walked into the house and made a beeline for my bathroom while my wife relieved the babysitter.
My wife and I spoke lots about this on Sunday night (first chance we had) and we both had so much fun! We are up for it again and are looking forward to more adventures.
It was so good being out dressed and being accepted for who and what we are. I do have to work on my presentation skills and especially the behaviours; it is easy to ‘lapse’ into male behaviours.
I appreciate going to a (gay) night club hosting an evening for crossdressers/drag queens etc isn’t quite the same thing as shopping, eating etc in ‘general public’ but it was still a big step for me. There will be more such adventures to follow I am sure.

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3 Comments

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  1. Awesome first time out. I may have to do a write up on my first time out. There is never anything quite as interesting as that first time. Loved your story hon.

    Ever & Always,
    Caden Lane

    Liked by 1 person

    • Thanks Caden… It was a blast and a very positive experience setting us up for further fun times. I am very lucky to have such a supporting wife, such a great group of trans friends who advised us and I was fortunate to have had a good time. For many others, their first time does not go well.

      Liked by 1 person

      • I know, over the years I’ve read my fair share of horror stories. I was so racked with fear that first outing. And it was a daylight outing at a Disney World resort no less. Some might argue I was setting myself up for failure. But I adore Disney, and the idea of combining two of my favorite things seemed like a Holy Grail moment. It went awesomely. So I am thankful for that.

        But the horror stories lead me to create a local crossdresser Sorority in order to help newer sisters find their place, find support, and have reasons to be social and go out dressed. I also distinctly recall those years of hiding behind my front door. Racked with fear of stepping out of it. If i can help any sisters to learn to accept their feminine aspect, to love this side of themselves, to not feel guilt or shame, and to experience being out and about as their femme self, then I feel I have accomplished truly noble goals.

        Ever & Always,
        Caden Lane

        Liked by 1 person

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Damon Ashworth Psychology

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Luna Ribbeck

Crossdressing

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