Crossdressing leap for womankind

I had recently bought some new high heeled court shoes and they just had to be tried out! Nothing quite right in the wardrobe so nothing else for it – just had to buy another outfit! (Red bodycon dress with a matching peplum waist jacket – totally lush and I actually have curves thanks to weight loss and waist training!). The local trans/cd/tv support group was due its monthly meeting and I fully intended to give my new outfit an ‘outing’. Pun fully intended as this was also going to be the first time ever I planned to fully dress at home and then go out en femme.

As the date approached I had everything planned out, my family were all going to be out so I would have total privacy to take my time over preparations. Then of course it all changed! My lovely granddaughter who was going to be at work was sick! Of course I felt terrible for her but at the same time was thinking drat! Now what can I do? I still wanted / needed to go – building up the courage to step out was not easy and if I faltered I may not be that brave again for a while. Hell I had even bought a handbag for the occasion! I couldn’t let that go to waste! Lol

Ok, so change of plan called for. I couldn’t fully dress at home so had to choose an outfit I could hide under my clothes. So, after making sure she was OK I prepared as best I could. Not the relaxed, take your time, carefully planned ensemble and makeup I had in mind but instead my fave black leather look skinny jeans, black sheer blouse with lace neckline and long lace sleeves, corset, (still working on that waist training!) a pair of fantastic padded butt pants that also are tight enough to tuck everything away!, hold ups, favourite bra (with my girls ready to be added when then coast was clear!) I packed my new shoes, hair, jewelry and makeup in a bag, and then had to put my jeans, sweatshirt, coat etc on top so I could say goodbye as I went out the door.

Not quite the First Stepping Out I had planned!

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OK, so far so good, I have at least managed to go out partially dressed even if covered up! Next problem, how do I finish the job ideally before I arrive at the meeting? Only one thing for it – change in the car park! What a nightmare! so self-conscious as the car park is very well lit and busy! Still, I found a relatively quiet corner (after several attempts and changing levels – I dread to think what car park security thought if the watched this on CCTV!!!).

I never realised just how tricky it is to get undressed in a car! (ok, maybe I have done it before when I was a lot younger but that’s a totally different story!) Even more tricky was trying to do my makeup using the tiny mirror in the visor!!! It’s hard enough in a well lit room with a large mirror but this was ridiculous! Still – determined to plod on as I had come this far and was determined not to quit now.

One Giant Leap for Womankind

Eventually I managed to throw on a face that I hoped would at least be passable! So now, fully dressed and made up I was ready to go – OH NO – I forgot a coat and it was pretty cold out and the venue was a 5 to 10 minute walk away. I only had my male mode fleece! It would just have to do – I couldn’t go back home to get a coat.

Since getting the new shoes (shiny black court shoes with a 3.5 to 4inch heel shoes 11UK for those who are interested :-)) I had been practicing in them at home as much as I could and I thought I was pretty OK at walking in them. That was until I now realised that I had to walk from the car park, through a shopping mall, and down the street to the venue! All of a sudden that 5 minute walk seemed like one small step for man, one gigantic ‘run the gauntlet’! for a man in heels!

Still, taking my handbag over my shoulder, and a shopping bag containing my other stuff in my other hand I set off, bravely facing the unknown, uncharted territory that stretched out in front of me! This is when I found there is a big difference between walking in heels on a flat and carpeted floor, vs walking in heels over a bricked path (load of cracks), drain covers, pot holes, curbs and all those hazards that you just take in your stride (groan – I know another awful pun) when walking in male shoes.

All I can say is that my respect for all those who can walk in heels and make it look graceful has grown exponentially! After what seemed like an eternity, conscious of every person I passed, every group of girls talking in hushed whispers as I walked by, every person walking behind me and getting closer, I finally made it to the meeting.

This is where my faith in humanity was fully restored, They are such a wonderful group of girls and supporters that I was able to relax straight away, and feel totally safe and secure no matter how I looked. I am so happy I found this support group and hope to make some long term friends there.

P.S. Maybe the red dress will get an outing next!

EnFemme Style


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skippy1965 Cynthia
Trusted Member
6 years ago

What a wonderful story. I an identify with several parts of it-especially the changing to women’s clothes in the car in a parking deck(! (See my post within the first time out forums pg2 scrolldown til you see the phrase Keys are the key! .

Other similarities included the sudden change in what had been a careful plan! Thank you so much for sharing your story I hope it gives others the courage to take that first step out!


Georgina (or Georgie)
Georgina (or Georgie)
6 years ago

Cyn, I just read your story, I can now totally relate to your experience and know just how you felt at the time!
I have seen many similar accounts of First time outings and pretty much all of them say it gets easier!
Can’t wait for the next chance, hopefully it won’t be too long!

PS: my car has the keyless entry and ignition so they can be buried at the bottom of my handbag and I can still use the car, so one less problem to worry about!

Take care

Rosaliy Lynne
Rosaliy Lynne
6 years ago

hey there Georgie Girl – you did great. OMG walking in heels over cobble stone paving – I walked the Vegas strip on several occasions in heels – big mistake – worse since I actually did it twice. Heels get caught in every crack and crevice.

Never had to change from boy mode to girl mode in the car but changing any clothes in a car can be a challenge. Still, YOU did it and survived !!!! WTG GIRL !!!

Stephanie Q
Stephanie Q
6 years ago

This is a wonderful article! It really illustrates how unknown factors can result in a drastic change of plans, and what you have to do to recover gracefully.

Thanks for contributing as an author!


Georgina (or Georgie)
Georgina (or Georgie)
6 years ago

Thank you all so much for your wonderful comments of support and encouragement. I am so glad I shared my experience with you all. I hope it shows that even when things don’t go exactly to plan you can still shine through and have a fun time! This experience also gave me the perfect excuse for a new pair of Cuban heeled ankle boots (much better for walking on uneven surfaces!) and a gorgeous flared coat with an asymmetrical cut (higher at the front to show the skirts and stockings!) Always look on the bright side, be positive about the… Read more »

Vicky Whitney
6 years ago

Really sweet account Georgina … what a pretty name. I know just how you felt. Been there several (too many) years ago.

I got read by a mischievous young man who insisted on commenting ‘look at the pretty girl with his little titties’!

I was so embarrassed until I reached the hall where all the gurlz were getting into their dresses.

Little did I know they had a big room to get dressed in with make-up mirrors and all … but I would not have changed a thing that night.

Georgina (or Georgie)
Georgina (or Georgie)
6 years ago
Reply to  Vicky Whitney

Hi Vicky, I am sure many girls have been through similar episodes, I hope this might encourage other ‘first timers’ to bravely take their first steps too!
The venue I was going to also had changing facilities but I wanted to arrive as Georgie, not change on arrival. I saw that as an important hurdle to get over, and despite the setbacks I made it!
PS: thanks for the nice comment on my name, I have always liked the name Georgina or Georgie and it just felt right when I first named my inner woman.

6 years ago

Your story shows great strength and resolve. Too many people would have just taken it as a “sign” that they weren’t supposed to go, and just stayed home. Good for you for following through! Experiences like that will only make you stronger and more determined to live the life you desire.

Georgina (or Georgie)
Georgina (or Georgie)
6 years ago
Reply to  Ashleigh

Ashleigh, I didn’t feel particularly strong on the night, more a case of dogged determination and ‘I am not going back now!’ was what kept driving me on to complete this personal goal that I had set myself.
We in the trans community still have to battle prejudice and fight for acceptance, but some of this is our own fears. I battled my fear that night and came through, I will try again, and hope to build up more confidence as my fear subsides.

6 years ago

I wear 2-3″ chunkier heels all the time in male mode. All that I do is buy fem jeans in a longer leg length to cover the heels when I walk. On the inside of each pocket I write the leg length so that I can match the heel height. Ie: my normal leg length is 30″.For 2″ heel it is 33″ and I write with permanent marker inside the pant 33″. For 3″ heel it is a 34″leg length.

Christy Hunter
6 years ago

What a great story and fantastic attitude! There is so much inner courage you need to take that step out. I have been underdressing for years outside the house and I am almost at that next step. The support here is giving me the push to do it. It’s stories likes yours that make me believe I can do it!


Georgina (or Georgie)
Georgina (or Georgie)
6 years ago
Reply to  Christy Hunter

Christy, believe me and believe in yourself, you CAN do it! And you won’t regret it. I believe in life you need to ‘carpe diem’ and it’s better to regret the things you have done rather than regret the things you never did but wanted to! I have since taken a few more baby steps, a full makeover service, fantastic time and so amazed by the results! And I have also gone shopping for clothes in the shops rather than via the ‘safe’ anonymity of on line shopping. Haven’t gone shopping in girl mode yet but I think I can… Read more »

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