Baby Steps (but steps all the same).

Well, I did it!

Today, inspired largely by a lot of the advice I've been reading in here, Wendy-Lyn went out (briefly) into the world for the first
time ever.

Pretty scary, but I loved it!

I had under-dressed with navy lace-front panties, black bralette and black cami, then changed in the car into a black-and-white
skirt, black top and tan sandals and a cheap but serviceable wig, slipped my 'jiggly-bits' into my bra and then went for a
drive, taking a coffee and a sandwich with me.

Sat in the car near a park and had lunch while watching some kids play cricket. Drove on a bit and was about to get out and go
take some pics, but a group of young blokes arrived and, since I can't pass I once more moved on. I was pretty sure I was 'made'
by the young blokes, but they didn't know me IRL so I wasn't too fazed. While I do look a bit MIAD, I don't look like ME (but I
just hope no-one spotted Wendy-Lyn driving my car. :P )

I finally found somewhere I felt comfortable getting out of the car, so I walked around for a bit, answered the call of
nature, and shot a (too) short video. I exported some stills off the video to keep as pics.

It was only a short outing, and didn't go entirely as planned, but all-in-all I'm so relieved that I finally got the courage to get out of the small unit I live in, where due to the very close proximity of neighbours and the risk of friends dropping by I can
only dress late at night.
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Excellent start, I'd call those toddler steps myself. It'll get easier the more you go out but don't get carried away, small increments still as you gain evermore confidence.

@Helen_Highwater

That's my plan, yes.

The first time for anything is always the hardest, and since it didn't end in disaster or shame/embarrassment
I feel more confident for next time, but I won't be going overboard.

Thanks for your kind response, I do appreciate it.

Good for you, it is a big step getting out the first time. You will find it easier each time you get out, just be aware of your surroundings at all times. Don't go anywhere a "real" woman wouldn't go alone.

Good going, girl. I am finding myself in a similar place, daring to take baby steps like receiving food deliveries at my door while wearing an obviously padded bra under my drab. Baby steps, but steps nonetheless. Please keep us "abreast" of your progress.

Epic outing, Wendy-Lin, and great job not losing courage when surprises arose. I wish you many more of these exciting (and relieving) outings!

Wendy-lyn, Congrats on your first step.

That's my world; short drives and evening strolls. I will drive to a quiet safe neighborhood that has grocery stores, shops and restaurants for my evening strolls. I love the fall and winter because darkness comes early when men and women still are seen coming home from work or going to a store. It's enough to satisfy the itch. After about a half hour of strolling the outing does become somewhat boring. These forays into the wild are within my comfort zone. Due to height and size it would be obvious to anyone around that I am a MIAD. Even though most people would ignore me or give me a stare that is enough to wreck the peace and comfort I do get from escaping into Stephanie's world.

I hope you will be able to expand your world outside your home.

One small step for a woman...
That's the way to do it. One foot in front of the other and keep moving forward.
Good for you.

Every journey starts with that first step. Believe me it gets easier every time.

That is a great start. I drove out to a monument my first time dressed. I don't know how I would have reacted if some guys were in close contact. I was afraid to go near anyone my first few times out.

I actually felt really strange wearing a wig for the first time, ever - and i wasn't
overwhelmed with the resulting look.

It's only a cheap and crappy wig, but is my first.

But I've been playing around with it, and this afternoon I put it into a pony-tail
and not only does it now feel/look like the hair I had as a teen, but it really does
remind me of my late younger brother. I had dark brown, almost black hair, he
was a red-head.

I miss him.

When I was riding my motorcycles I always had my hair up in a ponytail like this
so it wouldn't tangle, but now my real hair is short and very grey :'(

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Well done Wendy-Lyn. The wig is the element that gives me confidence. I went out quite a bit at night without one at first (even had a moustache) and, though I loved the feeling of wearing high heels and a dress, I knew I couldn't hope not to attract attention. I don't think it's necessary to pass, but you can move about very freely in daylight if you have a complete look. Not to mention the confidence your disguise will give you. So add a ladies jacket of some kind or a cardigan, a handbag, maybe a bit of jewellery and of course makeup and the fear of being seen will be much reduced.

Another thing I realised is how much better I look when I pull the wig behind at least one ear and mostly off my forehead. A couple of clip on earrings complete the look (anybody observant
would know I've been out as the sideboards are temporarily gone). So yes, I think the ponytail looks way better as well.

One last thing that surprised me is how lovely it is to wear girly colours. I find that my entire girly
wardrobe is either pink or a colour that goes with pink. And it never ceases to amaze me how comfortable I have become in that colour. Yet if I was given a pink pullover for Christmas, I'd probably never wear it.

Anyway well done again Wendy-Lyn. Enjoy the excitement of pushing your limits

That's just wonderful Wendy, I am so happy for you! I too cannot wait to do the same and that day for me is coming very soon! I am glad too you chose that photo of you for your avatar. Very lovely dress!! May I ask where you bought it?

@ Linda K.

It actually came out of a large bag of clothing I was given to donate to a local Care group.

I sorted thru it to make sure it was all clean and serviceable, and fell in love with this dress.

Here's a better pic.

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It is a wonderful dress with a 40's look to it. I always loved those types of dresses and have been looking to get one for myself. Unfortunately, I cannot find one in my size. So I will keep looking. That is a very nice dress though!

Well done. The most difficult thing is stepping out the door and closing it behind you🙂

Wendy-Lyn, Good for you girl, I love the dress and wig!

Good for you. The first time I went out in public dressed I wore a scarf over my face.

Good on ya, mate!

With my wife being an Aussie, I generally (non-Covid times) spend two months of the year in the Melbourne area. I've been out a number of times the last two years I was there (2019, early 2020), and I didn't have any issues, especially in public. I've been downtown Melbourne, taken the trains, gone to a concert, no problem. Also was a regular at a Dangerfield store (love their clothes) in downtown Melbourne (opposite Flinders Street station) and they enjoyed having me visit.

It does get easier as you do it more often.