In November last year, I wrote an article called ‘The Evolution of Lucy’, telling my story from the last few years. In it, I mentioned my first venture out as Lucy in December 2022. As a result of that, several girls asked me to write about the event, and so finally, here it is.

I did briefly make it out in October 2022 to a drive-thru Starbucks, but I didn’t class this as my first trip out as I’d not done what I set out to do, which was to go inside. I began to make plans for a “real” trip out. In the run-up to Christmas, I’d be on my own as my wife would be away collecting the mother-in-law for the holidays. This became my planned time to venture out.

I decided that before this date I needed to return to Starbucks, this time going inside to get used to being seen out before attempting anything more adventurous. Sure enough, I headed back there sometime in November, but when I arrived, I completely froze and went through the drive-thru again. I drove home on something of a downer.

As the December weekend approached, my confidence levels were plummeting. I had plans to park at a shopping area on Saturday afternoon and walk around, maybe going for a coffee. I wanted to repeat the process on Sunday somewhere else.

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Would I or wouldn’t I though?

As my wife headed away on that appointed Saturday morning, I had tasks to do during the morning and planned to go out in the afternoon. Well, the afternoon came, and I found more and more tasks to do. It was almost 3 pm, and I realised I was leaving things to run a little late.

I decided to test the water by going to Starbucks again, (see if I had the confidence to go shopping on Sunday.) For the third time, I headed to Starbucks. As it was a December afternoon, it was turning dark by the time I arrived. I got out of the car, stood nervously for a moment or two, and then just went for it and walked in. To my delight, the place was fairly quiet. Two tables were occupied, and no one was at the counter.

With a slightly shaky voice, I ordered a latte and a muffin. The girl behind the counter was perfectly fine with me. As it was Starbucks, she asked my name for the coffee; for the first time ever, I gave my name as Lucy out loud.

At a table, I removed my coat and sat down. I was wearing a purple cord skirt and some matching woolly tights, (as I have quite hairy legs.) I became more confident as time went on. As people came in, it didn’t concern me. I had plans to go to a Next store where there were some shoes I’d been viewing online that were in stock.

En Femme Style

I was usually happy picking women’s shoes and clothes from racks and buying them in drab, but had never taken the opportunity to try anything on. It was 4:30, Next was 20 minutes away and open until 5:30. Why not just go in and try them on? So that’s exactly what I did…

The store was in a busy retail park. It was dark outside by the time I arrived. I strode inside confidently and wandered around browsing the ladies’ items. When I’d previously done this in drab, I always felt a little odd, but this felt wonderful.

I eventually found the shoes and sat down to try them on. They were Mary Jane style shoes. I had to concentrate when fastening up the buckles, so I didn’t sit with my legs wide open. After all, I was a lady in a skirt!

Walking around a little, they seemed to fit, but the tights I wore were far thicker than the ones I would normally wear. This left me with a dilemma as to whether to buy them. I resolved to put them back and return the following day wearing sheer tights. I  left the store empty-handed and drove home.

I couldn’t believe what I’d got up to! I’d “only” intended to go out for a coffee, but felt as if I’d done far more than that. When I arrived home, as it was dark, I just exited the car in full Lucy mode and went into the house. I changed, but stayed in Lucy mode all evening, and overnight.

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The following day, I needed to be out all morning meeting some friends for a dog walk, and it was in boy mode until lunchtime. As a result, once again, it ended up being later than intended to get ready to go out.

This trip was to another town centre with a mostly outdoor shopping area. I wanted to get a gift card for someone for Christmas from a coffee chain called Café Nero.

It was quite a vile day with strong winds and rain. I wore trousers so I could wear sheer tights to try on the shoes. I’d had the foresight to buy Lucy an umbrella but decided that the strong winds would make it redundant, so I had to wear my normal waterproof on top.

I arrived at the open-air car park and set off into town. When I reached Café Nero and looked in through the window, I was horrified. It was extremely busy, and there was quite a queue at the counter. My confidence drained, and I made to walk away. I stopped, looked up at the rain, and thought,  “What the Hell” and I walked in.

I made my way to the counter not making eye contact with anyone. The queue was particularly slow-moving, but eventually, it was my turn. I ordered coffee and then remembered the gift card. I asked, in what I hoped was a softer version of my usual voice, but they were sold out.

I chose a seat at the far end of the café, with my back to the wall, to see everyone. I took off my waterproof, put down my handbag, and sat down. While I drank my coffee, I noticed two ladies at a table in front of me. The younger one had her back to me, and the older one faced me. She glanced at me every so often. I’d meet her eye contact and she moved her gaze back to her companion. I was feeling quite confident again by now.

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After a while, I looked at my watch, time to get to Next before they closed. The shopping area was quieter, and the echo of my fast-moving block heels was the only sound I heard as making my way back to the car park. I made it to Next with 15 minutes to spare. I strode straight to the shoes and tried them on again. Like Cinderella, they fit perfectly!

While I was walking around in them, a lady came around a corner close to me and looked directly at me. I felt like a rabbit caught in headlights. She just smiled, said Hi, and carried on. I was amazed, there wasn’t a hint of amusement in her face, it was just a very warm smile.

I’m pretty darned sure she made me. I’m also sure that she wouldn’t have smiled at me in that way if I’d been in boy mode. I figured I’d just been treated as a woman by another woman. It felt great!

Eventually, I took the shoes to the counter and paid. The young guy behind the counter was perfectly professional and even wished me a nice evening. Once again, I drove home feeling on top of the world.

So, ladies, it can be done. If the thought terrifies you, it’s quite normal.

As I write this, I haven’t been out for a few months, and the thought of doing it again still terrifies me, but I know for certain that I will.

Lucy x








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Catharine Connall
Active Member
16 days ago

Thank you Lucy, wonderful story and experience it sounds like.

Stephanie Browne
Active Member
14 days ago

Just bought a frilly pink and mixed color dress. It came today, and I admit I was excited when it did.
With.anticipation, I tore open the package. The dress is beautiful and soft silky to the touch.
Looked at myself in the mirror many times , and got that wonderful “pretty"
Feeling, I so love In ❤️ womans dresses and skirts.

.I think I will take Stephanie jewelry shopping tomorrow in my new frilly

Anna Redhead
Active Member
14 days ago

@Lucy Bancroft That sounds like a wonderful experience and a huge boost for your confidence

Olivia Crighton
14 days ago

Wonderful article Lucy and I admire your bravery at those decision making times to just go for it and walk into the shop. I have been going out shopping and various places as Olivia for 10 years now and still get those moments of should I just run back to the car so those doubting moments are a normal part of this brave new world you have stepped into. It took me a long time to have the courage to sit in a coffee shop and drink a coffee after I started venturing out as Olivia so for you to… Read more »

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