[Philosophy] ‘How not to be seen’, or failing to deal with the FEAR.

I had a wonderful encounter this week with two gloriously beautiful people and it’s got me thinking about what I do, or more importantly, what I don’t do, and why I don’t do it.

Yeah, difficult sentence that one wasn’t it? Stick with it, it’ll make sense.

But first, what happened.? Well, I was in London on work, staying over for three days, and I found out from Cindy at Boys Will Be Girls that two of my online heroines were coming into town from distant lands (well, Scandinavia) for a long week of fun. Going to reveal a little revelation here, but I have never, until this week, met another cross-dresser enfemme in the ‘real world’ whilst being in drab.


Pictured – don’t give me that look sweetie, you know it’s the truth

I know. How on earth did I get to the age I am without managing that? Turns out I’ve led a sheltered life (by design actually). But I couldn’t pass up the chance of meeting these two ladies; coming off the back of a brilliant session I was suffering a little from the drabs and wanted to live vicariously through someone else.

So, I contacted one of the girls on Instagram and mentioned that Cindy had said she’d be in town. Hint hint. And, bless her, the girl in question kindly offered to meet up for a drink on Tuesday night.

I immediately went into panic spiral. What would I say? Would I come across as a creep? What on earth was I doing?


Pictured – I’ll ask myself multiple questions about something as simple as meeting friends in a bar, whereas dressing and posing like this is second nature. Figure that one out….

I ruminated about backing out all of Monday and Tuesday. In fact I had to have a little Dutch courage just to leave the hotel on Tuesday night, three pints of Dutch courage to be precise, before girding my loins and jumping on the Tube to Charing Cross.

The ladies in question had had a fun night out, drinks, the theatre, and were finishing their evening by meeting me in a pub called The Admiralty neat Trafalgar Square. Unbeknownst to me they had got out of the theatre early and were waiting in the pub when I walked in, nervously heading to the bar and missing the eager wave from one of them.

So why am I writing this blog post? Because they were gorgeous, wonderfully friendly and so much braver than I could ever be. I was literally terrified to meet them and I didn’t know why.


Pictured – nothing to do with the text, I just love this look πŸ™‚

It took another pint before I calmed down a little, but they were both so friendly I felt a little ashamed at myself for my worries. Here I was, wearing the drab armour I hide behind on a day to day basis, and these two gorgeous creatures were sat opposite me just exuding style and femininity.

Steffie was bubbly and vivacious, a natural and beautiful girl who was just friendliness incarnate. Anna was just as gorgeous, quieter with a lovely accent, but just as friendly, funny and engaging, and I warmed to the pair of them and came out of my shell very quickly.

We shared fun stories of Cindy sessions, I asked them about their day and the fun they were having, and the time quickly flew by. We must have been talking for only an hour, but it felt like I had known both of them my entire life.

About thirty minutes into the conversation an excited pair of young girls, Russian i think, quietly interrupted us and asked nicely if they could have a picture with Steffie and Anna, ‘because they were so beautiful’. I sat quietly on my side of the table as the girls took pictures with the ladies while Steffie and Anna were nothing less than brilliant, hugging, chatting, before the two girls headed off with selfies on their phones.

I had to use the toilet a couple of times, a combination of the six pints I had rapidly consumed in the space of ninety odd minutes to bolster my confidence and my encroaching old age (cough). Anna went to powder her nose, and when she came back Steffie went to the bar to buy a round.

I found myself entranced and amazed at what was going on. I watched Steffie at the bar, the epitome of style and confidence, standing amongst slightly tipsy men as she talked to the barman before returning with the drinks. She was almost glowing, and I found myself suddenly a little sad at my own attitudes and fear.

And this is what this blog is all about. Somehow I’ve cornered myself into a position where everything about Sarah scares me.

I talked to Anna about my worries of being out and about dressed while Steffie bought the drinks, and Anna said she was a little scared as well. The irony of this was she was sat there looking gorgeous and I was wearing the same clothes I’d worn to the office a couple of hours earlier. It was lovely of her to say that but she was in a different league.

If I’d been dressed and girls had come up asking for a picture I would have literally caught fire. When I was out at the Wayout the last time I went to the bar to buy a round and it was a terrifying experience, standing feeling helpless in a queue at the bar where everyone else were slightly drunk and lecherous, at least that was what the paranoid android in my head was whispering, while my dress hung around my legs, my heels hurt and I tried not to make eye contact with anyone in case they said something unpleasant to me.


Pictured – terror. I had to sit there for thirty minutes to get the courage to step around the back to where the bar is.Β 

What the hell is going on in my head?

It took meeting two of my personal heroines to make me realise that I’ve become too scared of something that should be wonderful. I’d have given anything to be in that bar as Sarah with Steffie and Anna, but the thought of that gave me (and still gives me) the chills.

So, what am I scared of? I’ve actually backed out of going out a couple of times recently because after I said I’d do it I spent the next couple of weeks worrying about it, to the point that the session I was going to have was getting spoilt because all I could think of was what could happen if I was out on the streets of London as a woman.

I’m sad to say that it is something completely within myself, and indicative of the way I was brought up. I need to change this – I had an enlightening conversation with the man who was meant to be taking Sarah out on a date before I bailed on the idea. The guy in question is also one of us, but was willing to go out to Covent Garden with Sarah on his arm, and was talking to me at my last session. His supposition was brilliantly simple, honest, and accurate, and just highlighted how confused my thought process was.

He said that people under thirty are ambivalent towards the trans community. They are understanding and to them it’s part of normal society. It’s only people of my generation that see this kind of behaviour, which is wonderful and empowering, as somewhat wrong.

All of my worries are self-directed. Amusingly they are also a little vain – my worry is that people will look at me, judge me, abuse me. In reality I’m not that important and, given the fact as I always say that I’m a little tall, I’m the last cross-dresser someone will have a go at.

So is it cowardice? No, not really. It’s just another side effect of a broken upbringing and ‘thinks-too-much’. As I sat in the booth in the pub and watched and listened to the two women sat opposite me, because they were women, laugh, talk and say lovely things about Sarah and her style, I realised how repressed I’ve become.

And it’s got worse over time. The first time i went out I spent an entire afternoon and evening walking up and down Brick Lane in a gorgeous red dress and heels. Second time out I went to the Wayout in full retro with my best friend. Third time I went to Wayout in a modern frock that got a lot of handsy attention. Fourth time it was the lovely floral 1940s frock.


Pictured – that was my look for the second time out. A little provocative?

And each time I’ve got more and more terrified. Yet nothing has happened untoward at any of the outings, aside from some lecherous and drunk admirers.

I was only with Anna and Steffie for about an hour, but it was almost a life-changing experience. I have found myself thinking a lot about the fun they were having, and wanting to experience that myself.

I just need to control this fear. If only for Sarah.

So huge thanks to the lovely Anna and Steffie for an unforgettable and hopefully life-changing hour or so. Think I fell in love a little bit with both of them and I can’t put into words how wonderful it was to bask in their glow. I think it’s time to find my own again.


Pictured – two beautiful women and one terrified idiot.

Stay beautiful people, and realise those fears that stop you being the person you should be are just fears, nothing else. And maybe I’ll even start to believe that sometime soon….


Pictured – try to imagine her between the two beauties above – that’s what I’d like to see and experience without the panic…

5 thoughts on “[Philosophy] ‘How not to be seen’, or failing to deal with the FEAR.

  1. Sarah I completely understand where you are coming from with this post. I’m so pleased that you were able to meet Anna and Steffie. πŸ™‚ They are amazing role models and wonderful inspirations!
    And remember that while your forays into the real world as Sarah have been good and less good experiences; you have still managed to be brave and get out to show her to the world. And that is an amazing thing. πŸ™‚ I long to be able to do the same but I’m not sure if it will ever happen. Meeting other like minded girls when they look feminine and fabulous and you’re in drab is surreal. I managed to meet half a dozen gorgeous girls late last year in a pub near me. They all looked fantastic and I was stood there looking sheepish in a scruffy t-shirt and jeans and a baseball cap. πŸ˜• And how I wish I could have been dressed as well as them!
    I think that if you asked Anna and Steffie that on their next visit here, if you could possibly join them for an evening en-femme, they would probably say yes. I’m sure with the support of Cindy you will look as equally at home out and about as Sarah as you do with the other face you present to the world. πŸ™‚
    Stay safe and keep being you sweetie. πŸ™‚ 😘

    Liked by 1 person

  2. Sarah,

    Anna and myself were delighted to hear that our meeting had such a positive impact on you. I was near to tears reading your blog as I sat in the airport waiting to fly home. Meeting you on this trip was a highlight and I can speak for both of us when I say we instantly took to your warm and humorous nature. Regardless of what clothes we were wearing, we could have been old friends meeting up again…and that was after just 1 hour in each others company.

    It goes without saying that I would love to spend time with Sarah and I suspect we have a very similar sense of humour. Confident Sarah and Stephanie could unleash hell on the male world πŸ˜€

    That opportunity will only come with you feeling comfortable and that is my only objective. When you are ready, I will be more than happy to take you to lovely places where elegant ladies can dine, laugh and have fun with no concerns.


    Liked by 2 people

  3. This Massively resonated with me Sarah, I love reading your blogs as I think we are very similar people, with one major difference…….
    You are MUCH braver than me, I have not been out en femme, had a makeover, or met any other girls. I would love to, but the thought TERRIFIES me!
    I admire your bravery and love to read your thoughts and adventures!
    Jen x

    Liked by 1 person

  4. Sarah, what a wonderful narrative. I love your fashion sense, your wit, your transparency and your writing style. I’m a fan.
    I imagine your meeting with Steffie and Anna would be like me meeting you in Boston, stomach all full of butterflies. You are a star in your own right!
    I hope that you reach a point where going out as Sarah is easier. Dare I say, comfortable. You’re a brilliant lass, and probably a right hoot to hang out with.
    I enjoy every post.

    Liked by 1 person

  5. Life is way too short honey, go for it!
    You will wonder why you were so worried. People are way too busy looking at their phones to even notice us let alone react to us.
    Believe me everything is better in a dress.
    I have just discovered you and your blog Sarah and am looking forward to learning more of you and watching your coming out so to speak.
    Get at it girl.
    Janny xx

    Liked by 1 person

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