[Philosophy] Twas the night before Sarahmass

Warts and all I’m afraid. I’m currently lying on a hotel bed in London, on the verge of two mega-days of Sarah time with the sublime Cindy at BWBG, but it’s an odd one to be sure.

For a start, it’s 18:14 and I’m both utterly shattered and mildly (r.e. happily) drunk. Today’s task was get myself, and my very heavy bag full of gorgeous frocks and accessories, from my house (not saying where, just West until you hit Wales), to the hotel room in central London without a: failing to get here or b: killing anyone in the process. Boy, the second part of that statement was hard today.


Pictures – I mean, look at all that masculine rage. Cough.

For a start my phone provider, O2, decided to have a complete system meltdown. Ericsson, a key software provider for O2, kinda forgot to update some critical certificates in their software installs, ones that expired. And boom, suddenly O2 (and various sub-customers) no longer have a 4G network. Bye bye any data connectivity via phone. That made downloading and activating my tickets from Trainline to my phone…….interesting.

Secondly my Credit Card was exposed, probably from a dodgy website (not dodgy dodgy but ‘we can’t be arsed to secure your data’ dodgy) resulting in some little oik spending 2.7k on it before the credit card company worked out that me, someone who only ever uses it for Amazon, Netflix and, err, Sarah frocks, wasn’t spending a grand at a roofing company in Banbury, or going to the cinema at Carrick twenty times.


Pictures – one of the charges was 900+ quid at a baby supply store. I had to think about that for a bit before denying it. And before you worry, the object in the picture is a ‘training baby doll for new mum’. 😉

I had the usual sinking gut feeling when I found out but having talked to the Credit Card firm all is sorted, at least the account is locked, new card on the way, etc etc. Although it was very amusing going through the purchases. Amazon? Yes, mine. Carrick Cinema? Absolutely not. Lindy Bop? Err, yes. Vivien of Holloway? Hmm, yes…..


Pictures – 13 orders from Vivien of Holloway? Err, yeah, that was me….

So, chuck those two little fun things together with absolute minimum sleep (four hours since Sunday and counting) and I’m a little, well, wiggy.

So, where did we come in? Oh yeah, I’m sat cross-legged on the bed in the hotel, Led Zeppelin (IV, currently playing Battle of Evermore) on the phone speaker, the heavy bag of Sarah-ness in the corner of the room awaiting tomorrow’s fun, couple of beers (well, like LZ, four) consumed, not going out because, wow, London is bad at the best of times but during Xmas party season it’s a bloody minefield of drunken idiots and loud shouters.

Of course, to get into the mood for tomorrow I’m wearing a frock and have sprayed some Chanel No.5, but it’s been a long day so I feel that’s a little luxury I can afford myself.


Pictured – this very frock, which I’m hoping to model tomorrow with a Beehive hair-do, make it a proper 60s girl look…

One of the dichotomies I find about the whole Sarah experience is that I love the pictures, I love the experience of taking the pictures, not too keen on the process of makeup (I’m impatient and to be honest I just want to subsume instantly into the role, not gradually fade from him to her), but the prep for the whole thing? A bloody nightmare.

And this is one of the things I’m finding really hard about all this. The prep, the logistics, the sheer hassle of it all is starting to overwhelm my pleasure at the result. I’ve got a mind that won’t let me enjoy something until *everything* that could get in the way has been addressed or put to bed – put it this way, I’m in the hotel right now, and I can’t look forward to the session tomorrow because I need to 1: sleep, 2: shower, 3: shave the face fuzz, 4: work out how to get the massive bag of goodies to Cindy’s place, 5: stand at the doorway having pressed the button waiting the eternal seconds for her door to open. All I’m doing at the moment is worrying about those things as opposed to looking forward to the point at which the camera flash starts to go.


Pictured – enjoyment. Not pictured, the 48 hours of hassle beforehand getting there….

And wind it back a bit – I’ve spent the last eight weeks regretting every meal I’ve had in case I put on a bit of weight and can no longer fit into a size 18. Literally every meal. I’ve promised myself I’ll exercise to keep the weight down, and when I can’t due to work or, as has been the case for the last couple of weeks, just feeling worn out and ill, I’ve thought it the end of the world.

That’s not a healthy way to live. But it’s understandable, and to understand it you need to look at what this thing is all about.

I’m not a transexual. I don’t have the urge to change sex, never have had. I don’t have the compelling urge to present myself as a woman to the world, I couldn’t get away with it if I tried and what I do, with Sarah, isn’t really about that. It’s all about me, or rather it’s all about being someone who isn’t me.


Pictured – not me. Which is an odd thing to say. Because it is me. Sarah. 

I had an abusive childhood, made much worse by the fact I was a sensitive and intelligent child. The result of that upbringing which I’d really ignored and blamed myself for until I had a wonderful chat with my sister a couple of weeks ago, who is as beautifully damaged as I am, is that I have almost zero self-confidence in myself. And I have terrible body image issues – I chose a look for myself back in 1984 to protect from bullying and I have just kept the same look since – long hair, jeans, t-shirts, trainers. Period.

Sarah is the other side of me, the person I couldn’t be, biologically and confidence-wise. She can wear anything (within reason) and, without being modest, she rocks some styles that blow my mind. She is the reaction of myself to not being able to express anything other than a shell. She is the antithesis of me, an opposite in almost every way.

And that’s the point. I’ve always said she is my steam valve, and that she is, but it sometimes feels at the moment that I’m having to sacrifice too much, health, eating, peace of mind, stress, in order to satisfy the rare moments I have as her.

But, as I’ve said on too many occasions, I suffer from depression (see shitty childhood for that as well) and at the moment, well, let’s just say the Black Dog has a permanent kennel setup right next to my pleasure centres.


Pictured – a pussycat, just to annoy the Black Dog….

The other side of this is that I over-think everything. I remember a wonderful conversation I had with someone I respect a lot on Facebook, another one of Cindy’s girls, and she berated me and took me to task in the most loving way as to my reticence towards going out dressed. I went on for ages about fear of discovery, fear of being put in a situation, fear of what people would think of me etc etc. And she said, bluntly but nicely, that all I was doing was ‘wearing women’s clothing’. And to a certain extent she’s dead right.

Times have changed and cross-dressing is, dare I say it, almost trendy now. It’s accepted, a lot more than it was even ten years ago. But the point from my perspective is I’m not just wearing women’s clothing. For a start, ‘him’ doesn’t have the confidence to do it. When I dress it is all in, if there’s an inkling of him in any of the visual side of the outfit or pose in the pictures I hate it. She is all about subsuming him, she is complete escapism.


Pictured – absolutely no sign of the overweight, middle-aged, angst-ridden male idiot.

The problem I have at the moment? The logistics and effort to get him to her is too much, too tiring, too invasive. If that’s down to expecting too much from ‘her’ time, over-thinking it and letting the planning overwhelm the result then that’s ‘his’ problem.

Either way I need to bloody chill. So, tomorrow, and Saturday, are pure Sarah sessions and I am just going to relax into them and see what happens. I won’t fret in advance about every pose, every smile, every hand gesture. And I think, conversely, that may bring out more of Sarah than I’ve seen before.

Plus it’s wonderful to live in a time when first world problems are the only thing you need to worry about.

Anyway, thanks for sticking with me through that one, I needed a vent. Hopefully the plethora of pictures of her in pretty outfits made the blog more palatable. To make up for it as soon as this is published I’m going to have a serious gush on my favourite producer of clothes, and a personal role-model and, dare I say it, crush of mine, Vivien of Holloway, because it’s only 19:25 and I have fourteen hours to kill before the process of burying him under the layers of makeup, underwear, slips, petticoats, shoes and finally the frocks can start, and I can be her, if only for a short while. Fourteen hours. Hell, that’s almost six more blog posts if I didn’t sleep…..

Stay beautiful, stay true to yourself, and listen to what the inner voice has to say, sometimes it can change the way you think for the better.


Pictured – I’m lucky my inner-voice has such nice cleavage…..


2 thoughts on “[Philosophy] Twas the night before Sarahmass

  1. Hi Sarah, x
    I just want you to know that I think that you are an amazing person! You tell us when you are having a fabulous time and also share with us when things aren’t going quiet so well.
    I understand how things are for you with work pressures. Your workload seems to have increased exponentially! And that is bound to have a knock on effect.
    Tell me I’m being silly but have you thought of spending a longer time as Sarah? But possibly with longer gaps in between as ‘him’? It’s just a thought is all. It would be more immersive and probably give you more preparation time too.
    Have lots of fabulous, feminine fun over the next two days sweetie! 😘😘😘XXX

    Liked by 1 person

  2. Hi Sarah. It’s hard to think of you being epressed when I see you wearing such beautiful clothes – especially the gorgeous chiffony one at the end. Would it make you feel any better if I told you that you are the envy of many of us CDers – an idol, almost. If I could look as good as you I would be the happiest ‘girl’ in the world! I also agree with you about the lovely Vivien. Not only does she produce the most fabulous dresses and skirts, but she’s mighty cute too. I certainlywould – so join the queue!
    Sylvie xxxxx

    Liked by 2 people

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