[Fashion] An Archival Cheer-Me-Up

There are times when it goes right. And there are times when it doesn’t. The last week has been…..not fun at all. And that’s a bloody understatement,

See, I had a double session planned, my first since early December. The week before the planned session I had a mad runaround time with work and real-life, combined with the after effects of Storm Dennis which left where I live pretty much twinned with Atlantis due to six metres of river rise deluging Hereford, which combined with me having to be places involving driving and me being absolutely bloody petrified of driving in floods (due to almost wrecking my previous car, a cool Toyota Celica Sport-T that I took for a swim in a pool that used to be a dip in a country road, flooding the engine and scaring seven colours of faecal matter out of me) meant I got insomnia big time.

So the week leading up to my session was fraught at best, and I found myself really craving the feel of stockings and the taste of lipstick. Fast forward to last Monday and I woke up at 3:30am to start my trip to the train station and found my right eye wouldn’t quite open. I’d had a cough for a couple of days and just put it down to sleeping oddly on it, cleaned it, grabbed the massively heavy bag of frocks and accessories and drove to the station.

Spent the day in work, the bag carefully pushed under my desk so no one would ask me why I had a backpack the size of an army exercise for one day at work, and my eyes felt very tired, but put it down to, well, being tired for a start. A couple of people commented that I looked a little glassy eyed but I was dismissive as I was a: looking forward to two days of pure Sarah fun and b: my freshly shaved legs and arms felt itchy and odd beneath my drab clothes.


Pictured – the surprised look is basically around how damn nice it feels to have good stockings on top of hairless legs. Possibly. Or Cindy has just asked me a question and I’m halfway through answering it when she clicks the camera….

Work ended and I slogged the heavy bag the quarter of a mile to the hotel, not my usual as my usual was fully booked which was an omen I really should have taken note of. Decided to be good, no drinking, and settled down to an early night after trying on all the frocks one by one to see if I still fitted in them.

I woke up at 3:00am with both eyes glued shut, And it suddenly dawned on my that all my planning, the hotel, the frocks, the intended outfits, the sheer fun was off the menu,

Viral Conjunctivitis. Right eye was completely bloodshot and weeping, left eye was following suit. I frantically washed my face but it didn’t get any better, and having had it before I knew that the sessions were completely out of the question – for a start your eyes itch like it’s going out of fashion, but more importantly, and very irritatingly, it’s highly infectious. You can’t put makeup on it because any brushes you use will just pass the fun on to the poor next person who gets it, and the instant you put powder anywhere near an eye with conjunctivitis it swells up.

It’s pretty much the only thing, other than death, that would stop me doing a session completely. All of my looking forward to it was crushed, the effort of getting all the stuff into London, the complete body shave, all for nought.

And it was worse than that because I also was feeling absolutely crap, and facing trying to get home with a massive weight of dresses along with not having the rush of having fifteen odd new looks to ponder on the computer.

To put it simply, it sucked. And it still does, two days after I should have finished. I feel like I’ve been cheated – luckily I rescheduled but not until late April meaning it will be the longest I have gone without Sarah time since I started doing it again.


To add further insult to injury the eyes are starting to get better, little bastards.

So to cheer myself up and stop myself from railing at everything, and believe me it’s hard because I’m grumpy due to feeling like minute-microwaved poop and having been looking forward to some quality Sarah time and getting none, and also because I work very hard in my drab life and the Sarah time is my downtime, it’s my treat for all the early mornings and late nights, all the saving I do. To have that whipped away because of a damn virus is, well, first world problems at their finest.

So, deep breath, I need to cheer myself up. And I’ve done that in the last couple of days by diving into the archives and HUGE number of pictures to find things to put a smile on my face. Oh, and setting my credit card on fire buying a tonne of new outfits that I told myself I couldn’t have because they wouldn’t get delivered in time – delaying the session by eight weeks destroys that thin argument so I’ve got a gorgeous tartan Kitty coming from Vivien of Holloways, two new frocks just released by Joanie Clothing that are just to die for and some other fun bits because sod it, Sarah deserves it.

So I thought I’d pick a couple of looks I have done in the past that I go to when I want to cheer myself up, and explain why they cheer me up. For some it’s something I can’t quite put my finger on but give me a rush of that warm joy that only a crossdresser knows, for others it’s just the WHAM factor of seeing someone I don’t know, who is so diametrically opposed to the shell I carry that it just almost stops my heart to see.

Anyway, time for a cheer-up and a dive into the archive…….

The Church Dress….


I know I have and do go on about this frock a lot but it is one that just ticks so many of my internal boxes when it comes to what femininity is for me. The style, the pattern, the feel, it’s just a sublime dress to wear and one of the few I don’t want to take off at the end of a session.

I don’t think we’ve quite nailed the hair for it just yet so I’ll be doing this outfit again. It’s high on the list of outfits that I want to do another apartment session with – there are some very good apartments in London that you can rent for a couple of days at a time, and they give you a kitchen, a living room, a bedroom, which is a perfect little microcosm for being yourself if yourself is a crossdresser who is terrified of the outside world. In my defence as I am always going on about, I’m 6ft2in before I put a pair of heels on and heels make an outfit for me, so I’m always going to be a pretty head above the crowd. Plus as much as I want to, and believe I want to more than anything, I can’t quite subsume the male persona when I dare to walk the streets of London. It’s a confidence thing, one of those annoying reactions your mind has when it says ‘you can’t’ and you don’t because it says you can’t which makes it a self-fulfilling prophecy. I’d love to be able to go out just once and someone comment ‘she’s a tall woman’.


Pictured – anyone else get a wee little thrill from hugging yourself when you’re wearing female fabrics? Just me? Got to love fetishes.

Anyway, back to the frock. It’s a difficult shape to pull off, high waisted, but I just love the style of the collar and cuffs, and the inner lining is like pure cold silk against your skin and stockings, which warms up as you wear it.

And now the why. This dress gives me a warm little rush because of what it looks like – the kind of dress a wife would wear to church. It’s not a trendy dress, even by retro standards it’s a bit mumsy, but the style seems to kick off the role-playing part of my brain, the bit that loves to say ‘what if’. This is a ‘what if’ Sarah was a married woman who diligently attended church every weekend. It’s the perfect modest attire, and it thrills me because it is pretty much the complete opposite of the disguise I wear on a daily basis. He’s gruff, cynical, atheist, scruffy, always looks like he has been dragged backwards, screaming, through at least two hedges, one of which containing very out of date clothing by the look. She looks like someone who takes care with her appearance, but someone a bit stuck up and full of herself.


Pictured – stuck up, moi? Be careful young man, or I’ll get my husband to glare at you.

I like that. There’s a picture of me wearing this outfit in a group on Flickr called ‘Conservatively Dressed Christian Ladies’ and that’s success if you ever wanted it. Cough.

Tranny-trope time, the uniform years…..


Going back a bit this one, but I still have the uniform in my (small) closet of femm stuff. Before I enthuse about just how much fun it is to wear a dress designed for women to sigh in as they pick up yet another room untidy beyond belief, I need to explain the closet.

The closet is actually half of my wardrobe. I don’t have a lot of bloke wear, and what I do is pretty standardised – I have a drawer full of the same kind of sock (Darn Tough walking socks, green and black stripe because they don’t do a damned black one), a drawer full of underwear (identical M&S black briefs, can’t do boxer shorts because it feels like you’re wearing shorts on under trousers), a drawer full of t-shirts (mostly black, work logo or Nine Inch Nails) and two pairs of black jeans. And that’s pretty much it, other than climbing gear and walking gear which hangs on the left side of my wardrobe.

The right side is, well, more colourful. I don’t keep many of the frocks I wear – they are literally used for one session and then sold on or donated. I like to have new looks, as it may have become apparent over the years, but there are a few dresses that are tucked away on the far right that I won’t get rid of or sell. There are three Kittys in there from Vivien of Holloway, which is astounding given the number I’ve owned and worn (about twenty so far which is outrageous in a wonderful way). There are a couple of Joanie Clothing dresses, one of which I’ll talk about later. And then there is this uniform.


Pictured – yup, went through a ‘housekeeping’ phase. And it was a lot of fun.

Looking back I bought it because it is actually a classic 1940s style dress masquerading as a maid’s uniform. Lose the apron and it’s a femme fatale early 1940s collared dress – in fact the place that sells them has been selling the same style for decades. I actually had one back in the ‘before-time’, around the early nineties, when I used to frock up and clean the house during the ‘naughty and unfocused’ phase of my trans-existence.

It’s still in my closet because I secretly love it as an outfit and a statement. Yeah, it’s one of the classic tranny-tropes, but it’s a proper uniform and it’s a lot of fun to pretend with. Plus, like the Church dress, it gives me that warm feeling when I’m buttoned up in it, it feels, well, just right.


Pictured – what’s not to love? I love the collar, the apron, the hat, the fact it was manufactured for someone to work in, the whole shebang

I think my uniform days are behind me, although I do have a gorgeous retro 1950s Coca-Cola waitress outfit in the wardrobe, and a shocking pink with white polkadot fetish satin ‘sissy maid’ uniform for when I want to exercise my inner sex-objectification. Yeah, the right side of my wardrobe is…….interesting.

And now the why. I love the idea of a woman in uniform, it ticks yet another one of my fetish boxes. I think it comes from the fact that I’ve always hated being told what to wear, so drab me goes out of his way to not conform to what is expected. Sarah on the other hand, for a long while, craved that almost submissive action of dressing in an outfit designed to remove individuality. It’s part of the loss of control that makes up a lot of the fetish in my head, and also it’s subscribing to the sexist notions in my mind. And hence why it isn’t so much of a drive any more, now Sarah appears to be, err, the dominant personality at times in the crowded set of apartments inside my mind.

The 1940s Hostess look….


We did this look a long time ago and it was probably the first look we did, although I loved all of the looks, where I saw the pictures and went ‘wow’, I look like a happy comfortable 1940s housewife about to host a party.

I think it’s the colour that does it. That green is a colour you don’t see in outfits nowadays, it reeks of the wartime years and in itself gives a lovely retro feel to the outfit. I loved the dress so much I bought it twice; the first time, shown here, I went for a size up and whilst it fit it felt a little baggy in places, so I got a size smaller that fit a charm, and bought it in red as well.

All of them are gone now and not in the wardrobe because although I loved that style I didn’t see how I could do any more poses with it that didn’t look samey. It didn’t stop me fantasising, and suggesting to Cindy at one point, that we organise a 1940s ‘husband and wife’ evening where we could pair up retro styled and dressed clientele with appropriately vetted admirers for an evening of 1940s frolics. Sad thing is you can’t get people to do that kind of thing without other implications and if it’s all about the dressing up and role-playing what does the admirer get out of it, unless he is in a committed relationship with the wife already. So that was kinda shelved. Would have been fun though, and I would have thoroughly enjoyed and got into the role-play.


Pictured – the first outfit where I really thought ‘Mrs’ felt right

What’s ironic is that whole idea smacks of 1940s attitudes as well, so maybe I am possessed by the ghost of a 1940s housewife who wants just a little more time to swish in the frocks of her era.


Pictured – the way the dress hung was just delightful, and that’s genuine happiness in her eyes. Damn, might have to go buy it again…

And now the why. This outfit just makes you think and behave in a way that is old-fashioned. The style and cut means that it flows around you as you walk, sit and pose, and it’s hard to not get a good picture with it. I just love the idea of being a 1940s hostess, there’s something delightfully domesticated in a naive way without being sexual that appeals to Sarah.

The 1940s Housewife day-dress….


So, if the gorgeous hostess dress was the choice of outfit for the evening, this lovely little frock would be the one Sarah spent most of her time around the house in.

I’ve always loved this style because it feels like the Kitty’s less-loved sister. It’s a Vivien of Holloway dress but isn’t as promoted as the Kitty. It doesn’t have the padded shoulders of the Kitty (and I had a very interesting and informative conversation on the closed ‘I have a VoH dress and love it’ group on Facebook, which I’m kinda thrilled to be a part of, where I discovered I was one of the few girls who didn’t cut out the shoulder padding as soon as their Kitty arrived. I was a little horrified by that as the shoulder padding is what makes the Kitty so shaped but it turns out the female body doesn’t seem to be very flattered by them) and the fabric feels coarser in a proper housework kind of way, but it’s just glorious to swish around in.


Pictured – I love the ‘she is thinking about whether to do the washing or the cooking next’ look.

I had two at one time, one a pale blue with large flowers print, and this one, a dark pink with lovely little floral print. Both are gone now because, like previous frocks, I felt I’d done them to death, but I’ve always got a nagging urge to buy another as they are great for, err, doing housework in. Hey, some of us like housework. And like to look pretty while doing it. Yet another sentence I never thought I’d type.

Anyway, the fitting on this dress is wonderful. It pinches in at the waist and flares out, thought not as much as a fifties frock, at the hips. It feels a little like a pencil skirt, even if it isn’t, but that’s because I’m used to the Kittys which have pleats and a very generous circle skirtage if you pull them out. This dress feels like it was designed so you could look glamorous while taking out the remains of the meal from the party you hosted last night (see previous outfit).


Pictured – with a different hairstyle this time. The other one is much better for housework though. Again, a sentence a 50 year old man shouldn’t really be typing but what the hey.

I like the collar style on it as well. VoH do a blouse that is very similar, but for some reason I don’t like separates, I like the feel of a single piece of material you get with a proper frock.

And now the why. I love the look, I love the feel. It’s long enough to be modest and not too long to get trapped in the vacuum when you’re bustling around the apartment. It’s one of those rare dresses that I could see myself buttoning on first thing in the morning and taking off just before bed, in that imaginary world where Sarah could be the one earning a living.

The first time I did a look and thought, wow….


I found this dress on Amazon of all places and thought it looked cool. I was trying new looks out, branching away from the retro look to see if would end up being what I thought I’d be, an uncomfortable looking crossdresser dressing way to young for her years. And then we tried it, combined with my all time favourite wig (we call it the Phoebe after the character from friends) and the results were, well, spectacular is kind of an understatement.

Yeah, the dress is an optical illusion, but it just plain worked. It opened my eyes to what, or who, Sarah could be if she wanted to. Granted, I then went back to retro but I knew that if Sarah wanted a night out on the tiles she could do it and I could, gasp, possibly pull it off.


Pictured – damn, I’m in love with her which just makes it all the more confuddled

Since then my need/urge to go out as Sarah has diminished, partly because I love the controlled environment of Boys Will Be Girls, where I can chug beer, sing along to heavy metal and then pose in the most feminine way without a care in the world, but mostly because the urge to *be* Sarah in the real world has faded.


Pictured – yup, an illusion, but hellfire, what an illusion. Plus, nice legs if I may say so myself.

Sarah comes from a place inside where I have absolutely no confidence. She is my confidence, even though the drab exterior I have gives a degree of confidence (it’s a lie, even now when I have to stand up in front of people and lecture on stuff I know like the back of my hand I’m terrified, never gets any easier when your confidence was destroyed as a child). Taking Sarah out into the real world feels like a test I don’t want to make. In a controlled setting I have control over who she is and what she does. In the outside world it’s a lot more complex and terrifying.

The Mother Figure….


Somehow I always end up looking at the shoots I’ve done with this outfit and look and it fills me with a mixture of emotions. It’s the perfect art in terms of what I want to do, a look that is so far from who I am Google Maps couldn’t find a way back, but it has a lot of emotional baggage around it. Yet still I’m intrigued by the look and it really resonates.

So, to put it bluntly, my mother made me the woman I am today, and saying that with a straight face takes a huge amount of effort. She was an alcoholic, a valium addict, a damaged person who, with her husband, my father, both had massive chips on their shoulders about life in general. Both were second children follow a first child who excelled, and both were very quick to blame the world for their own circumstances. Add a first born child with an exceptional intellect (and again, lots of straight face exercise their – my given birth name has three letters and I don’t have a middle name because the doctors were convinced I was brain damaged by a tough birth and suggested I be given a name I could at least try to spell. F*ck you 1969 health service) and nurturing involved physical bullying from my father who didn’t want an intellectual child and mental torture from a mother who was taking out all her inner rage at her ‘better’ siblings on her own and et voila, you have an aware child with a lot of emotional damage.


Pictured – nah, no emotional damage here, just your normal 50 year old wife. I mean, man. 

A lot of crossdressers come from families where the mother was dominant, and often in a passive aggressive way. I know my emotional minefield is down to finding the need to please someone who can’t be pleased.

There are more biological reasons as to why I ended up standing over both sexes, but the internal self-hatred and shame I can pin on my upbringing very easily. Chuck in the fact my mother discovered my predilection (well, a shopping bag tucked deep in the back of my cupboard with lipstick, dresses and shoes to be precise) and was understanding in a ‘bring it up as unstated blackmail whenever she wanted something’ way and you are going to associate that kind of crap badly.

But anyway, enough half-arsed self-therapy, back to the look.

I love this dress so much for a number of wrong reasons. It’s prissy, it’s mumsy, it’s the kind of dress a wife would wear to her husband’s social events, pretty enough to be feminine without being sexual attractive. And it’s for all those reasons that I love it. When Sarah is this person she isn’t even Sarah, she’s a version of my own mother that’s likeable.


Pictured – I like this photo for all the wrong reasons. It’s a hotel and she looks like she is ready to bite that pillow. Cough.

Genetics wise I have inherited a lot of my mother’s features as opposed to my father’s, which is a good thing for the male pattern blandness/baldness and a bad thing for having wrists that could never be described as a rugby players (my wrists are delicate in a way that made school one long ‘poof’ joke). When I put on the short, 80s style wig there’s a lot of my mother looking back at me.

And for some reason that gives me a power I’ve never had. I haven’t talked to her in ten years and I don’t anticipate ever talking to her again, but this look and style allows me to dispel the fear and turn it into something else.

Plus at the end of a session I can wipe her off of my face, put on a Nine Inch Nails t-shirt and go back to being a cynic. She can go back into the cupboard.

I think that covers the why in way too much detail, but on the frock front it’s a wonderfully fun look to wear. I particularly like having the dress fully buttoned up, it sends a message of unavailability to the look that I like a lot.


Pictured – for some reason Social Media isn’t that stoked on a look that says ‘your mother isn’t happy with your life choices’. Go figure.

Yeah, it’s an odd one to end on and there’s hours of therapy in there to discuss, but I like the outfit and the look. It doesn’t go down too well on Social Media because the meaning and thrill behind it is something that is unique and internal to me, but I still like it a lot. Plus I have a whole long-running fantasy story around it involving a corrupt bank manager and some blackmail that makes for some deliciously naughty photos on Flickr and the like.

Anyway, the intention was to cheer myself up and whilst I haven’t completely succeeded I do feel cathartically better, so that’s a start. Now if I can just kick this cough and conjunctivitis in time for late April I can get some glorious new looks done. And maybe a couple of revisits of the Pretty Retro hostess dress as I, sigh, as part of writing this went and bought the emerald hostess dress for the third time.

Stay beautiful and remember that when life gives you lemons throw them back as bloody hard as you can.


Pictured – err, yeah, maybe my uniform period isn’t quite finished just yet.


One thought on “[Fashion] An Archival Cheer-Me-Up

  1. Well firstly sweetie, can I just say that I am soo sorry that you haven’t been able to enjoy any femme time with Cindy through illness. 😞 I can only imagine how gutting and depressing that must have been. I am sorry. I have all my fingers and toes crossed that you are able to get rid of your illness. XXX
    But I am very happy to hear that you have already booked to visit BWBG again. I would possibly have thought that you may have considered an extra day or two, to make up for the missed time? 🤔
    You already know how much of a fan I am of your outfit choices and I am glad that you have managed to find some comfort in going through your images and absolutely thrilled that you have chosen to share some of them with us. 😊
    You do know that in an ideal world you could come and be my housekeeper any time?! 😊😉 XXX I have a spare bedroom on the top floor of my house and it would make the most perfectly darling servant’s quarters! 😉😁XX
    I really hope that you are able to get back to Cindy, and to submerge yourself again in the fabulous delights of frothy femininity! 😍❤️❤️
    Take care my lovely friend. 🙂 😘


    PS You have skinny wrists too?! 😮 😉 XX

    Liked by 1 person

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