Yeah, I understand the irony of writing a blog about how craptacular January is in February, but to be honest that kind of gives a good impression as to how bloody awful January can be.
I never used to get the blues (pinks/florals) in January, but lately, as I’ve got, well, older, January always sucks. The days are dark, the sun barely shows its face, and all the biological rhythms are way down. I countered it by doing some more stupid levels of damaging exercise; I did 26.1 miles of running for Prostate Cancer Research, meant to be over the month of January but nailed it early on. And in the middle of that little bit of insanity I popped off into London for a cheer-me-up session with Cindy; I wrote up the first part, which was a toned-down look with a couple of outfits. I went back the next day for a good old fashioned retro glam look and that, dear reader, is the subject of this post.
January was difficult. I don’t know whether messing about with female hormones was a contributory factor, but I was all over the place mentally. Some days I had the fogginess I’ve recognised as my brain doing a little rewrite, some days I couldn’t face getting out of bed. But interestingly, as the month dragged on towards February, I started to feel more up and now, a couple of days into the new month, I feel like Spring is on the way.
But back to the session. It was bitterly cold in London so that curtailed going out and about; being terrified and click-clacking over the cobbles of Bermondsey in a pair of fashionable heels and a flowing frock is a rush, but chuck in a -5C windchill around the tucked bits (a skirt does not keep the wind out) and ice on the cobbles and it’s not a lot of fun.
I had a number of outfits for the session but ended up falling back on a number of the brilliant Cindy ‘dealer’s choices’; she still amazes me with her ability to take what literally looks like a belt (she is convinced I will fit into a size 10 dress) and create something dazzlingly different. And she didn’t disappoint this time, not that I thought she would.
So let’s go through the looks one by one and have some February fun; sod off January, see you in eleven months.
Outfit 1 – Bun in the Oven *again*
Before you ask; I have no idea why this look, and just the idea of it, is so damn appealing. It’s an unusual one; a lot of cross-dressers see it as a taboo to try, but I love messing about with it. It’s the implication of the pictures – this woman has had unprotected sex to completion. Plus it’s a little odd thrill to have that bump; I got it from Amazon (and believe me, that really plays hell with the suggested items you get in your feed – note to self, don’t leave an Amazon page up on your work machine showing ‘you might be interested in this breast-feeding dress’) and it’s correctly weighted, meaning it’s a heavy little baby bump.
Only amusing gotcha was this was the first look of the day and I never wear my girdle with it (I now use a girdle rather than a corset, the weight loss has brought my waistline down to a point where a girdle gives me a nice hourglass figure without the organ crushing ‘fun’ of a tight corset), meaning the silicon is directly against my skin. Over time the bump heats up to body temperature and feels like part of you. The downside with this is that no-one else really uses it (I leave it at Cindy’s if anyone wants the ‘mum-to-be’ experience) and Cindy stores it outside. In the -2C temperature.
So, imagine strapping a heavy, silicon pregnancy bump to bare flesh when the silicon is barely above room temperature. Let’s just say that tucking the dangly bits was incredibly easy as the cold in my midsection made everything shrink; add that to the effect of hormones for two months and et voila, no discernible bulge at all. It took about ten minute before my body heated the bump to around my temperature though and that was…..cold.
The dress was from New Look; they do a wonderful range of modern and oddly old fashioned maternity wear. I modelled an adorable powder blue smock a while back that looked like it had come out of a wardrobe directly from the 1970’s. This one was a touch more modern, full length with lovely cuffs and collar.
A nice look to start with, plus it was good to get the weight off my stomach and on to the rest of the looks. Always mildly ironic to lose so much weight and the first thing I want to try in a session is to look bloated with child.
Outfit 2 – a little Collectif Pride
Now this was a cute dress. I really like Collectif’s stuff but I get the feeling occasionally that they really target the T community; a lot of their stuff is delightfully kinky in a gender-blurring way and I’m often, jokingly, asking Cindy who Collectif are targeting with some of these looks.
This dress was a glorious rainbow tartan figure hugging ‘hobble’ dress. I like wearing this for photoshoots but wow, wearing something like this on a normal (cough) day doing normal things would be an enlightening experience. You can barely walk in it, it hugs the upper thighs in a way that makes every step dainty, which I guess is the point of a hobble dress, but I really can’t imagine, say, running for a bus wearing it, especially with a pair of heels on.
Outfit 3 – ‘Housekeeping!’
I have always loved this uniform. I have, cough, actually bought it four times; I had one very early on in my dressing career and it went the way of all of my stuff in one of those insanely stupid purges (I am *so* happy I have gone beyond that now). I then had a size 20 when I was a chubbier girl, then an 18 and now, as of three days ago, a size 14 (which fits delightfully well). This was the ‘retirement party’ for the size 18; it’s too large but the effect of the apron and the tie belt at the back, which pulls the waist in nicely, works well.
I love the style; if you take off the collar and the apron it’s a classic 1940’s silhouette and can work as a retro dress, but I love the idea of a uniform. It ticks one of my many, many fetishes; wearing a uniform designed and produced specifically for a woman, especially a woman in the service industry.
So, cue a lot of ‘housekeeping at work’ pictures to sate my urges and I’m a happy woman. Yes, I know it would be a terrible job but you know what? I like cleaning. It’s satisfying. And to do it while wearing that uniform? Two birds with one stone, sweeties.
Outfit 4 – 1940’s day dress style from Pretty Retro
Pretty Retro have some wonderful styles; they only do a couple of different looks but the ones they do are just perfect; my possibly favourite dress of all time (the green Hostess dress that, cough, I have bought three times in reducing sizes) is from them, and this is one of their newer looks.
We went for a modern hairstyle with it as I love that hair; it’s the ‘Phoebe’ look I’ve used a lot, and it works a treat in my opinion. I love the sleeves on this dress; they are open and flared and feel delightful against the top of your arm.
Not a keeper as I have a lot of similar 1940’s looks, but definitely adorable.
Outfit 5 – revisit and retire
So, what I mean by retire is that I will wear a dress two or three times for photoshoots, and then retire it (which means it gets sold on or given to Cindy for others to enjoy). The reason I do this is there are thousands of dresses I want to wear and, even though it may appear that I do this a lot, in the grand scheme of life and time I spend a very small proportion of my time in dresses.
So there’s always going to be the next dress, the next style I want to model. I went through a period of keeping all the dresses that I loved but that meant I ended up with a full wardrobe of guilt-trips. And my brain works in that odd way of ‘you love that dress, why aren’t you taking it to the session’.
So now I wear them a maximum of three times and then ‘retire’ them; this dress is adorable but I’ve worn it a lot to sessions, so it was time to fling it on once more and then make room in the wardrobe. I love the pattern of this dress; it’s wonderful cute and again I tend to ask myself who Collectif is aiming this at (the 52 year old transvestite market is not a huge one, I think). But still, lovely to wear.
Outfit 6 – another retro and retire one
This dress was an impulse purchase from ‘The Hippy Shake’ based on the fact it was gloriously early 1970’s. I distinctly remember babysitters wearing exactly this kind of outfit (even back then, when I was between 3 and 6 years old, I had an eye for frocks. Go figure).
And wearing it was delightfully retro. It is a roughish fabric and the collar is heavy; you are aware that you have a massive amount of material there. The combination of a very short hemline and the heavy collar and cuffs is an odd but lovely sensation, and we combined it with a proper black beehive hairstyle for that authentic 1969 look.
That was a fun frock but it has limited appeal (i.e. me when I’m wanting to look like my mother in the early 1970’s), and I couldn’t see myself ever wearing it outside.
Outfit 7 – On to the Dealer’s choice and, gasp, back into trousers!
Cindy has a wonderful eye for current styles. As a retro girl my tastes are seriously in the ‘women wear dresses’ category, so when she suggested a jumpsuit I was in two minds.
Part of me was ‘oooo, yes!’; I love the sensuality of a tight jumpsuit combined with heels. It is paradoxically very feminine. But the other part is based on, and I dare to say it in case I give the giggles, the concept of cheese-wire.
See, I’m tall. No getting around it, I’m a Sarah Plain and Tall, topping off at a couple of inches over six feet before putting heels on. And that’s not such a big problem with dresses, other than everything other than a maxi dress looks like a mini-dress on me (and given men like legs that’s not such a bad thing, says the hormones).
So when I’ve tried jumpsuits and pantsuits in the past I’ve hit the cheesewire problem. See, female torsos aren’t, well, as long as mine. So when it comes to squeezing into the tight trousers and tight top of a jumpsuit I always tend to end up with a lot of material trying very hard to get up inside me; when I put my arms into the top and zip it up the crotch area, which is not designed for anything to be there, always seems to want to be six inches higher up than it physical can be.
It is literally like wearing cheesewire. Which is why I’ve avoided pantsuits and jumpsuits.
But Cindy was convinced this one would fit. And yes, it was a size 12, which is optimistic at best. But she was right, it fit like a glove. A very tight, restrictive, put everything down there to sleep as it’s cutting off the blood supply glove, but still, it fit.
And it was incredibly flattering. Sitting down was an experience; let’s just say even if the hormones haven’t rendered me permanently infertile (and that’s one of the first things they do) then 30 minutes wearing a jumpsuit definitely finished me off. Call it a cheap way to do a castration. But you know what? Totally worth it.
I felt a million dollars in it; the combination of a sleeveless white lace top and the black pant legs was gorgeous. All I needed was a glass of champagne and a well dressed banker hunk on my arm and I reckon I could have slipped into any number of parties down at Canary Wharf, assuming the bankers still play there. Again, another dealer’s choice that wouldn’t be something I would have chosen but wow.
Outfit 8 – Classic Frou-Frou Pink Cake Bridesmaid Dress!!!!
Oh my lord. Yeah, we cross-dressers do have a number of what I like to call tropes; those looks that are stereotypically and classically ‘girly’, and this one, wow, dead on. I’ve always secretly loved those terrible bridesmaid dresses; the ones where you know the bride had chosen them particularly to make the bridesmaids look almost ridiculously silly. And this was delightful.
Again, a dealer’s choice; Cindy had picked this up for her rotation of outfits because she knows exactly what appeals to some of us and it had just arrived. Yes, it was too small but that was part of the fun; throw in some gorgeous over the top hairstyling and a glass of champagne and you know this bridemaid is one of those that will be caught around the back of the church, frills and froufrou up around her waist as the best man drunkenly tries to have his way with her.
Yeah, it’s one of those teenage fantasies that a lot of us have shared, the larger proportion wanting to be the best man whereas the rest of us, well, I’ll leave it at that for the sake of not having to censor my own blog. But still, these pictures make me laugh, smile and have delightfully dark and odd thoughts about being around the back of the church.
Outfit 9 – dealer’s choice, more cheesewire….
Another new outfit Cindy was dying to try out on a willing victim/client. This one consisted of a lovely white lace top combined with a set of leather leggings that, being honest, were trying very hard to be subcutaneous. They were ridiculously, and wonderfully, tight.
Amusingly I had to relax my legs a lot for this part of the shoot. Having done a daft amount of exercise in 2021 (1430 miles of cycling, running and walking according to Strava, which amazed me as well) I literally have to tense a toe and bang, the whole leg looks like a piece of tight beef. So, to take advantage of this outfit, I had to be careful not to tense the muscles.
It worked a treat. Again, I’ve spent my life trying very hard to get out of trousers and lo and behold, dealer’s choice number three and I’m back in leggings. But it was a lot of fun, even the tug of war trying to get the damn things off….
Outfit 9 – the High Class Escort
Escort is such a nice word. Sure, prostitute is more accurate, but still, it keeps a gloss of acceptability to call her an escort. Anyway, I get ahead of myself; this was another dealer’s choice and the first time I’ve worn the breastplate in a long while. With the advent of hormones, the addition of tape and a lot of ‘please don’t touch the nipples if you can, the hormones have made them insanely sensitive as they work in turning them into lactating boobs’ we normally create a cleavage from, gasp, my own cleavage, but we wanted, with this outfit, to have some proper ‘assets’ on view.
Again, this was a dealer’s choice; Cindy combined the low cut black lace top with an asymmetric skirt which was delightfully confusing. A part of my mind is pretty screwed up (you don’t say) and I like symmetry, and this skirt was a real ‘what the?’ moment.
It was a tease. It was just long enough, on one side, to pass as a skirt, but the bit in the middle made sitting down without revealing my panties almost impossible. But when you’re an Escort the paying customer needs to see the merchandise, I guess.
Anyway, it’s nice to tart up occasionally. Being serious for a mo, my taste in dresses and looks is really the retro side and I don’t do this kind of look often; interestingly something I think is delightful and sexy will get, say, fifty or sixty likes on Instagram. This look gets two hundred plus. Cindy knows her stuff.
Managed to open up two possible future careers during this session – housekeeping and prostitute. I’ll keep those in mind in case my career ever hits the skids…..
Outfit 10 – the Posh Bird
Ooo, this was different and oddly satisfying. A lot of the stuff I buy is from Amazon; I go to the boutiques, such as Vivien of Holloway, when I want something a little more classy in the retro side, but other than my gorgeous ‘date dress’ from Bombshell HQ, that I went out of my way to spend a lot of money on because, erm, I had a date with someone I wanted to look attractive for (and there’s a whole session with a shrink in that sentence), I don’t tend to spend a lot on the ‘posh’ dresses.
This was a Cindy ‘dealer’s choice’ and it was a Karen Millen dress. Going to be honest here, and show my male roots, what’s left of them, and say I’d never heard of her, but looking up her website I found some gorgeous and bank-account gouging frocks (I kinda wished I hadn’t because I know when I get drunk sometime soon I’m going to wake up having spent a month’s mortgage payment on two or three cocktail dresses). And this was a Karen Millen frock.
It felt, well, expensive. The material was comfortingly heavy and delightful to wear and, being honest, it was a real effort to take it off and return to drab me for the drive home, but yet again Cindy had nailed a look.
Of all the looks of the day I found this one the most interesting because when I looked at the pictures, for the briefest of instants, I could see the woman I would have been if the temperature had been a couple of degrees hotter when my parents did the horizontal folk dance (and, more bitterly, if the doctor’s hadn’t decided to excise the female bits and slap me on testosterone when I came out with a multiple choice of biological sex). It was a poignant moment and a delightfully odd one; the combination of the posh frock, the smile, the obvious comfortableness of the pictures. It felt unusually normal.
And that was that, ten outfits, ten hours of fun, followed by a swift curry via Uber Eats and three hours of intense driving; leaving Cinders is always interesting because I drive through the centre of London at 22:00 on a Saturday night, often blinking as the makeup remover always makes my eyes blur. Completely worth it; the plethora of Dealer’s Choices made it a wonderfully interesting and different session.
Anyway, stay beautiful; I’m not having another Sarah session until April as I’ve decided to focus on fixing the broken bits (bits I broke) of my body and making sure I’m mentally refreshed before I don the frocks again. Don’t read anything into that around Sarah going away, it’s just I’ve been intense for five years and Sarah needs to be relaxed. The blog posts will still come, infrequently as per normal though, so stay tuned for more silliness.