Ooo, strap yourselves in, this is going to be a long one. No philosophy, no meandering around the ‘meh’ of daily life as drab, just a long, hard (oo, err) look at *every* outfit I just did with the delectable Cindy during the three day mega-session we just finished.
I always say to myself that I’ll do this for every session but I get distracted, normally by casually browsing the pictures from the session (yeah, one-handed, sue me) or frantically planning the next session before my drab life absorbs all the fun out of everything.
So, dammit, I’m going to explain the thinking and, yes, titillation behind each of the looks. And I need to be quick as the postie just delivered a parcel from Amazon with the complete short stories of Kurt Vonnegut which means my weekend will be spent in bed, copious amounts of coffee and, sigh, reading glasses.
I’ve already described on a daily basis what we did but those posts were written in the heady and exhausted afterglow, the smell of makeup remover still in my nostrils, the mark across my forehead where the wig-cap was making it look like I’d just had brain surgery, so there was a lot of fog then. Now, a couple of days after the fact and post having some delicious fun with the photos (I post a lot of the Vivien of Holloway frock pictures to a closed group on Facebook filled with GGs gushing about their dresses and get a lot of sweet and flattering comments…. it’s like they don’ realise I’m a 48 year old grumpy man but instead think I’m a mature retro frock loving woman) it’s time to expose (again, oo, err) all of the looks we did with my reasoning behind them.
So, grab yourself a coffee darling, and settle in for some gushing fashionista fun…..
DAY ONE – The ‘Normal’ look
Well, ‘normal’ in an odd sense of the word. Less fabulous? Less glamorous? More, dare I say it, whispering, passable?
Outfit 1 – trendy separates
I don’t normally do skirts as I love the feel of a dress when you do it up, but this skirt…wow. Nice and heavy, pleated, went down a storm online. The top was partially see through, the heels sensible and makeup subtle. Also, not red nails!!! A complete change of look.
In my usual drab sexist manner, would I do her? Of course 😉 She looks like someone I’d love to have a coffee with, intrigued as to what she does for a living.
Outfit 2 – not dressing age appropriately
As per usual my timing was exquisite – Cindy had just had this dress delivered. A frilly top combined with a ‘just too short’ leatherette skirt, it was delicious and delightful to model. Absolutely not age appropriate – if Sarah went out like this she’d come off as some kind of man-hungry cougar. Chuck in a delicate choker and a hint of attitude and brrrr.
Would I do her? See previous comment. Man-hungry cougar And look at the skirt!
Outfit 3 – 1970s Satin Flouncy Maxi Dress
I had second thoughts about this dress when I bought it. It was seriously retro in a 1970s way, buttons up the front, and a kinda ‘what my mother/grandmother would have worn to a summer party’ look. So we tried it with my natural hair colour, silver strappy sandals and, gasp, no tights or stockings. Amusingly this was the first day it was cold and walking from the makeup room to the studio where Cindy does her magic the wind blew up my dress and, well, wow. The feel of a silk maxi-dress rubbing over bare hairless legs while an icy wind blew through is something you need to feel at least once in your life.
A bit mumsy but that was the point.
So that was the normal look, a selection of interesting fashion choices. I like normal Sarah. But I *adore* glamour Sarah…..
DAY TWO – Glam, Glam, Glam!
Day two was the first of the long days – a ten hour session where, bless, Cindy was feeling a little fatigued but still utterly at the top of her game. Interestingly I take a while to warm into Sarah (again, oo, err), partly because the makeup is meticulous and takes a little while to complete, during which we tend to talk about, well, not such femm-y things – this time we talked about quantum possibilities, the pros and cons of an iPad Pro versus a Macbook Pro (basically comes down to if you want a Macbook Pro with a lot of storage then the best option for being able to afford it is to become an escort, because that’s the only way you’ll get that much money 🙂 ) and my interestingly flawed attempt to not drink for a while (that lasted all of ten days, fell off the wagon yesterday and it was goooood). So I always bring a couple of ‘gentle’ frocks as warmup, something I’m not completely in love with but allows me to start to feel the Sarah vibe, the loosening of the muscles and posture, the relaxing of the wrist , the, gasp, smiling.
But today the warmup outfit worked an utter treat.
Outfit 1 – cute little demure blue retro frock
God, I *loved* this frock. It’s a beautiful material, soft, wonderfully fitted and just long enough to hang over the knees. I bought it because of the colour and the pretty neckline, but once we put it on and picked my favourite hair, the ‘Phoebe’ look that remind me a lot of Lisa Kudrow from Friends, the entire outfit just clicked and bang, Sarah was in the room. It was actually the kind of outfit that I would have been more than happy to slip back on and simply spend the day in, delightfully normal but very sensual and sexy.
If I wasn’t her and I wasn’t married, she’d be the woman I’d be stalking. And she’d have no time for me because she could do way better…….
Outfit 2 – Bella, Lindy Bop pink strappy swing frock
A super-girlie look this – strappy pink swing dress with pretty buttons at the front, petticoat, slightly trashy white heels, flower in her hair and pearl jewellery. Lovely to flounce around in, plus I adored the way the shoulders and bodice accentuated her bosom.
I can imagine her going to a 50s dance class like this. And complaining about how her feet hurt eight minutes into the session.
Outfit 3 – every 1980s woman I fantasised about rolled into me
On my Goddess. Patent heels, nude stockings, keyhole PVC very tight wiggle frock with a high tight collar, Joan Jet hair. And the best thing? Deliciously kinky to wear, feels like you’re sliding into a warm glove that holds every inch of your body.
Definitely one of the reasons it’s taken a while to write this blog as I have to keep ‘taking a moment’ after staring at the picture for too long. Damn, she’s hot. Damn, I’m hot 🙂
Outfit 4 – Virgin Stewardess
I travel into London from Birmingham International train station and regardless of what time I get there, be it 5:30am on 5:30pm, I always end up riding the escalator behind a stewardess. And they are always dressed utterly beautifully, mid-length pencil skirts, tidy uniform blouse and jacket, jaunty scarf, uniform cap. I always get the urge to complement them but they get it all day, every day. I did a Pan Am uniform a while back and at the same time I bought a red uniform which had sat in my wardrobe for at least a year. When packing for this session I chucked it in and et voila, Sarah the Stewardess.
I don’t know what it is about a woman in uniform but it works for me. I just wish I could find somewhere to buy proper uniforms in a UK size 18…. 😉
Outfit 5 – The Bridesmaid
Well, this was a more than pleasant surprise….. I wanted a ‘bad’ bridesmaid frock, I love the idea of the bride forcing her friends to wear the worst dresses, all pink frilled cakes and unfeasible shapes, so I bought this frock, tried it on at home and it didn’t fit, so into the wardrobe it went in the vain thought I might shed some weight.
Fast forward a year and some of the weight had come off, but it didn’t do anything for me when I looked at it hanging there. When I was packing the huge backpack for the sessions I stared at it and thought ‘might as well chuck it in, it’s only feeding the moths there’, and in it went.
But when we tried it on, *wow*. The peplum bit makes it look seriously sexy and 80s, the fascinator adds a touch of style and, with the silver heels, clutch bag and a glass of red wine, Sarah looks like a stunning wedding guest. Both myself and Cindy *loved* the look and it just worked. It’s a lovely mix of stylish and tarty.
And yeah, I’d do her. Quietly outside the tent while the best man made bad jokes.
Outfit 6 – Schoolgirl Sarah
Yes, it’s a tranny cliche, but it’s a lot of fun to frock up as a schoolgirl. I tend to avoid the party style outfits and look for something a little more girlie – in this case a lime green gingham swing dress from Lindy Bop (they don’t do it anymore, which is a shame but you can see why 🙂 ) with a seriously pretty Peter Pan colour and buttons. Chuck in white stay-ups and sensible Mary Jane shoes and you’ve got a lovely little summer school look.
Yeah, I do get the occasional odd email from an admirer about this kind of look – it’s really a BDSM type of thing, ultimate emasculation and all that. But I wear this style because it’s cute and it gives me that warm feeling inside. Maybe sucking my thumb was a little too much but, you’re only young whenever you chuck on your little girl frock.
Outfit 7 – Mother of the Bride
Another impulse buy that spent too long in my wardrobe, this was a lace dress with an adorable collar and a silk underskirt that really came alive once you got it on. I’d literally forgotten about it but, again, threw it into the backpack as a backup frock. But once we got it on, especially combined with those darling shoes and some sensible hair, it looked divine. Very Felicity Kendal-esque and another look that I find seriously attractive. Dammit.
The flower is a nice little touch, and the whole ensemble felt like the Mother of the Bride. Also, utterly comfy to spend time in, the underskirt was like wearing an expensive nightie under the lace.
Outfit 8 – Tarty 1980s Barmaid
“What’ll you have, love?”. This dress was just made for a tarty 1980s barmaid to totter around in. We’d never tried this hair before, partly because most people are smaller than me and it looks too drag-queeny, but on me it was lovely. I bought the dress because of the ruffled collar and the asymmetrical skirt and it was so much fun to walk around in as it was somewhat of a hobbler.
Pint of guinness, bag of scratchings and you, darling…..
Outfit 9 – The Halloween Witch
I fell in love with this outfit when I found it on a website a couple of years ago. The collar, buttons, puff sleeves, insane shortness just ticked all my boxes, both Sarah’s and drab-guy’s, but they only did it in a size 14.
Fast forward a couple of years, giving up red meat and cutting back (cough) on the copious alcohol and I can just about squeeze into a size 16 if I don’t want to breathe or move. But I was so in love with this frock that I bought one anyway under the delusion it would fit.
Well, it fit. And, going to be honest, probably may favourite sexy look I’ve ever done. So cute. Because of the length we had to man handle two pairs of glossy tights and some tight binding knickers on so if I bent over or went even a tiny bit from vertical I wouldn’t be flashing my nether-regions, but it was so worth it.
And that was day two 🙂
DAY THREE – modern retro modern glam retro
To be honest my brain wasn’t firing on all cylinders when I showed up for day three, still utterly eager for some serious fun femm time but when Cindy asked what kind of look we wanted for the day I literally said – “You know. I love the retro stuff and I love the modern, so why don’t we do some retro look with some bits from the modern. Modern look with a retro twist, including the retro bits. And the modern bits.”. Not my most helpful moment.
So Cindy tried something new and a lot of fun – GLITTER! She added some glitter to the lovely blue eyeshadow I had on, then widened my lips (insert sexist comment here) and added a touch of gloss to make them even more like a ladies under-parts (see previous blog post on why red lipstick equates to the V word for amusing titillation). And off we went again….
Outfit 1 – another warmup frock that turned into one of my faves, retro Pheobe
I didn’t expect this frock to work. It’s a long shape that tapers in and then fishtails out at the bottom, but I loved the pattern and the pretty collar, so it was the day three warmup. But I was soo wrong. Again, we used the Pheobe style hair which I am in love with, nice high patent heels, nude stockings, some pretty jewellery and there she was, the Sarah I want to be again.
The dress was a lovely fabric as well, slightly crenelated so it held close to the body and with the corset done completely tight (34in waist) the dress flowed over it in a beautifully feminine way. Quick dab of a lovely perfume a friend gave me as a present (thanks, Sis!) and I actually started to feel a little teary and emotional, which I hid during the shoot. This was the person who lives inside most of the time and she was out in the real world for a short time. Delightful feeling, and the frock went from a warmup to one of my all time favourite looks.
Outfit 2 – 1980s Nightclub Tart
And it just got better. I bought this bodycon dress because I loved the pattern which seriously accentuates the feminine shape. We combined it with some cream heels, chunky jewellery and the 1980s fluffy hair from day two and wow. I couldn’t have felt more feminine – staring at Sarah in the mirror just brought back all those nights in 1980s nightclubs seeing the beautiful women dance.
The glitter on the eyes and the gloss on the lips really brought out the party girl look and I kinda fell in love with her.
Hell, one more picture for the horny post-pubescent that lives inside my skull alongside Sarah.
Outfit 3 – Posh City of London Bank Secretary
A have a soft spot (again, oo, err, etc) for the well dressed women I see in the City of London, heading towards their jobs where they have to do the biddings of bankers and look stunning while they do. So I bought a tight, high-waisted black pencil skirt and a lovely pink pussy-bow blouse that had gold buttons on the cuff and a very loose fit to it. The idea behind the look was the subtle sophistication combined with the office look, and I think we nailed it. Plus the glasses helped a lot, always makes it somewhat sexier as opposed to highlighting short-sightedness.
Outfit 4 – Vivien of Holloway Lilac/Floral 1940s Tea Dress
Almost lost for words now. This dress is the epitome of femininity to me, and to see Sarah, no, me looking so happy in it is an eye-opener. I love the way it makes my waist look small, the colour, the buttons and collar, the padded shoulders. It was utterly delightful to wear and I had that wonderfully strange moment after we’d done up the belt and I’d walked carefully into the cabin for the photoshoot on my four inch white heels, where it suddenly felt like *me*. That dress was designed and created for a woman and here I was wearing it, and it fit like a glove. It pulled in around my waist, neatly around my bosom, hung down to just above the knee. I literally couldn’t keep the smile off my face and to see her in the mirror, so happy just from wearing a beautiful dress, was a divine experience.
I didn’t want to take it off.
Outfit 5 – JoJo Blouse, Circle Skirt, the 1950s young woman look
Again, I don’t normally do separates but I love the blouses and skirts from Vivien of Holloway. They feel ‘quality’, if that makes any sense. The JoJo blouse is a 1940s style, very wide colour, padded shoulders. I bought one in pink with a floral print, and combined it with a full black and white polkadot circle skirt with a petticoat underneath. Topped off the outfit with the polka-dot Mary Janes from Lindy Bop and it felt like I’d tottered back in time.
This is why I love the retro stuff. The clothes ooze femininity, and the feeling of a petticoat swirling around under the huge skirt is something else.
So, more gushing……
Outfit 6 – the only re-visit of the session, the Hellbunny Halloween dress with pigtails
I got this black velvet cute dress for the previous session, but fancied seeing what it looked like with the lip-gloss, glitter and some seriously cute bow-heels from Cindy. And yup, worked a treat. Very sexy in all the right ways.
Outfit 7 – my *third* Vivien of Holloway Kitty dress
Drab me has two pairs of jeans which I alternate between, one wearing, one in the wash. Sarah has three separate Kitty frocks and has just ordered a fourth. I loved this one a lot, the vibrant colours makes it a very nice party dress, and combined with pink open-toed slingbacks it made a lovely outfit. The fabric on the Kitty is indescribably lovely on the skin and this was another outfit that I found hard to take off.
Outfit 8 – the nursing mother
Ok, so this was a little different (you can pick your jaw off the floor now 🙂 ). A while back I sourced a ‘training baby’ from a medical supply provider – it’s a correctly weighted child doll designed for impending mothers to learn how to hold their children. Combining that with the super-realistic breasts that Cindy has got (and I’ve bought a pair, the maker is in Russian and they are bloody good) we created the scene of a mother feeding her child.
Not to everyone’s tastes but I love the idea of exploring roles that I’ll never be able to do. Plus the picture is kinda hot. All it needs is a prude telling her she shouldn’t be doing it in public and zing, complete realism…..
Outfit 9 – 1970s car-key party Swinger
By this time, after twenty hours of outfits and photos, we were starting to go a little mad so it was time for fun. This is Sarah if she was a promiscuous woman from the 1970s attending a car-key party,
For those who have never heard of it, and it may be a very 1970s British thing, but couples would show up to someone’s house, the men would put their car-keys in a bowl and the women would pick out sets of keys…..and then engage with the owner in sexual activity. The original swingers parties for the middle class.
So, whoever has the Audi? You’re taking Sarah upstairs for some fun.
Outfit 10 and the last – Messing Up Kitty’s Makeup
So, this one needs a little explanation. It’s the end of the session, I’m going to have to wipe off all of Cindy’y magnificent work and return the land of the drab but, to make it more fun, we decided to pick on Kitty.
Kitty is the naughty side of Sarah. In the past we’ve done shoots with Kitty as a prostitute, a porn star, an escort who has fallen on hard times and is dressing as a cat for punters and the like. We tend to be cruel to Kitty as it’s the end of the day.
So this time the idea was to dress Kitty up as a high-class escort, take some before pictures, and then go to town on the makeup as if she’d had a rough session with a paying customer. Yeah, sick mind and all that, but I’m allowed to – it’s me 🙂
And amusingly those are seven inch heels. I was literally scraping the roof….
Yeah, that was fun. Bad Kitty…. I sometimes feel sorry for her. A bit. Not much. But a bit.
So there you have it, twenty two hours of modelling, 2300 pictures, 22 outfits, one happy Sarah, one slightly sad drab-guy.
Within three days of getting home I’d booked the next one. That made me less sad.
Thanks for making it to the end, you beautiful reader. I hope you got some of the enjoyment I did out of it.
Here’s one last picture from the shoot. Sarah as I love to be her, in some natural light just enjoying the moment.
4 thoughts on “[Fashion] WAR and PIECES of fashion”
I think this may be my favourite of your writing yet! XX
I love the descriptions you give for your choices of outfit and how well you wear them! 🙂
I think you definitely have your eye in more than you realise for Sarah’s body shape. XX
I love how wonderfully well you inhabit each outfit hun! XX
I am absolutely struggling to decide on a favourite. 🤔
But taking everything into account I think that swinger Sarah might just pip the others to the post! 😁 Whoever owns that Audi is a VERY lucky guy! If only those keys belonged to a Hyundai. (sigh.) 😉
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My god, this is fantastic. You look amazing. I’ve only just discovered BWBG and the fantastic work Cindy does for everybody – but in your case the results are exceptional.
I have to ask: How much does a three-day spree like this cost? (If you’re willing to answer…)
And also: Can you provide a link to the breast forms that you bought?
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Thanks for the complement 🙂 Have a peek at the BWBG site for prices at http://www.boyswillbegirls.com/makeover/ , and the breast forms were from the amazing http://www.boobsshop.com
What a fantastic write up and illustration…. just love your outfits and your style.. I was trying to choose a favourite, but I can’t, they’re all wonderful, from the trendy separates in the beginning through to messed up kitty at the end… fabulous darling 💋💋💋