transretrogurl

Fifty years. Hellfire, when I was growing up people over the age of forty were ancient. Now I’m literally on the verge of staring back down half a century you realise how misguided youth can be. On the plus side, I reached fifty (much to my surprise having convinced myself I was going to die at the age of 31, which made the year 2000 even more of a surprise).

Birthdays aside (sob), the next time Sarah comes out to play she will be, cough, in her fifties. Not looking forward to hearing her complain about it, basically because she’ll berate him for letting the bod go (he hasn’t really, in fact he has climbed mountains, ran two 5Ks, and tries to avoid all the food that she detests when he eats it).

And as I’ve been remiss in doing a blog post lately (work has been intense, plus for some reason everyone seems to be suffering from a cold that won’t go away, me included), I thought I’d let Sarah take the reins and let her have a gush.

So, in honour of our birthday, I’m letting Sarah pick her all time favourite ten looks, and explain why.

Just a quick caveat – these are her favourite ten looks *tonight*. Her mind changes a lot and there are a ridiculously large amount of looks to choose from – one day she feels very housewifey, the next she delights in PVC, the next maid uniforms, you get the gist. But tonight, on the verge of the big 50, these are the looks that make her eyes mist up….

10: You want fries with that, hun?

This look is going back a bit now, both for me and for the style – I have a thing about 1950s American Diner uniforms. They are so, well, ugly in a beautiful way. They are utilitarian *but* undeniably feminine, and this one wasn’t even a real diner uniform but an odd choice of style from Lindy Bop.

It was listed as a rockabilly dress but the moment I saw it I thought wow, that would look so cool in a 1950 waitress ensemble, and et voila, with the magic of Cindy at BWBG and the judicious use of a gorgeous drag style wig suddenly I was chewing gum, taking orders and trying to keep fat truckers from sticking their greasy hands up amongst my petticoats.

Wonderful roleplay outfit, especially chucking in a pencil and pad, and the glasses.

Why I love it – because she is a working woman. You can imagine her finishing the late shift, changing the heels the manager makes her wear for a pair of flats, putting on a drab raincoat and walking home to her apartment. It’s wonderfully 1950s.

9: 1950s Housewife silliness

I’ve gushed about this look a lot before and whenever I’m perusing the insane amount of looks I’ve done I come back to this one a lot. Mostly because the dress is just gorgeous to wear, pulls in in all the right places, flares out where it should. But mostly it’s the circumstances around those pictures.

I wanted to do something different so I rented an apartment in central London, a place I use for work a lot because, for the price of a four star room, you get a bedroom, bathroom, kitchen, living room. Effectively a mini-home. And I had a crazy idea I’d like to experience an evening or two fully enfemme without the having to remove the makeup at the end of night and walk back to a hotel.

So we did a session (actually we did a couple) where Cindy graciously came to the apartment, did my makeup and hair, took some pictures, and then left me there to my own devices.

It was glorious. There’s nothing more liberating for a girl like me than to be able to walk around an apartment, completely safe and with carte blanche to behave entirely feminine. I peed sitting down! I watched a terrible rom-com movie, even had a little cry when the girl got her unfeasibly handsome man. Sat and read Cosmo, including an article or two about sex tips for women that were, err, very eye-opening.

I stood at the balcony and watched London in the evening, feet away from people as I stood fully frocked up in 1950s attire and trembling on my heels. I opened the door to the apartment and stepped out into the corridor, hearing my heels click and the almost indescribable thrill of being outside of the safe area. Until I panicked about whether the door would shut and lock me out, forcing me to walk down three flights of stairs in three inch heels and ask nicely at the desk if the 6ft2in transvestite 1950s housewife could be let back into his/her room. And hell, that thrill was another thrill.

And also just the thrill of being in an area that had been used by hundreds of people was oddly thrilling. Pretty sure my boss had stayed in exactly that room (I remember lying on the carpet at 3:00am in drab mode trying to put my back back in after spasming a muscle. And the idea that I was now in that room in full femm was thrilling.

So anyway, that’s why this outfit makes the list. It reminds of the night that Sarah got to be Sarah for a change, rather than him dressed as Sarah.

8: Strict Dom, submissive secretary….

I have a thing for women in high necked blouses and tight leather skirts. There, said it. It’s a standard thing for a lot of blokes, that little touch of the strict dominatrix, her black patent heels clicking as she walks around you, her stern eyes behind glasses, sensible yet oddly sensual haircut, the high necked blouse a counterpoint to her sexuality. You get the picture.

Course, while growing up and fantasising about being around and with women like that it never really dawned on me that I could, well, *be* that kind of woman.

Until I was. I found a lovely high necked black frilly blouse, Cindy provided an indecently short leather pencil skirt, and the combination literally blew my mind.

Cards on the table here – I don’t get aroused when dressing and doing a session. Never have. For a start it’s a little rude to the person doing your makeover, and secondly, in a very Sarah way, I don’t want to spoil the illusion in the photos by seeing a package ‘down there’ where there really shouldn’t be one.

But wow. When I first looked in the mirror and saw this woman looking back at me I literally had to step away and stop looking. It’s pretty much one of my biggest post-puberty fantasies, there’s something about that look that just reaches down into my lizard brain and tells me to put ‘mistress’ at the end of every sentence when talking to her.

And to see me looking like that was huge. Didn’t help when Cindy suggested at some point (and I *really* must take her up on the offer) we could do an escorted outing to a London club that has Dom and Sub nights. I can imagine myself ordering a scantily clad male slave to fetch me a drink. And the worrying thing? I *can* imagine doing that, and in this outfit, who would dare say no? 🙂

7: The Quiet Housemouse/Housewife

I really like this outfit more than I should. For a start it’s a dress that real women would rarely choose to wear, a dress that reeks of domesticity and is a bit of a throw back to the 1970’s in terms of its large collar and pattern. But when we did the look something just clicked – the style of hair and the clothes just brought out the shy housewife in me, and every picture was a gorgeous portrait of a stay-at-home wife.

Now, we’re straying into dodgy territory here. Why a middle-aged bloke who spends his time scowling at everyone, being miserable and world-weary, would get such a thrill out of presenting himself as herself to the world in such a submissive way really begs some questions, but hell, it’s my birthday. Is it emasculating? Absolutely, and wonderfully so. Is it sexist? Very probably, but given the fact the woman who is the domesticated, submissive, eager-to-please new wife is in fact me I’ll chalk that down to pleasant self-abuse.

But putting the obvious questions about my damaged psyche and crumbling masculinity aside, I *love* this look. She’s so cute, I just want to hug her. And the dress/outfit was a joy to wear, especially the pink heels. That added just another wicked little kinky touch, in my humble and damaged opinion of course.

And another reason why I love this look so much? I can’t see me there at all, only a comfortable housewife in a pink frock. Result.

6: The unbelievably feminine feel of Taffeta

Unless you have ever worn a close fitting and/or flared frock made from Taffeta you won’t know what I mean when I say it is like being wrapped in a feminine cocoon of loveliness. For a start, when you button it up and it falls around your legs, it feels cold, like you’ve been wrapped in satin that has been in a fridge for a while. Then as the dress responds to your body heat the way it feels is just indescribable.

Bloke clothes are uncomfortable by design. Yeah, you can buy silk undies and the like (I was about to make a blokey crass comment about the type of people who buy and wear male underwear of that kind of material but given this blog has over 100 articles about how I love to wear women’s clothing that would be pretty much the pot calling the kettle the blackest of black – as I end a number of amusing statements to Cindy ‘says the man in the dress’) but for the most part everything is rough.

But women? Wow. In the picture above I had wonderful black stockings on against hairless legs, a corset and bra, but other than the standard form shaping undergarments required for, err, my kind of woman, every other piece of skin was directly against the frock. And it felt sublime.

When you walk in a dress like this it shimmers around you, and, if you’re anything like me, you just can’t help but laugh. It’s like being massaged by angels.

Plus, getting back to (near) normality, what a style – another of the Vivien of Holloway Kitties but this time a ‘luxury’ one, and that’s not telling the half of it. All women should have one of these, says the man in the frock.

5: Every Woman I craved in the Eighties

A little story that will probably reveal a lot about me that I didn’t realise, because I’m an idiot. I remember sitting in a pub in Bristol in the mid eighties, the Bristol Bridge Inn. It was a Tuesday night, the night myself and my little cabal of friends (all into heavy metal) would go to a dive club called The Bierkeller. Near the Bierkeller was a night club where all the ‘trendy’ people went, and, to make myself feel even older as I approach my 50th birthday, these people were into such bands as Duran Duran, Wham, Madonna and the like.

I have very few vivid memories of that part of my life, and the time before, which is indicative of the bloody awful childhood I had (my mother made me the woman I am today, he says both ironically and deadly seriously), but I remember this night, or at least this moment, like it was yesterday. We were sat at a table next to the door, nursing pints of Guinness and whatever tepid lager they were serving, when two women came in.

Now back then when trendy women went to a night club they would power dress as if they were executives of a company – peplum suits with massive shoulder pads, big hair, makeup done perfectly. And I can remember exactly what these two women were wearing – one had a gorgeous blue dress on with a pencil skirt, flared peplum skirt at the waist, large shoulder pads, a stain material. And the other one looked *exactly* like I do in the picture above.

The amusing thing? I can’t remember their faces at all, but I can see their clothes like they are stood by me today. Yeah, yeah, the message is obvious. But the point of that revelation is this look was the woman/women I was in love with in 1985.

And now it’s me. Again, that lovely little naughty buzzing thrill that goes from the middle of my brain right down to my toes like a little electric shock kicks off at that thought.

4: Didn’t every little boy want to grow up to be Audrey Hepburn?

No. Just a few of us with certain ‘special’ difference I think. As you might have worked out from the angst and oddles of postings I do around the urges I seem to get to embrace the feminine role as well as the look I love getting into the mindset of the women I dress as. It’s part of the fun – 99% of the time it’s about the mortgage, the piranha tank that is my career, getting the car serviced. Whenever I have the chance I want to create and become something different, to experience the world from a pinker angle. This look was trying to nail something that had been scratching away at my soul from within with a delicate pink nail for years – I wanted to look a little like Audrey Hepburn.

I’ve never bee a fan of her films as such, but she was just so bloody stylish on so many natural levels, and the era she was around in just ticks all of my inner, cough, Hepburn. So this outfit was a full set from Vivien of Holloway again, a 1950s style blouse with mid-arm length sleeves, a huge circle skirt with polkadots on it, a couple of petticoats and a handbag to top it off. Pretty expensive but when it all went on, when the wig was in place and I could stand from Cindy’s makeup chair and do a twirl, my world nearly fell apart.

The rush of emotion seeing the skirt flare out, seeing how happy I was, was mind blowing. Clothes shouldn’t do this to you, but if they do, wow. And, as if to get in on the fun, my mind started to absorb the role as well – my wrist bent daintily in all the pictures, my feet found themselves posing in ways that really required a lot of concentration on balance (although with petticoats and a circle skirt you do get this odd feeling of being balanced, albeit very wide).

Just gorgeous to wear, and gorgeous to *be*. No wonder Audrey was always smiling.

3: Mother Dearest

I’ve gone on and on about this look in other blog posts, but I find myself going back to it a lot with a morbid fascination. Not only does it look nothing like me, it also isn’t the outfit or look that ‘women like us’ go for. In fact it’s bordering on that horrendous thing that older women refer to as ‘being invisible’, where they reach a certain age and men stop seeing them.

For me, I love this look for reasons I can’t explain. For a start, the frock is just perfect in a 1980’s mom way. To be honest, it’s quite an ugly dress as it stands, but the combination of restrictive collar, mid-length sleeves, floral striped patterns and a doggedly determined ‘feminine but not sexual’ style is just wonderful to wear.

It comes back to experiences. It’s great to dress in body hugging PVC (see the top image in this blog where I’m doing a very good impression of a shop-window dummy), but for me it’s also one hell of a thrill to dress as the mature housewife. In fact this is one of my favourite dresses – it’s hanging in the cupboard next to my too large collection of Kittys and various other 1950s inspired frockage like a reject from the 1980s.

But I love the impression it gives. Suddenly I’m a mid-50s wife, and that’s an odd but wonderful sensation. Given my advancing age at least I know I can rock a mumsy look, appeal to the older admirers as I walk faster and faster towards the grave.

2: OUTSIDE!!!!!!!!!!!!!!

Yup, that’s a terrified and mildly drunk me next to the gorgeous Cindy during the last time I dared to venture out to the Wayout club. I wore a lovely 1940s tea dress, dark blue with a red floral pattern, and was utterly and completely scared out of my pretty little mind.

I’ve blogged about the experiences (being asked if I had a penis and then if I’d like to suck someone else’s in the space of forty seconds was remarkably eye-opening) but it’s worth remembering that I walked a couple of streets of London to get to the pub dressed in just this frock, a pair of killer heels (black patent with metal heels, just a literal wet dream of sexiness), mingled in the pub, ordered a couple of rounds, used the ladies and finally walked those two streets at around 1:30am amongst a plethora of drunks IN THAT DRESS.

As far as the outside world was concerned I was either a well dressed transvestite or a rather tall girl obsessed with retro clothes, which is a big thing for 99% masculine-time me. For example, buying a round of drinks – I tottered to the bar, saying excuse me to the number of groups of admirers stood around in their trousers holding their beers, stood patiently and as femininely as I could in the queue before standing at the bar, hips slightly canted for that bum-out position, ordering a round of drinks while the man next to me stared at my legs, arse, breasts and finally face before winking.

I can’t describe a: how much energy and guts that took to do and b: how absurdly thrilling it was to do. Hell, if we look at it logically it’s just a piece of clothing, but wearing that dress, a full face of makeup and a more than liberal spray of Chanel No.5 and suddenly you feel completely exposed and thrillingly different.

Plus the frock is something else. I have the same style in a WW2 green *and* a black with white polkadots, and all of them are just a joy to wear.

Oh, and by the way, if you were kinky enough to wonder what my answer was to the ‘sucking’ question, it was a categorical no. In fact I think I may have reverted to male mode and told the person to piss off. (remove ‘think I may have’ from that statement). Again, ‘man in a dress’.

1: And the winner is (and always was going to be)…..

Spotting a pattern? Sorry, couldn’t resist. Again, I’ve gushed about this look before but, sweetly, it’s the look I always go and look at when I’m feeling down. To me *this* is Sarah, this is the woman I love being, albeit not very often. This is the girl I imagine I could take to the pub and have very long and very boring conversations (for everyone around us) about just how wonderful this style of dress is. Then I’d kiss her of course, but that’s another story for another day (involving a shrink’s couch probably).

Pink is such a feminine colour, and the style of this dress just accentuates the femininity of it all. Interestingly a lot of the women who buy this dress (Vivien of Holloway has oodles of different patterns – in fact for my next session after my birthday I have a couple of special ones to model, an animal print one that is so gorgeous, and another of the Taffeta ones but this time a beautiful silver one with black stripes….. dribble) take out the shoulder pads. But to me they are what makes the dress shape so delicious to wear and, of course, see my eighties history for my love of shoulder-pads.

So there we go, a self-indulgent look at my favourite looks in the last dying days of my forties. So long 4x, you were fun and Sarah really had a lovely time.

Stay beautiful and don’t obsess about your age – you’re only as old as the woman in the mirror looks.

Pictured – no captions today as the article was one big caption, but Happy Birthday my beautiful alter-ego-ess 🙂