[Fashion]1088 days. 1 session. 13 looks.

Actually, 31,344,748. That’s the number of views my pictures on Flickr have got since 2010 (well, not 2010. I created the account as an admirer interested in some of the gorgeous looks the girls have. Didn’t start posting Sarah, or Debbie as she was then, pictures until 2014). I guesstimated that it was an average of three seconds a look (maybe a bit more if the hand was out and the pants were down, if you get my meaning), did the math and et voila. 1088 days of real time.

That’s just unreal. I still think of myself as the closet transvestite who is sneaking out on the interweb, That position has looooong gone. 1088 days ago, it seems.

Anywhos, apologies for the pause in writing up the last session. I’ve been very meh lately, combination of changes at work (I hate changes0), the hot weather (I hate hot weather) and the fact I’m rapidly approaching the ‘fifty’ birthday. Not that that means anything, it’s a yearly number based on some bad math and oddness (go read-up on the Julian calendar), but it’s a figure. I’m closer to the cold, dark emptiness of the grave than my arrival. But hell, I don’t remember anything before 2001 so technically speaking I’m 18 (not actually true, memory may have been affected by copious alcohol and self-abuse).

So the last session. If you read the LiveBlogs you would have seen it was, err, a little fraught. Scratch that, it was bloody insane. Courtesy of my other half (who I have not forgiven yet) letting the cats out, because I wasn’t there and I get very, very paranoid about my buds being out, our favourite, a cute lump of fur with very little common sense called Murph, went missing for thirty hours right slap in the middle of my planned three day session. In fact the little sod didn’t show up until I was driving down the M42 in a thunderstorm was faintly ironic and very annoying – you know the type of storm, where the rain is falling so hard you are sat in your car and can see absolutely nothing. That odd moment when you think ‘I’m going to die embedded in the back of a stationary lorry and I won’t even know what has happened’.

Anyway, water under the (*&&$^$*&^$*$) bridge. Suffice to say I got myself to Cindy’s for 10:00am on a Saturday by sleeping sod all hours, up at 3:45,am train at 6:00am, albeit having had around five actual hours sleep in the preceding five days, so to say I was exhausted would be like saying I like Kitty frocks from Vivien of Holloway – a massive and misrepresentative statement. I also managed a brief session the day before the day before, in a rented apartment, where I did three frocks/looks and then spent all evening en-femme drinking beer and making frankly unshareable videos (cough, bad Sarah). As a complete aside there’s a lube you can buy on Amazon called ‘Cum 4 Boys’ which looks and behaves just like male semen. Just saying, is all.

So, I had a nine hour session with Cindy, followed up by heading out to the Wayout Club/den of drunken sexist pigs (see previous blog entries for that little soiree). In this blog, which I promise will get on to femm stuff once my alcohol fuelled ranty-ness has subsided, I’m going to describe the 10 (!!!!) looks we achieved and the thinking behind them.

But first, a quick overview of what a session actually entails (for those that are thinking of doing one). I racked up at 9:56am with a huge backpack of femm goodies. Chatted to Cindy for fifteen minutes about THE BLOODY CAT AND WHY MY OTHER HALF THOUGHT IT WAS A GOOD IDEA TO LET THE LITTLE GUY WHO HAS NO SENSE OUT. Breathe. After that I stripped down to my undies, popped on a black silky robe and Cindy started to do her stuff.

First some moisturiser, then a base of foundation – quite thick as my stubble doesn’t know when to not be there (and I’d shaved *at* Cindy’s, getting rid of the 2mm of iron wire that had grown in the 24 hours since I shaved for the apartment session. Then about two hours of Cindy’s magic. Now, I have a thing about eyes (I was in the military and saw too many training videos on torture). I don’t like people being near my eyes. When Cindy does the eye makeup it’s, well, a bit tough. I have to bite my lip (no problem there as she does the CSL/DSL (have a guess πŸ˜‰ ) at the end) and try not to squirm back into the seat. It’s the bit I hate the most – I may have mentioned that the whole rigmarole of doing the makeup leaves me cold – I’m a product tranny, not a process tranny. I get no thrill from the effort it takes to transform drab him into fabulous her, I just want to be fabulous her. In fact I suggested Cindy could make more money out of offering an anaesthesia service. You know, show up, bit of gas, wake up a girl, et voila etc.

Anyway, after two hours the base of Sarah is there, beautiful makeup. I take a chance to have a pee, because I’ve reached the age where a single cup of coffee seems to translate to five or more visits to the bathroom, and then it’s the foundational garments. I have a lovely girdle which doubles as a way to ‘hide the tackle’ – it’s a 1950s style tight single piece that covers the crotch but pulls in the lower bit of the stomach – not the beer gut, bless, I have a much more sever tool for that. So the girdle goes on, then the stay-up stockings. After the makeup this is the bit where Sarah starts to appear, the feel of pulling stockings over hairless legs is like no other feeling, period.

Then we do the nails (spot the pragmatism? Yeah, putting on stockings with talons is part of the overall female experience but I’ve done it once and to be honest I don’t want to have to buy five pairs of stockings for a session). We used to use acrylic colourless and then Cindy would paint them (while I huffed the fumes of the nail varnish, again, bad Sarah). But now Cindy has the really cool pre-painted ones – for this session we went for some lovely pink ones for a change.

Then the corset. That’s where it starts to hurt, all the internal organs move about and the bottom three or so ribs end up poking into the base of my lungs. But *totally* worth it, the beer gut disappears and Sarah’s hourglass figure replaces it.

Then we stick the wig cap on. I always mimic someone putting staples in, or using a nailgun to do it.

Oh yeah, forgot to mention – I take the photographs and posing of Sarah very seriously but everything else? Not so much. It’s a defence mechanism, when you’re a 49 year old man wearing full femm makeup and gorgeous frocks you’ve got to keep hold of some tiny bit of him. Or it gets a little odd (says the man in the dress).

And then we can start. Cue seven hours of outfit changes, posing outside and in the photo studio, much tottering around on heels. When the session finishes I normally can’t wait to ‘do the scrub’. Well, that’s not strictly true – I can’t wait to get the corset off. The moment that bad boy comes off is like the post-orgasm rush, seriously. Suddenly I can breath again. Recent sessions have seen my body, err, not rush to go back to it’s original shape, which is a bit of a giggle.

Anyway, we’re 1300 words in and haven’t started gushing about the looks yet. So here we go – all ten looks we pulled off in seven hours πŸ™‚

1: VE Celebration Day Sarah

The first look is always a warmupΒ  even after two hours of makeup application and all the foundation garments I’m still pretty much him at this point – I need to relax, start to channel her, so I tend to pick a more simple outfit to start with.

This one was *gorgeous*. A 1940s tea dress in Emerald, a colour you don’t seem to see nowadays in modern dresses. It’s the same fabric and style as the Tiki dress I wore out to the Wayout and the lovely black Polkadot one I wore as one of the three outfits in the apartment (the others were the lovely Lindy Bop Mandarin collar floral dress and my ‘Bank Manager’s Trophy Wife’ frock which we re-did in this session).

The fit of this dress is wonderful – once you do up the buttons at the front and the zip at the side, and then tie the belt in a bow at the front (Cindy did that and I loved the effect) it really highlights the feminine shape. We used a subtle brown wig for this look – I wanted to look like a WREN who was glam-ing up for the VE Day celebrations. Though obviously my lipstick would have been gone because there was a lot of kissing of servicemen on that day.


Pictured – just add servicemen for kissing.

Add a lovely flower for her hair, chunky pearl earrings and sensible yet sexy black shoes and the look was complete. Loved this, it ticked all of my retro boxes and kinda sums up the perfect woman for me.

2: *The* dress, and a full retro look

I may have mentioned this frock before. It’s a Kitty from Vivien of Holloway, but wow, it is the perfect pattern. A cotton-candy pink with white polkadots. When they announced this frock I knew I had to have it – I spent a good 24 hours watching the website, constantly updating it like a desperate woman, until it appeared and *bang*, bought it (and a black one with white polkadots I’ve yet to wear).


Pictured – dribble.

For this look we went full out on the retro. F*ck-me pink patent high heels, the Marilyn wig, a lovely white retro belt I bought from VoH and the same hair flower as the first frock. Plus a tight pearl choker to finish off the ensemble.

Wow. This is *exactly* the kind of woman I’d want to hit on but would be too shy to do it. Plus she’d be way out of my league.

I came *very* close to wearing this outfit out to the Wayout. I only bottled at the last moment and switched to my slightly more restrained Tiki tea dress. Kinda get the feeling if I’d gone to the Wayout as her I’d have had a lot more unwanted attention.


Pictured – Do you want a dance? Or just to pop around the back of the club and perform fellatio? Yeah, that kind of attention…

3: *the* dress, but as a modern Sarah

Though I love the Marilyn wig (to be honest, I never thought blonde would work on me and the idea of having Marilyn Monroe hair was always a fantasy. Who’d have thunk it?) I really fancied seeing Sarah, day to day Sarah, wearing the gorgeous Viv Kitty frock, so we swapped out the 50s hair for this lovely wig that I call the Phoebe, because I think I look like Phoebe from Friends wearing it (though not as mad. Well, not *quite* as mad).


Pictured – dammit, is it narcissistic to be in love with your feminine self? Who cares, I adore her.Β 

Loved this look to bits, it again ticked all my boxes.

4: Stepford 1960s wife

I saw this frock on the Joanie Clothing site and immediately thought ‘yeah, that’s a glorious 1960s housewife frock’. So we combined in with an apron, massive petticoat and a beehive hairdo and there she was, a typical 1960s submissive housewife.


Pictured – another cup of tea, darling?

Yeah, it’s delightfully kinky in an emasculating way and I think that’s why I love this kind of look. It’s a woman that no longer exists, that existed before I was born, and to be her now is a rush I can’t describe. Anyway, got to love a flouncy floral frock that’s impossible to run in. Ooo, there’s a thought πŸ˜‰

5: Hellbunny Cherries

I bought another see-through blouse from Hellbunny, this time with a cute cherry print, and while there I saw a circle skirt with a similar kind of pattern. Now I know that a good girl doesn’t match patterns but I really loved the look, so we combined the circle skirt with a petticoat, I wore a black silk slip under them all to make the blouse more presentable, and used the retro white belt to accentuate the figure. It wasn’t perfect but I thought the look was very cute.


Pictured – cutie

6: Soccer Mom Sarah

And now for something a little (actually a *lot*) different. I was taking off the circle skirt and petticoat when I had the idea of using the blouse in a mumsy, day kind of look. So we squeezed Sarah into a pair of size 14 tight mum-jeans (that really accentuated her bottom), added sensible hair and bang, pretty much a MILF I would definitely go out of way to F.

But trousers felt just wrong πŸ˜‰


Pictured – “Just borrowing the Range Rover darling, the other wives want to meet up for coffee. Don’t worry, we’ll talk about you….”

7: Revisiting Sarah the Secretary

I managed to find an utterly gorgeous red with white polkadots (hmm, spotting (cough) a pattern?). It’s actually a posh make, Hawes and something, but I’ve always had a think, since the 80s, for a woman wearing a blouse like this. I see them a lot on the Tube and try not to stare – not for nefarious reasons but because I’m mentally undressing them and mentally dressing Sarah.

This one was a doozy – combined with a way too short skirt (visible stocking tops) and a pair of glasses and there we go, the office temp everyone wants to get to know.


Pictured – be still my beating you-know-what.

8: The Banker’s Wife

Wow. Shouldn’t be, but by far my favourite look for all the wrong reasons. For a start, there’s a couple of pictures where I look like my grandmother – sensible frock, sensible hair, very mature looking lady. And secondly the dress is everything that girls nowadays don’t want to wear – it’s conservative, a little mumsy (hell, a lot mumsy).


Pictured – it shouldn’t turn me on. But it does. Go figure.

And it’s part of an ongoing story I have brewing in my mind about a guy who defaults on his mortgage by accident, and in order to keep his home where his family is the Bank Manager blackmails him into spending a weekend at a hotel retreat for Bank Managers as his trophy wife. Yeah, straight out of Fictionmania with a side-order of tranny-trope, but the more I looked at these pictures the more I liked them.

In fact, in drunken moments, I’ve seriously considered putting a message up on various TV sites about trying to find an older gentleman admirer and doing a ‘wedding anniversary’ photo shoot. This outfit is perfectly submissive.


Pictured – Yeah, spending way too much time thinking about it πŸ˜‰

9: Dealer’s Choice. Which turned out to be my SISTER.

So yes. Cindy has an amazing eye for a look that I just don’t have and I can tell she is dying to put me into a number of outfits that would scare me to bits. By this time in the session, about eight hours in, I was running out of frocks that I had brought and suggested she might like to have a go. And wow, she went straight for stuff I’d not tried.

Off the shoulder. Never done an off-the-shoulder look before, partly because I think my shoulders are way too masculine, and partly because I didn’t think it would work. She chose a gypsy style outfit with a dark wig. I let her fuss over getting the arms right, the hair right, before I looked in the mirror.

F*cking hell. I literally couldn’t speak. I think Cindy thought I didn’t like it, but I grabbed my phone and went to ‘his’ Facebook page, did a search and then handed her the phone.


Pictured – my sister. No wait, me. A little freaked out….

It was a picture of my sister at a club and we looked identical. Literally identical. It was uncanny and a little shocking.

But such a good look. With bare shoulders! Don’t tell her but I think Cindy should get more Dealer’s Choices with me.

10: The Final Look. Prostitute time….

So, I fancied doing something a little more erotic and naughty as the last outfit, so we went for a full lingerie/high class escort look. And it was a lot of effort, especially after nine hours or so of session combined with no sleep. But it was so worth it.

For a start we had to take off all the under garments – two pairs of tights went on first, along with some serious silicon hip pads. These tights were natural colour, the top being glossy. On top of that went a pair of black stockings, a stocking belt to hold them up, then a lovely black basque, the *huge* breastplate, a silk robe, hooker hair and lots of jewellery.


Pictured – oh yeah, visible nipples. Ooops…..

It was a lovely look to end on. Very top heavy though, played hell with my back. No idea how all these high class hookers do it…..

After the photos I took off all the stuff, then chilled for a couple of hours, still in makeup, before putting on my Tiki dress and going to the Wayout to be sexually harassed. Ahh, the life of a part-time cross-dresser……

Stay beautiful and remember to have as much fun as you can.


Pictured – Sarah’s creator with her creation, the amazing Cindy





7 thoughts on “[Fashion]1088 days. 1 session. 13 looks.

  1. Oh sweetie! This is amazing! πŸ™‚ XX I sooo love all of these looks on you! And yes, I think that maybe you should let Cindy have a little more say in your attire every so often. πŸ˜‰ She has such a wonderful, perfect eye for what works. Gok Wan should quit now! 😊 XX
    I know I like to try different looks but you absolutely nail yours every time! Damn girl! You’re amazing! 😘 Just keep being your wonderful self hun! XXXX

    Liked by 1 person

  2. I think it is always worthwhile to let Head Girl have a “Cindy’s Choice” during the session. The results are often surprising and always amazing and nothing like what you expected.
    “Try this one”
    “That’s not “me””
    “Just put it on”
    “You sure?”
    …………”OMG love it”

    Cindy Knows Best!

    Liked by 1 person

  3. Your posts are delightful to read. I TOTALLY envy your wardrobe and your sessions with Cindy…if I’m ever in London with the chance I would totally book her. And Cindy made a great pick with that look. Not your usual retro quite so much, but you look fabulous.

    Liked by 1 person

  4. Hi Sarah. Ok, I know it’s weird, especially as a hetero man who spends most of his time in dresses, but I can’t help getting a stirring feeling down below when I see (and stare at for longer than I should) those sexy photos of the gorgeous Sarah. You know the ones I mean! I learned long ago that ‘down below’ has a will of its own and there’s no stopping its ‘growth’ when it gets excited. Then the fantasy takes over and
    I wouldn’t dream of telling you what happens next except, of course, that I do dream it! I realize it would never happen in real life, but in Fantasyland, I guess all things are possible.

    BTW, I have that same Hellbunny cherry skirt though I think it looks so much better on you than me.

    Love you lots, babe. Sylvia xxxxx


  5. Hi Sarah ,

    Just a thought , how about number 8 being another one of us girls but in man mode ? Maybe Cindy would be happy to do this ?

    Lara-Lilly x

    Liked by 1 person

  6. Hey Sarah, I adore most of your outfits, but especially the “sluty secretary look”. Reminds me of my wife, when we were first married, she would dress similar to drive me and her colleagues cray, a natural tease!

    Liked by 1 person

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