[Philosophy] Fun is a four letter word.

So, it’s thirty minutes past the witching hour, I’ve been home for an hour or so having just trekked back from London and yes, I’m in the post pseudo-coital glow of having done another two day session with the ridiculously talented and skilled Cindy at Boys Will Be Girls.

And it was a different session. Not in what we did, the usual retro, modern makeup, copious laughter and serious hip exercises (nothing naughty, I’m just not used to the way in which women have to bend when they pose for fashion photography….). But in the way that it was just pure pleasure.

No guilt.

Now that’s a first. A number of the photos have just got pure joy shining through them.

I’ve been down lately, the mix of winter weather, feeling the cold touch of age gradually gripping me in the mornings and evenings, that usual cyclic doubt on Sarah combined with the self-righteous urge to lock the door on the pink room she inhabits in my head and throw away the key. You know, the usual things a forty-eight year old man deals with.

But there was none of that the minute I stepped across the threshold of Cindy’s place, my heart pumping faster than normal because I’m daft enough to think that I’m special and people will go out of their way to point, mock and shout at the not-so-closetted femm-boy. Which they never do but I always assume they will as I stand on the street, waiting for that blissful moment when the lock buzzes and I can hustle my newly shaven body and standard backpack full of glorious frocks into the darkened safety of the entry point.

There was just peace. Like the darkness had lifted and bright, pink, butterfly encrusted sunshine was pouring into my soul.

Yeah, it’s going to be one of those wordy blogs. Sorry.

Getting ready I didn’t feel the normal bittersweet emotions, the slight guilt of taking off his clothes followed by the thrill of the feel of the stay-ups as they glide over my hairless legs, the awkward fumbling to move those pesky external sexual organs back and away before replacing what was a sizeable lump (insert testosterone-powered size enhancement comment here for effect) with a smooth flat surface, complemented by padded buttocks. Usually there’s a pang, a ‘what the hell am I doing’ moment, a point that the drab, boring part of me, fuelled by unpleasant childhood memories and an urge to be a ‘real’ man, whispers insidiously in my ear – ‘Just pay her, put your comfy jeans and T-Shirt back on, we can make the early train back, you’ll feel better if you don’t do it’.

This time, nothing. Just a warm pleasure and a delicious little thrill knowing that the next hours would be spent gradually transforming, one delightful step at a time, into Sarah. The pock-marked, age and stress ravaged face disappearing first under a light-coloured foundation that always makes me think I look like Data from Star Trek – The Next Generation, then blending, eyes, lips, a wig cap, her hair.

I enjoyed the process, it felt….right. It felt….normal. It felt….f*cking good.

All the old doubts had evaporated like dust before a fire. Some part of me wants to type that again, because it’s a huge thing. It was like a click where the imbalance, the need to be him 100% or her 100% and never a blend, just melted away.

It could be just the levels of gubbins in my brain sloshing back and forth between deep depression and mad elation, but it didn’t feel like it. It felt like I’d just stuck two fingers up to the false world, the false rules my mind has tried to impose on me since I was a kid. And the thing that was most stunning was the realisation that i was taking a lot of my energy inside to remain guilty. Having the guilt fade away seemed to lift me, almost like a sigh, and I found that there was suddenly more bandwidth in the head to enjoy the things that were more of a guilty chore before.

Cutting a long story down to a slightly less long story, I had an utterly joyous couple of days revelling in being Her. With no emotional side-effect.

So what does that mean in English? Firstly, it means I have to stop bloody over-analysing it when I feel good. And just feel good. It’s not a crime to feel good, unless whatever you are doing to feel good *is* a crime, but you see what I mean. Secondly it was a lovely realisation that I was being a labellist. Calling myself Her and Him to indicate when each of them was in the house.

Newsflash Sherlock – she is you, and you are her. He is her, she is him. It is all you.

But anyway, before I talk myself into some kind of metaphysical infinite loop and pop out of existence in a wonderful cloud of rainbow particles, I just want to say that on a me level I felt happier the last couple of days than ever before. And given for a large chunk of those days I was corseted, smiling, posing, aching, tasting lipstick and hair, I think that me was also all of us here in this merry little meat sack.

Fun can be a four letter word. And not a rude one.

So, to lighten the mood and make this blog sound less like a giggly schoolgirl wrote it, here’s the Sarah’s that showed their beautiful faces the last couple of days….

Valentine’s Night Sarah

Slightly awkward and not winning me any prizes in the ‘remembering false holidays created by corporations to take your money’ stakes I booked session day one on 14th of bleedin February. I showered my other half with pressies, which I do on a weekly basis anyway, and then went off to London for the night. But hey ho, first look Cindy created just made me smile a lot and I have thoughtlessly called her ‘Valentine Night Sarah’. Grant me my usual unsubtle attempt to sexualise the looks but hell yes, I’d do her in a heartbeat. And so would most of you…



Senorita Sarah

A very cheap costume combined with a number of Cindy’s accessories became something very stunning. It just worked on a raw level, this look was so much fun to wear that I would have danced. If I could dance. Which I can’t. So I made up for that by waving some fans around.


I can’t be the only one that finds that attractive….

Hen-Night Sarah

Also Bridesmaid Sarah, this was a frock I’d bought from LindyBop a while back along with a cute little pink lace shrug, and then kept them in my cupboard because they didn’t feel very ‘Sarah’. Turns out that if you combine them with some very nice false mammary glands and some beautiful hair, you get Bridesmaid Sarah, very cute and taffeta-flouncy. Again, wonderful to wear and just so damn sexy… And those shoes. Gibber.


Posh Business Frock Sarah

Again, another frock that has sat for a long time in the half of my small cupboard that Sarah, I mean *I*, keep my feminine attire in. I wasn’t sure if it would work, but Cindy’s marvellous makeup combined with the cutest wig made it come alive. It was also worryingly comfortable to wear, which leaves me to think that at some point in the future when I’m feeling particularly obtuse I might employ Cindy to recreate this Sarah and walk into my companies office wearing this outfit. Wonder how long it would be before someone spotted the photo on the security badge was an overweight, bearded man and the woman sat at the desk was, well, this:


Given the ultra-sexist nature of some of the people I work with, quite a long time I’d guess…

Secretary Sarah Re-Visited

This was a similar look to the wonderful creation Cindy did at the previous session with the leather skirt, high necked black blouse and I have to stop there or go and have a cold shower. This look was a low-cut see-through green/white polkadot pussy-bow blouse with a lovely little skirt and, hell yes, I’d do her because she is just so cute. Anyway, where was I?


See why my mind went off on a tangent?

I’m Sarah, Fly Me!

I’ve waited a while to get to use that quote…. It will mean nothing to anyone born after 1975, but there were some adverts in the states that were either not thought out at all, or, more likely, utterly thought out to achieve the rising of male interest. It was an airline, and they had all these seriously cute Stewardesses speak their names to the camera, ‘I’m Bobbie, Fly me!’ etc. Not even subtle but it worked. Anyway, I found a costume that was almost a Pan-Am uniform and we had some fun. A bucket-list entry this…



I’m a huge Trekker. Note, Trekker, not Trekkie. I’m *that* much of a nerd. So I always had a bucket-list entry of finding a proper Star Trek uniform for Sarah, I mean me. I managed to get my hands on a uniform from the new set of films, specifically Dr.Marcus from Into Darkness, and with Cindy’s exquisite skills we created this….


Another bucket-list tick. And the thigh-high leather boots, whilst not strictly speaking part of the official Trek uniform, were suitably kinky.

Mummy-To-Be Sarah Take Two

Yeah, I didn’t learn anything from the previous blog-post about Taboos and the like. So we did preggers-Sarah again, this time with a cute little top and some black lace leggings, plus sensible shoes. Can’t go wrong with that ensemble really.


1940s Cute Frock Sarah

Thought I’d forgotten the Retro stuff, eh? Think again – this frock was in my cupboard for a while, fell in love with it on the LindyBop site. We changed the collar and went for a cute 1940s land girl look, and I think we nailed it.



I love the Francine frocks, which I think I mentioned before in a Frock Tale posting a while back. I wanted to re-visit the frock, mix in a huge dab of Stepford Wife and see what came out. This did, and I’m very happy that she put in an appearance. I would do her but only after putting a ring on her finger.


1950s HouseWife Redux

I have a soft spot for this frock, so we decided to use the look from the Francine outfit and see how it looked with the 1950s frock. Again, loved it to pieces.


1940s LindyBop Tea Dress Redux

As with the Francine this was one of my very first frocks in my very first Cindy session, so I wanted to bring it out of retirement and see how the new and improved (i.e. thinner, happier and not as terrified/rigid) Sarah would look like. Turned out nice.


Kitty Klaws, Porno Star Extraordinaire

Not sure I’ve mentioned Kitty Klaws. We did a prostitute look at the last session and it went down a storm on Flickr (and in my pants, not going to lie). So this time I wanted to have some fun with her. I bought a silk robe and we did a whole set of very fun pictures as if she was between scenes in her latest porno. Yup, sexist, but I’m not sure sexism counts when it’s yourself….


And that, dear readers, is why I have a smile on my face that you couldn’t displace with explosives.

Stay beautiful and, if you can, find your happy place.



2 thoughts on “[Philosophy] Fun is a four letter word.

  1. I’m really happy that you had another great time with Cindy. It brings a smile to my lumpy, bewhiskered (for now) face knowing that you not only got to let Sarah out but that there was an epiphany of sorts. A reconciliation of your socially indentured sides. That is real progress! A knowing and an acceptance that all of these aspects are still you. I would suggest calling it gender euphoria but what do I know?
    I love all the different versions of Sarah that you have shown us and I’d be very hard pressed to say which one I liked the most. I think that, in the spirit of your post I should say that I like them all equally as they are all you.
    Stay well and keep that joy and euphoria with you always. It’s who you are, after all.

    Liked by 1 person

  2. What a wonderful session! No wonder you enjoyed it so much. You look so excited and so beautiful in all the photos. My fave is Valentine’s Night Sarah because the dress is fabulous and you look so sexy and – more important – so available. I definitely would! Lots of Love, Sylvie xxx


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