[Philosophy and Self-Flagellation] Midlife Crisises, Satin Retro Frocks and Sexuality.

Yeah, it’s going to be one of those. I promise I’ll do a frock-tale right after for all those obsessed with pretty dresses (which is also me, to be honest), but I need a little vent.

It’s been a while since I posted. As a midlife-crisis ‘enjoying’ late 40s male I’ve done the new car (Audi, sorry), the thoughts of insane danger sports (cycling, bungee jumping, riding the 24 hour Tube), changing career, all those things that people of a certain age tend to do when they feel their lives are getting a little, well, boring and mortal.

I’ve talked before about the standard tranny ‘purge/purchase’ cycle, and how I am beyond that. Well, not strictly true. Since my last sessions which were sublime, even the fondling/groping/hope-I-don’t-get-raped experience of tarting up and going to a trans club, I’ve been asking myself some serious questions as to the whole ‘girl in my head’ thing.

I love Sarah. There, said it. But I still refer to her as her, and not to her as me. Even after I promised myself I was open with it, that it was part of me, yadda yadda yadda. And as an ageing person with a waistline that seems to have a mind of it’s own (regardless of the good stuff I eat it still wants to turn me into the human pear) I look at the photos of her and I am starting to not see the fun retro-girl and start to see the midlife crisis man.


And I know it’s all context, all perspective. I get a lot of very nice comments from people on Flickr and Facebook and like all people raised by the tail-end of religion I assume they aren’t true. As I’ve mentioned before, depression isn’t something that makes you more rational…..

And the weight thing. Bloody hellfire, I’ve spent my entire life not giving a single care in the world to what I eat or drink because, well, bloke and all. But since Sarah re-emerged it’s like I’ve developed an eating disorder. Everything makes me feel guilty, looking at a chocolate bar makes me wonder if it will tip me up a dress size. That’s not a normal reaction, unless you happen to be a woman, so on one side, cool, on the other, not good.

Doing a tonne of exercise in the gym while you are thinking ‘I’m doing this for her, I’m doing this for her’ doesn’t strike me as wholly healthy. Or sane, to be honest. Yet that is what I’m doing, paddling up and down a pool a hundred times when I’m feeling up to it, on the one hand loving the idea I’ll be able to slip into the latest 1940s hostess dress I’ve bought, and on the other hand worrying about whether my legs will look too muscular in stockings and heels.

Talk about confused first world problems.


And while we are on the subject, my sexuality is playing on my mind a lot recently. Granted, I haven’t actually had sex in eight years now so it’s pretty much a moot point, but when you find yourself actively involved in an online conversation with a thoroughly decent admirer and you find yourself suggesting things that make it seem that Sarah may well be, to put it mildly, somewhat of an easy girl you have to start asking yourself just what side of the line you find yourself falling on.

So, aside from providing myself with a little titillation (definition, the arousal of interest or excitement, especially through sexually suggestive images or words, which is pretty damn accurate) what on earth am I talking about in this blog?

For all my talking of acceptance and understanding I find myself pretty much back at square one, although with a huge gallery of photos and some options to explore her sexuality that are really messing with my guilt.

It’s been a fun ride with its fair share of ups and downs, and I wouldn’t change a thing (well, maybe a couple of things) and I’m a little tired of the melodramatics, so I’m making myself this promise.

I’m going to have another session very shortly. I will enjoy that session. And then I will decide whether and in what direction Sarah’s journey will continue. 

See what I did? I did a major copout while still retaining the ability to change my mind. Yay, indecisiveness!

Vent over, next blog post will be back to Sarah’s normalness which is the mad spice that I use rather than dangerous sports to remind me I’m alive. And pretty. Always pretty.

Stay beautiful.


2 thoughts on “[Philosophy and Self-Flagellation] Midlife Crisises, Satin Retro Frocks and Sexuality.

  1. Oh Sarah!
    I do understand some of the things that you’re going through. We both know that a part of us -big or small – will forever be feminine. The feelings that we have to deal with every day, are also felt, I’m sure by thousands of other people who are also in our situation. It’s how we choose to deal with it that decides how we get through it. I know how strong you are and I know all too well the ups and downs, the purging and the guilt. And I know that pretty much at the end of the day, we will still have the same decisions to make. And we know that they will be life changing. Which is why we hesitate and prevaricate.
    And on the sexuality front? I really understand that too. Sexless marriage? The same. An understanding of an almost innate need for intimacy is a part of all of us too. Sometimes we can deal with it ourselves and sometimes, we yearn for the intimacy of others.
    I’ve known for a number of years now that my sexuality is as fluid as my gender. I also know that for me, they are linked. But I’ve never been in a situation where it has become a reality.
    Only you will really know hun. When you’re in that situation that presents itself whether you will go forward, or not. But if you do fall over that line, just make sure it is for all the right reasons. I admit that if your admirer is as throughly decent as you say, then I know I would struggle not to go forward.
    If you need to chat, just let me know.
    Thinking of you.



  2. Hi Sarah,

    After my last visit to Cindy and my struggle to fit into 3 beautiful dresses I Truly understand the watching weight and exercise points you make . “M” would never be this bothered about his weight , yes he knows he has a middle age spread but he wouldn’t be getting up doing ab exercises and then going out for a run 🤬. However that’s exactly what he did this morning and he is contemplating paying £500 for fat freezing without even knowing exactly what it is or if it will work 🤷‍♀️. He is desperate to lose the weight so that Lara-Lilly can fit into a size 16 🙄.

    As for sexuality “M” is deff straight

    Lara-Lilly got a buzz from being smiled at by a man but I’m guessing that was more of an appreciation of being accepted than anything else ?

    Good blog post , keep them coming
    Lara-Lilly x

    Liked by 1 person

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