[Philosophy] The Unnatural Nature of T-Guilt

I’m going to come off as somewhat of a drama drag-queen in this post but I promise it’s cathartic, and hopefully resonates with a lot of you wonderful readers. An the usual caveat – I spill the beans and bile and straight after I’ll write a fashion-centric post to cleanse the palate. Plus, you know, some gorgeous pictures to counter the middle-aged whining, as always.

I’ve been thinking of giving all this Sarah stuff up. Yeah, I know, I’ve talked at length in this blog on the ups and downs of the life we lead, but for some reason, maybe because the world is a darker and much crapper place at the moment, it’s been a tough couple of months.


Pictured – much tougher than all that ironing, she says sarcastically.

And I know exactly why I am having these thoughts. Because I no longer seem to have the T-Guilt. And oddly enough, without that little touch of guilt Sarah seems, well, normal, and part of me. And I don’t want that – I want and need her to be special. Plus, you know, the usual new year blues, disgust at the state of the world in general at the moment and the standard January bleh.

So, I want to talk about the t-guilt, why we have it, and why it is actually an essential component, for me, of everything Sarah is.

We live in a phallo-centric society. Try as we might to pretend to be enlightened our treatment of each other is just abhorrent at the best of times, and the way the sexes treat each other is mind-boggling unpleasant. Courtesy of the temperature in my father’s testes at the time he impregnated my mother I ended up on the male side of the spectrum (yeah, barely, I know), which gave me a growth spurt at around eighteen, body hair that Chewbacca would be impressed with and an occasional urge to shout at the world. That was testosterone.


Pictured – yeah, testosterone. That’s how much bloody stubble grows *during* one of my sessions. I kid you not (nails and smudged guy-liner kind of give it away).

Testosterone in blokes makes us angry, short tempered and all round aggressive and annoying. It also means that this gender is the dominant one, and, as I said earlier, even in a post-feminist society the advantages and unfairness of the system are plainly evident. I’m still appalled and amazed there is a difference in wages. Women are still treated as the fairer, and the weaker, sex.

And, going to admit it as I have before, that difference and that change in treatment is one of the big things to me around my urges. I don’t want the aggression, I don’t want the dominance. I’m happy to be submissive, happy to adopt the look and tole of the fairer sex, partly because I find the company of women just so much easier than the usual dick-size dynamics of dealing with blokes in any numbers more than two. There’s a part of me, which I call Sarah, which has those traits that you don’t find in men – a gentleness, an appreciation of the softer things, a need to be pretty.


Pictured – yeah, I know it’s me, but I’m still in love with her.

But I also have the testosteronal maniac in there as well. And when Sarah is in ascendency he, forced to the back of my mind, feels t-guilt. That guilt is ingrained from a lifetime of being told that masculinity is something greater than femininity, that adopting the mannerisms and the look of a woman is somewhat demeaning to a man. There’s even a word for it – emasculation.

That guilt is every angry 1970’s father, every bigoted drunk in the pub after a couple of pints, every, amusingly, sexually confused male that feels something different to what society has defined to be the norm.

And we treat those urges to be gentler, more feminine, as bad. It’s somehow a terrible moral crime to want to be softer if you happen to be born with external genitals.

What we need is a t-feminist revolution. Imagine what would happen in society if all of the people who keep this to themselves and torture themselves stood up and demanded the same recognition as everyone else. Yeah, as I said we barely live in a world where women are treated as effective equals, but, with a touch of humour, we have the advantage of not only being soft and gentle but also ‘blessed’ with the angry-juice.

Instead of burning our bras we could wear them, proudly. *Cough*.


Pictured – if I showed up to work dressed like this roughly a third of my co-workers would be disgusted, a third wouldn’t care less and the other third would be secretly texting me asking for dates….

But anyway, as per normal, I’ve digressed. That guilt is what tortures a huge amount of people in the same situation as me, especially ones who are hiding their true nature from loved ones. Chuck in a society that was so close to proper acceptance before the moral-majority and rampant sexist conservatism stopped the rainbow-coloured train in its tracks, and we are teetering on the edge of the t-lifestyle becoming almost illegal again.

My problem at the moment? I stopped feeling guilty. Which should have been a wonderful thing,. And once I stopped feeling guilty I lost something special about what makes that part of me something I need to cherish.

Now, I can’t go back and start being guilty again, that’s not healthy or even possible. And who wants that? Guilt sucks, no matter how much it contributes to a delicious fetish. So I need to find a way to make her special again. For a start, I need to stop deferring to the ‘let’s get rid of the girl’ reaction that is so prevalent amongst us ladies. That would be insane.

So my plan is to let her out of her gilded cage less often, but when I do make it more intense. Make it a fine wine, the last mouthful, rather than a box of red from the supermarket, available on tap whenever I feel the urge. It’s one of the counter-intuitive things, at least for me, embracing her completely and going bananas on letting her out cured my guilt but made my time with her less important. It normalised my feminine side, and she’s too important to be a normal part of me. And who the hell wants to be normal nowadays?


Pictured – of course, one man’s normal is another woman’s oddness

I will never transition. I have some wonderful and lovely friends who have and will, and that’s a choice I firmly stand behind them for, but for me it’s not about being Sarah all the time. As I’ve said before, if I went down that route I’d end up sneaking out of the house and finding a make-up artist to ‘man-me-up’ for a couple of hours, maybe an escorted visit to a proper pub, chat up some birds, etc etc. What I’m saying in a crudely amusing way is that it’s the radical difference to my daily life that makes Sarah so bloody wonderful, and to be bloody wonderful she needs to be rarer.

So, rather than doing the standard binge and purge (guilty, sic, as charged), I’m going to make the time I am Sarah more precious. That sounds like a plan. Beats waiting for all of us to turn up to work in our best Sunday dresses simultaneously and start the t-feminist revolution. Which would be nice…..

Anyway, thanks for sticking with me on this one. It’s been a weight on my mind, a hollowness when I look forward to the next visit to Sarah that had me thinking her time was over. But that’s not the case.

Vive l’trans-revolution!

Stay beautiful and try not to over think things the way I do. Down that road lies madness.


Pictured – guilt-free…


5 thoughts on “[Philosophy] The Unnatural Nature of T-Guilt

  1. Oh Sarah! 😮
    I hope you are alright?
    I do understand what you’re saying and your reasons for doing it too. I know that you have hinted in the past about this situation. Please know that as your friend (and a good one, I hope!) I respect your decision.
    Take care sweetie.


    Liked by 1 person

  2. This massively resonates with me, and over the xmas period I was forced to have a longer than usual break…..
    The good news is…. your right, when you do come back after a longer break it does feel special again, exciting, amazing! x

    Liked by 1 person

  3. The guilt and risk of being found out does have a certain attraction for me, my partner is ok with Shirley but my work pals would find my other side a source of endless mockery I suspect. Thanks for sharing thought provoking blog from a similar soul xx

    Liked by 1 person

  4. I totally understand what you mean by “the guilt” . Add in , “the fear” . The fear of getting caught . The fear of the effect on your relationship with your significant other . The fear of being considered less than a man by your mates . The fear of being publicly humiliated – for doing something that half of the people in the world do on a daily basis .

    Yes – “the guilt” , and “the fear”, most certainly are things that most , if not all, of us feel when we explore femininity . Yes, it’s toxic – but, it’s also exhilarating ! Sort of like alcohol – a little bit excites the senses, lowers inhibitions ; but too much leads us to bad judgement, or worse .

    But, the flip side is “the joy” . The pleasure that we get from being a little bit naughty , from transgressing society’s rules, even if in private . Certainly , the joy you feel being Sarah is evident in every photo that you so generously share with us . I think that this is what you feel that you’re losing, Sarah – you feel as though you’re getting too comfortable with femininity . ( As if that’s a bad thing ! 😉 ) And maybe , it might be best to cut back a bit , temporarily , on Sarah time, to get your feelings sorted . But, I hope that you don’t consider abandoning Sarah totally – she’s a part of you , a very significant part , and cutting her out of your life totally would immeasurably diminish you .

    (( ❤ )) !

    Liked by 1 person

  5. Hi Sarah, The most horrible thing about guilt (and as a lapsed catholic, I am an expert!) is that when I was a “girl” in my teens and early twenties and the guilt came crashing down on me, I knew I was going to hell for my sins. As a penance, I would bag up much of my female attire and dump it somewhere. For instance, I would fill an old suitcase with my female attire and leave it on a train. Even that would create more guilt because I would fantasise about what the guy who opened the case would think. Even worse is that I would dispose of all the photos I had of myself en femme. Oh how I wish I still had them! Guilt is a soul destroying emotion and luckily, I eventually overcame it. With Love, Sylvia xxx

    Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.