[Fun] IFAQ on Sarah Stuff

Ye Gods, another post without six or so weeks of brooding in the blues? What’s the world coming to? Actually this is, unusually for me, the third time I’ve started to write this post. Various versions of this post, with vastly different levels of NSFW-ness, have been hanging around my WordPress hub since Feb 2021, but given the lovely response to the last post (with no ‘I thought you were gone’ comments as well) has prompted me to get off what remains of my once fat arse and do it properly.

Basically this is a version of a blog post I did very close to the start of this adventure here, an ‘(in)frequently asked questions’ Q&A style blog. Back then I was a different person, quite literally given the various chemicals flowing around my bloodstream and absence of one tenth of my original body weight (actually more; like most people subconsciously suffering from an eating disorder I can tell you exactly how much I weighed then and how much I weighed this morning. It’s……oddly worrying. 96k/76.8k to be exact).

Pictured – 78.9k that day. And yes, it does feel like a bloody eating disorder

But here’s something fun. This blogpost will have a set of questions I have been asked or have asked myself with honest, accurate-as-of-today answers. However, if you want me to answer a question add a comment to this post with the question and I’ll, depending on the number of brave people asking, either answer in the comments or even do a ‘The Mistress Is In’ blogpost with full answers. There’s a challenge for you, dear reader.

Anyway, here we go. Lots of piccies to look at if the questions get a little uncomfortable.


On social media I get asked this but no-where near as much as I thought I would; for me it’s pretty clear from both the pictures and the captions (and the usernames are normally a give-away as well) that I’m a crossdresser; I’ve never had anyone mistake my pictures for a GG (although some very kind people have flattered me with comments saying this). But I still get the occasional “R U A MAN?” type of question. The answer is yes, biologically. Which sounds like a cop-out (and given my history and current little adventure with the tiny little 2mg tablets it’s an interesting biological question as well), but it’s the truth. Psychologically? I hate labels (down that road lies madness; whatever you call yourself or someone else will inevitably be wrong in someone’s world-view) and I would like to describe myself as ‘me’.

Pictured – I mean, does this look like a man to you? Oh wait, don’t answer that.

R U GAY? is a little more problematic to respond to. Firstly, the first thing you ask a stranger online shouldn’t be that; subtle hint gentlemen, start with a ‘hello’ or ‘you look very pretty’ before trying to divulge if I suck on a first date, please? It’s problematic in that a: in the strict sense of the word I’m asexual with sexualised heterosexual fantasies (boy/girl) where I happen to be the girl, and b: what does it actually matter for the 99.9999% of people asking I’m never going to be in the same room as?

Pictured – not to contradict what ‘he’ is saying but if you dress a certain way and put those pictures up you have to accept that some people are going to be attracted to you

Times have changed. In the 70s and 80s the level of machismo amongst groups of men/boys was such that asking that would lead to a punch in the face for the questioner, or a punch in the face for the person answering yes; a lot of us have that in the back of our mind when we ask ourselves the same question. But as I said, times have changed; society, on the whole, has become rightfully more permissive, as long as you take care, and it allows people to be honest with themselves and with others. Being slightly dishonest I would say I was tending towards bisexuality rather than asexual, but even that is a bit of a fib because I don’t find the (naked) female body sexually attractive any more. Pretty sure I never did; it was all about the clothes and the societal peer-pressure. But I’m also not really anywhere near being intimate with anyone at the moment; I still have the costume and trappings of a heterosexual man, yet all my fantasies (and my dreams which is more telling) involve me as a woman, so we’ll leave that answer at ‘somewhere between asexual and not-a-damn-clue’.

QUESTION 2: Are you transitioning?

No, I’m not. I tinker with hormones, and I don’t do that lightly, because of reasons I’ve said before. I find the stress and life living with testosterone to be too overbearing and I’m getting older now and want to be calm; the hormones I take without permission from my doctor (again, very silly idea) have altered the way I *feel* on a day-to-day basis and I like the way I feel. I may stop or lessen the dose if radical physical things start to happen (and don’t assume if you take hormones you grow breasts; you don’t. Your body balances the different types of sex hormones and, to a large extent, a ‘normal’ man taking female hormones will see some physical effects; my hair has got very odd, very fine, no oil, fly-away. My skin has got very dry; the act of using perfumed lotion every night is delightfully fun. Huge amount of sensitivity in the nipple regions but that’s just the body adjusting to give milk (again, that’s a nice little feeling).

Pictured – lactating does follow on nicely from some of my other noticeable kinks

I said it might get a little NSFW. Anyway, back to the question; no, I don’t see myself ever transitioning. Said it before and I’ll say it again, I don’t want to be a woman but I don’t want to be a man. It’s a good time in history to have that problem.


So, this is always a tricky one. The answer is no for practical reasons; 99.9% of the time I’m a surprisingly scruffy middle-aged idiot (albeit one with features that are gradually but noticeably feminizing). I don’t get much time to be ‘me’, and that time is precious to me. I’d love to meet and in an ideal world where I had no relationship commitments, was thirty years younger and was dressing all the time I’d be out and about.

Pictured – just the fantasy woman I’d like to meet. That sounded rightfully vain. And accurate.

But the reality is the feminine ‘me’ exists for a very short time, and that time takes a lot of effort; I can’t do makeup to save my life and dressing sessions for me involve a huge amount of traveling, stress (I still get scared and my body gets a lot of stress in the weeks leading up to a session; I get spots which terrify me because they will show up, issues with my eyelids (oddly enough because of the lack of oil because of, cough, high levels of eostrogen) and tiredness. I have gone out a couple of times but I end up being destroyed for days after.

I get a lot of ‘can I have a vidcall’ type requests as well and it highlights one of the things that always gets me on the Social Media side. The presence we have, forced upon us by the way that Social Media works, isn’t real; you’re disconnected from interacting with real people face-to-face. You can soften your pictures, or completely change them if that’s your thing, and that’s your online identity. Who you are in real life doesn’t effect that presence, but what people see on the Social Media sites is what they associate with you. So all my pictures (she says, modestly) show a fashion conscious, well made-up and presented woman/crossdresser. When I get a vidcall request I’m often sat slouched in bed, face full of stubble, comfy pyjamas on, often with a can of beer or a glass of red wine.

Pictured – after 9 hours slaving at a computer screen I’d love to spend the evening like this. But in reality, not quite

That’s my reality; sometimes it makes me very sad that that is how I’ve ended up by it’s me, the sum of all my experiences and adventures. I’m also her, but she only exists for a tiny amount of my time.

And it’s not a moan about people online; the glamorous side is the one that Social Media allows me to show, and the only one people who don’t know me in real life see. The problem really is the expectation from the visual stuff, and that’s a problem everyone is going to have to address over the years.

Pictured – case in point, I’d love to have this as my work avatar but the questions would be endless

I know, long answer that skirted around the issue, so &tl;dr no but I wish with all my heart I could.


At last, a safe question with no hidden pitfalls or minefields. No, it isn’t (and I can hear the shock through the keyboard). I buy a lot of outfits, yes, but I will wear them normally at most for two sessions. There’s so much beautiful clothing out there I want to try, and as I said there’s so little time to do it, that I don’t tend to keep dresses unless they really mean something to me.

Pictured – yeah, this is a permanent resident of my closet. I *adore* this dress more than words can say

I have a couple that I absolutely adore and have learnt, painfully due to the inevitable purges I did, how hard it is to find a dress you loved that you have got rid of. So I do a couple of sessions with each outfit and if it really rings my bells then it get to stay in the closet.

Amusingly I have a single closet, about five feet across. I have one hanger that has three identical sets of black male jeans on it, I have a box which has four identical jumpers and three identical t-shirts, and a set of drawers containing identical black y-fronts and three types of socks (all identical), different densities for different times of year. And that is the complete total of my male clothing; I actually don’t own a coat at all (I don’t mind getting wet, all my clothes are black).

Pictured – younger me had a jacket just like this in the 80s and I love that he would have been appalled that a middle-aged woman was wearing one very similar. How times have changed

Her stuff in the closet is another matter. Even though I leave dresses for others to enjoy, or give them away, I still have thirty or so different dresses hanging up next to the sole hanger for men’s trousers. It’s a lovely representation of the sharing bias of a man and a woman to be honest.

Let’s take right now (Thursday 10th March) as an example; I have four new Collectif clothing dresses ready to try, a brand new (came yesterday) posh Bombshell HQ dress (quite expensive) with matching heels (black and white polkadots on both), three stereotypical 1950’s housewife dresses (with two petticoats stored above), three brand new slinky nightclub dresses, my hotel-maid uniform (size 14, the fourth one I’ve bought of that style because it’s adorable), and then my favourites; three Vivien of Holloway (one kitty, one sun-dress, one halter neck), my halterneck ‘pride’ dress (the one with all the hearts on in different colours), a leather jacket, a denim jacket, a blouse/trousers/jacket suit (for work, cough) and two swimsuits.

Pictured – *this* Pride dress. I’m so hoping one day I get to go to a Pride like this, with all my heart

So no, not a huge closet but a very feminine one with oodles of nice stuff. And his trousers on one lonely hanger.


It’s an odd question but I’ve been asked this a lot, often after I’ve been asked where I go. And yes, I have had a lot of makeovers. A ridiculously large number. And there’s no reason to justify it, to myself or anyone else, but…..

I’m 53 year’s old in a couple of weeks. I’ve been working at pretty much the top of my industry for thirty years. I have no children. I have no hobbies to talk about (other than excessive exercise and computer games. And reading a LOT), I don’t do holidays (I haven’t been on a ‘holiday’ for ten years. I have a nice car that I bought seven years ago (it has appeared in some of my photos) and I will drive it until I can’t. I have no family other than my other half. Sarah is literally the only thing I do that gives me pleasure and keeps me sane.

Pictured – well, ‘kinda’ sane

I’ve tried to cut down on the sessions; not because of the money but because my brain works like that. Too much enjoyment dilutes the experience. It has to be like a fine wine or a fine cheese, something I can look forward to, something I can savour, something to work towards. There was a point where I was doing it once a month and that was just too much because, perversely, it needs to be the diamond in my life and to be that it needs to scarce, as much as I want to be doing it every waking moment. That scarcity is what makes every moment in a dress, every moment in heels, every moment looking into the mirror and seeing my eyelashes move, seeing the red around my mouth, the earrings on my ears, such an almost orgasmic moment of pleasure.

But like all people I will overdo it, and have. Hence the massive number. But on the other side of the coin I am acutely aware that I am getting older and there will come a time when the transformation won’t be as good as I want; when my eyes are just too creased to hide under foundation. When my hands, which already are the first place to look to show my real age, don’t match the skimpy nightclub dress I’m wearing. And I’m not terrified of that moment; I know it’s inevitable, and I know I’ll still be able to dress as the ‘older woman’ without caring, but knowing its finite makes it infinitely more precious.

Pictured – and yes, I am aware that I have had a thing for dressing as an older woman in the past. Call it delightful practise

Which is why I am enjoying it now while I can. You have to remember I came to this late; not the urges, not the feeling of being not-quite-a-boy, but the ability to be transformed and, dare I say it, look like a woman. It’s only been five years at most; for forty-seven years I dressed occasionally and in my own house. These are the salad days and knowing they will end doesn’t make me sad, it just makes me more determined to do all the things I want to do now.

Anyway, I seem to be steering into ‘hand on heart, tears on face’ territory so I’ll bring it back to reality. I love what I do. I no longer feel guilty about what I do. And I do it a lot because I love doing it.

So, as I said; if you have a burning question on ANYTHING drop it in the comments.

Stay beautiful and stay true to whatever course brings you the most joy; it’s a crap world right now and any little candle of love should be cherished, regardless of how others see it.

Pictured – ask me anything, darling……

12 thoughts on “[Fun] IFAQ on Sarah Stuff

      1. OK thanks for that small snippet of information, can you tell me if the partner is male or female and if they approve, tolerate or disapprove of your crossdressing? And what if any consessions you make.
        So keen to find out how others live with this obsession.
        Thanks Sally xx


      2. Female, aware but doesn’t want to discuss it. It’s a sexless arrangement though, we’re both pragmatists. She’s my soulmate, but not a physical mate if that makes sense.


  1. Two blogs in one week?! 😮 You are truly spoiling us Sarah! 😁😉 XXX
    But I liked your honesty in this. I can imagine the number of requests and questions you receive everyday. 😕
    Perhaps you should use a quote from a popular 60’s TV series? 🤔
    “Questions are a burden to others. Answers a prison for one’s self.”
    We are who we are and that’s it. We have enough problems questioning our gender AND our sexuality that trying to explain it to others seems hopeless. 😕

    And congratulations on your continued weight loss too. That is quite an amazing achievement! 😘 XXX
    I’ve lost a bit of weight but I’m still quite a way behind you sweetie! 😘

    Stay safe and well my dearest friend. 😘 💋 ❤️


    Liked by 1 person

  2. That was quite entertaining since I do want to get to know you better and become as real friends as we can be via the net. I do love your pictures and yes I do have fantasies about you. Well I wish you a good day.

    Liked by 1 person

  3. Any chance you’d ever create more risque content? Something along the lines of an onlyfans or manyvids? I’d love to be a subscriber! You are beautiful.

    Liked by 1 person

  4. This was a fascinating insight into your world and sums up much of what you have written on here in the past.

    Forgive my forwardness, but have you ever looked into autism or other neuro-divergence diagnoses? Or, alternatively, have you never felt the need because it literally would make no difference? Or, alternatively, should I retract the questions because how very dare I? I’m happy with any or no response.

    BTW, to me, a forty-something father or three in (at the moment) reasonable gainful employment: you are reasonably rich. Make of that what you will, I say it without judgement (positive or negative) of any kind. 🙂

    Also, taking opportunities whislt one can: is there a better life lesson to teach?

    Thank you for your post and apologies for being so slow on the uptake in reading it.

    Liked by 1 person

    1. Hiya Joanna. I have had Complex PTSD for 25 years which has a massive effect on my mental health (basically I have constant fight or flight reflex countered by OCD/obsessive behaviour). Makes life interesting. xx


      1. Ah yes, I remember reading about that in one of your previous posts. Thank you for taking the time to respond, it is appreciated. 🙂

        As long as life is interesting it is there to be lived, I suppose!

        Liked by 1 person

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