[Philosophy] Re-frequently Asked Sex-tions

I’ve been doing this blog for a while now (it’s been so much fun I don’t even remember how long) and as part of revealing Sarah to the world I’ve been developing what the kids today called a ‘Social Network Presence’. Which means she has an FB, Twitter and other accounts, which is always amusing when drab FB gets a ‘people you may know’ request with a photo of her on it. Normally when I’m surfing my drab FB at work.

I talk to a lot of people online, T-Girls and admirers (although never GGs for some reason), and I often get asked the same questions – it feels like Social Networking, which isn’t the most subtle of mediums, forces the same simple queries. A lot of them are vanilla, but some tend to escalate into the sexual side of things. Which is what the little FAQ blog is going to be about.


But not answers as such, because I tend to answer the same way to the same questions. This blog is about *why* I answer the way I do. It may be a little close to the bone because I’ve changed a lot over the last couple of months – my heavily cemented walls of denial I have had in my head for decades have been eroded by having to ask myself in all honesty the questions that others ask.

But don’t worry – it’s not going to be a runny-mascara, ‘oh the pain’ kind of blog. This one will be frank and honest. In fact, I’ll let the reins off of her and let her have her say for a change, no drab-filter, no humour-filter. so strap yourself on, I mean *in*, and let’s get started……

Oh, and although this is tagged with [Philosophy] it’s not really safe for work.

1: Do you go out often?

Subtle translation – “Are you up for meeting?”.

The frank answer is no. It doesn’t come across in the photos but I’m *huge* and painfully shy. But more importantly I cannot do my own makeup. Never been able to, but I’ve been more than lucky in finding beyond-excellent makeup and style artistes. Unfortunately these artistes all live an average of 300 miles away from where I call my home, which means that I have to plan in advance to be Sarah.

And something else – for twenty or so years I worked in ‘security’, which translates to initially being in the armed forces. I’ve been forty yards from large explosions (tip – if you suffer from headaches due to sinus issues standing very close to an exploding device is perfect for curing it, something about the pressure wave is really good for blocked sinuses. As long as the shrapnel doesn’t take you out), I’ve been in riots, I’ve been in serious situations. Yet I’ve never felt the terror I feel when stepping out into the outside world in heels and a frock.


I know, daft right? A lovely friend said to me recently ‘it’s only wearing women’s clothes’, but it’s not quite that simple. When I change I change at a root level. Even copious amounts of alcohol doesn’t take off the edge of fear from being unable to stand up for myself. Not through weakness, but because when I am Sarah I am Sarah, delicate, vulnerable. A woman in a harsh man’s world.

What people who haven’t been out don’t really understand is that you see the world a different way. When I’m in drab my clothes are a shield, a comfortable facade from behind which I can glare at the world, deflecting attention. Part of the experience of dressing, of embracing on all levels the style and personality of Sarah, is the shedding of that shield. The makeup, the feminine attire, it doesn’t provide a shield. In fact it advertises ‘look at me’, and that’s a situation I’ve never known in drab.

That’s not to say I won’t go out. I’m planning a session in about a month where we (well, Cindy) will craft a passable makeup look, cutting back on the glamorous and going for ‘tall woman’. It will be……. interesting. Part of Sarah’s appeal to me is her stylised femininity and I’m worried that blanding it down to make it acceptable to the real world will either lose something or I’ll just look like me in a frock.

Of course that’s not the case, and when I see myself as a day-to-day girl the intention, if I can swallow the terror, is to go out into the outside world, sans alcohol, and see what happens then. Best case scenario is that it will be thrilling and comfortable, a discovery of a new facet of Sarah. Worst case scenario….. there are pubs close to the makeover studio. Pretty sure I can Dutch-Courage it pretty quickly.

When I was growing up my parents used to send me to stay at my grandmother’s for most Saturday nights. This would be when I was about nine or so, and I used to sneak a wig I had found, a tube of lipstick and a pair of white strappy sandals I had pinched from the loft in a bag as part of my overnight stuff. When the rest of the house had gone to sleep I’d sneak into the spare bedroom where my grandmother kept her spare clothes, a lot of 1970s ‘sensible’ clothes. I’d walk very, very quietly and carefully, my heart in my mouth, clicking the door of the wardrobe open without breathing, taking one of the three or so frocks that just called out to me, then sneaking downstairs (I used to sleep on the sofa in the living room). On would go the dress, gently pulling the zip which sounded unfeasibly loud on the post-midnight quiet, always dressing in the dark. Then the wig, a 1960s style short bob. Then a generous application of lipstick – I used to almost destroy my lips rubbing it off afterwards – then the sandals. Then the long, slow walk to the back door, dreading the sound of the heels on the hard kitchen floor.

When I reached the door I’d turn the key as slowly and as quietly as i could, knowing that if I made just too much sound the lights would come on and I’d be caught, stood there in a dress and heels, lipstick, wig, and die of embarrassment.

Forty years later I can still taste the thrill, the fear, as the door would click open, terribly loudly. And then the moment when I pulled the door open, and would stand in the doorway, feeling the cold air blowing in across my bare legs and deliciously up the dress.

And I would stand there, finely balanced between the yearning to close the door, strip off and head back to my blanket and pillow, heart thumping in my chest like a rabbit’s, and taking that first, infinitely long step over the door frame, carefully putting the heel down in order to avoid the click, then stepping out over the threshold.


The fear I felt then, my legs trembling and tight, a combination of the four inch heel and the adrenaline pumping through my muscles, is exactly the fear I now feel when considering stepping out into London fully enfemme. It’s identical, a behaviour programmed into a nine year old’s responses by serious spikes in emotion. It’s a lovely fear, almost fetishistic. But It’s still fear.

So, in answer to the question, no – I don’t get to go out often.

2: Do you get aroused when you are dressed?

Interesting one this. Back at the beginning dressing used to be a a massive turn-on. I’ve mentioned in a previous blog post about the incident where I had my first, you know, ‘expulsion’ while dressed without knowing what it was. Which led to a terrible couple of hours a: worried about what the hell just happened to my undercarriage and b: how the hell to clean the stain out of one of my mother’s favourite day dresses. So I had it pretty much programmed into me – wrap myself in women’s clothing, be unable to stand up for a while.

But since Sarah has re-emerged it has changed massively. Perhaps it’s desensitisation to the whole thing (yeah, too much bangedtranny.com, xhamster and tubegalore 😉 ), but I think it’s because Sarah is more me now. Since I started going to Cindy’s I’ve *never* got aroused during the makeovers, which is a good thing because everything is tucked, pushed and compressed back between my legs. Getting aroused would be comparable to water-boarding in terms of torture.


It’s not to say I don’t find the product erotic. Far from it, many a fun evening imagining having sex with Sarah from both sides (read into that what you want, dearest reader). But when dressed it’s more of a warm feeling, standing in front of the full length mirror blowing kisses to myself, trying out different positions for the overly long stilts that some could call my legs.

We’re all different. Some T-girls get immensely turned on by the dressing process, by being dressed. For me the brain seems to have shifted to being Sarah when dressed, and the customary bulge down there would interfere with Sarah’s time. So it gets literally turned off.

For a while that worried me. I thought the thrill had gone, that I had somewhat grown out of the fun of being dressed, but that’s not it. I still get the warm rush inside, that feeling of utter and beautiful emasculation. In fact it’s more than sexual now (sigh, starting to sound like feckin Sting), it’s a full body thing that doesn’t need the animalistic swelling.

However, the shift to being turned on by the product as opposed to the process does have it’s downsides. I can’t wait to see the pictures, even though the journey from London to home involves hanging around Euston, couple of hours on a Virgin West Coast train then ninety minutes of country roads, so I tend to say ‘stuff it’ and open up Sarah’s MacBook on the train, scanning the pictures while Virgin employees wander by.

Thing is, I’m tall (I may have mentioned this). The Virgin Pendolinos are designed around the average British person, which means I am a foot too big for the seats. And the tables are fixed in place. Turns out if I get mildly aroused I can end up uncomfortably pinned under the table, which then involves carefully noting when my station is coming up and closing her laptop twenty minutes earlier, thinking unsexy thoughts in order to not appear odd when leaving the train and walking to the car.


Long story short, you won’t see a bulge in Sarah’s frocks.

3: Do you want to be my girlfriend? My whore? My friend-with-benefits?

Ahh, the naked pink elephant in the room. They say honesty is the best policy, so here we go.

I haven’t had sex in over eight years, Not because I can’t but because I’m in a monogamous heterosexual (we’ll get back to that later) relationship with someone who no longer can have sex. I’ve always been loyal my entire life, so I wouldn’t betray her with another woman.

Sarah though is a different matter.

I grew up in the 70s and 80s, a time (at least in the early 80s) when homosexuality was frowned upon – twenty years earlier it was illegal and a lot of the older people of that generation just didn’t have the capability to understand or tolerate it. So it gets drilled into you that same-sex relationships were bad, were wrong.

It’s called a meme for all you science fans – a behaviour that is enforced by culture and other people as opposed to your own genes.

When you grow up in a hyper-masculine environment (school, college) where homosexuals are ridiculed as opposed to understood, it gets gently beaten into you that it is wrong.

Fast forward to now, and ignoring the cultural degeneration that is happening over the pond due to Trump, we live in a different time. It’s finally dawning on the majority that pleasure isn’t sin, that some people are turned on by different combinations. Some men love t-girls because of the juxtaposition of  hyper-feminity with biological masculinity. Some t-girls love the attention of men because it is the ultimate justification, the final tick box that makes them feminine. The whole spectrum of relationships are acceptable with one caveat….

A good friend of mine once said to me something of massive import that I completely loved – “Whatever happens between two consenting adults is completely fine”.

So my quandary is this – in drab I love women, everything about them (yeah, that could include clothing, styling and other obvious Sarah-fetishisms). I have no interest in men. I am one, so I know what goes on in their heads.

Sarah yearns for intimacy as a woman. That could involve a man treating her as a woman. Or another t-girl. But not a GG. To Sarah the boyfriend is the ultimate fashion accessory, a final indication of acceptance of role.

Yes, it’s a fetish. Yes, it occasionally spills over into kinkiness (especially last thing at night on certain Social Media sites).

But again, there are caveats. I’ve never been intimate with a man. Never been kissed. Hell, I’ve only kissed four women in my life, not counting family. So a lot of this could be unresolved homosexuality from childhood, the fact I’ve been a bloody Monk for eight years, the fact that you can’t physically dress repeatedly the way Sarah dresses without wanting something more.

So it becomes a balancing act between catholic-ish guilt, hard-wired childhood of being around homophobic people (most of which were closeted as I found out later to my amazement) and deep urges to *be* a woman in all respects.

Am I horny? Holy blue-balls, Batman, of course I am. Would I do it if dressed as Sarah and the opportunity arose? Almost certainly.

So how does this tie in with my heterosexual monogamy? It doesn’t. Telling myself I’m Sarah whenever I get the urges doesn’t change the fact that I’m not a woman. We have enough labels now for anyone to call themselves anything while still maintaining a modicum of denial – heteroflexible, bi-t-sexual, the list is endless. So as part of even considering intimacy as Sarah I need to be honest with myself.

And I’d like to think that I’d be fine with it. Sometimes it’s lovely to live in the 201x’s. Having spent a number of years in the 70s and 80s being called a poofter and reacting angrily to it left an unnecessary scar. I’m not heterosexual, I’m not homosexual. I’m *me*, and that’s something I should celebrate.

To answer the original question I’ll pass it over to Sarah.


“Yes, if you were gentle, understanding, my friend as well as being physical intimate. As long as you agree that anything that happens between two consenting adults is absolutely fine, isn’t sinful.”

So, that’s pretty much that for being serious. I promise the next blog post will be only about fashion, squeee-ing about retro and talking about plans for future Sarah outings. Probably….

Stay beautiful and true to yourselves, wherever you end up on the sexual spectrum.



2 thoughts on “[Philosophy] Re-frequently Asked Sex-tions

  1. I love this post sweetie. Your candour and honesty with us, your readers as well as yourself is very refreshing. And I think that many of us need to be more honest with ourselves too.
    More superb insight.

    Liked by 1 person

  2. Hi Sarah. Oh my! Your blog could be me talking about myself! I also am faithful to my lovely wife of 30 years and have also been celibate for about 6 years due to her health problems. I am her sole carer. Mind you, at the age of 75, I’m probably past it anyway (LOL!) As a teenager and into my early 20s, I had no fear of going out in public, usually window shopping in Kingston, even though I did experience a couple of near disasters. Also like you, I am useless at make-up. My previous attempts have always left me looking like the “Bride of Dracula.” However, in those days, most girls used very basic make-up. I just used a bit of foundation, some blusher, some lipstick and a cheap wig – that’s all.

    After my first marriage ended, Sylvia resurrected herself and I joined a group. I still went out in public, but only in the company of other ‘girls.’ During that period, I was lucky to have found a man who took me out occasionally and treated me like a real woman, but after about three months, he began to come on too strong and I had to end our relationship. We would kiss and fondle each other although I wasn’t altogether happy with that, but I allowed it to continue, mainly in gratitude for experiencing the lovely feelings of being a real woman, out with a considerate man.

    Since I met my curent wife, I am ‘allowed’ to be en femme 24/7 unless we have company or have to go out. She doesn’t like me to wear make-up, a wig or high heels because I think she likes to see the vestiges of the man she married, if that makes sense. Also, she thinks I might like to go out in public again if I go the whole hog. She’s wrong, of course, ‘cos I would be terrified to go out as Sylvia these days. So I applaud you for stepping out occasionally. I know what courage it takes and I am in complete awe of you.

    Stay safe Sarah, lots of Love, Sylvia xxx

    Liked by 2 people

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