[Advice] The Tale of the Telling. Or, what on earth to do when you get caught….

Thought about writing this one for a while but constantly kept telling myself no, readers of this blog want gushes of fashion or odd British takes on the mild absurdity of being a cross-dresser. Not that it’s absurd, it’s more the society we live in that’s absurd, but that’s by the by. This is a NEW type of blog entry where I share my sometimes painful experience with dealing with some of the issues some of us face.

And this one is a doozy.

If you follow this blog you’ll be aware that my partner is aware of Sarah. Well, that’s not strictly true – as with all passive aggressive relationships I kinda downplayed how important Sarah was to me when the (accidental) big reveal happened, and my partner has no idea I’m even called Sarah. I shamed myself slightly by saying I didn’t have a femm name. Yeah, testosterone fuelled defensiveness combined with the soul of a coward made me downplay the femm side of myself. My partner knows I do it, I claim it’s to deal with stress and PTSD which is is, kinda, but way more than that.


Pictured – Stress 😉

But that last paragraph in and of itself explains why I felt I had to share this blog post. A lot of us spend out lives terrified of sharing our secret, driven by old-school moralities and fictitious failings of being ‘less of a man’. I’m lucky, if that’s the right word, in having experience nigh on all the scenarios of telling and not telling, so this will be a quick and tongue-in-cheek guide to something that is definitely not tongue-in-cheek.

I managed to go through five different ways of revealing my inner girl, each of them a completely separate exercise in pain and stress. But first, let’s lay the foundation for those of you who haven’t suffered through the 300k worth of random words and musings so far in this blog.

Oh, and before I start, a quick hello to the German readers of this blog. In my previous life I was involved with a part of the Government that was all about finding info so I can see when people are talking about my blog wherever it happens, and I found a lovely reference to this blog on a German CD site where they were faintly amused at my quote about crossdressing being a ‘little’ thing ‘in the same way World War II was a bit of bother’. For some reason the German readers thought that was quintessentially English. Which it was. 🙂


Pictured – Entschuldigung, britisch zu sein!

Anyway, for someone who claims to be completely unique and independent my origin story was startlingly normal when compared to fellow sisters. A yearning at a young age, satisfied by secretive and surreptitious dressing, a long period of purge/binge, eventual partial reveal due to sloppiness combined with a subconscious desire to be revealed.

Or so I thought. Turns out in my muddled, heading-for-the-grave middle aged mind I’d actually forgotten a couple of reveals, frankly embarrassing, that happened earlier on in my dappled career as the George Smiley of CrossDressers.

Scenario 1 – the unintentional reveal to someone who doesn’t have your best interests at heart

During the late 80s when I was at sixth form (yeah, an archaic term that reveal my age), I was seriously in the shadow-cross-dressing leagues. I had a single carrier bag, pushed deep into the adolescent clutter at the back of my closet in a tiny room in my parent’s house, that contained my booty. All items I’d borrowed/purchased with no understanding of the nuances of female dressing. A red lipstick from the Co-Op, a 1950s girdle found in the attic, a terrible Blonde joke-wig bought at a Joke Shop of all places, a pair of white heeled sandals thrown out by my mother and retrieved after dark from a bin, a pair of clip-on earrings (Edelweiss flowers) taken from my mother’s jewellery box, unbeknownst to me missed by her, and a single solitary flowery dress from one of the prominent 1980s fashion chains (it escapes me which one, the one that did all the Princess Diana style floral big-shoulder frocks that I still crave to this day).


Pictured – like that. Oh yeah, Laura Ashley was the shop…

I would pull that battered carrier bag out whenever everyone else in the house went out, or late at night, lock myself in the bathroom, apply lipstick, button up the dress, pull on the terrible wig and stare at myself in the mirror, unsure of what I was looking for but feeling that delicious warm rush of femininity/naughtiness that kept be going back for more.

To be honest it was a phase of experimentation and for a lot of time that carrier bag was forgotten. In fact, when I went to college a *long* way from home I’d forgotten the bag, tucked away behind a ton of Lego and Amstrad CPC464 game cases.

Well, turns out my mother had some reason, none that i can think of, to snoop around in my closet while I was away at college. This is back in the days of phonecards – for those born after 1990 (and as such I am terribly envious of you) these were prepaid credit style cards you used in British phones to make calls. My parents had provided me with one that I would use every second day, after 18:00 of course for cheap calls, to phone home and tell them I was alive.

So the first ever sharing of my cross-dressing was a terse conversation with my mother from a pay-phone in Middlesbrough in the rain as she asked me if I was gay.

Straight out. No warning. No hint of understanding. A blunt question from a frankly blunt person.


Pictured – Gay? Moi?

I remember feeling cold, terribly cold, that horrible sensation when adrenaline dumps into your veins. After five minutes of what was probably the worst conversation of my life to date it was decided that my father wouldn’t be told. The implication was my mother would hold it over me for years to come, especially because of the earrings which oddly enough meant more to her than the tortured sexuality of her son. But that’s how it goes, I guess.

That experience was so bad for me that I literally blanked it from my mind. It took twenty years before it cropped up in my memory, and I still have a sense of shame and anger towards my mother. Yeah, it was my issue but she could have been a little less like a psychological torturer and more like a human being, Or maybe not.

So that was the worst. So far. Because it was the first.

Scenario 2 – the reveal to someone of a similar mind. Who actually isn’t of a similar mind.

Again, if you’ve read the blogs so far you’ll know that my first relationship was a wonderful 17 year partnership that turned to crap when we got married. After 17 years. Turns out we were meant to be friends (*cough*, asexual, *cough*) but were too young to realise. So, when we hit it off, again at college, 1990, it was all new to us.

I was acutely aware of my urges, and in a bad place because of the threat hanging over my from my mother, so sharing the thoughts of cross-dressing with what was my first real relationship didn’t cross my mind. However, whilst I was a virgin and a tad naive, she wasn’t. And she already had a gloriously wide set of fetishes and fantasies that she just needed a willing partner (again, *cough*, slave) to have fun with.

Amusingly she was the one that brokered the idea of cross-dressing to me one night, leaving me to act shocked (I’m a good liar) yet mildly interested. Her suggestion was swapping roles for a night of fun, including full make-up and the likes (and it was the late 80s, very early nineties, so make-up was fun). Cue a night of role-reversals, a bit of forced BDSM, the usual stuff students get up to when there’s no adult figures to stop them.


Pictured – how Sarah wanted me to look as a student

She was fine with it because she thought she had started it. In fact, when we split 17 odd years later and I revealed to her that I’d been a cross-dresser since I was six she was actually offended. Turns out that was lying to her (which it was) and even though we were in the throws of separating due to her infidelity it was my fault for hiding the cross-dressing.

Ahh, wait a minute, just got it. She was displacing blame, right?

Anyway, the point of this one was this was the dream of many cross-dressers – to find a partner who not only embraced the lifestyle but actively wanted it. It would have been perfect if I hadn’t felt so guilty about the situation with my mother, but that’s just me.

Scenario 3 – outing from a friend in the worst possible way

This one almost doesn’t count because I didn’t admit to my inner-girl, but the situation was excruciatingly embarrassing and to this day I don’t know why the person in question did it.

A bit of backstory on this one – in 1993 I was ‘working in Germany’, which was a cover story for some work I was doing with the Americans in a disputed region in Europe that will remain nameless (ethnic cleansing, go look it up). I was based in Darmstadt, a city near Frankfurt with a huge US base at the time. When I wasn’t at the place that will remain nameless I was loose in the town, or in Frankfurt, with a lot of spending money and a lot of loneliness.

Now Germany in 1993, before the Internet really took off, was a disconnected place to be if you didn’t speak the language. So I let the British squaddies and the US soldiers guide me around the places. Best bars for beer, best places for, err, friendship and, given I came from the backwaters of England a truly eye-opening experience, the best Porn shops in the world.

Back then Sex Shops in Germany were a wonder to see. No real censorship of videos (yes, yes, it was before DVD and the luxury of XHamster where you can see literally anything now at a single click) or magazine. So I bought some of the usual smut when I was with the others, and then came back by myself to buy some of the trans-stuff.


Pictured – and every model in those mags dressed like this, oddly enough

In my defence I was lonely and before the Internet there wasn’t much to do on base other than avoid adhoc football/baseball games or just exercise. So I built a little stash of the best cross-dresser porn I could, very safely secured.

Come the end of the tour and I headed back to England – I was in a flat with my first partner at the time, who knew of all this from college.

Thing is, I had to get my stash back through customs. So I hid it in a box with some hardware (Satellite dish – I worked in comms and rigged up a SKY dish that SKY thought was bolted to the side of a flat in Bristol but was actually mostly leant up against the side of a tank….. ahh, the good old days).

And I was so excited at coming home to somewhere where there weren’t bullets that I clean forgot about it.

Fast forward a couple of month – I had a new job working at a computer firm in Bristol and had struck up a friendship with a co-worker there, a girl about my age who had the same interests in sci-fi. Purely platonic, but I felt for her because she was starting off in her career and wasn’t getting paid the same as her male colleagues.

She’d got herself a new flat and was looking for a cheap way to get satellite.

Can you see where this going?

Stupidly I gave her the box that had the receiver box, the dish, and a healthy selection of transvestite contact and porn magazine.

Now this is where the tale gets a little more embarrassing. Rather than take me aside privately and chat about it (no good deed goes unpunished and all that) she waited until a drinking session with the others from work to spring it on me in the middle of a drunken conversation.

Imagine that if you can. You’re chatting with people in a pub when the girl just blurts out ‘By the way, did you realise your tranny porn was in the box you gave me?”.

Remember when I said the first one was the worst? Well, we have a new winner.

Again with the rush of adrenaline and, to be honest, a couple of months of a seriously bad feeling in the pit of my stomach. I managed to fob it off – I think quickly when I’m in that level of embarrassment – and came up with an excuse about bringing other people’s porn through customs in my kit to avoid them getting caught. It was met with laughter and smiles but secretly I thought ‘why would you do that?’.

Scenario 4 – when your other half finds out and you didn’t intend her to

And now the biggie. My other half found out about my tendencies, which were very, very well hidden, in the most ironic way. For the *first* time I’d bought myself a dress off of Amazon and forgot to tick the ‘collect at a box’ option. Maybe it was intentional, maybe I’d got to the point where I wanted someone I loved to know, but either way it was not the best way to do it.

My other half has a business reselling items off of eBay, and she likes packaging. I’m a middle-aged idiot with no self control when I get a parcel from Amazon and I open them like the Tasmanian Devil on steroids, so she had taken to carefully slicing parcels open so I could open them in a way that didn’t destroy the packaging. It was a good system.

Until I bought a polka-dot dress and shipped it to the house by accident. When she slit the envelope it was obvious the contents were a dress. She chose not to tell me she had seen it, thinking it might be a secret present for her (I bought her a lot of cool frocks, partly because I wanted her to look superb and partly because I wanted to at least buy frocks in the period when Sarah was asleep in my mind), but as the weeks went by and she didn’t get given it she started to think I was having an affair.


Pictured – this was the very same frock, and the girl I bought it for

It all came to a head  one night just after Valentine’s day when we were both grouchy, and she threw it in my face that I was buying other women clothes. I threw it back in her face that she was almost right.


To be honest, the conversation we had was cathartic and for the first time ever I felt a release, like I didn’t have to be in the shadows any more. And that was a bad and a good thing.

It gave me more confidence to be Sarah more often, but I’d overlooked the fact that my other half was actually not that OK with it.

The initial realisation that I wasn’t having an affair had been rapidly replaced with the facts that a: I’d lied to her for the whole of our relationship, and b: given my asexuality she read into it that I was ore than a cross-dresser, that I wanted to transition, and that she would lose me, perhaps even to a man.

It was a horrible situation to be in – I’d been partially blinded by thinking that everything was fine, but in reality it was a huge ask for her to take it onboard. So we had some rocky times, not helped by a lack of intimacy.

Since then it’s got better. Not perfect, but better. I don’t feel guilty anymore *but* I don’t feel as free as I did that day when it first came out.

Scenario 5 – when you actively reveal yourself to a friend. And it goes horribly wrong

So, after all those ‘entertaining’ reveals and in a position of my other half knowing and having told her best friend and her therapist which was, hmm, not part of the plan, I was feeling like I needed to tell someone *cleanly* for a change. No sneakiness, just come out with it and finger’s crossed they’d be fine with it.

So I decided to tell my oldest and best friend. A guy who knows me completely. Well, aprt from the Sarah side at least. A guy who has rescued me from the arms of a prostitute, a guy who let me be his drunken best man, a guy that I’ve been pant-wettingly drunk with since 1986.

What could go wrong?

Well actually, not what you think. I set it up perfectly, told him I needed to chat and had something serious to tell him. I told him to me meet me in my hotel room before we went for a beer (and no, I wasn’t enfemme, not that brave). What I did do was to have my laptop open on the desk in the hotel room with what I thought was my best picture up on the desktop.

So he arrived, saw the laptop, saw the picture…..and totally ignored it. We talked about the usual stuff, all the while while my heart was beating erratically and I was trying to find a way to drop it into conversation.

Now this is someone who knows my background, knows my career. He’s seen me punch and break tiles in pub bathrooms drunkenly. We’ve lusted after the same women at school. For me to reveal the femm side to him was a huge, huge leap, and i couldn’t find a way to do it.

So I kinda chickened out a bit. I asked him what he thought of the picture.

His first response was ‘it’s a picture of Katy Perry, so what?’.


Pictured – *not* Katy Perry

I said ‘Look again dude. It’s me.’


Bless him – he didn’t go ballistic, he didn’t say anything crass. It was just a case of ‘wow’. No questions as to why, just some lovely comments along the line of ‘no way dude, she’s beautiful.’ and the like.

Cue an evening of odd but very entertaining conversation, along with me showing him all of the pictures I had of Sarah up until that point.

It went brilliantly. And then I had to go and spoil it.

See, my friend is somewhat of a lady’s man and a lot of his comments, and mine because I always treat Sarah as someone I’d like to know intimately,  seemed to cross a line. It was as if he had compartmented Sarah off as a different person, someone he could express a liking for without actually dealing with me.

And I fed into that. In a moment of rash silliness I suggested he should come to London when I was doing the next session with Cindy and maybe we could go out, to the Wayout of all places. He could meet Sarah.

I knew this was a bad idea but I was so taken with him knowing, and him being so open and accepting about it, that it just seemed like the best of bad ideas.

So, fast-forward a couple of weeks and we’re in a hotel room a couple of hours before I had to go over to Cindy’s for the makeover for the Wayout. I’m shaving my ridiculously coarse and werewolf like stubble, and we’re talking, excitedly, about the evening.

He is looking forward to meeting Sarah, and I should have clocked the problem there and then. He still didn’t match her with me.

So I went to Cindy’s, got dolled up in serious retro makeup and a beautiful flowing polkadot frock, topped off with a Betty Page wig, shoes I couldn’t walk in, and two bottles of red wine.

Yeah, two bottles. I was terrified. Partly because I was revealing myself to someone I trusted and, yes, loved, but mostly because I was just genuinely scared. The same cold feeling pumping through my veins I’d had with most of the other reveals.

He was meeting us at the club, so I made my way over with Cindy and Vicky (her partner). He was stood outside and his eyes lit up when I walked towards him, careful to keep my pace as feminine as possible.

He took my hand  and said ‘Hello Sarah, you look beautiful.”

And I said “Thanks Dude” in my most manly voice.


Pictured – perhaps *not* the most subtle of outfits for a ‘first date’

Bang. Moment broken.

Anyway, rest of the evening went fine. I drank too much and suggested a kiss which he gently refused and i’ve barely talked to him since because I’m genuinely ashamed. Perfect ending 😉

So, just what was the point of this blog post then?

Advice. Everyone is different. Everyone’s situation is different, and there’s no golden-ticket to telling the ones you love and respect about the other you. But there are some simple rules you can stick to.

If you never intend to tell your other half be very, very careful. Always have ‘plausible deniability’ on everything you do for the femm side of you. You need to have a plausible reason as to why you bought that perfume, why you were away overnight. Something that is believable. I got sloppy because I think I wanted to tell my other half, and in doing so it was probably the worst way to tell her.

If you intend to tell your other half/friends, do it *right*. I know, a pithy statement, but you need to put aside what you want to get out of it when you decide to do it. The person you tell will be shocked – for most of us long-term cross-dressers hiding becomes a part of life and we are very good at it. Be gentle, be understanding. Don’t be defensive. I made the mistake of assuming the shock my other half got was instantly dispelled when I came clean, but it can be a long process.

But from the other side, if you need to tell you also need to think of yourself. Don’t feel guilty afterwards, don’t autopsy what you said or what you did.

If you asked me whether it is a good thing or a bad thing to reveal, I’d have to say both. From my personal perspective it’s wonderful to be able to buy what I want when I want, to indulge in Sarah time when the whim takes me, but also, perversely, I feel I’ve lost something. Perhaps my best friend, but also Sarah was mine and mine alone. And now she isn’t. It’s a different dynamic and to be honest I’m still, two years after partially coming out from behind the pink curtains, unsure as to whether it was a good or a bad thing. That could be down to the fact that I’ve had the worst, and the best, of experiences revealing.

At the end of the day do what makes you happy, as it’s your face you have to see every day in the morning, made-up or not.

Stay beautiful and thanks for sticking with this long one until the end…..


6 thoughts on “[Advice] The Tale of the Telling. Or, what on earth to do when you get caught….

  1. Interesting and honest blog.Revealing is very risky even with todays attitudes.You never know the reactions,and uf it does not got as well as expected it cannot be untold.But if it does go well you wish you had revealed earlier.A real life conundrum.Love reading your blogs.

    Liked by 1 person

  2. A very frank and intensely introspective post Sarah. And also, a very important one. You know I’ve been wrestling with these decisions for years and still haven’t said anything. The coward in me is too strong but also I would like to think that the caring part of me can’t bare to hurt the person they love. Thank you for writing this.

    Liked by 1 person

  3. Sarah, thank you for this, something that many will find familiar and some will find valuable. And of course it gave me a chuckle too. I’ve had a mixed bag of coming out too so I can empathise.
    And now for the BIG compliment part from a like minded spirit – your style and looks are awesome, and you combine glamour and wit in all of your photos. You can stop cringing now, compliment over.
    Faye x


  4. Sarah,
    As ever, a brilliantly written, witty article about the situation a lot of us find ourselves in. You are both a literary and a transformation genius . I know you use a service, but it’s your styling, wit and personalities (yes plural) that shine through. Keep up the good work.
    Every try touting Sarah’s voyage as a TV sitcom (pun intended)

    Debbie xx

    Liked by 1 person

  5. I’m ashamed to say (well almost) that my adventures as a trannie began by ‘rescuing’ clothes from washing lines. In my defence, I didn’t have a sister to borrow from and my compulsion needed to be satiated somehow.

    The most embarrassing moment in my life came in the summer of ’59 when I was 14 years old.

    One evening, I noticed a couple petticoats and other underwear in the back garden of a neighbour about 5 doors up and I was determined to have them. Later, as I was trying to remove the pegs, the lady of the house came flying out of her back door, grabbed hold of me and dragged me into her kitchen, screaming obscenities and hitting me with her bare hands. She was very angry – quite rightly, I guess. Anyway, she eventually calmed down a little, threw me out and said she was going to tell my parents. I was absolutely terrified, shaking from head to foot.

    Well, I was in total terror for a few days! Soon after, as I came home from school, the neighbour was talking to my step mum over our garden gate. As I approached them, I began to feel hot and sweaty. Then everything went kind of misty and the world started spinning. For the first and only time in my life, I feinted. When I came to, they had me sitting on a chair with my head down between my legs and they were telling me to take deep breaths. After I had recovered, I went back indoors with my step mum. It seemed obvious that the neighbour hadn’t told her – not yet, anyway – so I breathed a huge sigh of relief! I don’t know why, but she never did tell. Possibly out of embarrassment?

    Suffice to say – my life of crime stopped (more or less) as soon as I could afford to buy my own things.

    Liked by 1 person

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