Operation Terrified

So, I did it. I went out to a trans-nightclub as Sarah, dressed identically to the picture above. And it was utterly terrifying….

I’ll take a step back and start at the beginning.

I’m a planner. Often at the expense of everything else, to be honest. Everything has to be perfect, all bases covered. I call myself a worst-case-scenarioist, which trips off the tongue, but that pretty much covers it.

So, it was all planned. I’d saunter over to the makeover studio for 7:30pm, get dolled up, maybe try a couple of outfits on, have a glass of red wine to calm the nerves, then in a taxi to the club, meet my best friend in the world there, soak up the atmosphere, home to the hotel for 3:30am and all’s well in the world.

Well, it didn’t quite go like that. It was fun, it was an education, and it was utterly petrifyingly scary.

For a start I met my friend in advance and we polished off a bottle of red wine ‘to take the edge off’. By this time I was pacing in the my hotel room, shaving myself completely wrongly (my friend gave me some tips but I was so scared I kinda ignored them and slice, slice, slice, bleed, throb) and getting more and more antsy.

Hopped a Tube from the hotel to the makeover studio and realised that it was very, very hot. A little flustered, a little drunk and a lot terrified I buzzed the bell and was met by the smiling, talented and awfully attractive Cindy, who was to do the makeup, style Sarah and escort me to the club.

First the change into the undergarments. Here’s something most blokes and probably most girls are unaware of – if you are ‘T’ and you want to look shapely you end up wearing a f*ckload of undergarments. I had panties, tights, two pairs of padded hip under-panties and a pair of stay-ups. That’s a lot of layers.

And by the time I had squeezed them all on I needed a pee again. Turns out drinking half a bottle of wine and being stressed and scared makes you pee. A lot. Cue pulling down the five or six constrictive layers and trying to rescue the little firehose.

No urine.

Turns out drinking half a bottle of wine makes you want to pee badly, but many layers of constrictive female undergarments tie tubes shut. I pulled stuff up, stuff down and eventually felt the warm release as my bladder became untied.

Of course twenty minutes later the fear triggered another need to pee and the same humorous battle took place. And this was before I had nails on.

Next I had the makeup done. It was stunning, as always, and this time Cindy used fixatives so I wouldn’t end up looking like a sad, terrified clown in the heat. Then the hair was applied, pinned in with tonnes of fixing points and topped off with a flower. Then the dress, and when the zip was pulled up to the top I felt deliciously constrained, swinging my hips in front of the mirror and looking at the woman staring back at me.

The woman who was about to go out in London. On a Saturday. Around 11:00pm.

Hell, in drab mode I’m normally in bed before ten, giving up caffeine a while back means I have pleasant sleep patterns. Now I was planning to be out and about, in the heat of a summer night, in the busiest city in the country and without my usual shield of grumpiness, black clothing and stubble.

To say I was scared would be an understatement of the same magnitude as saying World War II was ‘a little bit of bother’.

More wine flowed, more humorous imagery of hiking up my skirt and playing ‘find the outlet’ amongst all my tight hosiery in order to pass another couple of pints of liquid. Amazingly I’d drunk probably about a bottle of wine by now and peed about five bottles worth.

I hadn’t got the nails on yet and Cindy has a lovely Ibanez guitar, so I asked, nicely, if I could have a little play to relax myself, and she said it was fine.

When you find yourself sat in a stranger’s flat, wearing a beautiful 50s retro frock, binding underwear, a corset that is displacing your kidneys and liver in new and amusing ways, pristinely made-up to look like a beautiful woman who obviously adores dressing in vintage frocks, banging out ‘Carry on my Wayward Son’ on a guitar and singing along to it you need to ask yourself just how the hell you got there. Sublimely mad moment.

By now time was getting on so it was time for the nails. This is probably the hardest bit for me because I can do absolutely sod all for myself once I have nails on. I love long nails, plus I love the smell of the nail varnish, and the combination of that and the copious wine was giving me a serious buzz.

Nails were done, time was approaching the moment of no return. I slipped a pair of black high heels on, surprised at how comfy they were (spoiler alert, they weren’t comfy by the end of the night. Oh dear Lord, they were not…), Cindy lent me a trendy little handbag with a wrist strap, into which I put a set of banknotes and my two phones – planning you see, one is my drab phone, one is Sarah’s phone – and nothing else. No identification of drab-me. When I went out of the door I would be in the hands of the Gods, entirely Sarah with no way back until the taxi dropped us back at the end of the evening.

My heart was beating fast in what should have been my chest, but due to the very tight corset it could have been beating in my arse for all I knew. I stepped across the threshold of the door, gently, my heels clicking on the steps as the door closed behind me.

I was out. I was Sarah. I was very close to an anxiety attack.


Cindy’s partner drives a good old fashioned London black cab for a living, so we jumped in the back as she got in the front, and we were off.

It’s hard to describe how it feels, sat in the back of a cab speeding through a bustling city at night, your legs crossed in a feminine way, your skirt lying gently over your knees, a hand resting gently on your chin, the long nails tapping your cheek as you watch the city breathe. Every time we stopped at a traffic light, or stopped in traffic, I felt the dark fear come over me. I looked out of the window of the cab and locked eyes with a man walking by. He didn’t even blink, just took in my face and carried on, and it hit me again what I was doing, the enormity of it for me.

This didn’t help the fear.

And then we were outside the club, pulling up to the kerb, the engine of the taxi going quiet. It was busy, there were lots and lots of people, many drunk, walking past. I didn’t want to leave the warm embrace of the back seat of the cab, my legs felt frozen, but I steeled myself, standing daintily, which wasn’t that much of an option given my state of dress, and stepped out into the warm London night, my purse swinging on my arm as I closed the door of the taxi.

And I was there. About a mile or so away from my drab identity, out in the real world, and terrified.

It wasn’t getting any easier either. I could feel eyes on me, I felt uncomfortable, I felt ill at ease. The clicking of my heels as I walked as carefully as I could, slightly cursing my choice of four inch heels which, when combined with my height, made me 6 feet 5 inches of fabulousness, no longer thrilled me but reminded me that I was now a woman. I couldn’t run if anything happened. Hell, I could hardly walk.

We got to the door of the club and my friend was there. He’d seen pictures of Sarah but this was the first time in person, and I instantly almost spoiled it by automatically clicking back into drab character, but I caught myself, flashed him a smile and he smiled back. I introduced him to Cindy and her partner, pleasantries were exchanged, wonderful things were said, and then we headed into the club.

It felt odd. Here was someone I’d known for thirty years, I’d been his best man, we’d been drunk together countless times, done some daft things like all-night World Of Warcraft and Energy Drink sessions. I now I was tottering along on heels, my dress sliding deliciously over my legs as I walked along side him. He’d made an effort as well, wearing a tidy suit, and we made an interesting couple.

A quick reminder of the times we now live in as we were searched at the door of the club, me taking five attempts to open the zip on my handbag with a set of fingernails that alternatively were trying to slice my hand open or catch on everything. My corset set off the metal scanner as the bouncer ran his magic wand up and down my dress, but I wasn’t asked to strip.

Inside the club was a bit of a meat market. Lots of obvious T-prostitutes, loads of admirers, a couple of really stunning T-Girls. I could feel the fear rising again and drab-me, locked inside Sarah’s flat in the middle of my brain, was starting to lose it.

And I did something that I never thought I’d do. I asked my friend to hold my hand.

He was more than happy to do it, and we stood by the bar waiting to be served, hand-in-hand like a couple on a date.

Yeah, that was one of those moments where you really have to ask yourself ‘how the f*ck did I get here?’ 🙂

A couple of glasses of red went down nicely, lots of small talk, someone pinched my arse a couple of times but I let it slip. Given the number of garments back there it must have taken him a huge effort to do it, so kudos to him.

I needed to pee again, badly. I asked Cindy where the loos were, and she pointed to a sign on the far side of the club. For a second I thought about just holding it in, trying to get the body to re-absorb it, because I didn’t want to totter my way through the mass of admirers who were all standing with their backs to the wall, scanning the crowds of stunningly dressed T-Girls for their targets of interest. Even just looking towards the toilet got me three eye contacts, a wink and something mouthed which I fortunately couldn’t read.

So I girded my padded loins and started the walk of shame to get to the toilets, only to have Cindy grab my arm.

“Remember to use the ladies.”

Oh. That hadn’t occurred to me. I just assumed I’d totter into the gents, rummage around in the multiple layers of elastic and silk with my five red blades of death until I found the poor hiding snake and then try to squeeze out urine as quickly as I could.

Oh no, that wasn’t the plan. As far as the club was concerned I was a woman, so it was the ladies.

I’ve never been in a Ladies toilet in my life, even accidentally. It was an experience. For a start there were people talking in there and, as I shuffled carefully into a cubicle after waiting in line, which was both thrilling and a little demeaning, I found myself working at the undergarments in order to sit down, after carefully wiping the seat. Seeing my hand, dark red nails, wiping the seat made me realise just how far down the bloody rabbit hole I’d gone at this point.

So I sat in a ladies toilet in a night club, my dress carefully hiked up, my heels together, listening to some frankly rude conversations going on between a number of T-Girls who were doing their makeup in the mirror and discussing oral sex techniques, trying to get my bladder to empty as fast as possible.

When I write my autobiography that moment will have an entire chapter all to itself. It doesn’t get more surreal than that.

The rest of the evening was somewhat of a blur. I remember lots of wine, some interesting and uncomfortable conversations with my friend as we both tried to work out the dynamic of the situation.

And then my feet started to hurt.

They aren’t kidding when they say heels are hell. I always thought it was just a ‘woman thing’, the same way I always half-heartedly complain about how impossible it is to pass urine in the morning when you have a ‘I’ve just woken up’ erection, but no, they have all the right in the world to complain about it.

The pain was like nothing I’d known. The only thing that came close in my life before was when I had foolishly decided to go snow-boarding and the rigidity of the boots hurt my ankles. But this was something else. There seemed to be no comfortable way to stand. On the plus side the heels made my legs, if I may say so myself, really sexy, but that’s scant comfort when everything below the knee is a throbbing mass of abused nerve endings.

I’d spent a large proportion of the evening sat outside, where there were benches, with my friend, talking deeply about life in general, and Sarah specifically, trying really hard to look like a couple so I wouldn’t get attention.

And that was probably the thing that hit me most. You get frocked up, you get the makeup which advertises you as a woman, the sexiness of the lipstick, the lashes. The curves beneath the dress, the ample bosom, the f*ck-me heels and stockings. And all I wanted to do was blend into the wall. I was terrified of being seen and I literally clung to my friend like he was a life-preserver and I was drowning.

I can’t thank him enough for that. I had the option of disguise, and he was there as himself, so it must have been tough. I was amusingly acting like a scared girl.

Anyway, the hours passed and we hit 3:00am. I hugged my friend and he went off to his hotel, then I tottered very painfully back to the cab with Cindy and her partner. I’ve never been happier to hear the sound of a door shutting as I was when I slid my dress-wrapped bum on to the seat, peeling off my heels and starting to relax for the first time all night as we sped through the early morning back to Cindy’s, singing to Muse on the stereo.

Then it was off with the dress, the blissful release of the corset coming off as my organs shuffled their way sadly back to their normal homes. Off came the hair, off came the myriad of undergarments. Ten minutes of rubbing makeup remover on my face and drab-me was back, drunk, tired.

I hugged Cindy, a little hard because I was suddenly emotional, and with a wave and a goodnight I stepped out into the dull warmth of London at 4:45am.

I walked the four or so miles back to my hotel, my mind blank and stunned. What was so sad about it all was the fact it had been such a momentous night that I couldn’t grasp it, and it felt like a dream within a dream, something that had happened to someone else. It was the longest night of my life, but also the shortest.

Would I do it again? Probably not. You need to be comfortable to have fun, and I was terrified, then drunk, then terrified. Did I look good? Hell yes. Was I terminally afraid of interacting with anyone I didn’t know? Hell yes.

I’ll always remember the sound of my heels as I walked the pavement towards the club, grasping my friend’s hand which gave me an internal lifeline that genuinely stopped me from having an anxiety attack.

And that’s enough to make it a wonderful, scary night.

Stay beautiful you wonderful creatures of the night. Be true to yourselves, and be less of a coward than me.


2 thoughts on “Operation Terrified

  1. I have to say I admire your courage hun.
    And also I feel a little sad.
    I know you’ve now experienced (for a little while at least) life outside as a woman but it’s a shame that it wasn’t as pleasant or as uplifting as it could have been.
    Maybe you’ll have a change of heart and try again, or maybe not.
    But sweetie you have gone much further than me and I want to thank you for sharing your experiences.
    Both good and bad.

    Liked by 1 person

  2. As someone who has also just recently gone out for the first time (not clubbing, playing Pokemon cards because I am Oh So Fashionable and With It as a early 40s year old) I can totally relate to this whole post. And, honestly, such bravery here – not cowardice at all (though I totally can see why you thought otherwise).

    I’m years late in offering comment, but I felt (once again) moved to comment.

    Liked by 1 person

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