Living The Dream 1 – What Have I Let Myself In For?

I’ve never felt the need to prepare a bucket list in either of my two lives.  I’ve learned the hard way that the best laid plans can be scuppered by unforeseen circumstances and these days I’d rather just focus on certainties rather than trying to tick things off an arbitrary list.  But if I was going to produce a bucket list for my feminine life, something that would feature prominently would be to spend a period living as Amanda.  Here, I’m not talking about a few hours dressed at home with, perhaps, an outing where I remained to all intents and purposes anonymous before changing back but, rather, assuming her identity and immersing myself in her world for a period.  Sadly, though, chances to spread my feminine wings are few and far between these days so that has long looked to be destined to remain a forlorn hope, firmly rooted in my fantasy world. 

I have no problem with allowing my mind to stray into fantasyland.  After all, the mere act of transforming myself into a representation of the woman I’ve always wished I was is the embodiment of one such fantasy.  My outfits of choice are another fantasy as I strive for feminine attractiveness despite the considerable challenges that nature has saddled me with.   And when I look in the mirror and feel the euphoric bliss wash over me, there’s a little voice that reminds me that it’s all a transitory mirage – that party dress will never be worn to a party or that workwear worn to work.  But that said, I can at least dream.

But I don’t want to denounce fantasy.  After all, if I’d never allowed myself to wonder what I’d look like as a woman I’d be missing out on a side of my life that gives me a lot of happiness and inner peace.  And what I’ve learned is that, just sometimes, today’s fantasy is tomorrow’s reality.  All of the things I’m quite happy doing now in my feminine guise – shopping, eating out, travelling on public transport – once seemed unattainable.  Of course, I’ll never attend a high school prom, give birth or anything like that but other fantasies now seem tantalisingly within reach.  I just need the opportunity to see them through.

With the house now full and opportunities for CDing all but a thing of the past, my only chances of unleashing the inner woman require a night away from home.  I don’t like lying to Mrs A so I only do this when I have a legitimate reason to be away but I can take the opportunity to take a bag full of goodies with me on those trips.  One thing struck me, however.  I check into the hotel as a male, I check out as a male and I feel a flutter of nervousness each time I walk through reception in my feminine guise in case the receptionist makes the connection; yes, I’m proud of who I am but I want to keep the two sides of my life completely separate, not give someone the opportunity to link them.  Moreover, it also gives me the feeling that I’m playing ‘let’s pretend’ and expecting the hotel staff to play along.  And as those thoughts swilled around in my mind, a particularly powerful fantasy started to form – why not book the next hotel in Amanda’s name, turn up as her and spend the whole weekend in her guise?  Suddenly, albeit in a small way, that bucket list entry seemed doable.

The more I thought about it, the more I liked the idea.  First of all, someone who turns up as a male, then walks through reception one hour later dressed as a female is a CDer pure and simple, there can be no other explanation.  Turn up as a female and spend the whole stay like that and, as far as the hotel is concerned, I could be anywhere on the TG spectrum.  And pick a hotel with a restaurant and that fantasy of dressing for a dinner date in my most elegant dress and highest stilettos could come true even if I’d be flying solo.  And most of all, these days I’m acutely aware that whenever I cross the gender divide, it could be for the last time and so I want to make each outing memorable in case the line is drawn.

The idea seemed straightforward – book the hotel in the name of Ms Amanda Johnson and then turn up in a suitable casual but feminine outfit and check in.  Change into something elegant for dinner and include a third outfit for breakfast the following morning.  Finally pack my bags and check out, still in my feminine guise thanking the staff for making the stay so wonderful and sit beaming in the car repeatedly asking myself whether I really did just pull all of that off.

Except….

My legal name, the name that appears on my credit card, isn’t Amanda Johnson or anything vaguely resembling it.  It’s difficult to leave the house dressed due to the presence of my daughter; even when she’s out, there’s an ever present threat that she could come home unannounced at any time.  Hotels require an email address, phone number and home address when booking.  The email address isn’t a problem as I have a separate one in Amanda’s name but giving both the phone number and home address run the risk of an SMS or letter addressed to Amanda being seen by Mrs A.  These were not insurmountable problems; payment could be made by PayPal where there is no check that the name being booked tallies with the name on the payment card used.  I could get changed en route.  A second SIM card would solve the phone number issue (and if the sim was kept disabled, no SMSs would get through) and if any post addressed to Ms A Johnson arrived, I could plead ignorance, scribble ‘not known at this address, return to sender’ on the envelope and put it back in the post box in the hope that the sender would update their records and stop sending stuff.  So the problems were solvable except for one thing.

I have enough trouble getting dressed and putting on makeup in the comfort of my house where the lighting is reasonably good and I can spread out, heaven only knows what sort of mess I’d make of myself trying to do it in the confines of my car.  I did contemplate seeking the services of a MUA en route but that would be additional cost which I wanted to avoid so I’d have to figure out a strategy myself.  And getting changed in public without drawing attention as I wriggled to get things off and on would also not be easy.

After a lot of thought, I came up with a plan that I thought could work.  Underwear (minus breast forms) and hosiery could be put on at home and worn under guy clothes to get me out of the house without raising suspicion.  I’d then need to find a quiet part of a car park or a lay-by on the way to complete the transformation.  Putting a skirt on over my trousers before removing the latter would preserve my decency but I’d need to be quick changing into my female top as my bra would be on show after taking off my shirt.  I’d need to leave my wig off while I applied foundation but it could be worn for the rest of the transformation and I’d just look like a random woman doing her makeup from a few feet away.  As far as makeup is concerned, I could just go with the bare essentials of foundation, brow pencil, minimal eyeliner & eyeshadow, false lashes, blusher and lipstick.  Nothing fancy but good enough for my arrival at the hotel.  Going down the minimalist route would also help after checkout when I would need to clean up and change back into guy clothes on the way home.

And so with what seemed to be a workable strategy in place, I took a deep breath and booked the hotel in the name of Ms Amanda Johnson.  Now there was no going back without losing the money I’d paid for the booking.

-o-O-o-

As soon as I booked the hotel, I felt a mix of euphoria, nervous excitement and dread.  With a click of the mouse, my dream was turning to reality.  I would be checking in as a woman, presenting as one throughout my albeit short stay and checking out as a woman.  My guy clothes being superfluous for all but the departure from home and the return a day later.  If I ever needed proof that my inner feelings were far deeper than just a need to CD, this was it and it felt amazing.

But there were still 33 days to go before I made the journey and over the ensuing days, my mind was working in overdrive imagining the various stages of my stay – check in, dinner, breakfast and checkout – and what I’d wear for each.  Outfits were planned in my mind (with items to complete the look purchased where necessary). Getting to sleep at night became difficult as I wondered how the stay would pan out.  What would check in be like?  Would I be addressed as Ms Johnson or would there be some issue that caused my bubble to burst before I’d even fully inflated it?  Would another guest engage me in conversation or make a disparaging comment and how would I deal with either?  Would I encounter hospitality or hostility?  These and many more unknowns were occupying my thoughts almost to the exclusion of everything else in my life.

But there was also a strong sense of dread.  Whilst I had a legitimate reason to be away from home and this was disclosed to Mrs A, I was being seriously economical with the truth – many would say that I was lying by omission – and that doesn’t sit well with me.  True, she’s given her blessing for DADT but she has no idea how far I take things these days.  And what if something went wrong en route?  A breakdown or flat tyre perhaps.  And what about the return journey?  I’d need to rely solely on a packet of makeup wipes and a small mirror to ensure that every trace of my feminine side is removed before showing up again (I normally wash my face with soap and water around six times after wiping off most of my makeup to be on the safe side!).  And it wasn’t lost on me that the whole premise of the trip – present as a woman throughout – also constrained me to remain ‘in character’ even if things started falling apart.  Unless I wanted to do a lot of explaining, there’d be no reverting to guy clothes.

What on earth was I letting myself in for?!

-o-O-o-

At this point, it’s probably worth talking about outfits.  As a nascent & closeted CDer, all I was concerned with were classically feminine styles – heels, hosiery and hemlines!  That was fine when I was firmly in the closet but as I emerged into the outside world, I soon realised that the styles I held dear looked out of place.  And with Kandi’s ‘Rules of the Road’, and particularly ‘Be Appropriate’ ringing in my head, I became far more conscious of what’s right for a particular setting.  It’s not always easy, though.  Many women these days just resort to jeans, a T-shirt or jumper depending on the season, and sports shoes.  I wear those in my normal life so they hold no attraction when I cross the gender divide.

As a CDer, that makes life quite difficult.  Women can wear pretty well whatever they want because they have the fundamental legitimacy to do so.  As a CDing guy, things are far more complicated.  Turn down the femininity to zero and it’s a case of ‘why bother?’.  Turn it all the way up to 11 and we run the risk of sticking out like a sore thumb.  It’s about trying to find the balance between the femininity we crave and the authenticity that women take for granted.  The bottom line is we have to think like women without really understanding exactly how women think!

For my trip away, I decided that I needed three outfits:

– Something casual but feminine for the arrival that would also be suitable for a trip to the shops.

– Something suitable for dinner in the hotel restaurant.

– Something casual for breakfast and departure.

Reviewing my existing ‘wardrobe’, I decided to try my black skirt, denim jacket and knee-high boots.  However, I needed a top to go under the denim jacket and thought that a red polo neck jumper could work.  I particularly wanted a skirt for check in to avoid any ambiguity on my arrival.

Dinner was more of a dilemma.  I really wanted to wear something special but was fearful of looking overdressed.  But despite my plans to dine alone, this was a special occasion and I wanted to feel that I was rising to the occasion.  I’d probably never have another chance to wear my black dress and favourite stilettos but I needed something to complete the outfit.  By chance, I saw a photo of a pashmina being worn with a dress and thought that that was just what the outfit needed.

For breakfast and departure, I decided to try trousers.  I know that many CDers view trousers as a wasted opportunity but people tend to dress very casually for hotel breakfasts so they would be less conspicuous than a skirt and, with a jumper on top (I’d spotted a very cheap one that I thought would be good) I’d probably blend in reasonably well.

To make sure that the outfits would work as well as I hoped, I used AI to give me an idea of what I’d look like in each one:

And that was really all the reassurance I needed.  It was now just a case of sourcing the items I needed and then playing the waiting game for D-day.

So would the stay be the wonderful experience I hoped for or an unmitigated disaster?  Next time, I’ll let you know how things panned out.