• Stephanie Ashton

The Sweet Escape

Gwen Stefani, The Sweet Escape, 2006


Well hello 2020 and here is my first blog of the new year. Bored of hearing about my shopping expeditions, nights out and travelling exploits? Me too! So instead let us have a quick run through of my dressing sessions from last weekend at the wonderful Boys Will Be Girls. I know that some girls live vicariously through those of us who have the opportunity to visit a professional dressing service regularly, so let’s go through my last session in all its glory. I hope you enjoy it!


Before launching into the detail, I will start by acknowledging that for some of my dear readers it may seem a bit strange that I am still hooked on the dressing service experience. After all, I dress full time socially, enjoy doing my own make-up, and go out and about whenever and wherever I like. So, you may well ask why I would continue to pay for the intimate dressing experience. What is my rationale and what psychology is at play?


Tgirls...huh...always lounging around...

This is a question I have challenged myself on many times. In fact, as part of my continual self-assessment of whether I am ready to transition, I regularly challenge myself on those things that still seem out of keeping with the broad objective of becoming a transwoman. This approach hopefully helps to keep me grounded and will stop me from just ‘doing it’ as a result of getting carried away with myself. Well, the good news is that after thinking about transitioning for 30 years it is clear to myself, at least, that I am transgendered. Phew, that is a relief or else all the time and effort put into my female life would have been a complete waste of time. And happily, I can say with confidence that I clearly understand my continued desire for dressing services and it goes something like this…


It is brilliant fun! Yes, my reasoning is incredibly simple and is primarily because I am a girlie girl who loves dressing up and being pampered. Had I been free to dress up as a child, in all likelihood I would never have been out of my mothers’ shoes and dresses because I just love it all. More over, if I had been born a woman, I can guarantee you that today I would never be out of the nail studio or hair salon. Yes, to some it may be vain or superficial, but I love being glammed up and the sense of beauty that goes with it. Who said I am high maintenance? That is slanderous. Rich admirers pay no notice to my detractors.


Stephanie comes at a reasonable price...for the right 6 figure dowry

On a more serious note, I have also concluded that my passion for dressing services is not in contradiction with being transgendered, but in fact supports it. Why? Well, as much as I like to think I know about make-up and female styling, it is still wonderful to be exposed to new ideas about what my female self should wear. The make-up artists at the professional services spend all day looking at dressers and they develop an acute sense of what does and does not work for you as the individual. If you pay attention, you can learn a great deal about products and application, dress choices, posing, and many other things besides.


Then we come onto another aspect of why I particularly enjoy the BWBG experience. As a transgender person with a focus on transitioning, I have a deep respect for the owners and enjoy chatting to them about everything and anything to do with this life. I can see that as I transition, I will still be seeking an audience with them not to get a make-over, but to better understand how I adapt to the change in myself, lighter make-up routines, and many other things besides. So, it does all make sense. That is a relief.


Playing with different hair styles is a big love for me. I still enjoy the wow moment when opening my eyes to see the final make-over

With that pre-amble completed, let us now get into the nitty gritty of the two sessions from last weekend. As normal for my photo sessions, I had planned my outfits in a lot of detail. I am prepared to accept that the level of planning I am about to describe may sound anal to some dear readers, but for myself it is necessary to ensure that I do not travel from home and then realise I am missing something critical. Yes, in days past I managed to leave home without shapewear, and even on one occasion my breast forms. Don't ask.


Following my routine I had planned my outfits and shared my thoughts with Cindy in advance of the session to give her some insight into the level of madness about to unfold. Below is a picture of my loadout for this trip. I normally start planning my outfit choices by finding shoes and matching handbags I like and then find a dress to go with it. Sound backwards? Totally! However, it does make sense when you think about it. Being at the end of female shoe sizing (42) I often find shoe/handbag/accessory combos harder to find than dresses to match it. As a result the shoes now come first and then I find the rest.



When it comes to how many outfits to take, I need to think about this carefully as we can now get through lots of outfits in two sessions. In addition to Cindy having got to know what works for me, I nearly always arrive and leave dressed and with nails done so save a lot of time as a result. For this trip I planned to do 7 outfits of my own plus 2 dealers choice outfits. So, on this occasion, I left home with 9 outfits in total to give me dress down options for going out at night. Yes, I know that sounds a bit odd but honestly, after being dolled up all day, it is nice to stick on jeans and a top and go out wearing comfy boots.


So, what did we get up to in session one? Arriving at 4 pm it was lovely to chat for a while before we decided we should probably get on and do something. So, as the make-up went on, I continued to blether on about everything from boyfriends to my most recent antics and then voila, in the whip of a cats tail I was ready for costume one. As we had plans to go out later there would be time for three outfits and we went for the glamorous night time looks as shown below.


Black and Gold Dress with bow heels and faux fur jacket. Lovely

Vibrant injection of colour Latino style

Silver and black halter neck with silver studded black stilettos. Outfit made to pop with choice of blond Robin-R hair

Session one went super well until it came time for dressing to go out. Both my companions looked fabulous but had opted for sensible winter choices as opposed to the Newcastle tartlet look I appeared in. This resulted in me having a near existential crisis about my choice of clothing and 20 minutes later, I finally threw off my glittery dress and opted for jeans, a jumper top and boots. Pleased with my choice from a comfort perspective, I would shortly be very pleased with this his choice as we would end up walking quite a distance from where we would park the car to the Ivy in Soho, in the cold.

Love my fur lined boots hmmmm

Waking up on Saturday morning in my hotel room, I opted to lounge in the bath for a while before heading along for session two. We had a really nice meal at the Ivy the night before and I was enjoying myself reflecting on the conversation when suddenly it struck me that I should really get my ass in gear. Saturday was going to be another busy day involving a dressing session, shopping, and going out with friends at night. There was no time to lounge around day dreaming!


As I was going to have my make-up done at 10 am I opted to go to BWBG in boy mode. Whilst I detest spending any social time in my pretend skin, it simply made no sense to put on the war paint, only to scrape it off again an hour later. I have become very conscious about protecting my skin with the amount of make-up I wear daily so really did not want to put my face through another change in close succession.


So I happily hopped in a cab and off I popped to Shad Thames. Arriving In the area much quicker than expected, I opted to settle down in a coffee shop and grab some breakfast before heading along to the appointment. The young girl serving me was clearly amused by my painted nails at which point I felt obliged to tell her I was in disguise as a boy that morning. Following a bit of a show and tell with pictures on my phone she was amazed and said “shut up! Those pictures are not you!” Yes, that is the normal satisfying response. I then gobbled down my food, paid and strolled along to my appointment.


Thank god I had a solid breakfast this morning...tough life all these photoshoots :D

What can I say about session two other than it was a complete scream from start to finish? Again, we started by chatting about things various before getting through 6 outfits in the next 6 hours. The number of outfits was nowhere near as interesting as the stupid amounts of fun we would have taking the pictures.


Starting with a straightforward paper dolls dress shown below we produced some really nice pictures including some Steffie at work pictures which were fun. It was a nice way to break into the session. As is now the modus operand i, we went hunting for props for me to use in the pictures and this always prove to be good fun. So, entrance stage left the baby teddy saying “It’s a Girl!” Well done Teddy for not mis-gendering me.


Steffie at work. Truthfully, I would never get any office work done for flirting with the hot guys. What?! That is what offices are for!

Maybe I should consider this teddy as a replacement for my cat? He is cuddlier and does not require to be fed with roast chicken 5 times a day

The next look we went for was a black and gold sequin dress with black heels and a flick wig. It was at this time I came up with the idea of a 1970s key car party and Cindy busily went away to find a glass bowl and keys. What ensued was pure comedy. We first attempted to take the pictures on her SLR camera before deciding it might be more fun on the iPhone. The pictures we then managed to capture were a combination of being so bad/hilarious that we descended into fits of giggles. At one stage I had to ask Cindy not to look at me or else I would cry with laughter and ruin my make-up. Absolutely hilarious.


Below is the best shot of the car key party we managed to produce…which involved Cindy standing at the strangest angle known to the human body and myself attempting not to laugh. On a serious point...is that not the most amazing eye make-up? Absolutely gorgeous and what talent.


Steffie at a 1978 key car party thinking "Please be Mark from No.42..."

Following Carry-On Key-Car-Party I went and got changed again, this time into an ASOS jersey dress with silver studs shown below. I cannot tell you how much I love this dress mainly due the feeling of being wrapped in a wool blanket. I have worn this dress out and damn near fell asleep in a restaurant due to its warmth. As we say in Denmark it is very hygge. I cannot describe it, but there is something deeply feminine about this dress for me and it is maybe because it is so practical and something any woman would love to wear.


Bliss is a wool Jersey dress....how cosy mmm

Having forgotten to bring one of my six dresses from the hotel to the session, it was now the famous dealers choice time. Now, when you get to know Cindy, dealer’s choice is not dissimilar to winning in a raffle. Beforehand, you have no idea what you are going to get but you are always very pleased by what you receive. Well on dealer’s choice, Cindy struck gold three times.


The first of Cindy's choice was a gorgeous Bardot dress that typically I would not have had the courage to wear. The dress colours were gorgeous and I simply loved the dress on. Having bare shoulders is also a big bonus in terms of keeping cool as I can be something of a hot potato at the best of times. With the addition of the perfect hair I was immediately transformed into a pretty trans doll. I simply cannot describe how totally feminine I felt in this combination and every time I caught myself in the mirror it gave me a little “wow” thrill. That is quite some achievement to give me a wow after everything I have done as a dresser.

Oh my...now this is super feminine and I LOVED it!

So, having been serious for at least 5 minutes it was now time for some more silly antics. We had a bit of a debate over the next dealer’s choice dress before deciding to go for a retro housewife look that frankly made me look like a bit of a 1980s MILF. Once dressed, Cindy suggested in jest that I would make the perfect Jewish housewife at which point I was slightly taken aback. What went through my head in the next few seconds was hilarious and went like this:

“Oh no! Has Cinders arranged for me to be whisked away by some rich Jewish diamond merchant who I will be forced to marry? Hang on a minute…that might actually be okay! They treat their women well in that culture. I wonder how many diamonds he will give me for my birthday? I hope he is handsome. Okay, I could settle for him just not being totally repulsive…”


In truth, I am actually quite sub so if Cindy had told me that I had been sold off, I would probably have ended up celebrating Hanukkah with my new husband thinking, oh well life could be worse. In any event, producing the housewife set of pictures was an absolute hoot and the resulting images are quite amusing in themselves. I know, I know this transgender business is meant to be serious and deep, but I just do not seem to get it. I just want to play around all the time!

The perfect wife before the addition of red wine..
Oh bloody hell, I have ruined his dinner again...
Oh my I wish he would clean up after himself...

After the housewife antics, we had just enough time left for one final dealers’ choice. Yet again, Cindy selected a brilliant combo and we decided to go for it. Using my shoes from the day before, combined with a sequin skirt and lace bodice we produced a really nice night time look. Was it a bit tarty? Err yes thank you. In summary, anything that shows my legs off is A Okay with me and fair game. The choice of hair style and colour was perfect for this outfit and again I felt very pretty with a favoured look of blond on black and silver.


This would have been perfect for my night out in Liverpool next month...

As always happens, the session ended too soon and I needed to say my fond farewells and dash back to the hotel in a cab with a memory stick full of pictures in hand. Due to some logistical miscalculations I looked like a pack horse when I left Cindy’s, with bags and dresses everywhere. That did not bother me at all however, as I had a brilliant time and was still dining out on the wonderful after glow of the experience.


On arriving back at the hotel, I realised that the silver lining to having forgotten to take one of the dresses to session two was that I could now wear the offending dress to dinner with my friends in Soho. I narrowly avoided the trap of just 'faffing about' and headed straight into town in a cab as I wanted to get to a Boots for make-up brush cleaner and other things that are stupidly expensive back home compared to UK shop prices.

Oh hang on! I cannot go out in Kitty slippers!
That's much better and a nice fur lined coat to go!

Arriving at the east end of Oxford Street earlier than expected, I got out of the cab at Tottenham Court Road Tube Station and nipped into the Boots. As can happen, I had a slightly creepy experience when the security guard insisted on basically following me around the shop staring at my legs. It was one of those pleasing and at the same time awkward experiences. Welcome to the female world I guess. leaving my security guard friend agog in Boots, I proceeded along a very busy Oxford Street, turning down Dean street and into Soho. Arriving before my friends, I popped round to a favourite watering hole for a quick drink and catch up on my social media, before going to meet my friends in Balans.


In summary I had a really nice evening out with two dear friends however, I will to spare you the details of our intense debate on transitioning, hormones and geo-political affairs. What!? On a night out talking about politics and oil? Yes, us transpeeps are so high brow you know. Sadly, it was soon time to leave the company of my friends and as we left Balans restaurant the devil in me was telling me to go for a drink somewhere and take in the sights.


Pornstar Martini please!

Now this would normally be a perfectly fine idea but due to my legs being on display in a packed Soho, I immediately attracted the attention of some less than desirable characters. What do I mean? I basically became the pied piper with three different guys following me down the street telling me how much they were in love with me. Gosh, men do fall in love quickly these days don’t they?

It quickly became evident that the final rat was not going to go away and even if I went into a club, he was just going to follow me. So, I decided it was a less rapey option to skip the drink and just go home instead. I hailed a cab that fortuitously came past at exactly the time I decided to leave, went home, got in my room, threw off my clothes, and jumped in the bath. With the addition of some tunes on my iPhone and red wine it was complete heaven.


Final Remarks

As you can see, I am still totally in love with the dressing service experience and had a brilliant time. In addition to enjoying the company of the ladies at BWBG, I am super happy that I still get a buzz from being dressed up and pampered. I also did some other fun things on this trip to improve my TG credentials including having a nice time at the Victoria and Albert Museum on Sunday before flying home once again as Girl-me. But that has all become so run of the mill to me that it is not even picture worthy. My favourite pictures of the weekend were of me cleaning a toilet dressed as a Jewish housewife and what that says about me I will leave you to decide for yourself.

With that thought in mind, I will sign off wishing you all a happy and successful year ahead xx


Cheers everyone and happy 2020! xx