Driving Home - Getting Braver

After my experiences meeting Steve on my way home (see Driving Home), I decided it was time for me to become braver, or rather less fearful of being out in public.

Meeting Steve had exposed me to face to face contact with not only another actual human being, but a real guy, for the first time ever. I concluded that it had been Steve's patient, cool manner that had led to our hotel encounter on our second meeting, and I knew that a similar meeting with a different guy would probably not have ended up in bed, but simply a short conversation in the car park.

In fact, Georgia had quickly run from many a near encounter many times during her past. Simply seeing someone approach her car would ensure she left quickly, avoiding any face to face encounter.

Her fear had been built up over decades of being a crossdresser, and started well before she really understood her own sexuality, redefining herself as being trans, or a TGirl. The general public did not accept crossdressing in any way, shape or form, except during stag dos, or perhaps at Halloween. She had often been exposed to jeers, bullying and had been humiliated on more than one occasion, ensuring greater care and caution in the future.

Somehow though, Steve's approach to me in the car park that evening had been different, and I concluded that it was simply him. His politeness, caution, appearance, smile and general maleness that ensured I did not run away, even though every cell in my body was telling me to.

As it happened, Steve had turned out to be a true gentleman and great and patient lover, and since our hotel encounter and farewell breakfast the following morning, I have thought about him many times over the following weeks. Many times.

Whilst we did exchange telephone numbers, it was on the pretext that next time we were travelling that way, at some distant point in the future, we would text each other to see if our paths might cross again. We have exchanged texts a few times since, but no opportunity has arisen where we were able to cross paths.

In her normal way, Georgia had a very low self-esteem when it came to how she appeared to others when in female mode, and she had always convinced herself that she could never pass as a female except at a distance. A very big distance.

Apart from anything else, her age was against her, and she assumed that she could never be viewed as a sexy woman. In hindsight, she concluded that this view was very sexist and ageist too.

It was this mindset that had held her back from integrating with real life, preferring to continue to live in her secret world, with 99% of other guys who like to wear female clothing.

Since my bedtime fun with Steve, and especially after having dinner and breakfast together in a public place with no adverse reactions or comments from others in the vicinity, I have decided to become braver and in anticipation, I have made a list of things that I needed to do or work on and improve.

Now that I have finished the list, frankly it is longer than I had expected it might be, and I find it really quite depressing.

My list looks like this:

Buy new real hair wigs, and learn how to style them.

Throw out clothes that really are completely unsuitable for a woman of my age to wear. This was especially scary as I actually consider most of my skirts are too short, and my heels too tall for normal, everyday wear.

Concentrate on my preferred styles and discard those that clearly don't suit me.

Visit a dressing service to get makeup lessons and try on different wigs and outfits to see what works best. Basically, I am still too scared to seek advice at high street makeup counters.

Buy more makeup, and get a bigger bag as my two are already getting hard to zip up.

Buy some shoes with 2" heels or lower to reduce my visibility when out and about. Clicking stiletto heels are, I have concluded, too much of a man magnet. I know this to be true, as I used to be one (a man), and the sound of approaching heels always drew my attention, and still does, but for different reasons these days.

Lose weight. Ouch.

Buy new body shaping underwear. My bum and hip padding is now well past being suitable to wear and I should have discarded it to landfill some months ago.

Get a proper, professional pedicure. I can already do my own finger nails though.

Find out how to shave without getting terrible rash and ingrown hairs afterwards, which completely ruin the appearance of my skin and negate the whole point of shaving.

Buy some feminine glasses.

Go back on a small dose of hormones. It has been a while since I came off and most of the effects have now worn off completely. I really miss the sensitivity of my nipples and the softness of my skin and hair but the biggest problem is my lack of feeling of being feminine. It's hard to describe, but hormones changed the way I responded to people, and my partner noticed that I smelled differently. Different pheromones, I guess. My boobs have shrunk slightly too.

Try to raise the tone of my voice. This has to be a long-term target. Probably not easy, but rather important if I am to interface with others more often.

Get out and meet other TGirls like me.

The list is long and parts of it will be very expensive and so I will have to work on it over a period of time, as my available budget will allow. And so my adventure started.

Work has been very busy and as a result I have travelled more than average lately. Whilst being very tiring, travel does present me with numerous opportunities to be me. Georgia. On longer journeys in the car I am able to travel completely dressed, and nights away allow me plenty of time to practice makeup skills and go clothes shopping.

And so, with some trepidation, I decided to book my first dressing experience at a location in Hampshire. This would provide a basic grounding to allow me to buy more of the right makeup, and also hopefully, to point me in the right direction of styles of clothing and shoes to buy. I have just completed a large assignment, and so the budget was available for a spending spree.

I planned to arrive at the dressing service fully dressed so that they would immediately know what they were starting with, for good or for bad. I would then continue on to my hotel, hopefully with a new face and looking fabulous.

I had already checked-in online for my usual Premier Inn. All I had to do then was pick up my key from one of the reception machines. Once checked-in I was ready to go shopping, using my new list as a guide.

Rather than wear my business skirt suit for the drive, which would be my usual first choice, I wore leggings and smock top with a long cardigan. I topped this off with a collection of bangles, watch, two rings and my 4" patent heels, which I love and could not bear to leave off.

On arriving at the dressing service, I was as nervous as a patient waiting for a heart operation! My fears were quickly allayed though and I received a fabulous welcome from the owner and some lovely compliments on my casual look.

We talked over tea for an hour or so and perused various outfits that may suit me.

We started with trying on numerus wigs and I could not believe how some styles looked so great whilst others were conspicuously a no go. This exercise was worth the visit on its own as wigs are expensive and often not returnable if you get it wrong when ordering online.

Having chosen three possible options, we moved onto makeup lessons, looking at different combinations to suit different occasions. Summer, daytimes, evenings, parties. Whilst I knew it was not easy, I had no idea how complicated makeup can be, and I found myself having to take notes for each option, forming a list of products that I needed to buy, although I did already have a fair bit already, even if I didn't know how to use them.

We finished with a normal daytime look and then moved on to choose different styles and colour combinations of clothes. I loved this part of the day. I lost count of the number of outfits I tried on and made sure I took photographs of those that worked well. Some suited an auburn colour wig, and some a medium brow. We agreed that I wasn't a blond bombshell, or even a small bullet!

We talked body shaping wear and I had an opportunity to try on various vintage and modern shapewear, including spanx. different bra types and different silicone boobs to see what sizes suited me.

Some items were available for sale and I did buy new boobs, as mine are split, a collection of clothes and one wig.

It was simply the most exhilarating and life asserting 6 hours of Georgia's existence and I regretted not trying it before. I made a note to go again, and to try to go with another TGirl, as couples often go together as support, or for fun.

I left for the remainder of my drive looking very different to when I started. My makeup was flawless and my new wig made me look like I had come straight from the hair salon. I concluded that my old wig had seen better days!

I was stylish in some of the new clothes I had bought, and wore some red kitten heels that she agreed to let me borrow. I promised to drop them in on my return journey.

I felt fabulous and my confidence increased by 50%. This was exactly what I wanted and what I had decided was needed in my life if I were to climb out of the cupboard!

I arrived at the hotel, parked in the nearby car park and walked the short walk to the reception, dragging my usual two cases behind me. This was to be the first time I had checked-in fully dressed, and I was very nervous, although boosted by my new appearance.

I walked straight past the reception desk where the woman looked up, gave me a big smile and then re-focussed on her screen. I was relieved!

I entered my details into the check in machine and my room key was dispensed in short time. I headed to the lifts where there was already a man standing waiting.

As I approached, he turned, presumably alerted by the sound of my heels. As the doors opened, he gestured for me to enter first and followed me in, looked at me and asked what floor I required. "Five please," I replied, trying to raise the tone of my voice without sounding like an impersonator with a sore throat.

Entering my room, I was both relieved and elated, and whilst I was pleased that I did not have to engage in conversation with anyone, I was also slightly disappointed. Such is the life of a closeted tgirl, I thought.

Usually, after unpacking to hang up some clothes and distributing my various toiletries and makeup bags around the room, I would get changed into drab, leaving on my underwear, and head out for dinner.

This would require removal of jewellery, wig and makeup and on this occasion, I decided that there was simply no way that was going to happen. And so, I sat on my bed, switched on the TV and considered what options I had to get something to eat that did not require my defeminisation! (Is that even a word?)

I decided that I had two options, or maybe three.

I could walk around the corner to the local supermarket and pick up some sandwiches and maybe a yoghurt. This could easily be done without much conversation with the checkout operator, and there might even be a self-service option.

I could simply head into town, a 100m walk, and buy dinner in any one of the many food outlets. I thought the nearby Thai restaurant would be a good option as I have eaten there before and know the layout and routine, or a longer walk to the LGBT friendly London bar near Ocean Village. The Thai would be a first for me, and a real challenge, and be very scary, but I have been to the London several times before, usually dressed in a half drab half girl outfit. Yes, it does sound a bit strange, but it really wasn't. Nobody took the slightest notice of me.

Or, I could get online and try to find and chat with a nearby tgirl who was looking for a meet. I would be able to accommodate in my room so she could, if necessary, change and then head out together. Company would be great and potentially reduce the possible stress and risk, provided she was reasonably passable.

As a very nervous tgirl, all of these options went around and around in my head until I knew I had to make a decision, or simply jump off the roof.

Rather than jump, I scanned tvchix, fabguys and a few other sites to see who I could find online. All those I found simply wanted to meet for "fun", which essentially means sex, but this wasn't what I wanted.

I posted a meet request on the off chance of finding someone at short notice but only guys responded. As I reached for the log out button, a message arrived from yet another guy, but this one was very long. Not the usual one liner.

Intrigued, I read it and it sounded very genuine, and from a very polite gentleman. He was experienced with tgirls and explained that he was very happy just to have dinner with absolutely no strings attached. When I responded, he immediately sent me a couple of photos of him looking very smart, in what I considered to be working clothes. It seemed he was also in town on business, and in a nearby hotel.

My heart raced as I zoomed in on his photos and examined him in minute detail. Sad, eh?

We exchanged a few more messages and he emphasised that he was very happy to lead when ordering food and drinks and would ensure my complete safety and freedom from any third-party aggravation.

After a 10-minute pause to collect my thoughts, I agreed to meet him for dinner. His hotel was further from the city centre than my Premier Inn and so he would walk to mine to meet with me first.

I had an hour or so to agonise before I had to meet him and so I decided to freshen up with a quick shower and change. I took great care not to destroy my fabulous makeup and after drying myself off, I moisturised and applied some of my favourite Paris perfume.

As I sorted out some lingerie to wear, I wondered if I should clean myself out, although I had absolutely no intention of letting anyone have their way with me. But it felt girly to be super-clean, and so I did.

After putting on my underwear and touching up my makeup, I then spent most of the remaining time laying out outfits on the bed trying to make a decision on what to wear, whilst simultaneously rebuking myself for taking so much time to make such a simple decision.

Finally, I settled on a white silk blouse under my new dark pink skirt suit, nude stockings and maroon Mary Janes. Adding some jewellery and packing my small evening bag I was finally set to go, but as I finally adjusted myself in the mirror I wondered if I was a little over-dressed for a burger bar. But it was too late to change.

As I exited the hotel entrance, I saw Paul standing at the edge of the pavement. As I approached him, he seemed caught by surprise as I said "Hello" to him.

"Georgia?" he asked.

"Hi, yes, it's me," I responded, and offered him my hand.

"So sorry," he replied, "I didn't recognise you at all. You look nothing like your photos on your profile. You're gorgeous. No, really."

And with that, instead of shaking my hand, he simply raised it and kissed it gently, giving me a wide grin.

"Shall we?" he asked, gesturing for me to link my hand into his elbow.

Paul clearly was a gentleman, and old fashioned in his manner. "I'm in good hands," I thought to myself, as we headed into town.

We strolled at a slow pace and I focussed on being as feminine as I could, without exaggerating a bum wiggle, and concentrating on keeping my voice a register higher than normal. It seemed to work OK.

Paul was easy to chat to and although he had a tgirl on his arm, he was completely relaxed and normal. He was dressed in a suit and polished brown shoes and wore a blue shirt which looked freshly ironed. Certainly not one that had been worn all day. He smelled very slightly of cologne. As we walked together, arm in arm, I caught a glimpse of our reflection in the shop windows and thought we looked pretty good together. He was attractive, but not in an obvious hunky model type of way. He was a few inches taller than me, even though I was in 3" heels, making him about 6'3", at a guess.

He knew the area quite well as, like me, he travelled to Southampton on business fairly regularly. He was single, having lost his wife in a car accident several years back. He was a marine surveyor and travelled a lot, mainly along the south coast.

As we talked, he laughed a lot and I soon relaxed in his company and realised the evening would be far more enjoyable than sitting on my bed eating sandwiches and drinking awful hotel tea.

We chose a Greek restaurant and on entering were directed to a booth tucked away at the far end of the restaurant. There were numerous other diners already seated and I was aware that most observed our arrival, some offering a smile as we passed. I wondered what their brains had told them they had seen as Paul directed me to my seat before sitting himself down. He made me feel very special.

Paul sat opposite me and as we spoke, we both studied each other.

After discussion around the menu, and drinks options, Paul ordered for me as if we had been partners for years. He had a knack, presumably gained from experience.

"Georgia, I am so pleased I logged on this evening and saw your post. I had a lot of work to do, writing up reports, and I had pretty much decided to have a quiet night in, maybe grabbing a takeaway."

I laughed and told him that it was one of my options too, and continued to tell him what the others were too. This was the first time my being a tgirl was mentioned and it was me that mentioned it, so I made a mental note not to do that next time.

But Paul never dwelled on it at all. As we ate and talked, he would occasionally touch my hand over the table but never said anything inappropriate at any time at all.

For me, the cowardly tgirl in the room, this was a dream date and only the second time I had met a guy. The first being Steve with whom I have had two encounters in Bridport. Even now, when I look back on those meetings, I cannot believe it was me who was so cheeky and brazen. It still feels like it was a dream.

As we neared the end of the meal, with half a bottle of wine inside me to loosen me up a bit, we decided to find a nearby bar to continue our evening. Neither of us had to drive, and it was nice to be able to relax in great company.

Paul occasionally complimented me on some aspect of my appearance, clothing, jewellery or knowledge but without it appearing he was trying too hard. But it made me feel good and I returned compliments as and when the moment arose.

Paul picked up the tab and despite my prolonged protestations he refused to give in, so as we left the restaurant, I pecked him on the cheek as a thank you. He appeared to be genuinely surprised, which was lovely.

As we headed up the hill to a bar, Paul held me around my shoulders and so I responded by holding him around his waist, beneath his jacket. Somehow, it felt really good. Even normal. This was a guy with who I could easily become friends, I thought.

Letting me enter first, it was fairly busy and so we settled on two stools at the far end of the bar. As I struggled to mount the stool easily in my short skirt, Paul completely naturally held me and helped me up. As our faces moved closer during this manoeuvre, and my hands were on his shoulders, I could smell his masculinity and instantly became aroused. It caught me completely by surprise and I blushed.

"Thanks for that," I said, trying to regain some sort of dignity and straightening my skirt. "It's not a great outfit for mounting high stools."

"No, I could see that," he said, "I hope you didn't mind me manhandling you, but you did seem to need some help." His smile that followed tempted me into making some inappropriate remark, and to this day I cannot understand how I managed to resist.