Skype Disaster Pt. 05: A Surprise Meet

Before I continue, can I suggest that if you don't like a story you simply move on to another rather than leave stupid, pointless anonymous comments? I'm not a published author or an experienced one, but all my stories contain elements of truth which is what prompts me to write about them. To the rest of my readers I hope you enjoy my stories because I certainly enjoy some that I find here, and I really do appreciate your comments and feedback. Xx

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During the long journey home in the car I pondered on the events of the previous few days and wondered where all of this might lead. OK, we didn't have sex, but we certainly opened up discussions!

Georgia's life to this moment had been typical of most gender dysphoric girls, confused and troubled. It all started when I was about 9 or 10 years old with trying on various items of female clothing and a growing admiration for the female form. Not in the usual pubescent boy way though, providing sexual excitement. When I looked at a nude woman in Playboy or other magazine, I wanted to have her features. Her breasts, her curves, her painted nails, her hair, her genitals.

I had hidden Georgia from the family and the public with the exception of occasional solitary outings and photographs published on the internet to demonstrate, in a way, her very existence.

As Georgia, who started out as being a small part of me, to now, when she is very much in control, I have always fantasised about being recognised as being female and as a result, being treated as a woman in normal life.

I used to imagine my same normal day, getting out of bed, showering, getting dressed and so on and going about my normal days, but as Georgia, not as her male alter ego. These dreams were uneventful. Just a girl going about her day. Rarely was there any sexual content or adventure.

But after decades of hiding, as Georgia took over, and I started to take small doses of hormones things changed. Suddenly Georgia was sexually aware and this began to affect everything that I do, especially when dressed.

When choosing clothing, makeup, accessories my mind is always on how I will appear and especially, how it might make me more attractive, to men. At no time did I ever consider how attractive I might also be to women, and that's another story altogether.

My imagination now frequently leads to sexual encounters of one type or another. Sometimes just complimentary remarks from guys encountered during an outing, and sometimes to passionate sexual encounters where I am taken to new heights of orgasms never before experienced.

All of this has changed my perception on life, and more importantly changed my outlook and expectations leading me to becoming less risk averse, and thus much more brave to a point where I seek sexual encounters. That said, as a TGirl at my age, men don't form an orderly queue.

Another complication is that, although Georgia is realising a new sexual awakening, I am old fashioned and have a strong preference, if I am to have sex with someone, for it to be with someone I actually fancy. This immediately writes off most applicants for my attention received via the internet, either because I simply don't fancy them, or because there is so little information, including lack of a photographs, about them in order to be able to make a judgement!

And so, after much consideration on my journey home, and in the days following, I decided that I do fancy Tim a lot. Quite a lot, actually, and when we next meet we should have sex.

This momentous decision depends of course on whether Tim feels the same way, and looking back at our recent meeting a couple of things stand out. How the hell did I manage to get the courage to touch his crotch, let alone give him a blow job, and also, why did I then not ask him if he wanted to make love to me? Hindsight can easily piss one off, I thought.

Monday marked just another week and being less busy I was able to dress and take a walk along a cliff path to enjoy the sunshine and get me head back together. Despite my best efforts I could not stop thinking about Tim and started to imagine what might happen when we next met. It was clear to me that I wanted him to join me in bed, and I began to wonder what we might do, what positions he would prefer, what I would wear, and more importantly, would it hurt!

And so my focus turned to that last question and I spent many a happy hour Googling to discover what preparations I should be making for the big day.

Whilst all of this was occupying my head during the next few days My regular Skype meetings with Tim went ahead as usual and neither of us discussed our next meeting, although Tim did say how much fun he had, and once made an oblique reference to my oral skills, with a very cheeky grin on his face. I took this as being positive!

The outcome of my web searches led me to discover a few basics: I should always clean myself out in readiness. I should stretch myself in advance to learn how to relax and make sure no damage was done (gulp). And finally that some positions were better than others for inexperienced girl like me and it was important that he be gentle.

All of this seemed completely sensible advice and I was already used to cleaning myself out anyway before using my fingers or anything else. I also thought that I could, probably, rely on Tim to be gentle as that seemed to be is normal behaviour.

This left stretching, and positions. I decided to do more research on positions as I assumed that Tim would also be a novice on that subject, with reference to anal sex anyway, I thought. So I set about stretching!

Some time ago I bought myself a set of three anal plugs, and a "lifelike" dildo from Ann Summers. (not in person you understand; from one of her shops)

I did try on one occasion to get the largest plug into me, using a lot of lube and much relaxation, but failed. I put this down to the fact that it was ribbed and it hurt like mad! I had managed to get both the smaller ones in and so I decided to start with the medium size one with the aim of eventually being able to get the largest one in without any pain. Estimates suggested this could take a day or two or up to a couple of weeks to achieve. Many suggested using poppers to help the process but after looking up poppers on Google I decided that they were definitely NOT for me. I decided that Georgia was a natural childbirth sort of girl!

I always disliked dildos after initially buying very hard and rigid ones and not enjoying them in the least, whether they vibrated or not. But the one I bought was softer and about 7-8" with a sucker on the base. At the time I considered this was about as real in terms of size and feel as I could get.

I used this for a long time and it did give me great pleasure until one day I left it behind in a hotel - Oops.

Each morning I took to cleaning myself out using a simple enema squirting device before heading to work. In my office I started to practice for about a half hour twice each day sliding the medium sized plug in and out of me whilst taking on various different positions and wore the small plug more or less all the time that I was in the office. After a week and a few failed attempts, I eventually took the larger plug and was, frankly, overjoyed! Looking at it closely I judged that at its widest point it was as big in girth as a pretty big cock. Certainly one that was bigger than mine, and a liitle larger than Tim's, based on what I seen.

After a few more days I was able to take the plug relatively easily as long as I used lube, and came to wear it for a couple of hours each day. Compared to the medium plug its presence in my butt as I walked was very evident. Very evident indeed.

I experimented inserting it whilst in various simulated sex positions and found little difference but concluded that inserting a plug was not like being fucked and I decided to buy myself a new dildo next time I passed an Ann Summers. Doing online research I was amazed to see them advertising a realistic 13" dildo. Really? I thought. How many guys have something that big, and how many weeks or even months of training would it take for me to be able to get it in, even assuming it was possible?

It was three weeks since our last meeting that I needed to travel to a meeting and on this occasion, meetings were to be scheduled over two days requiring me to book two nights in the hotel.

I drove up during the afternoon stopping off on the way to sit on the beach to eat my lunch. I was wearing my business suit which was not the best thing to wear for a beach lunch, judging from the attention I drew from holidaying families. I removed my heels for the short walk from the edge of the sand to a suitable place to lay out my rug and have lunch.

A few metres in front of me a couple were soaking up the sun, lying out on their towels and it quickly became clear that the guy was trying to look up my skirt, and whilst I was content to know that I was wearing tights on this occasion, I also wondered what he might have seen had I been wearing stockings. I smiled at the thought whilst deciding to make his day by not keeping a ladylike stance all of the time, frequently opening and closing my legs whilst pretending to shift around on my rug. I love the power that a woman wields at times like this! I made his day, I thought, as I returned to my car.

The hotel was one that I hadn't used previously and having pre-registered and paid I decided to risk arriving without changing, figuring that all I had to do what give a surname and wait for a key card.

"Just checking in please," I said to the very smartly dressed receptionist.

"Can I have your name please? She asked, and as she looked for the booking there was a momentary pause when she saw the booking was in my male first name before she simply said, "Thankyou Madam, you are in room 664, enjoy your stay. If you need any assistance just call reception on 100." And she handed me a key card.

I sighed in relief as I picked up my bag and walked to the lift. Such encounters were always stressful for me but on this occasion the receptionist made it easy for me, and I was pleased.

I unpacked, hung up my jacket, kicked off my heels and lay on the bed. I decided to call Tim rather than wait for his call.

"Hi, Tim, It's Georgia," I said, "I've arrived."

"Hi, how was the drive?" he asked.

"Usual traffic, nearly 4 hours," I explained. "Are you free for dinner tonight?"

"Not too bad I guess," he said, "I'm afraid I won't be free tonight for dinner, I have to meet a subcontractor for dinner, a late arrangement, I'm really sorry."

His comment hit me like a hammer blow as my heart sank.

"Are you OK?" he asked, with a very concerned tone to his voice.

I was gutted and a sudden realisation hit me. I had fallen for Tim and this simple event was a huge blow to me, even though we had planned nothing in advance.

"No, I'm fine," I replied, "I'm fine. No problem. I had planned to eat in tonight anyway," I lied.

We talked for a few minutes but Tim was obviously still at work and under pressure to hang up. We agreed to meet for breakfast before the first meeting.

As I put my phone down, peering at the screen, a wave of what felt like depression hit me again and for a few minutes I sat thinking about what might have been. But Georgia was used to rough times and I quickly pulled myself together and decided that I would order dinner in my room and maybe even watch a movie. I decided that a pampering was called for.

I poured a bath and threw in some bath bombs, determined to have a great evening. Setting up my iPod nearby I relaxed and enjoyed a long soak.

Drying myself off I donned the gorgeously soft hotel robe and ate dinner wondering what to watch on the TV. I decided that, as I had a lot of clothes with me, I would dress like a hooker and watch some shemale porn, and maybe even go on cam if the wireless was up to it. This is something that I used to do several years ago but stopped after a number of bad online experiences.

I exaggerated my makeup with strong eye shadow and silver eye liner. I added false eye lashed and deep red lipstick which I thought always made me look quite severe. A bit like a dominatrix!

I laughed when I looked at the finished effect in the mirror.

I Painted my toenails a bright red. This is a real treat and takes such effort is only really worth doing when I am away for two or more nights, or for very special occasions.

I rummaged through all my bags to find a set of very long false nails that I had bought from the internet by mistake a year or so ago. I found them eventually and glued them on very carefully, it immediately becoming clear why I hadn't worn them before. They were more like talons than nails but, I concluded, went well with the porn escort image that was appearing before me.

I wore my most slutty (NOT my usual look I hasten to add?) lacy black lingerie and finished off with some new fully fashioned grey nylons. This was a major task given the length of my nails and in hindsight I thought that I should have put on my nylons before my nails.

I put on my long blond wig which I had spent a lot of money on but rarely used as I didn't think it suited me that well, and added some large multi hoop earrings, bangles and so on.

I stood in front of the full length mirror and what I saw was someone else. Definitely not the Georgia I knew. Much more a milf dressed to the nines ready to appear in a porn movie. I was impressed.

I found my 6" red patent heels that I had bought several years previous but was unable to master walking in. I have seen many mainly young women out on a Saturday night, heading for the club, clearly barely able to walk, with a stance that made it clear to everyone. In these shoes I became an exaggerated version of those women and had come to assume that I would only ever wear them in bed, for sex.

I lay on the bed and after a while catching up with emails, rummaging around in Facebook and WhatsApp I decided to take some photos and update some of my web pages. This was always fun as not having a camera with a remote I had to use the delay timer. This often results in pictures where I have not quite made it back to the bed, or am looking rather dishevelled. It's always a good laugh!

After uploading some photos and chatting with a couple of friends I searched for tranny porn sites and settled down for some entertainment.

After an hours or so I was startled by a knock on the door and assumed it must be someone coming to take back the dinner plates.

I quickly wrapped the robe around me and, picking up the tray, opened the door.

What greeted me took my breath away and I nearly fainted. It was Tim, and I was lost for words, my face surely expressing my shock. Had I not been wearing heavy makeup I'm sure I would have appeared white as a sheet. Tim also looked surprised, if not shocked.

"Georgia? He asked.

"Yes, Hi, Tim," I replied, in stammered stages. "Come in. I thought you were tied up tonight. Come in and let me dump this tray outside the door."

Tim smiled and walked past me into the room, simply touching my waist as he did so. I closed the door and managed to smile, although I'm not sure how.

Tim looked me up and down and moved in to kiss me. I tilted my head as he did so and felt his lips on mine first gently and then after a momentary pause more passionately sending my head into a spin as he pulled me close.

"Wow," he said as he stood back, holding my hand. "I didn't recognise you. You literally look like a different woman. Wow."

I was recovering from the shock by now and it was, obviously, lovely to see Tim again, my racing heart being confirmation of this. I was also becoming aware of a hard-on in my knickers as I had not bothered to properly tuck or tape, there being no point if I was to watch porn.

I sat on the edge of the bed as Tim sat on the only chair and studied me in some detail.

"As you weren't going to come I decided to pamper myself and spend some time watching a movie," I lied. "As I had brought a lot of my stuff with me I decided to have a bit of a sort out and try on a few things I had not worn for a while, if ever," I said, lying again.

Tim just smiled at me. "I love your nails," he said, "and those shoes, well, how on earth do you walk in them?"

"Thanks," I replied. It was always nice to be complimented, even if I did look like a tart, I thought. "Actually, I can't walk in them. They are far too tall, so I keep them for bed only."

Predictably, Tim grinned with approval.

"So you wear them to bed?" he asked, with a knowing smile on his face. "Every night?"

I knew that if I was going to continue with this charade I was going to look pretty silly.

"Actually. To be honest. The truth is, well, the truth is that I decided to pamper myself and have a night taking some photos and, well, wearing some stuff I rarely wear." I paused whilst I wondered what to say next.

"And I decided to watch some tranny porn too." I blurted out.

Tim laughed. "So, what is under your robe? Am I allowed to see?"

"Of course," I replied, and stood up, moving a short distance away from him. I turned in a way as to appear provocative and alluring, and was grateful that I couldn't see myself in the mirror. I undid the robe very slowly, teasing him as I did so, just letting him have glimpses of what was underneath until I finally faced away from him and let it slide slowly off my shoulders to the floor exposing more of my underwear bit by bit.

As it finally rested on the floor I turned to face him. His face was a picture, and he had a huge bulge in his crotch. I slowly moved toward him and sat astride him on the chair, bending down to kiss him as he held my waist.

We kissed like this for a while allowing him time to explore my black thin lacy clothing as we did. Tim was a great kisser and in his arms I gave myself to him.

As we broke off, Tim said, "Tonight Georgia you are like a completely different woman. Seriously sexy. I mean like something I've only ever seen in films. Your blond hair is amazing, and somehow, even though it looks so different it really suits you. Everything is so different, and yet you're still the Georgia I have come to love."

I think Tim likes it, I recall thinking, and then dwelled more on his comment, "The Georgia I have come to love." This went around and around in my head as I tried to work out the consequences of it.

I sighed a deep sigh as I looked into his eyes. "We women have the advantage of being able to be anyone we want to be. I can be a smart business woman, in a pin striped suit. I can be the casual summer beach babe in denim shorts, sneakers and tee shirt with hair tied up in pony tails. I can be your slut or your sex slave, dressed just as I am today." I laughed, "or I can be your sister, or, in my case, your brother too!"

"In fact," I said, "I really don't understand why more guys don't date TGirls like me, given the advantages."

"There is no doubt, Georgia, that I am a very lucky guy." He said.

"And I am a very very lucky girl." I replied, as we embraced again.

As I kissed him deeply, holding his face in my hands, he massaged my breasts and I wished that they were real so that I could feel his touch. None the less, he had the same effect on me. As I looked at him, with hands on his face with huge long bright red nails I knew that I was the woman in the room, and that we were about to have some real fun.

I stood up and flicked my very long blond hair over my shoulders. I tried to tuck my cock back between my legs without Tim noticing but it was fighting back, and he had already noticed. Likewise, he was making a vain effort to rearrange his own in his trousers.

"Have you eaten?" I asked, "How long can you stay?"

"I rushed dinner as I knew that I just had to get here to see you. I'm sorry I didn't give you any warning, but then I guess I may have missed meeting Georgia the porn star," he laughed and slapped my bottom as I turned.