Skype Disaster Pt. 04: Exploring

It was late and the bar at my hotel would be closed so Tim suggested we drop in to a nearby club for a nightcap. I agreed without hesitation. It was either let the evening continue and enjoy the experience, or return to the hotel, end my first date, strip off everything that is Georgia and go to bed. No competition, I thought.

It was dark and there was a jazz trio playing in one corner. The club was about half full and the atmosphere reminded me of Ronnie Scott's in Soho about 30 years ago, but without the haze and small pools of sick on the floor!

Tim led me to a small booth near to the bar. "What would you like?" he asked, gesturing toward the waiting barman.

"How about a house on St Lucia, a boob job and a hunky man to live there with me?" I replied, with a serious look on my face.

"Can that wait until next month?" he replied, with a grin.

"Well, OK, if it must," I said, "I'll have a Dry Martini for now."

We sat and talked for a couple of hours. Tim sat close to me and sometimes held my hand, and occasionally kissing me very sweetly on my lips. We never engaged fully, and his tongue didn't make any unexpected appearances. Sometimes he would place his hand on my thigh, clearly able to feel my hold-ups, but he never wandered nor moved in a way as if to explore them, or me.

I had known Tim as a client and eventually as a friend for many years of course and we always had a good time when we had dinner together previously, but there had never been any indication that he was gay or bi, and to be honest, as I thought about it over a few more Martinis I was pretty sure that he was straight.

As we neared the end of the evening, which was in fact early morning, the conversation moved onto how Georgia came to exist. It was a story that I had told Tim when he first discovered her on Skype several weeks back but had never really been explored between us again since. At least not to any depth.

I told Tim how Peter had always been different from the other boys at school. How he hated rugby, cricket, football and so on, and how he managed to avoid sharing showers afterwards. How Peter had been in the Boy Scouts and had bought copies of Men Only and similar magazines but instead of wanking over the images of bare women had simply admired their bodies, and their breasts in particular, dreaming of having his own.

I told Tim how I started to dress whilst away from home, stealing my wife's clothes from the charity bags and building up a small collection which was secreted in a bag kept well hidden. I told him how Georgia, or Sian in those days, would go out walking at night whilst her partner was working the night shift. How sometimes she would attract the attention of passing cars which would sound their horn at her, giving her a buzz of satisfaction as someone hopefully considered her to be female.

Like all crossdressers, Georgia came and went over many years, but never completely disappeared. It was as if she rested as while.

Tim was fascinated and on occasion wiped away my tears as I told my story.

By now it was impossibly late, and the club was due to close soon and so we returned to my hotel, Tim opening the car door for me once more. Something I was beginning to get used to!

"It's late so I'll walk with you to your room." He said. Again he placed his arm around me and we walked together through the hotel to my room. As I rummaged in my bag, found the room card and unlocked the door Tim stood watching me with a satisfied smile on his face. Like the cat that had the cream.

As I stepped into the room I held Tim's hand and drew him inside with me, letting the door close behind me.

I placed my bag on the bed, removed my shawl and turned to Tim who had a puzzled look on his face.

As I began to speak he interrupted me. "Wait. I think we should take things slowly." He said. "We both need to think this through."

I smiled as he obviously thought I was inviting him to stop over, which, if he had wanted to I suspect I would have agreed to without hesitation, although also with a degree of fear, and excitement!

I placed my finger on his lips as if to cease his talking, and as I did I remember admiring my perfectly polished nails.

"Tim. My gorgeous Tim," I said, in an unexpected hushed voice, "Although I'd love you to stay a while, it's seriously late and we both have to be up again, rather soon., but I could not let you leave without telling you what an amazing time I have had. That's not to say that it hasn't been rather weird at times because of the history we share. But I really have had the most amazing date ever. Yes, a date, and I just wanted you to know that, and to know that you have been the perfect gentleman."

I paused for a moment to collect my thoughts and to see Tim blushing again. "The fact is... The fact is," I said, stumbling over my words, "I haven't been on a date before, and I'm not really sure what is appropriate to say, and what is not, but...Oh fuck, what the hell, some things need to be said before the moment goes. I think you're lovely Tim. A dream date, for me, and whilst I know that our relationship may not be quite the same ever again, for better or for worse, I have to say that...I fucking fancy you like mad!"

Tim waited patiently for me to finish and leant forward to kiss be gently again. As he started to break away I placed my hand around the back of his neck and pulled him back. As I kissed him more deeply he quickly took control and we started a passionate embrace. Our first. This time he kissed me deeply, and then gently, kissing me softly around the edge of my lips before exploring my tongue with his.

My head was spinning as I had never been on the receiving end of such an embrace before. Georgia had led a very sheltered life.

As we parted and I regained some composure, Tim asked, "Is it my turn to speak now?"

I smiled a broad grin, flicking my hair back behind my shoulders and pulling a few stray strands from my mouth whilst also untangling it from an earring. "Of course," I replied, "I'm sort of out of words anyhow."

"Georgia," he started, "I don't quite understand what has happened to our relationship, but somehow, when I first met you on Skype, my heart was already yours. Since then it has been as much as I could do to stop embarrassing myself, and when in your company, to stop myself from pulling you toward me and kissing you. You are smart, a great friend already, sexy as hell, and such a gentle lovely person who I have admired without really thinking about it for years."

Now this was quite an admission, I thought, from Tim. Unbelievably honest and forthright and exactly what I would expect having known him for some time.

"I'm not sure this is the time to say it Tim, but whilst we are being direct with each other, you're straight aren't you?" and I immediately regretted asking that question.

After a moment's pause, Tim said, "Yes, I am. Or I was, but what does it matter? What matters is this. This thing that is happening here, in your room. That's what matters."

I was taken aback; I have to admit. And so it seems was Tim. "Look. Gorgeous Georgia. We will both go over this evening many times in our heads, and eventually we will reach some sort of conclusion. What will be will be." Tim said.

"Well I hope this date isn't our last Tim." I replied, trying to be positive about what he had just said.

"I'm sure it won't be," he said and engaged me in another kiss, this time no less passionate, but shorter than before.

"If you change your mind about us Tim, I will understand, and I promise not to end up behaving badly like an ex that you have dumped. But I won't pretend it didn't hurt."

As I felt an overwhelming sadness hit me at the thought Tim realised by the look on my face and pulled me toward him for a long and meaningful hug as I tried hard to hold back some tears.

"You know of course that I have never been with anyone else before," I said, after recovering my composure. "And by definition I am in fact a virgin, in that respect."

Tim smiled, "Of course."

I guessed we both had some soul searching to do, and perhaps more than just a little experimentation too. And I cannot explain the logic behind what happened next, except to say that I had quite a lot to drink that evening and was, not unnaturally, fairly aroused as a result of my first date.

I placed my hand on the front of Tim's fly, and gently felt his erection through his trousers. This was as much a test for me as it was for him, I thought.

"Before you go," I said, "and you really do have to go at some point soon, would you mind awfully if I had a look at the goods. Only so that I might know what to expect next time, if there is a next time? And anyway, as you are straight, maybe, you can decide if you mind or not."

Tim's expression changed and suddenly he became what I judged to be more relaxed, or something. It was hard to explain. But he didn't reply quickly and so rightly or wrongly I took it as a no.

I unzipped his fly but struggled to get him out, his boxers simply getting in the way. Altogether an embarrassing moment during which I was blushing like a 3kW radiant fire. Eventually I unfastened his belt, and with is hands resting on my shoulders I lowered his trousers and boxers to expose his cock.

My heart was pounding its way out of my chest and I began to doubt my decision to take on this momentous task.

As I touched his cock and explored it with my hands as if in a science lab at school exploring some object that one had never ever seen before I felt awkward but excited. Tim remained silent but as I looked at his face his eyes were closed and he was clearly enjoying the experience. To say that I was relieved was an understatement. I had feared he would freak out and leave in a hurry, having discovered that he was, in fact, straight. Completely straight.

My mind wandered for a second as I asked myself if his going with a TGirl made him bi, or gay, or just a straight guy who likes TGirls. I never did reach a conclusion.

I was content that neither Tim nor I found the experience unpleasant. Looking back this sounds silly, but it was important to me. I didn't want to lead someone on only to run a mile once they dropped their trousers!

Whilst it had been my intent to zip him up again it seemed a wasted opportunity as there was a second phase to this experiment that had to be completed. And so I dropped to my knees and very slowly licked the tip of his cock which by now was oozing pre-cum. The taste was different, but not unpleasant and so I set about exploring him with my tongue and mouth, cupping his balls in one hand whilst stroking him with the other.

Whilst I had not given head before, I had received it and had a fair idea of what to do. I knew too that guys found it a turn on if one could take his whole length, although I had never managed to do this whilst experimenting with a dildo. I recalled too that guys liked to watch the girl's face as she gave the blow job.

Tim remained quiet except for noises of obvious enjoyment, and had moved his hands to my head as I moved his cock in and out of my mouth. I looked up to his face and did my best to get all his length into my mouth, but my gag reflex was always going to prevent it.

After a few minutes he became quite noisy and I determined he was going to cum at some point soon. I hadn't really thought this through though and wasn't sure what I was supposed to do next.

A few moments later he gasped, "I'm going to cum!"

I started to withdraw as he came and his load was spread partly in my mouth and partly on my face and so I swallowed as I continued to pump him until he had emptied.

I reached for the tissues on the bedside table and cleaned him up, and as I wiped my face clear, tasting his cum in my mouth, I was surprised how warm it was. I hadn't really expected that.

As I wiped my face he grinned at me, pulling his trunks and trousers back up. This was the first recognition, apart from his obvious submission to my advances, that he had enjoyed the experience.

"Fuck." He said. "That was rather special. Very special. You're good."

I took that as a compliment, but far more than that. Tim and I both realised, or discovered, that we were happy with our sexuality in this particular relationship, and I recall thinking that perhaps he's not as straight as he thought, or I thought.

We sat on the edge of the bed and Tim held my hand, just looking into each other's eyes. Our heart rates were falling and I think we were both deep in thought about what had just happened.

"I'm really sorry Tim," I said, "But I had to know if this thing was going to work out between us. And so it was a test, of sorts. Actually no. Yes. It was a test, but in reality I just wanted you so much and there was no way I could simply kiss you goodnight and close the door. What do you think?" As those words came out of my mouth I thought what a stupid question it was, but it was too late.

Tim squeezed my hand and after a moment replied, "Georgia, I don't mind admitting that you have turned my life upside down. If anyone had asked me if I fancied TGirls I wouldn't have hesitated in saying No. But somehow, from the first day that I saw you, and heard of your story, I knew that I had to get to know you more, although those thoughts did set off a thousand questions in my head about my own sexuality."

Tim smiled and held me close, kissing me on my neck and ear lobes, making me shudder.

"I know that I said that we should take it slowly," he went on, "but this was because I didn't want to rush you. I know how strange this was going to be for you and I wanted you to take your own time. I was happy to let you set the pace." He laughed and said, "You certainly set the pace didn't you?"

I smiled and kissed him gently on his lips. "Such a gentleman," I said, "but next time I think you need to take the lead." And we both laughed.

Shortly afterwards, Tim left, and after showering I slipped on my lovely pure silk nightie and hit the mattress.

The following day, the review meeting passed off as usual and as Tim and I left in the lift together he held my hand and kissed me gently on my lips. I was shocked and caught completely by surprise. OK, I thought, I am wearing some of Georgia's lingerie under my suit, but outwardly I was Peter. Tim was full of surprises.