First time -might help the nervous part 1

[Arthur]

Hi everybody,

as it is probably the only way I can actually tell anyone about my first time with a Shemale. I dont think I am ready to confide in my wife at the moment so then at least this might set the scene for those thinking about trying this and let me tell my story which I am bursting to share.

To set my background:

I live in the UK, late 40s, happily married with no kids, professional occupation, white and male. I'm far from being a looker, but the years have been kind to me and I keep reasonably fit.......no six pack. Just an ordinary bloke really.

Married for over 15 years, never visited prostitutes, never played around. A one woman guy. Over the years I have enjoyed pornography as a leisure activity and its quite likely you would find me reading a book on Spirituality, Yoga, Therapy, World War 2, Motorbikes etc instead of attending to the internet.

Our sex life is pretty quiet these days, that's a mutual thing as there is a level of comfort now. If either of us want to make love we would, but mostly it's cuddles and playing with each other. I have a few kinks which involve a bit of enema play (we tried it together once or twice, but somehow I prefer to do this alone, I like the buzz it gives me), tried some Catheter play (just me that time as she would have nothing to do with it) and we have bought a strap on which she has used on me a couple of times but she is not very expert.

So where do I sit in the sexual frame ? Well, I like women, particularly young women and bright intelligent women. I like cocks, but not the male body that is attached to it (this is something I began to realise a few years ago and found it hard to understand exactly why that was the case). I would mostly fantasize about someone exactly like me actually fucking me (I know its weird but it was the only way I could imagine being fucked by another guy).

Then I discovered Shemale porn, and no doubt like many on this forum I suddenly wondered what exactly it was doing for me. It messed with my head. Here was what looked like a beautiful woman adorned with a cock and balls. It made me feel slightly uneasy, but there was no doubt that there was an attraction.

Over the course of a year the need began to grow and I just wondered how exactly I might feel going to my grave not knowing exactly what I missed........regret is usually for the things we dont do, not the things we do!
Of course the duality of the situation played on my mind as I realised that there was no way I was going to discuss this with my wife and it smacked of deception and infidelity.

By this time I had selected a possible escort from an internet site. She looked pretty and the reviews were good. It was daunting to realise she was kitted out with a cock that was probably a good couple of inches bigger than mine, although I suspected these credentials were prone to exaggeration.

Another year went by and I began to realise I was going to have to satisy this curiosity regardless of the risks.......oh yeah, the risks! She was not going to be as the description, it was a Police sting excercise to trap punters, I would be robbed, someone would find out, I would get an STD, all those and more....

As it happened I was attending a day conference about 30 miles away from her flat. I drove down to the conference HQ, sat outside in the car park armed with my private mobile phone and a concealed phone number. After sitting, staring at the phone, putting the number in and canceling several times I was at that point you get to on the high diving board. It was now or never and so I dialled. Half expecting no answer or an answerphone my heart leapt out of my chest when she answered and it was a great relief to find she sounded like a female. Nervously I asked for an appointment for later that day, I could hardly think straight, all I could do was mumble through the driest mouth in history. A few second later I ended the call with the appointment booked for after the conference.

The conference felt like it was surreal, I just could not concentrate. It was like being stoned and trying to act normally. My mind was reeling and I kept wondering if I should back out. What the hell was I getting into ? I must be crazy to consider going through with it. The conference was due to finish just after lunch, but was beginning to drag on while I had to keep engaging with some sensible input. I knew that I had to find the place and get some money out (wow, even this had to planned as it would be obvious that the sum had come out of our joint account, so I used my private Egg credit card so that it could be hidden in the costs).

At about 1:30pm I had the money ready, the sat nav set up and was on my way. My mind was whirling with all the things that might go wrong, I was in a daze, excited and scared witless all at the same time.

By the time I arrived it was getting late. Parking up at a local supermarket I eyed up the flat. It didn't look vey enticing and sat on top of a printers shop. Just standing around made me feel furtive and obvious, it was as though there was a sign around my neck anouncing my intentions. I went back to the car intending to see if I could explore some chinks of doubt by phoning to cancel.

I dialled the number and she answered..............