Lana: First Encounter

I fuss with the wine after she finds the corkscrew and she hunts down some glasses. The apartment is sparsely furnished but comfortable and there is straight porn playing on the flat screen TV. I am not that excited about the straight porn – a beautiful blonde giving head – but it does get me thinking. There is a couch with a coffee table in front. She brings the glasses and I pour some wine. ‘Cheers!’ I say and take a larger than normal sip. I am still nervous and I can feel the wine warm my throat and I begin to relax….

We make small talk for a while. She works for a small accounting firm and is divorced. I explain that I have my own business, am separated. We have similar interests and we talk a bit about our history. She had her first experience with a guy as a teenager in a shared room on a trip and coincidently had been dressing discreetly at home for years. Her interest had never been discovered and she ended up marrying thinking that it was the thing to do. It hadn’t worked out, even though she viewed herself as ‘bi’, things never panned out. She was much happier on her own but actually seeking out a male companion who would meet her as a transvestite was something new. The CL post that I had seen was her first venture out into the world of ‘Casual Encounters’. She wanted a regular thing and had no interest in multiple partners. As well, it was clear that she had two lives, one as a straight accountant and the other as the attractive sexy transvestite sitting beside me.

I had to admit that I was a CL ‘Casual Encounters’ junky – although, there were seldom ‘women’ that posted that interested me or were interested in me. ‘35 and under’ seemed to be the big stumbling block for me. In the back of my mind I kept thinking that if they would only spend some time with an older guy they would come to appreciate the patience and life experience they typically offered. Realistically, I wanted a regular arrangement as well. It was just hard to find the right person.