Written by Williamstrap

TV
12 Aug 2013


My last time with a shemale was earlier this year.

I was in a Northern Thai city that I had visited before.

On that first occasion I had been for a massage and had chosen a beautiful lady to do the honours. Now not all places contrary to popular belief offer “a happy ending or better” but a good few do. It's impossible to tell which places do or don't.

Anyway this women was beautiful and did indeed give me a happy ending.

A few days later I was standing talking to a fellow countryman in a bar when she walked past. I told him that she had given me a really good massage.

He laughed and told me she was a ladyboy. Now, I am no stranger to ladyboys and thought that I could spot them easily and I argued with him that there was no way she was a ladyboy. That was a pretty fair statement because I had never seen a ladyboy working in a massage place in this city before.

He told me I was wrong, to which I could only reply, well, she still gave me a great massage.

I never went back there for another massage, I did enjoy many more massages at other places though, including one wonderful slim young thing who seemed to enjoy fucking! She didn't even ask, just slipped a condom on and mounted me, the naughty girl. She didn't ask for any extra money, but I gave her a big tip anyway.

A few months later I was lucky to return to that City. I saw the alledged ladyboy outside her massage place on a few occasions but never went in.

On my last night before returning home I was in a bar watching the Formula 1 race when the shemale walked in and stayed chatting to the owner. She did not see me but I saw her. Again I could not believe she was a shemale. Her voice also was not the usual ladyboy voice.

As she left the bar the owner of the bar (an older lady) turned to another man in the bar who she seemed to know and said she was a katoey (ladyboy) but the best in the City, a really good masseuse.

After the race I was a little tipsy and should really have returned to my hotel to prepare for my flight home the next day.

Instead I went to her parlour and seeing she was free I went for a massage.

During the massage she asked me if I wanted any thing else and she was soon stroking my hard cock.

I still did not believe she was a ladyboy, I asked her to remove her clothes, I said I would pay more. She told me we couldn't here as it was not safe, she could lose her job.

She did suggest I could take her back to my hotel when she finished work, I said yes and offered her about 3 times more than the going rate to do so. (I was obviously beyond tipsy!).

I went off to get some food and later waited near her work place for her to finish.

We got on our motorbikes and headed back to my hotel.

Unlike most ladyboys she did not over do the make-up, she had beautiful long luxuriant hair that reached down to her ass and she talked softly.

In my room she asked if she could have shower, I of course said yes and off she went.

She came back wrapped in a towel and soon we were on the bed and I was kissing her and then moving down to her beautiful tits and they were beautiful. Probably a nice C cup, not too big and very natural looking, although she later told me they weren't No big ugly scars to give it away though as they know how to do a rather better job than the butchers who seem to do american porn actresses botch jobs!

Soon enough I had my hand on her crotch and sure enough she had a cock and not a small one either a solid and I do mean solid six inches I would estimate and not too thin. As big as most mens cocks I had experienced.

She made it clear she did not fuck men up the ass, she was a pure bottom. That's a disappointment to me. I don't even enjoy anal sex with women. However I had over a few meetings with ladyboys managed to switch when the occasion called for it.

However, my cock which as I have gotten older has lost it's youthful power and being unused to me being drunk, was refusing to play ball.

I tried but could not get it up. I did not mind to much as I was happily licking her breasts and sucking her hard nipples while stroking her hard cock.

Eventually after numerous failures I apologised telling her I was too drunk to get hard.

However, I still wanted to have my fun with her and I got her to lie over me and fuck my mouth while I wanked myself.

I still could not raise my pathetic cock and so gave up and grabbed her ass, pulling her hard cock deeper and deeper into my mouth. I was almost gagging it was a a very exciting time for me and I loved the feeling of almost not being able to breath. She was enjoying herself as my wettened finger was also pushing at her ass as she thrust deeper into me. I felt her cock harden further and she squealed as she cum in my mouth (in a condom, I'm a pervert not stupid!). She wanted to stay the night and I desperately wanted her to, but I had to pack and leave early in the morning. I thanked her for a great time and showed her the door.

Of course I was more than able to wank my stupid cock to completion before falling asleep.

I have indeed wanked myself on many occasions since, remembering her beauty and the feeling of her cock pulsing in my throat as she cum.

Although not really being into anal sex, I would totally have loved to have fucked her, she was so beautiful. But, hey this is a true story and sex doesn't always go to plan.

Sadly it is unlikely that I will ever get to see her again as I am unlikely to be travelling to that city again for the foreseeable future.

She was though one of the most beautiful women I have ever seen and had the pleasure of and fully aware that she was really a male, I still stand by that fact.


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