I have had sex with a shemale twice. Only two times in my whole until now. A bit strange. My entire life has been filled with perversities of any possible kind. But what I like most of all, has only happened twice. For you know, shemales are the very best there in my opinion.
These wonderful creatures bring together what I like best of all: an often very handsome and feminine appearance, with or without breasts, and a gorgeous cock. I tell you why this is perfect for me. Although I’m a real and devoted cocksucker – and I’m damned good at is as well – I do not like to kiss and fondle with men. I just don’t like it. I don’t mind licking someone’s ass (although not my top favorite), I love it to be fucked by men, but kissing: no. And that’s why a feminine face and a male waist are just perfect. So, only twice. Both of them were whores and working in the Amsterdam Red Light district. By the way: I do not mean anything disapproving by the word ‘whore’. I love whores and I think that they are very brave women (or men). So: Amsterdam based whores. The first one was a brief encounter. He jerked me off and I didn’t even toch his cock. The second one was heaven. It went like this. In that time I had an office in Amsterdam, nearby De Wallen (Red Light District). My colleagues were on holiday, so I utilized the freedom to dress myself at the office. Red latex stockings, some rings and chains around my cock and balls, etc. And so I went. Initially I was just looking – as always - for a hooker with tigh high red boots. If I would have found her, I just would have gone to her. But nope. I made the whole tour along the canal and through the alleys thee, four, five times. But I didn’t see any whore that attracted me. I almost gave up, but decided that I would take a quick look at a part of the canal where I didn’t come too often, because the red lighted ‘shop windows’ over there were seldom occupied. But not today. A beautiful shemale was sitting on a barstool. I knocked at the door and asked if she could fuck me. Yes! She was a petite South American. Nicely dressed and in the possession of a huge cock. She asked me whether I would suck her dick, which I – stupid, stupid – refused. Allright, no worries. She told me to bent over the bed in the room, put a condom on, added some grease and slided into my narrow male cunt. It didn’t hurt at all! It just was fantastic, I had never experienced such a wonderful feeling. And it made me so goddamn horny. Normally I come quite quickly, but not this time, although the shemale was jerking me off while fucking me. We did a few different positions and each of them was just great. We didn’t speak, she just fucked and fucked. Finally, I was on my back, she was between my legs and her cock went in and out, and in and out. Untill I couldn’t hold it anymore. I jerked myself off and few minutes later I was back on the street again. I had a two hours drive to a friend before me. I arrived late, we had dinner and I almost couldn’t sit upright. My ass really did hurt. I missed the most of our conversation, I just kept on thinking of that fine girly man and how great her cock felt deep inside me.