I'm interested in what first attracted you to shemales. I don't mean your first experience with a shemale escort, but instead I mean your first thought or experience that made you realize this might be an interest for you.
There were two experiences that first made me interested in shemales.
The first was a few weeks before I got married 15 years ago. I decided to have one last fling before I got married, and wanted to visit an escort. (Of course, it turned out not to be the last time, but that's another story.) I have a rule about never picking up girls on the street, and only visiting escorts who offer an incall service and run ads, to show they're profesisonal and not likely not under control of a pimp, etc. But this one time I broke that rule, because coincidentally on the very evening I decided to visit an escort, I happened to be driving on Jarvis near Wellesley in Toronto, and lo and behold there was this petite very pretty young woman strutting her stuff. So I pulled over and asked her to hop in.
I took her back to my place, and we got down to business. She seemed mostly interested in performing oral on me, but seeing as I was about to get married I wanted a more complete experience. When I became quite insistent that I wanted to go the whole way, "she" confessed that she was not anatomically female, and appeared worried that having found out this "secret" that I might become angry.
I was very surprised but thought it was quite funny and wasn't angry at all. I then decided this was a great chance to try something I would not have deliberately sought out, so I reached down and grabbed hold of this large erect cock that was now sticking out from this petite lady's panties. I wasted little time going down on her and we were soon engaged in a hot 69 session, alternating with her on top or me on top, each of us enjoying licking and sucking the other's raging hard on. I am quite well hung and was surprised that she could swallow me the whole way, which made the experience extra exciting.
In the end I topped her for a while, but we both finished from mutual oral sex. and it was great. I "chalked it up to experience" and thought I'd likely never do that again.
About seven years into my marriage a certain boredom set in (the classic seven year itch) and I started spending a lot of time looking at porn on the internet. One day I came across a very erotic photo of an extremely convincing and beautiful lady with a large erect cock. In this photo, she was well dressed and lying back on a marble floor in a luxurious palace-type environment, with a good-looking young man licking her cock. I didn't know if the photo was genuine or "faked" since the woman was so totally convincing and beautiful. (This was before I had more experience and learned there really are such beautiful creatures out there.) Anyway, I got off on this photo, and saved it to my hard drive, where I looked at it from time to time.
That internet photo got me thinking, and I started an informal mission to find such a lady in the real world. I quickly discovered ads from such women in Now magazine and Eye weekly, plus certain websites like LadyPlus.com I visited about a dozen shemales the following year. I got ripped off a few times, and a couple were disappointing (looks, attitude or both). But I also had some great experiences and have been a shemale enthusiast ever since. I have been with some of the women reviewed on this board in the past and will add some reviews in the near future.
So, what was your first experience or thought that got you started in the shemale scene?
There were two experiences that first made me interested in shemales.
The first was a few weeks before I got married 15 years ago. I decided to have one last fling before I got married, and wanted to visit an escort. (Of course, it turned out not to be the last time, but that's another story.) I have a rule about never picking up girls on the street, and only visiting escorts who offer an incall service and run ads, to show they're profesisonal and not likely not under control of a pimp, etc. But this one time I broke that rule, because coincidentally on the very evening I decided to visit an escort, I happened to be driving on Jarvis near Wellesley in Toronto, and lo and behold there was this petite very pretty young woman strutting her stuff. So I pulled over and asked her to hop in.
I took her back to my place, and we got down to business. She seemed mostly interested in performing oral on me, but seeing as I was about to get married I wanted a more complete experience. When I became quite insistent that I wanted to go the whole way, "she" confessed that she was not anatomically female, and appeared worried that having found out this "secret" that I might become angry.
I was very surprised but thought it was quite funny and wasn't angry at all. I then decided this was a great chance to try something I would not have deliberately sought out, so I reached down and grabbed hold of this large erect cock that was now sticking out from this petite lady's panties. I wasted little time going down on her and we were soon engaged in a hot 69 session, alternating with her on top or me on top, each of us enjoying licking and sucking the other's raging hard on. I am quite well hung and was surprised that she could swallow me the whole way, which made the experience extra exciting.
In the end I topped her for a while, but we both finished from mutual oral sex. and it was great. I "chalked it up to experience" and thought I'd likely never do that again.
About seven years into my marriage a certain boredom set in (the classic seven year itch) and I started spending a lot of time looking at porn on the internet. One day I came across a very erotic photo of an extremely convincing and beautiful lady with a large erect cock. In this photo, she was well dressed and lying back on a marble floor in a luxurious palace-type environment, with a good-looking young man licking her cock. I didn't know if the photo was genuine or "faked" since the woman was so totally convincing and beautiful. (This was before I had more experience and learned there really are such beautiful creatures out there.) Anyway, I got off on this photo, and saved it to my hard drive, where I looked at it from time to time.
That internet photo got me thinking, and I started an informal mission to find such a lady in the real world. I quickly discovered ads from such women in Now magazine and Eye weekly, plus certain websites like LadyPlus.com I visited about a dozen shemales the following year. I got ripped off a few times, and a couple were disappointing (looks, attitude or both). But I also had some great experiences and have been a shemale enthusiast ever since. I have been with some of the women reviewed on this board in the past and will add some reviews in the near future.
So, what was your first experience or thought that got you started in the shemale scene?
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