A few years ago I was downloading porn, and one of the files I *thought* was called "trainee red head" as in, a noob red head girl doing stuff for the first time (I can't resit those red heads lol). Turns out it was actually called "trannie red head" and I couldn't read :P. Didn't realise until I was already watching it and then... she had a cock. I turned it off at first, but after a while I was too curious so I ended up watching it all... and jerking off to it too. Since then I began seeking out more "shemale" porn (or whatever you want to call it... sooooo many names lol).
I've never met one in person (though I would love to), but I have gone on cam with a few on ImLive.com, and recently I've been enjoying going on as their "sissy slave" as they like to call it, where they dominate me and tell me what to do, and I get to put on a pair of stockings and fuck my ass with a dildo while for them. Makes me cum like crazy!
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