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Old 08-26-2013
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cutboy cutboy is offline
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Red face Discovering shemales: my story

Hi all,

I've been lurking and doing some, um, research on shemales lately, and thought it about time to share my experience!

When I was 12, I was fostered with a family for a few years. I shared a room with one of the boys, also aged 12, but who was more "developed" than me. He wasted no time in introducing me to masturbation, showing me how to wank, and eventually coaxing my cock to its first orgasm etc. He also got me to let him suck my cock, and me to suck his as well. I wasn't as keen on sucking his cock as he evidently was on sucking mine, but I would give in.

Anyway, he was a very slim and delicate featured boy, almost incongruous in his cowboy jeans. Perhaps that's what made me more receptive to these activites, I don't know.

I left when I was 15/16, and lost touch a few months later, and only recently when travelling back in the area thought to see if the family was still there. The mom gave me his number as he'd moved to a city across the country. A few months later, I was travelling nearby, and thought I'd call him up. He answered the phone, seemed a bit surprised when I mentioned his name, but remembered who I was and was happy to meet up.

We arranged to meet in a bar he suggested. After waiting for a while, I saw a slender and attractive girl come up near and was surprised when she sat down opposite me. I thought she had come to pass on a message from my friend. I stared at her face as she smiled at me, and within a few seconds a lightbulb went off and I said "is that you?!" I was rather clueless why he was apparently in drag, and over drinks he explained to me that he was now a she, that he identified as a woman. I had no idea about any of these things and peppered him, now her, with questions! Sadly, she'd fallen out with her very conservative Christian family, and had very little contact for ages.

I did always wonder about my friend after I left there in my teens: was he gay? I thought he must be gay to have been so keen on us wanking, etc. But it turned out he was a shemale in waiting.

I had a just a couple of hours before leaving, so we went back to her place. Before I could do much about it, she had my pants down and was wanking and sucking my cock like old times. She showed me she still had a (working!) cock too!

I have struggled with my relationship to him/her in that I have never considered myself gay, or even bisexual, having no desire to have any sort of sexual relationship with a man, whether straight or gay. I saw our wanking sessions as just youthful experimentation, but somehow I let him get away with things I'd never have considered letting another boy do, which always bugged me since. There was something about him at the time that I found myself receptive to, and having men him>her recently, I realised it was his feminine features and manners, eyes and smile.

I was very confused by all this, and had never paid much attention to shemales before (I'd only seen occasional ad pictures at the back of porn mags of course) having only ever fancied girls. I'd never met a shemale in real life before (knowlingly!) and started looking online for more. I was literally dumbstruck when I saw pictures of Paula Melo, as my friend is almost the spitting image, and found myself falling for her in a big way too. I'd never consider being with another guy, or sucking his dick, but someone with my shemale friend it was different.

As you can tell, I'm still making it sense of it all and very new to this world. I hope I have used all the terms correctly and not offended anyone over my terminology: if I have inadvertantly said a wrong word, I apologize!

Great to have discovered this wonderful forum!
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Old 08-29-2013
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Florian Florian is offline
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Thats so beautiful. Wish it had been me.

Welcome, and feel free to tell us all you want.
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Old 09-27-2013
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cutboy cutboy is offline
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Thanks for the reply, really appreciate it!
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