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Was this an invitation I began to wonder? Perhaps a ploy to escape being spanked and caned, or maybe a flicker of undecided hope that she might encourage me to choose to fuck her rather than face the pain and humiliation of physical punishment. With my imagination taking over I could almost hear her whispering “Please fuck me Sir, I really don’t want to be caned” yet paradoxically wanting to be caned, needing to be caned. In reality Lucy stood silent, the occasional deep intake of nervous. This was a very good feeling he was having and if being a crossdressing boy is what made him feel that way then he suspected he'd be doing it a whole lot more often.Once he was in his black stockings his sister took a look at him, "You need just one more thing to be perfect Teddy. I have a little orange scarf that I usually wear with that skirt and if we tie it around your neck it will cover up your Adam's apple to make sure that there's no way of knowing you're a boy under all that. It felt safe. Despite the way I was feeling that night the 'safeness' gradually broke down my barriers and I felt like I could be honest, just so long as he held me. "Well...I guess I do know, it's silly really, I'm just feeling a bit.....well a bit lonely, not like I'm alone obviously, I know you and them..." (parents) "are here but I mean like the kind of alone where....like...." "You want a boyfriend?" He summed up what I'd been trying to blurt out with ease. "Yea, I guess, It's been a. Mark was confident that he’d jump at the chance but I wasn’t too sure so I asked him in a very light hearted way. Kind of flirty and cheeky without him thinking I was being serious. Well Mark was spot on. My friend said he’d love to join us. We chatted about it over drinks and Mark told my friend that he could see immediately that he was attracted to me. My friend didn’t deny it. I guess Mark and I have a very chilled approach and attitude to things and this means people feel they can be honest.
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