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I hold the shaft with one hand and pull aside each ass cheek in turn with the other, trying to stretch him that little bit further and ease my entry. The angle makes it a little tricky, as I have to push up slightly and can’t just add weight to force my way in. I hook my hands over the top of his thighs, keeping him down on the bed and giving me leverage to push into him. I thrust, slowly but insistently, hoping to drive the 2 inch head past his sphincter. Jimmy whines like an injured dog, screwing his eyes shut and shaking his head, but I cannot seem to make progress. I take the gel bottle again, drizzling gel all around the interface of silicone with young, tender flesh and working it in with my thumb. I notice the muscle gives a little more under the kneading of my thumb, and when I’m satisfied that I’ve got all the lube in that I’m gonna I pull back no more than a quarter inch, before pushing forward perhaps only a half, but with all the strength I can muster. Jimmy’s strangled. Other sissies? Do I count as one?Not even a minute to think about that that I get a notification, someone wanted to chat.His username was “Jasper” from what I could tell from his pictures, he was fit, had a dark tonality, hair that reached his shoulders and was slightly taller than me from what I read in his info”Hey there cutie ; )”My heart skipped a beat for a second, I had never done anything with a male before, and I just uploaded pictures of me to this site and now this, man finds me… attractive? All girly like that?And just like that, when I replied I went into autopilot, I started speaking in a very girly way, it just came out like that”Hey there big boy~ Whatcha up to?”Maybe it’s all the repressed feelings that are making me act like this, but regardless, speaking like this was actually kind of fun, the idea of being submissive and feminine to a man like that, real turn on for me”Not much, just really horny, saw your pictures and just had to message you haha”and from then on.
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