1. Babysitter's First Time


    Date: 2/18/2016, Categories: First Time, Mature, Taboo, Author: brianbigdogsmith, Rating: 100, Source: xHamster

    swallowed hard, nodding and hoping it was okay, that it would be good and he wouldn't hate me because I didn't know how. &#034Good girl.&#034 Charles sighed and he had me lift myself, just a little as he reached down to pull my panties to the side, exposing the plump pink folds of my sex. I was so wet down there, like I'd peed myself or something, but I knew it wasn't pee at all. The air felt cool against my pussy and it was just another sensation for my poor little brain, already much too full with new feelings. I just looked down, watching as Charles moved his penis, the head sliding across my slit slowly, back and forth and making me gasp. It was almost as good as his fingers had been, maybe better except different, I didn't know. But the feeling of his cockhead rubbing my pussy made me want it all the more. I had to fight to keep my body still, like every part of me just wanted to push down and feel it inside. Charles worked the head inside finally, just a little, just enough to split my lips, and then he told me to push. &#034You do it, Jan, just as slow as you want, take my cock, baby...that's it...nice...&#034 I was doing it, like he'd finally given me the permission I'd been waiting for. I just let myself down slowly, letting gravity do all the work as the swollen head of Charles' penis spread my labia wider and wider and then I felt him really entering me and it didn't hurt at first. It was okay and I let myself go a little more and then it did hurt, like a small ...
    pinch. I stopped, hitching a sharp breath and glancing at Charles, but he was smiling and nodding, whispering encouragement. A moment later I was taking more of him, my body taking his penis just a fraction of an inch at a time. The pinch became a cramp, and an ache, and a dull throbbing that got sharp when he'd go a little deeper. My pussy seemed swollen, spread out around him and my soft pink lips were tucked in, as if his cock was tucking my pussy inside of itself. &#034That's it Jan...nice...ohhh...you feel so good...go deeper, girl...&#034 Charles was telling me and his fingers were tightening around my waist, but he wasn't forcing me. I went lower and lower until I suddenly felt something really sharp, really painful, like all of a sudden his penis had become a knife and I stopped, wincing at the pain and I don't think he could have gone any deeper anyway. He was hitting something, hitting the bottom of my pussy, I thought, and there just wasn't anymore room. But I'd only gotten a few inches of him inside me, not very much at all really, and there was so much of his penis waiting. &#034Are you alright, Jan?&#034 Charles asked me. &#034It hurt, right there.&#034 I said. &#034That's all, right?&#034 I wasn't sure what I was asking really, but mostly I just wanted to know if we could stop. We'd did it, a little bit, that was enough, right? &#034It's okay, baby, that's just your hymen.&#034 Charles was smiling at me. &#034Come here...&#034 He put a hand on my neck, pulling my ...
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