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Over time I began having fantasies of shemales, probably because in my mind they weren’t nearly as much as a threat as a real girl when it came to being devastatingly humiliating if my secret was discovered. No matter who was the first to see my tiny cock, I knew that there would definitely be a lot of humiliation, and so even in my fantasies I was becoming submissive. I began to think about the fact that I would only be able to satisfy anyone orally, and so my shemale fantasies slowly but surely involved to include some oral on my part, but it was strongly tied to lingerie and being f***ed into it. All of my sexual release was from internet stories occasionally, and phone sex lines. I moved to Florida in my early twenties. I had moved down there with a couple of friends from home. We couldn’t believe the amount of gorgeous girls that were everywhere down there. It was bikini season all year long and most girls made sure that they looked amazing in their skimpy swimwear. And the. " Mistress pulls me to the edge of the bed and grabs the lube to lather up her cock as she sticks 2 lubed fingers into my ass. I groan out in slight pain and pleasure. As I mentioned in the beginning, I was inexperienced in any anal so I was just hoping to take some or half of her glorious cock. She slides her fingers out and says, "mmh I'm so ready to take this tight little ass." She slides her cock head up and down and slowly pushes it inside. God I am so tight she can barely get her head into my ass. Mistress notices this and decides to just use the head of her cock to create pleasure and pressure on my ass and starts jerking me. I'm in a perfect scenario of pain and pleasure as my balls build pressure. I ask her to fuck me and she shoves slightly more cock into me while stroking me and I bust all over myself in great ecstasy. We both stop and breathe heavily, Mistress brings me a cloth to clean up and offers me a shower. I clean off and can't stop smiling as this was the best I.
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