Oh, it hurt so bad at first! But I loved it. I couldn'tbelieve that I loved pain. It took a few tries because of the pain. The pressure was so much, b...t I couldn't wait to succeed and have it inside me. If the process of putting it in was so pleasurable, how good was it going to feel once it was inflated? And it was in. The pressure was amazing! I took a moment as the man on the screen sucked on the woman's sex to finger the extra space in my ass. It was so small, but I knew that was about to. He still wanted to meet and he still wanted me in panties. He knew I wasn’t passable and he would have to take his time turning me out. I slipped out of my house on the anointed evening, wearing red satin panties hidden under my boxers. I’d done some ‘manscaping’ so that I wasn’t too hairy and shaved my beard close. I stashed some other items in my car for later - high heeled shoes, fishnets, and tight, tight pants. The bar wasn’t some creepy dive, it was a nice neighborhood bar, and many of. More

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