1. Jenny Learns Her Place


    Date: 3/5/2016, Categories: Crossdressing, Author: tvk3983, Rating: 6, Source: LushStories

    His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh! Ooohhh fuck me good, baby,” I moaned over and over. I'd known Bobby since grade school and had even enjoyed a couple of jack off sessions with him during high school but I'd never thought of him in this sense. When I saw him enter the bar I'd recognized him immediately but it had taken him longer to figure out who I was since I was now dressed as a woman. We were halfway through our second drink and his hand was high up on my nylon clad thigh before I saw the light come on in his face as he recognized me. When he did his hand slid the rest of the way up under my skirt and rested on my panty covered dick. “John?” “Not anymore, sugar, call me Jenny,” I had replied with a smile and rested my dainty hand on the lump growing in his pants. “You know, when we used to jack off together I wanted to do so much more but I was afraid.” “I wish I'd known back then,” he answered and smiled. “I thought you were very cute for a guy and I spent many nights lying in bed and jacking off while thinking about you.” Blushing brightly I replied, “So did I.” After that we danced to a slow song and before it ...
    finished we were kissing like lovers. “I want you, uh, Jenny,” he whispered in my ear, his hand resting gently on my ass. He lead me back to our table so we could finish our drink, all the while his hand under my dress and lightly stoking my hardened little dick. Setting my glass on the table, I said, “We better get out of here before I make a mess.” “Want to go somewhere and make a mess together?” “That sounds wonderful. We can go back to my place,” I told him as he lead me to the parking lot. “Where do you live?” “Same place. My folks died in a plane crash a couple of years ago. I kept the house since the insurance paid it off. Of course I've made some changes, as you'll see.” The changes, which I had become accustomed to by now, were very obvious to anyone who'd ever been there before. “I've got to know, Jenny. How often do you dress up? I mean, on weekends or after work, or what? You know, I've always thought you'd look good as a girl and what I see confirms that absolutely. You look better than good, you look fantastic.” “Thank you, kind sir,” I laughed in response. “But to answer your question about dressing like a woman; all day, every day.” “Really? Cool! More than just the average crossdresser, then. Are you thinking about going all the way?” “Oh sure, I think about that daily but I'm not sure I want that. I mean, if the right man wanted me go that far, I might, but so far I'm not planning on it. Hell, getting breast implants hurt bad enough, I can only imagine what the ...
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