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Obediently, I followed him. Once there, he produced what looked like a hot water bottle. My mom used to fill one with hot water and put in my bed to keep my feet warm when I was small. I watched, fascinated, as he filled the bottle with luke warm water. "What are you going to do?" I asked."Give you an enema," he replied. "When I take your ass it won't hurt as much if there isn't much in there."My stomach turned over. "You still want to do that?" Yes, Sweetheart."My heart melted when he called me that. He really cared about me. If he didn't, why would he want to make it hurt less. "Well, okay then," I said hesitantly.While we had been talking, he had attached a long rubber tube to the bottle. It had a metal clip in the middle and a little nozzle on the end. He greased the end of the nozzle with Vaseline®. He hung the water bottle on a hook in the wall and told me to lay on the floor on my left side. The tile felt cold against my naked body.He leaned down and lifted my right ass cheek. I rang the door bell, and Tracy answered. “Hi Jesse! What is going on?” She gave me a big hug, I could feel her soft breasts press against my chest and I was starting to get aroused. “Come on in, Jesse and let’s talk.” I walked into her house. “Tracy, I hate to ask you this, but I took a bet with my friend John and lost big time.” “How much money did you lose? I can spot you some if you need it,” Tracy stated. “It isn’t money that I need. I need someone who can help me look like a woman,” I replied. Tracy gave me a funny look and said, “Is there something about you I didn’t know about?” I proceeded to tell Tracy about the bet and how it went from a sucker bet to one that I completely lost. Also mentioned is that I have to dress up starting tonight. Her funny looks changed to one of sympathy then to pure laughter. “Jesse dressed up as a woman! I have to see this.” After Tracy stopped laughing, she finally said. “Okay, Jesse. I have a couple of friends I can call, and we’ll help you.
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