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“I want you to lift your skirt up Jessie, and sit on me. I want to take you tonight. I want to be the one that completes you and makes you a woman.” I went and got some lube to place on his penis as he was big, and I wanted to enjoy it and not fight discomfort. After applying lube on him and some at my entrance, I did as he asked. I lifted up the skirt just enough so I could straddle Dan. I stroked his penis several times to get it hard again, then I slowly lowered myself onto him. There was resistance as the tip of his cock pushed up against the ring of my anus. I kept lowering myself down until there was a release followed by some pain and then finally pleasure. After a minute of adjusting to the new sensations, I slowly started to ride Dan’s cock. I felt so full and elated that I finally knew what it was like to be a woman. I could feel the contour of his cock as it slid in and out of my backside. While I was riding him, he lowered my lips to his and we resumed our passionate. One shouting at the excitement I felt and the evenings of this strange new lifestyle that I’d just set in motion.My answer having been given, both Jill and I seemed distracted and unable to return to more mundane topics. Both of us seemingly relieved to end the call so we could be alone with our thoughts. Jill’s smile sweet but a little distant as she told me she’d ring me tomorrow.Actually, she said that ‘they’d ring me tomorrow.’ And even this little change stuck in my brain. In the same way, the thought that I’d not see Jill for another eight days stuck in my brain.It was going to be a long eight days. An agreement and experience that moved our new lifestyle into a new league. We’d dipped our toes a few weeks ago. Jill’s solitary night with Daryl had then felt like the deep-end. But this was the forty-meter board. Scary as shit but with thrills to match. At least, that’s what I told myself.Knowing their itinerary, I knew I’d just agreed to only see Jill twice for three truncated.
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