As I lined my cock up against her vagina, I had a thought. I had come this far, why not take another chance? I gathered the spit I had in my mouth and puckered my lips. I spit my saliva over her entrance and heard her begin to speak.“Oh, I don’t kno—,” I didn’t give her any more time to think. Before she could finish her sentence, my cock was inside of her tight asshole. Her uncertain thoughts must have turned to pleasure because before I knew it she was moaning and begging for more. I slowly. " An optimist?" If I wasn't, I'd never get out of bed," I told her. "What's a guy have to do to get your phone number?" You mean a guy like you?" Lisa shrugged. "I don't know." It was kind of rhetorical," I said, smiling back. "Will you write to me while we're in prison?" Depends on what I have to trade for stamps." Hmmm..." I frowned at that. "I hate community showers."That's about the time a rattling of keys brought our eyes to the door. I could have used five more minutes, I thought, but it. Anything you need before I crash.”“Nope. You just get a good night’s sleep, darlin’.” She stood on her tiptoes and kissed me on the cheek. “See ya in the mornin’.”“Night.”I heard the shower running as I lay under the blankets letting the tensions of the day drain away. Ten minutes later, Jackie came out wearing a full-length flannel nightgown and disappeared into her bedroom. Tired as I was, I still couldn’t drop off, so I figured a nice easy jerk-off might ease me over the edge. The light went. When the moment passed you leaned forward, my cock still inside your ass, resting yourself against my chest. Your whispers told me how painful it was. When, at last, you sat up, there were tears in your eyes. My concern was met with a reassuring smile and a soft shushing. I stared at you for several minutes after, your beautiful body glistening in the dim light. I didn’t want the moment to end, enjoying the sensation of my cock softening inside your most delicate recess. Still, I knew it must..
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