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After licking her pussy to several shuddering orgasms, and fucking it till it was sloppy and gaping open. I rolled her onto her belly and lubed up my cock. She immediately knew what I wanted and said "No! Please not my ass. Anything but that, please." I took that into consideration as I rested the head of my cock on her asshole. I spread her asscheeks with my hands and lodged my cockhead in her butt. She went ridgid, arching her chest off the bed, her mouth open in a silent scream. She gasped and asked "Oh my god, is it all the way in yet?" I replied with a slightly sadistic laugh that only the head was in. I pressed a few inches into her clenching butthole and she gasped loudly and started begging me to "please, I'm begging you, don't go any deeper", "noo, no deeper, pleeeeease". Fuck that, I immediately sank another few inches into her ass. She was sobbing by this time, and begging for me to relent on her abused asshole. I would not. Not for at least fourty five minutes of anal. She came into my office to tell me about it, and we walked out to examine it. I am not an ogre, I swear, but I was not going to pay for this damage. I said, "Call your insurance company. That's too much damage for me to absorb."Jackie just stared at me. So, I reminded her that she needed insurance to drive my cars and that she'd assured me that she had insurance before taking the first car for her own use But no, she didn't have insurance after all.Standing in my office, I really gave Jackie hell. She'd abused my trust, and now there was a couple of thousand dollars in damage to my vehicles. As she had so many times before, she simply said, "I'll work it off." "Bullshit," I said. "You're never going to be able to work off that much damage." I will if I use my mouth," she said.I know my face turned red and all I could think to say was, "What do you mean?" I think you know exactly what I mean. I will come back here to your office at closing time tonight."I'm sure I did not get.
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She climbed in, and we took off.Her name was Mary, and we started chatting. She was not sure where she really wanted to go. She then asked if I knew any nice guys that were HIV positive. I said that I did not, then asked the obvious question of her.She was indeed HIV positive, and had just gotten out of jail that day. She admitted that she had done 6 months for a minor theft charge, and “was horny as hell” (her words).We drove and chatted, and she was actually very pretty. About 40, with nice brown hair and slender figure. We drove around, then got a bite to eat. There was an obvious attraction there, but I was understandably cautious. After about 2 hours of driving and chatting, I asked if she would go to a motel with me.We got a room, and she went to take a shower. I relaxed on the bed, and she came back wearing a t-shirt and panties. Relaxing on the bed, we soon started to make out. I kissed her neck and shoulders as I caressed her face and hair (I avoided her lips, to bad). I.

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