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By Friday I was saddened that our time together for our little sessions would soon be coming to an end. I assumed that, as she’d been good all week she would not be getting punished at the weekend and that my services as healing masseuse would not be needed. I tried to make it a little more special than before. I found out, as much by accident as anything else, that she enjoyed having her arsehole played with. I’d tried putting a finger up my own while masturbating a couple of times and found it a pleasant experience. It seemed to heighten the pleasure of my orgasm, so I could see why Sherri liked it. I had even got to the point yesterday when I had poked a finger in it and she inadvertently moaned. I tried to make out it had happened by accident. Today was going to be no accident. After I’d spread the ointment over her bottom I let my hand trail down the cleft and stopped at the little pucker. I felt Sherri sway back against my hand, so I extended one finger and pushed it slowly and. I asked if she could take off her clothes but she said no. So i made my hands up her tight shirt and grabbed at her tits. I pulled up her shirt slowly and exposed her breasts. I really wanted to suck on them but she didn't let me. I then moved my hands towards under her laggings and grabbed a handful of bare ass. I moved my hand towards her ass and tried to get a finger in there. I felt her clinch her ass, not letting my finger in. I grabbed some oil from my stomach that she was applying to my dick and went back under her leggings. I had my middle finger ready to get in her ass as soon as she stopped clinching it. Finnaly she let go a little and my finger penetrated her. I had my whole middle finger in her ass and kept it there. She tried to move away but given I had my finger in her ass she couldn't move far. She had been jacking me off for about 10 minutes. And said I need to finish. I said ok and started to finger her ass hard. She moaned and jerked harder. I got my other hand.
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