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My emotions ran from resignation to fear as I felt the head slip through my lips and into my pussy. She was cautious at first, until it moved easily inside, and then she began a more vigorous stroke. Unfortunately, I think the orgasm was tempered somewhat by the knowledge of what was to come. It was good, and it was strong, but not as strong as others she’d given me. She pulled it out and generously applied lube to the dildo, and then to my upraised ass. With her fingers, she worked it deep into my rectum and all around my anus. I didn’t tell her to be gentle. I didn’t have to. I won’t lie. There was some pain, somewhat intense for a few seconds, but I’d had time to prepare for it and deep breathing helped as I waited for it helped me relax. I grunted and cried out when the head popped through and went into me. She waited for me to calm, then began to slowly work it into me with short, firm strokes. It was uncomfortable, but not really painful since she’d pause after each stroke to. ‘If she’s wet and I’m hard it’s all good!’ the prisoner sloganized. She had seen his type before, the posturing jackass. But she would soon break through this arrogant, little persona of his. She stood up and slowly walked the length of the room, making sure he had a good view of all her voluptuousness. ‘Okay, let’s get under way then. Do you remember your first sexual experience?’ she asked. ‘Wow, straight to the sex! No foreplay?’ he joked. ‘You should be used to that.’ she quipped flatly, ‘Now, back to the question. He looked up to the ceiling and grinned. ‘Sure, I’ll never forget it. Mom was a great lay!’ he replied. ‘So you identify sex with your mother?’ ‘Wow Doc! Now who’s getting strange here!’ ‘Where you a momma’s boy?’ He flashed a fierce glance at her and then recovered his smile. ‘As much as you were a daddy’s girl.’ ‘You seem defensive.’ ‘That’s funny, most women find me of-fensive.’ ‘But not your mother.’ ‘Especially my mother!’ he answered automatically before.
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