’ ‘Why do you think that?’ ‘Don’t make me stroke your ego just to prove myself right.’ ‘I’ll let you in on a secret. Until about six m...nths ago, I rarely left my condo. I was a prisoner of my own insecurities. I’m still fighting those, but Moira, and you, have made a huge difference. So, when it comes to dating experience, I’m probably ten years behind the curve.’ ‘From what Moira told me about Chicago, you’ve been planning that entire time.’ I chuckled. ‘Nah. Planning is just something at. ” She replied. As she tried again to wrap her fingers around the plug she was holding she sighed “I don't know if I can do this one.”I looked at Jenn's face while she imagined squeezing the hard, smooth glass into her anus and shivered a bit. I was picturing it too and felt determined to make it happen, for both her and myself. Our relationship was fairly young so at this point she was unaware that I had already began to explore my own sexual anal desires so I didn't know how to breach the. More

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