“Ok baby, it’s going to hurt a little bit but the pain will go away very quickly,” Mrs. O said preparing Megan for what was about to happen. The... with one thrust, I broke the tension and Megan’s cherry was officially plucked. “Oh crap… ouch,” Megan yelled once I broke through. Megan had some tears run down her face, but began to moan with pleasure. I pulled out and gave her a few seconds to recover, then I slid my dick back into her pussy until I was fully inside of her. That’s when I began to. I’d been through this with Dad four years ago. It was awkward then. This was going to be worse, because it was my Mom.“Good. You know you can always talk to me about these things.”“I know that.” Of course I couldn’t talk to her about those things. No guy could. But I knew what she wanted to hear.“I thought you were, but some other things got me wondering. I know you’ve sometimes watched me when I showered and that you were watching me the other night when I was playing with myself.”Oh my God! I. "Thanks man" I said. "Maybe I will." She watched in total disbelief as I tucked the card into the pocket of my suit jacket. Then she just broke down crying and sobbing and tried to sink so low into the seat that I'm sure she wished the ground would open up and swallow her. I leaned over and pulled her towards me and zipped up the back of her dress. Surprisingly, she gratefully reached both arms around me and hugged me so hard I could hardly breathe. "Oh baby," she said. "I'm so sorry. . My hole resisted despite my efforts to allow entry. He pushed harder and with a predictable sharp pain my ring slipped over his cockhead. His hand covered my mouth and constrained my exclamation. “Fucking hell!” He said as his feet shuffled about to steady himself. It was painful. I knew it would pass and I was quite able to tolerate his size until it did. He paused, I breathed deeply and for a moment remembered the gritty determination Harrison showed as he sat on my cock. I must do the.