‘I was wondering if your offer to go riding with you tomorrow is still open.’ ‘Sure,’ I said a little too enthusiastically. ‘Then we should ...et some sleep, don’t you think’ I nodded. Mom stood there for a few moments longer. ‘You made me so proud tonight.’ ‘You make me proud every day,’ I answered and then felt the heat of embarrassment start to rise in my cheeks as I realised what I had just said. Moms smiled softly, ‘We don’t need to start out too early, do we?’ I shook my head and laughed,. Next game was close, but I lost, so Mike said that he gets to tell me what comes off. Lol. New rule as we go, nice eh. So, he spoke out take your bra off and leave your shirt on. I laughed a little ok easy to do so I reached up under my shirt and pulled off me bra and placed it on the pool table. “There.” I lost the next game too, so once again Mike spoke up, “ok now your panties.” I laughed. “Really! Not what I was expecting. Ok I will be right back.” I then went to the lady’s restroom and. So, I set my age filter to thirty-somethings. To be honest, the reason I didn't start with thirty-year-olds, is because I didn't think they'd be interested. I mean, I wasn't ugly, or overweight, but I definitely wasn't in my prime. I had a few wrinkles, a few more pounds, and more than one or two grey hairs, but my figure was still ok, and despite breastfeeding two children, my boobs were holding up well. Still, I was I certain I couldn't compare to the average thirty-year-old, or so I thought.. "I positioned myself on the pile of pillows, with my butt up in the air. He pushed my legs a little further apart, and I braced myself. I knew it was important to relax, but I just couldn't. I knew I was tensed up, and I was sure my asshole was so tight it would take a stick of dynamite to get it open, not a stick of man meat.Here it comes girl, I thought, the penetration you have been both dreading and looking forward to. This was what I considered to be the last step in me becoming a fully.