Sweet Sherrie and Her Mom - Sex Stories

Sweet Sherrie and Her Mom

... doubts about my relationship with her was the chubbiness. Everyone wants the perfect mate, the ideal partner. In my mind Sherrie wasn’t perfect for me, merely decent for me. It wasn’t until I tried cheating on her by dating other women, that I understood how great she really was. Other women tended to either be timid in bed or have some serious bitchiness issues. After a little taste of how other women were it didn’t take long for me to make up my mind about Sherrie. The one thing that really pushed me over the edge was an awkward encounter with her mother. Sherrie still lived with her mother, which I was fine with. It was just the two of them, her father had been out of the picture for over twenty years. So I was sitting in their living room one day, waiting for Sherrie to get her hair done or something like that when her mom walked in. She looked at me and sat down across from me. Sherrie looked really similar to her mother. It was clear who she inherited her eyes and smile from, as well as her abnormally large boobs. After what seemed like hours of awkward staring Sherrie’s mom, Cassandra, spoke to me. “So, Sherrie tells me that you really like her.” “Uhm, yeah,” I said. “She tells me that you are a good titty sucker.” Now this was getting really fucking weird. “Thanks,” I said bashfully, “I guess.” “She says you satisfy her.” “I try.” “Then why is it taking you so long to get serious with her?” “I don’t really know.” “Well if you don’t get serious soon she may just have ...

... to find another man. Do you understand what I’m saying?” “Yeah,” I said, “I’m pretty sure I know what you mean.” I did it. I took the fucking plunge. I was scared shitless to ask her. I made sure the day was perfect, with the perfect meal, the perfect hike up into the hills, the perfect view of the city below as the sun was setting, all followed up with the perfect diamond ring. You should have seen me! Kneeling below this wonderful woman, over 500 feet higher than the city lights, asking her to spend her life with me. “Sherrie,” I said, “Will you marry me?” She looked down at me, her smile as big as ever. “Oh shit,” she said. “I knew this was coming. I can’t say that I will marry you until I share something with you.” That was a bit odd. By this point we knew each other really well. We had talked about everything, our lives before meeting and our aspirations for the future. I was pretty damn sure she had goals that were very similar to mine. Still she told me to wait. I had not considered why she, at the age of 26, had not been already wed. “Well, why don’t you just share it with me now,” I asked?” “I can’t. I don’t have what I need here.” “What do you need?” Sherrie sighed loudly, “Just come to my house for dinner tomorrow. I’ll give it to you then.” Our trip back home was a bit awkward, to say the least. I kept trying to guess what this thing was she needed to share with me. Was it a gift or a secret? I had tried to coerce any information out of her that I could. Instead of ...