Middle-aged woman Stories

The way it began was kind of unusual. My name is Phillip, I'm eighteen, and I live with my mum, who's in her late forties. One day I was in my room, completely naked, in the process of getting dressed. I was standing in the middle of the room, dick hanging out in the open for anyone who came in to see, when the door suddenly opened, and my mum came in with a basket of laundry. Immediately I blurted out, "Jesus, Mum, knock...

Dear Diary, It’s after midnight and I can’t sleep. I’ve become obsessed with Frank. He and I have been having sex almost every day. I know he uses me and he treats me like a whore. I love the danger of being caught when he fucks me. I only have two rules. First, he can’t come inside me. The last thing I need is to get pregnant. Two, no violence. A little spank is okay but, I don’t want to be assaulted. This past Saturday,...

It took me a long time to find Chase. My inquiries into hiring a male escort had to be discreet, especially since he wouldn't be escorting me anywhere except the bedroom. More than once, I thought I'd finally found someone suitable, only to be disappointed upon meeting the man. The frustrating process grated at me; I knew it had to be easier for men who were willing to pay for the companionship of a woman. At almost forty...