It was a Friday night in June, me and my friend Brian were at my house, just hanging around. We were bored so decided to head out to a bar or something. When we walked outside I saw that our mother's were on the front steps talking.
"Hi guys," Diane said. She was Brian's mom. "We just finished our walk. What are you up to?" She smiled at me. I had known Diane my whole life. She was now about 55. She had short gray hair, but it was not a recent development. Her hair had been gray as long as I could remember. I always thought she was beautiful. She had bright gray eyes, fair skin and a tall, well proportioned body. She was like 5'7" and 135 pounds. Diane had been in my fantasies since I started having them, and she still is. I smiled back at her before I answered.
"Oh, probably just head out for a couple of drinks."
"If you were good sons you'd take you mother's out for a fun night." We all laughed, and then Brian spoke up.
"Hey, we could take you guys out tomorrow night," he said.
"That sounds like fun," my mother chimed in. Diane looked at me.
"Great, what do you say Jim? Is tomorrow good for you?" I really didn't think that going out with my mom and my friend's mom sounded like a very fun idea, but the rest of them seemed to want to, and I wouldn't want to let them down.
"Sure that sounds great," I answered. Me and Brian left them. We went out for a while, but nothing was going on. By midnight I was home in bed.
***
The next morning I woke up and went upstairs to the kitchen. Mom was already up, making breakfast.
"Hi, Jim," she said. "Time for breakfast?" I had class on Saturdays but it didn't start for a couple of hours. I sat down at the table. We ate in silence. My father was in San Antonio on business, so he wasn't around. When I was done I got up to go get ready. "Don't forget we're going out with Diane and Brian at 8:00 tonight," she called after me.
"I won't," I called back. I got ready and went to class. It was really boring so I was glad to get home. I lounged about for a few hours, and was watching TV when my mother approached me.
"Well, how does my outfit for dinner look," she asked me. She was wearing a dark green turtleneck and black slacks with black low heel shoes. She looked good. My mom is 59 years old. She dyes her hair light brown and and has beautiful twilight blue eyes. She was 5'3" and 130 pounds. Although it covered her completely, the turtleneck was tight around her breasts. Mom has nice full breasts. I would guess they are a C-cup. I also liked the way here pants hugged her body. The dress slacks were snug around the hips and thighs. I had never thought of my mother sexually but I did notice these things. Suddenly I realized I was staring at her breasts too long. I looked at her face. She hadn't seemed to notice. She just thought I was looking at her clothes.
"You look good," I said. "I better get ready too." When I was ready we walked up the block to Diane's house. Brian greeted us and let us in. Doreen was still getting ready. After a few minutes of chatting I heard Diane's footsteps coming down the stairs. I turned to look. She wore a black skirt that came just below her knee, and a white blouse. She also had on black stockings and high heels. I wondered if they were thigh highs. I always fantasized about Diane in black thigh high stockings.
"Are we ready to go," she asked. We were so we left. Dinner was a lot more fun than I would have expected. We joked and laughed. We also drank a couple of bottles of wine. I was shocked to see Mom have three glasses, as she rarely drank. After a couple of hours we left the restaurant and decided to go back to Diane's house. Of course there was nobody there, as Brian's father had died long ago and his sisters had all moved out.
Brian went to fetch a bottle of wine, while Diane and mom sat on the couch. I grabbed a chair on the opposite said of the table facing them. When Brian returned he sat between the ladies on the couch. We talked for a while longer, and everyone got a little more buzzed. At one point Brian told a joke and we all laughed. While she was laughing my mother slapped his leg in mock chastisement. She must've been pretty tipsy because she just left it there, and looked over at Diane speaking. I watched Brian slowly rest his hand on top of my mother's. She quickly looked at him. There was a startled look in her eyes, but something else too. Brian gazed at her a moment longer and then leaned in and gently kissed her lips. At first she didn't kiss back, but she did not resist either. After a few seconds, however, she began to kiss him back. Their kiss deepened. I couldn't believe it. My mother was making out with my friend. I felt like I had to do something. I stood up and was about to speak when Diane walked up to me.
"Relax," she said. "Let's just watch." She slowly guided back in to my chair, and sat on my lap. "Isn't it hot," she whispered turning my face back to watch her son and my mother. They were really starting to go at it. Brian was running his hands all over mom's body. He started to pull up her sweater. When she realized what she was doing, she reached down and yanked the turtle neck off. Next she unhooked her bra, letting her breasts fall free. She grabbed Brian's head and pulled his face to her chest.