My very first time with another woman
Every summer I used to go swimming at a friends home. We've known each other all our lives and walked in and out of their home without any worries. Since they had a pool we used to hang in the basement, change and run outside. One summer afternoon I walked into the basement and started to change, I did not notice that there were some suitcases and proceeded to get naked. My friends were outside swimming and I noticed that Cindy was there. I walked to the window and peeked out staring at her hot body. With one hand on the curtain and another on my cock I started masturbating. I stroked my cock faster and did not hear the bathroom door open. I guess it must have been five minutes or so when I heard a voice 'humm' to my surprise I turned and noticed an older woman with white hair staring at me and my raging hard on. Embarrassed as I was, the shock of getting caught stopped me in my tracks. She said Hi, I am Charlie's grandma. I said hi and immediately put my shorts on and ran outside.
That evening while masturbating in my bathroom, images of Charlie's grandma looking at my cock ran across my mind and I shot a huge load. The thought of getting caught made me even harder and I came so hard.
The week went by and every time I went swimming I could see Charlie's grandma looking at me. One afternoon I came into the house and yelled hello...no answer..suddenly I heard Charlie's grandma say hi. Charlie is not home he went out with his mom and wont be back for a few hours but you're welcome to swim if you'd like. I said sure but let me run home for my swim trunks. Don't worry I'll give you one of Charlie's she said I'll bring it to you.
I waited in the basement when I heard her footsteps coming down. Here she said you're a little bigger than Charlie but these should fit you, try them on. She handed them to me and turned around as she was going back up the stairs. I pulled my pants down and suddenly I heard her voice...humm I don't think they are going to fit you're much larger in the groin area! I tried to cover myself with the shorts and she said here try them on let me see. I was embarrassed and just froze..come on she said you were not so embarrassed the first day I saw you.
I put the shorts on and they were definitely too tight, take them off she said let me see if I can get you another pair. I pulled them off and handed them to her. Yup you're much larger than Charlie she said. As I sat there naked my cock started to grow and when she walked back down my cock was at full attention. She looked at me and said oh boy! now you're not going to be able to put them on until you come down. So let me ask you she said, how many times a day do you pleasure yourself. Once or twice I said, have you done it today? No I responded. Well go ahead I don't want you to lose that beautiful erection she said. I was so relaxed by the way she talked to me that I proceeded to stroke my cock up and down. Here she said, put some lubricant on it. She pumped some cream on her hand and waited, I moved closer and let her put it on my cock, her warm hand and the cream felt so good. Would you like me to help she asked as she gently rubbed the cream uhumm I said. Come move here. She moved her hand with such experience and she talked softly.
Masturbation is such an important part of a young man's life she said, my kids all started doing it around your age and it's such a healthy thing to do. I could not believe this Charlie's grandma was sitting in front of me stroking my cock and cupping my balls. I was in heaven; boy did that feel good. She continued to cup my balls playing with the head and suddenly I exploded right on her dress. Oh my she said you have so much cum. I started to apologize but she said don't worry! Charlie's grandma got up and came back with a moist cloth and started cleaning my cock. Here you go she said that must feel better. Go on home and have a nice evening. I ran home and after dinner masturbated twice more thinking about Charlie's grandma.
The next day I ran to Charlie's, went to the basement and did not see her, Charlie came in and said grandma left this morning Mom took her to the airport. Too bad I said I was beginning to get used to having her around. Well let's go swimming I said.