Where it happened: Her Place
Langauge: English
Sex: Male
Rating: 5
Category: Straight
I was 16-years-old and my first time was with my best friend’s mother! Yes, an older woman!
For some background, my friend’s name was Charlie. He and I were the best of friends in high school. Both of my parents worked and I spent most of the summer school vacation at his house. They had a pool and our parents got along very well so they suggested that I go there so I could avoid staying home alone all summer. I was all for it as Charlie and I could hang out and spend most of our time at the pool.
Charlie’s mother was Diane. At the time, she was 34. She had Charlie when she was 18 so at the time she was still rather young. Diane had quite the body but since she was my friend’s mother and never really looked at her or thought about her sexually.
Diane was always very fond of me and treated me very well. It never occurred to me then that what happened was going to happen so needless to say I was shocked when it did.
It got started when I was in my high school play. My parents were away that weekend and did not go. I only had a small part and when I was done, I was free to go sit in the audience. I was done right before the intermission. I ran into Diane who waived me over and suggested that I sit with her. Charlie was still in the play so I was going to stay and watch anyway. Charlie’s father was also away that weekend so it was just Diane and I sitting there.
Then, it got interesting. It was winter and it was pretty cold night. Everyone had overcoats and parkas on their laps. Diane placed her coat between me and her so that it basically covered both of our laps. I took no notice and figured that she needed some space since her coat was rather long. It was dark in the auditorium and we were sitting towards the rear where it was pretty much pitch black.
All of the sudden, she put her hand on my thigh. I instantly froze with nervousness. Then she went for my crotch and started stroking me. I got the biggest hard on I ever had! I was very nervous and almost on the verge of trembling. I looked at her and she was watching the play and smiling as if she was just enjoying the show. I put my hand on her hand. I desperately wanted to touch her back but was so nervous that I just couldn’t do it.
The show finally ended. The lights game on and Diane was acting as if nothing happened. We left with Charlie and they dropped me off at home.
Two days later, it happened. I was walking home from school and Diane passed me in her car and hit the horn. She pulled over and asked if I wanted a lift. She would do that if she saw me on the street so it was not unusual. She didn’t mention Friday night and neither did I.
She said that she had to stop by her house and I knew what was going on. She invited me in and I accepted. Charlie had basketball practice which was just starting and her husband was at work and usually wasn’t home until later anyway.
We then talked about Friday. She asked me if I liked what she did. I said yes. Again, I was getting very nervous and I got enough courage to ask her why she did that. She said that she was in a playful mood. Then she asked if I would like to go upstairs with her.
At this point, I am shaking with nervousness and can’t even speak too loudly. I mentioned her husband catching us. She smiled and said she would check on him. She called him and learned that he would not be home until 7 and Charlie had practice until 6 and she was picking him up from there anyway. Satisfied that I would not get caught, I went upstairs.
She knew that I was very nervous and she told me to relax. We went into the bedroom and she closed and locked the door. She told me to undress so I did and so did she. We were both naked and she told me to lie on the bed with her so I did. She asked me if it was my first time and admitted that it was. She said good and she told me to touch her pussy and her breasts. She was very wet and I was getting more and more excited as well as nervous. She touched me as well but I was calming down which was obviously her idea. She told me that she was fixed and there was no need to worry about using a condom.
We French kissed and continued touching. She whispered things in my ear like “I am so hot for you†but she really got me going when she said: “I know you wanted to touch me on Friday. You should have.â€Â
She asked me if I was ready. I knew what to do having seen plenty of porno movies. I got on top and started fucking her. She was moaning and groaning and it felt fantastic. She told me to stop and I was terrified that I was doing something wrong. She then said I was going too fast and she wanted it to last. She got on top and we did it for half an hour before I finally came. She had come several times herself so I was off to a good start.
After that, we laid in bed for a little while. She said that I did good for a first timer and that she hadn’t had sex like that for a while. I got the hint that her husband was not doing a good job of satisfying her cravings! I should mention that her husband was 10 years older than she and they got married when he got her pregnant with Charlie.
She changed the sheets to get rid of any evidence and I stayed for a little while. I had just had sex for the first time and was on top of the world. I finally asked her why she selected me and she only said that I was cute and not too experienced which she found erotic. She said she had fun showing me the ropes and again said that I had done very well for a first timer. I left and headed for home.
I was a bit bewildered but also felt good. Later on, I felt a little bit guilty since she was married and the mother of my best friend but that went away wit time. I figured that I was selected as I would never say anything considering the trouble it would get me into. To be quite honest, I figured that since no one knew, what the Hell!
After that first time, we got together every now and then. It was never planned but sometimes she would spot me somewhere and pick me up and take me home with her. I was with her around 10 times from the first time we had sex until I graduated high school. Sometimes we didn’t do it for months and sometimes a few times a month. It depended on if we ran into each other and if anyone was at her home so it was usually spur of the moment. Diane was a great teacher and introduced me to the joys of oral sex and even anal sex as time went on.
Our sessions stopped when I went off to college. The last time was right after I graduated. This time, it was planned and my graduation present from her. This time around, we got a hotel room and had the best session we ever had. She told me before we had sex that it would be the last time since I was going away to school and that it probably needed to stop anyway. I agreed. It was only a sex thing with her and since, by that time, I was having regular sex with my girlfriend, it didn’t bother me.
To this day, no one knows a thing. Only Diane and I know. Not even my wife knows. Diane eventually divorced Charlie’s father. Interestingly, I recently attended my 20 year high school reunion and Charlie was there. We are still in touch by e-mail but not as close as friends a we were as we live on opposite ends of the country. I asked about his parents and he said that his mother now lives in Florida and said that she asks about me every now and then. I wonder why? Apparently, Charlie suspects nothing. That’s good.
Diane provided me with some great times and some great memories. No one was hurt by what happened between us even though I was a minor at first and she was married. We could have gotten into major trouble so it’s just as well that no one knows and 20 years later, it’s still our secret.
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