Where it happened: Her Place
This story that is similar to Dustin Hoffman’s situation in the “Graduate”.
I was 16 years old and my first time was with my best friend’s mother.
My friend Charlie and I had known each other since we were five years old and we were always hanging out somewhere. During high school, Charlie’s parents took him out of our high school and sent him to a private school in hopes that he would get into a better college. We didn’t see each other as often but we remained close friends.
One Friday night, I was at Charlie’s house as we had made plans to go out. His mother arrived and told Charlie that he couldn’t go out as he had to go with her to his younger brother’s school play.
I didn’t have anything else to do so I tagged along. We got to the auditorium and sat down. Charlie was on my left and his mother was on my right.
During the play, and in total darkness, I felt his mother put her hand on my leg and she started to run her hand up and down. I looked over at her and saw that she was looking straight ahead as if nothing was going on.
I started to get a hard on that began to hurt as my dick was pressed up against my jeans. I covered my lap with my jacket so Charlie couldn’t see what was going on. I liked what she was doing and made no effort to stop her.
The play ended and we got up and left. Charlie’s mother acted like nothing had happened and there was no change in her attitude towards me.
A few days later, I was leaving school and walking home. Charlie’s mother passed me in her car, honked at me, and stopped. She asked me for a ride and I accepted.
She drove and not a word was mentioned about the previous Friday. I thought about bringing it up but I chickened out.
I noticed that we weren’t heading for my house and instead we were heading for her’s. She asked me if I could help her move a few things at home and I told her I could since I knew that we would probably be alone there and that I might get a little action.
We went into the house and I immediately realized that no one was home. I was excited yet very nervous since I had not yet even touched a woman’s pussy in my life.
His mother, her name was Claudia, gave me a lot of hints as to what was going to happen. She said that she was going to change and told me to wait in the living room. She then called me upstairs.
She was calling me from the spare bedroom and I found her in there wearing a pair of tight shorts and a tight t-shirt.
She told me to close the door which I did. She then said the following: “You liked what I did on Friday, didn’t you?” I nodded.
She asked me if I was a virgin and I told her that I was. She asked me if I wanted to have sex with her and I told her that I did.
She told me to take my clothes off. I did and I revealed to her my hard-on. She smiled and said that for a 16 year old, I was well equipped.
She stripped and revaled a very nice body. She was around 38 years old and looked good.
We sat on the bed and she began to caress me and started to stroke my dick. I tried kissing her but she wasn’t interested. I tried touching her pussy but she led my hand away.
Finally, she put my hand on her pussy and told me to stroke her gently. I did and I felt her wetness and it felt great.
She then got on top of me and guided my dick into her. Then she sat on hit and began fucking me. It felt great and it was much better than jerking off!
She stopped and told me to get on top of her. I did and started fucking her. The whole time, I squeezed her tits and sucked on her nipples. She was going wild.
I felt myself approaching the moment of truth which I had done jerking off many times before. I kept pumping her as she squeezing me and I began to yell louder and louder.
I told her I was about to come but she grabbed my ass by the cheeks and wouldn’t let me out. I came inside of her and Claudia came at the exact same moment.
After a little while, she told me to get dressed as Charlie would be home soon. I did and left before anyone else had arrived. I walked home with a strut in my walk since I had finally gotten a piece of pussy.
Two days later, Claudia was waiting outside of the school. She told me to get in her car and we drove to a park. She told me she was worried about getting pregnant since I had let go a huge load in her.
My heart thumped as I began to think about what would happen. Claudia told me that if she had gotten pregnant, there would be no other choice but to abort the pregnancy since the truth would ruin both of our lives.
A few weeks went by, and she got her period. We then began to see each other from time to time at a cheap little motel usually once a week. She would park her car in front of the room that she was waiting for me in.
We would get together around once a month unapades”. After I graduated from college, I ran into Claudia in a bar and wound up going back to her place for a little “nookie”. She had gotten older and it wasn’t as good as it had been before.
We had breakfast the next day but there was no mention about seeing each other again. We never did and I don’t know what became of her.