An older male baby sitter
Back in the 1950s sex wasn't on my mind at all since I was only about 9 years old.
My mother and her girl friend were going shopping together. So we drove over to her place and mom left us to be baby sat by this womans husband.
We were supposed to be going swimming later so my sister and me had on our bathing suits.
We heard mom and her friend pull away in the car as we sat watching tv under the watchful eye of our unknown sitter.
He was an average build not big at all but older, about in his 40s.
We sat there watching tv together. I would look over once in a while to catch the man rubbing his crotch area and staring at us.
Finally the man came over to the sofa and sat down beside me. I almost felt naked sitting there in my bathing suite. I was small with a slender build at that time. I sat there trying to watch tv but I couldn't help peeking beside me to see him still rubbing his crotch area.
My sister was almost asleep at the other end of the sofa. He noticed this and said he would place her in the bedroom for a nap. Then he returned and sat down right beside me so that I could see him. His pants were undone at the top and his zipper was down.
He reached into his pants and was rubbing what ever was in there. He started asking me if I had a girl friend or a girl I liked. All I could say was no. He then said, but your a good looking boy, they should be all over you.
He then put his arm around me and laughed. He then said, do you know what little girls do to little boys? No I said. Well they have a habbit of playing around and touching you to get you excited.
Then he started to rub my leg and moved up toward my crotch. I started to tense up and move away but he held me tighter. Don't worry he said, I am only going to show you what they do and how good it feels. He started to rub my cock through my bathing suit and had his hand on my bum at the back of me. Actually it started to feel pretty good. He got me to stand up then he pulled my bathing suit down until it lay on the floor at my ankles. Again he worked his way to my cock and gently rubbed it and started stroking it slowly. It was small like me. About 3 or 4 inches as it erected under his touch. His cock was now visible to me as he pulled it out of his pants. Wow, this thing was big. I had never seen a mans cock before but this was big. He took my hand and guided it to his cock. I felt it, it was soft to the touch but it was long and very wide. I could not get my hand even part way around it. Of course my hands weren't that big at my age anyway. I just stroked it up and down like he showed me and sat there enjoying this new feeling.
The man then stood me up and let me kneel at the coffee table with my ass in his clear view. He was stroking my cock with one hand and then started feeling around my ass hole. His finger was probing the hole once in a while and pushing in. he then got something out of his pocket. It looked like a tube of something. He squeesed a bit onto his finger and went back to my ass hole. His probing was a little harder this time. He was able to push his finger into my ass now and was moving it around in circles. This was giving me a pleasurable feeling. My little cock was standing up tall at this point as he still stroked it gently. By this time his finger was moving in all the way into my ass.
He then took up a position behind me on his knees. I felt something much bigger than his finger pushing at my ass hole now. I started to tense up to stop the pushing. He told me to relax and enjoy it. He said he would make me feel even better.
Then he pushed a little harder and I could feel something go into my ass hole. It was like a pop feeling when the head went in. The pain was with it. I tensed up again to get it out. He then pulled it out but was pushing again to get it back in. I could not fight it. I let him put it in again. It hurt for a while but then started to ease off as his cock slid in. I could hear him breathing heavy at this time and was moving a little faster. Then I heard him grunt and he pushed it deeper into to me. I don't know what happened but he then eased it out from my ass hole and was stroking it and rubbing it on my ass cheeks. I felt wet all over my ass. I was kind of sad when he pulled it out but didn't say anything. I felt wetness running down the back of my thighs.
He then stood me up and lead me to the wash room and cleaned me up.
No sooner was that over, we heard a car pull up out front. Mom was back.
I was happy because we could now go swimming, but I was sad because the experience was over. Boy did that ever feel gould. Even though I couldn't cum at that age, it felt good.
I never did tell anyone about it even till this day.
That was the first time.