Being a fifteen-year-old boy babysitter was not very common where I come from. I took the Red Cross training to become a babysitter. I took First Aid and CPR too. I had a small suitcase filled with coloring books, crayons, and such to keep kids busy and out of mischief.
My mother talked a couple of her friends into hiring me when all else failed.
I got a couple of jobs. One was babysitting for a four-year-old boy. It went well and his parents were pleased with my work.
The next one was a six-month-old girl. I had to change diapers, feed her, and give her a bath. I hadn’t really seen a naked girl before so I sort of checked her out. It was easy since her knees were always in her chin when I changed her and her pussy was flattened out. She had pooped all over so I had to open up her pussy to wipe her clean. The bath was okay until she learned to splash. When her parents came home she was sound asleep. The mother asked me about my night, laughed about the bath, and wanted to know if I had cleaned her up real well after that runny messy poop. She asked me if I had opened her pussy up and cleaned inside real good. When I turned red and told her that I had she was pleased.
From them I got recommended for a pair of twins, a boy and a girl. They were thirteen years old and didn’t think that they needed a babysitter, especially one just two and a half years older than them. Their parents presented me as a companion or referee more than a babysitter.
Things were fine until the parents left. Then they tried to see just how much that they could get away with. Basically if they didn’t break anything and get me into trouble it was okay. John only wanted to eat junk food and play his video games on the big plasma screen. That seemed fine to me. Jane wanted to play dress up. That too seemed fine until she came out in one of her mother’s dresses. It dragged on the floor so she had to hold it up and the neckline showed me both of her little tits, nipples and all. Jane didn’t seem to even notice so I just took it all in. She had the first tits that I had ever seen. She tried on a couple more dresses all with her tits showing. I realized that it was on purpose. Jane asked me to help her put the dresses back on their hangers so that we wouldn’t get into trouble. I followed her into her parent’s bedroom. As I was putting one dress back on its hanger Jane took off the one she was wearing. She didn’t have anything on, not even panties or socks. I tried to think of it as normal after all Jane didn’t seem to notice that anything was wrong so why should I?
When I had put the dresses back where Jane has said too, she asked me if I wanted to see her mother’s toys. Sure! Why not! Wow! She had rubber cocks in all sizes. One was as big as my forearm and as long too. Jane picked up the smallest one and said that she could show me how they worked. I watched as Jane fucked her own pussy with it. She would suck it and slip it back in. She had me suck it and stick it in her while she lay back and enjoyed it. So I spent quite some time fucking this cute little thirteen-year-old with her mother’s rubber cock. She scared me when she had an orgasm then she showed me how to finger her clit and give her another one. Then she said that if I eat her pussy out that she would suck my cock. Okay! So I sucked her pussy and I liked the taste. Then Jane sucked my cock. I liked it and she let me cum in her mouth. I had just gotten my very first blowjob. Since it was almost time for her parents to come home she got dressed and returned to the living room and challenged her brother to a game. They were playing nicely when their parents arrived. I got paid, got a nice tip, and was asked to sit again the following Saturday. Sure!
I was looking forward to seeing Jane again. When I arrived the parents left. Again John just wanted to pig out on junk food and play his silly games. Jane smiled at me and motioned for me to follow her. She took me to her bedroom this time and locked the door. She wanted to play something new. Jane undressed and stood before me. She wanted me to suck her nipples. I knelt down and sucked each one until she told me to suck the other one. This went on for some time. She wanted her pussy eaten again and I was all excited about doing that to her. This time after giving her an orgasm she wanted me to fuck her. I just pretended that my cock was her mother’s rubber cock and slipped it in. Then I fucked her good. It wasn’t for very long but it sure felt good to me. Jane seemed to like it too.
Jane was going to clean herself up with her panties but I had seen my mother looking at our laundry and especially my underpants so I said no. Then she was going to use some facial tissue but her mother would see it in the trash. Finally I took her into the bathroom and cleaned her up real good with a nice warm washcloth. Jane liked that and asked when we could do it again. I figured that I could do it again in a little while and that pleased her.
The second time I got that washcloth wet first and took it into Jane’s bedroom with us. We fucked and I cleaned her up. She wanted to do it again just before her parents were to get home and so did I. We just barely got cleaned up and dress when they pulled into the driveway. Jane stayed in her room this time and I sat in the living room with John.
A couple of day’s later Jane’s mother Louise asked me to come over. She wanted to talk. The twins had gone off with their father so we were alone.
Louise sat me down and said that she had smelled sex strongly in Jane’s bedroom after I had left the other day. I froze! She said that she had found one of her dildos under Jane’s pillow. Then point blank Louise asked me if I had been fucking Jane! I didn’t know what to do so I told her the truth and she listened. I told her about the dresses, putting them back, and the dildos. I told her about Jane fucking herself with one, me fucking her with it, me eating her pussy, and her sucking my cock. She told me to continue so I told her about fucking Jane three times the other day.
Louise was impressed with the three times and told me that if I fucked her three times before her husband got home that she wouldn’t tell anyone what I had done to Jane.
So I got to look at my first naked lady. At thirty-four she had nice tits and a hairy pussy. I slipped off my pants and underwear but Louise wanted me as naked as she was, as naked as Jane had been. I fucked her and cum pretty quick. Then Louise sucked my cock hard enough to fuck her again. She started sucking it right away afterwards and I fucked her for the third and final time. No! Once more! So she sucked me hard again. My cock was getting sore from all the fucking but Louise didn’t care. So I fucked her for the forth time. She cleaned me up with a warm washcloth and let me get dressed.
Then Louise told me that I could fuck Jane all I wanted too but that I had to fuck her one more time soon afterwards. I didn’t see that as a punishment.
Soon I was getting calls to baby-sit for ladies that didn’t even have children. Louise had mentioned that I could fuck like a teenager and ladies wanted my services. It paid better than babysitting and was a whole lot more fun too. I could easily cum three times in two hours and sometimes get fifty bucks for it.
Mom knew that my business was picking up and let me baby-sit evenings during the week as long as my grades didn’t suffer.
Soon I had a babysitting job every day during the week and two on Saturday. Mom made me go to church so I could only baby-sit for one lady on Sundays. Two of my ladies were members of my church. They smiled and nodded when they saw me. I smiled back at them.
One day my mother told me that the minister’s wife had requested my services on Sunday morning to help her get things ready for the service. I was sure surprised when she told me what she really wanted. She wanted me to fuck her stark naked on every pew in the church, all fifty of them, one each Sunday starting today.