My first time with baby-sitter

Note : This story is completely fictional!

I live in a town in U.S.A with my family. We are a well to do family and we have a big ship-building business. I also have a sister who is younger to me and really is a scamp. To manage her Mom engaged a baby-sitter – a female baby-sitter (a rosy-nippled baby-sitter). We had her since I was in 5th grade and my sis was in 1st grade as my mom was a working lady and the Amy (the baby-sitter), in addition to baby-sitting my younger sister cooked for me. In this story she is the main character. She was our neighborhood girl and I knew her well. She was a very a sexy and attractive girl and used to wear a dress with a plunging neckline in short, provocative dresses and whenever she used to bend over to pick up something from the floor of the house, her brassiere would come into view and I could see her humongous boobs. 

When I was in 5th grade, I was still very naive. One day when I asked her what those big globes stuck to her chest were, she blushed. She said that those were her globes. I and the Amy were rather friendly so she would never object if I asked her such questions or if I touched her boobs. Sometimes I would touch them and feel their roundness. At such moments she would let out an audible gasp more like a moan and would half-heartedly tell me not to do it. I would fell something hard in my groin whenever I touched her boobs and I would experience a strange feeling. Later on I came to know it as lust. As I grew older I learnt everything about sex and I used to get pretty ‘excited’ on remembering what used to do. But I never realized that knowing and doing all this would change my life drastically.

When I was in 9th grade, this incident took place. Any way let me introduce myself and Amy. I am a kid in 9th grade, about 5”8 tall and a muscular guy and the babysitter is about 6 years elder to me, has good and round boobs and a perfect hourglass figure and had very rosy nipples. I knew she had rosy nipples as one day when she was changing her dress in my room I ‘accidentally’ walked into the room and saw her. The night I saw her boobs, I had my first orgasm. She was always friendly with me and as I mentioned before, she would say nothing when I would touch her boobs even when I was in class 7th, in fact she would close her eyes and smile dreamily.

By the time I was in 8th grade when I saw her naked I had my first orgasm. I was a red-blooded teenager having all info about sex. This vacation my mom and dad were going to Shanghai for a business deal coupled with a vacation. They were planning to take me with them too but I opposed the plan as I didn’t have any interest in going to Shanghai. So my mom & dad decided to leave me and my younger sister in the care of Amy who would cook for me and would baby-sit my sis while they went to Shanghai. I was more than happy for I could now see “good” movies of my own choice without having to bother about anyone!!!

My mom and dad left for Shanghai on Saturday and I was free from Sunday. On Sunday morning I woke up at 8:30am. Amy was already in the house taking care of my sis. I got ready in half an hour and I started to surf the net. I went to a search site and I searched for nude pics of Pamela Anderson and some more sexy celebs and porn-stars in real hard-core action. I love to see pics of round and firm boobs. I started seeing the pics and at the same time I started jerking my dick. My dick was a good 7.5 inches long and about 5 inches thick when hard. Just then Amy came in and saw me with my dick in my hands. The sight of it transfixed her. I noticed her and on purpose, lewdly faced her and asked her innocently if she wanted anything. She was still staring at my dick. 

She mumbled something and went out of the room. She was feeling very horny lately as she had broken up with her boy-friend. I had seen her stealing peeks in the past few days at my hardening dick whenever she would wear miniskirts. The day before she even brought a dildo and pleasured herself in the bathroom. I could hear her moans through the door and that night I dreamt myself fucking the hell out of Amy. Suddenly on observing her discomfort on seeing my dick, I had a brainwave. I decided to observe Amy’s boobs. I reasoned seeing real boobs would turn me on more than seeing pics of boobs. I left the computer and went into the living room where she was entertaining my younger sister. L’il did I know that this would lead me into losing my virginity with Amy.

I went and sat on the sofa from where I had a clear view of her boobs. Then she bent down to take a toy and lo behold!!! I got the sight of my life. She was wearing a thin see through brassiere through which I had the most generous view of her boobs save the nipples. I was just transfixed. She could have put Pamela Anderson to shame by her humongous boobs. Then, she saw me staring at her boobs and then she gave a sexy smile. After putting my sister to sleep she came near me bent down and tried to seduce me with her seductive behavior. I could see the top portion of her boobs very clearly. My dick was raging to get out and it had formed a visible bulge. She asked me seductively what I was looking at.

When I told her I was looking at her globes, she blushed. She started to seduce me by asking if her ‘globes’ were big. She asked me to feel them and tell her how they were. Oh man!!! I thought I was the luckiest guy in the world to have such a slut for a baby-sitter. I put my hand on one boob and for the 2nd time in my life I touched real sexy boob flesh. I felt its roundness and innocently asked her what the pointed thing on her boob was? I pinched it and she closed her eyes, smiled and moaned in pleasure and told me continue doing it. I decided to now play my own game. I told her that I could only judge her boobs if she took off her shirt.

She was so turned on by my pinching that she almost ripped it off, undid the bra clasp and in an overt display of her jugs, she held them in her hands and told me to squeeze them hard and lick the both the boobs. She was just looking like a porn star. I now told her that I had a problem in my boxers and without preamble I took them off. She was stunned for a moment seeing the size of my dick and its thickness. I realized that if I used my brains and my one eyed 7.5 inches long monster properly, I could make her beg for my dick in her. I had a golden opportunity to fulfill my childhood dream of doing Amy. She started begging me if she could touch it and feel it. I decided to dominate her and told her that if she wanted to touch and feel my 7.5 -inch hard cock, she would have to lick her boobs and bring herself to a climax. 

She readily sat down on the sofa and spread her legs wide open and started pinching and licking her boobs. I was surprised that she actually agreed to do what I said and then I realized that she was very horny and would do anything for my dick in her. I could notice some dampness in her white panties. I got so turned on that I involuntarily started jerking my dick. Very soon her breathing became shallow and she started screaming and shook like a leaf in a storm!!! After her climax I saw through her skirt, damp patches on her panties and some pussy juice dripping down her inner thighs. I said, “Well, ya slut. You have earned your reward. But tell me, does your ex-boyfriend have a big cock?” She replied between moans “No! Tom is nowhere as hard or as thick as you.” I continued making small-talk with her so as to tease her. At one point her condition was so pitiful that I at last offered my cock to her. As quick as lightning she jumped over to me and started feeling, pressing and jerking my dick.