Babysitter Got My Cherry.

When I was about 9 years old a woman that had been babysitting me since I was born was keeping me one night at her house while my parents went to a party. A thunderstorm came up and it was a bad one. The power went off and the wind was howling. I was scared shitless but Cheryl told me not worry and that the storm wouldn't last but a few minutes and it didn't.

Just before the rain stopped she ask me if I was afraid because the power was off and I said "maybe a little" so she she pulled me onto her lap and wrapped her arms around me. I started feeling better already since I could feel her big **** pushing against my neck. I started wondering what it would feel like to touch them and suck on them. No sooner had the thought entered my head and she started slowly rocking her breasts from side to side across the back of my neck and my little ****** started getting rock hard. She started rubbing my crotch area and asked me if that felt good and I said it did but really I was scared to death. Here I was 9 years old and a 30 year old woman was rubbing her boobs on me and rubbing my hard little **** through my pants. After a couple of minutes and without saying another word she unzipped me and out sprung my hard miniature ****. She lighty rubbed it with her index finger and I was quivering all over partly from fear and partly from wanting to do more with her. She asked me if she could kiss my **** and I said " I guess so". Hell yea I wanted her to kiss it is what I said to myself.

She never did kiss it but after making me move to the couch she pulled my pants down and started sucking me off. I had *********** since I was about 5 years old but this was a first time that I ever had my **** in someones mouth. I had always thought about it and wondered how it would feel. Usually just thinking about a girls ***** would make my **** instantly hard and I would run in the bathroom, lock the door and jack off. I loved jacking off and I did it several times a day. She sucked on my **** a few minutes and then she asked me if I wanted to look at her ***** and of course I said "yes". By now I was a full fledged whorehopper and I was determined to check out my first ***** up close and personal.

She pulled off her pants and sat back down on the couch and I immediately without any further prodding on her part went for it. I nose dived into that ***** which was wet with a slight smell of **** which made my **** even harder. I didn't really know what to do so I just began to kiss down into all that hair. I must not have been doing it right because she spread her legs wider and wider and put her hands on the back of my head and guided me to right spot and said "stick out your tongue and move it around" which I obediently did. Her ***** was so wet I started to worry that I might drown and there was couple of times I actually had to pull my head up to catch a breath. Getting air, which I was needing a lot of at the time because my heart must have been beating about 200 beats per minute, was difficult through that wet ***** hair.

This continued for a few more minutes and she said "my god for such a little kid you sure do know how to eat ***** and I think I'm going to ***". Well she started groaning and wiggling her *** and after a few more seconds she made me stop sucking on her ****. My mouth was actually numb from all the grinding against her ***** and that thick hair so I was kinda glad she made me quit. She said " let me rest a minute" and smoke a cigarette and I'm going to show you something. Show me something? I couldn't think of anything she had left to show me. Maybe there was something a girl had beside a ***** and **** that I didn't know about. Something the other boys in school never mentioned.

She had only smoked about half her cigarette and she dumped it and said "now we'll get down to business". If what we had been doing wasn't "down to business" I couldn't imagine what would be. It was black dark in the living room of her apartment and she lay down on the couch but I could still her and her **** were so much better than anything I had ever dreamed about. I leaned down and started sucking on her nipples and she groaned and said "that feels so good please rub my ***** and lightly bite my nipples which I was more than happy to do.

By now with all the sucking and kissing I had done on on her ***** it was soaking wet and I accidently let the tip of one finger enter her ***** and she said " that's right that's what I want" so I let it slide a little deeper in until it was in as far as I could get it and she told me to put in two more which I did. I started working them in and out. I don't know how I knew to do this but I just did it and she started squirming around and moaning and groaning and then she told me to get on top of her. I climbed on her and my **** just fell into her ***** since it was so juicy and wet. The first ***** I ever put my **** into was "hot" and I mean "hot" I couldn't believe anything could feel so warm and good. I loved it and after all I had been through that night and with all the sucking she did on my **** and all the ***** I had eaten it didn't take but a few minutes for my little **** to ***. It was the most wonderful feeling I have ever had and I knew I loved this woman and that she was mine now. LOL. I felt like a real man and I even asked her for a cigarette and she said "**** that **** you're just a kid and I ain't giving you a cigarette". That brought me down to earth in a hurry.

After pouring us a glass of coca-cola she sat down next to me and said she had to talk with me about something. First she ask "did you like what we did?" and of course I said "yes it was great". Then she wanted to know if I ever wanted to do that again with her and naturally I said "yes". She said "well if you ever tell anyone about what happened tonight I will go to jail and we won't be able to **** again, do you understand that"? I said "why would you go to jail? and she replied "because you are 9 years old that's why so you can't tell anyone". I assured her I would never breath a word to any living soul and I never did.

She was the best babysitter any boy could ever have and I still have a special place for her in my heart. After I was in my early teens and didn't need a sitter anymore I would tell my mom that I was going to the schoolyard to play basketball and I would ride my bike to her house and **** her brains out. I bet I ****** her a thousand times over the years and some days I would ride over there twice in one day. I even ****** her for a couple of years after she got married to guy who was about 20 years older than she was. She was one ******* machine and she is what turned me into a male nympho and for that I'll always be grateful.

matthewquigley matthewquigley
56-60, M
2 Responses Apr 25, 2012

all the other stories have been by girls who were devastated, by their experience, and most have carried their feelings and traumatisation into their adulthood. curious that your experience was positive even tho you were technically molested

awesome story, i was 13 with a 18 yr old babysitter we kissed with me on top. i was humping her leg we had clothes on. sucking her big ****. my first erotic time with a girl, she was drunk i was sober and horny is why i think it happened. She wanted to get naked and **** but i was scared of getting her pregnant. plus my aunt and her hubby was to arrive home at any time. This girl didnt care. so we made out and i cummed in my undies from all the excitment...