When I was 9 I had this cute teenage babysitter that my mother hired - a girl from the next block. I think she was about 15 at the time. She had the cutest eyes and curvy body. I was always attracted to her and I'm sure she knew it. Sometimes we would just cuddle up on the couch and watch TV. She would lie back on the couch and I would lie in her arms or she would lie down on the couch and let me lay by her or sometimes on her. I was always a sort of 'touchy feely' type of kid who was always willing to climb the embrace of some girl's arms.
Well one day I was especially frisky and curious. You see, a few weeks prior to this I discovered a couple things: my dad's stash of Playboy magazines and my mom's back massager. Needless to say, I was fascinated with the female form. I tried the back massager. I touched my body with it, but I had no clue what it was for. All I knew is that it tickled. I even tried putting it on my genitals through my clothes, but it didn't seem to do much for me. So I just put it back where I found it.
One day as I was lying with my babysitter, I decided to grab her boob. I had never felt a boob before. Compared to my small hands, her boobs seemed pretty large. Her initial reaction was shock and so was mine. But then her eyes got all goo gooey on me and she asked me if I liked what I felt. I said that yes I did and that I always wondered what they looked like and felt like. I told her I had seen them in my dad's Playboy magazines. She was a curious young teenager herself and asked me to go get one.
We sat there paging through the pictures together. She sat up on the couch while I snuggled up to her side. I had my hands on her legs and I was getting a little bolder. I felt around her thighs while she flipped the pages. She didn't seem to mind this at all. Looking back at what happened, it's pretty obvious to me now that I was making her horny.
She asked me whether or not I wanted to see more of her and touch her. Without any sort of hesitation, I said yes. So she laid back and she said OK - well if you want to see me, you have to take off my clothes.
I guess instincts took over at that point and I went straight for the button on her jeans. She gently grabbed my hands and pulled me on top of her. She said, 'Woah kiddo. Start up here.' And she placed my hands on her boobs. She told me to rub them through her top, and I did just that.
This was really turning her on. After a minute or so of fondling through her top I started pulling it up over her boobs. She leaned up on her elbows to reach behind and unclasped her bra. Then she helped me get her top off. I'll never forget how she smelled. Here I was for the first time looking at a nicely developed teenage girl's body - and I was only in the 4th grade!
She layed back down and told me to take off her pants. So I did exactly that! I had a little bit of a hard time because they were kind of tight on her body but in no time I had her jeans and panties in a bunch on the floor.
She had a full bush of dark brown pubic hair (this was in the late 70's). I wondered why I didn't have any hair and asked her about that. She explained that I would grow hair down there eventually. I was a little bit nervous but she sure wasn't. She encouraged me to explore every part of her body. I ran my hands up and down her chest - on her nipples and down her sides. I tickled her a couple times, which prompted her to tickle me back.
I think perhaps she was getting a little impatient with all the teasing (what did I know? I was only 9). She raised up her legs and spread them a bit. She guided my hand down to the folds of her pussy, which were very moist. She used my hand to masturbate herself at first and then told me to keep doing what she had been doing. So I did. She asked me to put a finger inside her and I did just that!
She was rubbing her boobs and squirming and moaning while all this was going on. Little did I know this cute little teenage babysitter of mine was really enjoying this.
And then I don't know why, but I suddenly remembered the back massager. I said, 'Hey - I've got something to show you.' I went to go get the back massager. When I came back into the room, she was just laying there with the most seductive look in her eyes. When she saw the back massager, she gasped and started laughing. She says, 'Do you know what that is?' I said, 'No, I was hoping you could tell me what it is.' She says, 'That's a vibrator. It feels good.'
I plugged it in next to the couch and sat down by her again. She asked me if I had tried it before. I told her that yes I did, but that it just tickled. She asked me if I had tried putting it on my privates. I admitted that yes I had tried it, but it didn't seem to do much through my clothes.
She said, 'OK well I want to show you something. And well since I'm naked it's only fair that you be naked too.' I was always a sort of nature boy and not bashful about my body so it didn't take much convincing to get my clothes off. By the way, I had been hard pretty much the entire time all of this was going on and it was kind of starting to hurt from being so hard.
So then she said, 'OK lean back.' I followed her instructions. She took the vibrator and put it on the low setting and put in underneath my balls - the perineum area. She said that this would help relieve the tension in my 'private part'. As I sat there in sheer ecstasy, she asked me if I had ever played with my privates before. I said no. She said, 'Well grab it like this.' She took my hand and put it around my cock. And as she kept the vibrator on my balls, she gently guided me to rub my cock. She let go of my hand and said OK - you think you can hold the vibrator and your privates at the same time? I said, 'I'll try.' She said, 'just keep it there and keep rubbing - it's going to start to tickle you and if you want it to tickle more, just turn up the speed with the switch.'
She laid back on the other side of the couch and started fingering her pussy as I was masturbating myself. This was just amazing to me - the sensation of the vibrator, my hand, and watching my babysitter finger fuck herself. She was moaning and squirming all over the couch as she thrust her fingers into her pussy and rubbed her clit. After a few minutes of this, I turned up the switch on the vibrator and I could see that she was speeding up her movements as well. Finally, the tickling overwhelmed me to the point that I couldn't hold onto the vibrator anymore. I turned it off and just sat there. My cock was twitching. And I think she came shortly after that because after going faster and faster, she arched her back, let out a little yelp and then just sank back into the couch.
We both sat there looking at each other's flush and sweaty faces. She asked me if I liked that and I admitted that yes I did like it very much. I was a little concerned about the twitching in my cock, so I asked her about it. She said, 'It's OK - that's what boys do.' And she said that when I was older that a white fluid would come out of me when that happened and that I shouldn't be worried about it when it does happen.
We did a few other things that summer which I'll save for another story. But I'll never forget having my first orgasm with my babysitter.