I was 15 when I started babysitting Jennifer. Jennifer was the only daughter of a single mom living off divorce money in thesuburbs . Jen’s mom was starting to date again, so she needed someone to watch Jen when she went out at night, and since I lived next door at the time I was the logical choice. By no means was I a good looking teenager, just average, but Jen on the other hand was cute. At nine years old it was obvious that she was going to grow up into a knock-out, she was a cute kid. Her long, blond hair topped her wiry, tanned frame.
Because it was late at night when I would watch her, I had to put Jen to bed. She had these pajamas she wore to bed that were tiny shorts and a little tank top, and she always changed into them in her room quickly and quietly. We’d sit around for another hour or two watching television before I would send her to bed. By that time she was always really tired and would go to bed without a problem.
One particular night she and I were sitting on the couch watching television, she had changed into her pajamas already, and I looked over to see if she’d fallen asleep (she’d been quiet for a while). Jen was still sitting there, leaning against the arm of the couch, watching tv. The position she was sitting in had caused her pajamas to shift, and I had a clear view up the short leg of her shorts. Her tiny pussy was just barely visible, not even a hint of hair on it, her pussy lips sticking out poutingly.
I shifted uncomfortably as I got instantly hard. My shifting caused Jen to look over at me, and I had to move to hide my erection from her. I wasn’t sure if she was seen or not. She shifted her position, tucking her legs up under her. Thankfully I couldn’t see up her shorts anymore, but the vision kept running through my head. We stayed up a bit later than normal because I was buying time for my erection to go away. After it subsided I got up to take her to bed, but she’d already fallen asleep on the couch, so I picked her up and carried her to bed. I put her in bed and stood there for a minute looking down at her body, her perfect skin barely concealed by her pajamas… and I started thinking about pushing her shorts aside to get a peek.
Getting out of the bedroom quickly took over my mind, and I found myself in the hall with a raging hard-on again. I went back to the living room to take care of my erection, but I couldn’t find anything on tv to jerk off too. Sneaking back into the master bedroom I searched through Jen’s mom’s stuff looking for some kind of porn. In the nightstand by the bed I found some magazines and used those to masturbate.
The following week I got to babysit again, and soon Jen was wearing her favorite pajamas again with the short shorts. Strangely Jen wanted to go to bed earlier than normal, but I obliged by getting her into bed. As she was slipping under the covers I got another peek under her shorts, her legs were spread as she flailed herself into bed, and that same loose leg stretched to the side to give me my view. Again I had an instant erection, and I had to do something about it. I left Jen in her bed and snuck back into her mom’s room. The magazines hadn’t been out for more than a minute when I heard Jen sneak into the bedroom behind me.
I almost jumped out of my skin. Here I was, my hard cock in my hand, stroking furiously, pictures of naked women and men in all kinds of positions spread out before me, and my neighbor’s nine year old daughter behind me. “What are you doing?”, she asked.
“Nothing… nothing…”, I stammered out while trying to shove my cock back into my shorts. It was almost impossible, trying to hide the magazines, get my dick put away, and keep it all hidden from Jen.
Too late… she had moved up right behind me, she was looking over my shoulder… she could see everything. “My mom’s magazines”, she said. That surprised me that she knew about her mom’s stash of porn.
After successfully shoving my dick into my pants I turned around to Jen. I had to make sure she wasn’t going to tell her mom what I was doing. So Jen and I talked for a while, and it turns out that she knew a lot more about sex than I figured a nine-year-old would. While she almost knew as much as I did she was curious about learning more. I wasn’t going to have any more of it, I was trying to end the conversation, but she was too savvy for that. “If you don’t teach me more about sex then I’m going to tell my mom what you were doing”, she threatened.
She had me backed into a corner and I didn’t know what to do. Jen spoke up though and got me out of my stasis, “I want to watch you do that again”. I hesitated. “Pull your penis out again, I want to see it”, she commanded. Since she had found me earlier, my cock had never gone soft. Stunned at what she was saying I couldn’t move. Jen reached over to me and grabbed the button on my jeans.
My shock continued, I sat helpless watching her small hands unbutton my jeans and work my zipper down. When she finished with the zipper she sat back and stared at my cock bulging against my underwear. Her eyes were wide and now she was not moving either. I kneeled, grabbed the edges of my underwear, and lowered them to my knees. My hard cock bounced free in front of me and Jen’s eyes widened further, she wasmesmerized.
Neither one of us knew what to do at this point, but Jen reached out with her small hands and touched my cock lightly. I jumped, my cock jumped, Jen jumped. It was obvious she was curious but unsure so I reached down and wrapped my hand around my dick. She sat enthralled as I began jerking myself off. I was watching her watch me run my hand up and down the length of my cock.
It only took a minute before I was about to cum, the whole experience was turning me on more than I’d ever been; I had to stop. When I did she looked up at me, confused and a bit upset, “Why did you stop?”. I explained that if I continued I would ejaculate and things would be over. “I want to see that”. “What is that called?”, she asked.
I explained and she said, “Yes, that’s it. I want to see you cum. I want to see a boy cum”. The way she was talking turned me on more and I started stroking my dick furiously. In less than a minute I came. It happened so fast that I had completely forgotten about getting some tissues to catch my wad. Jen had been sitting on the floor in front of me only a foot away and my cum blew onto Jen’s hands which were folded in her lap, some spilled on her legs and her arms. I’d never cum so hard in my life.
I was coming off my high when I noticed that Jen was sniffing the cum on the back of her hands. Before I could say anything she stuck her tongue out and licked some into her mouth. “Mmm… it’s sweet”, she said. Amazed, I watched her lick the rest off her hands, forearms. She scooped the cum off her legs and then sucked it off her fingers. “Can you do that again?”, she asked. I explained that I needed a few minutes to get worked up again, my cock was already going soft, and that it would help to have something to stimulate me.
“Something like the magazines”, she said pointing to the pile by the bed. I nodded agreement. Jen grabbed one of the magazines and flipped through it, stopping on two pages of all pictures. The pictures showed a blond woman sitting on a man’s face, his tongue extended toward her pussy, her hands were on his cock and balls. “This is my favorite”, she said looking at the pictures. “Why is he doing that to her vagina?” I explained that it’s called a pussy, and then explained that why he was doing that.
“I think I’d had an orgasm”, she exclaimed. “A couple weeks ago I was rubbing against the blanket in bed and it felt really good. I want to try again and you tell me if I have one”. Jen put down the magazine with the rest and went into her bedroom, I followed. She stripped off her pajama top, her chest perfect and flat, and I found myself getting hard again. But when she stripped off her shorts my cock sprang to life completely. There she was, completely naked, her tight nine-year-old body exposed. I couldn’t take my eyes off her body, her skin looked so touchable as she climbed into her bed. She shoved her covers aside and laid down on the bed, wrapping her body around the comforter.
She started wiggling against the blanket, holding it in her hands and rubbing it between her legs. I started stroking my cock while watching Jen, seeing her rub her tiny cunt against the blanket was so erotic. For a few minutes I enjoyed myself, and while it was obvious that Jen was enjoying herself she was not cumming. I told her she wasn’t going to have an orgasm doing that and she said, “Then we have to try something else, I want an orgasm. Do to me what the guy in the magazine was doing”.
I didn’t know what to do, I knew that was way beyond the bounds, but my hormones had me past the point of reason so I immediately laid down on the bed next to her. Both of us were naked and as her body brushed against mine, her skin felt so amazing that I almost came again. Jen turned over and moved herself on top of me, and before I could say anything she put her tiny, hairless pussy over my face. “Stick your tongue out and put it on my pussy”, Jen told me. I’d never gone down on a girl before, I wasn’t sure what to do, but I gave it my all. Her pussy was sweet, the scent and taste overwhelming me. It was so tight that when I stuck my tongue into her gash it pushed against both sides of her pussy which made her squirm.
Jen started grinding herself down onto my face, it was obvious I was doing something right. I was enjoying the taste of her pussy dripping down my face when she orgasmed. She had been writhing back and forth of my face for a while, but she practically exploded when she came. “OH! OH! OH!”, she yelled as she pushed herself down hard onto my face. Her small body was practically in convulsions she was twitching that much.
Her orgasm was short but powerful, and when she finished cumming she lifted up a bit and looked down at my through her legs. It was obvious from the look on her face that she knew she’d cum, and I knew she’d enjoyed it. “That was amazing”, she huffed slightly out of breath. “Your penis is hard, are you going to cum again?”
I explained that I could cum again but that I would have to masturbate and Jen seemed a little down. Confused, I asked if she was disappointed. “I wanted to taste your cum again, but if you do that to yourself it will go all over. Isn’t there someway that I can taste it?’ I started to explain what a blowjob was, but almost immediately she knew what I was talking about.
Without hesitation she moved off of me, kneeled down beside me, and grabbed hold of my cock. Laying on my back my cock was flat against my stomach, but she lifted it up with her little hands and slowly lowered her mouth to it. At first she washesitant , unsure of what to do, and honestly I’d never gotten head before so I couldn’t give her any pointers. She sucked just the head of my cock into her mouth, rolling her tongue around it. Jen began moving her head lower, taking more of my stiff cock into her mouth, and her hands slipped lower down my cock to make room for her exploring mouth. The combination of my first blowjob and seeing my cock disappear into her little mouth was more than enough to get me off.
She hadn’t even started working up and down and I came. I exploded, cum shooting out the end of my cock surprising Jen, and she gagged on it. Her head pulled back off my prick, her mouth opened, she was coughing, there was cum dripping out of her mouth, and I was still cumming. As she was trying to catch her breath and clear her throat cum pumped from my cock three more times hitting her on the chest, neck, and face.
The surprise wore off eventually, she was scooping the cum off her face and neck and then licking it off her hands. Undaunted by the surprise and gagging she really seemed to be enjoying the taste of my cum, licking it up hungrily. Watching her rub my cum off her flat chest and then lick it off her fingers was amazingly erotic. My cock stayed hard the entire time she was sitting there next to me swallowing my cum. “That surprised me”, she said, “You should warn me. Mmmm…”
That was all that happened that night, she and I talked about what was going to happen. She agreed to not tell her mom as long as I agreed to keep showing her things and to give her more orgasms. It was a deal I was eager to make. I was looking forward to babysitting her next week.