Naughty Babysitter - Dreaming

This story is a fantasy of mine. It is a work of fiction and is not intended to implicate any person or action by them or me.

I do not advocate underage sex. My first sexual experience came when I was 14 with a 16 year old boy. Although at 15 I had sex with a 45 year old husband from my dad’s office and then at 16 I started having sex with my parents and aunt, I realize that I was raised under rather unique circumstances which would not apply to most people. I baby-sit and work with youth in my church, positions where parents put a great deal of trust in me to take care of their children – a trust I would never betray. Admittedly I may fantasize a LOT and when I am with them my eyes may wander and my thoughts may be a bit indiscrete, but I only dream…

I use to baby-sit a lot but now that I am 19 and a college sophomore with tons of schoolwork, I don't do it nearly as much as I use to. Although many of the kids I sat for were at an age when sex was beginning to creep into their minds, I never even considered doing anything with the kids I was entrusted with – that is until recently. One of the main reasons I have this profile is to chat with different people to learn about their fantasies and sexual lifestyles. Lately I have been chatting with a number of guys who are interested in having sex with their sons and daughter as well as other underage kids. There was one guy who wanted me to have sex with his 12 year old daughter in hopes it would eventually lead to him having sex with both of us. Another guys wanted me to help his 11 year-old son learn about sex – using the hands-on method of teaching! He wasn't interested in joining us but he clearly wanted to have me after his son finished his lessons.

Although at first this line of talk totally turned me off, the more I discussed it the more it has caused me to started thinking about the possibilities. At first I just wrote some fantasies for a couple of guys which were inspired by their desires and cravings for their kids. In the process I found myself getting turned on by the scenarios I was writing about. Before I was finished with them they were not just fantasies written for some guys, they had become my fantasies as well. In the past couple of months I have found myself becoming more and more obsessed with these thoughts. The question for me was whether I would just fantasize or actually do something about it?

I guess I should clarify something before I go any further. While I waited to have sex for the first time until I was 14, I had been thinking seriously about it since I was 12. I love to fantasize about the possibility of me having sex with someone that age who is wanting what I did then. However, I would never force anyone to do anything, no matter what age they were but especially when it came to someone younger. If anything ever did happen between me and someone I was babysitting it would be because they wanted it, not because I started it. Of course, that doesn’t rule out making myself available…….

Shortly after I got home for Christmas vacation I was contacted by a nice couple whose kids I have baby-sat dozens of times over the years. The kids are now a 13 year-old boy and his 12 year old sister. I quickly agreed and it wasn't until after I hung up the phone that I caught myself wondering just how much little Billy and cute Jenny had grown since I last saw them. Hmmmmm, especially little Billy. Even last summer I noticed he was developing at an early age and his attention seemed to be more and more directed below my neck when I was near him. Back then I wasn’t thinking about anyone his age but now some very naughty thoughts were developing as I dreamed about the two of them.

For the first time I looked in my bedroom mirror before babysitting and wondered what the kids I was going to be watching would think of me – not just in terms of how they liked their babysitter but in a sexual way. I had picked out a tight pair of jeans, the type that warned me when I gained a pound. They were cut pretty low and showed off my ass nicely. On top I had on a tight tank top cut short enough to show most of my midriff. The fact I wasn't wearing a bra was obvious from the way my nipples poked through the thin material. It clung to my boobs like it had been painted on them and was sheer white which showed off the dark outline of my nipples. Over the tank top I wore an oversized flannel shirt, unbuttoned about half way down such that you could see I was wearing the tank top underneath, but enough to cover up what it revealed. I left it hanging out and it hung just below my ass. I shook my head and let my hair fall to my shoulders. I debated whether to tie it back in a ponytail or leave it loose and decided that the ponytail looked just a bit too high-schoolish. My hands cupped my breasts and lifted them as I smiled to myself. They may be barely a B cup but they were firm and perky. Instinctively I squeezed them and felt a surge of pleasure. They were soooo sensitive and I loved playing with them. I closed my eyes and rubbed them, pressing my nipples between the fingers of my hands. Just then my mom called from downstairs, warning me it was time for me to get going. Reluctantly I took my hands off of me – a few more minutes and who knows where I would have been touching!

It was long before I was in a whole different world – getting last minute instructions from the parents. Dutifully I listened as their mom explained where they would be, the phone numbers for everyone, and when they would be home. They kissed their kids goodbye and suddenly there I was, alone with Billy and Jenny. This scenario had played out dozens of times in the past for me but never had I felt the way I did now. In reality, I wasn't sure what is was I really was feeling right then. While on the one hand I was excited over the possibilities and the resulting lust that was rising in me. On the other hand was the self-doubt and worry about doing something I might regret for the rest of my life.

As soon as their parents were gone, Billy went back to playing his video games and Jenny wasted no time in chatting with some friends on the computer in the family room. I could tell this was not going to be a very challenging babysitting assignment. Actually, I didn’t understand why they needed me to be here in the first place as they seemed old enough to be home alone. Oh well, it was better than a pair of screaming babies wanting their diaper changed or spoiled kids crying for mommy and daddy to come home! I settled down in the family room and watched TV. Now and then I would check up on them but they were rooted in position. After about an hour of this I went to Billy’s room where he was playing some silly game. I asked him how it was going and he just grunted, not even turning around to look at me.

At nine o’clock I told Jenny that it was time for her to get ready for bed. I offered to help her get ready and the two of us went to her room. She had a pretty bed with frills and a pink comforter with lots of dolls arranged carefully along the edge next to the wall. Judging from the posters on her walls she was well into her boy-crazy stage and based on my own experience I imagined she was masturbating on a regular basis dreaming of being with them. Jenny undressed down to her panties which allowed me to see her cute naked figure. Jenny was certainly going to be a babe when she grew up! Already she had a nice little body which was beginning to more than hint at the foxy girl she would soon be. Her legs were long and still a bit on the coltish side but you could see already how they were destined to look great in a miniskirt. She wore her auburn hair long, about half-way down her back. Her green eyes were beautiful and she had a smile that made you melt. Her breasts were starting to bud and I thought of how nice it would be to suck on those nipples and feel them harden.

Still topless yet completely unashamed of her nudity, Jenny walked over to her dresser and reached into a drawer for a cute nightshirt with a picture of a kitten on it. I commented to her that she should change her panties before going to bed. She shrugged and without another word she lowered her white cotton panties, giving me a nice view of her tiny pussy which was just starting to show the growth of her future bush. She has a perky little ass which she instinctively wiggled as she walked – god she was going to kill the boys! She leaned over to pull on a clean pair of panties and it was all I could do to keep from holding her butt and reaching between her legs for that virgin pussy. Soon her panties and nightshirt were on so I tucked her into bed and kissed her on the cheek, thinking all the time about what would happen if I kissed her somewhere else, somewhere a bit more private. I wondered what she would do if I were to undress and get under the covers with her, pressing my naked body against her as I pulled her tightly to me. I wanted to teach her how to lick another girl’s pussy, to know the wonderful sensation of being in a 69 with another woman. Oh well, for now it was all just a fantasy for me.

By now it was getting close to 9:30, a half hour from Billy’s bed time. I took off my flannel shirt leaving just my tight tank top on and went to the family room where Billy was studying at the game table. I went to the opposite side of the table and sat down across from him. He looked up at me briefly and then his eyes went straight to my chest. I tried to hide my smile as I saw them widen as he took in the image of my breasts which were clearly outlined in the tight sheer fabric. After spending time with Jenny my nipples were hard and pointed and were plainly visible for him to see. The tank top was cut low so my cleavage was plainly visible and in fact it barely covered my nipples.

“Hi Billy,” I started out with a sly smile, “How is the homework coming?”

Billy just shrugged and frowned. He was clearly more interested in watching my boobs than talking to me. I stood up and leaned over the small table so I could supposedly see what he was doing. What I was really doing was giving him a clear view of my boobs down my tank top as I leaned forward. Leaning forward like that didn’t hurt either when it came to showing them off!

“Hmmmmm, looks pretty hard. Can I help?” I asked him.

“Noooooooo,” he said softly, “I can do it.”

I slowly moved back and off the table. I walked around behind him and leaned over him. I put one hand on each shoulder and then in the sexiest, most slutttiest voice I could muster, I whispered in his ear, “Well you know Billy, if there us ever anything I can do for you, anything at all, all you have to do is ask.”

With that I went back to the couch and watched TV. As I walked over to the couch I did not look back at him but I could literally feel his eyes staring at my ass. Finally ten o’clock arrived and I called over to Billy, telling him it was time for him to get to bed. As he got up from the table I asked him if he needed any help and he wasn’t afraid to answer this time, an emphatic “NO!” I turned to watch him leave and it was all I could do to keep from smiling when I saw the bulge sticking out from the front of his pants. Somehow I don’t think he had gotten a lot of homework done for the past half-hour!

The entry to the family room was off to the side and behind me so anyone coming in could see me before I saw them. After he had been gone for a bit I heard some soft foot steps and a slight rustling sound from that direction. Just as I had hoped, little Billy had sneaked back to get another look at his babysitter! Well, my plans were to put on a show he wouldn’t soon forget so I shifted my weight in the couch, spreading my legs just a little bit more. My stocking feet were flat with my knees up in the air about a foot apart. I put on hand on each of my boobs over my top and started to slowly fondle them. I alternated between squeezing them and lightly running my fingers around them. I love to brush against my hard nipples, tracing my finger around them feeling a tingle in my breasts as I did. I closed my eyes and laid my head back against the pillow, enjoying myself. I pulled up my tank top until it was barely covering by boobs. With my low-cut jeans most of my belly and torso was visible. With one hand still on my boob, I took my other and dragged the backs of my fingers across my bare skin, letting my fingernails drag across my smooth skin. Then I slipped my hand under my top until I held my bare breast in it. Mmmmmm, it felt so firm and warm! My other hand slipped underneath also and I let out a series of low moans as I squeezed them harder, pushing them together and rubbing them against each other.

Knowing that Billy was watching was making me even hornier than usual. No matter how quiet he was trying to be, every now and then I would hear slight sound as he shifted his weight or otherwise moved. He was probably playing with himself by now so it was time to up the ante! I unsnapped my jeans and slowly unzipped them all the way down. I opened them up but you couldn't see anything since I was shaved. I slipped my right hand down inside until I was fingering my clit. My left hand went back under my tank top again to pay attention to my boob again. I slid my right hand finger down my pussy slit and into my hole to wet it and then returned to my clit which was getting nice and hard, making it even more sensitive to my touch. I couldn’t help but jump as I put a finger on each side of it and rubbed it up and down. God I love to masturbate! It is even better when I have somebody watch me and right now I had a feeling Billy was doing himself as well. I tried to imagine him peeking around the corner, watching me laying on the couch with my jeans unzipped and my hand inside; watching me fondle my breasts and seeing the look of joy and pleasure on my face. I hoped he could hear my moans as I brought myself to my first climax, my back arching and then my hips raising as I came thinking of how my dad had fucking me earlier in the morning.

I wondered if Billy had ever seen a girl orgasm before – I doubt he had. He had to be horny as hell right now! I thought of him reaching inside his loose pajama pants, touching his still small but rock hard penis, rubbing it against his crotch and then jerking off with his hand as he watched his babysitter doing things he and his friends had whispered about when they looked at their dad’s porn magazines. After my first orgasm I was so horny I could hardly stand it. God I wanted to be fucked soooo badly! I knew it might be going too far but I had to masturbate harder and I couldn't do it with my jeans on so I grabbed them by the waistband and pulled them down to my ankles. As was the usual case for me, I wasn't wearing any panties so that left me bare-ass on the couch. I spread my legs wide and went to work on my soaking wet pussy, inserting first two then three and finally four fingers into me. I wasn’t dreaming of my dad fucking me anymore – now I was imagining Billy had come from his hiding place and was kneeling naked between my knees, his hard little cock pointing up straight as a rocket ready to blast of. Well, it was a rocket I wanted to blast off inside of me!

It was all I could do to keep from turning around and calling for him to come in and fuck me. Instead I just imagined him entering me as he fucked a girl for the very first time, feeling a warm wet pussy gripping him in a way his fist never had or even could.

“Oh god Billy,” I moaned as loud as I dared, “That’s it, fuck me……..fuck me harder Billy!”

Billy must have heard me! I hoped he realized that I was masturbating while I thought of him fucking me. I bet he was cumming all over himself by now as he listened to me begging him to fuck me more, asking him to cum inside of me, to let me feel him in me. I bet he had never heard a girl say that to him before. After tonight I wondered how many times he would masturbate while reliving this moment, hearing me crying out as I came again and again, each time calling out his name and telling him how much I loved to be fucked by him.

After my 3^rd orgasm I was exhausted. I laid on the couch with my finger inside of me, slowly moving it in and out as my body tingled. I had not yet lifted my tank top up to show him my breasts so for a few minutes I lifted it up and over them while I used both hands to touch them softly. I wet my fingers from my naughty pussy and then traced them around my nipples. I felt flushed and warm all over my body. I would have given anything right then to have him come to me on the couch and let me teach him how to fuck me.

That was not going to happen, at least not tonight so I eventually stopped playing with myself and pulled my top down. I grabbed my jeans to pull them back on as well. I lifted my hips to work them on – they were pretty tight and not all that easy to get back on again! I slowly stood up and straightened out my appearance. Turning towards the doorway, I thought I say a quick flash of movement but had I not been expecting it I probably would not have noticed anything. I gave Billy a few minutes to get settled in and then I went to his room to check up on him. Pushing his door open, I saw he was in bed under covers. I could tell he was awake – nothing more obvious than a kid trying to pretend he was asleep! His face looked flushed and I smiled as I imagined the thoughts that must have been running through his head at that moment. It was so tempting to walk in and have more fun with him, I didn’t doubt for a moment he was praying that I would. But I figured tonight had already gone far enough and before I did anything else I had better see what the results of tonight were. So far the worst I could be accused of was being indiscreet. What I really wanted to do with Billy was far more than that! Well, I would have to wait and if everything went well, then my next babysitting assignment here could prove to be pretty interesting!

The parents came home a couple of hours later. They asked how things had gone and I told them everything went well. I wondered what they would say if they had any idea of just how well it had actually gone! Being it was so late the father drove me home even though it wasn’t that far away. While in the car I noticed him glancing my way more than a few times and for a moment I thought about teasing him a bit. By then we were already at my house and I was saying goodbye. Oh well, you never know what opportunities may come up in the future! He mentioned as I was getting out that they might need someone again next week and he was wondering if I was available. I smiled at him and coyly told him I was always available, all he had to do was ask. We laughed at my “joke” although I think we both realized that I was talking about more than just babysitting. I walked to my home, thinking that maybe seducing the father after I had fucked his son wasn’t such a bad idea!

My parents were asleep so I undressed and got in bed. There would be plenty of time tomorrow to tell them about my evening. I couldn't wait to tell my mom as I knew she would be thrilled to hear how naughty I had been! Laying in my bed I ran my hands all over my naked body as I relived those moments on the couch. I could hardly believe how hot it was to play with myself while a 13 year old boy watched me! Before long I was at it again – no such thing as too much masturbation so far as I was concerned! All I could think about was what I wanted to do the next time I babysat for Billy and Jenny. Next time I knew I would do more than just play for him to watch! I orgasmed thinking of his little hard cock pumping cum into a pussy for the first time as he came inside of me, Mmmmmm, next time I was going to REALLY be a naughty babysitter!

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