My First Babysitter


The other day some of my buddies and me were talking about old girlfriends and sex stories and that type thing when one friend asked me about my first time. I had thought of it often in the past many years and it inspired me to share my experience. I am only thirty years old as I write this story, but my first experience with the opposite sex was some eighteen years ago. It seems so long ago in one sense, but just yesterday in another.
I remember I was twelve years old, having just turned so only a few weeks earlier. I guess I was nieve for my age and was not very well versed in the ways of the world so to speak. I didn’t have many friends and, looking back, I was socially underdeveloped for my age. I didn’t know much about the birds and the bees, and didn’t pay much attention to girls. I was more interested in football and riding bikes than spending time with silly girls.
It was about a week before Christmas and I had just gotten out of school for the holidays. My parents were extremely hard workers and cut loose only once or twice a year it seemed. One of those times was for my dad’s yearly Christmas party his company had. They would always get a babysitter for me on the night of the big party and would stay out until the wee hours of the morning. My babysitter was always one of my aunts or my grandma, but this year they were all busy. For the first time in my life, I was going to have to spend the evening with some stranger and I was not too happy about it.
"Why mom?! I’m twelve now and I think I’m old enough to stay by myself for a few hours.

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Mom replied, "I don’t even think so young man. You are only twelve and you haven’t been exactly a perfect little boy these days you know. I don’t think I’m ready to let you stay by yourself. "
She was commenting on an incident that happened about a week before. It started innocently enough, but I guess it was a bad idea. I had been shooting my BB gun in the back yard at some targets when I decided to shoot some birds out of the trees. I shot a bird out of my neighbor’s tree and the lady that lived there had seen me do it. I hadn’t payed attention, but she was in the yard hanging out some laundry to dry. She was none too happy because she loved birds. She had bird feeders out all over the place and always spread seeds and things out so they would fly into her yard. She saw me and yelled something over at me. It startled me and I knew she was angry, so I instinctively ran into the house, despite her requests to "come back here!" Anyway, she immediately came over to tell my mom and I was in some trouble to say the least.
"It was just a bird mom. I won’t do it anymore. I didn’t know it was that bad a thing to do.

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"We have talked about this young man and I am through explaining it any further. If you would act like more of a responsible person, I might reconsider. But as it is, I am getting a babysitter and that is final!"
I knew I was beat and so I went to my room to sulk. I turn some music on my stereo and decided just to accept it and go on. It wasn’t the worst thing that could happen. I figured she would get some mindless junior or senior in high school to come over and I would have to put up with her power trip for a few hours. I was working on a model car when my dad walked in. I didn’t realize he was even home. The time flew by while I was working on my car and it was now several hours later and they were getting ready for the party.
"Hey son, how are you doing?"
"Fine dad. " I said, "Just working on my car and passing the time. "
"Well," he said, "your mother and I are about ready to leave and I wanted to just pop in. We probably won’t be home until very late and you will be in bed. Hope you have fun with your babysitter. "
"I’m sure I will dad.

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  " I was trying to sound really disappointed in a feeble hope for one last try at freedom. Little did I know at the time I was going to have a whole lot of fun.
Just then I heard the doorbell ring as dad said, "Oh, that must be her. " I walked out of the room behind him as mom answered the door. I decided to stay in the hallway to hear what directions mom gave her before I came into the room.
I heard mom say, "Hello Debbie, it’s been awhile hasn’t it. "
"Yes it has. I guess it must have been last fourth of July at the lake when I last saw you. "
The babysitter, Debbie as mom called her, had a much more mature sound to her than I was expecting. I decided to go ahead and poke my head around the corner to get a look. Before, I was expecting some teenage, only a few years older than me, but now I was looking at a woman who must have been near the same age as my mom. She was short with dark brown hair and an average build, except for her breasts. She must have had the biggest breast I had ever seen and I felt a funny feeling creep into my stomach as I gazed at them. She had a pretty face but was very pale complected. She wore thick mascara and bright red lipstick.

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   She was dressed in a skirt and long-sleeved blouse with high heel pumps and her hair was tied up in the back. She was very intimidating, but attractive at the same time. I had feelings welling up that I couldn’t understand at the time, and I had never felt up until now. I felt my penis start to stiffen and I became somewhat embarrassed as I heard mom call my name.
"Come here son, I want you to meet my old high school friend Debbie. She has just moved back to town and she will be watching you tonight. "
I walked slowly into the living room with my hands at my side hoping that my hard little cock would not be noticed by anyone.
"Say hi to my friend Debbie," my mom said.
"Hi Debbie. "
"Well hello there. You must be Jason. I’ve heard a lot about you," Debbie said. She sounded very adult in her manner of speaking. I still had trouble keeping my eyes off her breasts and I guess it was quite apparent because my mom told be to look at her eyes when she spoke to me. When I looked up, Debbie gave me a nice smile and nodded.

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"I think Jason and I will be just fine. You two go and have a good time. We’ll just grab a little bite to eat and watch some TV. " She seemed to like me instantly and I was really liking her, or at least looking at her.
Mom and dad were already running late, so they hurried out of the house with only a quick goodbye. Now I was alone with Debbie. I was very uncomfortable being alone with her and at the same time, I couldn’t keep my eyes off of her. She was becoming more gorgeous to me by the second. I had never had a girl (or a woman in this case) affect me so much. She then said, "I’ll bet you’re hungry," and walked into the kitchen. I turned to admire her ass as she left the room. It was perfect in my estimation and I was mesmerized. When she returned, she said that she put a couple of TV dinners in the oven and we would be eating in just a few minutes. All I could do was nod in response. I sat on the sofa and she sat in the recliner.

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   We quietly watched a rerun of "Friends" as we waited for the dinners to cook. After we ate, I suddenly became very sleepy. It had been a long day I guess, and so I fell asleep on the couch. I guess sometime during my nap, Debbie had decided to get a little more comfortable, because when I woke up she was wearing a tank top and the shortest pair of shorts I had ever seen. She must have thought I was still asleep as I watched her get up to go to the bathroom. Her tank top was very tight and her breasts looked like they might burst out at any minute. Her midriff showed a pierced bellybutton and her stomach was flat and tight. Her shorts were revealing to say the least, as I swear I could see the cheeks of her ass as she walked down the hall. After she closed the bathroom door, I quickly put my hand down my pants. I was actually horny and didn’t know how to react. I had never masturbated before, but now I had an instinctive urge to do it. I pulled on my pecker a few times before I heard the toilet flush. I quickly pulled my hand back out, and said hello as she entered the living room. She seemed a little startled at first.
"Oh, I didn’t know you were awake.

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  " I think she assumed I was out for the night and that’s probably why she changed into such revealing clothing. I swear she tried to cover herself a little as she quickly went back to the recliner.
She was older, you could tell, but her body looked fantastic. Better than any high school girl I had ever seen and I was going crazy. I suddenly had an incredible urge to touch her in anyway possible.
"Could I sit with you? I had a nightmare. " I lied hoping she would take the bait. I was willing to do anything to get closer to her, even though I couldn’t understand what I was feeling. It was just animal instinct I guess. She was a female and I was a male in heat.
"I guess so," she said reluctantly. I could tell she was uncomfortable. "But why don’t I come over to the couch. I don’t think we would fit too well on this recliner. " She cracked a smile, but I’m sure it was fake.

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   I guarantee I was more nervous than she was but I couldn’t turn back now, even if I wanted to.
She then got up and came over to the couch. I raised up so she could sit down and then laid my head back down into her lap. Her legs were warm and smooth as I ran my cheek across her thighs as innocently as I could. She reacted by shifting a little in her seat and then placing one hand on my head. She stroked my hair a little as we watched TV and I was becoming more and more aroused. I had gotten hard-ons before, but never like this. It felt like it was going to explode, it was so hard. I decided to put my hands under my head on her lap. I wanted to feel her legs without making it too obvious that I was some kind of little pervert. She was so smooth and smelt very nicely and I think she was beginning to enjoy the touches we exchanged as much as I was. Her hand continued to stroke my hair as I felt her other hand suddenly on my stomach. I looked up at her when she did this and she smiled down at me.
"You sure are nice to sit with Jason. " She said and I just smiled back.

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"You too, Debbie. I’ve never been this comfortable before. "
With that I felt her hand start to rub my stomach and then she slipped it under my shirt. It was probably an accident since my shirt had risen up during my nap, but her hand was now on my bare skin and that’s when something very embarrassing happened. I came.
I came right in my pants without so much as a warning. It was like having a wet dream while wide awake! You couldn’t believe my embarrassment as I lay as still as possible. I didn’t even know what had happened at the time, but I knew it felt really good.
"What’s the matter Jason? You suddenly feel very tense. " I could only hope she wouldn’t find out.
"Nothing. " I said very quickly, but somehow I don’t think she believed me.
My head was spinning from the orgasm and from trying to figure out what to do next when suddenly I felt her hand go very near my crotch. My cock was situated in my shorts so that it pointed up toward the waist and I felt her hand stop just short of the tip. Then she looked down at me with a puzzled look.

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"You are wet Jason. Did you spill something on you?" As she spoke, I must have had a look of complete fear on my face, and I was petrified.
She continued, "What’s the matter?"
Even as she said it, I saw her face change expressions as she must have figured it out.
"I’m sorry Debbie. I didn’t mean to. I don’t even know for sure what happened. "
Suddenly I saw a change in Debbie. She was no longer the pleasant person she had been all night. She became furious and I was shocked at what she would say and do next.
"Jason! Did you cum in your shorts?!"
"What? I don’t know what that means. "
"You did didn’t you!" She was becoming madder by the second. "You came in your shorts while trying to feel me up didn’t you, you little pervert!"
"Debbie please! I didn’t mean it! You were just so warm and soft and smelt so nice! You’re just so pretty!" I was trying to hold back tears as her face took on a horrified look. She stood up and walked to the middle of the living room and turned facing me. Even at that intense moment, I couldn’t help but stare at her amazing body and she saw it in my face.
"You little bastard! Even now you are undressing me with your eyes! You can’t get enough can you!" Even before I could answer she started to pull her tank top over her head.


"Well, is this what you wanted to see so badly!" She stood now topless in the middle of the floor as she flung her top into the recliner. I was stunned. It was the first pair of bare breasts I had ever seen, even in magazines. Her breasts were big and round mounds on her chest. Her nipples pointed upward and her areolas were pink in contrast to her pale skin.
"I just had a boob job last summer and I guess they got your attention didn’t they?!" I couldn’t believe they were fake, but I didn’t care. They were titties and they were in my plain sight. They were spectacular and even to this day I have never seen a better pair. She was still fuming as she quickly pushed her shorts down revealing her pussy to me. To my surprise, she wasn’t wearing any underwear. Her pussy was trimmed neatly and her mound showed nicely.
"Well, there you go! I guess you wouldn’t be satisfied without the full view would you!" I was no longer shocked at what she was saying. Her naked body had my full attention and I listened only slightly at what she said. That is until she decided to punish me.
"Your mom and dad won’t like this a bit! I’d better punish you for this! Drop your shorts! I’m going to give you a spanking!"
I was scared now, but was not about to do anything to make her more mad.

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   I stood up and dropped my shorts and underwear to the floor. My hard little cock poked up toward my stomach as the cum from my orgasm covered my pelvic area and had started to drip down on my ball sack. I have always cum a lot when I have an orgasm, even for my first time. She looked down at my cock as I awaited her next move. She came over and stood beside me. I still had a hard time looking away. She then put one hand on my shoulder and began to slap at my butt cheeks with her other hand. To my surprise, she was not hitting me very hard. She slapped me about five times and then something incredible happened.
"Well, I guess that’s a start. " She said. "But I’m not through with your punishment. "
I noticed a change in her tone. She was breathing harder and looking down at my penis as she spoke.
"I guess next thing is to clean you up.

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   You look a mess. "
I started to walk to the bathroom to get a towel or something to wipe myself down with when she stopped me.
"Where do you think you’re going young man?!" She seemed more upset again. I was confused and said I was going to the bathroom.
"No! I’m not letting you out of my sight any more tonight. I don’t want you to do anymore harm than you already have. You will probably go to your room and try to screw the bed or something!"
I was still scared and confused as she told me to come over to her. She sat on the couch facing me as I walked slowly toward her.
"I guess I’ll just have to clean you up myself. Don’t think for a minute that I like doing this!"
When I got close enough, she reached behind me and pulled me quickly toward her. Before I knew what happened, my hard virgin cock was in her mouth. She sucked on it for several seconds as I tried to figure out what was happening. I was paralyzed as I felt her tongue start to lick the underside of my cock. Then she pulled my cock out of her mouth and pushed it hard against my stomach. She looked up at me and mumbled something about how dirty I was and then started to lick and suck on my scrotum.

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   I could already feel another orgasm coming on as she finished licking my balls and all around my pelvis. She had my cock in her mouth again as I came. She didn’t look nearly as surprised as I thought she would and looking back on it, I think she must have known what was coming. She simply continued to suck my cock until I had completely unloaded into her mouth. I felt her swallow and then she pulled her mouth away.
"Now unless you want me to tell your parents what you did, you will fuck me. I know you want to and you owe me one. "
Her eyes were intensely serious as she sat back into the couch and spread her legs.
"I don’t know how," I said as I slowly inched my way closer. She grabbed me again and pulled me in toward her, more gently this time. I watched as she guided my cock to her pussy and when the head was at her entrance, she pulled me by the ass until my five-inch little cock was all the way inside. It felt warm and velvety as I instinctively tried to push deeper.
"Just pull part way out and push it back in. " Her voice was more tender than before although she was still very demanding. I began to pull in and out of her pussy as best I could.

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   She was trying to give me directions on how to do it and I was trying my best to oblige. She must have been frustrated with my efforts, because she suddenly pushed me away with a loud sigh.
"This isn’t working for me. Your little cock is just too damn small to satisfy me. "
She then stood up and put her clothes back on. I thought she was actually leaving as she rushed out the door. I couldn’t believe she would leave me alone when she was supposed to be babysitting me. Suddenly, though, she came back into the house with something in her hand. To my amazement it looked like a man’s penis. It was long and thick and black. She quickly stripped again and began to suck on the penis intensely. She then came back to the couch in front of where I was still standing and kneeled down with her back to me. I watched as she reached around with the fake penis and pushed it hard into her pussy as she leaned over the sofa. It was very sexy to watch her pull it in and out of herself and I began to stroke my cock as she moaned. Then she looked back at me and spoke.

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"Now put that worthless little cock into my asshole. " I was stunned and shook my head at her.
"No! I can’t do that. That is where you poo from. I won’t!"
I still didn’t want to do it but I was convinced she would tell on me if I didn’t. I guess it didn’t dawn on me at the time that she could get in much more trouble than I could for what was happening. I was young and ignorant and a little scared, so I did what I was told. I put my cock at her asshole and pushed. It wouldn’t go in at first but she insisted I keep trying. When it finally did pierce her ass, it felt great and I was no longer feeling grossed out. I was feeling very horny again and push as hard as I could. I was fully inside her in seconds and I loved it. It wasn’t long before we had a good rhythm going and Debbie was moaning like crazy. She was fucking herself with the black penis while I pumped away at her tight ass.

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   Because of the situation and the fact that I was so new at this, I felt my next orgasm building up strongly.
"Debbie, I think I’m about to do it again. What should I do?" I asked.
"Just cum in my ass," she shakily replied, very much to the point.
I did what I was told as she screamed loudly. The feeling was intense and I thought for a moment that I might collapse. My knees felt wobbly and my head was swimming as I emptied my balls into her ass. I could feel my thighs suddenly become very wet and this time I knew it wasn’t from me. My first thought was that she was peeing on my so I quickly pulled away as a string of my cum stretched from the tip of my cock to her ass. I watched as she continued to push her toy in and out of her pussy. There was clear liquid splashing all about as she was screaming. Finally she stopped and pulled it out. A gush of liquid escaped and hit the floor with a slight thud. She collapsed face down into the couch and gave out a throaty moan. I stood not sure what to do next when she turned to me and spoke.

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   Her voice was very tender now, much like it had been before all this had started.
"Oh sugar, you did fine. Just fine. " She was still quivering a little and her voice was shaky.
She then rose up, turned around, and walked over to me. I could see her juices running down her thighs and her entire body was glistening with sweat. Her hair was a mess also. She leaned down a little and gave me a big hug.
"I’m sorry I sounded so mean to you. I just get a little different when I am turned on. Do you understand what I mean?"
Of course I didn’t at the time, but I shook my head up and down anyway.
"I really do like you Jason. I didn’t mean all those terrible things I said before. I wasn’t exactly myself there for a while. When I realized you had cum in your shorts, I just got so damn horny I lost my head.

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  " She was like her old self again, only still very much naked in front of me, and so was I for that matter.
"Why don’t we go get cleaned up and then we will tidy up the living room before your parents get back?" She looked at the clock and I did too.
It was getting very late and I was suddenly very nervous because my parents could possibly be home anytime now. I didn’t know for sure. My cock was limp for the first time in quite a while and I felt very satisfied. I knew I had just been with a woman. Not a girl, but a woman. And it was the most erotic thing I would ever experience. From that time on, I would always ask for Debbie when my parents went out. They were a little suspicious when I was still asking for her when I was seventeen. If they had only known how well my babysitter took care of me!



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