This story is about a middle aged father who catch’s his teenage babysitter watching his porn.
As parents of two kids we were always busy, so busy in fact that we never thought of hiring a babysitter. We had two kids, a 10 year old boy and a 8 year old girl, the way I figured it we were about half done raising them and could probably handle the next 10 or so years ourselves. We would occasionally have our parents or siblings watch the kids if we needed some time off, maybe we were just too cheap.
But one day when we had just finished eating dinner there was a knock on the door. It was a girl named Amy from the neighborhood; she lived a couple of houses down. She explained that she was looking to raise some money and was looking for a job babysitting. I had seen her in the neighborhood growing up and always thought to myself “Damn, she is going to be a bombshell when she gets older, just like her mother.” I didn’t know the family, except for the occasional “Hello” in passing. She was a cute 12 year old, about 4’ 9” tall, she had beautiful log straight red hair, green eyes with red eyebrows, freckles and a body just starting to show the first signs of womanhood. She had always seemed like the shy type, but when I opened the door that day I sensed that she had a devilish side to her. I invited her in and my wife and I asked her about what her availability was and a few other questions. That night after the kids went to bed we discussed the idea and both agreed that it would be nice to have some evenings off and that her price was reasonable. We decided that we should probably discuss it with her parents as well. We made plans to have dinner with her parents.
Her parents, Dave and Mandy had us over for dinner. They were a nice couple, their daughter Amy was an only child. Mandy was absolutely gorgeous, in her late 30’s, she looked like she was 30 though. Her daughter defiantly got her looks from her mother. Mandy was also a red head, she had a perfect figure, c-cup breasts, that she wasn’t shy about, her blouse that she wore during dinner showed a generous amount of cleavage. Dinner was excellent and we decided that Amy could start that weekend.
After getting home that night I stayed up late to finish some paper work I had taken home from work. I kept finding my mind drifting into erotic fantasies about Mandy, and believe it or not, also her sexy little daughter. It wasn’t long before I found myself with a raging hard on, that I relieved while thinking of those sexy red heads. After a month or so my fantasies had turned into a fetish about red heads and I found myself in the local porn shop one night picking out a couple of porn movies that were called something like “Redhead Teens”. I kept them hidden away so my wife wouldn’t find them, but they still got quite a lot of use, every time Amy babysat I found myself whacking off to one of the hot redheads on the DVD’s while fantasizing about Amy after she left.
About a year later my wife had to go to a conference out of state. I had made plans to go out with a few of my buddies that night. I called Amy and arranged for her to babysit. My kids weren’t home from school yet, so I popped one of the Redhead DVD’s into the DVD player and rubbed one off before the kids got home. I was relaxing in an after orgasm daze, my cock in my hand and my belly and chest spotted in fresh cum, when the phone rang. I quickly cleaned up my cum and ran to answer the phone, I turned off the TV but forgot to put the DVD away. It was a one of my friends on the phone, they decided to go to a different bar that night, we chatted for a minute, I told them I would meet them later. After I got off the phone I hopped into the shower. By the time I was out of the shower the kids were home from school. An hour later Amy knocked on the door. I opened the door for her. She was now 13, and looking hotter every day. But this day I was in awe, she had never dressed this sexy before. She was wearing a short white skirt; I gawked at her long white legs. I dreamed of how smooth her legs must feel, especially her inner thighs. Her blouse was pink, and very tight on her, emphasizing her still growing breasts. I could tell she was not wearing a bra, her almost b-cup size breast had two nipples pointing at me though the blouse. It took all the restraint I possessed not to get an instant hard on. I invited Amy in and gave her the normal info you give a babysitter, when I plan on getting back, what’s for dinner etc. Then I left.
I stayed out a little longer than usual; I drank a little more than usual as well. By the time I got back home I was about 90 minutes late. I decided not to park in the drive way, as that would alarm Amy of my presence, instead I parked a couple of houses down in the street. My liquid courage gave me the perverse idea to see what Amy did all by herself after my kids went to bed.
I snuck out back of the house. All the lights were out except for the kitchen and living room. I could tell Amy was watching TV, by the flashing of different color lights in the living room. I snuck to one of the windows that looked into the living room. Amy was on the couch which was right in front of the window, so I could not see her, but I almost shit my pants when I saw what she was watching. On the TV were two hot redheads pleasing a man. ‘Shit, I forgot to put the DVD away!’ I thought to myself. For a split second I was worried, but that almost instantly went away as my mind shifted gears into a different thought, how much it turned me on that my redheaded 13 year old babysitter was watching my porn! I was instantly hard. I wanted to see Amy so I went around the side of the house and peeked in through a different window. Amy was sprawled out on the couch intently watching the movie. She was still wearing her sexy skirt and blouse. I watched her for a while, watching her fidget around, into different positions on the couch. Occasionally she would caress one of her breast through her blouse, or itch her butt. I was hoping that I would catch her masturbating, but she didn’t.
At one point she re-positioned herself facing toward the window I was peeping through. She lifted one leg up onto the couch, giving me a peek up her tiny white skirt. I almost melted, I was sure she wasn’t wearing any panties, but I could not really make out too much in the shadows between her legs, I was pretty sure I could barely see the crevasse between her pussy lips. I was about to whip out my cock and start masturbating when I noticed a car coming down the street. ‘Damn’ I thought as I slipped into the back yard of my house to avoid being seen.
I decided it was time to go inside the house; I was curious what Amy’s reaction would be, after she found out my porn interests in teenage redheads. The door was locked; I unlocked it and entered the house. I heard a bunch commotion in the living room; no doubt Amy was jumping up to turn off the TV and DVD.
I entered the kitchen and the flustered young teenager met me in there. Her face was beet red, and she was nervously straightening out her hair. I asked her how the night went; she said it was alright, her young voice quivering with nervousness. I asked her if she wanted some desert or anything, I was hoping desperately that I could get a better look up her skirt. She awkwardly declined and said she needed to get home, that her parents were probably wondering where she was. She hurried by me towards the door.
As she passed it couldn’t help but admire her cute little butt, my jaw almost hit the floor when I noticed a little wet spot in the back of her skirt. The DVD must have really turned her on to get her that wet. After she left I couldn’t help it, I knew I had to relieve myself. As soon as the door shut I was in the living room.
I went over to the couch where Amy had been sitting and ran my hand across it. I felt a small wet spot. My dick was now raging hard as I knelt over and smelt Amy’s teenage juices she left behind. They smelt musky and sweet. Then I sat on the couch and took off my clothes. I turned on the DVD and it picked up right where Amy had left off, a man fucking a flat chested redhead doggy style, while she ate another redhead’s pussy. My mind was wild with thoughts of Amy watching the porn movie; did she wonder why I had a fetish with redheads? I was stroking my hard cock when all of a sudden I heard a gentle knock on the door. I looked across the living room, wondering why Amy would be knocking on the door, and I noticed she had left her little purse on the coffee table in the living room. A dirty plan came into my mind; pretend I didn’t hear the knock and continued masturbating. I slightly turned up the volume of the T.V., not enough so that my kids would wake, but enough so that when Amy came into the house she would hear it. I heard the front door close.
“Mr. Smith…. Are you there?” Amy inquired. I didn’t respond. Amy then entered the living room and as soon as she saw me she said “Oh, um, I am really sorry Mr. Smith, I uhh, didn’t know you were uhh…”.
I finished her sentence for her. “Masturbating.” I said.
“Well I guess, I , uh…” She answered then she proceeded to grab her purse. She turned around and started walking out of the living room. I noticed her gawking at my fully erect cock as she walked by.
“Did you enjoy the movie?” I asked her. She lied and said she didn’t know what I was talking about. I laughed it off and told her that I had seen her watching it. I asked her again, this time she told me she did enjoy the movie. “How did it make you feel Amy?” I asked.
“It really got me excited.” She replied.
“It really gets me excited too Amy, that’s why I am jerking off. In fact you get me really excited also; I think you are the most beautiful teenager that I have ever seen.” I told her. She looked over at the porn scene on the T.V., a devilish smile slipped across her face. A man was fucking a busty redhead in the ass.
“Even prettier than her?” She asked.
“You are much more beautiful than her Amy.” I said. “Her boobs are much bigger than mine.” I smiled, and began to stroke my cock again; I had to go really slow so I wouldn’t explode. “Just wait baby, your mother has big tits, yours will get there someday, they are still growing.” I replied. Amy looked back over to me. Her eyes fixated on my cock. “Have you ever masturbated Amy?” She said that a couple of months ago she had her first orgasm. This blew my mind and I actually had to stop stroking so I didn’t cum right then. “Would you like to play together?” I asked. She flashed me another devilish grin and said, “On one condition, as long as we go all the way Mr. Smith.”
I could not believe what she was saying, and I didn’t waste any more time. I stood up and walked over to her, my hard cock sticking straight up in the air, pre-cum dripping from it’s head. We embraced awkwardly, and then she tipped back her head to kiss. She was much shorter than I was, so I had to bend over a little before our lips met. I melted in her arms; her young lips were experienced as I found us French kissing very soon after. Our tongues danced with each other. This lasted a minute or two, during which ground my hard cock against her blouse covered navel. When we broke the kiss she stepped back and I could see the wet spot on her blouse from my pre-cum. She touched the wet spot with her slim fingers and tasted it.
“It seems like you have practiced kissing a bit.” I said.
“Yeah, my friend Trevor and I have practiced a few things together but I haven’t gone all the way yet.” She responded. At that moment the woman in the video started to climax and cry out in pleasure. Amy turned away, so her back was facing me and watched the woman cum. She slipped off her blouse and dropped her skirt to the floor. She wasn’t wearing a bra or panties. I gawked at her smooth skin, her nice round and small buttocks. I walked up behind her and grasped onto her arms and began kissing the back of her neck. She moaned. I ran my hands up and down her skinny arms. I then reached around and cupped her growing breasts, squeezing them and gently rolling her nipples between my fingers. The next scene on the movie was on, a woman starting to suck a cock. Amy read my mind. She spun around and held me at arm’s length, pushing me back towards the couch. I was getting my first view of her sexy young body.
Her breasts were firm and round, like cones, they had no sag yet. Her areolas were small, but erect from the stimulation they had just gotten from my fingers. Her hips were just starting to bow out a little, giving her just a little bit of form. Her pussy was very sexy, her red haired bush was not even half developed yet, so I could see her well formed labia; and peeking out of it I could see a tiny bit of her little pink clitoris.
I sat on the couch, almost paralyzed by the sight f her sexy body. Amy knelt in front of me and wrapped one hand around my cock, and the other grabbing my balls. She stroked my cock and said, “Yours is much longer and thicker than Trevor’s dick.” I moaned in response. After a few strokes she bent over and started licking my head. She soon took my whole head in her mouth and began sucking it, her tongue tickling the tip. While she did that I ran my fingers through her hair. Before long she was taking as much of my dick into her small teenage mouth as she could, awkwardly gagging occasionally. I could tell that she had done this before but that she still needed some practice. After a couple of minutes I couldn’t take it any longer and I began to climax.
I moaned as waves of the most intense orgasm I had ever had in my life jolted though my body. It caught her by surprise, the first shots hitting the back of her throat; she gagged and pulled my throbbing cock out of her mouth. The last three shots hit her in the face as she milked my penis with her hands.
I apologized for cumming so quickly, she laughed it off. “Your turn!” I said.
We switched positions. I knelt in front of her as she slouched on the couch, sliding her butt to the edge of the cushion. I opened her legs and then ran my hands down the inside of them. Her inner thigh skin was the smoothest skin I think I had ever touched. I felt her mound, slipping my finger between her labia. The inside of her vulva was drenched in her teenage body’s natural lubricant. I spread her lips and paused for a moment, admiring her pink vagina. I kissed the inside of her thighs, slowly making my way toward her pussy. When I finally got there I could smell her natural scent. I flicked my tongue up and down in her slit. She moaned in response. Next I began sucking on her clit, I reached my hands up onto her chest, grasping her breast. I could tell Amy was thoroughly enjoying this, her head was rocking back and forth and her legs occasionally jumped in pleasure. Soon we were moving together in rhythmic motions. I brought one of my hands down and inserted it into her virgin vagina. It hit her hymen; I didn’t let that stop me. I thrust my finger deep into her; as her hymen broke she gasped in pain, her little butt jumping momentarily off the couch. I kept eating her thirteen year old pussy, and soon we were back into our rhythm. Her pussy was tight around my finger as I thrust it in and out while sucking on her clit. Soon her hips began to rock furiously and moans turned into whimpers as she bit her lip to contain her cries, probably so she didn’t wake up my kids. She convulsed violently as she began to climax, her hands holding my head between her legs.
After she was done she lay on the couch limp. I was ready for round two, after brining my own teenage babysitter to a climax and breaking her cherry with my finger; I was as hard as a rock again and needed to fuck her. I picked her up off of the couch and laid her on her back on the floor. I crawled over her and we began to kiss passionately. She whispered in my ear, “Fuck me Mr. Smith, fuck me now.”
I spread her small legs with mine, and began rubbing the head of my cock up and down her soaked slit. I slowly inserted my cock into her pussy; it took a couple of tries because she was so tight. Her face showed the pain, and she dug her fingernails into my back in a desperate response. Finally I slid all the way into her, or at least until my cock hit her cervix. I slowly began pumping her, and she gradually began to relax. After a few minutes of taking it slowly we were full on fucking. I rammed her and she moaned, her firm boobs barely bouncing. She began climaxing again, I didn’t slow down though, and she began to have multiple orgasms. She was so tight I could feel her love tunnel grasping my dick. Her small frame jerked in ecstasy and not long after I felt my second climax coming on. “Oh, yes Amy, Oh baby, yes.” I moaned as I began to fill her virgin womb with my cum.
I stopped after ejaculating the last drops of semen in her, the head of my hard cock resting against her cervix. We lay there for a while, until she told me she had to go home. We kissed again and then I pulled my now limp penis out of her. She got cleaned up and dressed, gave me a quick kiss and said, “I guess I will see you on Monday.” I told her I looked forward to it.