The Babysitter ExperiencebyRobb©
It still feels like a dream.
My wife had to fly to her sister's house for the weekend to help with her sister's house remodeling. I didn't mind since I had no plans for the weekend and I figured I would spend time at the pool with the kids enjoying the weather. I had just dropped my wife off at the airport when I got a call from work. My boss had called an important meeting for Saturday afternoon. Since I had the kids, I needed to call Christie to baby-sit the kids. Twenty-year-old Christie had been the kids' babysitter for the past few years and did a great job with them. I called Christie and she was happy to baby-sit since she had no plans for Saturday.
Christie is a very young looking. Born to a Hawaiian mother and American father she had the innocent looks of her parents. She is about 5' and all of 90 lbs. As with women from the South Pacific, her chest was rather tiny; but her smile was extremely large for her face.
I picked her up on Saturday about 2:00 pm and took her back home. She had a little bag with her and she was dressed in shorts and tank top with her bathing suit underneath. We got back to the house and she took the kids out to the pool while I finished getting dressed for the meeting. As I looked out of the window at Christie and the kids and admired how cute Christie looked in her bikini. Even though she seemed almost flat-chested, she had a sexy appeal to her. "What am I thinking?" I asked myself. Thoughts of the young babysitter were just not right. I shook those thoughts out and headed to the meeting.
The meeting was boring and a complete waste of time. During one of the breaks I checked my voice mail on my cell phone and had a message from Christie's mom asking if Christie could spend the night since they were going out and going to be home very late. I called her back and told her that there would be no problem.
I got home about 8 and walked in the house. Christie was asleep on the sofa with the TV on. I went in to check on the kids. Seeing the kids were fine I went through the living room on the way to my bedroom and looked over at Christie sleeping. She was wearing a one-piece nightie that was bunched up around her waist showing her panties. She was wearing a cute pair of pink panties that looked too big for her tiny ass. She looked so innocent and sexy. I had to get the thoughts out of my head so I headed for the bedroom and then right into the bathroom for a shower.
I was just getting out of the shower when I heard, "Is that you, Mr. Niles?"
It was Christie standing there in her nightie staring at me. Not realizing that I was standing there naked I answer her that I just got home and needed a shower. Finally noticing my appearance I grabbed a towel and covered myself. Excusing myself, Christie left the bathroom and went out to the living room. It was awkward for both of us, but I know she was looking at my semi-hard cock.
I put on a pair of shorts and went out to meet her in the living room. She was sitting on the sofa watching some movie. "Christie, … I'm sorry I didn't wake you when I got home." I started to say. "I thought I could get a quick shower before you woke."
"That's okay, Mr. Niles" Christie said with a semi smile. "I hope you didn't mind me looking for you in the bathroom?"
Not sure how to answer that, I tried to sound nonchalant, "Oh, not at all. I hope I didn't scare you taking a shower."
"You didn't scare me. Although…"
I coaxed her on, "Yes…" Not knowing where she was going.
"Well, … my girlfriend was telling my about the sex encounter she had with her boyfriend and… I… wanted to know if all men are as big as you?"
I was stunned by her boldness. This was a side of her that I never knew. Now, I'm not that big; maybe 7" fully hard. But she asked and I have always had such a friendly relaxed relationship with her. "Men's penises are all different sizes, Christie. Mine is average size although you only saw it about half the size."
"Really!!!" Christie screamed a little louder than she wanted. "You get bigger?"
This was heading down the wrong road. "Yes, I do. It can grow to about 7 inches." Feeling a little bolder, I asked, "Christie, what do you know about sex?"
She seemed happy that I asked her that. After a second of thinking, she said, "Well, I heard from my girlfriend that she let's her boyfriend slide his thing into her and it makes her feel so good. She even told me that he sticks it in her mouth."
Now she was getting a little red from embarrassment. It was obvious that she has never had any type of sexual experience. She did seem a little hesitant to say any more, but after a few seconds of being quiet and me not saying anything, she continued, "Once, my girlfriend stayed over my house. While she was over, she showed me her privates and pointed out where her 'button' was. I was so entranced by it I actually touched it and she moaned. I thought I did something bad, but she asked me to do it again and just rub. I did it for a few minutes and she moaned louder. Finally, she let out a little scream and her button area got real wet." "After a few minutes, she told me that she had just cum and it felt great. I didn't know what I did, but she seemed to like it and asked me if I wanted her to do it to me. I was too afraid that it would hurt and told her no, maybe next time."
I could see that she was really flustered by telling me this and it didn't help that I had a serious hard-on in my shorts. I was sitting just right so she could not see it. I thought to myself that I need to stop it here and now, but my dick was aching and begging for something, I asked Christie, "Haven't you ever had an orgasm?… Haven't you ever cum?"
"I don't think so." She said.
"Do you want to?" I asked and continued, "How would you like to feel the excitement that your friend felt?"
She nodded and I asked her if she wanted me to help her with that orgasm. She just smiled. I was going over the edge.
I told her that she needed to be naked and before I finished telling her, she was standing in front of me in her birthday suit. Her smile was bigger than ever and I was finally getting to see her beautiful body. It was so innocent looking and her skin was a very soft white with a hint of color. Her small tits with little nipples accented her body and her pussy was covered with very sparse hair. She looked like a little angel. I asked her to turn around and I admired her pert little ass. For a little young woman, her ass had the perfect curves to it. Why did she wear bathing suits that were too big?
Not knowing where I was going from here, she asked; "Can you take off your shorts too??" Her innocence was present in her voice.
I nodded and led her to my bedroom where I took off my shorts. Her eyes were transfixed on the sight of my hard cock sticking out at her. I led her to the bed and laid her on her back. As she got comfortable on the bed I told her to just relax and watch what I did. She propped up a couple of pillows on her head as she watched me spread her legs open. I let my hand slowly caress over her mound and she smiled. With both hands, I spread her pussy lips open and found her clit. Her lips were already wet and her clit was big for her body size. "This is your button." I told her as I pointed it out. "It is also known as a clit. It is very sensitive and if you rub it right, it will make you cum. Here… watch…"
I proceeded to caress her clit and she started to moan with a little excitement. I started rubbing a little faster and she was breathing harder. After a minute or so, she claimed, "Oh, I think… I'm gonna….pee…"
As soon as she said that I rubbed her clit fast and she let out a little scream of excitement. I waited a few minutes to let her come down. When she was breathing somewhat normal again, I told her that she had just experienced her first little orgasm.
"Little?" she said. "That felt so great and so much! Wow, now I know why Kim likes it so much."
"How would you like to feel it again?" I asked. "I can do it a little different way if you want?"
"Yes…Can you do it again? Please!!!"
I told her to close her eyes and just enjoy it. When she was relaxed, I started rubbing her clit again like before, but when she hit her labored breathing again, I stuck my tongue in her pussy and her eyes shot wide open. I let my tongue roll up and down her lips. She tasted so sweet, almost like honey candy. Her breathing was getting so hard and she was definitely on the point of a much larger orgasm. I left my tongue roll up at then I hit her clit and I sucked it in my mouth. She screamed!
I sucked her clit into my mouth over and over and she was cumming over and over. Finally, I had to stop because I thought she was going to stop breathing. I let her come down a little and when she could talk she said, "Mr. Niles, I have never felt anything like that before. It felt like my whole body was in a frenzy and went limp. That was the greatest feeling…" She put her head back on the pillow and I went to the kitchen to get a drink since it had been a long time since I ate a pussy like that. I also wanted to clear my head a little because I was living a true fantasy.
I came back and she was relaxed on the bed. I was about to tell her that she can have the guest room tonight since her parents wanted her to stay over, when she asked me, "Mr. Niles, can I do that thing to you Kim does to her boyfriend?"
Not sure what she was referring to and not really caring since my cock was so rock hard and ready to burst. I said, "Sure, if you like. But what do you want to do?"
"I want to try to put your thing in my mouth."
"Oh, you want to suck my cock?" I asked to confirm my suspicion. With her nodding I sat back on the bed and set her between my legs and positioned her so I could watch her take my cock in her mouth. "Since you never did this, I will show you how you need to do it. Have you ever eaten a Popsicle? Or a lollipop?"
"Oh, sure. I love Popsicles. I eat them all the time."
"Okay", I said. "What you want to do is lick my cock like you lick the sides of a Popsicle. And then every so often you want to take the top of my cock and suck the whole thing in like a lollipop."
She looked at me and smiled as she grabbed a hold of my cock. Not knowing what to expect, she held on to it pretty good. As she let her tongue lick it, she started out too fast and I told her to lick it slowly. She did it. She did it for a little while and I thought to myself that for a first time cock licking, she was doing pretty good.
"Why don't you try taking it into your mouth?" I asked.
"Okay" and with that she took the head of my cock in her mouth and gagged a little. But she was determined to do it, so she continued taking a little more each time. Further and further she was going down on my cock. When all of a sudden she was about half way down on my cock and I felt her teeth bite into me and my eyes exploded with a little pain and a lot of lust. It felt great as she used her teeth. I've never felt that before and this first time cocksucker was bringing me to cum very quickly. Needing to stop her soon or she was going to get a big surprise, I asked her if she would like to try more.
"Am I not doing good?" She asked. "Kim's boyfriend tells her to keep going until he creams in her mouth. That's what I'm suppose to do? Right?"
Wanting to cum in her mouth, but wanting to take her virginity had me in a tough spot. So I told her, "You are doing great and if you keep this up much longer, I will cum in your mouth and it will be a lot of cum. However, I was going to ask you if you wanted to try anything more?"
"Will you fuck me?" Christie exclaimed as if she hit the lottery. "Will you take my virginity? Please!!!"
Not wanting to disappoint her, I smiled and set her on the bed and spread her legs open so I could position myself at the entrance to her virgin womanhood. Her smile was beautiful and the excitement on her face was priceless. I explained to her that it might hurt a little at first, then she would have waves of pleasure. She nodded me to continue. I positioned my very hard cock at the entrance of her very wet pussy. I rubbed my fingers all around her pussy lips and clit and she moaned to my fingers working her pussy. Taking her pussy juice and rubbing it on my cock, I brought my head to her lips and rubbed up and down slowly. She started her labored breathing and I pressed in a little. She was extremely tight. Tighter than any pussy I had visited. I barely got the tip of my cock in and she was screaming with pain. I pulled out and pushed in again not getting in much further. Her cry was getting to me and I thought about stopping; but I wanted her virginity bad. I pulled out again and this time I pushed in hard and got my head past her pussy lips and she let out a scream that I thought was going to wake the kids. I thought I could feel her hymen stretching as I pushed. I couldn't get in further, so I pulled out again and whispered to her, "Here it comes, honey. Be ready."
Then I slammed it into her as hard as I could breaking through her virginity but only getting three quarters of my cock into her. Her scream shook the house. "Oooooowwwwwwww…"
Then the tears poured from her eyes. I didn't move for a few minutes as Christie gathered herself and seem to be relaxing. Finally I started slow in and out fucking her pussy she seemed to be taking it well. I started giving her longer strokes and she was getting into it.
"How does it feel?" I asked.
"It really hurt first, but it feels warm and nice right now." She said smiling. "Keep going…I like this feeling."
I fucked her with long strokes. Although I could only get three quarters of my cock into her she was really getting excited. Each stroke I pushed in her further hoping to get it all into her. She was gripping my cock like a vise and I was on the verge of cumming. I was just about to shoot my load so I started to pull out of her completely to shoot my cum on her tits when she let out a wail.
"Ohhhhhhh…myyyyyyy. It's cummmmminnnggg aaaagain!!!!"
I couldn't stop now, so I slammed into her hard and fast. She continued to scream as she was cumming hard on my cock. Just as she was peaking, I let out a scream of my own as my hot boiling cum shot into her virgin pussy.
"Ohhhhhhhh….. my cummmmm!!!!" Was all I could say.
I fucked her so fast with my cum shooting in her that her own orgasm was still going strong. Finally I slowed down and she was coming down from her high. I left my cock planted in her while it shrank.
She hugged my with tears in her eyes and we stayed that way for quite some time. Then, she looked in my eyes and said with her own innocent look, "Thank you Mr. Niles. Thank you, thank you. That was better than I thought it could ever be. I never thought it could feel so good."
"You're welcome Christie. I'm glad I could be a part of your life." I slid all the way out of her and looked at the mess on the bed. It was soaked with cum and a little blood from her pussy. The enjoyment, the excitement and the shear satisfaction were incredible and I was feeling all of it. Until a slight feeling of guilt was hitting me for the fact that I had just fucked the young babysitter. Before I could get to far on that thought, Christie spoke up.
"Can we take a shower together?"
Smiling, I took her hand and lead her to the shower. She hopped right into the warm shower. I followed her in and before I knew what she was doing, she grabbed my cock and was rubbing it to bring it back to life. I had never come back to life that fast as it grew in her hands. When it was almost there, she got up and gave me a hug. From there I picked her up and planted her right on my cock. It went into her much easier this time, but she was still tight. As the water cascaded down our bodies, I pressed her on the side of the shower and began fucking her with strong upward thrusts. It seemed that she started cumming on the first thrust as her moan in my ear was sweet music. I was thrusting up in her as I had my arms around her waist and on her soft ass pressing down on my cock. I finally was in her pussy all the way. With her back pressed on the shower wall, my cock all the way in her tight pussy; I let my finger slide over her pucker hole on her ass and caressed it slowly. Christie was still on a high, I thought she was still cumming as I slid a finger in her ass. It went in very easy. Liking this feeling I decided to finger her ass and fuck her hard and fast. Since she was so light, I was able to bounce her easy to my fucking motions. It wasn't long until I came in her for a second time. Although, there wasn't as much cum shooting in her, the feeling was still incredible.
I was finally spent. Cumming twice in the same night hadn't happen since my college years. Christie was in ecstasy. She was feeling great and her smile was larger than I have ever seen from her before. We washed up in the shower and went to the bed. While I went to get us a quick drink, Christie changed the sheets. We jumped into bed together and hugged each other as Christie fell asleep. My mind was in a pure fantasy fog as I thought how much of a dream this felt like. I was so exhausted as my eyes closed and I drifted into slumber from the most incredible night.
Thinking I was dreaming. I opened my eyes to a beautiful sight of Christie sucking on my cock. Still a little clumsy, she sucked away. When I realized I wasn't asleep I looked up at her and she looked at me with her eyes transfixed on me. It felt soooo good. No matter how bad she was doing my cock, I was enjoying Christie. It didn't take to long when I moaned to her.
"I'm gonna cum, honey. You keep sucking hard like that and I will let it all go."
She just looked at me with those eyes and she sucked harder and rubbing her teeth on my cock.
I let it go. "Ahhhh….. I'm cummmming!!!" As spurts of my hot cum shot in her mouth.
I heard her gag a little and it went in her mouth but she didn't give up. Sucking away. She couldn't take all of it as a little cum dribbled down her chin but she had her taste. She let my limp cock go and came up to me and said, "That was different. Salty, yet… something. I think I liked it." She hugged me and we faded to sleep again.
In the morning we got up before the kids. Although I had thoughts of taking her again, I knew the kids would be getting up very soon. We met in the kitchen and she was dressed to go home. Smiling she gave me a big hug and said, "God!!! My legs hurt. I'm so sore, but it felt great!"
"Thank you for everything, Mr. Niles."
"You're welcome, Christie. I'm glad you enjoyed yourself." No guilt in my voice and feeling like I accomplished something. Her glowing face made me feel good.
We packed the kids in the car and took Christie home. When she was getting out she turned to me and gave me a quick hug. Smiling, she said, "Wait till I tell Kim about last night."
Stunned and afraid to let anyone know what we did. I said to her, "Do you think we should tell anyone about what we did?"
"Oh, that will be our little secret. But, Kim is my best friend and she won't tell a soul. I trust her. It will be just between the three of us."
Still a little hesitant about it. "Okay, if you think that is best." I knew Christie would be quiet about it.
"You never know, Mr. Niles; Kim may be so excited about it she may want to join us the next time I have to baby-sit again." And she closed the car door and hopped up to her house. Leaving me there to wonder…
My cock started to grow again at the potential thoughts.