Date: Thu, 13 Oct 2016 02:37:40 +0000 (UTC) From: ShortStories@PlayTime69.e4ward.com Subject: Babysitting Job - Chapter 1 - (b/B, Bb, 1st, oral, anal, mast, ped) (b/B, Bb, 1st, oral, anal, mast, ped) This story is 100% fiction and is for mature readers only. It is a fantasy involving sex acts of children. You can see a list of all my stories on the authors page under the author, Playtime69. Comments are appreciated at ShortStories@PlayTime69.e4ward.com. Even though I do not respond to your emails I do read them all and have used some of your suggested ideas in my stories. I also will write new stories with your suggested ideas. Just send me your ideas to address above with as little or as much information as you want to tell me including names, ages, sexes, positions, relationships, and what section on Nifty you want the story to go, etc. I will see what I can do with it. If you want to name the story that is fine too. Just make sure the information is yours and not from someone else's story. Thanks for reading. Please, find it in your heart to donate to nifty at http://donate.nifty.org/donate.html without them we would not have a safe place to deposit and read such great stories. My First Babysitting Job (Dave and I Become More Than Friends) by: Playtime69 There are several things we remember as adults from our childhood. One of those events is the first job. When I was 15 years old there was a new employee where my mother worked. My mother became good friends with the woman which had a young son. Her son's name was called David but he went by the name Dave. Dave was 8 years old and a very cute boy. His body was petite and had more of a feminine look than a masculine look. Since his mother was not married he was growing up with only a woman in the house so was brought up more as a girl than a boy. He did wear boy clothes but that was the only way you could tell he was a boy. He had fairly long light brown hair and a cute smile. He wore mostly light color clothes like yellow, blue, and green unlike a boy wearing blue jeans. My mother came to me not long after they had become friends and asked me if I would be willing to watch her friend's son after school each day so she could work later. My mother told me that I would get paid but not as much as what I would be getting from someone else because she did not have much money and was having problems being able to pay the rent and buy food. I agreed and did not argue about the money as I felt sorry for the woman. I really did not need the money anyway because I got whatever I needed anyway. Things were set and I would walk over to their apartment after school each day and would get there just as he got home from school. I would then stay there until his mother got home and would walk home. Good thing we did not live too far away. Guess I need to add some information about myself. I am 15 years old and my name is Mike. I have brown hair that is not long but not short either. I was a typical teenager. I loved rock and roll, all sports, and of course girls. It did not take much for my dick to stand at attention when I saw a girl in a bikini. My dick was a respectful 7" long when I got hard but was not too big around. It was not skinny like a pencil either. I was about 5'6" and weighed 130 pounds with very good muscle tone. I did not have a girlfriend but was not afraid to talk to them either. I was still a virgin as I was not allowed to date until I turned 16. I had been jacking off every day or two for the past two years and had no thoughts of quitting. The first few weeks were a lot of fun. I would get there right before he got home and when he got home I would help him with his homework then we would go outside and play ball. I taught him about baseball, football, and some other sports. I would fix him a snack and we would end up watching TV while snacking on chips, popcorn or other items I could find. It was usually 2-3 hours before his mother got home and when she got home I would leave. Something came up at his mother's job that caused her to have to work real late for a week. I am not sure what it was but I was just told she would not be home until about nine at night. Dave was to be in bed at eight so I was responsible to fix dinner and get him to take a bath and get into bed all by his bedtime. It was not big deal as we had become good friends and we were both guys so I did not even think there would be a problem. It was only temporary so I was going to do my homework after he got into bed. One good thing was my father would pick me up each night so I did not have to walk home in the dark. Monday came and I was at Dave's apartment just as normal. Dave got home and I helped him with his homework. When we were done we went outside and played catch a while and then back inside. I told him he was to take a bath then we would eat and if time some TV but he had to be in bed by 8:00. He finally agreed and headed off to the bathroom. I ran the bath water and he took off his clothes and got into the tub. I left him alone and started dinner. When I got back to the bathroom I found him clean and ready to get out. When he stood up I noticed he had a boner. His little cock was sticking straight out from his small nut sack. His hard cock looked to be a little over 3" and for an 8 year old that is pretty big. He did not have a single hair on his body other than the top of his head. I could not help but stare at his hard dick as he dried himself off. "Mike. Mike!!" Dave yelled trying to get my attention. "Huh? What? Oh. Sorry." I mumbled. "What you staring at?" He then asked. "I. Well. Ummm. I was just looking at your cute hard cock. I have never been interested in guys before but your cock is so cute and without hair it is really something I find interesting." I admitted. Dave giggled then said, "Mom likes it too. She said I will make some girl really happy when I grow up." "Do you get hard in front of your mother?" I asked Dave. He giggled again then answered, "It gets hard a lot especially when I take a bath and when I get up in the morning." "Can I touch it?" I begged not knowing what was drawing me to get involved with another guy especially with one so young but I was somehow attracted to him and his cock. "I guess so. Never had anyone else touch me before." He answered. I was amazed he was still hard after all the time we spent talking and with him standing drying off. I reached down and put my hand around his smooth hard little cock. He jumped just a little but quickly got use to my hand as it wrapped around his shaft. I started stroking it like I did my own cock when I masturbated. I was not sure what I expected but was basically wanting to make him feel good. He moved around a little like he was trying to get away. I asked him if he was ok and he let me know he was it was just a funny feeling. He soon got use to me stroking him and was soon pumping against my hands. "Can I see your weewee?" Dave asked me. "Sure. You can touch it too if you want." I replied as I dropped my pants and underwear. My dick started out semi erect but within seconds of my pants hitting the floor and Dave's little fingers touching me I was hard as a rock. He started out playing with my shaft and moved to my heavy balls. He then progressed to stroking me like I was stroking him. He did as I did so the faster I stroked him the faster he stroked me. Finally, I had hit the point of no return and told him I was about to cum. Dave did not know what I was talking about but he soon found out as I shot my cum across the bathroom floor. I put my hand on his to stop him from stroking because of the intense feeling. "Are you ok?" Dave asked as he looked at his cum covered hand and floor. When I could speak I said, "Yea. I am fine. That was so good. Thanks. But, I do not think we need to tell anyone what we did including your mother." "Ok. Can we eat? I am hungry." He replied. We got cleaned up and dressed then went to the kitchen. While I finished up dinner we talked about masturbation and what had happened in the bathroom. We continued the talk while we ate and then cleaned up the kitchen still talking about sex. We went to the living room to watch TV but instead we talked about the ways guys have sex together. I made it clear that I was not gay but was just curious and if he was interested we could learn together. He was more than willing to play some sex games. I looked at the clock and noticed it was time for him to get into bed. We went to his bedroom and Dave got into bed. Without thinking I leaned over and kissed him on the mouth while reaching between his legs giving his little cock a loving squeeze. "Sleep well. We will play some more tomorrow night." I said. "Ok. Thanks for being my friend." Dave replied. I smiled and patted him on the head to let him know I felt the same. I closed the door then went to the living room to do my own homework. I worked on homework but really did not know what I had done as all I could think of was Dave's cock and what we were going to try the next night. His mom showed up and my father came and picked me up. I got home and finished my homework. I took a shower and got into bed. All I could think of while in bed was Dave and his young cute naked body. My hand slipped down to my dick and began stroking. Within minutes I came. I cleaned up and fell asleep dreaming of what the next day would bring. The next day started just like all the others. I got to Dave's house just before he got home and when he got there we did his homework. It was hard for me to concentrate as my mind was on his dick. He did not seem to have any thoughts of sex as he was not saying anything and was able to do his homework better than I was. My cock was up and down as I planned what to do when I got the chance. I actually could feel the pre-cum oozing from its tiny slit. When we finished his homework I asked him if he would like to play something new inside. He wanted to know what game so I said it was something like what we had done the day before. For the first time he smiled and was interested to hear more. "The first thing is you will need to take a bath to get your little pecker all clean. If you do not mind I will get in the tub with you so I too can get clean." I suggested. He smiled again and said, "Yes, that sounds like fun." We headed to the bathroom taking our clothes off as we walked and by the time we got to the bathroom we were both naked. I filled the tub with warm water and we got in facing each other. He reached over and grabbed my growing cock and I reached over and grabbed his. We rubbed each other making each other's cock grow to their maximum length. I do not know about Dave but I was so close to cumming I had to stop him before I erupted. We finished up and dried off. I took him by the hand and led him to his bedroom where I had him lay down on the bed. I then climbed on top but placed my head between his spread legs and placed my cock above his mouth. I told him to open his mouth and let my dick find its way inside his warm mouth. I took his cock inside my mouth and lowered my dick into his. I pumped his cock in and out of my mouth as I thrust my cock in and out of his hot mouth. We were pumping hot and heavy in the '69' position both enjoying the feel of a cock in our mouth and also our cock in another mouth. It was like having double pleasure. His cock being so small I was able to also slide his balls in my mouth along with his cock. I sucked hard and in a short time period I felt his body tense up and shake before going limp. He had just had an orgasm. It was a dry one as he was not producing cum yet but the feelings were still there. I was not far behind but I warned him to relax and not to swallow. I told him to just let the warm liquid flow down this throat. I was pumping his face with my cock with my balls slapping at his nose and face as I fucked his mouth. I could hold back no longer and let go with several hot streams of cum. The little eight year old boy took all the cum I had and did so like he had been having oral sex for years. Once my balls were drained I dismounted his face telling him how much fun I had and how I hoped he had enjoyed it also. He said he loved doing it and would like to do more in the future. We cleaned up a bit and walked to the kitchen to find something for dinner. We both decided to stay naked until he had to go to bed. We ate and then retired to the living room to watch some TV. We cuddled together as we watched a show but our hands roamed over each other's body and before Dave made it to bed we had both cum one more time. I knew it would be a few years before Dave actually shot cum and was really hoping I was going to be there the first time he did. Dave got dressed for bed and climbed under the sheets. I too got dressed and went to do my own homework. This time I was able to concentrate better as I knew we were now on our way to an open sexual relationship and that I was going to be able to do anything I wanted. His mother showed up and I was home in bed before I knew it. I did not jack off again as I wanted to build up some extra cum for my new sex boy toy. Wednesday arrived with me at his place as he got home from school. Dave went to the bathroom and then to his room before coming to the living room to do homework. This was normal but what was not normal was he was totally naked when he walked in. His little cock sticking straight out as he bounced into the room. I looked at him and smiled. "Cute, but we have to do homework before we 'play'." I said with a tone of disappointment in my voice. "I know. I just like being naked around you. If you want you can take your clothes off too." He replied. I could feel my cock pressing against my shorts and the thought of letting it free was very inviting. The look in his eye told me he really wanted me naked too so I pulled my shirt off and my shorts and underwear came down in one swift move. We sat on the couch side by side working on homework with our cocks rock hard. He would reach over and touch me and I would reach over and touch him but we worked on homework until it was finished. He took his books and put them away. He returned to the living room to find me stroking my cock. "Stand by the couch and I will be right back." I told him as I walked to the bathroom. I grabbed a couple towels and some lube and walked back to the couch. I placed one big towel on the couch and laid down on it. I lubed up my cock and then lubed his cock and added some between his legs. "I want you to climb on top of me and I will put my cock between your legs. Your cock will be rubbing on my pelvic area while my cock rubs between your butt cheeks. You will need to put your legs together tight and when I get it in position you will need to hump your cock against me." I instructed him. He did just as I said and was fucking my dick between his butt cheeks. I could feel his hard little cock with each thrust he made. I am not sure if I liked the feel of his cock or the feel of my cock on his skin better. I put my hands on each side of his butt and helped him pump up and down on my cock. I could feel my cum starting to flow from my balls and I lost control. I started fucking him back. Our bare skin was slapping each other and with the lube made a loud sexy sound. I thrust up as Dave thrust down and his legs gripped my cock like a vice. "Fuck, Dave, I am about to blow. Yes!!! I am cumming...Fuckkkkkkkkk!" I yelled as my cum shot from my dick head. My cum coated his back as I tried to catch my breath. His little pecker to was throbbing like it had just shot a load as big as mine but since he still was not shooting cum it was just going through the motions. I could tell he had just had an orgasm even though he did not shoot. When I could talk I told him to slide off me to the couch but to stay on his stomach. He did and I cleaned up the cum from his back. I told him I had about the best orgasm I had ever had. He smiled and said he liked it too. We got dressed and went outside for awhile. When we were tired we went in to eat then a bath and to bed. His mother got home and my dad picked me up. I got home and went right to sleep. Since I had taken a bath with Dave there was no need for a shower. The rest of the week went pretty much the same. We had a lot of oral sex, masturbation, and humping. I was cumming on or in his mouth at least once a night and sometimes twice. All week long I was sleeping really well because I was so sexually satisfied. It was almost like we were a couple. I was no longer looking for a girlfriend as I had no reason. I was having all the sex I wanted, I was getting paid to have fun, and still had all the freedom I wanted. Thursday night when Dave's mom showed up I could see in her face there was a problem. Thoughts raced through my mind like, 'Did she find out I was fucking her son?', 'Did she smell the cum soaked towels?', and 'Had Dave said something he should not have said?'. I did not know if I should say something or wait for her to say it. Finally, I said, "Is something wrong? You look like something is bothering you." "You are very observant. Yes, and I hope you can help me out. I just found out today I am going to have to work Saturday. I have to be there at 8:00 and will have to work until 4:00 or 5:00. I was hoping you could watch Dave for me. If you can you can just stay Friday night." She begged. "I do not have plans for Saturday and Dave and I are really good friends so, yes, I can stay Friday night and Saturday but I will have to ask when my Dad gets here." I answered. She looked relived giving me a big hug and kiss on the cheek. I could feel her breasts as she pressed them into me. I could feel my cock raising to attention as she hugged me and I was sure she could feel the hardness grow as she took her time breaking the embrace. When we broke she smiled at me and it was a different type of smile. It was an evil sexy smile. Thoughts raced through my mind as where would I sleep Friday night. Will she let me sleep with her or with Dave. Maybe she will just have me sleep on the couch. My dad showed up and I explained it to him. He told me it was fine so I went back in and told her I will plan to stay Friday night. "Where will I sleep?" I asked. "Well since Dave has a big bed you can sleep with him if you want. If not you can sleep on the couch." She answered. Well that answers that question. I will not be sleeping with her. Then I replied, "I do not mind sleeping with Dave." I got home and went to bed dreaming about what it would be like to sleep with Dave's mom and better yet sleeping with Dave and his mother at the same time. Friday arrived and all I could think of was sleeping in bed with Dave. When Dave got home I told him what was going on and he was as excited as I was. We decided not to do anything but play until we were in bed together. I explained that I was not sure we could do anything until the next morning because his mother might hear us fucking. He understood but still wanted to wait. That night we played outside and took a bath together teasing each other's cock every chance we had. We were both so excited it was hard to keep from getting right to the sex. "I am not sure I want to wait till morning to fuck you." I told Dave while we ate dinner. "Yea, I agree." Dave replied as he got up from his seat and put his face in my lap taking my full member in his mouth without any notice. He sucked hard but not for long before he returned to his seat smiling at me. "Fuck you." I said in a teasing sort of way. He just smiled at me and continued eating. I reach over and grabbed his hard cock and started pumping on it with my hand. I jacked his cock for several minutes and when I could tell he was just about to have an orgasm I stopped. I just looked at him and smiled. "Fuck you too." He then said in a playful tone. I had him in bed at 8:00 and his mother showed up around 9:00. She told me again how grateful she was and would make it up to me someday. I just smiled telling her I was going to bed. She took a shower and headed off to her own bed after checking on Dave, giving him a kiss goodnight. Once I knew she was out of the room and was not coming back I took off all my clothes and slipped in bed holding Dave. I reached over and pulled Dave's underwear off leaving him too naked. I spooned him with my dick pressed in his warm butt crack. I slowly fucked his crack. He did not move much and the more I pumped the more pre-cum that leaked out which made his crack even more exciting. This caused me to fuck harder and faster. He had made me so excited from teasing me that there was no way I could sleep until I came. I quietly fucked his butt crack as he slept. It took a few minutes but I finally got to the point I could not hold back. I came filling his crack with cum. I held him tight and drifted off to sleep as the cum in his crack dried. I am not sure how or when but sometime during the night we switched positions. He ended up holding me with his hard cock in my butt crack. The next morning when we woke up I looked at the clock. Without moving I told Dave that his mother should have already left so we could do whatever he wanted. I then got an idea and asked, "Would you like to fuck my butt hole? You know put your cock inside me?" "Yes." He quietly answered. I reached over and grabbed the lube that I had ready. I was not sure what we would do but I wanted to be ready. I reached around with some on my finger and rubbed it on my hole. I gave Dave some and told him to lube his cock up and to press it to my butt hole. When I could feel it in the right place I told him to push. I pushed back against him and it slipped in without much pain or trouble. I told him to fuck me which he did. He was pounding hard enough I could feel his balls slapping my skin. His fucking picked up and at one point I thought he was going to push me off the bed. He was really going after my hole and then all of a sudden his body tightened up and he grabbed me tight and shoved his cock as far inside my butt hole as he could. His body shook as I could tell he had an orgasm harder than he had ever had one before. "Thanks." Dave said as he backed out of my butt hole. I wanted so bad to plug my cock into his butt hole but I knew his was just way too small so I just had him give me a blowjob. I shot a huge load down his throat which he really enjoyed. We got up and ate breakfast staying naked until we knew his mother would be home. We got dressed right before she got home. When I got home I took a nap because I was totally exhausted from all the sex Dave and I had that day. The next week things got back to normal except we had a lot less time to fuck. We decided we would try to have sleepovers from time to time. But then again that is another story.