Date: Sat, 22 Oct 2016 01:52:38 +0000 (UTC) From: ShortStories@PlayTime69.e4ward.com Subject: Babysitting Job Chapter 2 - (b/B/F, Bb, BF, 1st, anal, ped, Teen2) (b/B/F, Bb, BF, 1st, anal, ped, Teen2) This story is 100% fiction and is for mature readers only. It is a fantasy involving sex acts of children and an adult. 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. Babysitting Job (Losing My Virginity) by: Playtime69 Dave's mom was so glad I had been watching him after school, when there was no school, and some Saturdays that when summer came she wanted to do something special for me. It was about the same time summer vacation started the apartment complex they lived in opened their swimming pool. Cathy, that was Dave's mom's name, invited me over on a Saturday for a swim and dinner. She had already asked me to stay with Dave each day during the summer so she could keep her job. She was going to pay me more but not near what she would have to pay for a day care center. Let me take a break from the story to describe Cathy. She was only 27 years old. She had got pregnant when she was 17 but Dave was born just shortly after she turned 18. She was better looking than a lot of the girls at school and a whole lot easier to talk to. Her breasts were a nice 36C and very firm. She had long light brown hair usually pulled back into a pony tail. She was a nice 5'3" tall with a small hot looking butt. I was now 16 years old with Dave being 9 and still very cute for a boy. We continued to play with each other masturbating, oral sex, and he even fucked my butt hole from time to time. I was still a virgin because I did not have time to date. I was now allowed but watching Dave each day I did not get out much and since my sexual appetite was being quenched by Dave I really did not care. I did on the other hand enjoy seeing Cathy each night when she got home. She was always dressed nicely and just the look of her body gave me something to dream of when I was in bed at home. I would jack off to the thoughts of what her pussy looked like and wondered if she shaved her pussy hair or if she let it grow. I would masturbate each way but found her hairless pussy got me off faster. "Do not forget to be here about 10:00 tomorrow morning and do not forget to bring a swim suit." Cathy said with a smile. "Ok. I cannot wait. It has been a while since I got to swim in a pool and really miss it." I responded as I left their apartment Friday night. That night I showered and masturbated in bed dreaming of Cathy's shaved pussy and wondering what kind of a suit she would be wearing the next day. Saturday morning I was up and dressed in my swimming suit under my shorts as I sat in the kitchen eating breakfast. "I see you are ready to have some fun today for a change. I am glad you have been helping Cathy out and am really glad she is letting you be her guest at their apartment pool." My mom said as I ate. "Me too. I am glad I can help and Dave is fun to be around anyway. I think he likes having another guy he can talk to about things." I replied. We talked about school and other things as I ate. It was getting late so I finished up and headed out the door. I got to their door right at 10:00. We all headed out together with towels in hand to the pool. There was a few other people in the water and some just laying out. We picked some chairs to put our stuff on and off came the shorts and shirts. Dave was wearing a little pair of spandex swimwear and I had mine on but since I was older and bigger mine was not quite so small or tight. Cathy slipped her shirt off and then her shorts and for the first time I got to see what a real woman looked like up close. She had on a pink two piece bikini. The top covered her pretty well and the bottoms covered her slit and butt crack but not much else. I could not help but stare at her body as she stood in front of me. I am sure my mouth was open as my pecker started growing. "You might want to think about something else before you show more than you need to in public." Cathy said as she looked at my crotch. "Oh, sorry. I. Ummm..." I mumbled as I turned and jumped in to pool. I quickly found Dave and started playing with him with some of the toys floating in the pool. We talked about how hot his mother looked and how much I wanted to cum in his mouth. I think he knew I really wanted to cum in his mother's cunt but was afraid to say so. It was not long before Cathy jumped in the pool and was playing with the two of us. I could feel her brush up against my cock from time to time but was not sure if it was on purpose of just by accident. It did not matter as I enjoyed it either way. We were at the pool until about 3:00 when we decided to go in and eat. We were all pretty much red from the sun and all wrinkled from the water but we all had a lot of fun. We all showered at the pool before leaving so when we got back to the apartment we were all still wet. "Let's all get into dry clothes and eat. It will not take me long to fix dinner then maybe we can watch a movie together if you want to stay." Cathy mentioned as she headed off to her bedroom to change. I went into Dave's room where we both stripped. My cock stiffened up as I looked at Dave's naked body. He saw my cock and smiled and said he wished we could play but with his mother in the next room it was too dangerous. We got dressed and went to help in the kitchen. When I walked into the kitchen I must have had the same look on my face as when I saw Cathy in the swim suit the first time because she made a comment about my cock busting out of my shorts. She was now wearing the tiniest white shorts I had ever seen. There was almost nothing to them. Her top was simply a half shirt with no bra. Dave paid no attention to what she was wearing like it was normal. I was able to get him out of the room so I could ask him if what she was wearing was normal. He giggled and told me that what she had on was more than what she normally wore around the house. When I heard that my mouth dropped open figuring Dave might just know if her pussy hair was shaved or bushy but before I could ask we hear his mom call that it was ready and for us to get in the kitchen to eat. I ran in and sat down to eat. The meal was plain but very good. We chatted about different stuff but eventually got to a discussion of what we did after school each day. We just said the normal stuff leaving out the sex part. We finished eating and had desert and once that was done we headed off to the living room. We were on the way when all of a sudden Cathy asked, "Mike, what is your favorite position to fuck Dave?" I must have turned white as I could feel all the blood rush from my head. I could not say anything even if I wanted to. I just froze and stood there in the hall like a deer in headlights. Cathy asked if I was ok. I just mumbled something not sure what but she finally let me know that it was ok. She told me she had found dried cum on some towels and some of Dave's underwear. She also told us she figured Dave was not shooting cum yet so figured it was mine. When I finally figured out I was not in trouble I said, "Um, well, I really like it when my cock is between his legs and his cock rubs my skin. I like shooting my cum on his back and butt crack. I guess it is a feeling close to having sex." "That sounds like fun. Are you still a virgin?" She asked. I looked down not really wanting to answer but finally did. I told her I was still a virgin and figured Dave's butt hole was too small to put my dick into. I explained how we like sucking each other's cock and how Dave had not started shooting cum yet. I told her how he did have the feeling of cumming just not the cum yet. I admitted we did have sex in one form or the other most every day. I could tell she was enjoying my talk as I saw her hand slip to her pussy. During this talk we moved slowly to the living room and sat on the couch. Dave was not saying much but I could tell he too was enjoying the talk as I could see a little bulge in his shorts. Finally Cathy said, "Mike, how would you like to fuck my pussy?" "I. Um. Well, um. I guess so but what about Dave? Dave is that ok with you?" I asked. "Can I watch?" Dave then asked. I looked at Cathy to see if it was ok with her. She nodded her head yes saying she would love for him to watch. Then she did something I thought would only happen in my dreams. She reached up pulling her half shirt off revealing her perfect breasts. My mouth opened as I could feel my cock jump to attention. She smiled at me as she pointed to my shirt. She told me I was way over dressed and for me to strip naked. I went for it taking my shirt off first then my shorts and underwear. I was totally naked in front of an older woman. Dave too was naked without being told. The only thing left was Cathy's shorts and panties and in one swift move she was bare and for the first time I have the answer to my question. Her pussy hair was not shaved but was not hairy either. It was trimmed very nicely in a wide strip but yet the pussy lips were shaved as close as a new born girl's pussy. My cock was straining against its own skin to get larger as it grew bigger than I had ever known. Cathy told me to lay down on the floor where she have placed some blankets and pillows. She then mounted me. My cock slowly entered her steaming hot snatch and her eyes glued to mine as we faced each other. She was watching to see what gave me the most pleasure. When my cock disappeared inside her cunt I instantly felt my cum wanting out. I had to tell myself not to cum at least not just yet. "Fuck me back as my pussy sucks the cum from your balls." She demanded as she pumped her pussy up and down on my dick. I did as requesting only making it harder not to cum. I thrust my hips up forcing my dick to penetrate deeper into her pussy hole. I looked over to see Dave intensely watching as I fuck his mother. He did not look upset matter of fact he looked like he was enjoying the show. His little cock hard as a rock and sticking straight out in front of his body. I reached up taking hold of his little cock where I started stroking it to make him feel good. The more I fucked Cathy the more she fucked me back and the more she fucked me the faster I jacked Dave's little cock. This was just a fucking frenzy as I could no longer hold it. "I am going to cum in your pussy." I said out loud to Cathy. "Yes, fuck my pussy. Give me your virgin cum! Make me your little slut girl. Come on and blast that load of yours inside my pussy." Cathy yelled as she watched me fondle Dave's cock and balls. With that I blew my load. Cathy put all her pressure on my body as she sat on my cock. She wiggled her butt which ground her wet cum filled cunt into my privates. I could feel her pussy contract around my shaft then all of a sudden I could feel wetness from her hole as she expelled her own liquid orgasm all around my cock. "Wow, that so sooooooo good." I mentioned as my breathing was returning back to normal. "I am glad you liked it but now it is Dave's turn. Do you mind if he fucks your butt hole while I watch?" Cathy instantly asked. It did not even take a minute before I was on my hands and knees ready to accept his dick in my ass. I looked around to see Cathy sticking her fingers inside her cunt then taking the cum and sliding it inside my hole. She did this several times before telling Dave to enjoy fucking my butt hole using mommy's cum as a lubricant. Just hearing what she was saying was getting me hard again and I already was hoping to fuck her again before I had to go home. I felt a little pressure then pleasure as Dave's cock penetrated my puckered butt hole. He pounded me hard for a few minutes then his little body shook and tensed up. He had just had another dry orgasm and was loving the afterglow. When he pulled out I immediately asked if I could fuck Cathy again. "I guess you liked it the first time?" She replied. I nodded my head, 'yes'. She laid down on the floor and I climbed on top forcing my hard again cock into her soaking wet snatch. I pounded hard and fast and within five more minutes I had cum a second time. We got up then all went to the bathroom together to clean up. She washed my cock and dried it off then she did the same to her son. She then forced us to watch as she cleaned the cum from her own pussy. When we were all done I got dressed and left hoping this was going to be a normal thing to happen each night. It did not happen every night as she was usually too tired but on occasion I did get to fuck her. I did get all the sexual activity I wanted from Dave, her son. We even played together from time to time. The one thing I never got to see and am not sure it even happened was Dave fucking his own mother. If he did I never found out about it. The End