Date: Mon, 15 Jun 2015 12:30:34 -0700 From: Jitters William Subject: Sixteen and Babysitting my Neighbors D O N A T E D O N A T E D O N A T E Remember Nifty is only here because of donations from the readers I have added some stuff to this to make it "better", but for the most part this is what I remember happening back in 1986 I had only turned 16 just a few months before. It was New Years Eve 1986 when this takes place. But before I begin a little background on how we got there. Our neighbors had lived there for a few years. They were in their 30's and had two kids, a son Billy and a daughter Ellen. Billy was about 2 maybe 3 years younger than me and his sister was about 5 years younger than me. Just after my 16th (November) I was asked if I could babysit Billy and Ellen. They said it would be from around 7at night until 3 or 4 in the morning. It was Friday night and I had nothing to do. So I said sure. I was told they really did not need a babysitter, but felt better having someone at the house that could drive in case of an emergency. At a few minutes before seven I walked next door. Billy and Ellen were watching tv and their parents were running out the door. They left us with money for pizza and said they could stay up till 2am if they wanted. I sat down and watched tv until one of them said they were hungry. We ordered pizza and while we waited they went and showered and put on their Pjs. I had never really been in their house before so I wandered around and checked things out. I strolls down the hallway and as I walked by the first bathroom door, it was wide open amd Billy had just got out of the shower. He had his left foot on the toilet and was drying off. I just stopped and stared. He was so thin and his dick was really thin and longer than mine, but he had no hair at all. When he looked up I asked if it was okay if I showered after him. He turned and faced me and said, jump in I am just drying off. I said I would be right back. I went to the livingroom and grabbed my pjs. As I walked back to the bathroom I saw that Ellens bathroom door was open, so I wandered down to it to take a peek. I thought it was empty because there was no water running, but as I walked in I realized that Ellen was laying in the tub washing her hair. Her eyes were closed and she was laying there all naked. Now as a 16 year old boy my cock got hard just thinking about a naked girl and here was one in the flesh. She had just started getting here titties and her pussy was still smooth as my shaved nuts were. My cock went hard instantly. I turned around and headed to the other bathroom. Now I was in my swim trunks from sitting in our jacuzzi that day (It was a warm day but not quite hot enough to swim) My cock stuck straight out and it wasnt until I walked in and Billy was drying off still and stared right at my dick that I became all embarassed. He did not say anything about my boner, he just set his towel on the sink and showed me how to adjust the temp for the shower. When he turned to get by me his cock rubbed my leg and I looked down to see it was also getting hard like mine. Now I showered at school all the time, but NEVER did any of the guys have hard ons. I dropped my shorts and jumped in. I pulled the shower curtain and all I could think about was jacking off. I looked out to see if you could see through the curtain and figured the little bit he might be able to see did not really matter, I was sure he played with his cock too. I reached down and just touching my cock it pulsed and throbbed. I was so hard, it felt thicker and longer than its normal 4 ½ inches. I was slowly circling my cock head and pulling down my shaft. I was about to explode when I heard Ellen ask Billy if I would be out of the shower by the time the pizza showed up. Just hearing her voice I came really hard. I actually moaned a little and Ellen asked are you done. I could feel my face turn red with embarassment, I did not know if she meant had I cum or was I done showering. I said yes, I was about to get out. I pulled the curtain back a little and watched them wander out and down the hall. I jumped out and closed the door while I dried off. I threw on my flannel pj shorts that my mom sewed me and a t-shirt. When I got to the living room billy was laying on the carpet with pillows proping his head up against the loveseat. He had no shirt on and was in a pair of white cotton boxers. Ellen was sitting on the loveseat in some lacey panties and a t shirt. I started to sit on the floor when the pizza showed up. We ate and them all decided to watch a movie. Billy had layed back down on the carpet with a pillow. This left either next to him on the floor or sitting on the loveseat with ellen. I opted to sit on the floor next to him. Ellen went and picked out a movie and put it on. As she came back she plopped down straddling Billy and was kinda tickling him. He laughed and told her to stop. She kept up, but at the same time she was rocking back and forth. I sat there and watched her grind her pussy into his cock. Just watching this made my dick get hard again. She laughed and hugged her brother then stood up and jumped on the seat behind me. Now the only light in the room was from the tv, but looking over I could see that his cock was swelling up, not quite hard, but it was making a little tent. Looking down, mine was rock hard and if I had been laying down I would have been seriously tenting my pjs. But thank god it was dar and I was in more of a sitting position. Unless you stood infront of me, my hard on was pretty well hidden. It was then that my night became entertaining, I dont remember the movie, but about 40 minutes into it Billy had fallen asleep and I was on the verge myself. Then Ellen said her calf was cramping and asked if I could massage it, she said he brother normally does but she did not want to wake him. She offered to massage my shoulders if I did her leg. Before I could answer she had scooted forward on the loveseat and wrapped her legs around me, dropping her feet right onto my cock and balls. Then she started rubbing my shoulders and I thought, hey this is a fair trade. I asked wich leg and she said her left one. As I grabbed her left foot her right heal slid down my little shaft and came to rest on my balls. Just that little movement and I could feel my cock twitch and start to thicken. So I moved around a little thinking it would cause her foot too move away. But instead, the next thing I knew her right foot was literally resting on my shaft and cock head. Then I noticed that when I squeezed her calf muscle and slid my hands onto her left foot she would curl her right toes and basiclly stroke my cock. With each muscle rub, her toes stroked me one more time. After a few minutes my cock was so hard and throbbing against her right foot there was NO WAY she did not know I had a hard on. My cock was throbbing so bad and was in a bad position, I needed to adjust it. Just as I was about to say something she asked if I would rub her other leg. I let go and she placed it with her right foot and then slowly ran her toes down the length of my hard cock. I reached down and picked up both feet with one hand and adjusted my cock so it was pointing up and to the right. I set her left foot down off of my cock and started rubbing her right foot. It took about 3 minutes and her foot was against my balls between my legs. She said she felt better and wanted to know if I wanted her to stop massaging my shoulders. I was so caught up in her foot stroking me that I did not realize she was rubbing my shoulders. I said sure. It felt good. With that I let her foot go and dangle to my right side. She immeadately repositioned herself and stuck her feet back in my crotch. At first she just rested them there. But I was so hard and anytime my cock twitched she would lightly rub my shaft or balls lightly. She said her hands were tired and stopped rubbing my shoulders, but did not move and kept her feet on my cock I had started to watch the movie again and had scooted down a few inches, when I did this it opened up my crotch completely. She placed her right foot against my cock and wiggled her toes. She did not say anything. Just slowly massaged my cock with her foot. I had to pee really bad. So I said so. She lifted her legs and I went and took a leak. Of course with a raging hard on this took a few minutes. When I came back she was on the edge of the couch legs spread so I could sit right back were I was. As I got down on the floor I looked and her panties were deep in here little pussy and looked wett. I kinda laid down and she told me to scoot up. When I did my pjs slid below my butt. Before I could pull them up she had put her feet in my lap. I just laid my head back and when she started stroking my cock with her feet again I reached down and lifted her feet up and pulled my pjs down and placed her feet on each side of my cock. I did not have to say anything. I could feel her lean over me, I assume to watch as she jacked me off with her feet. I started thrusting up and down and the only thing she said was, your getting my feet wett. With that, I came all over her toes. She just kept rubbing all the cum all over my cock and balls. Slowly I stopped her feet from moving and she pulled them up onto the couch. Neither of us said anything. I pulled up my pjs and we fell asleep watching tv. We were woken up in the morning, their parents had come home and just let us all sleep. At breakfast they asked if I would be willing to babysit on New Years Eve for 2 nights. With my cock still wett and sticky from cum I did not hesitate to say yes. It was the longest 6 weeks of my life. I had jacked off at least twice a day thinking about what had happended. New Years had finially cum around. I wandered next door at around 5pm. Their mom and dad were still getting dressed. They said that I could sleep in their bed if I wanted or could crash on the couch. What ever I wanted. They gave me $100 to buy fast food for the two days and they were off. I had done nothing but think about Ellen getting me off for weeks. I had even gone to the thrift store and bought some really thin and baggy cotton shorts. If I put them on and walked around they literally would fall off if I did not pull them up every 8 or 10 steps. They were a light gray and so worn that even baggy they showed everthing I didnt have :) It was cold out so I turned up the heater really high, so I would have and excuse to wear nothing but the shorts. My cock was half hard all day and I had gone in the bathroom and jacked off twice in three hours. We had eaten dinner and were sitting around when Billy said he was gonna shower. He got up and left the livingroom. I had never been alone with Ellen before and was suddenly really nervous. She asked if I wanted to see her room. I said sure, as we walked down the hall Billy was laying in the tub, door wide open, cock and balls all exposed, reading a car magazine. She looked in, said hi, and then said Billy is starting to get hair on his weenie. If you ask him he will show you. Then she asked if I had hair on my weenie. I said I grow some but I shave it off, I like it smooth. She said maybe later after I shower I could show her, I said maybe. My heart started racing and my cock started getting hard again!! Her room was painted pink and really clean. She said that now that she is 11 she is really trying to keep her room neat. It was everything had its place. On a chair was a pair of gym shorts that looked too big for her, she said they were Billys, I asked did he get naked in her, she laughed and said no, he goes to high school now and they are the wrong color for gym class, so he game them to her. I asked if they fit, she said that they almost fit, but they fall down really easy. I said I had a pair just like that and that I use them mine pjs, maybe she should sleep in them. She said that was a good idea, and grabbed them and said she would put them on after her bath. She grabbed my hand and let the way out. Billy was drying off as we walked by and said the shower was open for me. I said thanks and went to the living room to get my shorts. I waited a few minutes after Ellen went to take her bath and then headed to take a shower. I could hear her shut off the tub water and started thinking of reasons to go in and ask her a question so I could see her naked. I decide I would ask for a clean wash cloth. I walked in and there were here tiny titties and tight little pussy, I just stared and then she said, take a picture it will last longer, I turned red and asked for a wash cloth. She stood up and walked over to the cabinet next to me, opened it and handed one to me. She smiled and asked if I needed her to wash me too. Jokingly I said sure cum in when your done. I left and got through the shower, I had just pulled on my loose shorts when she came in and asked why I did not wait for her. I laughed and said I was kidding. She said okay and stood there waiting for me. When we walked out she said, see I did what you said, im using the shorts as pjs. I reached over to her belly and pulled the waist to see how loose they were, they were as loose as mine and just like me she had no underwear on. I could see her pussy. She reached over and pulled mine out and looked at my dick and said yours are as loose as mine. She then asked if I could put her on my shoulders. She was about 4'4" and maybe weighed 60 lbs. I grabbed her and plopped her on my shoulders. When we got to the livingroom I had to put her down. She leaned forward and told me to lower her slowly. I was only in my shorts which had dropped down to where entire pubic mound was exposed, if it wernt for my cock being half hard, my pants would have fallen to the flooor. As she leaned over upside down, her middrift shirt dropped to her chin exposing her little titties to my face. To keep her from falling I grabbed her hips and lifted her. She grabbed my legs and started to pull herself down. I lifted her up which slid her shorts down a little and put her face just below my belly button. She leaned forward and gave me a rasberry on my pubic mound. I felt my cock twitch and used my finger to lower her shorts a little and gave her a rasberry on her mound right at the top of her pussy slit. She said that tingled and felt funny then licked me from my belly button to the base of my cock, which was still covered my my shorts and getting really hard. So I licked her from her belly button down into her pussy slit. Then I tried to tongue her pussy, but she pulled herself to the ground. We both pulled up our shorts and sat down to watch tv. Billy was laying in his same spot as the last time I babysat. I sat on the loveseat and wondered if I should sit on the floor. On the tv was some movie about skiing and every few minutes there was some sort of nudity. I looked down and saw that Billy had a raging hard on. His white boxers his nothing. When Ellen came back from the kitchen she straddled Billy again and offered him a drink. Then he grabbed it and asked what was in it. As she told him it was Dr Pepper and that stuff that their dad drank, she rocked back and forth dry humping him. After a few drinks he handed it back to her and kinda thrust a few times, then grabbed her hips and stopped her from rocking. She sat there for a minute, then stood up and sat on the couch next to me. Billys cock was still swollen and he had a huge cum spot on the front of his boxers. I just sat there stunned. Neither of them said anything about her grinding on him till he came. I was ready to cum myself and slid down onto the floor hoping she would do the same for me. Nothing happened. Slowly my cock got soft and as soon as I had finially given up, Billy got up and went to the kitchen and made us all drinks. He came back and stood over me, when he handed me mine he had squated over me to reach down. When he leaned forward to give his sister a drink he sat down on my crotch. Right on my cock head and started talking aboout what was in the drink and that we would all have a good buzz. I looked down and his cock head was poking out of his boxers and there was a glob of cum right on the tip. I had never really looked at a guys dick before, but now I wanted to see and touch it. I felt my cock twitch with the thought and he ground his butt into my cock which made it throbb even more. I chuggged the drink and set the glass down on the end table. As I did he moved again and it felt like someone stoking me. I closed my eyes and tried to think of something else, I did not want my cock to get hard. It did not work, as soon as I closed my eyes and he felt my cock throbb he started rocking back and forth. I wanted him to stop because I did not want him to think I was gay, but it felt so good, I just imagined it was Ellen. He really started grinding on me and he pulled my hand up and placed it on his cock. I opened my eyes, he was hard and dripping old cum and pre cum all over my stomach. I grabbed his cock and stroked him as he ground his ass into my hard cock. He moaned and I felt him squirt his cum onto my chest, neck and chin. It pulsed 6 or 7 times, I ran my finger through it and tasted it. Hot and salty, just like mine. He slowed his thrust and I pumped upward a few times and came hard myself. I had totally forgoten that Ellen was sitting there. No one said anything for about an hour. Then Billy said he was tired and was gonna go to bed. He said that he had a king size bed and I could sleep on the other side if I did not want to sleep on the living room floor. I guess he did not know I was allowed to sleep in his parents bed, but I was now hoping he would make me cum again. So I said yeah ill be there in a few minutes. Ellen asked if I would tuck her in and I said sure. I told her I would be right in but needed to pee first. After cleaning up I wandered in and she was under the covers with the blanket under her arms. I notice she had taken off her shirt, and then I noticed that her shorts were on the floor too. She was smack dab in the middle of the bed and I tucked her feet, and then had to get onto the bed to tuck her at the sides. First I did the furthest side then I lifted the blanket to smooth it and to see if she was naked. Yep, I had cum 10 minutes ago and my cock got hard instantly. As I tucked her I could feel myseft getting so horny. She asked if I could massage her leg and slid it out and lifted her knee. I grabbed her calf and as I massaged up to her knee she lowered her leg and kinda spread it. The blanket covered her pussy and part of her thigh. When I massaged a little above her knee I asked if her whole leg needed massaging. She said yes the big muscle on the inside was sore on both legs and she lifted her left knee and spread her legs. This lifted the blanket and exposed both thighs and her bald pussy. I slid my right knee toward the middle of the bed between her legs and started massaging her right thigh. I would slide my hand toward her pussy, stopping at the heat but not touching the lips and pulling both hands back toward her knee. Each time this would pull her lips apart and I could watch the wettness seperate like spit on your lips. It was really was in her room and she pulled the blanket off her and laid there spread eagle but naked. I put a hand on each knee and spread her really wide until her lips opened and I could look into her hole. Its was bright reddish pink and wett like it had cum in it. I ran my hands down to her lips and pulled them apart, when I did she slid her foot to my cock and said take off your shorts.. I slide them off in half a second and laid down so she could use her hand of hopefully her mouth. I started to rub her pussy lips and she started stroking my cock. If felt so good. I was 16 and this was the first time a girl had touched my cock without clothes on. I slide a finger into her pussy and she moaned out loud. She got so wett I thought she came, it gushed out. I managed to use two fingers and she started thrusting forward, I dont know why but I leaned down and licked her pussy, as soon as I did she clamped herlegs on my head and shuttered. She opened her legs and released me. I wanted to fuck her so I slid up between her legs and rubbed my cock on her pussy, she said no, I want to see you squirt on me. I grabbed me little cock and stroked myself till I shot onto her belly. While she smeared it around I said I better get to your brothers room and I grabbed my shorts and left. I stopped at the bathroom and cleaned up. Then headed to bed. Billy was in bed covered in a blanket. I crawled into bed and when I lifted the blanket he was also naked. So I slid my shorts off and climbed under. I don't know what time it was but a few hours later Ellen came in and said she had a nightmare and wanted to know if she could sleep in the bed with us, I was half asleep, I scooted over to Billy and lifted the covers and she slid in. we allwoke up as the sun came up and lit the room. My head was on Ellens chest and my hand was resting on her pussy. Billys morning wood was between my but cheeks and he woke me up stroking my morning wood while he tried his best to unload in my ass. I laid there for about 10 minutes, Ellen was still asleep so I rolled onto my back forcing Billy onto his and leaned over and started sucking on his cock. I dont know what made me do it, I just wanted to taste it. His cock was really thin, like the tickness of a jumbo crayon. But it was longer than mine, A good 5 ½ or 6" long. It would hit the back of my throat if I pushed down far. Mine was and still is only about 4 ½ " and the thickness of a broom stick. Billy started rubbing a finger at my ass, I tingled all over, his sister was still sleeping and I asked if he wanted to put his dick in my ass. I started to lay face down, but some how I ended up on my side with him straddling my leg pushing his dick into my butt. After a few pushes and some spit it slid in. It was so thin, it hurt a little but felt so good at the same time. Billy was pumping really hard and I had closed my eyes, he thrust in and came. I opened my eyes and Ellen was rubbing her pussy and watching us. I was so embarassed, but she reached over and started stroking me, he pulled out and we were both laying on our backs. She was rubbing my cock and said that feels good. Then she said your weenie is thicker than his I bet it hurts more. She rolled over onto me and sat on my cock, she was rocking back and forth and I could feel the slimyness and I kept trying to get her to slide a little further down so it would go in. then billy reached over and started aiming my cock at her opening and telling her what to do. She slid back and I felt him lift my cock and pop in it went in. as she slid down onto it, I could not believe it, it was so moist and hot. In 15 minutes I had been fucked in the ass and now I had pussy wrapped around my tiny cock. Three thrust and I came harder than I ever had in my life. I stopped her from moving and she moaned more!!! I pulled out and laid down, billy slid up and started fucking Ellen. He said lick her pussy. I leaned down and started to lick here pussy slit. His cock sliding in and out, it took about 40 secounds and they both moaned and we all colaspsed on the bed. Ellen said we should all take a bath in their parents jacuzzi tub. As we got up to take a bath she asked if she could sleep in the bed with us the next night YES was all I could say. The next night is a whole other story. If you liked this or are interested in trading crotch shots or just want to see my little cock, feel free to email Jitters2012@gmail.com Thanks for Reading