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My favorite sitter.

When I was quite young, my Mom wouldn’t leave me at home without a sitter. She got this young college girl from the neighborhood to stay with me on weekend nights so she could go out partying with her friends. I thought I was a big boy and could stay by myself, but she wouldn’t have any of it.
Anyway the girl watching me was named Heather. She didn’t really look like an adult but Mom trusted her because she was really mature and trustworthy.
We usually got pizza delivered, watched tv, and I usually fell asl**p on the couch with her next to me, and wouldn’t remember anything until, she woke me up to hustle me off to bed shortly before my mom returned home.
One night she walked in, plopped her school books on the floor and said hi to me. After my mom left, she told me that since I was so good for her, I could stay up and watch tv as late as I wanted, as long as I didn’t tell my mom, and I went to bed before she got home without a fuss. Of course I agreed, feeling grown up, and felt like she was conspiratorially sharing a secret with me. She told me she was bored late at night because I fell asl**p so easily, and wanted me to stay up with her.
But, baby boy falls asl**p so so easily. That first night she let me stay up late, we cuddled on the couch under a blanket and maybe a half hour later I was dead asl**p. I don’t know how much later it was when I woke up but I had a really painful pee pee hardon. I slipped out from under the blanket to go pee and tried to keep her from seeing my stiff little dick. I had to go so bad I forgot to notice I was only in my underwear. Somehow my pj bottoms were missing. I was in such a fog I just finished up and snuggled right back in with her and as I drifted back off, I noticed her hands were hidden under the blanket and her eyes were closed, but I didn’t think she was sl**ping.
A few times she watched me, my mom stayed out so late, Heather would stay the night, but I never knew what time my mom came home, and I would wake up in the morning with me and Heather curled up on the couch together. I really liked cuddling with her, and she told me I was her little boyfriend. I hugged her whenever she came over and before she left, my head resting against her belly.
One night we were.really bored, and shortly after my mom left she asked if we could do something cool and secret and I had to promise to keep it a secret. Of course I always agreed to do whatever she wanted, especially when I thought she was going to let me do something grown up.
We went to the “adult drinks” cabinet, and she somehow got the lock open with a bent paper clip. She took out a bottle she thought looked good, poured some of the contents into a tumbler with some ice, and mixed in some apple juice. We passed the cup back and forth a few times. It tasted fine, and soon my stomach felt warm and I felt good all over. I felt like I was in a really good mood, and we were laughing and giggling at eachother.
We took the drink back to the couch and we laid down with the upper part of my body between her legs. We passed the drink back and forth a few times and got really relaxed. Eventually I had to pee, but when I went to get up she asked where I was going. I told her I had to pee, and she asked me if she could go with me. I asked her why and she giggled and said she wanted to make sure I washed my hands. While I stood in front of the toilet, she watched, and at first nothing would come out. She asked what was wrong, and I told her I couldn’t go with her watching. She said she thought it was cute, but that I should just relax. After all, she said I was her little boyfriend, and boyfriends and girlfriends see eachother naked all the time. She started rubbing up and down my back while I stood there and she even rubbed my butt cheeks. I guess it did relax me because my pee started to squirt out a little at a time. She then told me she would hold it for me because it looked like I was going to pee all over the rim. Of course I locked up again, and no pee would come out. She told me to relax again and eventually I could pee a little bit at a time with her holding me. Of course my little cock was rock hard, so even when I relaxed, it still dribbled out. She was holding my dick and rubbing my butt while I slowly peed, and occasionally when her hand drifted into my butt crack, I would tense up, and the flow would abruptly stop. She told me she liked how my dick felt while my pee was coming out. I asked her what it felt like when a girl peed because I knew they had something different for that. She laughed and said she’d maybe show me, but first things first. Eventually I was able to squirt out the last of my pee pee, we washed both our hands and returned to the tv, couch, and the drink. This time I sat up, and she laid back with her pretty head in my lap. She covered her lap with the blanket and her hands disappeared under and she had me feed the drink to her while her hands moved around mysteriously. She squirmed and made little panting noises. Eventually she said this is no good because now she had to pee and asked me to come watch her. I was excited and quickly followed her. She squatted on the seat but then spread her legs and let me see her thingy for the first time ever. I was fascinated as she ran her finger up and down the crack a few times and then spread the lips out while she pissed. When she saw my hard dick, she asked me if I liked looking at her. She then grabbed my hardon through my pjs, and said yeah I guess you do. I had no idea how her parts worked, but my dick must’ve liked it when I looked at her, because it was so hard I thought maybe something was wrong with it.
When she finally finished peeing and wiped we ran back to the couch and we laid back on opposite ends of the couch facing eachother. She had me pull out my tingling hardon through the hole in the front of my jams and told me to hold it in my hand and gently pull it up and down. It felt great and I found the comfortable way to do it while she watched and played with herself. She took her shirt off and let me see her beautiful boobs too. She started moaning and rubbing her nipples. I don’t know what happened to me but suddenly I lunged at her, buried my head between her breasts and had a shuddering almost dry first orgasm. I squirt a tiny amount of clear cum just above her pussy as I licked and slobbered on her breasts. She moaned and came on her fingers. I asked her what just happened because I thought I just had a heart attack. She laughed when she caught her breath and told me that was why boyfriends and girlfriends liked eachother.
I asked her if that was all they do and she said don’t worry, we’re just getting started.
After a minute she put a finger in her pussy and let me watch again. I thought it was neat to have a hole to put fingers into. I was still hard and as I started rubbing my dick again, I got an idea. I took off my pj bottom and threw it on the floor, spread my legs, and started running my finger up and down my butt crack. She saw and moaned oh yeah. I rubbed my butthole the same way that I saw her rubbing her pussy. When she finally spoke, she almost yelled at me and said yeah do it! I didn’t know what she meant until she told me to stick a finger in my butt. I tried it and it felt funky but didn’t go in far, but it did feel pretty good. She said to do like this, and licked her finger on her free hand and stuck it in her own ass. I did it, my finger already tasted poopy but I was so.worked up I didn’t care, and my finger went much further in there. Soon we were both masterbating and finger fucking ourselves while watching eachother.
It got really hot, and then she said here let me help. She immediately leaned towards me, sucked the head of my dick into her mouth, moved my hands out of the way, and sank a long skinny finger deep into my ass. Her mouth felt so good on my dick and her finger hit a spot inside my ass that felt fantastic. I had another crazy feeling orgasm right away. She jumped up, turned around, and flopped her pussy right on my face, grinding up and down on me so her butt and pussy were all over my face. Instinct took over as I tried to put my tongue up inside both holes. I didn’t know what I was doing but I knew I liked the taste. Soon she started moving really fast and her hole got really juicy on my face while she had a moaning orgasm on me.
We settled down and I put my pjs back on while I caught my breath. She said we had enough for now, we should probably clean up and fix the liquor cabinet before my mom came home.
We both fell asl**p the couch and in the morning when we woke up, we both acted like nothing had happened in front of my mom, but when it came time for her to leave, she hustled me in to the hallway on her way out.the door, and whispered in my ear that there were more things for us to try the next time she sat for me. Keep our secret and she’ll see me soon. Then she gave me a big grown up kiss on the mouth, patted me on the butt, and left.
I eagerly awaited the next time, because she was my favorite sitter.

Updated: October 21, 2016 — 1:30 pm

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