This happened about a week after my 13th birthday. I heard about jacking off but never tried. I thought you had to have hair on your penis before you did stuff like that and I didn't have any yet. Although I played with it when it got hard sometimes I never did anything long enough. Then I learned somewhat by accident.
My mom made a big deal about my 13th birthday and had a big party inviting the whole neighbourhood, friends, relatives and everybody. There must have been a hundred people there. I was a bit embarrassed because she had a lot of stuff going on that was for little kids and I thought my friends would think I was still a little kid. I got through it alright. My friends and I spent most of the time in my room. My mom had one teen girl, she was 16 then, doing face painting for the little kids. Mary was from the down the street and would babysit me from time to time so I knew her. For some reason she went home and forgot her paints and we had them at our house.
About a week later my mom went out for the night and I was glad that she trusted me to be home alone for a few hours. It was a new privilege for being 13. One rule was that I couldn't have friends over so I was alone. It was early, maybe 7:00pm and hot in the house since we didn't have air conditioning so I got a shower early and hung around in just a shirt and boxers. It wasn't long after I got out of the shower when Mary showed up looking for her paints. I let her in while I looked for them. I wasn't sure if I was allowed to have her there but she wasn't really a friend and she would be there only a few minutes. I didn't know where my mom put the paints so we looked for them together. We finally found them in my mom's room. Mary was asking me stuff and found out I was alone and wouldn't have a babysitter. I think she was happy that I was old enough but also disappointed she lost a babysitting customer. At one point I complained that even though it was cool not having a babysitter I couldn't have friends over either so I was alone. Mary offered to stay with me for awhile. I never wanted to break rules with my mom and it was a grey area. Mary wasn't really babysitting me and she wasn't really a friend either. She was practically a grown up in my mind then. I thought it would be ok for her to stay a little while. In reality I found being home alone a little more scary than I thought it would be so I was relieved that I had company.
We started talking and Mary mentioned that she didn't see me much at my birthday party and missed painting my face with something. I mentioned I was too old for that stuff. Somehow she convinced me it would actually be cool to paint a large snake on my chest. I figured it would be cool and there was no chance of any friends finding out so why not? Mary had me take off my shirt and lay on the floor. It didn't really bother me that I was laying there in just my boxers. Mary saw me plenty of times in my underwear before and even naked sometimes when she babysat me.
She was painting a cobra snake, starting at the top of my chest. I was proud when she mentioned that I was starting to get good chest muscles. I was always a real skinny kid and my ribs stuck out so this was a real compliment. Mary was actually a pretty good artist and it wasn't long before I could see an actual cobra coiling around on my chest. I was beginning to be disappointed that I couldn't show anyone.
About an hour later she was down to my belly button. There wasn't just a snake but a whole jungle on my chest and belly. I was real ticklish starting at my belly button and got worse lower I was touched. I had a hard time not giggling with every stroke of Mary's paint brush. The main one she used was about an inch wide but had stiff bristles so it really tickled. I was glad that she was soon to be done since she was running out of room. I was getting nervous because if I was tickled too much I still peed and I would also get boners. If I had on pants it wouldn't have been to bad but I had on just boxers so it would be hard to hide either problem. It would not be cool to be 13 and pee my boxers or get a boner in front of a girl. I had a bit more control over the peeing than I did when I was younger but the boners just got worse. Not only did I get them more often but I saw it was a lot bigger so I couldn't hide it.
I knew Mary was trying to be careful and not tickle me and I was trying hard not to laugh but it got worse when she got close to the waist of my boxers. I thought I would get sick when I felt my penis start to twitch and move around a little on its own. I asked her if she would be done soon and she assured me she would. But she kept right on painting. Soon every brush stroke brought another twitch to my hardening penis. It seemed to get bigger faster with every stroke of her brush. I was hoping she wouldn't notice anything but in just a few minutes I could see a very noticeable tent in my boxers and it moved. I was really embarrassed and just closed my eyes and prayed for her to be done soon. It wouldn't have been too bad if the constant twitching had not caused my now totally hard boner to work its way out of the fly of my boxers. I had enough and was about to get up and run and hide in my room when Mary said something like, 'Wow, look at this. You sure are ticklish. You're a lot bigger than you used to be.'
I wasn't sure what to do. She just sort of complimented me on being more grown up and I wanted to run and hide like a baby. I wanted to at least put my boner back but she seemed to like looking at it. I was still trying to decide what to say or do when she says, 'You know, if you want, I can make this our snake's tail.' When she said it she brushed it once with a little paint. It tickled and a part of me wanted to say no but the idea seemed fun and also a little bad. I was struggling at the time with always being so good all the time and wanted to be bad sometimes. Maybe this was something I could do and my mom wouldn't know about. Mary wouldn't tell. I nervously told Mary OK.
She told me to take my boxers off but I was too nervous to do it myself so she pulled them down and took them off. My boner was sticking straight up maybe 4-1/2 inches. In a few minutes I began to relax a little. Mary noticed that my boner twitched every time she brushed my skin and we would watch it twitch fast or slow depending on how fast she painted. I didn't notice it at first but just before she got to above my penis I realized that it didn't seem to tickle as much as it just felt good. I didn't know I was just feeling horny.
I had my arms and hands at my sides the whole time. Mary was laying down on my right side. When she got to actually painting my boner she had to move down a bit and put her left arm between my legs. This also put her left boob right where my right hand was and her right one on my leg. It was the back of my hand but was the first time I felt one with my hand. All she had on her top was a tank top with no bra. Her boobs weren't really big but I did see her nipples sticking through the material. I wondered if she knew my hand was there. I wasn't sure if I should move it away or not. I really wanted to turn my hand around and give it a squeeze. At the same time Mary was starting to hold my boner with her left hand and paint it with her right. She said she had to hold it to keep it still. It didn't make sense to me since she was actually doing a lot of painting around my penis. She let go to move my balls when she painted there too. I knew she just wanted to feel them because they were tight up against between my legs. It was while she was doing that that she said, 'You can feel it if you want.' I thought she meant her boob but wasn't sure, she might have meant my boner too. I asked her what she meant. She just got up, took her top off and took my hand, turned it around and laid back down on it. I had a real boob in my hand and I could feel it! I got up the nerve to squeeze it and Mary asked if I like it. Of course I said yes.
It didn't take long before I started to squeeze her boob every time she brushed some paint on. It seemed to take forever but she got to painting my boner. It felt incredible. I wiggled my hips uncontrollably with every stroke of her brush. I didn't know what was happening but now I think Mary did. She stopped putting more paint on her brush and just went up and down. She found the right spot just below the head and would keep going back there. She teased me a few minutes like that and then just stayed at that one spot. In less than a minute I was bucking around and screaming it felt so great. She must have did it me for over a minute. I couldn't stand it anymore and had to yell for her to stop. It was a totally dry orgasm but I had my first one. I had to lay there about five minuted before I could get up. Mary told me about what happened. I got a better lesson from her than I ever got in school or from other boys. By that time my penis was soft again. It took Mary less than a minute to finish her masterpiece. We got up and went to my bathroom so I could see myself in the mirror. The cobra looked great.
My mom wasn't going to be home for awhile so I stayed bare for over an hour while I got us some snacks and we watched some TV. Mary claimed it was to hot and left her top off too. I wanted to keep feeling them but didn't. Eventually I realized my mom would be home soon so Mary told me to get in the shower and wash off the paint. I was disappointed my mom wouldn't see it but knew we would be in trouble if she did. When I got back to my room I found Mary on my bed, totally naked and using the same brush she used on me between her legs. She was cumming just as I went the room. It was the first time I saw a pussy except playing doctor with a neighbor girl when I was little. I was surprised at how much hair Mary had between her legs. She stopped when she saw me standing there. She just said she like using the brush there too. She told me to go downstairs and get our clothes so I got them. When I got back to my room she had her pants on again and I gave her her top and we both finished getting dressed but I just put on boxers and got in bed. It felt a little weird but Mary tucked me in and kissed me on my cheek and thanked me for a fun night. I must have fallen asleep before she even left the house because I don't remember hearing her going out the door.
I begged my mom to let Mary babysit me again after that. I said I was too scared to stay home alone. Mom said she thought I was too old and she wouldn't pay anyone anymore. I should have kept my mouth shut. I could have had Mary over after my mom left but mom always arranged for me to stay over at a friends house or to have a friend stay at my house. Even though Mary never was able to come again she always gave me a smile and a wink when we saw each other on the street until she went off to college.