This is a great site. I'm reminded of my first time with an orgasm and also with a girl one September day about 30 years ago.
This happened thirty years ago when I was 12 and just starting the seventh grade. I was never much interested in sexual matters and I suppose I was a bit late in the development department. I was just beginning to notice my balls getting larger and hanging down and penis getting larger about 4 inches and getting more erections but I didn't make any significance to it since no hair yet appeared. I was more into the Peter Pan syndrome in not wanting to grow up.
On this day I was playing with my youger brother Tim after dinner in the woods behind our house. At one point Tim slipped and fell breaking his arm. My mother was soon rushing off to the hospital after dropping me down the road to a neighbor to spend the night if needed. I complained thinking I was old enough to stay by myself but my mom wouldn't hear anything like it after seeing what happened to Tim.
The sitter, Andrea, I imagine was 17-18 since she just graduated from high school and started at a local college. I thought she looked cute but never thought about her much. She often watched me and my brother as we grew up. I was never really at her house before since Andrea always came to our house but she had studying to do and she told my mom that she could watch me if I stayed there. For some reason Andrea's parents were not at home.
After my mother left I was about to go in the house when Andrea stopped me and said I was not about to go in the house full of mud. I was sent around to the back porch and was told to strip. I didn't think much of it and took off everything but the tighty whities all boys wore then. I was clean enough to get through the house and followed Andrea upstairs to the bathroom where I was told to strip and get in the shower. I hesitated because I was a little shy but also because I had never taken a shower before. I always took baths and only when needed.
Adrea started the bath water and told me to get in and asked for my underwear so she could wash it with my other clothes while I bathed. I reluctantly obeyed and got in the tub. It didn't really bother me much if she saw me naked as she often saw me and my brother in the tub as we grew up, it was only recently I started being a bit shy about it. I was laying down in the tub not long not thinking at all about washing. I was playing a game getting soap on a washcloth, then making an upside down cup with it over the water and pulling it down making soap bubbles come out the top. I started doing this over my penis when it got hard and made a point in the washcloth when the bubble ran out.
Andrea soon came in and saw I hadn't washed at all and also the water was already pretty dirty just from laying in it. She told me I should just shower and I said I didn't know how. She said she would show me and opened the drain and made me stand up. I half heartedly tried to cover my erection but not really thinking about it. She soon had the shower running and she proceeded to wash me, starting by washing my hair and the the rest, even my hard boner and sagging balls. It felt great, better than anything I ever felt before, but I didn't say anything. I rinsed off and got out and she dried me off, again giving attention to my boner. She made me walk bare down the hall to her room where she gave me a shirt to wear while my clothes got washed. I remember it was a pink button down shirt that I would have killed myself if my friends saw me in it.
It was a couple hours later. I watched tv and Andrea was studying, she actually finished and we both remembered that my clothes were still in the washer. We went down to the basement and put them in the dryer. My underwear and sox were soaking in a basin and Andrea rinsed them and hung them up. I guess she didn't want them mixed with my colored jeans and shirt.
We went back upstairs and we started to play around, wrestling and she giving me piggyback rides through the house. I think I must have been pretty small for my age for her to do this. Anyway, all this with just a thin shirt between me and her gave me a few erections which I eventually liked so much I was finding things to do just to rub myself discretely against her and get a boner but also to get the shirt to lift up and expose myself to her. She eventually caught on to what I was doing and started to grab me there. At one point I was running from her and she got the shirt tail when I bent over and let her pull it off me. I stood if front of her totally naked and teased her to catch me which she soon did (I let her)and got me on the floor. I didnt struggle much and she was leaning over me and saw my 5 inch boner sticking up at her. She aske me if I wanted her to play with it and I said yes that it feels good. She was soon rubbing it up and down. I never did it myself except a few times in the tub or after peeing so this was a new experience for me. It didn't take long and I was going over the edge, having a dry cum.
Andrea helped me out a number of times after that and even helped me with my first wet cum when I was 14 years old before she moved to a university. I don't think my mother ever understood why I wanted a babysitter at 14 years old even when she offered to let me watch my brother by myself.