First Time With Babysitter

I am an only child and my parents never make a big deal out of letting me run around the house nude if it was between my room and the bath or running downstairs to get underwear from the wash when I was younger. I am also home schooled which is great since I rarely have to get fully dressed. I spent many a day in nothing but my white briefs when I was little. My mom was also a stay at home mom till I turned 12 and she felt I could stay home alone more although back when I was 13 she rarely left me alone for more than a few hours at a time.

My first memories of erections was when my mom made me and my friends little loin cloths out of some silky or nylon fabric so we could play Indians or little jungle boys or Tarzan. We would all strip and mom would help us put them on and paint us up and we would all get in the bath naked after to get washed up. The silky feel of the material against our little penises would get us all hard and we would find ways of feeling each other through the material but that was the extent of our sexual play except for an occasional playing doctor with some girls.

I guess we turned 11 or 12 when playing those sort of games wasn't fun any more but I still enjoyed running around the house in nothing but the silky loin cloth. When I was 12 and mom left me for a few hours at a time I took the time to strip and explore my body which started changing. I never got sex-ed like some of the neighbor boys that go to school but I would get some ideas of things that happen from them and other boys that I home school with a few times a week. At 13, a month shy of my 14th birthday, I began to get worried about my little organs. They were bigger, my penis maybe 4 1/2 inches and my balls were bigger and hung way down but I still had no hair like some friends would brag about. It would get incredibly hard during my baths and when I ran around naked in the house and other times and I noticed it would start to feel great when I would rub it with my hand or against other things but I never understood anything about orgasms.

One day my parents announced they would be going away for the weekend and I would stay home with the 16 year old girl that would babysit me. I argued a little about that since they trusted me for the last year to be home alone when they went out but they weren't going for it all weekend. They did leave me alone during the afternoon until Sue got home from school later in the afternoon. After my parents left I locked the doors and immediately stripped to enjoy my naked freedom. I left some underwear and shorts near the door to put on when Sue would arrive before letting her in. Later I was laying on the couch playing with my boner when I had the urge to take a nap.

I woke up a bit later and was shocked to find Sue sitting in the same room reading a book for her homework. Unknown to me my parents gave her a key and she let herself in after I didn't answer the door. She found me sleeping with a raging boner and decided to let me sleep. I know she has brothers much younger than me and she probably saw them naked often and even changed their diaper but I was still a bit embarrassed and immediately tried to cover up with a pillow but I knew she already saw me so I didn't make any effort to get my clothes. I was hoping she would get up and leave the room so I could get dressed without streaking across the room. I didn't say much at first except 'Hi' and 'How did you get in' and 'How was school' and other small talk. She finally asked me if I always went around the house naked and I said only when I was alone. Sue replied that she also enjoyed doing that when she was alone or with just her brothers. She then asked if I wouldn't mind if she got naked right then and we could both be nudists for the weekend. I was a bit nervous at first. I was a bit embarrassed about not being as developed as other boys and was afraid she would laugh. Her oldest brother Joey was 11 1/2 then and he just showed me about a month before a few hairs above his penis. After a little persuasion she convinced me it was alright and she wouldn't make fun of me. Secretly I wanted more than anything to her naked. Until then I saw a few girls naked but not for a couple years and they were all girls my age or a little younger. They didn't breasts like Sue and at the time I never thought of them in so much a sexual way but rather just curious about our differences. At 13 I was eager to see real tits and a hairy pussy.

Sue quickly removed all her clothes after I agreed. I saw her full hand size tits for the first time but was surprised she didn't have any pubic hair. She told me later she would shave it off to keep her younger brothers from pulling on it.

We didn't really say or do anything about being naked until after we ordered and ate pizza. She insisted on getting dressed for that, not only to answer the door for the delivery guy but she just wanted us dressed to eat. I managed to get her to let me wear one of the loin cloths during meal times.

After pizza the first night we took off our clothes again and I had a boner from the feel of the silky cloth. It was then that she commented that she was surprised I didn't have hair yet and if I shaved but I couldn't say I did. She did say I was much bigger than Joey though and that made me feel a lot better that she was impressed with something. She then asked me if I squirted yet. I admitted I didn't know what she meant and she explained to me about what might happen when I jerk off, as she put it. I was still a bit clueless. I admitted I never tried 'cumming' and she offered to teach me all about it if I would help her. I didn't know how I could help her but I agreed.

She made me lay on the same sofa I was on before and she started to rub my penis in the palm of her hand, much in the same way I always did. When it started to get harder and stood straight up she started to rub up and down with her thumb and three fingers, occasionally pulling the foreskin all the down, exposing my little purple head. This was something I never thought of trying. About once a week my mom would make sure I would pull the skin back while I was in my bath but I never touched it there. I tried a few times when I was younger but it always gave me the urge to pee so I left it alone. Sue seemed to know that this would feel good and purposely made my skin rub over the head and even used her other fingers to rub the head while stroking. The urge to pee soon came to me and I told her so but she told me to just lay there and relax. It wasn't pee but an orgasm. At one point I saw some clear liquid start to come out and make my penis and Sue's fingers slippery. I tried to get up to run to the bathroom but she pushed me back down and ordered me to hold on. I'm glad I did because in just a few minutes I felt my penis explode. My eyes were closed at the time and I thought I peed all over myself but after the feeling went away I saw there was no pee, just a very slippery liquid coating my throbbing, jerking hard penis. It was a dry cum I guess. I didn't start to squirt cum for another year about 6 months after getting my first hairs.

I may have never learned about orgasms unless Sue stayed with me that weekend. She showed me how to make her cum by putting my fingers in her pussy and rubbing her clit. I was really hooked myself on jerking off. On Saturday she helped me cum 10 times in about 2 hours. We just took turns doing each other until we were too worn out.

A few months later my parents and Sue's parents went away for a Saturday all day and Sue stayed with me again.