I was 12 when this happened. My parents went out one night and left me alone for about an hour until my sitter arrived. She was a girl named Jill and was maybe 16. She was my sitter for several years. Even though I couldn't stand girls my age I had a crush on Jill and loved it when she came to watch me. She would often let me sit in her lap, cuddle me and give me kisses, mostly on my cheek but sometimes a quick one right on my mouth.
This night my mom told me to get a bath and get ready for bed before Jill arrived because it was already sort of late. After my parents left I went to my room, got undressed and was looking at myself in the mirror I had on my door. I had started growing pubic hair a few months before and was starting to show a nice bush and was showing it off with my wiener (that's what I called it then)and hanging balls. It wasn't really all that big, maybe 5 inches when hard, but it was big to me then. I was very curious about how the head would start to peek out from the foreskin as if to say, 'Hello... I've been hiding a long time but now I want to see the world.' I lost track of time and realized Jill would soon arrive and got in the shower, dried off and ran naked to my room. I couldn't find any clean underwear so I went downstairs to the laundry room where I remembered my mom telling me to get my clean clothes earlier. I got an armful of my clothes and instead of putting some underwear on right away I was taking it back to my room still naked. I figured no one was home and I enjoyed being naked when I was home alone. I was going through the hall downstairs when I saw Jill starting to call me. She just came in and surprised me and I remembered I was totally bare. Six months before I probably would not have cared much but I got a little shy about it so when I saw Jill I just dropped the clothes on the floor and froze in front of her and didn't know what to do. She started to talk to me like I still had clothes on, asking me how I was doing and stuff. She apologized for scaring me and came over and started to pick up my clothes off the floor. I saw her take a quick look at my privates and I unfroze myself and got down to help her, not so much to help but to try to hide my parts and still look cool about it. I started to think how bad it would be if the girl I had a crush on saw me with a boner. If I didn't start thinking that I might have been alright but once you start thinking about it, it happens. I could feel it growing as we picked my clothes up.
I tried to hurry and just scoop them up and get to my room but Jill insisted on refolding them right there. I kept telling her I would get them and she could go to the kitchen and get a Pepsi or something but she thought it was her fault and insisted on helping me. My wiener was getting harder all the time and I was trying to think of the best course of action. Should I keep helping, try to look cool and somehow hide it or just excuse myself and run upstairs before it gets worse? Before I could decide, it was too late. I was totally hard and the clothes were folded in two piles, one for me and one for Jill. I wanted to carry the whole thing but she thought I dropped it the first time because it was too much and she had to help. I did convince her to go first. I didn't want her looking at my behind either. I was pretty stupid when I think that I never considered just pulling on a pair of briefs right there, but I think it was because my underwear was at the top of the pile, it fell the farthest from me and Jill was folding and had that to herself. I couldn't reach it and I was too embarrassed to ask for a pair.
When we got to my room Jill put the clothes she had on my bed and started to take the clothes I had and made me stand by the drawers while she put them away. She kept asking me where different stuff went and I just told her. When I ran out of clothes I stepped over by my bed, took my hands and covered myself and watched as she put the rest of my clothes away. Her pile was all my underwear and socks and she found that drawer and put them in.
She left out a pair of briefs and held them out for me. I stood there and looked at her a few seconds trying to decide if I should walk over and get them or get her to toss them to me and try to catch with one hand and keep myself covered a little. I must have been pretty red because she told me I didn't have to be embarrassed because she saw her brothers naked all the time. I didn't see how that made a difference. I bet they never got boners like I did. She held my underwear out and told me to come get them. I still stood there. She told me to not be so scared and she wouldn't bite. I never liked being called scared and she got me. I went over right in front of her and took my hands away and said, 'See, I'm not scared!'
She looked down and said, 'Well, you don't have anything to be scared about. You're bigger than my brother and he's almost 14.'
I said, 'Really?'
She told me he didn't even have hair yet. That made me feel pretty good. She told me I was starting to get nice chest muscles and I was turning into a stud. I had no idea what that was then but I didn't want to look foolish so I just said thanks. I started to think she might have a crush on me too but I didn't dare ask her or anything.
While I was thinking about that she asks me, 'Are you going to take care of that boner before you get dressed? I'll leave you alone but I I'll stay if you want.'
I was so embarrassed. I couldn't believe she said 'boner' right in front of me and was actually talking like that to me about my privates. I wondered if it was something to do with jacking off that I heard from some other kids at school. I thought I didn't want that because every time I played with my wiener it just got hard and I wanted it to go away, not stay like that. I didn't have any experience with an orgasm or anything.
I was thinking that through and was almost ready to tell her I would just get dressed when she says to me, 'I'll take my top off if you let me stay.'
Now I was in trouble. I would have given a million bucks to see an older girls boobs and two million to see Jill's. They weren't real big but a lot bigger than any girl I knew in seventh grade and I felt Jill's through her clothes many times. Not with my hands, but when I sat in her lap and she wrestled with me and stuff they would get against various parts of my body. I wanted to see those bare for over a year and here was my chance but I had no idea what she wanted me to do in return. I know what she said but I didn't understand it. How could I get her to do this and still act cool?
I'm thinking again and she tells me, 'I bet I can make you cum.'
I felt like such a idiot. Where does she want me to come? She is asking me and telling me all this stuff. I can tell where it's going. I could have some kind of sex stuff and see a real girl's boobs and I'm standing there without a clue and can't say a thing. Part of me wanted to just get dressed and another part said just go for it and figure it out as you go. I looked at her and I could see in her face that she was just about to leave. She turned her head just a little and I got scared that I wouldn't have another chance like this and blurted out, 'OK, you can stay!'
She asked, 'Do you want me to help?'
I started to think straight now that the pressure was off. Right away I figured if I didn't know what she was talking about and she did that I should let her do whatever it was she was talking about. I said, 'Alright.'
She told me to go lay on my bed and I did. She followed, sat beside me and pulled her T shirt off. She turned around and asked me to unhook her bra. I never did that before but it wasn't hard to figure out. She face me again and slipped her bra off and I saw boobs for the first time in my life. I thought they were beautiful. I was thinking they were so big I could use two hands on one and not cover it. I thought they would sag down but they were stiff and the small brown nipples were pointy. I suddenly wondered if they were soft or hard like my boner was. I was suddenly aware that I was playing with my boner with one hand and my balls with the other.
Jill asked me if I like what I saw. I just nodded my head yes. I felt like a fool again for not being able to talk. I changed my mind and said, 'They're the most beautiful things I ever saw.'
I wondered right away if I over did it. I relaxed when she said, 'Thank you, you're cute for saying so. Now let me see your things.'
I saw Jill push my hands away and she started to play with my boner and then my balls. It felt great. No one ever touched me there before and I thought I wouldn't like it if someone did, but this was better than anything I did to myself. She started to rub up and down slowly with her fingers and pulled my foreskin down, exposing the little head. She was pinching it lightly and twirling it between her fingers. I never did that. The only time I pulled the skin back was to wash it. I felt my hips push up almost uncontrollably and I was getting short of breath. At first I was just watching what she was doing to me but after several minutes I went back to looking at her boobs. I was sure they were getting bigger and pointier. I could see them rise and fall with her breathing and I started to breath they same way she did. I took some quick glances down at my boner to check once in a while but after about 5 minutes I was looking mostly between Jill's face and her boobs. She started out slowly, going between my balls, my boner and the head, but gradually got faster and faster until after maybe 10 minutes she was just going between the shaft and the head. I looked down and was surprised to see it was so big the foreskin wouldn't even go over the head at all. I couldn't believe how good it felt. I spread my legs apart and grabbed the blanket with my fists. I did it without thinking. Jill almost had to pry my fingers apart when I didn't realize what she was doing when she took my hand and put it on her right boob. Did that feel great? Both soft and yet hard. I pinched her nipple when she pinched my little purple head. She started to rub up and down faster and faster. I couldn't understand how it could keep feeling better and better. She started saying, 'Cum for me Jakey, Cum for me.' over and over and stuff like that. I still didn't understand what she meant by that. I started to feel like I had to pee in the worst way but I didn't want her to stop. I tried putting it off but finally the urge was too strong and I yelled, 'Jill, please stop and I have to pee!'
She just kept going and said, 'No, you're cumming for me Jakey.' I still didn't understand and was about to force my way up and to the bathroom when I found I couldn't get up anymore. My body; hips, legs, arms, head, everything was shaking and twisting and exploding. It lasted about thirty seconds. I was screaming and I finally couldn't take it anymore and yelled for her to stop and it was over.
I laid there with my eyes close for a minute and rested. I was dizzy. I came back to earth and Jill was asking me if I was OK. I looked up and she looked concerned until I smiled at her and told her that it was great. She held up her fingers to my face and said, 'Look.'
I saw a small amount of white goo on her fingers. I asked, 'What's that?'
She laughed a little and said, 'It's cum and you made it. Two squirts. That's good for you. My brother can't do that.' I looked down at my soft but wet wiener. I felt the slimy stuff and was proud of what I did.
She asked me not to tell anyone. Of course I promised. My parents would kill me. I asked her if we could do it again. She said, 'Sure, but once a night is enough. Go take a shower.' I was about to argue that I just had one but didn't want to get in fight with her after that so I got up and took another shower.
I took my time. I was a little tired after my first cum and I was delaying because I wasn't sure how to act afterwards. I eventually got out and started to dry off when I heard Jill kind of moaning and stuff from my room. I just listened from the door wondering what she was doing. I figured she was on the phone. I was almost done drying off when I heard her screaming, 'Oh Jakey, Oh Jakey,' over and over. I thought she was in trouble so I ran to my room and saw her on my bed naked with her hand between her legs. She stopped right about when I got to the door and she she relaxed.
I figured out that girls could feel the same thing but couldn't figure how without the right parts. I just stood at the door looking at her. She looked up and saw me there and I guess I looked a little confused because she said, 'Yes, girls can do it too. Get ready for bed and go downstairs.'
I was a little afraid she was mad at me and also suddenly embarrassed again. I was naked again in front of her. I didn't understand why I was still embarrassed about it but I was. I quickly found my underwear and put it on. I felt better when Jill gave a small kiss on my cheek and said, 'Thank you.' I didn't know why she thank me but I returned a 'Your welcome.' and smiled up at her. I watched as she picked up her clothes and headed for the bathroom and said she was taking a shower.
I got a shirt on that I wore to bed and went downstairs and got some milk and cookies for a snack ready. Jill came down soon and we watched some movie and ate the milk and cookies while I cuddled in her lap. I didn't realize how childish that might be until after she tucked me in bed and turned out the light. I couldn't figure out if I was a kid anymore or not.
Jill watched me about four or five times after that and I didn't take any baths or showers before she came. We always ended up doing the same thing. Masturbating and then cuddling like I was a little kid and tucking me in. I think it was her way of saying she wanted me to grow up and have fun but I was too young to be her girlfriend. I was pretty disappointed when my parents thought I was too old for a sitter when I turned 13.
It didn't take long for me to figure out how to jack off myself and even do it with a male friend of mine till we were 14 and got girlfriends but I will always remember Jill as my teacher and still giving me the best masturbation orgasms I ever had.