From years ago before computers
As a kid in Wyoming I worked summers for a the high school as a custodian. Most of the time we got all the really dirty jobs the full-time workers saved for the summer kids to do. Most days I came home dead tired and really dirty and mom would often have me undress in the back yard (it was surrounded by a hedge) and then come in and shower.
It was kind of nice being naked and then showering. I didn't realize that my sister and her friend Nicki looked forward to my afternoon cleaning and watched me from my sister's window. They were a couple of years younger than me and Nicki was pretty and well developed and I had my eye on her too but I had never dated and was pretty uninformed when it came to girls. I was not aware they were watching me yet I should have known because of all the giggling in the house after my shower and my sister and Nicki always seemed to be there in the afternoons.
As the summer became warm toward July I decided I wanted to sleep out in the back yard and I'd just wear my PJ bottoms. I wasn't a hunk or anything, just tired from cleaning the school and by Friday was sore and tired. After a couple of Fridays sleeping out I needed to get up and go pee in the middle of the night. When I got up, I thought I heard someone in the back yard. I didn't have a flashlight and looked around but didn't see anyone, so I just thought it was the dog. Returning after my need was met, I just laid there and was enjoying the stars and I began to think about Nicki, and got turned on. Now having a hardon and in the back yard and thinking I was alone, I had a wonderful orgasm and just let go on the lawn. I didn't masturbate often and don't really know why except maybe I was a late sexual bloomer.
Next week, same routine. Being clueless, the giggles were a little more intense and Nicki asked if I was going to sleep out again. Never registered how she knew. But, on Friday, I was again tired from my teen week working and fell asleep right as it got dark. Usually I'm a heavy sleeper but on this night something woke me up. I was kind of in a post-sleep haze but I realized someone was feeling around my PJ bottoms. Without moving much, I shifted so I could see, and it was my sister's friend with her hands doing the exploring. I pretended to be asleep but soon had a nice hardon for her to play with. She wasn't too sure what she was doing but as she explored, I came and she let out a startled noise. She had not been jacking me, just exploring and I noticed that was quite exciting. That's when I slowly began to sit, rub my eyes and pretended now to have been awakened. I looked around and could tell that Nicki was hiding behind a lilac bush, but I again pretended to see nothing. I cleaned myself up with my PJ bottoms and went back to my sleeping bag, now naked. I could tell that after a little while she left the back yard and out the back gate. Her house was about a block away.
The next week, I began to take note of all the attention I got every afternoon during my afternoon stripping in the back yard before a shower that resulted now in an erection most days. Now I began to see the curtain move as I undressed and came into the house for a shower. It was exciting. My mom was often gone doing errands and had threatened me to not leave a dirty mess in the house, so I guess she never knew that I was now sporting a boner. I thought it was pretty neat, showing off for the girls but only walking from the back yard into the house and shower. Realize that I was pretty dorky when it came to sex, and I thought I was just being a brotherly tease. I presume if mom had seen, I'd have been in big trouble.
On Friday I again slept in the back yard except this time I took off my PJs and was completely nude. I was sleeping where I could not be seen from the house in case my parents looked out but I was nervously pretending to sleep and it was warm enough to be on top of my sleeping bag. I waited. Sure enough about 11 pm I heard the back gate being carefully opened and Nicki came into the yard. It was kind of funny for me to now watch her literally cat-crawl to where I was, she thought, sleeping.
The moon was out and I remember her just looking at me as I was already excited and had a pretty nice erection. She began to touch me carefully and this time she unbuttoned her blouse and began to play with her nipples. Now this was new for me! What a treat and I erupted almost immediately and it was her turn to be a little startled. But she just sat and was very quiet and began again to touch me and also play with her boobs and play with my cum, even tasting it at one point. I was soon erect again but she really had no idea what she was doing. So very slowly I reached out and took her hand-wow was she startled but fortunately quiet-and guided her on how to make a guy cum. What surprised me was she then guided my hand to her boobs and I played with her nipples. What a rush. We kept this up for a while until I finally was drained and somewhat sore. She kissed me, for the first time ever, and quietly left.
A week later, the scene repeated but she made sure I was awake and we made out for a while and she whispered a lot of questions (she had never dated or even seen a guy naked). She would never get naked, but would unbutton her blouse and let her boobs excite me and I discovered what a turn on it was to nibble on nipples and suck on her breasts. She would also suck on my nipples and I discovered this too was a nice turn on. I would usally let her jack me off two or three times over the course of an hour and then she'd quietly leave. She did tell me she had talked to her mom about sex and was determined that we were not going to have a baby together (we were both in school and way too young).
Toward the end of the summer she did let me explore her and I enjoy the memory of her furry bush and her smell. I think she had gone to the library and discovered about female masterbation because she showed me how to bring her to intense pleasure and she said she'd just discovered it. I doubt my sister, at this point, was in the discussion. Nicki never did get completely naked but she would love to sit on my legs and bring me to orgasm and lean over and let me play and suck on her nipples. She was pretty well developed and very slender and I loved sucking on her breasts. After she got me off a couple of times, she would lie beside me so I could reach into her underwear and bring her off. She refused to get naked with me because she, correctly said, we'd not be thinking right and she would get pregnant.
It was a great summer of learning. We also discovered the pleasure of french kissing and also how erotic a tongue in the ear could be.
One Saturday when no one was at her house she invited me over so I could get a daytime look at her boobs and pussy and she could get a look at me. We explored and giggled and brought each other to orgasm, she being careful to avoid us going all the way. We dated for years and, while never going all the way, did a great deal of exploring as we learned about our sexuality. Being stupid I moved away and she went to college and married someone else. I always regret not marrying her, but what I learned about sexual pleasure I owe to her boldness and literally taking things by the hand at an early age.