I was 11 and trying to spy on my 18-year-old sister and her boyfriend afternoons in her bedroom. All I ever got out of it besides lots of noise was the two times I saw each one when they came out of her room to use the bathroom. They were naked and I could see her bush and tits and his cock and balls. Sis could bring him to our house because our parents worked very late in the city at their law firm and it was her responsibility to take care of me until they got home around 9:30.
Sis was also the captain of the junior-varsity cheerleaders and, since she was both older than the other girls and open about the fact that she was fucking, a couple of the younger girls asked her to advise them about sex. One afternoon when one of her teammates was over I was in my bedroom ignoring them, doing homework when Sis knocked on the door.
"I know you've been interested in what Bob and I are doing," she said, "but you're too young. But I'll help you get started if you'll model for my friend."
Sis explained that I would come to her room and get naked so she could show off the various parts of my male anatomy and generally let the girl learn about boys from me.
I was curious enough to agree, so we went to her room and she introduced me to Anne. Sis had me strip and stand there while she lead Anne in examining me. I was nervous and shaking but I loved the attention. Sis calmed me down by praising my body and saying how, "someday soon," I'd be able to satisfy a woman.
Then she had me to lie on the bed and told Anne to touch my 3⅛-inch cock, kiss it, and take it in her mouth and suck. She had Anne play with my balls, sniff my asshole, and kiss me all over, including inside my thighs. I loved it.
After Anne left, Sis explained that Anne had decided to start having sex with her boyfriend but didn't really know much about a boy's anatomy. She said I was a very good male model.
She had me model for two other girls on her squad after that, but I got tired of the one-way thrill and demanded to be able to touch them. Sis said that wasn't what she had in mind "and besides, you're not ready." So the sessions ended.
That fall Sis went away to college and my parents had a dilemma. They had to work in the city but there was this now-12-year-old boy who needed supervision. Mom first tried having me stay with neighbors, but they had kids of their own and it didn't work out. Then she tried a couple of housekeepers, women who cleaned the house and did the laundry as well as made my dinner. These didn't work out either because they couldn't make me do my homework.
Finally, after almost a year, mom found a high-school junior who would meet me when I came home, see that I did my homework, cook me dinner, and stay until 9.
It was Anne.
Over that summer I had begun to mature. I had a small amount of fluffy pubic hair, my cock was now 4 inches long (4¼ inches if I cheated measuring), and I was capable of sustaining an erection. I was beating off to some porno my dad thought he'd hidden in his closet.
For the first 2 days Anne and I didn't acknowledge we knew each other. We settled into a routine where I got home first and Anne would arrive maybe 15 minutes later. We would talk, then I would go to my room for an hour and do my homework. Anne would check it and we would have dinner. Then I could watch TV or play videos until 9 when I had to go to bed.
Day three, when I got home, Anne was already there. So was a guy and I interrupted them as they were making out on the couch. They jumped up and Anne said he was a friend who had brought some school stuff over. She was blushing and the guy left real fast. I got a hard on but went to my room to do my homework and brought it back to Anne as though nothing had happened.
"I hope you won't say anything to your mom."
"No," I said, then "Do you remember me?"
"Oh yes, you had the cutest little penis and I loved having it in my mouth for the first time. Your hairless body really turned me on. Now I see you've started to grow up."
With that she reached over and kissed me on the lips. I responded and she giggled.
"I'll show you what your sister wouldn't," she said, and gave me a lesson in kissing. After two hours of this she stopped and made us a quick dinner and I went to bed.