Where it happened: home
Ok, let me tell you about myself. I am a sophomore in high school, soon to be 16. I live with my mom who works full time and my brother Tim who just started 8th grade. Last spring my mother changed jobs. It was like a promotion except she had to go off to a business trip, staying overnight. She had never left us alone before. And even though we (Tim and I) hadn’t had a baby sitter for about three years, my mom said she was going to get one this time, since she didn’t want to leave us overnight. I argued that I was too old for a babysitter and that Tim and I could take care of ourselves, at least for one night. But mom would not be persuaded. Her only problem was that she didn’t have a current list of sitters. She began by calling Anna, a girl who was a high school senior when she last sat for us three or four years ago. I remembered that she was fairly nice looking — well, what I really remembered is the she had great tits, but I was too young at the time to know what to do about it. Anyway, Mom (and as it turned out, Tim and I) got lucky. Anna was still in town and was willing to sit with us while Mom was out of town. I began to think that maybe it would be quite so bad, though I was still embarrassed at the idea of having a babysitter.
It was Friday when Mom was to leave. Anna was working for a dentist in town (maybe that’s why she was so good at “things oral” but I get ahead of myself). Tim and I were to come home after school and Anna would come over after work (about 5pm). Mom left money to order pizza for dinner and Anna would stay the night. Mom was to return home last Saturday afternoon. Tim got home from school about 4pm, but I was on the freshman baseball team and we had a game at 4pm, so I wouldn’t get home until after six. After the game I was in a hurry, so I skipped the shower and came right home.
Anna had already order the pizza when I arrived. Tim was eating a big slice while watching TV, but when I saw Anna for the first time in almost 3 years I nearly fell over. She was beautiful — and not just because she had such a great shape (she still had great tits!). She looked at me as I came in all grundy from the game, smiled, and suggested to wash up before I ate. I agreed and said I would hop in the shower and be back in a few minutes. I went upstairs, took off my clothese and walked into the bathroom to take my shower. As I turned the warm water on, I began to think about how great Anna looked and my dick immediately stood at attention. I had been jacking off for at least a couple of years, almost every day. It was not all that easy, really, since Tim and I shared a room together (bunk beds — he had the upper and I slept down below). In fact, one time he caught me wackin’ my whomper and wanted me to explain what in the hell I was doing. I told him that very soon he would experience certain feelings that would make his dick grow hard, and the only way to relieve himself was to jack off. I then demonstrated to him and shot my was in front of him. He was amazed and I seemed to notice a tiny errection in his jeans, but neither of us acted on it. Later that night, when he though I was asleep, I heard him unsnap his pj bottoms and detected the sound of a dick being smacked up and down. I didn’t know if he could cum yet, but I did know that I had introduced my 12 year old brother to the gentle pleasure of jacking off. Anyway, as I thought about Anna’s gorgeous body and the warm water was bouncing off mine, I began whacking and whacking and . . . explosion time. Ah, relief, I thought to myself.
I stepped out of the shower and grabbed a towel just as a I heard a knock on the door. Before I even thought I said, “come in.” I was used to Tim bursting in when I was in the shower to take a piss, though he usually knocked. The door opened just as I was about to dry my back and in stepped . . . well, it sure as hell wasn’t Tim! It was Anna. She got a good look at all I had to offer before I pulled to towel over my front and said, “my, but you have changed in three years . . . and all for the better. I came up to ask if you wanted mushroom or sausage pizza.” I said it didn’t matter and then I surprised myself in a couple of ways. First of all, I had just jacked off and shot my wad. But amazingly, my dick was starting to grow again. Next surprise was what I said. “Would you dry my back for me?” and handed her the towel. “Of course” she said.
I turned my back to her as she began to apply the soft towel to it. My dick kept growing. Now it isn’t a monster size. It probably is close to 5 inches when hard, and it was definitely getting hard. Then she turned me around and began to dry my chest. Then my waist. Then she got to my dick and balls. “Not bad” she said. But let me see what I can do for this condidtion. She dropped the towel and kneeled down on it so her mouth was directly in front of my dick. All of a sudden she wraps her tongue and lips around it, and I was getting my first blowjob. Man, did it feel good. Now remember, I had just jacked off before she came in. If I hadn’t, I would probably have shot my load the second she put her tongue on my dick. But I began to really enjoy what she was doing, and it seemed she was enjoying it too! She sucked in my dick to capacity and began to softly massage my balls. Talk about stimulation! So in spite of have shot my load only a few minutes earlier, it didn’t take long until I felt another load coming up the ramp. “I’m coming” I screamed. She pulled back and I let loose a modest jet of cum on her face. Then I glanced at the open door. There was Tim, standing there watching with his mouth practically on the floor and a tent pole sticking out from his shorts. Anna saw him too, and laughed. “I suppose you want the same as your brother?” she said. “Come here” she said as she motioned for me to step back. I sat down on the side of the tub while Time walked over to her and dropped his pants. He had grown some pubic hair since last I had seen him, and his “little” dick was not so little anymore. In fact, it was almost as big as mine! Anna adminstered her talented tongue to his dick and in no time Tim said, “I’m coming!” (Well, that answered another question I had about Tim) This Anna did not pull back, but drank in every drop. And here’s a really strange thing! After coming twice in less than 30 minutes, watching Anna give my kid brother a blow job brought my dick back to life! I started to get hard for yet a third time in the same evening!
Then Anna stood up (she was still fully clothed) and said, “Would you boys like a few lessons in sex?” Of course we did. She led us into Mom’s bedroom where she was going to sleep, slowly took off her clothes (I was already naked and Tim quickly took off his only remaining piece of clothing, his shirt) and we both gazed at the first time at the gorgeous body of a naked woman. What she proceeded to teach us that night was astounding. We learned more about touching, sucking, fucking and just plain old sex in one night than most guys learn in a lifetime, or so it seemed to us. The next morning Tim and I were wrapped around Anna in mom’s bed, and we had one more romp before she suggested we clean up and dress. We never did eat the pizza. But we did eat that night certainly satisfied us.
When mom came home later that day she asked how we all got along. “Great!” I said as a winked to Tim. “Well I have decided that maybe you guys are old enough to take care of yourselves when I have to leave overnight. So I won’t call Anna anymore,” said mom. I nearly pub up a fuss, but thought better of it. When Mom did leave a couple of months later, I just called Anna and invited her over for some more “lessons.” She doesn’t always stay the night, but she always “cums” over when mom leaves, if you know what I mean. Her lessons have really brought Tim and me closer. Her last lesson was on giving blow jobs. So now when Tim or I get to feeling horney, instead of sneaking a whack off hoping the other is asleep, Tim just crawls into bed with me and we suck each other’s dicks the way Anna taught us. I must say, Tim shoots quite a load for a 13 year old. And Anna’s lessons have helped us with the girls. Tim, if he isn’t exagerating too much, is quite the cocksman around his jr. high. And although he hasn’t yet scored with any of his jr. high sweeties, he nearly always gets to third base, at least according to him. I am also doing better with the ladies, though I haven’t yet fucked anybody except Anna. I did have me dick at the entrance of my last dates twat, just about to get it in, when she got frightened and asked me to stop. I did, of course, for Anna has taught me never to force and girl to fuck. This girl was so tight and I think I was hurting her. Anyway, I ended up eating her cunt while she jacked me off. Next lesson with Anna I plan to ask her how to fuck a virgin without hurting her. I’m sure she can give me some excellent pointers (if you know what I mean). I have also learned that as I learn more about sex, the more I want to learn. Sex is so wonderful and I am so thankful Mom asked Anna to “babysit” her boys just one last time!