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The Continuing Education

Posted by: Age: 16 Posted on: 9 comments
17 likes 9379 views Category: Masturbation Female-Male Tags: Brother, fingering, stroking, boobs

The next couple of years - A sequel to Some Unexpected Education (read first)


After the events of the last story, everything started to change very quickly for me. As if responding to the signals of my first orgasm, my more mature teenage body started developing. What was a slender straight frame was rapidly becoming more hourglass. By the time I turned 15 my hips and ass had filled in nicely, but the biggest change was the growth spurt up top. In just over a year I went from a 32-A to a 34-C. My boobs were nice and round, and my nipples that used to be pink and puffy had now settled down into flat darker areolas about half dollar round with thick nubs in the middle.   My blond bush thickened up to the point I needed to start trimming and sculpting.   My voice was becoming more husky as I was turning into a young woman. My demeanor also changed after that first experience. With the loss of innocence I took to dressing more provocatively and getting good at innuendo when talking to my friends.  I wasn't ready to have sex with the boys just yet, but I wanted to make sure I had a bunch of them thinking about me when I was ready. It was pretty obvious that my brother was also enjoying my changes. We usually had the chance to get together and watch porn a couple times a month and half the time he was looking me over as much as he was watching the movies.   I was fine with that because he had also been growing up during that time. By the time he was 17 he was getting close to six foot tall and his cock had grown nicely as well. He had thickened up, probably close to 7" long, and was shooting much bigger loads.            

         We never got bored watching our porn and masturbating together. As funny and awkward as the first time was it became a very comfortable and safe experience. I personally believe it was our close relationship that kept us out of big trouble. He didn't get any girls pregnant as some of his friends did, and I was able to dodge the mistake that some of my friends made before graduating high school. Like I said before, we never crossed any major lines, meaning no intercourse and no oral sex with one another, but we did shed our inhibitions about experimenting with the smaller details...

After our first experience together, we'd get a little more comfortable each time. Initially we started sitting right next to one another on the couch so we could see better while watching the movies. We also got more comfortable with looking more closely at each others bodies as they were developing. Half the time we would still have plenty of joking and laughing mixed in to keep it light. One time about six months in, we were both extremely charged up and ended up making out pretty heavily as we finished.  Afterward when we cooled down we both agreed that was a little too weird and decided that wouldn't happen again, but we still had some good shoulder punching laughs out of it, one of our many inside jokes.   We also started to develop a more discerning taste for the type of porn we liked. He loved anything where the girls looked rock n roll with big hair and big tits, a boob man he was for certain. I liked the scenes that had a touch of kink in them. The type we always agreed on were lesbian scenes. That was usually our cherry on top.

Around the time we'd been doing it about a year, he remarked about my growing titties and asked very politely if he could feel them. I thought for a second and said, sure why not. He was very gentle and examined them thoroughly eventually squeezing my nipples softly. It was really hot and felt very good. From then on some boob play was part of our regular recipe. At one point around a year and half in, there was a couple months dry stretch where we never ended up home alone together.  Of course I had found plenty of time to watch porn by myself and masturbated at least once daily, as did he, but I really missed out buddy time together. During that spell he also started dating a girl from his class on a steady basis. One cold Friday night after our little sisters and parents went to bed, I slipped out of my room and into his. He was sitting in bed reading and barely glanced up to say, what's up?   I said very abruptly, I'm really horny! He looked up and chuckled saying, well everybody is home, no porn tonight dear.   I said with my lightly bossy tone, you know we don't need porn to get off together. He looked quizzically and said, yeah guess you're right.  I sat down on his bed and asked him why he wasn't out that night. He replied that he and his girlfriend were going out the following night. I remarked that they'd been dating for a couple months and asked him if he'd fucked her yet. He said no, and that he'd like to but she's not ready, so she lets him finger her and has given him head a few times, but that was it.                                                                            

         I asked if she had nice tits. He said yes, but not quite as big as mine. Secretly I smiled. I asked him to tell me more about the blowjobs, which he did. At this point I already had a hand down my sweats and was tapping my button.   I laid down next to him and he opened his boxers and started stroking himself. It was much more casual and lazy than our normal sessions but it was nice all the same. We picked up the pace a little when he started telling me about fingering her.  He described her pussy and how her smell was very different than mine, not bad, just different. This was really getting me going and I was rubbing myself pretty good when he asked, with a crackle in his voice, if he could finger me a little. I paused for a second and then said ok, but just rub my clit, no sticking his fingers in me.   He quickly reached down my panties and after massaging my bush for a few seconds went to work on my clit.    I came very quickly and intensely. I bit my lip to keep quiet and took a few seconds to cool down.   I looked at him and asked can I watch you finish now? He paused for a second and surprised me asking me if I'd stroke his cock for him.   I sat back and thought about what we just did and said, oh boy, I think we're going too far. I said no, I couldn't, and he was very cool about it, but looked disappointed.   At the moment my mind was racing so I excused myself and went back to my own room. When I got there I sat on my bed for a few minutes sorting it out.  



A few minutes after catching my breathe I went back over to his room. I walked in and sat down on his bed and he quickly apologized and said he was sorry for crossing lines. I said wait just a minute, remember our original ground rules from day one? He said yes. I said it was clear. We agreed on no intercourse and no oral sex, and later agreed on no kissing. He said yes again. I looked him square in the eye and said do you promise we'll never cross those lines no matter what? He said yes, absolutely. I then told him that I thought it over and that I was ok with him fingering me sometimes, and admitted I'd actually enjoy giving him a hand-job from time to time, just not all the time for obvious reasons. He looked at me and just said, ok, deal, and smiled. I then asked him if he was still hard. He laughed and said, after what you just said, I am hard as a rock...

I pulled back his covers and saw his large penis still out the front of his boxers and very hard. He went to say something and I said sshhh.   He likes me being sliIhtly bossy!!   I grabbed his thick shaft and began to pump up and down.   I loved it. I had given a few guys in my class hand-jobs in the park, but they hadn't reached this size yet. I admired it and moaned my approval as I stroked it up and down stopping to squeeze the head periodically. I was really getting into it and as he laid his head back into his pillow I got up over him and pulled up my shirt. He reached up and started massaging my tits now hanging over his face. I was feeling so hot and naughty I lowered my tits right onto his face and told him to suck them as I was really pumping his cock. I honestly couldn't believe how big it was. Looking at it was one thing, but holding it was another, and it was so hot.    When he couldn't take anymore, he whispered that he was going to cum. With that I slid down his chest and got up really close. As I felt his cock start to spasm I aimed it towards my chest as he unleashed a very warm and heavy load all over my boobs.                                                                                                                                                          

After enjoying the sight for minute I hopped up next to the bed and pulled my shirt off and used it to clean up my chest. I looked at him and all he could manage to mumble was thanks. I quick popped across the hall topless and stuffed the shirt deep in my hamper making a mental note to bring a small towel from now on. That incident seemed to reignite our porn watching sessions and we did start fingering and stroking each other now and then, just as a special treat, usually for holidays, birthdays, or friendly bets.

Although we never did cross the major lines we agreed on, this wasn't the last time we'd find new ways to kink it up...a couple months later, we had company...stay tuned.



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