Chapter 1: Taking Advantage of an Opportunity

For many girls, the first year of high school can be a traumatic time. You go from being the queen bee of middle school to the lowly freshman. Still, I imagine it must be even harder on the boys as they are so much more immature than the rest of the girls in school. Except for the kinky girls, who’s going to want to ask out one of them when there are so many other options available!

For the girls like me, it’s almost just the opposite. The older boys in school, constantly being rejected by the princesses their age, see the incoming freshman as fresh meat. It’s like wolves circling the new lambs but then I guess that’s not such a bad thing really.

For me it started even before the first day of school. I’ve written plenty about how I got my first date with the brother of one of my best friends so I won’t go into all the details again. All I really need to say is I was overwhelmed to be asked by one of the most sought-after soon-to-be juniors in school. Sharon, Steve’s sister, had told me plenty about his “rep” for chasing every skirt in sight but that also came with the clause that most of them were cheerleaders and other with big boobs and great bodies. Considering at fourteen I barely filled out my training bra (I wore an A-cup out of sheer determination), I never dreamed he would take in interest in me.

I suppose some people might say that Steve was just looking for another notch in his belt and was just using his sister’s connections to get an advance shot at the incoming class. OK, so maybe that was his original intent although he has never told me that. If he had just taken advantage of me and then moved on to someone else then I would agree with such crap. Yes, he did expect me to blow him on the first date - and in the middle of a crowded movie theater at that. Did it surprise me? Actually based on what I’d heard about him I would’ve been disappointed if he hadn’t!

That was my very first blowjob. In fact, it was the first time I’d ever even held a dick with sexual intent. I have to parse my words a little in earlier I actually held my first hard dick and even stroked it until he came but being at the time it was out of curiosity, not any sexual desire. Besides, it would’ve been weird to be turned on my own father’s dick in the first place. My mom just wanted me to understand the birds and bees after seeing my dad masturbating earlier in the day for the first time so what better way than a live demonstration? It’s not like I sucked him or did anything really weird. It was also the last time anything like that ever happened between us. Like many fathers and daughters, my dad and I may be pretty close but not in THAT way.

Even if Steve HAD asked me out just to be the first guy to get a BJ from me, he must have been impressed because he asked me out again not long after. Admittedly I had a little bit of help from my mom who had given me pointers and even a little bit of “hands on” experience using her favorite dildo. Thus I went into the situation probably as ready as any girl without having actually done it for real.

I knew at the time I had to be doing it pretty well considering he came in my mouth but then as my mom had told me, boys will cum pretty much automatically no matter how good (or bad) you suck them. The REAL confirmation came the next day of school when word got back to me by the end of the second period that Steve was telling everyone what a great blowjob I’d given him. Wow, talk about walking tall and feeling proud for the rest of the day!

Since Steve was the first guy I gave a blowjob to, it was only natural he took my virginity. Again, my mom had me fully prepared and as a result my first time was much better than a lot of my friends told me about theirs. Once again, I knew Steve liked fucking me as he came in me within minutes but it was no different than a blowjob - a boy will cum so long as he’s in a pussy no matter who it belongs to. At school it was like my social status went up another notch when he bragged about doing me. The best part was I heard he actually said I was the best “first” he’d ever had! Considering the competition, it really served to elevate my ego.

Now for the past five months we’ve been screwing like rabbits. Heck, most rabbits would be jealous of us! Many of my friends were starting to have sex as well but most of them were doing it with more than one boy. They used to tease me about only having done it with one guy but I was happy with the way Steve fucked me so the thought of having sex with another guy never seriously entered my mind. Besides, I was only fourteen so it wasn’t like I didn’t have time to do it with other boys someday. On top of all that, and most importantly, I had a major crush on Steve and at night as I masturbated about him I would dream of our courtship, engagement and then the wedding - especially the wedding night!

One night Steve picked me for a party but we had to go back to his house to get his wallet which he always seemed to be forgetting. When we got to his house he told me to stay in the car but instead I followed him in with the hopes that nobody would be home so maybe we could have our own private party! With a brother and sister and a working mom the house wasn’t empty very often which is why we usually ended up at my house when we wanted to have sex. It didn’t matter if my parents were home as they never interrupted us and if anything, they encouraged him to come over and do me rather than going out and parking or finding some other unsafe place to fuck.

Hopefully this would be one of those rare times we could do it at his house but as luck would have it his just-turned fourteen year-old brother Jim was in the family room watching TV. At first I thought that was going to make a dud of the whole idea but Steve apparently had been harboring a devious idea for teasing his pain-in-the-ass brother.

It’s incredible the difference just a few years can make between brothers. Whereas Steve was this mature, strong, smart, sexy paragon of a teenage boy, Jim was just the opposite. God, he reminded me so much of the other boys in middle school, the creeps who snapped girl’s bra straps in the hallway. Jim even tried spying on me and his sister when we would masturbate in her room. He was such a little pervert!

Seeing how Jim as all wrapped up in some TV show, I started to follow Steve up to his bedroom with my pussy tingling. It would be so hot for him to fuck me while his brother was right downstairs! To my utter disappointment, Steve stopped and then he told me his plan. While I still would have rather have played with his dick, the idea of revenge against his dorky brother was too good to pass up.

Thus while Steve looked for his “lost” wallet, I was sent off on a mission to flirt with his poor brother. Steve wanted me to tease him mercilessly and to flirt with him as best as I could. Boys! It was the perfect example of how the two brothers always seemed to be trying to get one up on the other. I got the impression that essentially Steve was more interested in rubbing his brother’s face in the fact that he was getting laid every day by me - and Jim was not.

Again, this was something I wrote about before so I will just summarize the event. Let’s just say for now that before it was all over, Jim not only got to watch his brother’s girlfriend masturbate, but he also got to witness firsthand what his older brother was getting from me most every day. It was the first time anyone had seen Steve fuck me besides my parents and his sister so it was pretty hot for me as well.

Poor Jim, all he got to do was watch Steve fucking me; he never got to touch me or enjoy me for himself which must have driven him absolutely crazy! Although I tormented Jim that night to make Steve happy (I also had fun doing it so I wasn’t complaining), it also caused me to change my mind a little bit about him, much to the horror of his sister, LOL. Suddenly the thought of someday doing something more naughty with him was no longer off the table. Indeed, it became the focus of more than a few masturbation sessions. I had no doubt that Jim was doing the same thing and it made me even hornier to imagine him stroking his cock while he dreamed of fucking me!