Chapter 5

So, that's the situation I found myself in - locked in an escalating game of sexual teasing and exhibition with my hot, nubile little sister, and inescapably drawn to the curvy body of my mother. I was hard and horny almost all the time, with no regular outlet for my urges other than Rosy Palm and her five daughters. I knew that sooner or later, something was going to have to give to the mounting pressure. So, I did the only logical thing that I could think of ... I did my level best to concentrate my urges on more appropriate females.

I am an admittedly good looking guy, smart and quite charming when the situation calls for it. I had quite a few "intimate relationships" during high school, but there were only three girls that I had actually dated.

My very first was Maggie, a petite and cute brunette pixie, with a light sprinkling of freckles across her nose and cheeks. Both of us were fourteen at the time, curious and more than a little bit horny, so we simply and quite suddenly decided to make out one hot, sunny summer afternoon. And make out we did, almost constantly whenever we had some free time and a private place. Sometimes even semi-private was enough.

Looking back now, I think the risk of being caught in public made her even hotter.

Other than some over the clothing groping and dry-humping, we didn't go much farther though. There was no love involved in our relationship, just some friendly affection. The way we saw it, it was better to gain some experience and confidence, as well as scratch a pretty damn persistent itch, with a friend, than risk embarrassment with someone we really cared about and whom we could actually have a romantic relationship with. We stayed together for the rest of the summer, a little over a month, until school started up.

I stayed single for almost a year after we ended things, until a short time after "The Event" with Andie. Although I was feeling incredibly horny, I was also understandably going through a period of major emotional upheavals. Suddenly finding yourself attracted to and damn near obsessed with your younger sister is not exactly an everyday and common occurrence.

At least, I don't think it is.

There wasn't just guilt and moral qualms for me to come to terms with, but serious worry about my mental health that would eventually take months to reconcile with. Even then, for years a part of me couldn't help but wonder if I was some sort of perverted freak, destined to never really connect with a significant other.

Out of near desperation, I eventually decided to ask out one of my classmates, Vanessa Neves. We had been on friendly terms for some time, bonding over the Portuguese language. Her family had emigrated from Brazil, while my late grandparents, on my mother's side, were originally from the Azores. She was a truly gorgeous and exotic looking girl, with naturally frizzy, long blonde hair, dark blue eyes, light mocha skin and a curvy figure, especially her generous backside and thighs. Add to that, she was smart and incredibly caring, and she was damn near the whole package.

She was way out of my league, so I was understandably surprised when she accepted quite enthusiastically. Lucky for me, she thought that I was cute and funny.

Though it all started out pretty casual, we eventual began dating exclusively for over a year. Right from our first date, I could tell that Vanessa was much more sexually experienced than I, due mostly to her confidant and take-charge demeanor. I didn't bother asking any questions, thank God, I doubt if my young and still inexperienced male ego could have handled the truth. Nevertheless, I quickly learned to appreciate and take advantage of her experience over our following dates. I became a very dedicated, attentive, and eager student, and according to her, a quite the accomplished one.

All in all, we fit well together, both in and out of bed, and I honestly thought that we were in love. We'd even introduced each other to our respective families with all around positive results. Andie did seem a bit jealous, but Vanessa won her over in the end.

Believe it or not, but I'd actually began seriously considering proposing to her after graduation.

Unfortunately, after spending winter break in Brazil visiting relatives, Vanessa sadly told me that we had to break up. She had apparently met someone, an older college student, and fallen head over heels in love.

Needless to say, I was devastated. I spent the following weeks holed up in my room, completely depressed. Even my and Andie's sexual teasing game provided me with no more than a fleeting distraction. In fact, I think that she was a bit worried and annoyed that I had temporarily lost my enthusiasm for her body.

Time heals all wounds though. Vanessa and I would actually become friends again, just in time for graduation.

She did leave me with a parting gift I was very thankful for - she had liberally bragged on my sexual prowess amongst our school's female population. Whether it was out of genuine feelings of affection and concern for me, or due to guilt from dumping me so abruptly, it didn't really matter. As soon as word had gotten around of our breakup, I was very nearly swamped by women making it plainly known to me, that they too were single, looking for company, and willing to give me a try.

Now, I was well known and liked all through high school, amongst various diverse cliques and social circles, but I seriously lacked that mysterious and intangible quality which makes one truly "popular". That's why I was surprised and a bit overwhelmed by some of the very hot and very popular girls that had approached me.

As soon as I felt up to it, I made sure to take full advantage of my new single status. I'm sure that it helped me through the healing process.

I didn't actually date any girls exclusively – almost all of them made it clear from the very beginning that they just wanted to have a little x-rated fun. Some didn't even want that much, just some good-looking, charming company and maybe a hot make-out session at the end of the night. And I, of course, was all too happy to fulfill their wishes.

But then I met Megan.

She was a transfer student from out of state and completely different than any of the other girls that I had ever been with before – a redheaded, tattooed, and pierced goth princess. I don't know how, seeing as we were so different, but we hit it off pretty quickly. Beneath her layers of black clothing, was a trim, perky, and tight body, with flawlessly smooth, pale skin, generously accented with freckles. But more importantly, underneath her hard, thick exterior shell of antisocial impulses, dark emotions, and slightly morbid personality, she truly was a deep, empathetic, and passionate girl. Deep, deep down underneath, I admit, but it was there and she eventually shared it with me, along with her innermost thoughts, dreams and feelings. A rare privilege I respected.

With little preamble, we went almost straight from acquaintances, to close friends, to friends with benefits.

Some very, very nice benefits.

While Vanessa had approached sex with excited enthusiasm, fucking Megan tended to be frenzied, even forceful and regularly kinky. A little bit of bondage and spanking (both giving and receiving), role-playing sexual scenarios (from the clichéd "pool boy meets lonely housewife" to rape play), and the occasional bout of sex in public. Instead of simply a fun and intimate way to bond and spend time together, with her sex was also a competition - who could outlast the other and make them call out for mercy first.

It was different, but certainly enjoyable and one hell of an eye-opening education. The occasional bruises, bite marks, and scratches were all more than worth it.

We eventually became close enough that, thanks to how sexually open and kinky she was, I felt comfortable confessing to her how I felt about my sister and mother, describing some of our encounters. Though I didn't expect any mockery or derision, her reaction really took me off guard – she got extremely turned on and tried to fuck my brains out, calling me "big bro" as she urged me on.

From that day forward, incest roleplaying became a regular part of our sex lives. Daddy-daughter, mother-son, brother-sister, we tried it all, diving into porn and erotic stories for inspiring scenarios. Though Megan didn't have anyone in her own family tree that she was in any way attracted to, just the fantasy of the taboo, forbidden kink was enough to leave her panties almost literally soaked.