Prologue

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Mult, Consensual, Lesbian, Cheating, Incest, Brother, Sister, Light Bond, Group Sex, Orgy, First, Oral Sex, Anal Sex, Sex Toys, Pregnancy, Cream Pie, School, .

Desc: Coming of Age Sex Story: Prologue - 10 years in my life, from first love and first pain to finding happiness and someone to settle down with. Along the way, I have girlfriends and lose girlfriends. I face the highs of hot orgies and the lows of deep loss. I'm far from ordinary, but this is MY life.



She was gorgeous. Her black hair was straight and smooth and hung like a silk curtain over her shoulders. Her face was a work of art, with high cheekbones and luminous eyes. Her light skin was soft and unblemished. Even her name was uniquely gorgeous... "Cherys" (pronounced Sheh-REESE, her parents were hippies or something).

She was nineteen, in the full flower of youth with her best years still ahead of her. And despite her young age, I couldn't help but think of her already as a woman. She had full curves perched around the tightness only a teenager possesses. Hers was a body that would be the envy of any model in the nude magazines my best friend swiped from his dad. I imagine that her body was the perfection that Adam first witnessed when God created Eve.

Her tits were so big, so round, and so indescribably magnetic. Her ass was buoyant and tight as a drum. Her irises flickered and changed color depending on the light, from green to blue to violet, each hue more beautiful than the last. Even her hands were delicate and utterly lovely. I was so in love.

Too bad she was taken... by my sister.

Yes, I did say 'sister'.

Oh, what cruel fate that such a creature of perfection should be forever beyond my reach, in more ways than one? Cherys was held before me as the embodiment of absolute temptation, and yet I had no hope. To be dating a family member automatically made her off-limits according to The Code. The fact that she was a lesbian dashed any ideas of attempting to steal her, even if I wanted to break The Code.

If that wasn't bad enough, Cherys practically lived at our house. Her parents, while tendering reluctant acceptance of her sexual orientation, didn't want to see it personally in their home. So my sister and Cherys spent all their "together" time at our place. Thus, I frequently saw Cherys in various states of undress up and down the halls. And to make matters worse (for my hormones) I was forced to listen to her having sex with my sister through the thin wall between our bedrooms.

I was an eighteen-year-old boy, and suffice to say that Cherys was the star of many of my fantasies.

Just don't tell my girlfriend that.

Oh yeah, did I mention I had a girlfriend?

Ours was the storybook High School romance. We'd met the first week of our freshman year, getting funneled in from different Middle Schools. I went out for the football team. Monica auditioned to be a cheerleader. Various team hazing rituals brought us together more than once and after several group dates I asked her to go steady with me. She'd been pursued by a Varsity upperclassman but chose me instead. Now, a few years later, I'm the Varsity jock and Monica is the head cheerleader.

No, I'm a wide receiver, not the quarterback. We're not THAT cliché.

But anyways, as far as the student body was concerned, Monica and I were the model couple. We'd been together for years, we looked good together, and we were both in rather popular social circles. We had the perfect relationship, at least as far as the student body knew.

As far as I knew? Well, I was DYING to get laid.

You see, Monica had this mixed-up idea of saving herself for marriage. She was upfront about it from the beginning and I'd agreed not to push her. When you're a freshman trying to win a cute redhead from an upperclassman jerk, you'll agree to anything. Years later, that agreement was the invisible crack in our relationship just waiting for a chance to become the next great earthquake.

I mean, come on! Monica was built for sex. She was a curvaceous, gorgeous redhead with tits too big for her slender frame. Only 5'4", her compact body exuded power and energy best directed into the wildest, sexual, rabbit-fucking frenzy imaginable. Coupled with her social butterfly personality, she was the perfect cheerleader.

And she was mine.

But she wouldn't have sex with me.

To be fair, we did just about everything else: handjobs, oral sex, titfucks. Monica was as hot and horny as I was. After every single ballgame, she would get so revved up from hundreds of men ogling her in her tight cheerleader uniform that she would practically assault me to get into a sixty-nine in the backseat of my car.

Quite often she would simply open up my fly and devour my dick while I was driving her home from a date. There was something so unimaginably sexy about her plump, red lips wrapped around my shaft as her head went up and down, racing to get me to blow into the back of her throat before I got her home.

For the most part, it was enough. I mean, it's hard to complain when I've got Monica's firm, young, titflesh wrapped around my deflating pecker while streaks of hot jism slowly cool on her pretty face.

But vaginal penetration was off-limits. Hell, I'd take anal instead if she would offer it. In retrospect, maybe it wasn't fair. After all, I really think I loved her in every other way, at least as well as a teenaged boy is capable of love. But a teenaged boy is a teenaged boy, and the constant knowledge of the one thing I couldn't have was a black cancer eating away at my love for her.

Still, I couldn't cheat on her. For all the hormones coursing through my veins, I knew cheating would be wrong and I wouldn't do it. I was able to remain steadfast in this idea, despite the offers from other beautiful classmates. I stood 6'1", was considered handsome, and I was a popular starter on the football team. More than one pretty girl promised she could keep an affair secret from my girlfriend, and more than once I was sorely tempted.

But I didn't. I gave myself a mental out: the only woman I could EVER cheat on Monica with was Cherys. She was the only woman worth it. And since Cherys would never sleep with me (or any male) in a million years, I was off the hook. Besides, she and my sister had graduated and gone off to college. Out of sight, away from temptation. It was my perfect mental solution, satisfying my lustful, animal desires as well as my sense of loyalty.

Only one person knew the emotional struggles I was going through, my best friend Nate. He sat on the floor next to me in kindergarten and his football locker was next to mine today. He was the quarterback of our league-leading team and I was his top receiver. There were no secrets between us.

Zero secrets. Not even that he had a bit of a crush on my girlfriend. That revelation came a few months back. We'd had a few beers and were tossing the cans into the river just to kill time on a lazy evening. I was in my usual bitch mode about still being the only popular jock virgin in the history of popular jocks and he was dutifully sympathetic and feeling sorry for me. He had to be, given that he'd bagged three of the prettiest girls in school by now.

"I really, really like her, man..." I mourned forlornly and then chugged the remainder of my beer and chucked the empty can in a high arc off the bridge. "But sometimes I think she's a cocktease who isn't really worth it. I mean, she's just a girl, right? There are plenty of fish in the sea, right?"

Nate's expression was unreadable for a few moments. Then he sipped at his beer can, a quietly deliberate movement for him. His eyes were downcast as he said softly, "No. Monica is more than that."

I was startled by the weight in his voice. I froze, halfway to popping the top of another can.

When he looked up, he was staring off into space, a layer of liquid in his eyes making them shimmer in the moonlight. "You don't know how good you've got it, man. Monica is perfect. You don't fuck this up."

"Wait... What?"

He turned to me, his lips pressed tightly together and he actually snarled, "You make her happy or I will." With that, he finished his beer and tossed it backhand over the railing. He was already circling around to the driver's seat of his car.

I skipped opening the last can and instead just climbed into the passenger seat. Neither of us spoke about it again. He dropped me off at home and the next day my relationship with my girlfriend radically changed... for the better.

The 'no pressure' approach seemed to work wonders. I thought long and hard about how happy Monica made me and how lucky I was to have her. Whether subconsciously or not, I'd been mentally pressuring her into having sex almost every time I saw her. And once I stopped, our relationship seemed to just get so much easier. And when the tension was gone, you'd be surprised how much progress we made.

First, Monica talked about having to be sure she was with "the one". And so her vow to remain a virgin until marriage became a vow until she got engaged. I was almost ready to propose on the spot.

Three weeks later, after a particularly intense climax (her fifth, while I remained eating her out until my lips had been rubbed raw), Monica declared we would have sex on Prom night.

I couldn't wait.

No, really... I couldn't wait.

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