tagGroup SexThe Ultimate Playboy Pt. 01

The Ultimate Playboy Pt. 01


Most stories start off with two people meeting cute, dancing around each other for a little while before falling in love and eventually, finally sharing that love in a physical sense. This is not that kind of story.

PART 1: Modest Beginnings



For the first teenaged years of my life, I was nothing special. Just your average American male. Height, weight, race, hair color, athletic ability... none of it important. Except for one thing...

No, my penis size was fairly normal. Actually, at the time, it was pretty small. You see, that one important thing was that I hit puberty fairly late. Most guys start growing hair on their balls like in Junior High at least. But I was a couple of years behind; and a couple of years behind puts a guy like me pretty darn low on the dating totem pole. I was fine socially, hanging out with friends and chatting with everyone. The only difference was that I was six inches shorter than everyone else. I didn't get picked on that much by bullies. I was just... casually ignored by the fairer sex.

Actually, there was one other thing, something that made me very special. But I wouldn't really understand it until I was well into my college years. But that's for later.

So as the short, underdeveloped teenager, I learned to lust on my own, without being obvious and without a prayer of getting laid. I appreciated the various feminine beauties around me and looked forward to the spring when the weather dictated a rather abbreviated fashion style. But to be honest, there was no more beautiful creature on this earth than the High School's Biology teacher, Mrs. Robinson.

Five feet, eight inches of va-va-voom... Cute elfin face with a hint of foreign exoticism. Intelligent, sassy, brunette, and a set of curves only a grown woman, 10 years older than me, could have. Amazing how young a person can be and still earn advanced Science degrees.

"So here's to you, Mrs. Robinson..." I found myself humming most of the days I headed towards her class. On occasion, she caught me staring at her body, a knowing smile on her lips. I dreamed my dreams, but if even the freshman girls were out of my league, then Mrs. Robinson... well... sigh...

Fortunately, that Junior year was the year my growth spurt finally hit. I actually had to shave for the first time. My voice got deeper. And girls slowly began to notice me.

I still didn't get any dates, mostly due to my own ineptness and lack of confidence. But my life was looking up. Once I found myself engaged in an idle conversation with a beautiful classmate in the hallway. My tongue tied itself in knots the instant the conversation moved away from the classwork and towards the plans for a party this weekend. After thirty seconds of me fumbling around like a near-sighted fool in the dark, she huffed away and joined some friends walking away.

But in Biology class, I was the master. Front-row, center. I knew the answer to every question, my voice clear and strong. And I always got the perfect reward in Mrs. Robinson's smiling encouragement and approval.

We were halfway done with the second semester when the Biology midterm came up. Mrs. Robinson was holding office hours after school ended on the day before the midterm, and I made definite plans to attend.

That particular week had been particularly hectic. Biology wasn't my only midterm that week, and I'd been studying my ass off every night. Consequently, I was a little tired but at the same time a little aroused. The thought of Mrs. Robinson in that short skirt she'd been wearing this spring day was giving me a rise, and I hadn't gotten around to jerking myself off in several days.

So I popped into her office hours with 3 other students, joining the round robin of Q&A while ogling every inch of perfection I could see. Mrs. Robinson had been wearing a stylish outfit suitable for a working late twenties professional. The afternoon had been edging towards the hot side and after twenty minutes she stripped down to just a thin blouse.

My eyes were bugging out for the next hour, mesmerized by the curves I saw underneath, and the bra strap semi-visible across her back through the translucent material.

I did notice that Mrs. Robinson kept glancing at me, her eyes heavy lidded, even as I stared her down. After the first hour there were only two students left, and then fifteen minutes later it was just me. I kept asking questions, forcing my brain to focus and dredge up new material to cover, but my head was swimming in a sea of arousal and hormones being alone in a closed room with her.

I noticed we were both sweating; Mrs. Robinson's skin flushed as I watched a bead of sweat trickle down her neck and then run down the deep valley of her cleavage. When the droplet disappeared out of my view, I realized that neither of us had spoken for a good couple of minutes, and I looked up to see a face I had only ever seen in my daydreams. Mrs. Robinson's eyes were a little out of focus, but firmly directed towards me. Her lips were pursed and open, a visible pant emerging every few seconds. Her skin looked to be on fire, and then before I realized it, those lips were pressed against mine, and she was kissing me ferociously.

All I could do was kiss back, every fiber of my being rejoicing in this moment, instinct and lust taking control over my body and then I had enfolded her up in my arms. I stood up, finally taller than her, my tongue parting those lips to explore into her mouth.

I must have died and gone to heaven. Or at least, fallen asleep and started dreaming. But oh what a happy dream.

We kept kissing and kissing and then her hands went to her blouse, yanking it over her head before reaching back to snap her bra. When it came loose, my jaw dropped to the floor as those perfectly round orbs came into unobstructed view, capped by erect and perky nipples. I had to taste them, and so I found my face buried between her breasts even as her delicate hands ducked to find the clasp of my jeans.

Mrs. Robinson got them open, shoving my jeans to my knees, my erection tenting my boxers and my face against her chest. That was the position the Principal found us in when he opened the door.


So, it hadn't been a dream.

I sat alone in my early 90s Toyota, bored to tears, staring at the taillights of the car in front of me. Imagine a teenaged high schooler stuck in rush hour traffic.

But this was still the fastest way of getting to my new high school across town. I'd never even had the chance to see Mrs. Robinson after that day. She'd been fired and I was expelled immediately. I missed the rest of the semester. And Mrs. Robinson had moved to another town I heard. I never understood why she kissed me, and I expected that I never would. I just filed it away in my brain as an unexplained event in my life. Maybe it would all make sense when I got older.

Fortunately my mom had talked the District Superintendent into letting me attend another High School to at least graduate. So I had to put up with a thirty-minute commute every day, wasting my summer vacation on make-up classes and then loading up with a killer course load for my Senior year.

Throughout the summer I was just the anonymous new kid. And my mom had me grounded for the entire summer so my only real human contact was with my parents. Sometimes being an only child can really suck.

Within the first week of my Senior year at my new school, however, I found myself in the middle of way more human attention than I had ever desired.

Word had apparently gotten out that I was a new guy by expulsion, as opposed to the typical new guy by relocation. This of course had everyone initially curious as to the reason I got expelled. Then this of course led to the rumor from a friend of a friend: the new guy got caught getting frisky with his Biology teacher. The story of course got multiplied with every telling. First I seduced her. Then we'd actually had sex. Then we were caught WHILE having sex. Etc, etc.

I tried to ignore most of it, deflecting away the questions as much as possible and just try to graduate, then get the hell out of the state, and move on with my life. I started to get good at the verbal dismissal after a few days of guys trying to get me to brag about my conquest. But then I found a questioner I wasn't so quick to dismiss.

She had bright green eyes, a pretty face, red-blonde hair, and was STACKED. And so with big boobs pressed against my chest and minted breath in my face, Red asked me if the stories were true. I found that confidence in my words came easily when I believed in them. So with a clear voice and sharp eyes, I told her that the stories were indeed true.

Red smiled, flashing brilliant white teeth, and then half turned away. "I'll have to see it for myself before I really believe it."

Then she turned and continued down the hallway. I stared down at such a tight ass and tiny waist as only a teenaged girl could possess, I found my hormones roaring once again, like superheated flames shooting out of my eyes and bullseying onto the round globes of her butt.

She turned around once, her eyes darting up and down as if to evaluate me again for the first time, before she turned and half fled away.

That night, for the first time in many months, my dreams were not filled with visions of Mrs. Robinson. I had a new playmate.

The next day I was getting my books out of my locker at the end of our lunch break when I felt a hand slip into the back pocket of my jeans, palm curving around my butt. I looked to the side to see a flash of red hair, but then she was already pulling me away down the halls. A minute later the bells rang signifying that I was late for class.

When the hallways were completely empty, Red pulled me deeper into the school towards a wing of smaller classrooms. We came to a door labeled 'Maintenance', and she pulled the door then tugged me inside. If I wasn't sure what was going on before, I felt pretty sure when Red shoved her tongue down my throat. Already her hands were in my lap, stroking and fiddling with the clasp, and then she dropped to her knees, pulling my jeans and boxers with her and leaving my erection open to the naked air for the first time in the presence of another person.

It didn't stay in the naked air for very long as Red took me into her mouth, bathing me with her tongue. My eyes rolled back into my head and I slumped against the wall as I experienced my first blowjob. My hormones were exploding out of my brain and soon the enclosed little space was filled with the smell of sex and pheromones.

Red paused for just a moment, looking up into my eyes and then back down at my waving dick, shining wet from her saliva. "I can't believe I'm doing this," she muttered to herself. But then her eyes rolled back into her head and she moaned as she took my cock back into her mouth.

After only a couple more minutes, Red stood up, then slipped her skirt to the floor and stepped out of it. She turned around, leaned against a cleaning supplies closet, and finally shoved her bare ass back at me.

I took a quick look around at our surroundings. Not the place I expected to lose my virginity, not with a girl I'd only met the previous day and didn't even know her name. But I was an eighteen-year old male and I wasn't going to pass this up. So I stepped up into position, one hand on her ass and the other on my shaft to make sure it got where it was headed, and then began to spear my way inside of my very first pussy.

Oh, I was in HEAVEN. Red let out a low moan. And then the sounds never stopped coming out of her mouth for the next ten minutes as I pulled back and then slammed my way back in, my pelvis slapping against her tight cheeks. I was very glad that this wing was always less crowded than most in the school. It was far less likely anyone would overhear and come to catch us. Over the next few minutes, trying to balance maintaining my rhythm while exploring uncharted territory, I managed to work her shirt up to her chin and unsnap the bra so that it hung loosely around her neck, my paws groping her firm tits.

After a few minutes, she came in a rush, sounding a guttural scream that rattled the metal shelves in this little space, followed only a moment later by my own eruption within her velvet walls. It poured and poured out of me, until at last she slumped down to the floor, leaking my juices between her legs, panting as she tried to catch her breath.

She turned to look at me, still dazed, flushed with our exertion.

I just gazed down at her, my first conquest, the fire in my loins momentarily under control but far from quenched. My gaze swept across her perfect ass and the flat, muscled cheerleader belly up to the lower curve of her breasts, still visible. I already felt liquid lust burning again in my veins and steaming off of my skin.

"What's your name?" I asked her.

"Ashley," came the husky reply.

"Ashley, I'm not done with you yet."

She half-smiled, half screamed with fear as I swept her up into my arms, planting her back against the supply closet, spreading her legs. She showed off her flexibility by lifting one leg high into the air as I lowered my hips under her and then thrust upwards to spear my newfound erection into her still juicy slit.

We grinded against each other, banging against the metal as I lifted her shirt up with my teeth before burying my face into her bosom. We kept fucking for a good bit longer that time, finally ending up with me sitting on the floor as Ashley rode in my lap until she'd found two more orgasms and I'd added a second load of my spunk to the cocktail inside her pussy.

We cleaned up as best we could. Good thing there were plenty of paper towels in that closet. Then we snuck out to before this class period ended.


The first semester of my senior year went by in a blur. I studied enough to get by. I integrated myself into a new circle of friends (my relationship with Ashley exceedingly helpful in that regard). And I got laid as often as possible, which unfortunately, was still not enough.

Despite my initial impressions, Ashley was far from being a slut. I was only her second lover, and that previous one had been over six months before me. And despite us settling into a comfortable and flirty dating-relationship, I still had to beg and cajole for every square inch of her body I got. We had to sneak around both of our parents, screwing in my car or other student hideaways. Only that first time, within days of meeting her, did I ever get laid quite so easily. I didn't know why she was so assertive that day, but I wasn't one to complain about my good fortune.

This situation was not helped by the fact that Ashley had several very hot friends. Becky, in particular, had caught my eye less than a week after Ashley and I had hooked up. While she didn't have the curves Ashley possessed, Becky still had a very cute face and an incredibly toned body. On top of her dark brown eyes, accented with an alluring dark eyeshadow, and light brown hair always in a ponytail, Becky exuded athletic confidence with every step, and had an aggressive flirtiness that quickly won me over.

I never really thought about cheating or anything, but sometimes, when a group of us were out, I found myself idly staring at Becky. Inevitably, she would somehow sense my gaze, then turn and look at me through heavy-lidded eyes, her mouth ever so slightly agape in a soft, arousing pant. And just when my blood reached boiling point, and I felt about ready to assault her, she would shake her head, blink her eyes, and then be the same old tomboyish-flirty Becky.

By semester's end, I think Ashley was starting to realize her boyfriend's mind was drifting away towards potentially greener pastures. It was during Finals Week, a period of intense stress, that she decided to reinvigorate our relationship and let loose a little steam from both of us.

Becky and I were in American History together, and we had been studying together for most of the semester. We had just finished the Final, and were trudging through the hallways when we ran into Ashley and the rest of her crew. Ashley kissed me hello, and then wrapped her arm around me, tugging me away from the crowd. I thanked Becky for her help that semester (History not being my strong point), and she winked at me a flirty "my pleasure."

One of Ashley's girl friends reminded her that Ashley's own Final started in less than twenty minutes. She nodded, and then continued to pull me deeper into the bowels of the school, until I realized our destination.

With Finals in full swing, the only classrooms used were the large lecture halls that could accommodate a few hundred students. The wing with the smaller classrooms, and our Maintenance closet, would be completely empty.

Not once, but twice, I thought I heard footsteps behind us, but when I turned I saw nothing, and then Ashley was tugging me forward in more of a hurry. The instant we clambered inside and got the door closed Ashley sat me down on a workbench and started tugging my jeans down. Once she extracted my tool, she simply lifted her skirt and just shoved her panties to the side, straddling my lap and sinking me into her in one go.

She moaned happily, and then started to bounce in my lap. "Hurry up and come. I've gotta get to my test soon..." Ashley had the foresight to lift up her shirt and bra cups out of the way, baring her fabulous bosom to my gaze, assuming (correctly) that the sight of them would rocket me off towards eruption much more quickly.

We fucked hard and we fucked fast, my hands on her hips, jackhammering her until her boobs gyrated up and down enticingly. Her legs were crossed behind my back, squeezing with every pull to grind her clit into my pelvis. Within five minutes, she clutched my neck and squealed out her climax. I grunted at her and she dismounted me quickly, just managing to stuff my meat into her mouth before I came, spraying the inside of her mouth with my juices as she swallowed for all she was worth.

Once I was done, Ashley sat back on her heels, letting out a sigh of satisfaction. Then, checking her watch, she fixed her clothes back into place, gave me a peck on the cheek, and then bolted out of the door to rush off to her Final.

I leaned back against the wall, a smug satisfaction on my face. That was a great way to let out some Finals stress.

I was still slumped back, basking in my own post-coital afterglow when the Maintenance door opened once again. I felt a momentary panic flood my brain, half-expecting a grizzled, mean janitor. But when Becky's cute face popped into view, I felt a wash of relief.

"Done already? Ashley talks about you like you're a marathon man..."

"Hey, I could go on forever if you needed me to," I retorted, instantly defending my manhood. Then I realized the rather improper discussion we were having.

"Really?" Becky's grin was feral, a gleam in her eyes. She stepped inside and closed the door, and before I could get another word out she had lifted her shirt up and off of her head, tossing it into a corner of the little closet. She was already reaching back to unsnap the bra.

"Uh... Becky?" I stammered, natural uncomfortability and trepidation swelling up momentarily. But then I felt the wave of lust fighting back as my teenaged hormones surged into overdrive at the sight of a fresh pair of firm, succulent tits.

"Mmm hmm?" Her shorts were next, kicking them and her panties off, leaving her wearing nothing but her tennis shoes.

Despite my conscience, I felt the blood returning to my lower extremities and rapidly filling my other head. "Should we be doing this?"

"Probably not. But then, after that test, going on forever sounds like a fantastic way to unwind." She pivoted and bent forward at the waist, leaning against the wall and pointing her perfectly toned, athletic, tight ass back at me. I watched her dip a hand to her already moist pussy and begin stroking herself. "You DID say you could go on forever if I needed you to."

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