The Chronicles of Ben Merriman #01

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18-year-old PI meets a cheerleader & a hot, wealthy blonde.
16.5k words
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108.3k
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Part 1 of the 2 part series

Updated 10/29/2022
Created 02/05/2011
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Short Story: The Chronicles Of Benjamin Merriman #01

Author Note: This story is an original work of fiction. All characters featured herein are at least eighteen, if not expressly stated, and certain characters may also be found in other works by the authors, published or forthcoming. Feedback is desired and greatly appreciated. Email comments to the address in our profile. Thank you for reading.

Copyright 2011 by Jack and Josephine Cutter.

This story stars: Benjamin Merriman, and features Caroline Cassidy, Courtney Daly, Jacquelyn Atkinson, Robert Phelps, Melissa Golding (unnamed), and Frank Merriman.

This story contains: male-female erotic couplings, fellatio, cunnilingus, anal and analingus, cheerleaders, bikinis, male dominance, deadbeat dads, socialite brides, philandering fiancés, beautiful women, and a budding private detective with significant sexual skill.

This story begins on Friday, September 9th.

* * * * *

It goes without saying that my high school life was not what you might call normal. I was eighteen and a senior, and that is where much of the normalcy ended; typical high school seniors do not have the kinds of experiences that marked my first year of official adulthood.

They do not have to deal with crime rings, sleazy politicians, wealthy socialites, corrupt cops, dangerous criminals, deadbeat dads, missing persons, corrupt cops, illicit dealings, breaking-and-entering, infidelity, secret gambling halls, drugs, high-priced escorts, underground brothels, etcetera, etcetera. I've dealt with those things and more, and all before I graduated.

My name is Benjamin Merriman . . . and these are my stories.

The Chronicles of Benjamin Merriman, Volume the First

It is my belief that each person in the world is blessed with some definable characteristic that sets them apart from the rest. An inherent advantage, above and beyond the norm. Some might be blessed with unusual speed or strength. Others might find they possess heightened intellectual. Some such talents are easily discovered, but many are difficult and thus never fully realized. Mathematical skill, brute power, keen wit, an artistic eye; these things are definable blessings, and if you look back through the annals of history, you'll find plenty of folks who had them.

I'm going to go right ahead and be honest with everyone from the beginning, and likewise throughout; I've got a few special talents myself, but there is one above the rest: it seems I'm blessed with an inordinate amount of luck. Simply stated, I'm a pretty lucky guy; things always seem to work out well for me, no matter how difficult they might seem.

Take high school, for example.

It did not begin well, let me tell you: my first two years were not the best. I was invisible, a tall, gangly kid with skin troubles and a warbling voice. Girls, therefore, were a complete non-starter. Introverted, shy, unexceptional in every way, and with limited fashion sense, I was the typical invisible high school male, quietly walking the fringes. It was what I knew, however, and I was content with my situation because I knew nothing different.

The summer between my sophomore and junior years, however, changed everything. Physically, I sprouted: my body filled in, my gangly limbs took on definite shape, my skin cleared up, and my voice deepened into its adult range. A series of interesting and rather fortunate events, which shall be later revealed, really did a positive number on my self-esteem, too: my confidence grew by leaps and bounds, to the point where by the time I returned to school the following September for the start of junior year, I was a completely new person.

High school is high school, however, and once established roles and reputations die hard; my transformation went largely unnoticed at first by the students at my school. While I did start to get my fair share of odd, who-is-that-guy-and-where-did-he-come-from looks from a few of the more astute girls as junior year wound down, I remained mostly a fringe-guy, content to slip through the high school cracks. I can honestly say it did not bother me, for while the girls inside my own school did not pay much attention to me, girls outside the school certainly did -- and those girls had no knowledge of my unimpressive formative years. Let's just say my confidence was high.

It wasn't always this way, however.

Like I said, before that fateful summer times were tough, and not just at school. My mother passed away when I was eight years old, leaving me and my father and my older sister to figure things out as best we could.

My father is Frank Merriman, forty-six years old, and he owns Discretion Investigations, a private investigative firm here in my beautiful home city of Los Angeles. We're based out of Beverly Hills, which is nice as it provides my father plenty of wealthy-person business. My dad is an ex-cop, which means he is well-informed, well-connected, knows his way around, and is very good at what he does.

My sister's name is Keri. She's twenty-two years old and will soon be graduating from the University of Southern California, and she's going to be a lawyer. She is currently applying to lots of big-name law schools. My father says she looks exactly like her mother, which must have been awesome for dad because everyone pretty much agrees that my sister is one of the hottest females on the planet. For a pair of opposite-sex siblings not too far apart in age, I have to say the two of us have always been close, which is really nice and has helped me greatly over the years.

After nearly a decade, Dad finally remarried last year, which is an interesting story and worth recounting. My mom and dad were sweethearts from a very young age, and he's always made no bones about the fact that my mother was the one true love of his life; this, of course, turned many women away from a man who was, to use a rather overused cliché, the most eligible bachelor on the block.

While some women might (and did) feel threatened by or uncomfortable with a man who puts such information out there, Angela proved a different sort right from the start. She's thirty-six with an early twenties body, blonde, beautiful, and pampered, and that's exactly the way she wants it. My father has money, she wants money, neither is looking for love everlasting, she gets the creature comforts, and my dad gets a gorgeous wife in the sack every night. It's a fantastic arrangement. In fairness, Angela is also a nice woman, very easygoing if a little spoiled, and she and my father make each other very happy.

Heather, however, is another story all together. Angela's eighteen year-old daughter is a real piece of work: hot and blonde (just like her mother), but a total bitch. She's not only hot, she's hot and she knows it, and she acts like she knows it. I can count on one hand the number of times I've talked to her for longer than two minutes in the past year. She couldn't care less about unimportant people, which is practically everyone, and lets the unimportant people know it.

Back to me for a bit.

It's well-known that ever since I was old enough to walk, I've wanted to follow in my father's footsteps. While my father has not tried to encourage my interest in private detection and investigation, allowing me the luxury of deciding for myself, he has not discouraged it, either, and I know he is excited by the prospect of having his son follow him into the family business.

One of my counselors at school once asked me how I thought a shy and introverted guy such as myself could possibly become a private detective, where it would seem such qualities would be a hindrance. They are a hindrance, of course, but not for me; you know how some people act and feel in different ways given the circumstances? That's me. In school, my school, I'm still the shy and introverted guy I've always been. Like I said, it's hard to shake reps in high school once they've stuck. Outside school, however, I'm the complete opposite: no problem talking to girls, outgoing, aggressive, confident.

It's an interesting dichotomy.

The deal with my dad was this: when I turned eighteen and it became legal for me to do several things important to investigative work but not permissible by law for minors, I could begin training on an official basis with my father's firm -- I'd be unofficially training for years, of course. He also did this to ensure I got decent grades, which I could have gotten standing on my head in the corner all day long; school was always just an easy thing for me.

Well, the bottom line is I turned eighteen on August 09, and as such that is when my story begins to unfold. The speed at which things began to happen truly amazes me, thinking back on it, and I doubt anyone would have guessed that one year later, I'd be where I am right now.

The Discretion Investigations team is as follows: Veronica Thompson, 28, a member of the investigative team who has been with the firm for six years; Beau Nivens, 38, one of my dad's best friends, has been with the firm for twelve years, and became a family friend after my dad busted him as a kid trying to boost car stereos in South Los Angeles; Harriet Edmonds, gray-haired and grandmotherly, the firm's administrative and secretarial person; and last, but certainly not least, is Caroline Cassidy.

Caroline deserves her own special paragraph, because throughout my most important teenage years (fourteen, my age when she was hired, to eighteen, my current age), she has held the distinction of "Go-To Fantasy Girl". In other words, most fantasies I've had growing up, as long as I have been having fantasies, have involved Caroline Cassidy.

When I turned eighteen, Caroline was a newly minted twenty-four year-old. Perhaps I should describe her for you: take Marisa Miller's body, add Brooklyn Decker's fantastic tits, and the incredibly sculpted ass of Jessica Alba, and then imagine the hottest chick you've ever seen with natural, golden blonde hair and bright blue eyes, and maybe you have an idea of just how smoking hot Caroline is. The woman is a fucking Barbie doll come to life.

A goddess, in other words.

Which is why, of course, she is a complete and utter ice queen. Not a bitch, mind you, because she does not go out of her way to be mean to people, but an ice queen. When you're that hot, you're allowed to be. To clarify further just to make sure you understand the distinction, she is not a bitch like Heather, who feels superior and acts like it; Caroline is simply not interested in dealing with the crap of other people, nor making pleasant chit-chat with them, nor pretending to be interested in talking to them.

However, she is very intelligent and very perceptive, and an excellent detective (not to mention an excellent writer who has done some free-lance work for the Los Angeles Times and uses information connections there to help with her tougher cases).

Everyone at Discretion knew my eighteenth birthday meant I was joining the team. Unfortunately, the only one who was not that excited about it was the one person I was most perpetually excited about. My father had told Caroline some time ago that she would be primarily responsible (along with himself, of course) for overseeing my training. It was the way at Discretion: the youngest member of the team trains the rookie. I, of course, was thrilled, since it meant spending more time than I'd ever thought possible with Caroline.

Basically, I was to act as her shadow, which was fine by me.

Case File #001: The Case of the Deadbeat Dad

My first real day on the job came one month to the day after I turned eighteen, late on a Friday night in early September. I remember this clearly because when Caroline called, there was warm flesh next to me and I had to leave it behind.

The girl's name was Courtney and she was a senior at West Mountain School, one of several ritzy elite private high schools in the Los Angeles area. My school, Rembrandt, had played its first varsity football game of the year against West Mountain earlier that night and I, being a football enthusiast, attended the game along with several hundred other fans.

I noticed her almost immediately (she was an opposing team cheerleader, after all, and it is requisite at games to size up the opposing talent) and could not take my eyes off her. She was a petite brunette with perky breasts and lovely light brown eyes, but that was not what hooked me; cheerleading outfits leave very little to the imagination these days, to the delight of all males in attendance, and this girl had an excellent rump, apple-shaped and very tight.

I'll admit it openly, I ogled her ass all night long.

By the way, I'm not a virgin. I reached my milestone of manhood at the hands my sister's best friend, who sort of acted as my personal sex teacher with, surprisingly I would later discover, my sister's consent. It happened in the midst of my physical transformation, and spurred my mental one. Since then, I've experienced two sorority girls at USC (also friends of my sister, who showed me even more of the ropes), plus a handful of high school girls. None of the those were from my own school, of course; the girls there would probably have died of shock if they knew how experienced I was, as my social status at Rembrandt at the time was one small step above invisible. Which, I must admit, was fine by me.

Back to Courtney, I waited for her in the parking lot after the game. Most of the cars were gone by the time the cheerleaders came out of the stadium side entrance, where the visiting locker rooms were. She was with three other girls, still in her cheerleading uniform, and they noticed me watching them right from the start.

I was leaning against my car (a black Range Rover, which girls love), dressed in jeans and a leather jacket, looking older than my age and feeling pretty good about it, I have to say, and smiling in a particularly mischievous way. West Mountain had crushed us, of course, which meant Courtney and her friends were in good spirits, which I felt could only help my chances.

The girls giggled and whispered as they walked toward me, but stopped a few feet away. One of them said, "Why are you staring at us?" There was a grin on her face.

"I'm not," I said.

The girls giggled again. "Yes, you are," another girl said.

I grinned and looked Courtney right in the eye. "I'm not staring at you," I told them politely, "I'm staring at HER."

Courtney blushed but her eyes, wide and wondering, never left mine, and I knew I had her. The other girls were a little disappointed, but continued the game for their friend, which I admired.

"At Courtney? She's out of your league," the first girl said. It was a good response, and I made a mental note to circle back to that girl, a redhead, sometime in the future. She was hot, too, after all, but right then I wanted Courtney, whose name I now knew.

"She's out of most everyone's league," I replied, "but that might get very lonely. Every now and then, beauty needs to slum it."

Courtney blushed again and the girls giggled.

Long story short, in a few minutes Courtney and I were in my car heading off to find a quiet place to park and talk. Which we did, because I am a gentleman, and I always get to know someone at least a little bit before engaging in carnal congress.

Twenty minutes after that, however, Courtney was squirming in her seat. She was a hot little piece, I have to admit, and very ready for what we both knew was coming. When I kissed her for the first time, she whimpered softly with need, and it only took a short time after that before she reached between my legs and easily found my zipper.

Clearly, despite being only eighteen herself, she was not unaccustomed to cock, which was excellent. I started the engine as she unzipped and reached in, her dainty French-tipped fingers trembling (all rich girls go French-tip) as she gently withdrew my manhood.

At which point she smiled happily, noting my size; it's not a behemoth, but at just over seven hard inches it is longer than many, and decently thick, and definitely makes girls feel good. It also helps with my confidence; four inches limp is nothing to cry about.

Courtney's fingers wrapped gently around the base of my shaft and it pulsed in her hand, and she giggled softly. It was a reaction I was not unaccustomed to. She worked her fingers slowly up the length, squeezing at intervals, more inspecting than trying to make feel good, and she could feel it beginning to grow in her hand. When she reached the mushroom head, she pinched it from various angles, and something clear and sticky dribbled out from the small opening.

With one hand firmly holding my rapidly stiffening shaft, Courtney cupped my sack in the other. My balls are large, too, and sensitive, and she began to probe and prod and press and squeeze each of my testicles between her fingers, which felt really good.

No blushing virgin she, the girl definitely knew her way around that region. I was hard in no time. She stroked it slowly a few times at its full length, and I sighed and struggled to focus on the road as she lowered her head into my lap.

I'll tell you, there's nothing like that moment right before a girl's lips wrap around your cock. My heart was pounding and nearly burst from my chest when I felt her graze her mouth over the mushroom head, and I groaned loudly. A hot young slut in a cheerleading uniform I'd known for less than an hour was peppering my shaft with feather light kisses and blowing gently on it. She licked around the head, her tongue like a butterfly's wings as it fluttered about the tip.

In moments Courtney took the head into her mouth and began to suckle it gently. I sighed again (what else to do besides sigh and drive) so she would know I was enjoying it. I had to admit she had excellent technique; when she began to swirl her tongue slowly around the head, I knew she was a real talent.

I put my hand on her as I drove and caressed the small of her back, where the uniform bared her flesh. Her skin was flawless and it felt good on the palm of my hand, but whatever she was doing with her mouth was even better, the most incredible feeling. I knew if she continued like she was, I would not last, which was fine by me. My hand went up to the back of her head and I gently pushed her head down, so she could take more of my cock into her mouth.

Courtney had likely not been ready to take me deeper, but she was so talented she did not resist. My cock slid inch-by-inch past her moist glossy lips and filled her warm, wet mouth. She firmly gripped the base of the shaft and started to lift her head up. I was having great difficulty concentrating, but steadfastly kept my gaze fixed on the road.

Courtney held the tip in her mouth and started her tongue around it again. She took me out of her mouth and began to lick the underside of my cock up and down in long sensuous stokes. This drove me wild, and soon I realized it would be all over. She must have realized it, too: her fingers started to work up and down my cock much faster.

She took me back to her lips and then, incredibly, and for what seemed like an instant and somehow endless moment, slowly slid her lips down my shaft until she had the entire length of my cock in her mouth. That, my friends, was incredible; seven inches of rigid manhood. She worked her lips and tongue vigorously up and down while she held the base, letting her fingers stroke my balls as she hummed softly to herself.

I was in heaven. Courtney was expertly sucking me towards climax, her brunette head bobbing up and down in my lap. She pretty much went to town at that point, sucking for all she was worth, and I felt the familiar stirrings.

Put a fork in me, I thought, I'm done.

I exploded into her mouth, which I am still not certain she was prepared for. She took it like a champ, though, after a moment of surprise, gulping down ropes of my cum like a newborn babe at the breast. Cum trickled down her chin, and once she was through with the main blast, she pulled back and wiped it onto her finger.