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Knocked Up on Valentine's Day: A Single Dad Billionaire Romance by Amy Brent (138)

CHAPTER ONE: Judith “Jude” Allen

I was always super smart in school. I breezed through junior high and high school with straight A’s without ever cracking a book, and I had major universities across the country lining up to offer me academic scholarships.

I opted to go to Midwestern, which I chose because it was clear across the country and thousands of miles away from anyone who had a clue who I was. I loved the idea of moving to a new town and starting over. It would be like being reborn, being washed of my sins, leaving all the heavy baggage of my old life behind.

They say that when you go away to college, it’s a chance to reinvent yourself, start new with a clean slate, shuck off your past dirty deeds and start anew, and that’s exactly what I wanted to do. I had established a somewhat dicey reputation for myself in high school that I knew would weigh like a heavy chain around my neck if I chose to stay in Clarksford. The slut in high school becomes the slut in real life. That was not the life I would choose to lead. I was not ashamed of the things I’d done, but I didn’t want them following me around like a ball and chain the rest of my life, which would happen if I didn’t move away.

Going to Midwestern would give me a fresh start without a reputation, even if that reputation was well-deserved. Plus, Midwestern had one of the country’s best psychology programs. I wanted to be a psychologist, which required a Bachelor’s degree with a psychology major, then a Masters degree. Maybe I’d even go all the way and get my Ph.D. and become a psychiatrist or a doctor of some kind.

Getting my Bachelor’s seemed like a million miles away when I first started, and even now, nearly four years later, there’s still so much more work to be done. So, for now, my sights were set on getting my Master’s degree within the next two years, which meant I would start the Master’s program in the fall, but could take classes over the summer if I chose to, and that would speed up the process. I hadn’t made the decision to take summer classes yet. I’d look at the curriculum when the time came to see if anything struck my fancy.

If I didn’t go to school over the summer I could pick up more hours working nights as a waitress at the Pink Pony, the off-campus dive bar popular with students and the “cooler” faculty members (yes, professors and students do fuck, shocking huh). That would let me stock away a little cash and blow off some steam at the same time. Plus, I got to drink and eat for free at the Pony because Duke, the fifty-something owner/manager, wanted to fuck me.

Hell, Duke wanted to fuck every girl who walked in the door, whether they worked for him or not. But he wanted me most of all because I made him want me. I knew how to manipulate a guy like Duke. Id been doing it my entire life. I could make his pudgy dick hard with just one dreamy look or by running my tongue around my lips. A little shake of the ass, a little bending over in front of him, a little leaning down so he could see my tits down the collar of my Pony t-shirt. Duke was putty in my hands. Which was why he wanted my pussy on his cock.

Duke figured the way into a girl’s pants was through her stomach, not her heart. Even though his hair was shaggy and gray, and he was kind of greasy-looking, he was also kind of sexy in a “Sons of Anarchy” sort of way. And he made a mean bacon cheeseburger, so we’d just have to see how things progressed.

Anyway, within six years of leaving home I could acquire both my Bachelor’s and Master’s at the same school and graduate with honors. I could probably do it in five years if I really pushed myself. Then again, that would leave me little time for the fun things in life; those things that had driven me away from home in the first place, but all work and no play makes Judith a very sad girl.

Like me, lots of people who choose to study psychology do so just to try and figure out what was wrong with themselves. Yes, supposedly broken people study psychology hoping to fix themselves. I wasn’t entirely convinced that I was broken, far from it, but I wanted to know why I thought the thoughts I thought. Why did I do the things I did? Why did I say the things I said?

Broken people have broken thoughts and do broken things, some experts say, even when those things might be self-destructive to themselves or hurtful to others. It’s all about momentary pleasure, at least for me. I was not psychotic or psychopathic or sociopathic or misanthropic, but sometimes my brain commanded me to do things that I knew were not good for me, things that I knew would have negative effects on me and those around me, yet I did them anyway because they felt so fucking good. In modern terms, I was addicted to sex. In a single word, I was a nympho.

It was in asking myself why I did the things I did and why I thought the thoughts I thought and why I got extreme pleasure in things that a “normal” person might consider abnormal that got me interested in psychology and how the human brain works, more specifically, my brain.

I figured studying psychology would help me explain myself to me. To quote the therapist I had been seeing since I was fourteen-years-old, I had certain “personality quirks” that greatly affected my actions regardless of the consequences.

Why did I do those things? What the heck was I thinking? And the biggest question in my mind: who the fuck was I hurting? I mean, if it felt good and everyone involved got off on it, where was the harm?

Anyway, sorry, my mind tends to wonder when the subject of sex comes up, which, I my mind, happens often.

So, the original plan was that I’d be in school at least six years, or until the scholarships, money, and interest ran out. I tended to get bored easily, which was a symptom not of any disease. It was a tendency of someone with a high IQ, at least according to the tests I had taken in high school. I had a near-genius IQ. I could be anything I wanted, according to my guidance counselor. A doctor, lawyer, dentist, economist, scientist, president, whatever.

“You can be anything you want to be, Judith,” Mr. Curtis, the guidance counselor said as we met in his office after school toward the end of my senior year. Mr. Curtis was probably my dad’s age, though he was aging better than my dad. He had a thick head of black hair and more muscle than fat on his tall frame.

He was an assistant football coach, newly divorced, probably broke, sleeping on someone’s couch, spending money he didn’t have in bars trying to get laid. Poor Mr. Curtis needed a little light in his life. And I wanted that light to be me.

Mr. Curtis arched his dark eyebrows and gave me an expectant smile. “So, what do you want to be, Judith?”

“Jude,” I said quietly, my heartbeat starting to pound in my chest. I could feel my breasts swelling, juices pooling in my cotton panties. I slid out of the denim jacket I was wearing and let it hang on the back of the chair. I gave him a slow blink and smiled. “Call me Jude.”

His Adam’s apple bobbed. I wasn’t wearing a bra. My dark nipples were pushing against the thin white t-shirt like dark gumdrops. I caught him looking at them. He swallowed hard again.

“Um… okay, Jude… um… what would you like to be?”

Without skipping a beat, I stood up, closed and locked the door, then peeled the t-shirt over my head. Cupping my big tits in my hands, thumbs rolling over my stiff nipples, I licked my lips and said, “I want be teacher’s pet.”

* * *

I think my fascination—and lust for— teachers started in the eighth grade, specifically in Mr. Wheaton’s basic algebra class. I was thirteen or fourteen at the time and puberty was having a ball ravaging my body. I had always been a skinny kid, but over that previous summer my boobs had grown several sizes and red curls had started sprouting between my legs.

That was also about the time I started exploring myself with my fingers and anything else that was long and smooth and felt good going in and out, in and out, in and out, like my mom’s “neck massager”, which was really just a vibrator in the shape of a smooth tube.

It sounded like a diesel engine when switched on and had to be plugged into the wall, so I only used it when I was left alone. As soon as mom and dad would leave the house I’d grab that baby and head for my bedroom. I’d lock the door, plug it in, crank up the music, and go to work, driving myself over the moon and back again with wonderful electrical sex.

I was always horny back then (kind of like now, duh) and would just start gushing in my panties for no reason at all. I’d rub myself against the cross bar of my bike, I’d lean against the washing machine, I’d get my dad’s electric razor and… well, you know.

But I found that I was most horny when I was at school, not because of all the boys and the attention they offered a horny girl whose tits had come in full bloom, but because of the teachers.

The teachers… sigh…

More specifically, the male teachers.

Older men.

I loved older men.

And when you’re fourteen, anyone over twenty-one fell into the category of older man.

Mr. Wheaton—Andy was his first name— was my first true love, and my biggest regret in life is that I never fucked him or had his cock in my mouth. I mean, I was like fourteen and he was twenty-three so there would have been severe consequences for him if we’d been caught. And I was not the full-blown sex maniac with a body to match back then. I had big tits, but I also had a layer of baby fat and pimples on my chin. The boys were always trying to feel me up and talk me into giving them hand jobs or blowjobs under the bleachers, or letting them finger me on the back of the bus, but to Mr. Wheaton I was just another pudgy girl too young to be noticed.

So, I settled for having amazing sex with him in my mind, which I did every night in the ninth grade, so much so that I started calling my right-hand Andy.

We’d have little conversations.

“Hi, Andy, would you like to feel my tittie? You would? How about sliding your finger in here… yes… just like that… oh Andy… in and out… in and out… oh… Andy… you dirty boy…”

Since I couldn’t legally have sex with Andy Wheaton, I decided to have sex with a tenth-grader named Toby Osgood, not because he was the best looking or the most popular boy in school, but because he was convenient and hopefully as horny as me.

Toby was my next-door neighbor and we had been best pals since birth. Like me, he was a nerdy teenager with bad skin and Coke bottle glasses and a mouth full of braces. He was short, probably five-foot-nine, and didn’t weigh a hundred pounds soaking wet. We had been classmates since kindergarten and our moms were best friends, so it seemed that we were always together. My mom even had pictures of us in the tub naked when we were toddlers after she’d caught us making mud pies in the backyard after a rain storm. That picture always embarrassed the crap out of Toby, but I thought it was cute. I even gave him a framed copy as a joke one Christmas. He did not see the humor. Nor did he display that photo anywhere that I ever saw.

I didn’t bother asking Toby if he’d like to have sex because I didn’t want to risk being turned down. So, I had it all planned out. I asked him to go to the movies one Friday night to see Juno, a comedy about a cool teenage girl who gets knocked up by her dorky boyfriend.

In retrospect, that probably wasn’t the best movie for us to go see because later, in the basement at his mom’s house when I was trying to talk him into putting his hand down my pants, Toby got a look of horror in his eyes that told me things might not go as planned.

“What’s wrong, Toby?” I asked in a warped attempt at seduction. I rubbed my hand up and down his thigh, gazed up at him and batted my eyelashes. “Don’t you want to fuck me?”

“Gee, I dunno, Jude,” he said, his voice cracking as my palm slid over the boner hidden in his jeans. I was a little surprised at how big and hard Toby was, given that he was just fifteen and had yet to sprout a single hair on his chin or chest. I know because we went to the public pool every day in the summer. The best words to describe Toby were “skinny” and “white”.

He swallowed hard and gasped when my fingernails dragged across his balls. “I mean, what if I knock you up? Like that movie. We’re too young to be parents. Jesus, the thought of baby shit makes me wanna puke.”

“I got that covered,” I said with a devilish grin. I slid two fingers into the back pocket of my jeans and came out with a condom I’d stolen from my mom’s nightstand. It was wrapped in a purple plastic package with the words “BARE BACK RIDER” printed in neon orange on the front. I wiggled it at him. “Or more appropriately, I got you covered.”

He licked his lips and swallowed hard again. “Okay, I mean, if you’re sure you want to, I guess we can give it a try…”

“Oh, I’m sure,” I said, tearing open the condom wrapper with my teeth like I’d seen them do in the movies. I made a sour face and smacked my lips. It tasted yucky, like oily rubber. Gross!

I had done my research online in preparation of our big night. I had watched this porn star put the rubber in her mouth, hold it between her lips and teeth, and slide it over the guy’s cock with her mouth. It was a hell of a magic trick that I could not perfect. I had practiced on another rubber and practically swallowed the damn thing. Plus, it tasted like shit! I nearly choked to death! Can you imagine, having to run into the living room where your mom and dad sat watching Friends and turning blue because you were choking on a rubber? Nope, no showing off for me. I took the rubber out of the package, shook it out fully and held it out to Toby. It dangled from my fingers like a wet noodle.

“Okay, put this on your dick,” I said, trying not to frown.

“Aren’t you supposed to do that?” he asked, trying to be cool. I guess Toby had been watching the same porn.

“Jeez, Toby, I’m not gonna do everything,” I snapped. “Do you wanna have sex with me or not?”

“Well…”

“Oh, for petesake!” I held the lip of the rubber between my teeth because I didn’t want to lose it in the couch cushions and told him to lean back while I undid his belt and jeans. What popped out of his pants shocked me a little. In fact, the look on his face told me that it shocked us both. He blinked at himself, then looked at me with a “Wow, would you look at that sucker!” gleam in his eye. It made me smile. And made me think I’d made the right choice. I was glad I’d chosen Toby to be my first.

The rest, well, you’ll have to imagine that for yourself. Let’s just say things were going fine until Toby popped his cork way before I was ready to pop mine, I mean, literally within three seconds of entry, as the rocket geeks would say. He was so embarrassed he jumped off the couch and ran out up the basement stairs, leaving me sitting on the couch with a condom hanging from my peach-fuzzy cooch and a bewildered smile on my face.

I mean, I had to smile, right?

It was funny in a Hollywood teen movie sort of way.

But it was also sad because this wasn’t a Hollywood teen movie.

This was my life.

I guess it was sad and funny.

I felt really bad for Toby, but at least I was no longer a virgin (that happened quickly because I think I’d loosened that sucker up with mom’s neck massager, thank goodness). The sad thing was that I had yet to have my first orgasm with a man. To be fair, Toby wasn’t a man at that moment (he would be gorgeously hot in a year, but too preoccupied with other girls to pay any attention to me).

At that moment, he was just a boy and I was just a girl, more curious than anything. Okay, horny and curious, but what we’d done—or attempted to do—was being done by teenagers at that moment all over the world. Why shouldn’t we have a little fun, too? I just hoped things went a little better for them. Maybe my first should have been a twelfth grader…

Things between me and Toby were never the same after that night. We never talked about it or attempted to do anything like that again. We remained friends throughout high school, though I could feel Toby pulling away soon after that night. We barely spoke his senior year, but our little romp in the basement was always there at the back of my mind, like a nice childhood memory that made me smile. And a little sad.

As luck would have it (luck can be such a bitch), Toby sprouted the next summer. He gave up his Coke bottle glasses for contact lenses, his skin cleared up, and he grew three inches taller, to just over six feet. He started lifting weights, got all lumpy, and made the varsity football team. He hooked up with a cheerleader named Candy Olson his senior year and they fucked like rabbits, I’m sure. The last time I saw Toby was at his graduation. He had Candy hanging off him like a cheap suit, so we just waved at each other and silently said our goodbyes.

That was four years ago. I had not talked to Toby at all over the years, but I was pretty sure he’d spent that time playing football for Mizzou and screwing cheerleaders. He had graduated last spring, but I had no idea where he was or what he was doing.

And I was still chasing teachers.

I mean, professors.

The only difference between then and now was that I had slept with every man I’d crushed on. I had all the right equipment and knew how to use it. That “rubber between the teeth” trick? I mastered that fucker years ago. I learned that the trick was using flavored rubbers that didn’t taste like crap. I could even hold a condom between my pussy lips and let the guy slide inside me without ever knowing he had a condom on. I know… amazing, right?

I no longer hesitated when I saw a teacher I wanted to fuck because in my mind, life was too short and the nights were too long. When a teacher cranked my tractor, I made sure he was available (I’m not a home wrecker, for petesake), and went after him all out, no holds barred, nothing held back.

Innuendo and subtle hints were for people with far more tact and self-control than I had. If I wanted a man, I went for it. What’s the worst he could do? Say no?

You wanna know how many men have turned me down?

Zero. Thank you very much.

The only question in my mind was, which teacher would I be fucking next.

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