Office Fling

by Amy Brent

  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 mad
e 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.

  CHAPTER TWO: Professor Holden Moss

  I know, I know… I shouldn’t sleep—or have sex with—my students.

  I know, I know… it could get me fired and possibly arrested.

  I know, yes… I’m old enough to be her…

  Older brother, maybe, but come on, have you seen this girl?

  Holy hot babes, Batman.

  Who could resist this girl?

  Haley… Haley… something or other…

  She sits down front in my Advanced Psychology class every Friday at three.

  Always wears a short skirt that she doesn’t bother tugging down over her crotch when she sits.

  Tan, toned legs.

  High heels.

  Bright red toenails.

  Sits with her legs spread.

  Doesn’t wear panties.

  Keeps her pussy shaved clean.

  Holy. Fucking. Shit.

  If you could resist that, my friend, you’re a better man than me.

  Haley... what the hell is her name... ROGERS! That’s it. Haley Rogers is a twenty-two-year old, walking, talking wet dream. With her long blonde hair, luscious lips, all cheerleader toned and muscled with what appear to be perfect, natural tits, and an ass you could bounce a quarter off of. The girl is Victoria’s Secret level gorgeous, a freakin’ knockout, a fifteen on a scale of one to ten, a cheerleader with a daddy complex, which means she’s energetic and eager to please.

  Very eager to please.

  And at that moment, the guy she wanted to please just happened to be me. Go figure.

  The first time we had sex it was with me standing behind the lectern at the front of the classroom and her on her knees in front of me. She hummed as she unzipped my Chinos and brought out my ten-inch cock, already rock hard and ready to pop. I had had sex with Haley in my dreams since the first day she sauntered into my classroom at the start of the semester. That day, she waited until everyone else left the classroom, then locked the door and walked toward me with her tongue circling her lips. When she bent over my desk to show me that she wasn’t wearing a bra, my cock popped to attention like a good soldier. Yes sir! Ready to serve sir!

  “Professor Moss,” she said, drawing out the words, cooing at me. “I was just wondering…”

  “Yes, Haley,” I said, swallowing the giant lump that lodged in my throat the moment she locked the door.

  “I was just wondering, could I get extra credit if I gave you the best blowjob of your life?”

  She batted her eyelashes and let her tongue go slowly around her lips again. She pooched her lips and narrowed her eyes. She was seductive in a clumsy, slutty, college girl, Judd Apatow movie, sort of way. I was sure her tactics worked well on football players and other boys who would have climbed a mountain of dead bodies just to sniff her panties. Hell, who am I kidding? It worked on me. My cock plumped against my leg in an instant, throbbing for release.

  I smiled up at her, not because she’d offered me the best blowjob of my life (that bar was set pretty high), but because Haley probably thought she was the first student to ever make me such an offer. And she probably thought that I’d be falling all over myself to let her wrap her wonderful lips around my cock and have her tongue playfully tease the head while I filled her mouth full of milky goo.

  Sadly, Haley had not learned the key to seducing a guy like me. You didn’t have to impress me with your slutty words or your seductive powers. You didn’t have to say outrageous things or flash me your tits. Those things were cool and the effort greatly appreciated, but if you wanted a guy like me to fuck you, all you had to say was, “Hey, Holden, let’s fuck!”

  The thing that Haley didn’t realize was that I was a good-looking guy surrounded by hot, horny girls on a daily basis, most of whom would fuck me silly just to be able to say that they had fucked a college professor once they were older and married and bored and looking for something to brag to their girlfriends about.

  “Oh sure, I fucked one of my college professors when I was twenty-two. Why? Didn’t you?”

  I had been teaching for ten years and having sex with students for most of that time. And back when I was a college student myself, I was having sex with hot female professors. When it came to my students, I never approached them about sex. That was my rule. I would not allow myself to ask for sex or suggest we “get together for a drink after class” or any of that bullshit, but if a hot twenty-something came on to me with no agenda other than having great sex for great sex sake, why would I decline?

  I had my morals and standards. I’d never exchange sex for grades no matter how hot the girl was, but if she was just horny and playing out some older man fantasy, why would I insult her by saying no?

  I wanted to tell Haley Roger that I had probably gotten more blowjobs than the average porn star. And I had certainly fucked more hot, young coeds than the average college football star. And now, since she had so kindly offered, I was going to get what Haley promised to be “the best blowjob of my life”. I doubted it would reach such lofty heights, but it would be a great way to cap off a Friday afternoon.

  “What did you have in mind?” I asked, watching as she straightened her back and stretched her arms toward the ceiling. When she did, the short skirt rode up enough to give me a nice glance of her shaved pussy and pink clit.

  “Well,” she said, moving toward the podium. “Why don’t you stand here and pretend like you’re giving a lecture to the class.” She glanced at the open space beneath the podium and smiled. “While I get in there and suck your cock until you cream on my face?”

  I had to smile. And I had to give it to her. She certainly was creative. I almost said, “If you really want a thrill you can suck my cock during a real class like your friend Ashley Ayers did last semester.”

  I almost said it, but I didn’t. What happened between me and my students was my secret. I knew that Ashley had probably said something to Haley because I saw them together on campus all the time. They belonged to a sorority that only admitted hot, bitchy girls like Haley and Ashley.

  The rumor was, the sorority sisters even held competitions to see who could fuck or suck the most football players at the start of every football season. Supposedly there was even a points system. Let’s see, it was… Hand job: 1 point... Blowjob: 5 points... Vaginal sex: 10 points... Anal sex: 15 points... Three-way: 20 points... Double p
enetration: 25 points.

  I wondered if there was a tally board with the names of professors like me that the sorority sisters had fucked or sucked. Then I wondered if my name was anywhere near the top.

  Girls talk. Especially those girls. Hell, that could be why Haley was coming onto me with the offer to blow me while I was standing at the podium. Girls talk amongst themselves, compare notes, share tips and tricks.

  Thankfully, none of the girls I had had sex with had ever ratted me out to the dean. They would never do that. Not the way I took care of their needs. That’s what made me different than the jocks and other professors these girls had sex with. I actually cared about their needs, more so than my own.

  That’s one thing about me that women have always loved. I’m a fucking alpha male with a big cock and an insatiable appetite when it comes to sex, but I also give more than I receive. It’s a personal satisfaction thing with me. I want to get my rocks off, but I got greater pleasure out of making the girl cum, over and over and over again.

  I wanted every woman I had sex with to walk away on wobbly legs going, “HOLY SHIT, THAT WAS FREAKIN’ AMAZING! I WANT TO DO THAT AGAIN!!”

  There is no greater complement in my mind than looking up with a girl’s juices covering my mouth and cheeks and seeing that “the dam just broke” glow on her face. Dreamy eyed, red cheeks, quivering lips, breasts heaving, trying to breathe. I loved watching a girl’s face as I hammered into her tight pussy while she exploded and writhed around like she was having a sexual seizure.