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  • A Little Bit Deeper Now Ch. 01

A Little Bit Deeper Now Ch. 01

12

Author's Note: I'm putting this one in Loving Wives, but be warned this story contains significant blackmail/NC/reluctance themes. I'm going for dark, direct, and dirty here, since I'm simultaneously writing a romantic series and enjoy the change of pace. This chapter is fairly short, but sets up a multi-part series. All characters are 18+, all rights reserved, etc. -Theworldspins

*****

The last thing Paul Whitman wanted to do was deal with some smart aleck brat on a Friday afternoon. While most of his students at Chatsworthy Prep were decent kids, if a little spoiled, he knew of a couple who ought to have their asses kicked. No school, no matter how wealthy and elite its students may be, was entirely free of 'problem cases'; in fact, those problems cases might be even worse with filthy rich parents and trust funds.

When Simon Chalfont walked into his office, however, Paul was surprised. It wasn't that Simon was a good kid—far from it. Rather, it was shock that the mastermind had finally been caught.

"Hello, Mr. Chalfont," Paul said in a patronizing tone. "Don't see you in here very often."

"It's a special day," Simon responded drily, brushing the shaggy black hair back from his eyes. "I allegedly cheated off Connor Halloran's exam."

Paul's first thought was "interesting choice." As little respect as he had for Simon, he was no dummy, and Connor was one of the dimmest bulbs at Chatsworthy. Something seemed odd, but Paul buried his suspicions. After all, he was just happy Simon had finally been caught in the act and might face some consequences to the cavalier way he treated the rules and the Headmaster's authority.

"I'm surprised this was how we finally caught you, Mr. Chalfont. I've had my eye on you for a while."

Simon seemed unimpressed.

"I thought I saw you checking me out, Dr. Whitman. I'm glad you were just spying on me and looking for a date."

The insolence of the kid was staggering.

"You know you can't talk like that in here. I can have you suspended for that disrespect alone," Paul said sternly.

With warning, Simon's eyes widened and his head shook a little. If Paul didn't know any better, he'd think the kid was contrite. There was something about the vacancy in his eyes, though, that kept Paul from falling for the boy's act.

"Oh no," he said facetiously, "I...I did something bad! What will Jesus say? When it rained last week...was that his tears?"

Despite the boy's mockery, Paul knew he had him dead to rights here, and inside he was relishing the prospect of punishing Simon. Paul knew that Simon was responsible for hiring the strippers who came to Mrs. Cleary's retirement party, though he hadn't a shred of proof. The school wasn't going to actually shell out for extensive DNA testing, but the 'unknown gooey residue' he found on the doorknob to the nurse's office last year was probably of Simon's own making. It was always petty, always boundary pushing—not quite truly damaging, but always calculated to embarrass, humiliate, and to test peoples' weaknesses.

Since his arrival, Simon had been a constant irritant: cruel, calculating, and two-faced. As Headmaster at Chatsworthy, Paul had spent four years watching over Simon, making sure he never got out of hand. Most of the time, he seemed like a completely normal kid; he'd even fooled Beverly, Simon's English teacher and Paul's wife of three years.

Every student at Chatsworthy was expected to participate in extra-curriculars, and Simon had admittedly compiled an amazing track record in competitive debate. Beverly Whitman was the team's coach, and despite her husband's warnings, she continually defended Simon from accusations whenever Paul would mention some horrible thing he believed Simon to have caused. In Beverly's eyes, Simon was a potential national champion and misunderstood genius.

"He's so persuasive," she would say. "He just casts a spell on the judges when he's up there. I've never seen anything like it."

With the boy sitting in his office, Paul couldn't see what was so special about him. He looked like any other Chatsworthy kid, albeit with a faintly malevolent smile. Well, that and his eyes: they were so...hollow. Simon always seemed to be looking right through people.

"Well, Mr. Chalfont, what have you gotten into today?"

Paul knew the answer; he just wanted this moment to linger. Simon leaned forward, ever so slightly. He was a little pale, with thick dark hair that hung almost to his eyes. Like the other boys, he was clad in the navy pants and crested blazer of a Chatsworthy student, though the collar of his white shirt betrayed a dark, long set-in rust-colored stain, the trace of a distant brawl freshman year that Simon had lost.

"Your wife's pussy."

Paul's first impulse, which he just barely restrained, was to slap the little brat right in the mouth. His words jumbled together in his mouth, as he tried to suppress anything that might get him canned immediately. He had to be better than some punk kid.

"No, I'm lying, Dr. Whitman," Simon continued, smirking a little. "I haven't fucked Mrs. Whitman since Tuesday. In fact, I've been saving up my load for today."

His anger in check, Paul leaned back. He even felt a little glee; he had this little bastard right where he wanted him. Cheating was bad, and made him subject to fail the class. Add to it the gross insubordination and inappropriate language, and Simon would finally get a big black mark on his transcript with a long suspension. Maybe his grades would slip enough as a result to see him forced to attend a slightly less prestigious university.

"Well, Mr. Chalfont, you've just bought yourself a suspension and a parent conf—"

"Fuck off, Dr. Whitman," Simon interrupted coldly. "My father isn't going to waste his time talking with somebody like you. I mean, honestly, do you not see where we are? You're not in control here."

Paul reached for his phone to call the school resource officer. It would serve the little shit right if he got frog-marched out of the office where everyone could see him. Maybe a little shame would keep him from pulling shit like this.

"If you don't want everyone knowing about Beverly's little butterfly, put that fucking phone down."

That got Paul's attention. His darling wife, in her college days, might have been a little...wild. All that remained from those days, though, were a few racy stories she'd shared with Paul to get his motor running and a small tattoo of a butterfly about an inch or so northwest of her pussy. He set the phone back down, unsure how Simon knew about that.

"Better," the smarmy kid said. "Now we can talk like men. Paul—can I call you Paul?"

Paul's mouth hung open, but no sounds escaped.

"I'll take that as a 'yes.' Paul, for three weeks now I've been fucking your wife. That's how I know about the butterfly. That's how I know how she squeals out 'Daddy' when she comes—which, by the way, is hilarious. Anyway, I'm trying—"

With a low rumble, a voice finally emerged from the pit of Paul's stomach. It was a simple, raspy, animalistic growl: "GET OUT!"

Simon merely smiled, though Dr. Whitman's face was bright red and he appeared to be trembling with a barely concealed rage.

"Can't do that. See, I'm not leaving here until someone sucks my cock."

Simon let his words hang there, without further explanation. When Paul reached once more for the phone to call security, Simon reached out and deftly pulled the cord from the back of the large black phone receiver.

"Paul, I've got more than just stories. I've got pictures. Videos. I could get my phone out and show—"

Without thinking, Paul grabbed Simon's hand, pulling him violently over the desk. Simon made not so much as the faintest cry of pain, even as Paul used his other hand to press him flat into the desk, hard. He was violently restraining a student, alone in his office, and it was going to get him fired if he didn't settle down.

"Good man," Simon said with a laugh, as if he were still in charge and not pinned to his headmaster's desk. "It'll be a shame, though, when everyone Googles your name and finds out you were the chump whose wife fucked a student. You'll be the Steve Letourneau of a new generation."

With that, Paul released Simon, who rubbed his sore arm. Paul's head was spinning. Could the bastard really tell everyone? Have everyone know about his wife? Simon's reptilian smile had not gone away.

"I won't hold that against you. I figured you wouldn't have any balls at all, I mean, losing your woman to an eighteen year old kid?" Simon said. "Hey, look, that's good news, right? At least your wife won't go to jail. I guess they'll fire her ass, though, put her on the news and shit. I mean, you can't fuck your students, even if they're legal age and all. And it will be pretty hard for you to stick around here, everyone laughing behind your back at how your whore wife loved to suck off students. And the pictures! I'd hate to be you in that situation, Dr. Whitman."

Paul was sweating now, lightheaded and nauseous. He was in a state of panic and felt the sudden, irrational urge to begin begging Simon not to tell anyone. Nothing about what he knew of Simon suggested that might work.

"I apologize for monologing, Dr. Whitman. Shit, I said I'd call you Paul. Paul, I apologize—not for fucking your wife, because, let's be honest here, she is one sweet piece of ass—but for not getting to the point. Sometimes I ramble...well, the point, Paul, is that I haven't blown my load in three days. You don't know how hard it is to hold out when you've got a hot little teacher who'd love to let you just shoot off inside her. Or, shit, maybe you do! We do have something in common, after all."

Paul was doing the math in his head. The bastard was right: if he went public, not only was his wife's career and life over, but also he would go down with her, even though he was totally innocent. He had too much pride to show his face at work after everyone had learned what a whore his wife had turned out to be.

"What do you want?" Paul asked defeated.

"Someone's gonna suck my dick. Now, it could be your wife. You could call her in here—she's on study period. You could lock that door and tell her to get on her knees and take my cock down her throat. Believe me, Paul, she's already come really close. I'm sure with a little encouragement, we could get that cute nose of hers buried in my pubes."

Despite himself, Paul's mind flashed to an image of his wife's mouth stretched around a huge cock. It wasn't the first time he'd wondered what she would look like with a strange dick in her mouth, though he'd never share that thought with anyone else, especially not her.

"But then she'd know you know," Simon continued. "It'd be real, for everyone. See, right now, it's just you and me. You can dump the bitch. You can go cheat on her yourself. Or, if you're a worthless piece of shit, you can just forgive her, sweep it under the rug, and just ignore the fact that another guy is gonna have your wife's pussy whenever he wants it."

Paul couldn't believe the audacity of this kid. A voice in the back of his head kept urging him to just leap across the desk and strangle the kid. If he was going to lose his job, might as well lose it for killing the shitty little brat and not just slink away out of embarrassment. A real man would go down swinging. On the other hand, Paul had to consider that the punk was bluffing. If he was ballsy enough to talk like this, maybe he was ballsy enough to fake it all.

"I don't believe you. I don't believe Beverly did anything with you, and now your ass is mine, you fucking punk—"

Paul was silenced by the image of his wife, riding another man, on Simon's phone. Though the man's face wasn't visible, it didn't much matter if it was Simon or someone else. She'd cheated. With a few swipes, Simon began playing a video of his wife's face, contorted into a mask of pleasure as someone plowed her from behind doggystyle.

"C'mon Paul, you didn't really think I was bluffing, did you? I think you just wanted to see what it looked like when your wife felt a real man's cock inside her. Now the ball's in your court. You call her in here and the game's on for real."

Paul was dumbstruck. He knew, for certain, that his wife had betrayed him. The image of her, propped onto her elbows, her long auburn bangs bouncing in front of her eyes as her mouth, transfixed in an 'O' shape, let loose a long moan of ecstasy.

He'd always felt lucky to have a woman like Beverly: she was curvy in all the right places, and at 5'3" she was a petite, sexy package. Her full tits and yoga-sculpted legs always got him hard immediately. If anything, she was too hot: just staring into her piercing green eyes and touching her smooth bare skin when they made love would send him prematurely over the edge.

"Paul, still there?"

He took a deep breath.

"So what's my other option?"

"Suck it yourself."

Paul felt a wave of revulsion. He would never bring himself to do something like that again.

"I'm not gay."

Simon smiled inappropriately, as if he was trying to look...nice.

"Well, neither am I. Although I guess if you did start sucking my cock, then you might be a little gay. Not full-on Elton John, maybe, but more...I don't know, Anderson Cooper? That guy had people thinking he was straight for a few years before he finally came out."

Paul was straight—it didn't matter what happened that night in college. Simon wasn't going to break him down so easily.

"I'm not gonna...no way."

"Just think for a second, though. If you call her in here, your marriage is never going to be the same. Plus, you know I've got the goods on your wife. She's mine already. Don't you want to just suck a little cock and get this whole thing over with? I picked you and your wife because I saw something in you, Paul."

"Fuck you, you...you little faggot."

Paul hadn't used such homophobic language for years. Chatsworthy was a socially tolerant, forward-thinking school: that kind of thing had been purged from his vocabulary.

Simon frowned.

"I want you to remember calling me that."

Paul and Simon descended into a silent, uneasy stand-off. School would be out in another twenty minutes.

"Dr. Whitman, your phone is disc—"

"I know Margie," he called to his septuagenarian secretary through the door. "I'm working on something, and I can't be disturbed."

"Alright, Dr. Whitman, I'll tell Mr. Evans to call you tomorrow."

A minute ticked by in utter silence. Though Paul felt physically ill now, Simon seemed unfazed, as if he could sit in silence for hours without the slightest feeling of anxiety or discomfort creeping in.

With a moment of silence to process his thoughts, Paul now turned his anger on his wife Beverly. She was to blame for this mess—fucking a student! In his mind, he called her every nasty name he could. He'd known about her wild past when he married her, though at only twenty-six, the past wasn't so long ago for her. He had hoped a hot, slightly slutty young wife would be just the thing to reinvigorate his sex life once he turned forty. Now he was staring the prospect of becoming a cuckold and getting a divorce in the face.

Finally, Paul plugged the cord back into the phone. Simon watched intently, allowing him to pick up the receiver. There was still time to call security, to have Simon escorted from the premises and throw his cheating wife out on her ass. People would talk, laugh behind his back, but he could hold his head up high...

"Mrs. Whitman, please report to the Headmaster's office."

Simon smiled. A few minutes passed by before he spoke again.

"Good choice, Paul."

"Don't talk to me."

"Your wife probably sucks cock better than you do anyway."

"Shut. Up."

"You won't regret this. I bet a guy like you might even chub up seeing his wife slobbing knob."

"You're dead."

"Somehow I doubt that—oh, Beverly, hi!"

When Beverly Whitman opened the door, she could tell from her husband's face and Simon's juvenile, leering grin that something terribly wrong was happening in the office.

"You...ummm...wanted to see me?" she asked tentatively.

Paul looked at Simon, and Simon looked at Paul. Beverly wondered what the hell was going on.

"Ask her," Simon commanded of Paul.

"Ask me what?" she asked, her voice taking on an indignant tone she hoped hid the note of guilt.

Her secret teenage lover and her husband (and boss) were sitting across from one another, and she had been called in out of the blue. She could only cling to the hope that this was some bizarre coincidence: after all, she was Simon's teacher.

Paul's stare was pure hatred. She didn't get to harbor her illusions for long.

"Did you fuck this kid?"

Beverly started to breathe shallow. It wasn't supposed to happen like this. It was supposed to be a secret, until Simon went to college, and he would take her with him. She felt her world crumbling around her. Paul knew.

"Answer me!"

"That's not what you were supposed to—" Simon explained.

"Answer me!"

"No!" she cried out. "I mean, it wasn't like that. I thought...Simon?"

He took hold of her hand, and though she flinched, her mind was so scattered that she didn't fully pull away. Paul watched the display of intimacy with humiliated rage.

"Oh, you thought we were, like, boyfriend and girlfriend? Did you think we had a special connection? Were we going to start running and meet in the middle of a field or something?"

He kissed the top of her hand chivalrously. She trembled with fear, though it looked like desire to her enraged husband.

"No, sweetie, actually you were—are—a piece of ass. That's all. I'm fucking you and now I'm fucking with your dumb ass husband, because it's funny and because I'm bored and because this is what I do."

Simon turned back to Paul then waited for a moment in silence.

"That wasn't the question, Paul. Ask her."

Paul wavered for a moment.

"You do it."

Simon shook his head. He was tired of talking.

Beverly and Paul's eyes met. She was sobbing softly, and for the faintest moment, he felt a pang of pity for her, before a wave of fury crashed over his heart, washing away all sympathy within.

"Your boyfriend is going to blackmail us with the sex tapes he made with you. Now he wants a blowjob from you here in the office."

Beverly was stunned. Until this day, Simon had been one of the most unique, charismatic, and sensitive student she had ever met. The first day he entered her classroom, he had stood out above all other students—Beverly had a Master's Degree, and half of her classmates in graduate school hadn't been as smart as he was. In her hearts of hearts, she knew she'd fallen for him immediately. He was everything she had been looking for in Paul, only without the flabby, old body and the stale complacency of middle age. It had been difficult to wait for Simon's eighteenth birthday to be with him, but she felt like it was important. She wanted everything with Simon to be perfect.

She froze for a moment, before looking down. Simon had already pulled out his cock and started stroking it lightly. Though they'd only begun their affair three weeks ago, already Simon's dick had brought her more pleasure than three years of her husband's had. Paul invariably had to finish her with his hand for her to be able to come.

"She's really good," Simon said to Paul, as if she wasn't there. "It helps to practice on a small one first, I guess."

"I'm not small," Paul seethed. "My cock is as big as yours."

"Well take it out and jerk off while your wife blows me then. Could be fun."

That shut Paul up for a moment. As for Beverly, she had yet to adjust to the horror show her life had just become.

"I'm not going to sit here with my dick in my hand all day, sweetie. Get down on the floor and do what you were put on this earth to do," Simon said, the hatefulness of his words disguised by the placid, even tones of his voice.

12
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