Blackmailing My Hunky Tutor – Page 1

A closeted 18yo prepping for his first semester at university decides to make his tutoring session A LOT more interesting when he discovers some embarrassing information about his hunky straight 23yo tutor.

Blackmailing-hunky-tutorBlackmailing My Hunky Tutor – Page 1
by Leo1202
Art by Sherwin-prague. More of his work at his Deviant Art page.

I’ve just finished another lesson with my private tutor.  As he leaves my house I close the door behind him and sigh with longing.  My name’s Chris and I’m 18 years old.  I’ve recently finished high school and before starting university (in which I’ve already earned my place) my family insisted that I take extra lessons to make sure that I don’t get rusty in the few months leading up to the start of the semester.

Like my older brother, I’m going to study mathematics, a tricky subject, but one I’ve always been good at.  I said my brother should just give me lessons, since I didn’t even want them and knew he’d let me slack off, but my mom saw through that plan and wanted someone who would take it seriously.  I’ve never been so glad about anything in my life.

Jack, my tutor, is a friend of my brother’s from their time at university.  My brother went into accounting but Jack, now 23, has spent the last year working as a private tutor for a prestigious tutoring company, with the hopes of one day going independent as there’s a lot of money to be made from it, and he seems to have a real passion for it.

I don’t care much about Jack’s passion for tutoring, I care about Jack’s stunning good-looks.  He’s tall, I’d guess 6 feet or just slightly taller, with broad shoulders that taper into a trim body, a narrow waist and sexy legs.  He and my brother are gym buddies, too, so I know he works out a lot and I’d give anything to see what was under the cute shirt and sweater combos he usually wears.  He has neatly styled dark-brown hair that’s shaved at the sides into a modern cut, and slightly tanned skin. He’s got a strong, chiselled jaw, his eyes are a shade of brown/green that change colour in the light, and when he smiles I can’t help but stare.

As you can guess, I’m gay, but my family don’t know that.  Unfortunately, Jack is about as straight as they come, and he’s had a girlfriend for the last 3 years.  He’s not a typical straight jock though, which I think is yet another reason for my obsession with him.  He’s kind and considerate and seems to be just an all-round nice guy!

As I watch him pull away in his car in the window I know I must have him.  I absolutely must.  I’ve been with other guys before but none have ever got me as turned as Jack does just by being near him.  The problem is that if I was to ever approach him and tell him how I feel I know he’d react badly, and he’d definitely stop coming to our house to tutor me.  In any case, I wasn’t going to confess my love for him, I just wanted to see him naked!  I realised I was going to need to go about this another way.

*  *  *

The means for this to happen presented itself 3 weeks ago when my brother left his phone unattended.  He received a text from Jack.  It simply said “I should never have done that, it could have got me fired”.  Intrigued, I scrolled up through the rest of the conversation, eager to see what this perfect man could have possibly ever have done wrong.  As I read further, I realised that Jack had been taking extra money from one of the kid’s families he taught in the form of cash.  Apparently, he’d told them the fee had temporarily gone up but that there was no need to change their standing order, and that he could simply take the extra money in cash.  He admitted to my brother that this was because of a rough patch and he didn’t have enough to cover rent for last month, and once he was back on track he’d told the family the fee had gone back to normal.  However, what he’d done was certainly against his company’s policy of taking cash payments, not to mention he’d lied to a trusted client.  I screenshotted the messages and sent them to my own phone, for future use.

It wasn’t until now, 3 weeks later, that I’d be able to use them to my advantage.  My family were planning a trip to Switzerland for a long weekend and asked me if I’d like to join, but I declined saying that with university starting so soon, I’d rather stay and prepare with Jack, if that was ok with them.  Of course, my parents were overjoyed at this and praised my maturity and dedication to my studies.  I smiled and thanked them, all the while hatching my plan for when Jack came round for our Friday night lesson.

He arrives at 7 sharp as always, pulling up into our driveway and ringing the doorbell.  I wait a minute before answering so that he doesn’t know I was watching him walk up the driveway from the upstairs window, then open the door.  He’s wearing a dark red sweater and a clean white shirt underneath, and perfectly fitting slim, dark blue jeans and brown leather Chelsea boots.  Even though he dresses like a teacher, he still manages to look incredibly sexy and fashionable.

“Hey Jack, come in,” I say cheerfully.

“Hey Chris, how are you doing?” he says.  “Enjoying having the place all to yourself?” he says with a cheeky grin, as though he knows what I’ve been doing.  It makes my stomach flip.

“Oh yeah it’s great, I say, just been studying and stuff, the usual.”

“That’s what I like to hear,” he says with a laugh.  “Shall we get started?”

Oh yes we shall, I think to myself.

We head to the dining room, where we always do our lessons.  Jack sets up his usual board on a stand at the end of the table that he uses to write on, and starts to gather his notes.

I sit at the other end of the table, bracing myself.

“So I was thinking we could pick up with algebra again this week,” Jack begins.

“Actually,” I say, “I think I’d rather do a pop quiz.”  Jack often does these quizzes with me to test that I’ve remembered what he’s taught me.

“Haha nice try”, he says.  “I’ll maybe quiz you at the end”.

“I was thinking I might quiz you for a change”, I say innocently.

Jack has been shuffling paper around whilst we talk but he stops and looks up at me when I say this.

“Um I don’t think so dude, I’m the one doing the teaching, remember?” he says, half-jokingly.

“Oh I know that,” I say, “but I think this is gonna be a quiz you’ll wanna take, since your job is at stake if you don’t”.

He looks completely startled at this.

As if by explanation, I slide a couple of sheets of paper down the table at him.  I’ve printed off the texts between him and my brother and as I watch his eyes scanning the paper, a look of terror dawns on his face.

“Chris,” he starts “this…”

“I know what it is Jack, and I know you’ll get into a lot of trouble if your company were to find out what you did”, I tell him causally.

“Listen Chris, I felt terrible about doing this, but I’m gonna discount a few of that family’s lessons now so it’ll be like they were never charged extra,” he explains.  I can tell he is sincere about feeling bad for what he did.

“Uh huh”, I reply.

“I’ve never done that to your family Chris and I’ll never do it again, so don’t worry,” he says as if the discussion is over.

“Oh I know, Jack.  Because you’re going to have to convince me not to tell my mom and your company what you did,” I begin.

He looks confused.

“Listen Chris, you know how bad I feel about this, please, if you tell my bosses I’ll lose my job and maybe never tutor again, and I love to teach,” he says compassionately.

“Be that as it may, you’re gonna have to do something for me, Jack,” I say.  “To ensure my silence.”

“Ok, you can have the rest of the lessons before you start university for free, and I’ll tell your mom that you’re doing amazing work, sound good?” he asks.

“No, Jack.  I’ve told you already what I want, and that’s to play a quiz”, I tell him.

“Um ok”, Jack says, “but what do you wanna quiz me about?”

“Well, maths, obviously”, I say cheerfully.  “You’re always quizzing me with really hard questions, so I wanna give you some hard questions for a change”, I tell him.

I see him visibly relax as he sees that all I want to do is have some light revenge for all the hard questions he’s thrown at me over the past few months.  Only that’s not all I want.

“That seems fair,” Jack says.

“Oh, I’m not finished,” I tell him.  “You see, I’m going to ask you 10 questions, and for every question you get wrong, you’re going to take off a piece of clothing”, I say calmly.

Jack’s eyes widen in shock at this and I smile.

“Wha…” he begins to ask but I cut him off.

“Listen Jack, I find you incredibly sexy, I have from the moment you started tutoring me, and this is the price you’re going to pay for my silence.”

He has visibly paled at my words.

“You can’t be serious,” he says, the horror clear in his expression.

“Oh, I am”, I tell him defiantly.

“But, Chris, I’m not gay.  I’m not taking off my clothes in front of you, I have a girlfriend.  And I’m your tutor!  Come on man, let’s work something out”, he tries to reason.

I almost feel sorry for the handsome boy, who looks like a deer in headlights.  He genuinely is a nice guy who means well, but I’ve waited too long for this, and I’m not taking no for an answer.

“Listen Jack, you never know, you might get them all right and not lose any clothing, then you can go on your way.  But if you’re not game and you want me to send these texts to your boss right now then I will”, I say stubbornly.

He hesitates so I pick up my phone.

“Wait!  Wait. I- I’ll play”, he says, hanging his head in shame.  “I’ll play your quiz, just please don’t send those texts”.

“Excellent.  Let’s begin” I say enthusiastically.

I’ve just finished another lesson with my private tutor.  As he leaves my house I close the door behind him and sigh with longing.  My name’s Chris and I’m 18 years old.  I’ve recently finished high school and before starting university (in which I’ve already earned my place) my family insisted that I take extra lessons to make sure that I don’t get rusty in the few months leading up to the start of the semester.

Like my older brother, I’m going to study mathematics, a tricky subject, but one I’ve always been good at.  I said my brother should just give me lessons, since I didn’t even want them and knew he’d let me slack off, but my mom saw through that plan and wanted someone who would take it seriously.  I’ve never been so glad about anything in my life.

Jack, my tutor, is a friend of my brother’s from their time at university.  My brother went into accounting but Jack, now 23, has spent the last year working as a private tutor for a prestigious tutoring company, with the hopes of one day going independent as there’s a lot of money to be made from it, and he seems to have a real passion for it.

I don’t care much about Jack’s passion for tutoring, I care about Jack’s stunning good-looks.  He’s tall, I’d guess 6 feet or just slightly taller, with broad shoulders that taper into a trim body, a narrow waist and sexy legs.  He and my brother are gym buddies, too, so I know he works out a lot and I’d give anything to see what was under the cute shirt and sweater combos he usually wears.  He has neatly styled dark-brown hair that’s shaved at the sides into a modern cut, and slightly tanned skin. He’s got a strong, chiselled jaw, his eyes are a shade of brown/green that change colour in the light, and when he smiles I can’t help but stare.

As you can guess, I’m gay, but my family don’t know that.  Unfortunately, Jack is about as straight as they come, and he’s had a girlfriend for the last 3 years.  He’s not a typical straight jock though, which I think is yet another reason for my obsession with him.  He’s kind and considerate and seems to be just an all-round nice guy!

As I watch him pull away in his car in the window I know I must have him.  I absolutely must.  I’ve been with other guys before but none have ever got me as turned as Jack does just by being near him.  The problem is that if I was to ever approach him and tell him how I feel I know he’d react badly, and he’d definitely stop coming to our house to tutor me.  In any case, I wasn’t going to confess my love for him, I just wanted to see him naked!  I realised I was going to need to go about this another way.

*  *  *

The means for this to happen presented itself 3 ago when my brother left his phone unattended.  He received a text from Jack.  It simply said “I should never have done that, it could have got me fired”.  Intrigued, I scrolled up through the rest of the conversation, eager to see what this perfect man could have possibly ever have done wrong.  As I read further, I realised that Jack had been taking extra money from one of the kid’s families he taught in the form of cash.  Apparently, he’d told them the fee had temporarily gone up but that there was no need to change their standing order, and that he could simply take the extra money in cash.  He admitted to my brother that this was because of a rough patch and he didn’t have enough to cover rent for last month, and once he was back on track he’d told the family the fee had gone back to normal.  However, what he’d done was certainly against his company’s policy of taking cash payments, not to mention he’d lied to a trusted client.  I screenshotted the messages and sent them to my own phone, for future use.

It wasn’t until now, 3 weeks later, that I’d be able to use them to my advantage.  My family were planning a trip to Switzerland for a long weekend and asked me if I’d like to join, but I declined saying that with university starting so soon, I’d rather stay and prepare with Jack, if that was ok with them.  Of course, my parents were overjoyed at this and praised my maturity and dedication to my studies.  I smiled and thanked them, all the while hatching my plan for when Jack came round for our Friday night lesson.

He arrives at 7 sharp as always, pulling up into our driveway and ringing the doorbell.  I wait a minute before answering so that he doesn’t know I was watching him walk up the driveway from the upstairs window, then open the door.  He’s wearing a dark red sweater and a clean white shirt underneath, and perfectly fitting slim, dark blue jeans and brown leather Chelsea boots.  Even though he dresses like a teacher, he still manages to look incredibly sexy and fashionable.

“Hey Jack, come in,” I say cheerfully.

“Hey Chris, how are you doing?” he says.  “Enjoying having the place all to yourself?” he says with a cheeky grin, as though he knows what I’ve been doing.  It makes my stomach flip.

“Oh yeah it’s great, I say, just been studying and stuff, the usual.”

“That’s what I like to hear,” he says with a laugh.  “Shall we get started?”

Oh yes we shall, I think to myself.

We head to the dining room, where we always do our lessons.  Jack sets up his usual board on a stand at the end of the table that he uses to write on, and starts to gather his notes.

I sit at the other end of the table, bracing myself.

“So I was thinking we could pick up with algebra again this week,” Jack begins.

“Actually,” I say, “I think I’d rather do a pop quiz.”  Jack often does these quizzes with me to test that I’ve remembered what he’s taught me.

“Haha nice try”, he says.  “I’ll maybe quiz you at the end”.

“I was thinking I might quiz you for a change”, I say innocently.

Jack has been shuffling paper around whilst we talk but he stops and looks up at me when I say this.

“Um I don’t think so dude, I’m the one doing the teaching, remember?” he says, half-jokingly.

“Oh I know that,” I say, “but I think this is gonna be a quiz you’ll wanna take, since your job is at stake if you don’t”.

He looks completely startled at this.

As if by explanation, I slide a couple of sheets of paper down the table at him.  I’ve printed off the texts between him and my brother and as I watch his eyes scanning the paper, a look of terror dawns on his face.

“Chris,” he starts “this…”

“I know what it is Jack, and I know you’ll get into a lot of trouble if your company were to find out what you did”, I tell him causally.

“Listen Chris, I felt terrible about doing this, but I’m gonna discount a few of that family’s lessons now so it’ll be like they were never charged extra,” he explains.  I can tell he is sincere about feeling bad for what he did.

“Uh huh”, I reply.

“I’ve never done that to your family Chris and I’ll never do it again, so don’t worry,” he says as if the discussion is over.

“Oh I know, Jack.  Because you’re going to have to convince me not to tell my mom and your company what you did,” I begin.

He looks confused.

“Listen Chris, you know how bad I feel about this, please, if you tell my bosses I’ll lose my job and maybe never tutor again, and I love to teach,” he says compassionately.

“Be that as it may, you’re gonna have to do something for me, Jack,” I say.  “To ensure my silence.”

“Ok, you can have the rest of the lessons before you start university for free, and I’ll tell your mom that you’re doing amazing work, sound good?” he asks.

“No, Jack.  I’ve told you already what I want, and that’s to play a quiz”, I tell him.

“Um ok”, Jack says, “but what do you wanna quiz me about?”

“Well, maths, obviously”, I say cheerfully.  “You’re always quizzing me with really hard questions, so I wanna give you some hard questions for a change”, I tell him.

I see him visibly relax as he sees that all I want to do is have some light revenge for all the hard questions he’s thrown at me over the past few months.  Only that’s not all I want.

“That seems fair,” Jack says.

“Oh, I’m not finished,” I tell him.  “You see, I’m going to ask you 10 questions, and for every question you get wrong, you’re going to take off a piece of clothing”, I say calmly.

Jack’s eyes widen in shock at this and I smile.

“Wha…” he begins to ask but I cut him off.

“Listen Jack, I find you incredibly sexy, I have from the moment you started tutoring me, and this is the price you’re going to pay for my silence.”

He has visibly paled at my words.

“You can’t be serious,” he says, the horror clear in his expression.

“Oh, I am”, I tell him defiantly.

“But, Chris, I’m not gay.  I’m not taking off my clothes in front of you, I have a girlfriend.  And I’m your tutor!  Come on man, let’s work something out”, he tries to reason.

I almost feel sorry for the handsome boy, who looks like a deer in headlights.  He genuinely is a nice guy who means well, but I’ve waited too long for this, and I’m not taking no for an answer.

“Listen Jack, you never know, you might get them all right and not lose any clothing, then you can go on your way.  But if you’re not game and you want me to send these texts to your boss right now then I will”, I say stubbornly.

He hesitates so I pick up my phone.

“Wait!  Wait. I- I’ll play”, he says, hanging his head in shame.  “I’ll play your quiz, just please don’t send those texts”.

“Excellent.  Let’s begin” I say enthusiastically.

With no other choice, Jack just stands at the top of the table, looking nervously at me.

“Question 1: If X2 = 361, what number is x?” I ask.

Jack just looks at me.

“Chris, you’d need a calculator to do that.”

“Nope, no cheating”, I tell him.

“Can I least write it down?” he asks, looking at his board?

“No”, I tell him. “You never let me write it down.”

“But I don’t make yours so hard!” he argues.

“Listen, you know the rules. Since I’m feeling generous, I’ll let you decide which items of clothing you’ll be taking off each time,” I say. “If you don’t know the answer, lose something”, I say nodding to his body. After more hesitation from him I reach for my phone.

With a sigh, he grabs the bottom of his sweater and pulls it over his head, placing it over the nearest chair. This reveals his crisp white shirt, tucked into his trousers. The shirt is tight fitting, highlighting his muscles underneath. He looks incredibly nervous. I smile.

“Chris, this is ridic…” he begins, but I cut him off.

“Question 2: 87,000 divided by 17.” Eager to stay clothed, he attempts a guess at this one.

“5,110?” He says after a while.

“Nope, rounded up it’s 5,118, sorry”. There’s no sympathy in my voice. I simply clasp my hands and wait patiently.

Jack looks at me a second longer, then reaches down, grabs his right shoe, and slips it off, putting it under the chair his sweater is on.

“Ah ah, Jack, nice try. Shoes and socks count as one item each”, I tell him.

He glares at me, but after a moment he reaches down and slips of his left shoe, putting it next to the other.

“Question 3: what’s 390,625 squared?” I ask.

Keen not to lose anything else, Jack makes another guess.

He thinks for a while.

“Uh, 140 million and, um…” he begins

“Wrong!” I say triumphantly. He glares at me again, but this time doesn’t wait as long before reaching down and taking off his socks, revealing his gloriously large, masculine feet. He looks visibly uncomfortable at my staring.

“What size are those bad boys, Jack?” I ask mischievously.

“12”, he grumbles.

“Excellent”, I say, smiling, increasing his discomfort.

After a while more staring, I continue.

“Question 4: what’s the square root of 7,921” I ask.

After about a minute his face lights up.

“89”, he says, somewhat triumphantly.

“Correct”, I tell him.

I have never seen someone look so relieved before. He believes, just for a second, that he can win this. Of course, I added a few in that I knew he’d get to give him this confidence boost, only to make it more satisfying when he ultimately fails.

“Question 5: 6754 divided by 27”, I say.

Of course, he’ll never get it but knowing that the next piece of clothing he’ll lose will reveal some flesh, he gives it a go.

“235?” he guesses.

“Not nearly close enough Jack,” I say.

He looks down at himself and looks at me.

“Please, Chris, you’ve had your fun, I’ve been punished for what I’ve done. Can we please stop this?” Jack tries to reason.

In answer, I pick up my phone and start typing this time. I’ve had enough of his non-compliance.

“OK, OK!” he half shouts.

I place my phone back on the table and look at him.

“Choose carefully now, Jack”, I taunt.

After another moment’s thought, he begins to unbutton his shirt. He’s realised that taking off his trousers will reveal his most intimate item of clothing to me, and he wants to avoid that at all costs.

I watch gleefully as he unbuttons each button slowly, nervously, not knowing that he’s actually putting on more of a show for me than if he was to just rip it off.

Eventually he gets to the bottom, pulls it out from his tucked trousers, and unbuttons the last one. I can already see his perfect 6-pack abs showing, and soon after he gives me what I want, taking each arm out, removing it completely and placing it over the chair with his discarded sweater.

I almost gasp at his perfect chest. His pecs are strong and dusted with the faintest coating of light brown hair. His abs, chiselled and stunning, are gloriously smooth until his belly button, where a similar, very faint area of light brown hair leads downwards in a trail to the waistband of his trousers.

I stare at this sight much longer than I did his feet, enjoying his embarrassment all the while.

He shuffles nervously from foot to foot, dreading my next move.

“Question 6: 223 squared”.

Again he thinks, and I see his eyes light up once more.

“49, 729” he recites carefully.

“Correct”, I tell him.

I can see his brain calculating the odds of him surviving another 3 questions. He won’t, if I can help it.

“Question 7, nearly done Jack. 1118 multiplied by 730”.

Knowing what’s next for him, but not knowing the answer, he begins just saying numbers, trying to delay, but I cut him off.

“Jack, you know that’s wrong”, I say bluntly, and nod towards his jeans, indicating what he should do.

I don’t need to pick up my phone, because Jack now knows it’s futile to try my patience.

Even more hesitantly than he began unbuttoning is shirt, he reaches for the button of his fly, undoes it, and slowly draws down the zipper, looking down all the while and avoiding my stare.

He puts his hands in the waistband at either side, and stops to look at me, as though I’m going to reveal now that the whole thing was a silly prank and he fell for it. Only I don’t, I meet his gaze expectantly and say nothing.

This goes on for a couple of seconds before Jack accepts his fate, and slowly pulls downwards, taking his jeans with him. I see a white Calvin Klein waistband first, and then, as the jeans reach his thighs, I see his dark red underwear.

He continues, slowly pulling downwards until they’re at his ankles, at which point he steps out, and kicks them under the chair next to his shoes.

What I’m looking at takes my breath away. My gorgeously handsome maths tutor is now standing sheepishly before me, clad only in his tight red Calvin Klein trunks. They only go to the top of his thighs, and sit perfectly on his small waist, hugging his legs and ass. His sexy treasure trail looks even more enticing disappearing into the white waistband of his boxers and his long, muscular legs are covered with a magnificent dusting of light brown hair.

The part that I simply can’t take my eyes off, however, is the huge bulge in the front of his dark red trunks. It really is large, and I can see a long, thick-looking outline curving downwards towards his legs.

“Oh fuck, Jack”, I can’t help but let out.

He blushes deeply at this, both on account of his humiliation and the clear line of sight that my eyes are focused on.

He moves his hands in front of his crotch, no longer able to bear my scrutinising gaze on his most intimate area, and it breaks my reverie.

I meet his eyes.

“Chris, you’ve got what you wanted”, he begins. “I’m humiliated ok, and I’ve paid for what I’ve done. I realise I might go a little hard on you sometimes, and I’m sorry, but you’ve had your fun and you need to stop this, please.”

“No Jack”, I say calmly. “My fun is just beginning.”

He swallows hard at this.

“But,” I say. “I am not unmerciful, and your last speech moved me. I’m willing to give you a chance to preserve your dignity.” At this comment, he unintentionally glances down at his half-naked form.

“You have 2 questions left. Given your track record, 2 out of 7, it’s not looking great for you”, I say. He listens intently. “I’ll allow you to forgo the next 2 questions, if you can recite Pi to 15 decimal places.”
His eyes widen, but he continues listening.

“This is a generous all or nothing offer. If you do it, you can get dressed and go. If not, the price is the same as before. You lose the boxers”, I say, looking down at them. Again he moves to cover himself.

“Or you could just attempt the next 2 questions and hope for the best?” I offer.

Jack weighs his options for a few seconds but he knows I have him. If my next 2 questions are anything like the last he knows he’ll be letting that big bulge out for me in no time.

He sighs and looks completely resigned. “Ok, Chris, I’ll try and recite Pi”, he says, defeated.

“Excellent. Begin”, I say.

CONTINUE THE STORY:
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2 Comments

  1. Avatar of Amalaric

    Amalaric - September 30, 2017, 3:07 am

    Well, fark me!!! This story is HOT in every way- pushes so many buttons I lost count; woof factor-10! Now, onward…

  2. Avatar of scotts60143

    scotts60143 - October 3, 2017, 6:26 pm

    Great beginning, and very well written! Really enjoyed the “strip” questions…thought that was very creative! Looking forward to the next chapter for more details!

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