A Guessing Game by Jack

A Guessing Game

Jack's world was black.  A deep, deafening blackness that consumed him entirely - leaving him completely vulnerable.  Not the familiar greyness of a blindfold, where faint shafts of light always seemed to find a way to  sneak around the edges and relieve his deprivation, even if only for a second.  No.  This was a blackness like no other he’d ever experienced.  A blackness so dark it made him truly consider if light had ever existed at all, or if it had just been a fragment of a dream he’d had once?

That would be the black-out contacts Lady Peregrine had told him to put in of course.  Thin films of pure sensory deprivation sitting over his eyes and denying him the fundamental right of light.

Jacks head turned suddenly, hearing movement to his left.  He recognised it instantly, the light footsteps of bare feet.  No.  The light footsteps of two sets of bare feet.  It was amazing how much more detail one could attain from other senses when one was taken away.

“Hello Jack,” said a sweet high voice to his left.  A soft voice, gentle even, but laced with strands of cruel intent.  He could almost hear the malicious smile playing at the corner of those soft lips.

“Hello Lady Peregrine,” replied Jack softly.  His heart had started to quicken, a reaction to her voice he’d never been able to master.  At the same time he started to grow; his cock instantly thickening and lengthening despite a complete lack of contact.  His body had a life of its own around her.

Lady Peregrine gazed down at her latest boy and smiled to herself.  He really had been quite the surprise!  So unpromising at first, full of arrogance and false pretences.  So close to being discarded.  And yet something had caught her eye.  Something had piqued her interest.  And after slowly stripping back his layers like peeling an onion, she’d finally came to find a person she actually liked.  No.  Not even liked.  Adored!  It had been far from an easy journey though - Let's just hope he was worth the effort!  He’d certainly proved entertaining so far, but this would be his biggest test to date. 

Jack was bound, naked of course, to a simple wooden chair she’d placed in the middle of the room.  His arms were secured tightly behind his back and his legs spread and bound to the legs of the chair.  Exposing him completely and leaving him vulnerable to her every whim.  And her whims were not always gentle.  She admired the rope work for a quick moment, it really was very good!  Glancing down at Cam by her side she smiled fondly.

“Excellent work on the rope Cam,” she praised, letting a hand find Cam’s hair and lazily running through it.  “Have you been practicing by yourself puppy?”

“Yes Mistress,” replied Cam gently, trying not to let the pride of her praise show too much.

Lady Peregrine smiled one last time down at her love before turning back to Jack.  Her eyes narrowed slightly, twinkling suddenly with malevolent intent.  This was going to be fun!  She started walking around him slowly, admiring her newest boy from every angle as she gently tapped the toy in her hand against her thigh.  She knew the sound of every step would ratchet the tension and anticipation building up in poor little Jack until he was approaching breaking point.  And she hadn’t even touched him yet!  After a full circuit of detailed and slow inspection she stopped directly in from of him and leant forward slowly until her face was right next to his.  Her hand found one cheek as her lips found the other, planting a slow soft kiss at the top of his jaw line.  Jack sighed deeply, nerves momentarily washed away.  And as he sighed he felt her pull back and then drag something soft and slightly damp across his chest twice.  It all happened so fast he could barely register what had happened before he heard her speak again.

“So.  Petunia,” she started, a gentle giggle at her pet name for him doing nothing to hide her excitement.  “You and I are going to play a little game.  It’s a simple game really.  Very simple in fact!  I have written a number on your chest.  And because I’m kind I’m going to tell you that number is something between one and a hundred.  Now all you have to do is guess it!  Simple yes?”

Jack knew this would be far from simple.  The iron malice in her voice was evidence enough of that.  But he knew what was expected by now.  And even if he didn’t the pure excitement racing through him would have directed him down the correct path anyway.

“Yes Miss”

Lady Peregrine grinned wickedly. 

“And if YOU hadn’t begged me to try out these contacts Jack, you could just look down and tell me!  But alas… You were so keen to try them weren’t you?”

“Yes Miss,” repeated Jack sighing inside.  Miss had a way of turning things he’d asked for against him.  Those thoughts however were suddenly interrupted by the introduction of a new noise.  A soft, crackling noise that hummed right next to his ear.

“Oh, and a few extra rules Jack,” continued Lady Peregrine, her voice dropping soft and dangerous.  “For every guess you get wrong, I’m going to shock you somewhere.  Somewhere different each time.  Somewhere… Fun!  And it’s going to hurt!   I’m not going to pretend to you that it isn’t…”

Jacks heart thundered in his chest, a cold nervous sweat breaking out on his chest as he clenched and unclenched his fists in anticipation of the pain about to come.  “Yes Miss” he managed to get out.  But barely.

“One final thing Jack…” continued Lady Peregrine.  “I know you boys think you’re clever.  And I’m sure clever little you will be thinking the longer you take between each guess means the longer you get to recover.  Yes?  Well no Dear.   Cam is about to wrap his lips around that gorgeous cock of yours and start sucking.  He’ll only stop between the time you make a guess and the time I either tell you it’s correct or shock you.  EVERY other second his mouth will be bobbing up and down on that beautiful cock of yours.  And I promise  you Jack you do NOT want to cum without permission, which you most certainly do NOT have!  If you cum before you find the right number, the pain you’ll feel will be ten times worse and ten times more prolonged than what is about to happen!  Understand Duckie?”

Dread filled every single molecule of Jack’s being. 

“Yes Miss” he whispered. 

“Good!  Cam, begin”

Jack felt a set of warm lips wrap around the tip of his cock, but before they could sink down he made his first guess, keen not to let Cam get him anywhere near the edge before he guessed correctly.

“Seventeen please Miss!”

The lips quickly withdrew, leaving Jack alone in his dark little world again.  A world full of nervous desperate anticipation.  One second passed.  Then another.  Then an eternity, or perhaps another second, before…

“AARRGHHHHHHHHHHHH!” 

White hot pain seared through Jack, lightning bolts of pure agony driving through the inside of his left thigh and obliterating his world of black into tiny shards of torment.  His mind instantly dissolved, pain erasing rational thought for the briefest of seconds and replacing it with pure primal reflex.  Instantly the lips returned to his cock, wrapping themselves around him hungrily and driving down on him before he could even think of another number, his mind still a fog of pain.

“Nope.  Try again dear.  There’s only another 99 possible options…