Mistress Ivy

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The best Keyholder Ever!
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Part 10 of the 24 part series

Updated 06/07/2023
Created 01/18/2016
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Cobb Gherkin walked slowly through the lobby of the PainCafe's Hotel. He paused, breathing through his nose.

Would he get lucky this afternoon? Ivy had intimated last week that the law of averages was moving his way, though of course she was no mathematician.

Last week Ivy had smiled her full lips on his desolate face as she'd locked him up after his forty-five minutes of teasing and torture.

"You're too focused on the results, Cobb. Be happy with the experience."

But he wanted the EXPERIENCE of cumming. It had been 38 days—over a month, since he'd had sevens.

Cobb had looked it up on Yahoo! Answers. According to Yahoo, there was "6/36=1/6 chance of a 7 being rolled. If it has a 1/6 chance of being rolled, it will happen, on average, on the 6th roll."

But Cobb had been seeing Ivy once a week for twenty-two months, and he'd cum, so far seventeen times. Seventeen times out of like, 105 weeks.

As he got on the elevator, he thought of the benefits of this plan, though...chastity was good for him.

He was more focused at work (Cobb was General Manager at Buttermilk Falls Tire & Muffler Fair) and he had a meaningful relationship with a Christian girl, who he could date for long periods of time without pressuring her for sex!

As Cobb approached the door, he tried to focus on the last time he'd gotten sevens, and the pleasure he'd gotten when Ivy had allowed him to cum, humiliatingly, by rubbing his dick on her carpet with his hands cuffed...

The aftermath, being forced to suck up his scum, hadn't been pleasant, but it had been 96 days before THAT , when he'd gotten sevens, and so what a relief it had been!

God, Cobb's dick hurt. Cobb remembered when Ivy and her um, friend Wishbone had taken him for his fitting downstairs in the PainCafe's Dungeonopolis Gift Shop, almost two years before.

He'd fantasized for years about chastity, but the reality was SO much more painful.

He'd had to put aside money, and really work hard for commissions, to come up with five hundred bucks for each visit.

But hey, his hard work had had rewards! He'd gone from a pothead stoner sales associate to now being GM of the whole Tire and Muffler Fair, and was making seventy grand a year.

People often asked why Cobb lived in a rented room in a group house—a SMALL rented room, and why he had no car, just a ten-speed.

He couldn't explain Ivy and how expensive she was, so he told people he had a widowed mother to support. This got him even more Christian girlfriends that he couldn't have sex with!

Inside Ivy's suite, the six foot blonde was counting her money as Noah Touriel tearfully dressed.

Ivy Bornfeld smiled and sighed slightly, and Noah cheered a bit, watching her bosom heave in the frilly camisole blouse.

"Don't be upset, Noah. Four isn't as bad as six, you know..."

But four was pretty bad.

When the dice hit four, Ivy had thrown them right after Noah undressed, and was standing in his chastity belt (hoping for sevens, of course) it meant serious punishment.

Eleven was the next best to seven—the belt removed, a long teasing and just a light paddling. Four was nearly the worst, though.

"I don't program the dice, Noah." Ivy said good humouredly, as she'd tied him over the sawhorse and whipped his bare buttocks with the fiberglass crop.

Then, of course she'd tied Noah's wrists to the ceiling hook in her "parlor" and unlocked his chastity belt...

Better, she'd used the automobile cigarette lighter, a little metal tube with a hot end (that she kept stuck in a generator since of course she couldn't have a'76 Buick in the apartment) to burn a few welts into poor Noah's cock as he'd screamed and cried.

Then Ivy had locked Noah up again, no teasing, and she'd pressed a button, and Wishbone Cheeks, her African American intern, came in from the next room, and took the fully heterosexual Noah into his "lab" and fucked both Noah's holes until Wishbone had cum seven times.

Wishbone had then whipped Noah's butt with a wooden Spencer paddle, the kind with the holes, and sent him back to Ivy.

"Don't be so upset, Noah..." Ivy said sweetly.

"Last week you got threesies, and I gave you an hour long teasing and just one kick in the nuts...and last summer you got sevens TWICE. That's a lot, you know. You told me you wanted me to be strict."

Noah's lower lip trembled a bit, and Ivy, having tucked his five hundred bucks in her camisole, opened her arms, and he ran to them, giving her a big hug and kissing her neck.

"I-I-you just seemed so mad at me, Ivy" This was his special name for her. It was used more literally when the dice hit nines and he was put in bonnet and diapers.

Ivy hugged Noah tight and kissed his cheek and whispered in his ear. "You know the rules, Noah. I don't want to punish you.

It's all about the role, honey. I'm no easier on any of my other clients than you, my little misfit."

She kissed Noah on the lips, and he immediately forgot that she'd just spent the past hour and a half kicking the shit out of him.

"Oh, don't talk about your other clients, Ivy." Noah said brokenly.

"I like to fantasize that you're my-my girl."

And he came to visit quite often. Noah was a former Pittsburgh Steeler, receiving healthy royalties from his visage on a Wheaties box, and could afford to visit Ivy two to five times a week.

He'd just "retired" from the team a year ago, but several times, when overcome by all the pressures of the game (it's tough to be a wide receiver whose chastity belt gets knocked by tackling Miami Dolphins) would send for Ivy to travel with him as he played various games across the country.

He'd begged Ivy to marry him, and it would've broken his heart to know that Ivy had no sexual interest in men who needed to be dominated, and in fact, was Wishbone's common-law wife...

Still, Noah had been Ivy's client for seven and a half years, and was quite devoted to her.

Noah kissed her again and hugged her, and then Ivy gently reminded him that she had another "friend" coming.

"Honey, I'll see you soon. Why don't you schedule for Friday. I'll give you three hours for only a thousand dollars. I'm feeling so generous. Maybe you'll get sevens!"

Thus cheered, Noah blew his nose, as he was still hurting from Wishbone's paddle, and walked out.

He hated Wishbone, and it was interesting how Ivy would almost side with Noah against Wishbone, until the dice were rolled...

"I hope that bad man doesn't punish you..." and then she'd comfort him as if he were an abused wife after Wishbone had done his dirty work.

Once, Noah had been bleeding from the rectum after Noah had shoved his dick in a little too hard (and then made Noah lick his shit off Wishbone's wiener.)

Yes, and she'd held the weeping Noah in her arms for nearly half an hour, lamenting that she had such an evil person in her employ. (As if she had no control over the situation!)

But, as Noah opened the door he gave Ivy a cryptic, desperate wave, and she smiled, while thinking that he was the wussiest human being, for a 390 pound athlete. What a freakin' crybaby!

Earlier that morning she'd had a timorous looking funeral director, who had rolled eights—which was fifty with the bullwhip downtown at her warehouse....

The eights were rolled, Thurman the undertaker had blanched, but he'd smiled gamely. "Guess I better get dressed again, Miss Ivy."

And she'd smiled sympathetically. He'd left with Wishbone, she'd watched "The View" and when he'd returned, naked, welted and in a sack (Carried over Wishbone's shoulder from the parking garage of the PainCafe hotel) there were no complaints.

Thurman had rolled out of the sack, the welts and red bloody streaks all over his cringing stiff little body.

Eights called for a thirty minute manual tease combined with sandpaper being rubbed on the nipples.

Wishbone had tied Thurman down and gone to work with the sandpaper, while Ivy had gently rubbed and stroked Thurman's hard cock, (his last Sevens orgasm had been 83 days before) and she'd leaned over to show him her full cleavage.

None of Ivy's customers had ever seen her bare breasts...but she did give the stoic Thurman a flash of nipple!

After the tease was over, and she pulled her nimble red-tipped fingers away just six seconds before Thurmie would have orgasmed, she re-locked his belt and he'd kissed her feet (and Wishbones) and silently dressed and left.

What a dream client!

And even this morning, real early, she'd gotten Hardesty McGonigle.

Hardy always showed up on Wednesday mornings, interrupting his daily jog, in T-shirt and shorts. Hardy was on the honor system, since he was sort of happily married.

He fucked his wife, holding back his orgasms, and when he got sevens, he'd hold off until he went home to Elyse and given her a good shot. (This had impregnated her twice now...all that backed up spooge.)

Hardy was great because he masturbated in his office, without letting himself cum, he'd call her on his cell, and she only charged him a hundred per ten minute call...

Oh, she'd talk sexy and blather on about playing with her tits and how he wasn't worthy...all that submissive shit...

And then once a week, or twice sometimes, Hardy would come in, throw the dice, and take his punishments...or go home to do his reward faithfully with his wife.

And he didn't bitch and moan like so many of the other dorks.

Now, Ivy paused to re-apply her makeup.

She had a concoction of putting on soft pink lipstick first, then, taking a slightly darker shade of sparkly pink lip gloss on the tips of her fingers and gently tapping it on the edges of her lips so it shone.

This gave Ivy's lips a magical touch, and made men wish she would blow them, as she was putting out cigars on their balls, et cetera.

Wishbone opened the door to his "lab" and gave her a wink.

Ivy knew that although the Bone was bisexual, he really loved her best...

Hey but what better job for a third grade dropout, and San Quentin parolee than to cum in white men's mouths and rectums ten to fifteen times a day (Wishbone was quite fertile) and make the equivalence of $50,000 a year for doing it?

There was a knock on the door.

"Is that Professor Argyle?" Wishbone asked, but Ivy shook her head. The Prof had rescheduled for Friday, and Ivy was going to eat a lot of Mac and cheese, so she could use her lactose intolerance to do a big crapper in his mouth.

Ivy opened the door, and there was Cobb Gherkin, looking hopeful. She smiled. "Hey baby...how's it going?"

She gave Cobb a big kiss on the cheek and he hugged her.

"Miss Ivy, I've really, really missed you. Really." He looked at her with puppy dog eyes.

"Really, Cobb? Last week you were such a crybaby you just flitted out of here."

He colored. Ivy had a way of being sweet and then REALLY nasty. But last week had been quite painful.

Cobb had rolled a two, and this had meant that Ivy had tied him down, stroking his cock with her long nails and squeezing her boobs together in the little black demi bra she'd been in...

Yes, but every twenty seconds, she'd whacked his balls with the spike heel of one of her Burberry pumps.

It had been awesome and horrible. "You're my sweet baby" she'd croon, leaning over on the bed to kiss him, and then pulling back and whacking his cock and balls again and again with the heel.

Then, as she was stroking him, Wishbone came in and plunged his dick in Cobb's mouth.

"Make Wishbone cum in the next three minutes and I'll give you a pain free tease for the rest of the hour...

Hey, but if you don't, I'm turning you over the sawhorse for twenty-five from my Scourge."

The Scourge was a short whip made of leather thongs knotted with little bits of metal.

Cobb had sucked Wishbone's long dick desperately, it not helping that Wishbone kept slapping his face and screaming

"Make me cum, white bitch!" and he was also quite distracted by the wonderful massage his dick was getting from Ivy...but he couldn't make Cobb cum.

Ivy had shook her head sadly as Cobb pulled his dick out (he'd cum twice that day, so that might be part of it) and she'd shook her head sorrowfully.

"I feel like you didn't even try...so I'm going to use the Scourge on your dick before I throw you across the sawhorse!"

Cobb had been in acute pain for five days...his crotch on fire for FIVE DAYS.

He had considered breaking off his relationship with Ivy, but she was all he lived for.

Now Cobb wondered if he might get a mild toss...he didn't have much hope of Sevens, after all.

Ivy gave Cobb a sincere smile.

"I felt so bad about last week, honey. I know you tried real hard. I really, really hope that you get a lucky roll today."

Cobb began undressing.

He knew that even if he got Sevens, he also had to jerk his cock with his left hand, and had to cum within five minutes, or he'd have to stop, and take another roll, which of course statistically, would probably NOT be sevens.

Once he'd actually become hysterical, because of course just because you're super horny doesn't mean you'll cum...and he hadn't.

Wishbone had had to come out and whip Cobb's dick thirty times with a rattan cane to calm him down before his second roll.

That had been a five. Fivesies was bad because it meant that Cobb had to visit Ivy for five weeks each time with a 2 hour tease—that was the good news—but he was ineligible for another roll of the dice

Which meant five weeks of chastity, unless he wanted to mortgage his house and do five five hundred buck sessions in a week, or a day, to get to roll again.

Also, Wishbone gave him a hard Spencer paddling every time for the five weeks. Fivesies wasn't fun.

"Can-can I have an initial tease before the roll?" Cobb asked hesitantly.

"I mean, I might not get a tease if I have a bad roll, and I'd just—I have the extra money."

An initial pre-roll tease was five hundred dollars an hour, but no orgasm.

Ivy smiled, nodding.

"I have an hour—or two?"

Ivy tucked in her camisole somewhat absently, and her breasts pushed the Lycra leopard print camisole forward, emphasizing the lace trim...

And she pulled the drawstring a bit, and the effect on her cleavage was something else.

Cobb nodded enthusiastically, he resembled a Bobble-Head, Ivy thought.

"I sold some of my stock options, and we can have a two hour tease, and maybe...I'll roll sevenses later on."

Ivy bit the inside of her cheek to keep from smiling, as she considered this underhanded bribe.

As if she could affect the roll of the dice! Ivy's best friend, Artemis, who had started as a TeaseDenial Specialist at the PainCafe sometime around the end of the Reagan era, had always advised Ivy that she not make any compromises based on cash.

"After all, honey, more will come, if they don't cum."

Artemis had said sagely. Both women had laughed at this, admittedly weak, witticism.

And it was true. Guys who were into chastity did not respect you if you gave away power....and the one way to lose a client was to ignore the will of the dice.

But there was no harm in flirting, Ivy thought as she smiled and ran her tongue across her specially painted lips, staring at Cobb...

"Okay, baby, two hours sounds fine. That's a thousand dollars...plus of course the five hundred for your post-roll session."

Ten minutes later fifteen hundred dollars was resting in Ivy's bodice, and Cobb was cuffed, and naked... and she was unlocking his chastity device.

After she went and dropped the belt in her dishwasher, to get the grime off, Ivy came back with a little bowl of sudsy water.

Then slowly, carefully bathed Cobb's cock and balls, after all...water hadn't been there since the last session!

Cobb's dick grew thick and hard in her little white fingers, and as she gently scraped his full scrotum with her long nails, he gasped.

It had been only 38 days since his last orgasm, but Cobb was a fertile young guy, and he really, really was horny.

The night before he'd been necking with Gyrene Dowson, stalwart maiden of the Buttermilk Falls Salvation Temple...and she'd actually said to him...

"Let's do it, even though it's sinful, Cobb."

Gyrene was an adorable redhead, with huge tits and full lips, and he'd known she'd laugh her ass off and dump him if she got him undressed and saw his chastity belt.

He'd gotten her naked over the past few months, and finger-fucked her, and even eaten her out, but insisted he had to keep his pants on to respect her um, pearl without price.

Cobb also fooled around with Parmesan Cameron, the receptionist at Buttermilk Falls Tire and Muffler Fair, and he'd pulled her panties down in her office and licked her pussy as she sat behind the desk...and how unfair was that?

She should be blowing HIM, but hey...he couldn't get the belt off.

Now, he was in absolute heaven, and hell...

Ivy pulled a pin out of her blonde bun and her hair fell around her shoulders in long, curling tresses, and she kept giving him light kisses as she ran her fingers up and down his pulsating rod...

Cobb was getting hornier and hornier...and he'd paid for two glorious hours with this girl...but where was she going?

But beautiful Ivy was walking out on him, after he gave her fifteen hundred big ones?

"B-but I paid you for a two hour tease!"

Cobb said, his eyes rolling in his head as Wishbone came out of the back room.

Cobb's throat constricted as he saw the huge black pick up the Astroglide and pump some of it into his huge ebony palm.

"Yes, and Wishie will tease you honey...

I'll come back up for the dice roll. But I have to go now." With that, Ivy stepped into the bedroom, and Wishbone began roughly handing Cobb's erection.

Wishbone put his big lips and flat nose right in Cobb's face. "Don't you cum, now...I'll kick yo' ass, white boy. I'm not used to the teasing part of this shit."

But of course there was little chance of that. Cobb began getting limp in Wishbone's large hands.

This offended the Negro, who gritted his teeth and slapped Cobb in the face.

"What's wrong, my brother, you not attracted to me. You goddamn white devils have just lowered my self esteem for as long as I can remember. Get this dick hard or I'll get MAD."

As Wishbone continued to slap the cuffed Cobb's face and pinch his nipples, Ivy came out of the bedroom, dressed in a lovely flowered gown, and waved good-bye to her boys.

She had to give Momma a status report on all the good stuff that was going on with their shared Home Business!

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RegretsRegretsabout 6 years ago
Rubbing his dick on the carpet

I read no further,how disgusting. Chastity is supposed to be a friendly activity with the reward side very much tipped to the female. She may date others for instance,to demonstrate her privilege. There are some lesser pleasure for the Male,if he is obedient, by demonstrating the correct attitude in the bedroom, and pasive acceptance of her nocturnal activity outside the home,and by conscientious attention to chores.Both sides take pride in his progress,but that does take several months before a marked change can be agreed. The story?.....I stopped reading right there.

AnonymousAnonymousabout 8 years ago
Sentence / Paragraph

Why is every sentence you write a new paragraph? Start thinking quality and not quantity with all these stories you put out!

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