My Master was a Matchmaker

SAID THE SPIDER TO THE FLY

JULY 2018 STORIES

THE MAN FROM MOUNT EIDERDOWN

Cheverus Glass knelt before Specs, looking a little ill at ease out of his gray suit from Rogers Peet. Cheverus began stroking his penis slowly, biting his tongue as he did it.

"Haven't touched this in a long time." Cheverus said, looking up at Specs, who was a little bored. Cheverus was a long distance client, he came to Buttermilk Falls four times a year from Mount Eiderdown, for a chance at orgasm.

When Cheverus got his cock very hard and dripping, Specs blew a whistle through two fingers, and Cheverus obediently put his hands behind his back, though his eyes showed the pain.

And why shouldn't he? It had been three months since the last time he'd been able to touch himself, and about nine months since his last orgasm.

Specs went to the little glass fishbowl with the slips of paper, and brought them to Cheverus. "Wishing you luck there, buddy." Specs said, grinning.

There was so much going on in the Dungeon today.

In the suite right next to this one, Orvis and Verlene Wisniewski, a submissive couple, was having their bound behinds shot at with BB pellets by a rabid Male Master, Sir Proxmire. Prox was incredibly energetic and a little insane, but you had to count on him for making his "intentions clear"

And it freed up Specs to work on old favorite clients, like poor Cheverus.

Poor Chev! In the past year, Specs had installed an app on his phone and a "stimulator" on Chev's chastity device that alternately sent teasing buzzes and painful shocks...in addition to everything else.

Chev was getting his money's worth. Especially since Buttermilk Falls and Mount Eiderdown were so far from each other...and yet, Specs had had quite a party with the app.

And now Chev was taking his chance on whether or not he'd get to cum, through the Fishbowl.

Cheverus reached into the fishbowl, and pulled out a sheet, looked at it, and burst into tears. Cheverus was the macho type, but it was understandable if the little slip of paper didn't have what he wanted on it.

"What's wrong, Cheverus? Did you not qualify?"

Cheverus handed the slip of paper to Specs, and began crying in his cupped hands, covering his entire face.

On the little piece of paper it said. FIFTEEN CANE WHACKS TO COCK AND BALLS.

Specs could tell that Cheverus Glass was not used to crying; he was the type to bite his tongue first. But of course nearly a year of no cumming with these VERY occasional chances...couldn't be easy. But, he did sign up for it.

"Cheverus" Specs said gently. "Why don't we get the caning out of the way."

Certainly he could've gotten out of the chastity belt. It was only tied together with plastic locks, as Cheverus had to fly a lot, and couldn't have metal bands. But the plastic locks had little numbers on them, and Cheverus knew that if he broke into it, Specs would know.

Cheverus's hands left his wet face and he sighed, and stood, walking over to Specs's metal drafting table. He lay his cock and balls on the table.

At least Cheverus manned up. So many of Specs's submissives just kind of chickened out at this point, terminated their contracts...whatever.

Specs got the bamboo cane and came up close, noting that Cheverus's cock was still hard, and lying across his quite full testicles.

Specs raised the cane and smiled.

Cheverus began quivering. Specs swung the cane just before hitting his cock.

"So what's going on at home?" Specs asked as he raised the cane again.

Chev had begun his chastity training as a request of his then-dominant wife, Vivian.

Cheverus had cheated on Vivian, and Viv had, in turn, put him in chastity. For several years when Cheverus visited Buttermilk Falls it was because Specs held the keys.

Vivian's feeling about the whole thing was, she didn't want to tease and mess around with Chev at all, she just wanted his tongue to work, his wallet to fund her fun, and of course his ass to take her whip, the enema bag and the strap-on when she was feeling a bit violent.

So when Cheverus visited Buttermilk Falls, Specs would review Viv's e-mails regarding her husband's behavior. Sometimes things were better than others, Vivian, like many women, got bitchy or was on the rag, but basically, it was behaviorally based.

Chev qualified for orgasm if his behavior was exemplary. At the time, Cheverus had a very secure locking belt.

If he'd been good about doing the housework, signed over his paychecks to Vivian, and had willingly gone down on Vivian and her various boyfriends (Viv had a double standard on who was allowed to romantically roam in the marriage) things went well.

Then, Specs would unlock Chev and allow him to jerk off onto his Master's boots and lick it up.

At that time, Cheverus's visits had been monthly. At home, Vivian didn't give him any manual stimulation, his tongue was kept quite busy. But Chev went about his business.

In time, Vivian raised her standards of what good behavior was. "Cheverus has been inattentive this month." Or, God forbid she mentioned his being "moody."

Then, Specs denied poor Chev his orgasm, and sometimes gave him a vicious flogging as well. Once, Steiger Sloane, who owned "Sloane Steakhouses" that competed hotly with Cheverus's family business, the chain of "Gamecock Cafes." came separately as a submissive on the same day...

Specs noticed too much complaint about ego in Vivian's e-mails, so Specs had Chev suck Steiger off. This was a great reward for Steiger because first, Chev was not gay, second Steiger WAS gay, and thirdly, it was a real kick for Steiger's competitor to have to fellate him...

But eventually, Vivian and Cheverus split up, and she moved to Los Angeles with her young lover, both supported, naturally, with a large check from Chev. The alimony was really high, and Chev discovered he could only afford to visit Specs every ninety days.

Specs had pointed out that he could give up the whole thing now, he was single and fancy free, but Chev felt that chastity training kept him "focused" and he could deal with having a chance to cum only once every three months.

But, since Chev had expanded his cafes internationally, with the goal of a "Gamecock Cafe" in every hamlet, he couldn't wear a locking steel device anymore because of the air travel. So Chev began wearing a plastic thing that he could easily have broken into, but the plastic lock had a number on it, and of course Specs would have known...

Since Specs didn't have Vivian's progress reports anymore, and didn't feel like setting up a nanny cam in Chev's house to watch him, they decided to do the Fishbowl method.

Specs had filled the little glass bowl with all sorts of messages, only four of which were "masturbate to orgasm" Others said "Dress in a hair ribbon and pinafore and play jacks in front of dungeon" or "hang by nipples for thirty minutes" Ten said "Ruined Orgasm" and a couple mischievously went "Masturbate with left hand for 2 minutes and stop."

But most were punishment based. and the one that Cheverus was obliged to go through today was a doozy. True, Specs had gone over the fishbowl options with Chev when he designed this system, and Chev had approved and been aroused by all... but..oooh!

Now, a Cock and Ball caning while Cheverus's penis and scrotum were lying across a metal table was a rough one. Specs had generously pointed out that since Chev might go limp after the first swat, something had to support his junk for subsequent punishment, right?

Presently, Specs swung the bamboo cane down on Cheverus's cock and balls hard. WHACK! Specs lifted the cane again. WHACK!

Specs was going to swing a third time, but Cheverus, too manly to scream, was barely holding onto the table. Tears were running down his cheeks. On the other hand, his penis looked like it was getting even harder.

Specs realized that although Chev was having a masochistic peak here, it might not be good to continue the whipping without a rest.

"We can break for a bit." Specs said kindly. "You know, Cheverus, if you like, I'll let you draw again, and get a different slip. Or you can do a minor penalty, like sucking me off, and for that I'll let you jerk off, no punishment. It has been nine months after all."

Cheverus, very pale, shook his head. "I must follow the rules."

Chev smiled slightly. "If you want, Master, I'll fellate you anyway. I have no desire to do this, as I am heterosexual, but I am a true submissive."

Specs smiled inwardly. Specs was a true bisexual, but Chev was old and fat, and it would be no thrill for Specs...no no.

"Cheverus, now that you pay all this moolah to keep Vivian and her lover living large in Lotusland, you can really no longer afford monthly visits, which is why you've been coming quarterly...

I think it might not be so good to go so long between chances to cum. Frankly, as you know, the last three times, over nine months, you've been completely denied.

"Are you worried about my prostate, Master Specs?" Chev asked, smiling.

He coughed. "I am drained anally twice a month no worries about that. I have an understanding physician, she was my wife's gynecologist and I pay her with cash and an hour's lapping on my knees.

Well, more fun than seeing an old man proctologist, Specs guessed.

"Yes, but what about your morale?" Specs asked.

"I mean, all those months not being able to touch yourself, not being able to date..."

"I take several different women to the ballet and the opera, and plays. They think I'm a perfect gentleman. It is a bit frustrating, but I think I have a full cultural life."

Chev then said, "And, remember, I was quite the cocksman before Vivian locked me up. I've had more than my share of women. I like being a slave, it would be really nice to be one full time to a beautiful woman, especially one that teased me, but this isn't a bad life."

Now Cheverus's cock was filling up with blood again, getting quite tumescent. Even just talking about submission seemed to turn him on tremendously.

"Okay, let's use the cane again." Specs said. "We have to get this over, unless you want to opt out."

Cheverus again turned a little pale, kind of like Jack Nicholson when he was to get the shock treatments in "One Flew Over the Cuckoo's Nest."

"Yes, Master Specs. "Chev balanced his cock and balls on the table again and put his hands behind his back.

Five whacks later, and Cheverus was almost staggering. His penis had gotten small again and there were several marks that might be permanent. No, amazing, he's still getting hard, Specs thought.

But this had to stop. The caning was done. But what could Specs do? Chev was such an enthusiastic slave boy.

"You okay there, Cheverus?"

"Yes, Master." Chev said. "I'm lucky, I could have drawn the habaneras pepper enema, or the thorny branch thrashing. I think that's what I drew last time."

"Yes, I was surprised to see you cry, being an ex-Marine but of course the thorns must've been awful. You've not gotten the one yet where we shove a cocklebur up you know where, but...something to look forward to."

"Yes, Master Specs. Or I could have selected the one where my feet are beaten and I must say, I never knew how painful that could be."

"The feel are very sensitive. Look, why don't you get back on your knees and edge your cock again, very slowly."

"I do have eight more strokes of the cane to endure." Chev said hopefully.

Was he insane? "Yes, but we don't want to send you to the E/R. I am ordering you to gently stroke your cock. Really, really gently, since I just whacked it.

Chev dropped to his knees and began rubbing his cock. He looked so lonely. The poor man, escorting old bags to the opera. Specs pressed a button and subsequently there was a knock on the door.

A little blonde came in...Chev looked up and noticed this, and her stupefying breasts.

"What's up, Specs?" she asked.

"Arcibel, this is Cheverus. He's edging himself, but the poor bastard hasn't had a girl's hand on his cock in several years now. Why don't you play with his pee-pee a little?

Arcibel smiled and twitched her button nose.

"Chev will love your soft fingers. As I recall, Cheverus is an oarsman, and his hands on the gulls all these years must've made them very rough."

Cheverus seemed delighted when Arcibel approached. Her hair was tied back in a long ponytail, and she had a bewitching, enigmatic smile...the full lips were something to behold.

Vivian had been a somewhat overweight thin-lipped woman, with an unfortunate mole, and certainly, Arcie was a pleasant contrast.

Arcibel pulled off her sweater displaying her full, bouncing boobs that seemed to ignore gravity.

"You like what you see, paisan?" Arcibel asked with a big grin.

Arcibel began rubbing Chev's dick and it swelled as her red nails did the dance, massaging the thick veins in the shaft gently.

"What a nice sized schlong, baby." Arcibel said, giggling. "Too bad you're a bitch-boy submissive, not fit to fuck a girl."

"You tell him, Arcie." Specs snickered. "Only real men for you, right?"

"I wish I wasn't such a submissive, but it's just in my nature, Miss Arcibel." Chev was moaning as her gentle hands did their skilled work.

Arci kissed Chev's ear. She whispered. "You can't fuck anyone, because what woman wants to have sex with a little bitch? You should go out in drag and blow soldiers in the alley."

"I was a Marine once" Chev protested faintly.

Arcibel kissed Chev's neck and rubbed faster.

"Really? A Marine, huh? Did your fellow Marines know that you were a sissy-faggot panty boy?"

As Arcie's soft fingers rubbed and tickled Chev's growing erection, her tinkling voice humiliated him, but as the emasculating words continued, he became more and more excited.

"Specs, he's ready to pop." Arcie said, looking over at her supervisor.

"Slow him down, Arcie." Specs said with a smile. "In the way you know how."

Arci smiled and gazed into Chev's eyes. "I only do this because I love you, tranny bait."

Arci's teeth met and she kicked Chev violently in the balls. Cheverus fell on the floor, holding his crotch.

Arci watched Chev cry for a bit, and then she pulled a dainty foot out of her shoe and ran her manicured toes up and down Chev's cock as he lay on the floor.

Chev looked up at Arcibel and her absolutely perky D-cup breasts...her hands were on her hips and her little foot really was stimulating the hell out of his groin now.

Up and down her toes went until he was getting aroused once more.

"Okay, get up, faggot." Arcibel said brusquely. "Your edging isn't done yet."

When Chev was slow to respond, Arcibel bent down and grabbed Chev by a nipple and dragged him up...but when he was on his feet he looked a bit terrified of this evil little creature.

"Oh, baby, don't be mad at Arcibel!" Arci gave Cheverus a huge kiss and rubbed her tits against his broad chest.

Chev moved closer, and Arci moved back.

"Calm yourself there, Princess" Arci said, smiling. "You can't jump on me like you're a man. Really, you should be in full makeup, and we should be shoving gerbils up your ass through a plastic tube."

Specs laughed, and walked out of the room. He knew Arcibel had this covered.

Specs went to his office and watched some Tivoed "South Park" reruns and smoked a joint, and about two hours later, he returned.

"So how did we do, Arci?" Specs asked.

At this point, Arci was still jerking Cheverus's dick, but he was once again on the floor, on his back, and she was perched on his legs, using her cute little hands to rub and pull his engorged penis.

It seemed to be getting very stiff. Just before Arci turned to answer Specs she took her little fist and lifted it.

"Spread your legs and pull up your dick, Chevvie."

"I'm not about to cum, you don't have to-"

"Who's giving the orders here, Nancy-boy?"

"P-please."

"We gotta calm you down, Chev. Look at all that precum, it's gross."

Chev blanched but he spread his legs and Arcibel nodded. "I'll pick up your dick, it's okay."

Arci took one little hand and pulled up Chev's dick and used her other hand in a fist to slam into his scrotum.

Chev began sobbing, but it was clear he was terribly aroused by all this.

"All right, Arcie, that's enough." Specs said with a chortle. "Up off the floor, you too, Cheverus."

They both rose, and Specs could see that Chev's cock and balls were a little blue, but he was still very horny and quite excited. It had been nearly a year since he'd cum, and it was amazing he'd not had an accident, no matter how many times Arci had "calmed him down".

Arci snickered. "I have Gaetano, still locked in a pillory in the Beige Room, and Maitland Grim in the cellar."

"Really, the senator, Maitland-" Chev looked surprised.

"He's a State Senator, not that impressive, and he's wearing a tutu." Arcibel said dismissively. "You are much cuter, Chevvie."

Specs was amazed. Even on her tippie toes, Arcibel was so much smaller than Chev, but she really had him fascinated and intimidated.

"You aren't mad at Arci are you, Chev?" Arci leaned into Cheverus and put her arms around his neck, practically having to climb him to do this. "Was Arcibel too hard on her wimpy boy?"

Cheverus smiled weakly and then bigger as Arcibel pulled him to her and gave him a huge kiss with her glossed lips. Arci ground her crotch against Chev's bulging dick and he returned the favor, reaching around to grab her buttocks.

Suddenly Arcibel stepped back and slapped Cheverus across the face and then kicked him in the nuts once more, and again he fell.

"Can you believe it?" Arcibel said matter-of-factly. "I try to be nice, and he wants to rape me."

But as she spoke, she absentmindedly rubbed her foot against his penis until Chev began panting..

Finally Cheverus rose again, and his penis was so hard, it was bouncing up and down and looked as if it could bat for the Yankees.

"You love Arcibel don't you, Chevvie?" Arci pouted and made her eyes look very big. "Arcibel's in love with her widdle boo-boo."

Although Cheverus was a little wary of the moody girl, he came a little closer, her breasts were gorgeous with the soft pink nipples and enormous areolas.

Arci put her hands under her tits and jiggled them just under Chev's nose.

"You wish you could kiss my nipples, suck on them, right?"

Chev nodded, eagerly.

"Forget it. My tits are for big, strong heterosexual men."

But then she grazed him with her tits, and he stepped a little closer.

Arci stroked Chev's cock a bit and he began breathing heavily once more.

"You are a good sport, Cheverus. I vote we let you cum, you got some caning and some meani-ness from Arcibel here, and you deserve a good time." Specs smiled and hoped that Chev would allow this generosity.

But of course, no one was as hard on Chev as he himself was...

And, Arci leaned forward once more and began necking with Cheverus.

And Chev was thrilled, not really thinking about whether he'd be knee'd again. He was just blown away. Never had he been with a girl this hot, and certainly not after nearly ten months of abstinence.

"Or..." Specs suggested..."If you want to stick with the chastity plan, I'll lock you back up and you can service Miss Arcibel's clitoris. I know you're good at that."

Specs left the room, hoping the two would work it out.

He wondered if he should let Cheverus visit the dungeon monthly at a lower rate, it might give him more of a chance at pulling the "orgasm" slip...

Still, Specs wasn't running a charity.

But then again, Mount Eiderdown was ripe for a dungeon "franchise". If Specs sent Arcibel and some other girls to start a center there, they'd need lodgings and Chev had a big house.

But, as Specs was mentally calculating what kind of profits there would be, the door opened.