Miless Conundrums Ch 09

Gretchen completely stubbed out her cigarette on my tortured glans, and then held the butt up to my face. "Swallow it!" she demanded.

I shook my head, and she punched me in the stomach. I buckled over, straining at my hands cuffed behind my back, and as my mouth opened, Gretchen shoved the disgusting butt in, and held my nose until I swallowed it, retching.

"See, that's worse than smoking a cigarette, dude...Miles the pure has finally gotten a little impurity!" Mike laughed, and I knew where the anger was coming from.

Not only did I not smoke, and I drank only in moderation, but I had once reported Mike and the other guys in the frat after they'd catapulted piss filled balloons onto the heads of the Dean of Sciences and his colleagues.

This had ruined Mike's chances of taking the Foreign Service exam, as his security clearance had been ruined, and Mike had been condemned to a blue-collar career.

Was that why Mike was being so down on me? Was I such a tightass, that he was conspiring with my wife to make me miserable now?

There was no doubt that he was really, really hostile to me!

Gretchen now got up in my face, and began breathing hard.

"You make me ill, Miles! You're just a repugnant excuse for a male!"

Gretchen grabbed my cock and pulled it, and it got hard instantly, despite the burns. She ran her fingers across it slowly, and spat in disgust.

"All you want to do is mount me like a dog!" she screamed.

Gretchen ran to the coffee table and picked up a bamboo cane she'd purchased recently, and stalked back over to me.

Rubbing the end of the cane on the tip of my cock, Gretchen looked straight into my eyes. "Don't you think ever that my needs might be more important?"

Asserting myself slightly, I said "But I performed oral sex on you, honey, I spend money on you I--"

WHACK! WHACK! CRACK!

Gretchen's cane came down on my cock again and again, and I fell to my knees, weeping.

"I, I, I..." Gretchen snarled. "That's all it's about is I, right Miles?"

Gretchen walked behind me, and began whacking my butt to get me up. "Get up!" She flailed at my buttocks till I arose again.

"Mike" she appealed to my roommate and ex-best friend, "How do we get Milesey's mind off his goddam groin?"

Somehow, after this question, I wound up in Mike's basement workshop.

"Finally you're going to take my advice" Mike said as he grabbed my balls and pulled them up to his worktable.

In horror, I watched him push my testicles into the metal vice hooked to the table.

Mike then began swinging the little metal rod that cinched the vice together, as Gretchen played with my cock.

"See, baby..." Gretchen said in a soothing voice. "You must learn that your dick is not the head of the house any more..."

Suddenly, the vice completely closed on my balls, smushing them together, and I screamed. Gretchen kept stroking my cock, which amazingly remained stiff.

Then they took my balls out of the vice and tried squeezing my cock between the cruel metal until I howled with anguish.

"But honey, I thought you liked it when I played with your cock" Gretchen said teasingly. "Hey, what about just squeezing the cockhead, or the glans, Mikey?"

Eventually Mike had released the vice, and Gretchen and Mike had unlocked my handcuffs left me downstairs in the basement, where...I masturbated!

You'd think I would call the police or something, but the whole business with the punishment and humiliation had me really horny.

The following weekend was incomprehensibly bizaare.

On Friday night I was reading Business Week when Gretchen informed me that she was going away for the weekend with Naomi, the woman she'd met through Master Nash.

Before I could register an objection, the doorbell rang, and Gretchen opened it, and there were Naomi and Skyler.

Gretchen and Naomi greeted each other with cheek kisses, and as soon as they came into the living room, Skyler instantly stripped down to his chastity device.

God, he knows how to make himself comfortable, I thought, my face hidden behind the magazine.

"Miles, get up! Take off your clothes, too. You and Skyler are spending the weekend here together." Gretchen said cheerily.

"Wait--what-what do you mean, Skyler and I are spending the weekend here? And why do I have to take--?" Before I could finish my sentence, icy blonde Naomi stepped over to my chair.

Naomi grabbed me by the hair and dragged me up.

"When your Mistress tells you to take your goddamn clothes off" Naomi hissed in my face. "You'll do as she commands."

I was temporarily overcome by this hot blonde in a leather miniskirt staring in my face, and clutching my hair.

Suddenly her fishnet knee came up into my groin. There was an overwhelming pain in my balls, and I keeled over.

When I came to, I was sitting naked across from Skyler, whose nakedness was, in combination with his obesity, quite repulsive.

I tried to get up and felt myself pulled down by my scrotum. I looked down in horror to discover that there was a small circular ring locked around my cock and balls, connected by a chain of about four feet to Skyler's chastity device.

I assessed the situation. Skyler and I were locked together by the balls, naked! And for the weekend?

Skyler looked at me over his disgusting flabby stomach. "Yeah, I know. Mistress Naomi put out some TV dinners for us, but she and your wife locked away the TV and said this would be a chance for us to get to know one another."

I couldn't believe it. Skyler Soames was the epitome of revolting--he had a nationwide radio show bashing welfare, gays, abortion, minorities, and big government.

Despite being an investment banker now, I had been quite the long-haired, pothead leftie in my university days, protesting for an end to apartheid in South Africa, raising hell outside the International Monetary Fund, and all that sort of thing.

Many times I would catch "The Soames Sermon" while turning the dial for National Public Radio, and I'd hear him waxing effusively about the Iraq war, Ronald Reagan and how wonderful President Bush was, and I'd want to throw up in the car.

And now I was cuffed to the man's balls until Monday!

At least my cock and balls were hanging free outside of the horrible metal ring. Skyler's cock was encased in that chastity device thing, and it must be quite sweaty, I thought.

"Hey, do you mind if I get a beer?" Skyler asked me. He began getting up off the floor, and I felt my crotch being dragged.

Good God, I thought.

Skyler, on his haunches looked at me irritatedly. "You're going to have to get up as well, Miles."

I rolled my eyes and pushed myself up, until we were both standing, the four-foot chain hanging between us.

"It's just that I'm really thirsty." Skyler said as we edged towards the kitchen, the chain swinging between us.

"This morning Naomi made me lick out seven used condoms from her little party last night--"

I put my hand up. "Look, Soames. Too much information."

"Well, I'm just saying," Sky opened the fridge, "Other men's semen parches my throat, though when I lick up my own, it doesn't seem to bother me."

He should say that on his goddam radio show, I thought. Much more interesting than his criticisms of Greenpeace.

After Skyler got his beer, he moved towards me, and I realized I had to walk in tandem towards the couch. He was staring at my prick, which I found rather disconcerting.

There is something creepy about two middle aged men chained together in a living room, I thought.

"Why are you staring at my dick, Soames?" I asked testily, as we sat down on the couch.

"I just envy you." Sky said simply. "I haven't had unfettered access to my own penis in twenty-seven months. And in that time, I've only been allowed to jerk off to eleven orgasms."

"That's not many" I admitted. Gross, he's sweating under his armpits, and its rolling down all over his naked belly and on Grandmother's Chippendale camel back sofa.

"Actually, it's worse than that." Skyler said, as he sipped the Heineken.

"After I told Naomi of my fantasies of orgasm denial, and we bought the chastity device, I got about eight orgasms the first year, but hell, in the past eighteen months, it's been about three."

Skyler looked out the window. Could people see us? I really was worried about that. I'm not a frigging homosexual, after all.

"Naomi likes to tie me down to the bed about three or four times a week, and unlock my chastity device." Skyler said in a monotone.

"She always dresses in some hot little body stocking, or a pink tube top that looks painted on...it's incredible."

"Then she pulls and strokes my dick until I'm quite hard, and when I'm begging to cum, she beats it back down with a metal ruler, or sometimes a thorn branch from the back yard.

Then she begins stroking my dick again, over and over, teasing me up, and whipping me down until she bores of it, and then I'm locked up again. It's quite stressful."

"Well, if you don't like it, Soames, why don't you break it off with her?" I asked. "You can't possibly tell me she's doing this completely against your will."

"She isn't, Miles." Skyler said. "I do have fantasies of being in a tease and denial relationship, and it completely arouses me...but sometimes it's just a bit too much."

"Certainly I agree, it's exciting to be dominated" I admitted sheepishly. "There's nothing keeping me enslaved to Gretchen, she's not blackmailing me...

I guess I do get excited about the whippings, and humiliations she puts me through. And her forbidding me to masturbate is exciting. It makes when I do get to play with my penis quite the treat.

And, of course I was the one to tell Gretchen about my femdom fantasies, just as you did with Naomi, Skyler. It does turn me on, but she goes a bit too far in her zeal to humiliate me, Gretchen does."

"It's worth it, though, I think" Skyler said earnestly.

"You know, Miles, for years I rented BDSM porn tapes, and paid whores to whip my naked butt, and read those terrible contrived stories in the bondage section of Penthouse "Variations", and I was miserable.

Naomi makes me feel like a true slave, and I am aroused all the time, and that's worth any number of orgasms, don't you think? And she orders me to do bizaare things, and I deal well with that, too."

"See, that's the problem" I said, shaking my head. "I have to admit no matter how strange or humiliating the orders I get from Gretchen are, I get more and more excited...I'm sure you heard about the time I was nailed to a board!"

Skyler nodded sympathetically, and finished his beer.

"But I can't let things go too far, Skyler. You must understand, I'm more than a wimpy cuckold slave, right?"

Skyler laughed heartily.

"But when I was talking about having my orgasms denied by Naomi, and when you discussed being nailed to the board, your cock was very hard, Miles.

Maybe your true nature is indeed to be submissive."

Skyler looked questioningly at me and said, "I know it's difficult to do humiliating stuff, but you're doing it for your Mistress, Miles. Think of how generous that is."

At that moment, Mike came in the house, sweaty from playing in his Friday night softball league. He took one look at us and brayed in laughter.

We did look ridiculous naked on the couch and tethered together by the ridiculous chain on our balls.

Skyler blushed, as did I...but then Sky looked up at Mike and asked, "Is there anything we can do to be of service to you, Master?"

"Are you kidding, faggot?" Mike asked in amazement.

"No, Mistress Naomi and Mistress Gretchen ordered us to be of service while they're gone this weekend, and we'd like to be as helpful as possible." Sky said.

What the hell is he thinking? Jesus, man, don't speak for me! But I didn't say anything.

Mike grinned, and pulled his pants down. "You can suck my dick, if you want to...I've been all excited by the girl who's pitching for the Treadway Electronics company team."

And with that Sky got up and began walking towards Mike, and I had to follow, as my balls were trapped in the damn ring.

I was just going to sit by and pretend I didn't notice what was going on, but Skyler tapped me on the shoulder.

"What do you think your Mistress would really like for you to do? Wouldn't it be nice to have Mike report that we kissed and licked his dick together, like porn stars do in those films?"

And something changed in me...it was amazing! As if in a dream, I sank to my knees, and Skyler and I began kissing and licking the sides of Mike's huge cock.

After a few minutes, Skyler paused briefly and removed his upper dental plate. "This gives him a smoother ride." Sky explained.

"That's great, do my balls, Miles, while this other homo licks the tip, willya?" Mike asked with his eyes closed, no doubt imagining the hottie pitcher from Treadway Electronics.

I knelt down further, putting my head just under Mike's scrotum, and gently took it into my mouth, trying not to make a face.

I tried to think of how hot Gretchen was, and how pleased she would be that I was being of good service, as I rolled Mike's balls around in my mouth.

Skyler was slurping Mike's cock like a demon, running his head back and forth on it, and soon Mike grabbed Sky's ears and began shoving the cock in and out of Sky's mouth, and amazingly, Skyler didn't choke or cough!

Horrible to admit it, but Skyler must have extensive experience in cocksucking, I thought as I continued to juice Mike's testicles up with my spit.

After about twenty minutes of this, Mike gasped and shot his load into Skyler's mouth.

Mike grunted as Sky cleaned him off with his tongue, and I thought that might be it....

"Do you want us to cook you lunch, Master?" Skyler asked, which irritated me a bit. Must he volunteer my services?

But I was starting to see Sky's way of thinking. Despite Skyler's sadness about his slave state, there was a serene acceptance in his eyes that I envied.

"You know, I want another blowjob, I want to cum again, fast!" Mike said, and snapped his fingers.

And back we went to work, but this time Mike was flagging, and though Sky really licked and sucked that bad boy, nothing was happening.

"What's wrong?" Mike asked, enraged. "Why can't you get me off?"

"P-please just give me time, Master Mike." Skyler said desperately, as he opened his mouth wider to receive more of Mike's cock.

But Mike couldn't cum again, and inevitably he accused Skyler and I of malingering, and took off his belt.

WHACK! WHACK! WHACK!

We each got about thirty across our backsides and our cocks, and Mike left us crying on the floor of the living room.

Skyler blew his nose after about twenty minutes. "But this is worth it, Miles. I know you feel that we are being treated unfairly...but we're slaves. This is our lot in life."

Suddenly, Sky motioned for me to get up. "I had too much beer and I have to go to the bathroom."

We walked together to the bathroom, our chain swinging between us. But as Sky got there, he tapped his chastity tube, and groaned.

"Oh no...this is bad." Skyler said, with an aggreived look on his face. "Naomi didn't unlock the pee hole. I can't pee until she gets back."

My jaw dropped as I gazed at him.

"You see," Skyler explained, as he began shifting from one leg to the other, his bladder obviously bothering him,

"...There are two levels to my chastity. I haven't had an orgasm in many, many months, but Mistress Naomi also regulates when I am allowed to go to the bathroom. She often forbids me to go as punishment."

"Of course you're joking, man." I said in disbelief. "You can't go to the bathroom without her permission?"

"Well, it's part of Naomi's total control of me." Skyler said, as he began walking about restlessly, dragging me along by the crotch.

"Sometimes it's worse, she makes me write lines, like five thousand times 'I will be more punctual arriving home' or 'I will remember to clean the bathroom daily' and she'll leave the pee hole locked until I complete at least half the sentences."

Skyler held his stomach and shook his head.

"Other times she'll make me jump around, begging to pee while her boyfriends laugh at me, and hit me with belts, trying to get me to wet myself. It can be quite traumatic, Miles."

"Could...could you not drag me around like this?" I asked as Skyler began doing a little dance. He was holding his crotch and moaning. "It really isn't my fault that you drank all that beer."

Skyler dropped to his knees, gritting his teeth, and of course I had to sit down as well. He looked quite unhappy.

"Perhaps we can go down to the workshop and find something to break into that chastity device...or just drill a hole, you know."

I was nervous. What if his bladder exploded, or he had, God forbid, a urinary tract infection?

"No, no...Naomi would make my life hell if I violated her Iron Maiden." Skyler said, tapping the chastity device lovingly.

I shook my head. I had been through so much in my life--various therapies, traveling the world wearing a knapsack, some time in a motorcycle gang (weekends only, of course).

I'd lived in a commune, managed a bar, volunteered on a rescue squad, tried four different religions, Lifespring, the Peace Corps, the Hare Krishnas, transcedental meditation, working in political campaigns and martial arts.

I'd run an underground newspaper, surfed competitively, and once been a rodeo clown.

But this was really something new! What the hell was this BDSM nonsense?

I was attached by the balls to a right-wing disc jockey nutcase who wasn't allowed to pee and there was no way out!

"I just have to be strong." Sky said, his hips shaking.

"It's been longer than this, she locked it last night, and I haven't drank that much. Once she made me wait eighteen hours."

Sky pushed his legs together like a girl, and held his face in his hands. Suddenly there was a stench, and I looked down.

Pee was squirting out of the sides of the chastity device, and all over Grandmother's 18th century Beauvais carpet.

"Wait, get up!" I screamed. "At least stand in the bath tub, won't you?"

I got up and ran away from the growing piss puddle, but of course the chain pulled me back and I fell down, right in the mess!

"Oh, Miss Naomi will be so disappointed in me for soiling myself" Skyler said with a trembling lower lip.

"I'm such a bad boy..."

Gretchen laughed her ass off about this when I recounted things on Sunday night.

It had been quite unpleasant sharing the weekend with the piss soaked Skyler, even after I'd gotten him in the shower, because of course he had to pee again and again.

And he always refused to stand in the bathtub because he was trying to "Be strong" for Mistress Naomi.

"And it would be like using birth control when you are trying to abstain from sex for Christian reasons...just planning to fail."

I didn't understand this, all I knew was there were repulsive little urine puddles all over my house!

When Mike came back upstairs, he tried to solve the problem by holding our heads over the piss and having us suck it up, but that could only do so much good...

So he'd made us sleep in the garage where we couldn't do much more harm. I begged him to sever the chain between us, but of course Mike couldn't do that...

"The girls would be so pissed at me" he had said with a grin.

Skyler had been locked in closets and in the trunk of Naomi's car, and once in a cedar chest, and so being banished naked to the unheated garage, even in the middle of March, wasn't that big a deal to him.

But the good news was, as I told my lovely wife, that I had come around to my submissiveness....I was ready!

And for the first time in years, Gretchen gave me a beautiful smile.

Shortly after this revelation, I was outfitted for a chastity device, an "Iron Maiden" very much like the one that Skyler wore.