Miles's Conundrums Ch. 06

Story Info
More and more for Miles!
3.8k words
4.27
23.5k
3
0

Part 6 of the 9 part series

Updated 10/18/2022
Created 07/08/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

A few days later, Gretchen told me that she'd made an appointment for us with a therapist. "We really have stuff to discuss, Milesey."

"What-what sort of therapist is he?" I asked nervously. "Are we going back to Dr.Strazewski again?"

He had been the marriage counselor who had charged us an arm and a leg to "communicate" more.

"No, Strazewski was air headed windbag closet case. Nash is much more proactive." Gretchen leaned back in her chair, licking her lips. "Yes, he is."

Peculiarly, Nash did not have an office downtown as most psychologists do, just a modest suburban house, and once on the porch, we rang the bell.

The door opened and a dark haired girl with full lips in a bathrobe looked out. "May I help you?"

"Yes, we're here to see Master Nash." Gretchen said pleasantly.

Master Nash?

The girl let us in and shut the door, locking it behind her.

"You're Mistress Gretchen?" The girl, although actually taller than Gretchen (and myself) seemed to look up at Gretchen as if she were a child looking up at Mom.

"I'm Gretchen Unowicz, that's right, and this is my husband Miles." Gretchen smiled at the girl, who then behaved astonishingly.

She took off her robe, and dropped to her knees. Naked and with quite a set of big breasts, the girl looked up at Gretchen appealingly.

"Mistress Gretchen, I am Master Nash's worthless slave Pauline. Before I show you to the Master's quarters, will you be needing any refreshment?"

Gretchen gave me a "Now this is how I like to be treated" look before gazing back down at Pauline. "No, sweetheart, I'm all right."

Pauline rose to her feet and escorted us to a small room off the living room. "This is Master's Parlor" she said "Please make yourselves comfortable."

Pauline looked earnestly into Gretchen's eyes. "Mrs. Unowicz, Master Nash wanted me to tell you that if you have any irritated feelings, it's helpful to get them out of your system before the session."

Gretchen smiled gently. "I-I'm okay, Pauline, really." Gretchen looked at me and back at Pauline. "But don't you want to put your clothes on honey?"

Pauline beamed at Gretchen and shook her head no.

Why wasn't Pauline looking at or speaking to me? I was irritated as all hell.

Pauline smiled and touched Gretchen's hand.

"N-no really, Miss Gretchen. Anything, any tensions, if anyone cut you off in traffic today, whatever might be going on with you could be toxic.

Is there anything?"

"Um, well, I guess there have been minor irritations," Gretchen acknowledged. "I mean, I'm here, anyway, why?"

Pauline bowed her beautiful dark head and then walked over to a table where there was a long switch made of hazel or hickory.

Pauline brought the switch over to Gretchen. "Mrs. Unowicz--Mistress Gretchen, you can take your annoyances out on me.

Please whip my breasts until you feel less tense, ma'am...please."

Gretchen took the switch gingerly in her hand and tapped it. "Pauline, I don't want to hurt you, you've done nothing to me except be a good little hostess--"

Pauline touched Gretchen's arm. "P-please. Or Master Nash will think I've been neglecting you. It'll be good for us both."

Seeing Gretchen's assent, Pauline backed up a bit and put her hands behind her back, arching her back and jutting out her beautiful breasts.

Gretchen took the switch and lightly swatted Pauline on her right breast, a swat that would have made me squeal, but the girl didn't make a move.

"Mistress Gretchen, I'm sure you can do better than that," Pauline said, and smiled to hide her impudence.

Gretchen smiled herself, and then held the switch back

WHACK! WHACK! THWACK! SNAP!

Long red marks began appearing on Pauline's beautiful white breasts, but she didn't utter a sound.

Gretchen looked at me in contempt, for we both knew how loudly I would have been screaming!

Gretchen lifted her arm and brought the switch across Pauline's breasts about six more times, and other than one swift intake of breath, the girl said nothing.

Suddenly, it seemed as if Gretchen's personality was changing. There was a fire in her eyes!

"Pauline, grab your ankles, I want to make that little derriere of yours shake a bit!" Gretchen said with teeth clenched.

Pauline bent over and grabbed her ankles and Gretchen sidled behind her and worked her over with the switch until the girl finally cried out.

"Okay, you little smartass, you can get up now!" Gretchen said, tossing the switch across the room.

Pauline got up, and there were a few tears, but she was one tough cookie. She took Gretchen's hand and kissed it.

"Master Nash will be with you shortly." she said, and limped out of the room with as much dignity as possible.

We then sat on a couch and Pauline bowed deeply, and retired from the room.

I was somewhat aroused by Pauline, but I remonstrated with Gretchen.

"Look here, this Nash fellow can't be licensed if he has women running around in the nude, much less having you hit them...what sort of shrink is he?"

Gretchen snorted. "Nash isn't a shrink, Miles...he's a dynamic mender of marriages. His academic qualifications I know nothing about."

"That's because I don't have any!" came a masculine laugh. We looked up and a short, balding fellow with tortoiseshell glasses was walking in the room.

"No, I never even finished high school--it was that damn geometry!" Master Nash sat down on a Barcalounger facing our couch. "That and the assemblies, which were far too boring."

Just as we were going to start, Pauline came in again with some tea, which she put on the coffee table. Nash smiled at her, and looked at Gretchen.

"Did Pauline inform you about getting your aggressions out?"

Gretchen nodded enthusiastically. "She takes pain a lot better than some people I know" I blushed, of course.

"Did she give you the switch and the nettles to use on her?" Nash asked eagerly.

Pauline all of a sudden began shaking the teacups nervously.

"No, nettles? No...Just the switch, but that was good enough." Gretchen said cheerfully.

Nash looked up at Pauline through his little round spectacles. "Well now, Pauline, you disobeyed Master, didn't you?"

Pauline's face grew dead white. "I-I'm sorry, Master Nash I-I'm terrified of the nettles, they're so painful!"

I couldn't understand what a beautiful girl like Pauline was doing hanging around a dork like this Master Nash.

Nash was far geekier than I---skinny arms and legs AND a pot belly. But there was confidence in his manner, for sure.

"Well, I'm not going to whip you with nettles, though you certainly deserve it for disobeying me." Nash said pleasantly.

Pauline smiled hesitatingly. "Thank you, Master, I'll be better next--"

"Go get me the cactus branches, honey." Nash said, and we all watched Pauline's face fall into her hands, and she began sobbing.

But when she looked up at Nash, his own face was implacable. Pauline cried harder and ran from the room.

A few moments later, she came back with a small plant with bright green leaves with nasty thorns sticking out of each leaf.

"Ah yes, my favorites" Nash said happily "Euphorbia grandicornis , my favorite kind of cactus."

Nash snipped off a cactus leaf and motioned the weeping Pauline over.

I expected a horrible punishment, but it was just two quick swipes of Nash's surprisingly strong hands across Pauline's full breasts.

Pauline stood normally for a moment, and then bent over, grabbing her breasts and wailing. Nash snapped his fingers.

Pauline grabbed a small sofa cushion and bit it.

"I am training her to not make noise, but it isn't easy you know" Nash said. "Pauline is getting better at being a pain recipient, but it's one day at a time."

Finally Pauline took the tea, the cactus and her aching breasts away, and we got down to business.

I figured, like most counseling sessions, both husband and wife would tell their sides of the story and there would be mediation, but I figured wrong.

"So! Gretchen." Nash said, smiling at my wife. "What can we do to improve Miles? Did you employ any of my tough love suggestions?"

Gretchen nodded her head. "I've whipped him, humiliated him, and dressed him in drag, but he's still a controlling asshole.

He thinks he can tell everyone how to live, and when he's not putting his filthy hands all over me, he's playing with himself. It's disgusting!"

Nash looked at me and shook his head. "Guys like you make me sick." he said depressedly. "You just ruin the outlook of cheerful women like our Gretchen."

"What the hell?" I asked, outraged. "You haven't even heard my side of this. And was it you who recommended she put makeup on me? What the--"

Nash stepped up, hopping over the coffee table. He pulled me up by the collar and shook me.

"We don't need to hear your bullshit young man." Nash said, his face close to mine. "Your Mistress and I are trying to save your life here."

I struggled against Miles, who was about a foot shorter than I was, and he reached into my crotch and squeezed, and I fell to my knees, crying.

Miles stepped back and I got up, tears streaming down my cheeks, and a dull pain between my legs.

I sat down on the couch, staring at my belt buckle.

Gretchen didn't seem to care that I had just been assaulted by this stranger.

You'd think she'd be upset, but after all,she'd been encouraged to assault his receptionist so...

All bets were off around here, apparently!

"See how mouthy Miles is?" Gretchen asked Nash with disgust in her tone. "I just can't control him anymore. He's too persnickety."

"I'm not--you're not supposed to be controlling me!" I said angrily. "Who the hell do you think you are, woman?"

Gretchen looked at me and burst into tears.

Nash got up again, and I cringed into the couch, wondering if he was going to assault my crotch again.

But Nash took a piece of chalk out of his pocket and drew a circle about the size of a basketball on the hardwood floor.

"Now, Miles." Nash said in a level voice. "I think Mistress Gretchen and I have had enough of your lip.

Unless you want me to give you the whipping of your life right now, you're going to stand in this circle with your hands on your ankles and say NOTHING until I tell you to."

"Yeah, you can grab your ankles like Pauline did, asshole!" Gretchen spouted snarkily.

I'd had enough. "Go to hell, you quack!"

I'd been a boxer in school, almost made Golden Gloves, and I wouldn't take anything from this idiot.

But as I advanced on him to swing, Nash calmly reached up and grabbed me by the ear.

As I struggled, Nash began shaking my head by the ear until I was quite dizzy.

Nash pointed to the discarded switch that Gretchen had used on Pauline. Gretchen eagerly handed to Nash.

"Now, sir, take down your britches!" Nash let go of my ear, and I was almost shaking in fear and rage...but I found myself fumbling with my zipper!

Nash pointed to the couch and I shuffled over and bent over it, my pants now down at my ankles, along with my undies.

Nash stepped over. "I want you to say after each stroke, 'Master I apologize and will treat Mistress Gretchen with respect.' Every time, Miles!"

The whacks sounded like pistol shots, and didn't feel much better. By the third slash across my exposed cheeks, I could barely make out

"Muh-(sob) Master I apol (gasp)logize and wuh-will (sob) please no more--treat Mis-(sob) tress Gretchen with (Sob) respect!"

After he'd hit me about thirty times, Nash ordered me to strip and stand in the circle.

"I don't think I can bend low enough to grab my ankles." I whined.

Nash laughed and punched me in the stomach, hard. After I nearly split myself in half, he handcuffed my wrists to my ankles.

"Now, Gretchen, why don't we go in the other room and get a drink and have a nice relaxing talk?" Nash smiled at my wife.

He rang a bell, and by just barely being able to look up from my horrible crouched form, I could see Pauline come in.

"Pauline, why don't you take this switch and give our Milesey a lick if he steps out of the circle, though of course he can't step much of anywhere?"

Gretchen and Miles went into the other room, and Pauline, gorgeous as she was, sat down and began watching television.

A few moments later, I stumbled, just a bit, and my toe came outside the circle.

Pauline of course jumped up and WHACK WHACK! got me back inside the circle...and it went on and on!

I began getting terribly cramped, being bent over and cuffed like that, but I dared not mention this to Pauline.

At some point she got bored with "The View" and turned to talk with me.

"What's your problem, dude?" Pauline asked curiously. "Are you having problems with being a submissive?"

I tried to look up at her, but it was almost impossible.

"Well, I guess I was the one to introduce my wife to BDSM, and I like it as a fantasy, but not as a 24/7 thing."

I tried to move, but almost fell over.

"Gretchen's begun taking advantage, getting my friends to humiliate me, cheating on me with my friends, and being a real bitch."

Pauline waved the switch warningly. "No verbal abuse of the Mistress there, bub. Look, don't you see the freedom in being a happy submissive?"

I just sighed. I didn't know what she meant by "freedom" as I was cuffed to my ankles just then.

Pauline smiled. "You must have some desire to be a submissive if you haven't left your wife after she's put you through all this. Am I wrong? Don't you get off on it? Your cock is hard enough."

I looked at my cock, and indeed it was hard.

"Yes, it does arouse me, but the fantasy is much easier than the reality, Pauline. I miss the normal life of being my own man."

Pauline snorted. "The normal life is over-rated, Miles.

Before I met Nash I was a martini-swilling, three pack-a day smoker as well as being a bulemic and a self-mutilating cutter.

I'd been in therapy for fifteen years, and had had a deviated septum operation because of cocaine abuse, and an ulcer.

I was honorary vice president of my father's chain of luggage stores, and made $300,000 a year and I was miserable."

Pauline sighed, no doubt thinking of the old days. "I met Master Nash through a BDSM club and my life is wonderful now...

I let Master make all my decisions, and my only responsibility is doing as he tells me to and being the best submissive I can be...

And I'm incredibly happy...my life is finally controlled.

From being a spoiled brat who had been kicked out of seven prep schools, I am now mentally healthy, unselfish and considerate of others...and I laugh!"

I wanted to argue with Pauline that her way of life was mentally ill,but I was not in the position to argue much of anything!

"Miles, you should try to be a good slaveboy" Pauline said earnestly.

"Your wife knows what's best for you, and with Master Nash's help, you'll have one hell of a life!"

"B-but Pauline," I protested, "I just can't take all this punishment...she hits me so hard, and...."

Pauline snickered. "And you're a little crybaby?

I can just imagine. I was a wailer too when Master Nash took me under his wing...but I've learned to control myself."

Pauline got up and brought the switch to where my butt was sticking out, as my hands were of course cuffed to my ankles.

"I'm going to teach you not to scream. Can you take a few? Let's see!"

I noted bitterly that Pauline was not waiting for me to answer...

She lifted the switch. WHACK! THWAP! SMACK!

"Now, was that so bad?" Pauline asked considerately.

"Oh, no." I said between my teeth. "It's peachy."

Pauline whacked my butt a few more times and then got up and went out of the room. When she returned, she had the key to my handcuffs.

"I'm unlocking you, because Master Nash said I can train you to take pain if I want...he might give me an orgasm if I do a good job."

After I was unlocked, Pauline instructed me to stand in front of her as she sat on the couch. She had come up with a school ruler, an evil looking metal one.

Pauline began stroking my cock after oiling her palm, and was she good at it!

"There we go baby...look how hard that big boy is getting."

Pauline's voice was as smooth as silk, and she tickled the underside of my cock, and I began moaning and panting.

My penis, in Pauline's manicured fingers was growing into an MX missile!

"Niiice and big, what a big boy you've got there." Pauline said with satisfaction.

"Now for our little test. Put your hands behind your head...no cuffs. Now hold on."

Pauline lifted the metal ruler SMACK! SLASH! SCRACK!

The metal ruler bounced and slashed my poor cock until it felt like it had been hit by particularly cruel lightning

Immediately, I grabbed at my painful, flailing erection, and fell to my knees screaming and crying.

"No no, little man." Pauline said with extreme patience. "Back up on our pins now, and we'll try again...."

I got up, tears blearing my eyes, and still rubbing my savaged cock. "Oh p-please don't do that again, Pauline."

"What's wrong, baby?" Pauline asked affectionately. "Don't you want to learn to be a tough little submissive, like me?"

I nodded, wiping my snotty nose, and put my trembling hands behind my head again. Pauline began rubbing and stroking my cock again.

I thought after the initial whipping, that my penis would never erect again,but amazingly, it hardened right up.

"Miles, you have to be a little man now. Don't you want to impress me?" Pauline asked imploringly.

That was it, she put me on my mettle.

Pauline raised the metal ruler, and I closed my eyes.

SMACK! WHACK!

The pain singed my penis like she'd thrown a lit match at it, but I stood my ground and tried not to utter a sound.

WHACK! SNAP! CLONK!

I had to grab my wrist with my hand to keep it locked behind my head, as my cock was in intense pain, and the tip looked as if it were a siren on an ambulance.

SLASH! SMASH! CRASH!

Pauline's voice came. "Good boy, just a little more, be a big man for just a little more, and you'll make Pauline so proud."

SMACK! CRACK! CLAP! WHAP!

I bit my lip until it bled, but emitted no sound whatsoever.

Finally, Pauline stopped with the metal ruler, and clapped her hands.

"What a big, strong fella you are, Miles!" Pauline leaned over and gave me a big smooch.

"That's the kind of sexy slave that will impress Mistress Gretchen!" Pauline looked so pleased and proud.

"So it's over now?" I asked, finally taking my hands down from behind my head.

"Now we have to go a little further." Pauline said, with an encouraging wink.

"Your manhood will really be tested now, Miles, but it'll all be worth it in the end."

Pauline went to a chest of drawers and brought back a bag of clothespins, like I'd not seen since Mother bought her first Maytag.

"Now put those bad hands behind your head again, big boy, the fun's just about to start" Pauline said affectionately.

Pauline opened the spring of one of the clothespins and closed it on my right nipple.

The pain was unbearable. "Oww! Take it off, take it off!" I was jumping up and down, and Pauline thwacked the side of my head with the metal ruler to calm me down.

"I am appalled at your immaturity, Miles." Pauline said severely. "I can't believe you can't take the impact of one little clothespin."

Pauline reached over and stroked my chin in a sweet, loving way. She opened her big brown eyes and possessed me with them.

"Honey, the pain of the clothespin is a sensation you have to welcome. Just let it into your heart, like the good submissive you are."

I closed my eyes tightly and tried to focus away from the incredible pain emanating from my right nipple. It felt as if a dog was biting it, though.

Pauline ruffled my hair with her hand and then put another clothespin on my left nipple, and I began sobbing silently.

12