Miless Conundrums Ch 07

Pauline looked at me, reproaching me with her eyes for being such a baby...and I felt badly about it.

I gritted my teeth, and stared at her, and once again she lifted the switch. WHACK!

The clamp fell off, but I had been focusing on her breasts, and so it didn't hurt as much as it could have.

"Good boy" Pauline said encouragingly. "Now we'll try the other one."

WHACK!

This one was more painful, but I bit the inside of my cheek, and watched in silence as the clothespin hit the floor.

"What a good little trooper" Pauline said, kissing me deeply. "Now we'll do the penis pins, okay?"

By the time all the clothespins were knocked off my penis (and Pauline had to hit a couple of them twice to get them all off) I wasn't doing well...

Repeatedly swatting at my scrotum certainly was one way to get my attention and fully weaken me...it was tough!

Finally, Pauline stopped with the switch.

"You are doing much, much better, Miles" Pauline said, and she gave me another kiss. God, was she hot!

"Now I'm going to give you dildo training." Pauline went to the drawer again and when she came back, she had a long black dildo strapped on her waist.

"Now bend over and spread your cheeks, honey." Pauline said in a friendly way. "After you get good at this, it'll be no time until you can get the real thing up your ass!"

I wasn't sure what she meant by that, but I bent over and pulled my butt apart, and she pushed the rubber thing against my anus.

The pain was intense, but I tried to stay still. Pauline went and got some lube and put it on the dildo and came back.

I closed my eyes...suddenly I felt as if my anus was being ripped apart! Pauline grabbed my hips and thrusted, and I squealed like a pig.

"That's a good little bitch" Pauline said as she began jamming the dildo in and out of my rectum. "I've deflowered your pussy, sweet child"

I was in unbelievable agony. "Really, Pauline, this is (oof) just too (oof) much for (oof) me, dear!"

Pauline reached around and began pulling my cock as she slammed the dildo again and again in my butt.

"No, this is good for you, honey...Learn to take the dick, and you'll be a sister. If you get good and get bigger and bigger dicks, eventually you'll be incontinent, but a smooth ride!"

I began sobbing with the intense pain to my schpincter, but Pauline gripped my hips with hands of steel and kept jamming her dildo in my butt so that I imagined sparks flying, it was so bad...

Finally she pulled out, and I collapsed, exhausted.

"No, no...you're not done yet" Pauline said severely. "You still have to do clean up!"

"Clean-up?" I asked faintly.

Pauline marched around to face me, the dildo, now covered in shit and blood, wagging from her hips.

"Lick it off, kiddo...clean this thing now!" Pauline moved closer, and I backed up, fast.

"No, no...Pauline, that's not sanitary!" I protested loudly. "I mean, it's great to go through this whole thing,but you could get me sick!"

Pauline looked at me with her sultry eyes. "Honey, if you do this for me, Pauline will give you a big reward."

Within a moment I was sucking and licking the shit and blood off the dildo. I cleaned it completely.

"Now, go wash your face in the bathroom over there, and Scope your breath, and come back for some lovin'" Pauline said sexily.

I completely got all the horrible blood and fecal matter off my face and out of my mouth, and rushed back to her, quite excited. She patted the couch, and I sat next to her, and she jumped in my lap and we kissed madly.

I played with her breasts, and kissed and suckled them...they seemed rather hard for breasts, but I didn't mind, as they were beautiful.

I reached down to touch Pauline's nether area. It felt a little odd.

"Be careful, darling. I just had my vaginoplasty done...it's brand new, you know!"

My body felt rather cold, and I drew my hand back from Pauline's crotch. "Your what?" I asked delicately.

Pauline smiled at me..."That's the part I didn't mention. I used to be a guy, but Master Nash found the woman in me, and I had an operation done...it's changed my entire life!"

After that revolting interaction with Pauline, or Paul, or whatever it was, I was very turned off of the submissive lifestyle, but there was no stopping Gretchen.

The next day, Gretchen sat me down and began running down the way things were to be.

"The first thing is," Gretchen said, looking at me intensely,

"I don't want any more bullshit demands from you about sex. I am tired of having to brush off your disgusting passes.

It seems like that's all you think about any more, and I just don't feel that way about you. I don't even want you looking at my naked body most of the time."

Gretchen was wearing a pale pink top, quite snug around her breasts, and faded jeans. She was quite enticing.

"Not...not at all?" I asked, my eyes feeling moist. "You don't want me touching you or seeing you naked at all?"

Gretchen sighed and looked out the window. "Maybe sometimes if you can follow a few rules, but it's going to be my way or nothing."

I looked at her pleadingly. "I...I understand. I've been talking with Pauline and I want to try harder to make you happy."

Gretchen moved a little closer to me. She unzipped my pants and pulled my penis out, and began stroking it, as her full lips whispered in my ear.

"The first problem is with this little Willy of yours. It just wants to be happy. It has no interest in my happiness at all...it dominates the household, Miles."

By now my penis was rock hard and poking out of the zipper, and Gretchen was stroking faster and faster.

Oh, it felt so good, and I couldn't believe her mood had changed so fast. I watched her beautiful full breasts heave in the pale pink top as she ran her long burgundy nails up and down my sweating shaft.

"Does it feel good honey?" Gretchen asked in a breathless voice. "I know it's been a while since you had a spurt, right?"

"Yes-yes, it feels wonderful, Gretchen." I said. "I-I love the feeling, in fact."

"I understand that your Willy likes to feel good" Gretchen said, tickling the underside of my glans

"That's perfectly normal, Miles and I don't think there's anything wrong with that, but the constant demands are difficult for your Princess here."

Gretchen pursed her lips at me, and tickled my scrotum, and I began gasping...

I could feel the backed up semen slowly coming up. I hadn't cum since I'd rubbed my dick on the garage floor when my hands were cuffed...

Oh, I wanted to so badly!

Gretchen stuck her tongue in my ear and rubbed her breast against my arm, and I became quite congested, crotch wise.

"What I'm trying to tell you honey is if your Willy keeps trying to be the Boss of you..."

Suddenly Gretchen pulled my zipper up so it caught in my erection and I screamed.

Gretchen looked coldly at me. "If your Willy is the boss, I don't want to be, get it? You have to choose between us."

As I sat there with my penis bleeding into the zipper, Gretchen leaned down and took one of her spike heels off, and began tapping it in her hand.

"See, you forgot about everything I was saying, just because I was playing with your ridiculous dick here."

THONK!

I screamed. Gretchen had just whacked her high heel on my penis. She looked at me contemptously, but at the same time began stroking my dick again.

"A normal man would put his wife first, put her on a pedestal, and not be constantly plotting for when he gets to cum again.

I think all you think about is sticking your goddam dick in me...is that right?"

"Um, no..no, I love you." I said, but of course I was staring down at her painted nails playing with my now purple cock.

Gretchen sighed and shook her head. She lifted the high heel again

THONK! WHONK! STAB!

Again and again the heel pounded into my shaft, until my cock became very small. It was still caught in the damn zipper, and of course this didn't help much.

After this, I really tried to get with it. I did even more of the housework, and when we went to bed, I kept my tongue busy between Gretchen's thighs.

But it was a real challenge--she was sick of what she called my "bullshit" and we went to counseling sessions with Master Nash.

This was especially humiliating--having a man dealing with my therapy...

The problem was of course, that Master Nash didn't look at things objectively at all--we just discussed "my problem".

It mirrored much more a teacher-parent conference about an errant teenager than any sort of marriage counseling.

"And I'm just sure he's still masturbating" Gretchen said one afternoon, as we sat in Nash's living room.

"Miles is so furtive around the house, and once I found a Kleenex that was really sticky. It's a disgusting habit."

"What's that about, Miles?" Master Nash asked me. "Are you participating in that babyish, adolescent habit of onanism?"

I looked at Nash in irritation. He sat there, dressed in black turtleneck and jeans, just so fucking pleased with himself.

"Well, I don't like masturbation" I said.

"But Gretchen turns away my offers of sex when we're in the bedroom. Except for oral sex, which I perform on her, I get no release."

Gretchen looked at Nash with a "Didn't I tell you?" gaze.

Nash leaned over and looked at me steadily. "Your problem is that it's all about you. 'I get no release'

Did it ever occur to you that with your sex desires unfulfilled for just a little time, you could be of greater service to your wife? That you'd be less lazy and self-centered?"

Nash sat back, scratching his chin as he looked at me dubiously. "I just don't see a lot of hope for this marriage unless you stop masturbating, Miles.

Until you're ready to hold in that crucial energy, your interest in your wife's happiness is so diminished.

It's been my experience that the husband is most focused on his wife when she appears the most beautiful and sexually attractive to him...and that's when he's the horniest!"

Gretchen and Nash laughed, and I sat there like a log.

"And of course you should fuel your sexual interests towards pleasing your wife." Nash said earnestly.

"A sexually unsatisfied woman is usually frustrated and irritable, but a horny man is devoted and single minded, Miles.

And of course you'll get your occasional treats, but you need to earn them."

Nash sat back, and lit a cigarette. I had protested his smoking in our sessions early on, but of course that was no use.

"My slave Pauline, in her previous incarnation as Paul was so penis focused, that we inevitably had to just remove the penis and testicles and throw them away." Miles puffed at the Marlboro. "

I'd hate to have to have that solution for you, Miles."

I just sat there in horror. What the hell was he talking about?

Gretchen shook her head. "No, if we got rid of his junk, he'd lose all interest in pleasing me. You think he cares about me as a person at all?"

To my relief, Nash agreed with her. "You're right, of course, incentive is everything."

"We've got to keep you horny and fascinated with your wife, without spooging...and this will keep you from complaining all the time, as well." Nash said.

"Gretchen tells me that you object to her having a social life."

"A social life?" I exploded. "I object to her fucking around, and sleeping with all my friends, that's all."

Nash grinned and Gretchen giggled. "You've got to let go of Gretchen if you want to enjoy her, Miles.

Part of this idea that you have sole right to her body is due to giving yourself orgasms all the time."

Because of course, I thought, she won't give me any.

"You've got to see Gretchen on a pedestal, and stop thinking of yourself as the big macho man." Miles said.

"He's hopeless I think." Gretchen said. "It's like living with Stanley Kowalski or something."

"If it's true that I am so arrogant," I asked puzzledly, "What can change that?"

"As you go without orgasms for an extended period of time, Miles" Nash said kindly,

"You will begin to see Gretchen as a princess to be worshipped. Isn't she beautiful?"

I looked at Gretchen, large breasts resplendent in a tight black crop top with double cupid hearts and a flying skull and crossbones design emblazoned on it.

She was also wearing metallic black shorts that barely covered her privates, and her stockings--fishnet seamed thigh highs with Satin Skull Print Bows.

And of course four inch high heels.

Gretchen looked at me, pursed her glossed lips and rolled her eyes.

"Yes, she's very beautiful. She's the ultimate woman." I said.

Nash grinned. "And you want to hold on to her! You're an average doofus, and you've gotten this beautiful hottie...give up masturbation."

Nash stubbed out his cigarette. "Or, better than that, masturbate, but don't cum.

There's nothing wrong with getting yourself all jazzed up, thinking of serving your beautiful girl."

"B-but it's so hard not to cum." I protested. "I get so excited, and then there's no turning back."

"He's like a fourteen year old retard." Gretchen said implacably.

Tell you what, Miles. I'm going to help you." Nash said. "Take off your pants and shorts now."

"What?" I didn't want to go through being humiliated as I'd been before in this house. "I don't think--"

Nash's voice came firmer. "Now, Miles. Strip 'em off!"

I got up and sighed heavily, and unzipped my pants and stepped out of them as well as my tighty whities.

"Now," Nash said encouragingly, "I want you to stand in front of Gretchen and masturbate yourself.

And Gretchen, you give him a little show...make the boy excited!"

As I pumped my cock, Gretchen began casually squeezing her breasts through the skull-and bones top, and licking her lips at me.

I rubbed and pulled my now several weeks denied shaft and my legs trembled as I watched my beautiful wife.

Gretchen pulled her top up and began squeezing and toying with her nipples, and gyrating her waist. "You like it, lover?" she said with a husky voice.

I had completely forgotten Nash by now. I was staring at Gretchen and pumping my cock for all it was worth.

I kept pounding on my cock as Gretchen did a strip dance in front of me.

Gretchen wiggled her breasts at me, and then covered them up again, and reached into her metallic black shorts and moved her hand around.

Gretchen ran her hands over her tits and stood up and squeezed her ass and slapped it, and jiggled herself again.

She reached into her glass of ginger ale and pulled out a piece of ice.

Pulling up her top again, she jiggled her bare breasts at me, and began rubbing the ice against her nipples until they were hard and thick.

I slammed my hand up and down my cock as I watched my beautiful wife pull off her shorts and then step out of her panties.

She sniffed them and then rubbed them on my face as I jerked my cock more and more, faster and faster.

Gretchen reached down to her nearly shaved crotch (which she'd shaved for Tom, not me) and used her index finger to play with her clitoris.

She caressed the hood and I could see that she was beginning to get wet.

As I stared with slack jaw, Gretchen pulled her fingers out and licked her wet fingers.

I began shaking all over and I was close to orgasm, my tongue was between my teeth. Suddenly, I heard Nash's fingers snap.

"That's enough, Miles. Take your hand off your dick!"

But I couldn't, I was too excited, I kept pumping and staring at Gretchen, who had stopped in disgust and began dressing.

Suddenly, just before I was about to cum, Nash slapped my hand away from my cock, and then slapped my face, hard.

"I told you to take your hands off your cock and you didn't!" Nash said angrily. "Put your hands behind your back and get on your knees!"

Sullenly, I obeyed him. My cock was now poking straight up, and was purple with my efforts.

Gretchen was fully dressed again, and sitting on the couch with one stockinged leg across the other.

Nash went to the dresser and brought a long yellow cane over.

"This cane is made of lexan, which is a durable thermoplastic. Now we'll see if you can control yourself, Miles."

Nash looked at me severely. "Now I want you to begin masturbating slowly. Not too fast."

I began tentatively playing with my cock as Gretchen popped her gum and looked very bored.

Gradually I speeded up, keeping an anxious eye on Nash and his lexan cane.

Gretchen flashed her nipples at me and I began jerking faster, and panting a little bit.

"Now stop, Miles, hands behind your back!" Nash's voice came suddenly, and I stopped but not fast enough.

THWACK! The cane hit my hand twice and after I let go of my cock, it snapped the head of my cock three times.

Nash shook his head, as I alternated between sucking my injured hand and putting my hands behind my back.

"You've got too slow a response time, Miles. You've got to learn to hold back when I tell you to."

"Ugh." Gretchen said as she looked at me kneeling there.

"What's wrong?" Nash asked, waving the lexan cane about.

"Oh, I just can't stand looking at his puny cock. It's like a Vienna sausage, you know?" Gretchen looked appealingly at Nash.

Nash nodded understandingly. "Well, it's not for your pleasure, honey. Miles's tongue is what is to work on you down there."

I couldn't understand it. My cock was at its hardest, and at one time, Gretchen had moaned and screamed when I'd entered her.

"The big problem with this penis of Miles's is that he can't control it.

It won't stop being erect long enough for him to calm down." Nash said disapprovingly.

"It's like living with a fuckin' dog." Gretchen said looking at my poor cock. She was so hot, though, that my cock lengthened.

"What's got to happen, is Miles must learn to stop his passion on a dime." Nash said.

"Why don't we try a little experiment? Gretchen, play with Miles's penis a bit."

Gretchen sighed and leaned over to take my penis in her manicured fingers.

I was quite enjoying the shot of her cleavage when suddenly I felt Nash cuffing my hands behind my back.

Gretchen began stroking and pulling my hard cock, mumbling about how she felt as if she was masturbating a ballpoint pen.

But despite her comments, Gretchen's beautiful soft fingers were certainly getting me to the point of ecstasy once again! I began moaning and gasping as she tickled my frenulum.

"Now, Miles..." came Nash's IRRITATING voice, "Go limp!"

What the hell was he talking about? Gretchen let go of my cock, and it bounced around as I struggled to get loose of the cuffs.

SNAP! TWACK! SLASH! The lexan cane came down on my rock hard cock again and again until it resembled a limp rag.

I was screaming and crying, and I felt as if my crotch had been hit by nuclear waste. Nash and Gretchen exchanged a knowing smile.

"Now then, you see the problem here?" Nash said disapprovingly. "You have no control over your cock at all, and you really seem to need some kind of training."

About a week later, we came back for another session, and Nash said he had some good news for us.

"I have another couple who is much more advanced in their training, and hopefully they can be an example to you."

Nash touched a bell, and in came a man and a woman.

The man was in his fifties, and had steel gray hair, and the woman looked to be about Gretchen's age, in her thirties.

While Gretchen has short hair, this woman had long blonde hair tied up in a severe bun, and she was full breasted.

She looked a bit like a cross between Courtney Love and Brigitte Nielsen, with a bit of Cyndi Lauper thrown in.

"Miles and Gretchen, this is Naomi and Skyler. I have been working with them for more than a year now."

After shaking hands, Gretchen and Nash and I sat back down, but Naomi looked coldly at Skyler. "Prepare yourself."