Miles's Conundrums Ch. 04

As I was finishing up the leaves after my whipping, Gary drove by, and came up to the fence to talk.

He noted the T planks stapled to my cock and the welts on my naked rear end.

At one point Gretchen knocked on the window and waved the quirt threateningly at me.

"She's real high maintenance, dude." was all he could say before leaving me to hurriedly complete my raking.

The rest of the week was really quite hellish...

I did all my chores, all Tom's chores, and Gretchen thought of lots of other things for me to do with the T board locked on my penis.

The worst part was the 200 jumping jacks which hurt my dick, hurt my knees when the T hit them, and once gave me a bloody nose when it flew up. That evening, I was watching Gretchen read her magazine in a beige corset just covering her boobs, and a G string, with scalloped lace-top stockings.

My dick stiffened against the board and the nails really began to hurt. "Mmm..." I gritted my teeth.

Gretchen looked at me. "What's wrong, you're lifting the board with your dick...strong man!"

I looked at her pleadingly. "I can't take this board anymore. Looking at you in that hot outfit is causing my dick a lot of pain, honey!"

Gretchen leaned over and pushed her boobs together in the low cut cleavage and shook them at me, with a sexy pout.

My penis hardened, pulling up the T planks and I bit my lip. Gritting my teeth more, I closed my eyes.

But the board was still grinding into my penis, or vice versa. The sharp pain of the nail brads was excruciating.

I thought about basketball.

"With Chicago nursing a two-point edge late, Perkins nailed a 3-pointer with 14 seconds left to give the Lakers a one-point lead. Scott then added a free throw to give the Lakers a hard-fought 93-91 victory..."

I felt the T board go down a bit. Now it was just back to a dull pain of dragging again. I opened my eyes.

There she was flashing a nipple. The sharp pains returned!

Seeing my distress, Gretchen smiled. "Honey, just because I'm not interested in doing the deed with you, doesn't mean I shouldn't be able to dress in a way that I feel attractive, as a sexually available woman."

I was almost crying now, the pain was so much. Also the planks kept hitting the coffee table as my penis erected.

Baseball.

"Cabrera is is 0-2 with a 7.43 earned runs average--"

I opened my eyes, she flashed me AGAIN.

Mental arithmetic? I was real good at that in junior high. I thought of one I was impressing them with at the water cooler on Thursday.

"Three tracks on a CD have the following times:10:34,6:25,8:07...What is the total time? Seventy-two seconds equals one minute twelve seconds..."

I felt something hit my face, and opened my eyes again. Gretchen had thrown a spitball at me, and flashed her boobs again.

Good thing she wasn't in my classes at school. Thank the Lord for good old single sex St. Bart's Academy.

But Mr. Dean's List got hard AGAIN...oh, the pain.

Gretchen smiled and cocked her head. "This is so good for you, Miles. "

She came over and sat next to me on the couch.

" Miles, the burden of your penis's demands is causing you so much distress that you're realizing what a pain it is for the rest of the household."

Gretchen reached out a finger. "Do you like my manicure, Miles? It's Maybelline Wet Shine polish. It won the Lacquer battle of the drug store nail polishes."

"It's lovely" I managed. She began stroking the shaft of my penis, so cruelly nailed to the T planks.

"You see, Miles, you've got this huge burden. We all feel it."

Gretchen ran her finger up and down the top of my shaft, the bottom being inaccessible because of course of the planks.

" Tom thinks you're going to throw him out of the house because of your jealousy issues..."

Gretchen kissed my ear and began stroking faster, and my cock filled with blood, making the skin around the nails stretch quite painfully.

"I am annoyed at your constant lustful gazing at me and other women." Gretchen toyed with the glans, and I moaned.

"You were looking at the neighbor girl, little Cassidy Delozier, just the other day because she was wearing that silly poplin polka-dot thing."

I thought of Cassidy Delozier in the silly poplin polka-dot thing and the pain became quite insistent.

"Or what about Faye Lookabaugh, she told me at the A&P that you are always staring at her butt." Gretchen began pulling on my foreskin, what little there was of it.

Faye Lookabaugh's butt, twitching in her annoying denim miniskirt, shot through my diseased mind.

"And then you jerk off all the time, and I catch you at it, and I feel so hurt" Gretchen suddenly smacked the tip of my penis hard against the T plank.

"Buh-but honey," I said with tears in my eyes, "You won't let me touch you, except to give you oral sex, and I have needs too."

"You must be joking." Gretchen said, shaking her head. "You think you're supposed to be wasting your seed like that? When the purpose of semen is to propogate the race?"

Gretchen shook her head and looked at me again.

"Miles, when I cum, it's not a waste of anything, but you're supposed to not waste your seed. I think it's in the Bible, no spilling."

I bit my lip. What the hell could I do to convince her!

"But you don't want me to screw you, Gretchen..."

"Not often" she corrected me. "Sometimes, when you behave well, you put me in the mood, admittedly, not often."

Gretchen tickled the end of my glans with a long nail.

"I keep wondering when you'll realize that your lust is just causing you--and me, pain, and weighing us down."

Suddenly Gretchen grabbed my head and pushed it into her cleavage--she hadn't allowed me to do that in YEARS, and my dick went hard so fast that the T square shot straight up.

"I wonder if I could attach a tray to that and have you serve drinks with your hands locked behind your back." she murmured.

I had an image of my hands cuffed behind my back, penis rock hard supporting a tray of Chardonnay glasses for Gretchen and her bitchy little friends.

In my imagination, I would go from girl to girl, and they'd each take a glass off my tray, releasing a little weight each time. And of course making ridiculous comments.

"You should be in some kind of testosterone catering, Miles!"

God, I hope she doesn't do that. Intellectually of course I knew that my penis wasn't strong enough to hold up glasses of wine, but you never knew what Gretchen would do.

Now my face was in Gretchen's glorious mounds...oh she had put some kind of perfume on...my dick was getting harder, attempting to separate itself from the board!

But the nails were locked in, and so there was just the miserable struggle. Suddenly Gretchen pushed my head away and slapped my face.

That helped a bit. My penis went down immediately!

"You just want to mess around with me! You don't respect me as a woman at all!!" Gretchen screamed.

As she said "all", Gretchen slapped the tip of my cock against the board and I howled.

The door opened, and Tom came in, and took a look at the situation.

Gretchen, in her hot little corset and panties, and me, naked with the damn plank nailed to the side-skin of my penis!

"Where have you been?" asked Gretchen pleasantly. You could tell that she just wanted to fuck Tom constantly, the cheating bitch.

But my attitude was why I was in this situation, I had to give up my mysoginistic attitudes, right?

"I just bought some stuff to make chili for Stu's place." said Tom. "He's hosting the poker tonight. Hope you can come, Gretch."

Gretchen smiled. "I'd love to."

Of course he didn't ask me...I was no longer one of the gang.

"So how is Miles's re-education going?" Tom asked quite seriously. "Is he still objectifying you, Gretchen?"

This, coming from an a lust-driven beer drenched idiot who whistled at anything female between the age of twelve and eighty, was just perfect...

And it was sad. Tom and I had always been running buddies before all this started...

We used to go bar hopping in college and as young bachelors, we'd gotten caught cheating on our first wives at about the same time, and done the whole bar scene yet again!

And now he was a viable man, and I was just this "project" for my feminist wife...too much!

Gretchen smiled up at Tom as she began stroking the top of my shaft again. "He just doesn't get it, Tom. He's too focused on me sexually, even with the planks."

Tom scratched his chin, thoughtfully. "Golly. I wonder if the problem is insufficient pain. There might be a way to increase his awareness."

Tom got a napkin and went through his bag and pulled out a bright orange pepper. "This is a habanero pepper. It's too hot to handle without a napkin, and I got it for the chili, but hold on."

Tom went into the kitchen and came back with a rubber glove and some ground up habanero.

"Now, you should probably lock Miles's hands behind his back, you know, Gretch?" Tom said as he put the rubber glove on.

"No, Miles is trying to prove that he can be a better boy, and I'm going to ask him to sit on his hands." Gretchen said sweetly. "Maybe if he handles this well, we can start treating him like a man again, a secure, normal man like you, Tom."

I sat on my hands quickly. I just wanted to get back to the way things were! Tom sat down next to me and with the rubber glove on, began rubbing my dick with the habanero peppers.

And I felt as if my dick was on fire. Truly on fire. And I was about to scream. But Gretchen put a finger to my lips.

"Honey. Stay on your hands and don't scream. Be a man. I like a man who can take his medicine." Gretchen looked quite sincere. "Can you be a man for me?"

Gretchen gave me a big wet kiss and my cock hardened, despite the fact that it felt as if it was being ignited with gasoline.

It was quite hard for me to stay on my hands. My dick was nailed to a plank and was being burned up with habanero peppers.

I had to turn away from Gretchen's kissing mouth and grit my teeth, and my eyes watered.

"Oh, you don't want me to kiss you?" Gretchen said innocently.

"No, no I like it but..." The pain was horrible. Tears were streaming out of my eyes like there was no tomorrow.

It was too much, I jumped off the sofa and ran into the shower, where my plank slammed against the shower wall as I turned on the cold water...

It took forty minutes of cold water before my penis stopped screaming!

Gretchen was terribly disappointed when I came back into the living room, but Tom was upstairs laughing his ass off.

"I just don't think you care about anything but your dick" Gretchen said sadly. "We are going downhill fast as a couple."

I worried that I might lose her to Tom, or just lose her!

But later on that evening, Tom and Gretchen said they had yet another surprise for me. They'd decided to take me to the poker game!

I was cuffed with the Police Handcuffs, and thrown in the back of Tom's van, as the planks made it difficult to sit in our BMW.

When we got to Stu's, there were three strange women there...dressed in hot outfits, and they were obviously strippers.

One was wearing a nurse outfit, another had a snug T-shirt with a heart emblazoned on the front, and it said "Cupid's Slut"

The third was in a bizaare Bumblebee outfit, with tight striped top and huge wings.

I will not go into great detail, but while the poker game went on, the strippers took turns giving me extensive lap dances, and of course they sat on the plank, which was horribly painful...

Gretchen had primed them well with my Platinum Visa card!

Perhaps the worst of the three girls was the one in the Bumblebee costume.

She was really angry at men, I could just tell that, but she was also very cute.

The Bee had very short pixie cut hair with little bangs, and very big boobs...and she knew how to pout.

The Bee sat on the board as I sat on the couch, and moved closer.

Suddenly The Bee pulled down her top to show me full alabaster breasts with rose colored nipples.

"Don't you want to kiss my honeys, douchebag?" The Bee asked this in a husky voice. "C'mon, you can put one of them in your mouth if you like."

I leaned towards her nipple, but the Bee slipped away from me, jumping off the plank and holding the end of the T cross against her stomach.

I kept trying to lean towards her beautiful boobs, but of course I was nailed to the plank, and couldn't really get up off of it, with her holding the end.

"What's wrong, dork?" The Bee asked innocently. "I don't know what kinda stupid asshole you was to let someone nail yer dong to this wood, but you want my boobies?"

The Bee jiggled her breasts at me, and weeping tears of frustration, I tried to lean towards her.

But as I got up, The Bee grabbed the plank and began dancing with it, shaking my dick and balls so I almost fell down.

"C'mon, jerk-off, doncha want to suck on my titties?" The Bee asked, snapping her gum enthusiastically. "Cantcha get off this board?"

I tried to back away to get the board out of her hands, but she held on tight, and then I tried to pull towards her to grab her boobs, but then The Bee pulled the board up and I fell on my ass and the poker players and the other girls went into hysterics.

As I was lying there, The Bee came around and put one glorious leg over me and squatted, so that she was leaning against the board, rubbing her crotch area against my nailed dick.

As I watched, The Bee undid the buttons of her crotch thingie, and pulled it up, showing a vagina with the hair shaved into the shape of a heart.

The Bee began rubbing my dick with her wet pussy, crooning. "Doncha wish you could fuck me wid dat dick? But you was a fool, you nailed it to the board...your dick was crucified."

The room went into hysterics again. The Bee was quite an entertainer. She ground her crotch up and down my nailed dick and I felt it pulsating intensely.

"Can you jerk off like that?" The Bee wondered. "Why don't you at least get off that way, piggie?"

"I left the keys to the handcuffs at home, it's too bad." Tom said, shaking his head and laughing. "You could try and give him a handjob, though."

The Bee smiled. "Yer missus--"she nodded at Gretchen--"give me a thousand dollars for tonight, so why not?"

The Bee stepped over me and helped me up. "You just stand there, big boy." She went to her bag and got some lubricant out.

The Bee rubbed and stroked my cock with her cute little fingers, giving me occasional looks at her glorious breasts.

She was really cute in the Bee outfit, with the wings and everything, and I began getting harder and harder, until finally my penis was almost pulling away from the plank.

The pain was truly excruciating, but I almost didn't notice it as I was so possessed by The Bee's incredibly cute boobs. She knew it, too.

"You likee my tits, hon?" The Bee decided that instead of not allowing me to touch her tits, she would rub them on my nailed dick, so she got down on the floor and rubbed them until my dick was just swelling something awful.

I began panting and she was panting and it got really hot, and then suddenly The Bee was dragged off of me by Gretchen.

"Well, I can't believe it." Gretchen said in disgust. "Even in your masochistic state, your dick takes over. I guess I'm going to have to do something to distract you and make you realize your true value, Milesey."

So she made me put hot pink lip gloss on and suck off the six men at the poker game! Stu was confused at what to do and he peed down my throat instead, but Gretchen made me lick up every drop!

The strippers watched and laughed, but The Bee looked just a bit sympathetic.

Finally, I was loaded back into Tom's van and taken home, where Gretchen, still disgusted, made me sleep in the basement, which was quite cold for fall.

"But what about the nails, honey?" I begged. "Don't you think maybe you should take the planks off...I can't sleep in this pain, you know."

But she didn't even take the damn handcuffs off! I lay on my side on the cold basement floor, the unpleasant board still nailed to my genitals and I eventually fell into a fevered sleep.

Around four in the morning, Gretchen shook me awake and guided me upstairs.

Gretchen unlocked the handcuffs and then used a hammer to pull the nails out of my dick, and the plank was finally removed.

Rubbing my dick with witch hazel, Gretchen kissed me softly.

"Honey, I do this for your own good. I just want you to understand that your male demands have really played hell in this marriage!"

She asked if I would try to improve, and what could I say? I told her I'd do whatever I could.

So that was it for the planks, thank goodness. I had been worried that the entire week would be lugging the damn thing around.

I had actually worried that Tom might attach bigger and bigger boards to my dick, and that I possibly would be unable to get out of the door in case of a fire!

But I knew I was on thin ice with Gretchen...and although I was tempted to be short with her sometimes, I was careful!"

"Miles, Estelle Karpinski says you were ogling her when she and Janet went running this morning. She says she felt like you were undressing her with your eyes." or

"Miles, you spent a long time in the bathroom this morning. I hope you weren't playing with your wang-wang...I assure you that's strictly prohibited."

or

"Miles, Tom said that when you mowed the lawn yesterday, you didn't clip around the edges as we've asked you to. Is this going to be a problem?"

It seemed as if I was spending half my time apologizing to Gretchen, and the other half wondering where she was going.

Gretchen spent a lot of time with my old friends Tom, Stu and Cade, and often I'd walk in after work and she'd be smoking a joint with her Negro friend Adonis-Lloyd Baskerville.

And of course she wasn't much interested in fooling around with me...I tried to approach her for sex and Gretchen was tired a lot, and her breasts, she said were "sensitive."

One night I was sitting next to her and oh, Gretchen's 36DD's were encased in this creamy ivory acrylic V-neck knit sweater with embroidered roses all over it.

We were watching "Third Rock from the Sun" and Gretchen was laughing at John Lithgow's antics with the uptight Jane Curtin character.

As Gretchen laughed, the sweater bounced against her full breasts, and I just bit the inside of my lip staring at her.

When she bent over to get her beer, I could see the hint of a black lace bra, one I was quite familiar with.

Wouldn't it be nice if she took off the sweater and let me play with her breasts?

It had been so long since I'd had her nipples in my mouth...

I tried touching Gretchen's arm. "Honey, I thought..."

Gretchen slapped my hand. "Shut it, Milesey, I'm concentrating here." She laughed again and the roses bounced on her boobs.

The sweater was short and pulled up to show her midriff, and although Gretch is chubby in the right places, she has a nice flat stomach.

I used to tickle Gretchen's adorable stomach when we were dating and in the early years of our marriage, and she got a kick out of it.

I reached over to touch it now and she slapped me again, this time on the cheek. "Goddamn it, I'm not going to tell you again, Miles."

Gretchen turned to the set again, and I stomped my foot like an enraged five year old. It just wasn't fair.

"Goddamnit, I've been doing everything around here, trying to get on your good side, can't you pay some attention to me?"

Gretchen looked at me coldly. "Get up and go into the bedroom, and get me the Spencer paddle. Take off your pants and underpants and come back in here."

I stamped my foot again. "Damn it, woman, I pay the bills and your ridiculous Visa charges, and I expect some good treatment."

Gretchen leaned forward, and oh, I could see the tops of her full breasts...a glorious cleavage if there ever was one--