Miles's Conundrums

Miles’s Conundrums Part 3

"Why are we here?" I asked curiously. The place was truly disgusting.

 

Gretchen smiled at me. "Well, you know Adonis-Lloyd wanted some rock, and so we came here after the club...you were out of it, honey."

 

I went into the bathroom briefly, and the toilet was backed up and the tub was filled with excess feces...because no one had called a plumber!

 

When I came out, Adonis-Lloyd was arguing with this huge ape, who pointed at me and whispered. Finally Gretchen came up to me.

 

"Honey, Shasta over there doesn't want to give Adonis-Lloyd any credit, and I don't have any more money in my purse...the drinks were a lot."

 

Gretchen smiled apologetically at me. What the fuck was going on?

 

" But Shasta says he'll give us some rock if you give him some lovin'...he thinks you're a hottie." Gretchen looked up at me with her appealing eyes. "I'll make it up to you later on..."

 

"But I'm not a WOMAN, Gretchen." I couldn't believe this. I am an investment banker, and a paragon of the Episcopal church, and my God...what was this?

 

Gretchen smiled and whispered in my ear. "Just with your mouth, honey. It will go a long way in getting us back together."

 

I'd do anything to get us back together. Sucking a crack dealer's cock in a shit-filled bathroom was a lot, though.

 

The guy, Shasta actually grabbed my ears and skull-fucked me as I knelt on the urine-covered floor and sucked his big black dick...oh it was awful.

 

Then I sat and watched Shasta, Lloyd-Jones and my beautiful Gretchen smoke crack together for a few hours...

 

At some point, we finally went home, and I quickly took off the women's clothes, but not before Tom and his poker buddies got an eyeful. I really have to throw him out, I thought.

 

We went upstairs, and after I was naked, I asked Gretchen if she was going to take off her clothes. It had been  a while since I'd seen her in the buff!

 

But Gretchen gave me her little half-smile and locked the police handcuffs on my wrists again, and guided me to her.

 

She did look hot in her clubbing clothes!

 

Gretchen began stroking and playing with my cock, and it got quite hard. I began moaning. It had been a week since I jerked off in the shower since the FIRST humiliating Friday night.

 

"So what was it like, sucking Shasta's dick, Milesey?" Gretchen touched her tongue to her upper lip.

 

Her purple nails rubbed the tip of my straining cock...oh she was hot! Gretchen smiled at me and reached to the middle of the shaft and began pulling faster.

 

"P-please...you said you'd let me fuck you if I sucked Shasta's dick!" I was begging, even though I knew it was futile.

 

"No I didn't..." Gretchen said, laughing as she tickled the bottom of my cock. "I just said if you sucked Shasta it would be good for restoring trust in our relationship."

 

That wasn't what she said, was it?

 

Gretchen stood up for a moment and gave me a big hug and a long tongue kiss, giggling at the same time as I tried to rub my cock against her crotch.

 

She pulled back. "No no...you must have patience, Milesey!"

Gretchen sat back down and began playing with my poor cock again.

 "I am not going to let you fuck me, sweetie, so let go of that one!" Gretchen began pulling my cock methodically "C'mon, just tell me what it was like to suck Shasta's big dick."

She pulled faster and faster until I felt as if I were going to have a big orgasm...and then, just as my legs began to shake, she pulled her hand away!

 

Gretchen looked at me and licked her lips. She unbuttoned her halter a bit, and I could see her lacy bra.

"Tell me, honey." Gretchen said, as she began her ministrations on my cock again. "Don't you want me to play with your ding-dong?"

 

"Well, um, he was big, and it was disgusting being in my mouth." I kept trying to pull my hands off the Police Handcuffs, but it was impossible.

 

"Yeah, welcome to the woman's chore, honey." Gretchen laughed as she tickled my frenulum. "It's gross, sucking dick."

 

"Um, yes, I guess." I tried to think more about Shasta and the dick thing. "It's kind of like waiting for a train wreck,when he comes."

 

Gretchen tilted her adorable head and looked up at me as she massaged my foreskin. "That's right. That's how I've always felt, Miles. I'm glad we're connecting!"

 

With that, Gretchen let go of my cock and took off her dress. She was wearing an incredibly hot red stretch lace demi bra and thong panties.

 

"You are so much easier to talk to like this, Miles" Gretchen said very seriously. "I feel so close to you."

 

Her long fingers played with my scrotum, which was quite full now...and she licked her lips again and smiled at me.

 

"I just wish that you were a little more interested in my needs, and not so self-focused, you know?" Gretchen took her non-masturbating hand and began massaging one of my nipples.

 

I was speechless. I felt I'd been quite involved in serving her needs. What the hell else could she want?

 

"Jesus, Gretchen, don't you think I've done enough? I thought after all the shit with Shasta, you'd at least blow me, honey."

 

Gretchen let go of my cock and then punched me hard in the balls and I fell over, howling. "Goddamnit. " she screamed.

"I thought you finally got what I had to go through, after sucking Shasta...and you're still just a selfish male pig."

 

She stalked out of the bedroom and went downstairs in her underwear to join the poker group, and I just lay on the floor, utterly mystified by my wife!!!!

 

The next day was a Saturday, and I took Gretchen to lunch, and we had a talk. "I just want you to be more focused on ME."

 

Gretchen's claim was that all I was focused on was getting my rocks off with her, and she wanted me to give her more attention and care.

 

I took her out after lunch and bought her a tennis bracelet, what the hell? I could sell some stock, right?

 

We went home and I put Gretchen in the bath and tended to her...and then gave her a nice massage, and lots of oral sex...I really worked on it!

After Gretchen had cum about three times, I pulled myself up and looked at her with pleading eyes.

 

"Is it my turn yet?" I asked this weakly. My dick was so hard!

 

Gretchen sighed. "You just ruined all the efforts you made. I am going to have to work on you, honey."

 

Gretchen got out of bed and got dressed in a cute little snug t-shirt that came up over her midriff and her faded old jeans.

 

I was going to get up too, as I had good arguments to make, but she motioned me to stay still.

 

 Gretchen went through the drawer, bringing out Stu's Police Handcuffs.

 

"I know you hate these" she said as she locked them behind my back.. "but like math flash cards, you need it! Now lie on your stomach on the bed!"

 

Gretchen then went into the closet and brought out a two foot metal bar with cuffs on each end.

 

"This is a spreader bar, hon." she said as she locked a cuff on each ankle so my legs were stuck apart. "I found it on your femdom BDSM site...cute, eh?"

 

Then Gretchen lifted up my crotch and pushed a pillow under my groin so my butt was sticking up.

 

Then Gretchen went back in the closet and brought out a long wooden paddle about three inches thick and five inches wide, and maybe a foot and a half long, with three rows of ten holes throughout.

 

"This is a Spencer paddle, Miles. I am going to break you of selfishness, and you should appreciate my efforts."

 

"Gretchen, baby, please. I'm trying to negotiate with you, and I thought I was being nice in giving you jewelry, a massage--"

 

WHACK! Damn, that Spencer paddle bounced off my ass!

 

"H-honey, listen to me." I said, trying to deal with the pain without showing it. "I want to be a considerate spouse, but I think you're being selfish and myopic. You--"

 

WHACK! THWACK! SLAM! SMACK! Gretchen was alternating whacking one cheek and then the other...and then both!

 

Now I was silently sobbing, my reasoned diatribe had been quelled by the intense pain from the paddle smacks.

 

"The Spencer paddle has these little holes because the air whizzing through assists me in hitting you harder and faster."

 

Gretchen sounded like a tour guide or a saleswoman for paddles...she was ignoring what I had to say, no doubt!

 

WHACK! SLAP! SMACK!

 

"I sure hope that you begin to realize how difficult you make things for us with your childish and self-centered ideas."

 

She whacked again and I screamed, my voice going up an octave.

 

Tom's voice came upstairs. "Is some chick having an orgasm up there? I heard this squeal!"

 

Gretchen chortled, and held her hand over her face. "N-no, Tom...I'm just teaching Milesey feminism up here."

 

Tom looked in. "Good Lord, what a lot of bruises and welts, man." He was at least sympathetic, or was he?

 

"I'm actually getting kind of tired of swinging this thing." Gretchen said to Tom in a little girl voice. "Could you do the honors? It's real important to your Gretchie."

 

I looked over my shoulder and in my horror, Gretchen gave Tom a big, wet kiss! He grabbed her ass and laughed.

 

"Why not, honey?"

I began to panic. "Tom, no, get out of the room, this is between me and my wife. Seriously, I'll call the cops."

 

Tom laughed. "Yeah, and explain to them why you were locked in this spreader bar thing? Right. I don't think so."

 

He lifted the paddle.

 

WHACK! WHACK! THWACK!

 

Gretchen could swing a mean paddle, but next to Tom's construction muscles it was winter unto summer.

 

SLAP! SMACK! CRACK! CRASH!

 

I was now sobbing and struggling in the Police Handcuffs. Of course I tried to pull my legs together, but the spreader bar kept them locked apart.

 

SLAM! Oh, God, he got my friggin' balls...

 

Gretchen mumbled something, and despite my tears, I turned my head jealously to see what was going on...

 

Gretchen was trailing one long nail up and down Tom's chest. "If you can make him cry out loud for five minutes, I'll..."

 

And she whispered in his ear...what was it?

 

Tom went to work on me, and indeed, I began crying loudly, screaming to the point that the neighbors called.

 

Finally, Tom threw the Spencer Paddle down, and he and my wife exited my bedroom, leaving me there in a semi-shock.

 

Gretchen came back in about an hour, wearing only a towel.

"Sorry about that, Milesey...girl's got to keep her promises."

 

I was still locked in the spreader thing with the handcuffs, and Gretchen jumped on the bed.

 

She threw off the towel and put her messy crotch just under my nose.

 

"This is what's known as a creampie...have some sugar!"

 

Licking up Tom's disgusting semen was just unbelievable.

 

I gagged, but Gretchen had me where she wanted me, my hands behind my back...and she pushed my face into her crotch, HARD.

 

Finally, she was cleaned out, and I licked her to an additional orgasm before she pulled out from my face and turned me over on the bed.

 

Sitting next to me on the  bed, Gretchen stroked my cock again, and it began growing...bigger and bigger. Finally it was straining and she pulled her hand away.

 

Gretchen reached under the bed and brought out a long, thin fiberglass riding whip with a tress on the end that I'd bought at some BDSM site.

 

Tapping it in her hand, she began talking to me quite softly.

 

While Gretchen talked, she rubbed the riding whip against my rock hard erection...

 

"Now do you understand about respect, and needs? If we have any future at all as a couple..."

 

I decided to use some logic. "Look, Tom's a pig. He doesn't buy you jewelry or take care of you, and you're so nice to him."

 

THWACK! The fiberglass riding crop snapped against my glans, and my penis wilted instantly.

 

Gretchen flicked the crop once more, and then began rubbing it softly against my dick again.

 

 "Honey, Tom is a different man than you, and he's secure in his masculinity...he's not a bullying little coward trying to manipulate me into bed, you know?"

 

I burst into tears. "And I am, right?" I asked resentfully. "I just don't deserve anything because I'm your husband--"

 

THWACK! Right across the face this time. That fiberglass crop hurt!

 

"No, you don't deserve. I didn't get married to be raped against my will." Gretchen said sanctimoniously.

 I think I really began to learn a lot that night. Finally, after a lot of swats from the crop, Gretchen finally unlocked me, and we actually made love!

 

It was the first time I'd cum inside her in some months...but I was starting to understand that I couldn't objectify her any more.

 

We began talking a lot about my commitment to her, and the burden she felt from my constant sexual demands.

 

"If only there was a way that I could make you understand the way your dick makes me feel weighed down, darling."

 

Gretchen said this, kissing me gently on the cheek one night. "If I thought of a way to give you insight, would you cooperate?"

 

"But don't I have insight enough?" I asked. "I'm a committed feminist, I worked with rape victims as a volunteer in college, I do all the housework now and I've like, gone down on a guy in drag for you...I'm trying."

 

Gretchen shook her head and got up and walked out of the room that night, and she wouldn't let me touch her for two weeks.

 

And of course she began wearing hotter and hotter clothes...lycra, frilly lingerie tops, that sort of thing...not even looking at me as she went by!

 

She walked in on me jerking off one day and flew into a rage. "Is that all you think about, fucking touching yourself?"

 

Out came the Police  Handcuffs. Gretchen made me stand in the middle of the living room, naked, with my hands cuffed this time behind my head.

 

She whacked my cock with the fiberglass riding whip until I was on my knees, crying.

 

"It's about US, not your desires, Miles. Right now, because of your shitty attitude, I don't want to interact with you, but that doesn't mean I want you whacking your willy!"

 

She made me write five thousand times "I will not practice onanism."

 

Then it was back to ignoring me!

 

So I had to try to not jerk off, as well as not touching her! What  a pleasant proposition that was!

 

Finally, I realized that I was being a little obtuse...I was desperate for her body, and I knew that I had to do something.

 

I  gave her ex-boyfriend Gary an update, and he shook his head.

 

 "When I was dating Gretchen, she made me jump through hoops, and then she made the hoops smaller. Beware, Miles, my man."

 

But she was such a hot girl! And I didn't want to be a chauvanist pig, you know.

 

Finally, after ten days of silence, I went to her, tears streaming down my face and said, "Look, I want to understand why my dick is such a burden to you. I'll do anything to resolve all this."

 

She brightened immediately. "I have a great plan for you I've been talking about with Tom, we'll do it this weekend. Actually, take the week off."

 

Tom?

 

Saturday morning found me standing naked in the garage. "Just wait there for me, darling." And I waited...it got cold, but I waited.

 

Finally, Gretchen and Tom came into the garage, and Tom was carrying a frightening looking metal thing  and a plank of wood about four feet long and three inches wide.

 

Gretchen brought out my old friends, the Police Handcuffs, and locked them on me, while Tom grinned broadly.

 Tom then said, "You might want to tie up his legs, too, since he might freak out about the nail gun."

 

"What? A nail gun?" My legs began shaking. "I don't--"

 

Gretchen gave me a big kiss. "No, honey. I want you to WANT to make me happy. I don't want to have to chase you around creation. Are you gong to be a little man?"

 

I nodded, feeling weak.

 

Tom waved the metal thing in my face. "You're a little business office faggot, so I don't expect you to know what this is, Miles."

 

Gretchen giggled.

 

"This is an eighteen gauge brad nail gun, and I chose it instead of a roofing nailer, because the nails are not as big and sharp."

 

Gretchen came up to me and kissed me, and began playing with my dick. "I wanted him to go easy on you, now make your wee-wee hard, Milesey."

 

Soon, my sex starved cock was long, but then the real business began!

 

Then, as I stood there in horror, Gretchen took the plank and put the end just under my scrotum.

 

 Tom, frowning, took the excess skin from my balls and yes, drove a brad nail through the skin to the wood.

 

I almost passed out. But Gretchen began kissing me while holding the plank.

 

"Can you take some pain for Mommy? Will you take your medicine like a big boy?" She was so tender, and it had been so long since she'd kissed me like this!

 

My hands were jacked up behind my head, and Gretchen lightly tickled me under my arms and gave tongue-plunging kisses.

 

Then Tom shot three more nails through my scrotal skin, being careful, bless him, not to impale my testicles.

 

"Now make his dick big, Gretch...too bad he's circumsised, or I'd have more loose skin to deal with."

 

Gretchen pulled down her halter top and offered me a big nipple, which hadn't been available to me in some time.

 

She let me suck her beautiful breast while she ran her nails up and down my cock...and it got big.

 

But, every time Tom drove a nail through on the little bit of skin on each side of my cock, I went limp again with pain...

 

But her boobie brought me back!

 

"Oooh, the pain is so sharp, Gretchen!" I was bleeding, too...

 

"No matter, darling...just suck Mommy's breast and let me kiss you and stay hard for Uncle Tommy!"

 

Finally, it was done. My cock and balls were essentially nailed to this two foot plank. Gretchen then let go of me, coldly.

 

I tried to hug her, the plank swinging from my hips and she  backed off. "Fuck off."

 

"What?" I was absolutely puzzled, as well as being in pain.

 

"Now then, Miles. Your dick is a burden to you for a while."

 

Tom put his nail gun away. He gave Gretchen a big kiss. "I'm going to get some for my little chore, right?"

 

Gretchen laughed as Tom pinched her ass.

 

"Yup, let's go inside. Miles, I want you to get to know your new penis plank...see what it's like to feel weighed down."

 

Then Tom batted the end of the plank with his hand, and the heaviness of it surprised me, it swung and I stumbled back, not being able to balance myself much.

 

Gretchen stroked the top of my dick with her finger, and it rose, painfully, dragging the plank up. Then Tom slapped the end of the plank and it went down again.

 

Gretchen stroked my dick and kissed my ear again, and painfully, the dick hardened and the plank went up again.

 

SLAP! Tom's heavy hand came down on the end of  the plank and it went down so hard it slapped me between my legs. My balls were in acute pain.

 

"Well, this should be a growth experience" Gretchen chortled. "C'mon Tommy, lets go upstairs and  get in the hot tub."

 

With that, she and Tom left me in the garage, my hands locked behind my head and my flailing penis attached to a piece of wood with brad nails.

I am over six feet tall, so the plank didn't hit the ground, but it sort of hung there.

 

And the nails were really pinching my skin! I tired of holding the plank up with my hand...but it was so painful!

 

 I looked down and imagined what would happen if Gretchen got mad and locked me out in the rain like this...would the nails get rusty?

 

 Would I get gangrene? What an emergency room scene this would make!

 

After about an hour, Gretchen opened the door to the garage. "Honey, what are you still doing in here? Aren't you going to do your household chores? It's Saturday, after all!"

 

Gretchen unlocked my handcuffs from behind my head, and patted me on the ass. "Tom and I are going to do some shopping, and I hope you can get some housework done."

 

"B-but like this?" I asked, the plank swinging between my legs. "Don't you think..."

 

Grechen snorted. "What? I do you the favor of giving you some feminist perspective on your cock-burden behavior and you want to get off doing your chores, too?"

 

While she was gone, I had quite  morning.

 

It was weird having the plank banging against the vacuum cleaner, and later scrubbing the bathroom floor with it hanging under me...

 

I was on my hands and knees in the cramped bathroom, and I kept putting my knee on the damn plank by mistake and nearly ripping my dick off!

 

The house was clean when Gretchen and Tom got in, but she inquired about the yard as she put a paper bag down. "Aren't you going to rake it? "

 

"I can't get my pants on with this board, you know." I tried to reason with her. "Perhaps if we bought some huge overalls I could fit it--"

"You see?" Gretchen said, looking at Tom. "I am just so glad I bought this."

 

She reached into her bag and pulled out a nasty little two foot whip with two ends. "This is a quirt used to whip dogs, but it can be used I guess for you too, dear."

 

But as she lifted it, Tom stopped her. "No, no...he just doesn't get why his laziness and his excuses are the burden, like his dick is. I have a better idea, which will help to remind him."

 

Tom took me out to the garage, where he took another plank, this one six feet long, and nailed it to end of the first one.

 

 But he put the six foot plank across, so it looked as if I had a giant "T" hanging off my dick now. It was heavier, and far more cumbersome.

 

Tom looked at me and grinned. "Now, I suggest you get to your yard raking. The yard is fenced, no one's going to see you out there."

 

Raking a yard with two planks nailed to your genitals is a lot of work.

 

I had to twist my body in order to keep the rake from bumping into the T planks, and it took me four hours to get an hour raking job done.

 

Shortly before I finished, Gretchen came out with the dog quirt. "Goddamn it, you forgot to scrub the baseboards!"

 

Despite Tom's psychology of the extra board, Gretchen apparently has faith in old fashioned discipline, and she chased me around the yard.

 

Gretchen was flailing with the quirt, until finally I fell on my T, my dick crushed under it (it got twisted.) and she whipped me until I screamed and cried.