The Milking Contest
by Anonymous

I was just sitting down, relaxing after a hard day's work, watching a little television.

SLAM. The back door closing hard jarred my attention. Maureen was home. I had a feeling that she wasn't in a good mood. From the other end of the house I heard her muttering --

"God damn fucking bitch --she doesn't know who she's dealing with. She'll never treat me like this again --fuck"

I waited for her to come in and tell me all about her latest problem at work. I knew she was trying to adjust to this new job and wasn't getting along with one of her co-workers, some secretary named Claudia. And I surmised that this was the "bitch" she was ranting about.

She came in to the room and walked straight to me.

"Get up. We're going out."

"Where are we going --HEY I'm watching that!"

"Not anymore. I'm going to fix this bitch once and for all and you're coming with me."

I sighed and knew that when she's in a mood like this, there won't be any relaxation for a long time --

Two hours later, I found myself at the home of Claudia and her husband Joseph. A posh tastefully decorated suburban home. And was I sitting in their posh living room eating hors d'ouvres and sipping Chardonnay? Of course not. I was walking into their dank, scary basement/dungeon, naked, being led about by a chain which held Maureen's little hand at one end, and my tightly bound testicles at the other.

Apparently, this Claudia person did not get along with Maureen, intentionally sabotaging several of her accounts and making her look foolish in front of her new employers. Also she fancied herself as something of a domme, bragging to my girl about how she held her husband in servitude, etc etc, and how Maureen could never measure up to her. Maureen, being somewhat competitive could not resist answering her challenge, but I knew this was a BAD IDEA.

So here I was, balls painfully separated and constricted by leather straps being lead about by the genitals to some inevitable torment. Ahh, the things one does for love. Claudia and her husband were here as well. Him naked and tied to one of two poles in the room, hands restrained high above his head to a metal eyelet in the ceiling. Her done up in high bitch gear. The other pole, I imagined, was for me.

"Restrain him and we'll begin", said Claudia.

No sooner said than done and I found myself in the same predicament as the hapless Joseph, tied to a pole with my arms restrained. The poles were about 5 yards apart and we were tied facing each other. I noted with a little pride that my cock was definitely larger than his.

Claudia took control of the proceedings and outlined what exactly would happen.

"Now bitch. This is the little game that we are going to play. If you are woman enough. It's called a milking contest. It will once and for all prove just who is more skilled, sexier, and in general - better. I will milk your pathetic slave and you will try to milk mine. The winner will get to untie her slave and then have her way with the loser who will submit unconditionally for as long as the winner desires. Do you agree?"

"So who ever makes the slave cum first is the winner?", Maureen asked.

Claudia laughed. "Oh please, we can't have a 30 second contest now can we? By the look of things, your slave is ready to cum already! No, the winner will be the first to make the slave cum three times. That's a thorough milking. Don't worry though, I have Joseph well trained, he won't cum at all, if her knows what's good for him. So, do you agree to the terms?"

"Yeah bitch --I agree. Let's do it"

Maureen strode over to me, her heels elevating her so she looked at me eye to eye.

"If you cum for her, I'll fucking kill you." This was a BAD IDEA.

Claudia spoke up "And now, BEGIN."

Maureen approached Joseph and started right in on his bobbing shaft. Claudia walked over and whispered in my ear.

"You're mine little boy. The bigger they are the harder they fall --."

She grabbed my testicles, squeezed them roughly and sank her mouth onto my cock. I immediately panicked, knowing that to cum probably meant years of torment from Maureen. The woman was an expert, her mouth and hands devouring my dick.

I heard Joseph moaning from across the way so I knew Maureen was getting to him. Claudia was certainly getting to me. She stopped using her mouth and just used her hands to milk me, spouting a litany of filthy language to turn me on.

"Come on slutboy --cum for Claudia --gonna drain that big horse cock dry --"

She knelt and used her tongue to tickle the cumshot out of my balls while she pumped up and down my shaft with both hands. I had no more resistance and came in huge spurts all over the floor as she moved quickly out of the way.

"ONE DOWN, you'll be mine soon bitch!" She laughed triumphantly.

I actually felt better now, once I had cum, I thought I would be ok for a while. She licked and pumped and sucked to try to bring my cock back to life, but I was able to resist. I tried to think nonsexy thoughts. I heard Joseph screaming from across the room as Maureen evened the score and quickly went ahead 2 to 1 as she made him cum twice in under a minute. My babe! She was going to win.

She probably would have won if I hadn't looked down. Claudia was getting frustrated and couldn't figure out how to beat me, until my gaze fell upon her open-toed high heeled shoes.

"You fucking worm. You're looking at my feet, aren't you?" Her eyes lit up in newfound knowledge. She slid her right shoe off to reveal her perfect foot, which she slid up my leg. As soon as her toes made their way up and brushed against my balls, my cock surged to attention once again. She used her lethal little foot relentlessly on my once-again swollen cock, crushing, squeezing, rubbing --until I shot another load all over her toes --it was 2 to 2.

My cock was thoroughly used and exhausted. I didn't think there was anyway she could get me up again, at least not before Maureen won the contest. Across the room, Joseph was moaning and groaning as she jerked him hard. I had the bad feeling that Claudia was going to torture my limp cock in a last ditch effort. Instead, she had other ideas. She petted and stroked it gently and softly whispered in my ear:

"Ever since I first saw that bitch Maureen at work, I knew I had to have her. And I will have her. Do you know why, slutboy? Because you want me to have her. You'll get to see the whole thing honey. You'll get to see my slave hold her down. You'll get to see her suck my toes. You'll get to see her lick my cunt and ass. You'll get to see her sweet little asshole opened up by my big strap-on. Come on slutboy --I know you want it. You'll get to see her beg and plead and sigh and cry at my feet. Just cum now --."

By now I was fully hard again. I tried to close my eyes to shut out the sensation, but she was playing me like an instrument. I couldn't help but visualize the scenarios she was describing. My beautiful Maureen, mascara running down her face, eyes bulging wide as her ass is stretched to the limit by this deranged whore. Claudia cackling madly as she uses Maureen's gorgeous face as a fuck-toy. Claudia pissing all over Maureen from head to toe while Joseph holds her in place. Maureen screaming in pain and pleasure as she orgasms on Claudia's fist. God it was too much --.

Claudia sensed the moment was at hand and applied a little bit more pressure to my overly engorged cock and I exploded screaming. Maureen heard, and turned her head from Joseph just in time to be greeted by a face full of my cum, which had impossibly jetted the five yards across the room as I thrashed and shook in the restraints. Finally it was over and I sagged down, my balls drained of every bit of cum, essesence and energy. I was finished.

Claudia rushed over to unshackle Joseph and they quickly moved to claim their prize. Just before having a dildo shoved into her mouth Maureen manage to get out a quick and vicious 'You're going to pay for this" in my direction --

And pay I did. But in retrospect, it was worth every minute.