Its Not Supposed To Be Fair

"No, there's no way. His dick is safely locked in a cage, he can't come."

"Wanna bet?"

"Yeah, ok, what are the terms of the bet?"

"Give me an hour to do anything I want to him, with his chastity cage on. If he cums, I win. If not, you win."

"And what do I get when I win?"

"IF you win, I'll eat you out a few times. If I win, I borrow this one for the week. Deal?"

"Deal."

Mike could only watch in fear, a ballgag in his mouth while he knelt in front of the two mistresses, his wrists locked to his ankles behind him. His mistress was a blond woman of medium height, strict but fair. He had given her the key to his chastity belt a year ago, and by following her commands closely, he had managed to earn himself a few releases. Today she was wearing a tight white latex bra that held her large tits in perfect view, and a tight white thong that showed off her long smooth legs and tight ass. Long black opera gloves covered her fingers, and a small key hung on a chain around her neck.

The woman she made the bet with was Stacy, a friend of Mistress. Stacy was well known as a much cruller and more sadistic key holder. She stood a few inches taller than Mistress, and wore black tape in the shape of X's over her nipples, a red g-string, and had tight medical gloves over her hands. She had brought with her a briefcase, which she now opened.

Pulling a bottle of lube out, she spoke. "First things first, you've got to relax the anus and begin to stimulate the prostate." Next, she pulled out two strap-ons. "I assume you've trained your slave's ass before?"

"Well of course, but it has been some time."

Stacy smiled and tossed a strap-on to Mistress. "It'll come back to you. Just like riding a dyke."

Stacy unlocked Mike's wrists from his ankles and pulled him to his feet. Then she took a good look at his chastity cage. It was a pink plastic cage that snugly held his cock to his balls, secured with a small padlock.

"Aww, its so cute! I can't wait to make it painfully tight for you!" Stacy smiled wide as she cupped Mike's balls, pulling herself closer to him and pressing her perky tits against his chest. She slowly inched closer to his face, turning to whisper softly into his ear. "I'm gonna make you regret ever being born." She gave his balls a painful squeeze.

Mike gulped, trembling. His cage twitched. Stacy and Mistress laughed.

Stacy led Mike to the bed, softly caressing his torso and thighs along the way, giggling while his cage bounced up and down. At the edge of the bed she stopped him, and bent him over at the waist, until his face was pressed against the sheets. After a playful spank on the ass, she opened her bottle of lube and poured some into his ass crack, and began messaging it into his butthole.

"You can start your timer now. within an hour I'll make him cum in his cage. And then I'm taking his chastity key for a week. A deals a deal."

Mistress smirked at Stacy's confidence, and set the timer on her phone. Then she pulled up her strap-on, tightened the straps, and spoke. "Michael, Dear. I forbid you to cum in the next hour."

Mistress then looked at Stacy expectantly.

"Shall we begin?"

As Mistress walked up to Mike's exposed ass, Stacy grabbed Mistress's strap-on and began to guide it in. Mistress placed her hands gently on Mike's hips and pushed her strap-on in slowly, inch by inch, thrust by thrust. She listened to Mike's every whimper or moan, adjusting her pace and angle to what made him feel best. Mike whimpered quietly, his face red from the shame of getting pegged. the same shamed that fueled the raging lust that made his cock strain tightly against his cage. Once Mistress was fully inside him, she picked up the pace, thrusting into him harder and faster.

She pounded into him for about 10 minutes, her thick strap-on rubbing against his prostate. His cock strained to get hard in its cage, and his balls ached for release. When she got tired, Stacy stepped right up to keep it going. After another ten minutes of being violated and mocked by the two women, Mike's chastity cage was bouncing as his cramped package tried mightily to get hard. The prostate stimulation had made him incredibly horny.

Once It was time for mistress to step back in, they flipped Mike over to his back, and made him hold his legs up. While Mistress worked his ass over with her strap-on, Stacy straddled his face and took a large wand vibrator out of her briefcase.

As she set it against his cage, she set it to a low setting. The vibrator felt weird initially, but the stimulation made his straining much worse. As Mistress reamed his ass, Stacy moved the vibrator around his cage, stimulating him through the pink plastic prison his penis was throbbing against. Stacy's ass straddled his face, and the thin sheer thong was the only thing between his mouth and her pussy. The scent of sex invading his nose made him even hornier.

After another twenty minutes of this torment, Mike was lifted to his feet and his hands raised above his head, chained to a hook in the ceiling. Mistress flopped onto the bed, exhausted from pounding his ass. Stacy reached into her briefcase and pulled out a small egg vibrator and a little string. She squatted down in front of Mike, as if to take a good look at his throbbing locked up cock. Then, she grabbed his balls, cupped them against his cage, and gave a playful squeeze. She looked up at him and grinned sadistically.

"These feel nice and full, how long has he been locked up?"

"About three weeks." Answered Mistress.

"Oh wow. Bet it'd feel real nice to cum right about now." Stacy winked at Mike. Mike could only moan into the ballgag.

Stacy placed the egg vibrator between his balls and cage, then tied the string around his balls so it would all stay in place. Then she turned it on. the vibrations through his cage were already making him throb, but the stimulation to his balls pushed him closer to an orgasm. Mike had to try to hold back from cumming, and tried to force his mind to think about anything other than the desperate need to cum and the vibrations that might make that possible.

As Mike struggled to control himself, Stacy turned and walked over to Mistress. Stacy bent down and gave a gentle kiss to Mistress's lower abdomen, then another a little higher, and another a little higher still. Stacy slowly worked her way up Mistress's body, gentle pecking kiss by gentle pecking kiss. Mistress smiled and bit her lip. As Stacy reached her collarbones and neck, she gently ran her fingers up the inside of Mistress's thighs. Mistress moaned in response. Stacy sat up, straddling mistress on the bed, and grabbed her face, staring intensely into her eyes. With an intense lust, like an unfillable hunger, she kissed her, passionately. Lip to lip, tongue to tongue, the two made out fiercely as Mike looked on, helpless.

After some time, the two ladies collapsed on the bed to catch their breath. Mistress checked the timer on her phone. "Oh wow, only thirty seconds left! I'm so gonna win this bet."

"Hmm sure ya are." Stacy winked at Mistress and stood up, grabbing a crop in her left hand. She walked forward and with one simple motion of her right hand, she pulled the string around Mike's balls off, letting the egg vibrator fall to the floor. Mike's cock bounced and strained, aching desperately for release. Mike shut his eyes and held back his orgasm for dear life, the vibrating sensations having pushed him right up to the edge. Stacy cupped his balls and cage, making him jump and throb. Stacy smiled. Mike stared pleadingly, his pathetic attempt at begging being stifled by the ballgag.

"10 seconds left"

Stacy let go and stepped back. Mike's cock bounced and twitched as it throbbed against its cage.

"Five"

In a flash, Stacy swung at his balls with the crop. She stopped just short, but the momentum carried on and the end of the crop flexed just enough to tap his balls. The sudden stimulation broke Mike's concentration.

"Four"

It was too late. Mike knew it. Stacy knew it. He was passed the point of no return, despite his attempts to hold it back.

"Three"

He could feel his cum pumping from his balls to his cock, and he held with all his might, hoping he could delay its release until the time was up. All he did was slow it down a little, just not enough.

"Two"

It began as a few drops, then a small stream of cum, flowing out of Mike's aching caged cock. Stacy threw her head back with laughter. Mike's cheeks burned bright red as his knees shook, and tears began to form in his eyes. Mistress frowned furiously.

"Hahaha, yeah you REALLY won that bet" Stacy chuckled, and tapped Mike's balls with the crop a few more times, delighted at its pathetic spurting of cum.

Mistress angrily ripped the key necklace off of her chest and handed it to Stacy.

"Keep him. I don't have any use for a slave that cums without permission."

Mike looked pleadingly at Mistress as he sobbed into his ballgag and tears formed in his eyes. Mistress just angrily stormed out of the room. Stacy chuckled at his misery, and looked him up and down once more.

"Well hello my new slave. We're gonna have so much fun together. I cant hardly wait!"

Stacy took the ballgag out of his mouth. He momentarily stopped sobbing to look at his new mistress through the tears welling in his eyes.

"That wasn't fair."

Stacy cackled sadistically.

"Oh darling. Its not supposed to be fair."