Adam was in the middle of a Saturday evening jog this time when his phone beeped, interrupting his workout app. He glanced at the notification and saw that it was an email from "Mistress Kristen" and stopped in his tracks.
Slave, Mistress Katie will be joining us this evening. Get home and showered. -Mistress Kristen
He ran the last half mile of the trail at a very quick pace, before jumping in his car and driving home. Adam arrived home and quickly went upstairs. He heard two female voices talking and joking as he approached the bedroom. As he opened the door, he saw his wife, Mistress Kristen and her friend Mistress Katie. As soon as Adam opened the door, the merriment ceased. The room was adorned by lit candles, giving a soft touch to the room. As his eyes adjusted to the darkness however, a harshness crept in. Across the top of the dresser were various implements of pain. "I guess they want them handy," Adam thought to himself.
"Shower, and make it quick." snapped Mistress Katie.
"Yes Mistress Katie." Adam replied on his way into the bathroom.
He showered as quickly as he could. His cock began to swell when his brain finally caught up with his eyes. Mistress Katie had been wearing a black leather catsuit. Her round tits and ass beautifully featured by the tight leather. The catsuit also featured an open crotch, allowing for easy service. Her ass was pressed even higher by her high heeled red thigh boots. When the water turned off, Mistress Katie ordered from the bedroom, "Put your cock in it's cage and bring me the keys"
Adam quickly dried himself and restrained his cock and balls with the leather straps left on the sink for him. He then, just as last night, struggled to get himself flaccid enough to fit into his new cage. Once his cock was secure, Adam went back into the bedroom to face his Mistresses.
Mistress Kristen approached him first. She was wearing 4" heels that brought her taller than her husband. Her legs once again had black stockings on, complete with a matching leather bra and garter belt set. At the sight of her, Adam's cock began to swell inside its cage. Mistress Kristen attached the leash and dragged him to the footboard of their bed.
Once there, Mistress Katie approached. She took the keys from him and placed them on the nightstand. She then took the leash and pulled his cock downward, forcing Adam to spread his legs. She then tied it off to the footboard, securing Adam's cock to the footboard with very little slack. Mistress Kristen pulled two wrist cuffs off the dresser, handed one to Katie and they each secured one wrist.
Mistress Kristen shoved Adam's back and barked "Bend over, we want your ass up for us." Adam bent over as told when he felt Mistress Katie's sharp stiletto boot heel pressed against his neck, pinning his face to the bed. Adam felt his right arm stretched as Kristen threaded rope through it and tied it tight to the corner of the headboard.
"Hold still" Barked Mistress Katie as Adam's wife repeated the process with his left arm. Mistress Katie climbed onto the bed and raised Adam's chin to look him in the eye. Adam felt helpless, very much at the mercy of the cruel redhead staring into his eyes. Mistress Katie dangled a red suede flogger in front of him. Adam's fixation with the flogger was broken only by the sensation of Mistress Kristen tying his thighs to the footboard with another length of rope.
Mistress Katie swung the flogger towards Adam's shoulders. He tried to flinch, but his bonds would barely allow it. "Impressive!" Mistress Katie replied. "Only been a couple of months and you've got him bound this well"
Mistress Katie dismounted the bed and joined Mistress Kristen behind Adam. He turned his head to the side to get a better view of the ladies. He felt the sting of Mistress Katie's flogger on his ass. A quick flick of Kristen's riding crop made him try to jump. "Not too hard, you don't want to break the bed," his wife corrected.
The two women alternated flogger and crop strokes until Adam's ass glowed cherry red. There was no need for his cock cage now as Adam was sure his ass was hogging all the blood. Mistress Katie climbed back onto the bed and sat in front of Adam. His face winced as Kristen's crop grazed his balls. Katie sat with her legs open, pinning Adam's arms to the bed. The fiery redhead stared deep into his eyes, her cold demeanor indifferent to the pain manifest in the slave's face. She scooted her crotch to his face until her bare pussy was just out of his tongue's reach.
"Lick me!" Katie commanded.
"Yes Mistress!" Adam answered. He stretched against his bonds, desperately hoping to get the extra inch that would please his Mistress. He leaned against the footboard, the hard wooden top of it digging into his hips. He got close enough to deliver a lick up the length of Mistress's dripping pussy.
He kept going with tiny little licks while his wife moved her crop strokes down his thighs. Mistress Katie grabbed Adam's head, and pulled herself in, her catsuit gliding easily down the bed. Adam buried his face into Mistress Katie's pussy and quickly found her clit. He started sucking wildly when another sensation burned his already tender ass.
Mistress Kristen had picked up a skinny wooden ruler. The narrow length of it caused quite a bite. Adam grunted in pain into Mistress Katie's clit. "Mmm" Katie replied, "That little grunt feels good, do it again!"
Mistress Kristen swatted him again with the ruler, again getting a grunt out of the slave. "Keep going Kristen! I want this bitch to make me cum!"
"Yes Ma'am" Kristen answered as she began working her husband over. He sucked Katie's clit hard, flicking it with his tongue in between his grunts of pain.
Mistress Katie groaned as she edged ever closer to orgasm. "Make him hurt! I want to cum hard"
Mistress Kristen slapped Adam's hanging balls with the ruler. Adam tried to jerk but to no avail. He screamed into Mistress Katie's clit. Her whole body shook with orgasm and her cunt sprayed into Adam's mouth. He sucked every drop of Katie's sweet nectar and swallowed what he could.
"Care to switch places Kristen?" Mistress Katie asked as she climbed off the bed and took up station behind the slave's bright red ass and thighs. Mistress Kristen sat in front of Adam and brought her pussy closer to his face. "My, my", Katie said, observing Adam's ass and thighs, "You didn't leave me much to play with. Although I think I can find some way to amuse myself."
Kristen pushed her pussy towards Adam's face and he began to softly run his tongue up and down her wet slit. After a couple of passes, he felt a tight pinch on his inner thigh, down by the knee. "Ever played with clothespins before?" asked Mistress Katie.
"No Ma'am" Adam quietly replied before getting back to his wife's pussy. As he licked, he felt more pins being added up each thigh. Adam found Kristen's clit and sucked it into his mouth. He desperately wanted her to cum before Mistress Katie and her clothespins reached his balls. His legs tensed and he sharply exhaled as each pin was added.
Mistress Kristen grabbed his head and pulled him into her. She bucked her hips as her slave was getting her close to orgasm. Her legs tensed and Adam knew his wife was close to orgasm. He prepared to enjoy the rush of juices from his wife's pussy. His cock stirred at the thought, knowing that she would return the favor.
Suddenly, Mistress Kristen backed up ever so slightly, leaving her dripping slit just inches from his face. She started rubbing herself at a mild pace, maintaining her arousal, but not taking it all the way to orgasm. Adam stretched and reached for her pussy, straining against his bonds. Then, as if it were a choreographed maneuver, Mistress Katie applied the first clothespin to his scrotum.
"Aaaah," Adam winced in mild protest, but the first pin was followed by four more. An almost sadistic grin came across Mistress Kristen's face at the sight of this.
"Not enjoying yourself slave?" she asked. "Don't worry, we have more in store for you."
Adam swallowed hard as he felt Mistress Katie's finger against his asshole. Her finger probed his opening before pushing into him. His cheeks reflexively tightened before being chastised by the gorgeous redhead behind him. "Trust me slave, it will be easier if you can relax."
Mistress Kristen chimed in "You told her that you've never been fucked in the ass. That will change tonight. It's funny, you've always enjoyed bending ME over the footboard..." Adam felt Mistress Katie's finger once again, generously massaging lube onto his virgin asshole. Mistress Kristen scooted forward and allowed Adam to resume licking her. "Just for a moment slave, Mistress Katie is putting her cock on. I want to watch your face while she fucks you!"
Mistress Kristen's hand again replaced Adam's tongue as he felt Mistress Katie's strapon pressed against his clenched ass. An open handed slap to the ass reminded Adam to attempt to relax.
The dildo felt strange as it slid inside him. It burned and stretched, but also felt warm and filling. Mistress Katie pressed against him slowly and firmly, the dildo burrowing deeper into his ass. As she pulled back, a strange calm came over him. Katie pulled it almost all the way out before resuming her slow steady inward stroke. The strain once again returned to Adam's face as the dildo went a bit farther than the last stroke.
Mistress Kristen started rubbing her clit harder. "Mmmm, wince for me slave boy!" She gently pinched her clit and rolled her thumb and forefinger back and forth. "Oh, god, you're so sexy when she's fucking your ass"
Adam's ass offered less resistance with each stroke and Mistress Katie gently increased her rhythm. She pushed in a little farther each stroke until her hips were slapping against Adam's warmed red bottom. "Good boy!" remarked Mistress Katie, "You're taking all of my cock" Adam groaned with an strange blend of pleasure and humiliation.
"Fuck him harder! I want him to scream for me while I cum!" Mistress Kristen yelled.
Mistress Katie obliged her and drilled into Adam's ass fast and deep. Adam's groans grew into full fledged screams as his asshole was stretched. Pleasure began to replace the pain in his voice. All of a sudden, Mistress Katie turned the vibration on in her strapon and Adam's screams went an octave higher.
"Oh God Yes!" shouted Kristen, her stocking clad thighs shaking. She came and unleashed a torrent of fluid from her pussy. Mistress Katie took one final stroke, burying the dildo deep in slaveboy's ass and holding it there until Kristen's orgasm subsided.
Adam smiled. In his past encounters, satisfying Mistress Kristen meant that he would soon be enjoying a wonderful orgasm of his own. Mistress Katie pulled the dildo from his ass and sat next to Kristen on the bed. Both women gazed upon the euphoric look of anticipation on his face.
"You can tell him." Mistress Kristen said.
Adam was puzzled. "Tell him what?" he silently wondered.
"Well Adam," Mistress Katie started, seemingly in response to his silent question. "I'm not entirely pleased with the progress that you and Mistress Kristen have been making. You're expecting us to take care of you right now, aren't you?"
Adam nodded in response.
"That's the problem. You're serving her well, but you're only doing so to intensify your own orgasm. The true goal of slave training is to derive your pleasure from service. Then if you truly please your Mistress, she will reward you with an orgasm."
She turned to Kristen. "You've been too lenient on him. I can see why, that man has a magnificent cock. So much bigger than the one I'm used to at home. It's natural that you'd like to keep that cock happy" She again turned to Adam, "That's why you're going to stay locked up."
Adam's heart skipped a beat. Mistress Katie dangled the keys to Adam's cock cage in front of him, and put them in her purse. "I'll hang onto these. And you'll continue to serve Mistress Kristen until I believe you have earned an orgasm."
She grabbed her purse and exited the bedroom. Adam looked up at Mistress Kristen incredulously, searching for remorse in her eyes. He was met with only a stern response. "She's right."