Mistress Katie Supervises Ch 05

Michael prepared himself as he had been instructed for the day, Domina had arranged that Mistress Katie would be supervising him while Domina took care of other matters. He had been eagerly anticipating the awaited date; it had been many months since he had submitted to Mistress Katie. Domina's friend Katie had visited to supervise his state of chastity and frustration during each of the past four summers, ensuring Michael remained in an appropriately slutty state, needing to cum and needing to kneel before a demanding lady, while Domina was away for weeks at a time.

Sadly, Domina's schedule did not leave her the time or energy to supervise her slut boy as often as either of them might wish. So it was to the benefit of all that Mistress Katie was willing and available to take him out of Domina's way for the day and to ensure he received some of the treatment he so deeply desired, and needed to ensure continuing good behaviour.

Michael showered and shaved, both face and balls, locked the chastity cage on his cock with a condom over the tube to catch any messy drippings, and dressed in the shorts and shirt Domina had chosen for him. As he reached the bottom of the stairs she was waiting for him. Dressed in a long black skirt, polished five-inch black heels and a white blouse, Domina looked like a school mistress ready to discipline a naughty pupil. She held out her hand.

"Keys," she said.

Michael placed the two small brass keys in her hand, one loose, the other on a long leather cord. He watched as Domina slid the leather thong over her head, letting the key fall between her beautiful breasts. The other she placed in a small envelope. Sealing and signing it to prevent tampering she handed the envelope back to Michael.

"Give this to Mistress Katie when she picks you up."

"Yes ma'am," Michael replied softly.

Domina then took her slut's face in her hands, her deep red manicured nails framing his face as she lowered her own to kiss him deeply. Michael's mouth parted as her tongue slid deep between his lips, gently fucking his face as his Domina kissed him. She broke the kiss as he started to moan around her thrusting tongue and stepped back, her lipstick bright on his lips.

"Nice colour," Domina said with a smirk, "I want you to behave yourself for Mistress Katie today, and I will see you later."

"Yes ma'am," Michael whispered, "I will be good."

She retouched her lipstick, and Michael then watched as Domina headed for the door, her own schedule pressing.

His own lips now cleaned, Michael waited patiently for Mistress Katie. His mind worked overtime as he reviewed her past visits. He knew she enjoyed keeping him horny and dripping inside his cock cage for hours before she considered releasing him. Those releases, when they did occur, were intense and draining, but that act of release did not free him from his commitment to serve his Mistress. Each time, as his arousal ebbed in post orgasm, he was still expected to consume his collected pre-cum drippings, and his cum if Mistress had taken his orgasm, by whatever method she decided to feed it to him. Michael could feel his cock trying to rise against the confining cage as he recalled sucking his cum from Mistress Katie's fingers, and from her manicured toes, but the narrow tube of the CB-6000 had been effective in training his cock not to fight its sturdy confines.

As he contemplated switching his computer on while he waited, Michael heard Mistress Katie's car pull into the driveway. Nervous with anticipation, as he always was when she visited, he opened the door as she reached the step, and closed it behind her as she walked into the house.

Mistress Katie walked down the short hallway into the living area, she turned to look back towards the door where Michael had remained. She wore a translucent white blouse covered by a short black satin vest. When she turned, Michael could see the exposed lace of her bra through the open neckline. Mistress Katie's legs were covered by a knee-length leather skirt. Cut wide, it opened and flowed around her shapely legs as she walked. The patterned black hose she wore was evident on her sexy calves down to the black stilettos she wore, the toecaps of each shoe covered with pointed steel studs.

"Well, slut," Katie said in a calm voice as her toe tapped on the wood floor, "is that how you have been trained to greet me."

"No Mistress, I am sorry Mistress," Michael blurted.

He moved quickly down the hallway to the open area where Mistress Katie stood. Under her watching eye, he pulled his shirt over his head, then lowered his shorts and boxer-briefs to the floor. Stepping out of his clothes he stood there, naked except for his cage, his hands at his sides, exactly as he had greeted Mistress Katie for each of her previous supervision sessions.

"That's better," she said, "just because I said we were taking a road trip today doesn't excuse you from your other responsibilities."

"My apologies Mistress," came the whispered reply.

Silently, Katie started to inspect her slut. Her hands slid across his shoulder and chest, Beautifully manicured fingernails in red with black tips closed on his sensitive nipples, teasing and pinching. Michael moaned at her touch, and struggle to remain still as he stood for his Mistress' inspection. Standing close, she again slid the tips of her nails over Michael's hard nipples, scraping her nails gently over them again and again as he trembled under her touch.

"You like that, don't you slut?"

"Yes ma'am," Michael groaned weakly in reply.

Mistress Katie's hands slid over Michael's chest and back, stroked his ass as she imagined spanking and fucking him, and tested the security of the cage that encased his cock. Michael moaned softly as her fingernails slid across his ass. He trembled when Mistress Katie took his balls between her thumb and fingertips of each hand. She rolled and squeezed them gently, then squeezed again, a little more firmly, watching Michael's face for his reactions. She smiled as he moaned at her ministrations.

"Well, these feel nice and full, how long has it been since they were drained?"

"Weeks, Mistress," he moaned.

"Good," she smiled, "then they should be nice and full for me. But we're going to see how much more there's going to be by the time we unlock this cage. Speaking of which, you have something for me."

"Yes Mistress, the envelope is in the pocket of my shorts."

"Well, put them back on, and hand it to me. Leave the boxers there, you won't need them. Quickly now, we have to get going."

Michael redressed as Mistress Katie headed toward the door. She stood there with her hand out for the envelope, and after Michael presented it to her, she indicated that he should open the door. By the time Michael had exited the house and locked the door, Mistress Katie was already in her car waiting for him. As soon as he had buckled his seatbelt, Katie reached over and tugged on the belt holding his shorts closed.

"Open them," she ordered.

Michael undid the belt and, after looking around to see if any of the neighbours might be watching, unbuttoned his shorts and slid the zipper to the bottom.

"Better, keep them like that," Mistress Katie instructed as she slid a hand through the open zipper to hold his cock cage and caress and squeeze his balls, "any complaints and you'll lose the shorts completely."

"Yes ma'am," Michael whispered.

"Good boy,"

With one more squeeze, Mistress Katie released her slut's balls and put the car in gear. She backed from the driveway and headed off to start their day. At each traffic stop she slid her hand into Michael's lap again and curled her manicured fingers around his balls. Holding them in her hand she alternated between squeezing them lightly and running the tips of her pretty nails over the taut skin while Michael moaned in response as he struggled to sit still for her.

Finally, the car pulled up to a stop in front of a tall apartment building. Mistress Katie took Domina's envelope and slipped it into a larger one of her own. She quickly wrote a short note, added that too, and sealed the envelope.

"Go up to Room 1412, slut, and do what you are told. I will meet you again soon."

"Yes Mistress," Michael said softly. He fastened his shorts and took the envelope from Mistress Katie. As he stepped from the car and closed the door, Mistress Katie put her car in gear and drove away, leaving him there with his instructions.

Entering the building, it was not until he found the second doors locked that Michael realized he needed to buzz the apartment for permission to enter. Pressing 1-4-1-2, he waited with increasing apprehension.

"Yes," a female voice greeted him.

"Uh ... it is Michael," he replied nervously, "uh .. Mistress Katie sent me."

"Come up," the voice responded, "the door is open, lock it after you enter and prepare for inspection as you did for your Mistress."

Michael pressed the button to reply but the connection was obviously broken, the circuit closed by the woman who had been speaking. He was startled by the sound of the door behind him buzzing as it unlocked and he moved quickly to pass through it. His cock twitched in its cage on the ride up in the elevator, and he felt a thick droplet of precum, residue of Mistress Katie's teasing hand in the car, ooze from his caged cock into the waiting condom.

At the door to apartment 1412, Michael paused, and after glancing each way in the hall, he opened the door and slipped through. Quietly, he dead-bolted the door, then stripped. Slipping out of he sandals, he removed his shorts, folded them and placed them beside his footwear. His t-shirt followed soon after and he stood there, waiting.

"Come in here," a throaty sensual voice reached him from inside the apartment.

Michael now recognized that the voice belonged to Miss Marlene, a friend of Mistress Katie's. As he stepped from the hallway and looked to see where he should go, he saw her standing in front of the broad wall of windows in the living room. She pointed at a circle of carpet that was positioned on the floor beside her.

"Stand her and face the windows, Michael."

Her orders were spoken softly and clearly, but she obviously did not intend to negotiate. Michael moved quickly towards the chosen spot. The carpet was thick and soft under his feet, a welcome change after the cool marble floors. He stood still, his feet slightly spread as he had stood for Mistress Katie. Miss Marlene stepped out of his peripheral vision as he assumed his required stance. What remained in his vision was enough to keep his slut mind pleasantly distracted. A minimalist free standing shelf of glass and steel was positioned in front of one large window pane, on which were a dozen pairs of beautifully sexy shoes. Each pair of stilettos had heels at least five inches tall. Pumps, open and closed toe stilettos, sling backs, and more, Michael imagined Miss Marlene wearing each of them as she teased the dripping precum from his cock onto the shiny leather.

Michael had only seen Miss Marlene briefly as he crossed the room, but that was enough to have the desired effect. Each time one of her heels clicked against the floor, Michael saw her in his mind, still silhouetted against the open sky beyond the windows. She was wearing a diaphanous white blouse that flowed loosely around her body. It would have revealed every detail of her brassiere if she had been wearing one. Instead, it let Michael get a clear sense of the way her large rounded breasts moved under the many folds of cloth as she turn to face him and then walked behind him. He tried to recall if he had seen her nipples against the fabric, but fleeting memory easily meant it could have been an illusion of desire.

She also wore a skirt, black like Domina's and Mistress Katie's had been, but even shorter still. Reaching only her midthigh, the tight knit skirt moved with Miss Marlene's thighs and buttocks as she walked around to inspect the slut before her. But it was her footwear that had burned into Michael's memory. Tall black boots, knee-high, but with flaring tops at sides and front to wrap around her knees, and make them appear even taller. They laced up the back of each calf, from the sole to just below the knee with criss-crossing red laces which drew them tight to the form of her shapely legs. All this fantastic leather was balanced on six inches of shining steel stiletto heels, the heels Michael heard ringing as she took each step behind him.

Michael stood still as Miss Marlene inspected him. Then he felt her step behind him, in her heels she was as tall as he was and the thin fabric of her blouse did nothing to minimize the very clear touch of her hard nipples to his back. One hand slid around his chest and a finely manicured fingernail gently teased his right nipple.

"Mistress Katie said you were an obedient slut," Marlene said softly, "I like that."

Her nail flicked slowly back and forth with each word as she continued.

"She also said you like heels. Did you like my boots Michael."

"Yes ma'am," Michael whispered hoarsely, "they are very beautiful."

"I bet you'd like to polish them for me, wouldn't you?"

"Yes ma'am."

"What if I wanted you to kneel and polish them while I wear them? Would you like that slut?"

"Yes ma'am, I would like that if that is your desire."

"Mmmm, such a willing slut you are. Perhaps I shall have to borrow you from your Domina, and I will lock you in my closet to polish all of my sexy boots and shoes. I'm sure that with your cage to contain any messy drippings and a nice thick dildo to ride while you work, you would enjoy that a lot, wouldn't you."

"Yes ma'am," Michael moaned softly under her delicate touch.

"Such a willing slut you are, I want you to imagine yourself in that closet with my boots and shoes, polishing away as you listen to me entertaining my lovers in the next room. The sounds of my orgasms will be your reward for being my show shine slut. What would you say to that Michael?"

"Thank you ma'am," Michael whispered as his reply to her question.

Miss Marlene's hand slid downwards until her hand caressed Michael's balls under his cage. Holding his cage and balls up and away from his body, Miss Marlene moved around to stand in front of the his. Michael's breathing quickened as he again admired her sexy attire and was unable to refrain from a small moan of pleasure as she gently kneaded his tender balls.

"I bet these would be very full after a day of serving me and my shoes, wouldn't they?"

"Yes ma'am, very full."

"Mmmm, I like that," she added, " and if I drained them, I might have you suck your messy drippings from my toes. I know you've done that for Mistress Katie, haven't you?"

"Yes ma'am, I have done that for Mistress Katie."

Miss Marlene smiled, slowly she raised two fingers to Michael's lips and slid her finger tips around his open mouth. As she slid them inside and Michael began sucking gently on her fingers, she continued.

"She tells me you're very good with your mouth, and I do expect that of all the sluts I train, or borrow, for service. Sadly we do not have more time today, or I would be putting that slut mouth through its paces."

Releasing Michael's balls as she withdrew her fingers from his mouth Miss Marlene stepped back and turned to face the windows. Michael watched as she leaned on the glass, her large breasts pressed against the cool surface. Her right hand slid down and he could tell she slipped her fingers under her short skirt. Michael stared as the dominant beauty fingered herself while he only got to watch her back, the see-through blouse, tight skirt and lovely laced boots burning into his memory as he realized what she was doing.

Suddenly she stopped, straightened and turned to face him. She raised two fingers that were obviously wet with her juices, the same two fingers that had, minutes before, been gently sliding in and out of his mouth. As he sucked, Michael felt large droplets of precum slide from his caged cock into the condom, adding to the collected drippings already accumulating there.

Michael licked his lips in anticipation of tasting those fingers once again. He moaned audibly when he realized that they were not for him, as Miss Marlene's smirking lips parted and she sucked them clean while he watched.

"Not today slut," she said when she finished cleaning her fingers, "and you have to get ready to go. Get dressed, wait at the door for me."

Miss Marlene strode from the room, her heels ringing on the marble. Michael, alone again, bit his lip with the frustration he was feeling and headed back to the door. Quickly he redressed, the shorts, t-shirt and sandals making it a very quick process. Miss Marlene came to him there. She handed him a new envelope, as soon as he took it Michael could tell that it contained the contents of the one he arrived with, but was now resealed with whatever Miss Marlene had added.

"Go down to the lobby and sit in the armchair beside the fireplace. Someone will get you."

"Yes ma'am," Michael replied as he stepped through the open doorway into the hall. Before he could turn around the door closed and the sound of the locking dead-bolt was a clear dismissal.

Michael followed the instructions he was given. Reaching the lobby he found it empty and he moved to take a seat in the indicated chair. He was still there ten minutes later when a hand dropped over the back of the chair to rest on his shoulder.

"Hello slut."

Michael looked down to see a pretty set of bright pink nails and watched as they slid downwards until one fingertip rested on his right nipple.

"Mistress Katie said I would find you here. Did you enjoy seeing Miss Marlene's new boots?"

"Yes ma'am," Michael replied hoarsely as the fingertip gently circled his hard nipple.

"Oh," the voice said brightly," no need to call me ma'am, you may address me as Miss Cassidy. Now come along, we have work to do."

"Yes Miss Cassidy," Michael replied as he stood and turned to see his new tormentress.

Cassidy wore a tight white nurse's smock, open to reveal a delicious amount of cleavage and short enough to show off her shapely legs in white stockings down to stylish white pumps with four inches of heel. Even with that added elevation, Miss Cassidy was still six inches shorter than Michael. She turned on her heel as soon as Michael faced her and walked through a nearby doorway. Michael hurried to catch up and found himself following the sexy nurse down a long corridor and then outside to a parking area.

Miss Cassidy was just getting into a red sports car and waved Michael to the passenger side. With his added height, she dropped the passenger seat to a nearly horizontal position to enable Michael to get in comfortably, then placed his hands at his side before drawing the seat belt over is body to secure him in place. Smiling, she undid his belt and slid his zipper to the bottom. her small hand sliding inside his shorts as she checked that his cage was secure and that his increasingly heavy balls were available for her teasing fingers.

"Comfy?" she inquired as she massaged Michael's cum filled balls.

"Yes ma'am ... uh Miss Cassidy," he replied quickly.

"Oh dear," Miss Cassidy said, "you seem to be forgetting things already."

Her small hand tightened on Michael's balls and she repeated her question more clearly."

"Are you comfortable slut?"

"Yes Miss Cassidy," he gasped, "I am very comfortable, thank you."

"Much better," she said as she stroked his balls softly, " let's hope we don't have any more lapses."

With that, she withdrew her hand and put the car in drive. She exited the parking lot and headed off along a circuitous route that quickly lost Michael's bearings. At each long stop, her hand slid inside his shorts again to massage his balls, her soft fingertips and slightly pointed nails ensuring a different sensation with each cycle.