Mistress Katie Supervises Ch. 05

Finally, the car came to a halt in an alley behind a slightly industrial building. Miss Cassidy unclipped Michael's seat belt and got out of the car.

"Let's go slut," she said.

Michael got out of the car and caught up to Miss Cassidy as she unlocked a door, one of many similar doors along the back of low concrete block building. Stepping through, Michael waited for instructions as Miss Cassidy secured the door and then turned on lights leading down a white tiled hallway. She led him down the hallway and into an examination room, this section of the building obviously a clinic of some sort but apparently deserted and available for Miss Cassidy's use.

"Strip."

"Yes Miss Cassidy."

Michael removed his clothes again, and looked around the room as he did. An examination table was in the centre of the small room with a variety of cabinets on the surrounding walls. As much as it appeared to be a medical clinic there were none of the telltale signs of medical supplies or the usual posters one finds on their walls.

Following Miss Cassidy's direction, Michael was soon seated on the end of the examination table. Quickly she laid him back and, with his arms at his sides, drew binding straps across his shoulders, chest and hips. Raising his heels into gynecological stirrups that she swung upwards into position, Michaels legs were raised and spread, supported at the back of his calves and strapped around calves and ankle. Once he was secured in this new and exposed position, Miss Cassidy rolled a stool to the bottom of the table, as well as a tray of covered instruments.

Taking a seat, she started massaging Michael's heavy balls with her fingertips, each hand manipulating a testicle until her subject was moaning with lust and gasping at the pressure of her fingers created.

"These appear to be quite full," she said calmly, "I think Mistress Katie will be pleased. But we have more work to do to prepare you for her. Now be patient and you should enjoy this."

Michael tried to watch what she was doing but his position on the table, and his bondage, prevented any clear view. He gasped at her next touch, as cold wet lubricant was spread around his tight asshole.

"Shhhh, slut," Miss Cassidy said calmly, "it's only a little cold and it will warm up quickly."

With that she slid one slippery latex-gloved finger deep inside his ass. She smiled as he moaned softly.

"See, you know you want it."

Slowly she fucked him with one finger, then two and finally three. In. Out. Twisting them to work at stretching his muscles.

"Do you want my whole hand in there slut?"

"If that is what you desire Miss," Michael replied in a quavering voice as her hand toyed with his ass.

"Maybe next time," she said, "we have a few toys to try today."

The next insertion was a slender dildo, an inch in diameter and almost seven inches long. Very flexible, it bent easily as it slid into Michael's ass. He could feel the pressure of its inward driving head, but the smoothness of the shaft was producing a gentle stroking of his hole as it slid back and forth.

Next she lined up a thicker dildo, the rounded head stretched Michael's ass, eliciting a deep groan as it slid inside. The shaft, slightly narrower than the bulbous head, was formed into a series of ridges an inch apart. Almost two inches of head, and six inches of shaft ending in a handle for control. Slowly she drove nearly eight inches of dildo into his ass, the ridges serving to massage his sphincter as it opened and closed with the sliding ridges. With long slow strokes, Miss Cassidy fucked Michael for long minutes as the precum dripped from his caged cock into the condom. Throughout the use of this dildo in his ass, Michael moaned and shook within the bondage straps, but other than the moaning he remained silent during her treatment.

Michael gasped as the thick head of the ridged dildo slipped from his ass. He moaned softly as Miss Cassidy returning to massaging his asshole with her fingers. Pushing inwards with all her fingers, she gave her slut an update.

"I could do it slut," she said with a smile, "I could get my whole hand in there right now if I wanted to, I'd only have to stretch you a little bit more. But not today."

Miss Cassidy reached for the third toy on her tray. A flexible silicone string of beads. Each bead was an inch and a half in diameter and connected to the next by a half-inch thick silicone strand. Five heavy beads made a string almost a foot long, and the base of the string was a wide flat flange to ensure they wouldn't slip completely inside a slut's ass.

Lubricating the strand with a heavy anal lube, Miss Cassidy placed the first bead against Michael's prepared ass and slowly pressed in inwards with her small fingertips. As the fat bead slipped past his sphincter muscles it drew the next bead up to his hole. Smiling, Miss Cassidy repeated the process with each bead, until the last disappeared into Michaels' ass and the bottom flange sealed his hole.

"Well done slut," she said, "too bad we don't have a longer string of beads for your ass. But our time is almost up and I have to get you ready to go."

Working quickly, Miss Cassidy cleaned up remaining traces of lubricant before releasing Michael's bondage. She indicated that he should dress and then turned to finish storing her toys back in their designated cupboards.

Once Michael was dressed, she handed him a new envelope and issued her final instructions.

"Go stand out back, someone will pick you up."

With each step, Michael could feel the heavy silicone beads moving inside his ass. Slowly he walked to the back door and stepped out into the afternoon sun. The first thing he noticed was that Miss Cassidy's car was gone, and that he was alone in the long industrial alley way between the building and an unbroken fence line. After ten minutes he began to wonder if he was in the right place, but going back inside to confirm his instructions was out of the question. The door was securely locked.

After another ten minutes, as he was rocking on his heels to keep the beads moving gently, he saw a car enter the alley and approach him. He smiled as he recognized Mistress Katie's car.

"Get in slut, and lay back."

"Yes Mistress," Michael replied.

He moved quickly to the passenger door and as he reached in with one foot felt the beads shift unexpectedly. With a low moan he settled into the seat. Mistress Katie reached across and buckled him in again, once more securing his arms at his sides. Then she unbuckled his belt and slid the zipper of his shorts downwards. Her hand slid inside, and her nails dug into his swollen balls with enough pressure to bring gasp to his lips, and a smile to hers.

"Did you enjoy Miss Marlene's boots slut?"

"Yes Mistress," Michael said hoarsely.

"She tell me she wants to try your slut tongue. I bet you would enjoy that, wouldn't you?

"Oh, yes, Mistress."

"I bet you would. And did Miss Cassidy stretch your ass nicely? Did you like her outfit?"

"Miss Cassidy's outfit was very sexy ma'am, and yes, she did stretch my ass. I'm still very full from her visit."

Mistress Katie's hand slid down past Michael's caged cock, her fingers touched the base of the string of beads and she pressed inwards as she watched Michael moan and his eyes half-close in response.

"Yes I know you're full. Do you like you new beads slut?"

"Yes Mistress," Michael whispered hoarsely as she continued to play with them, "I like them very much."

"Mmmm," she replied, smiling, "you are such a little slut when you are getting your ass played with."

With that admonition, Mistress Katie put her car in gear and headed down the alley. As before, at each stop she took the time to continue teasing Michael's heavy balls. She seemed pleased by the collection of dripping precum that Michael had produced and was looking forward to teasing her slut even further.

After a long slow drive, the car puled into Mistress Katie's driveway.

"Inside slut," she instructed, "go to the basement and strip. I will be down shortly."

"Yes ma'am," Michael said quietly and moved to follow her instructions.

He waiting quietly in the semi-darkness, naked except for his cock cage. He wondered what games Mistress Katie had planned and how she would use her slut.

It didn't take long before he heard the sound of her heels on the stairs as she descended. His first indication of her closeness was her hands on his back as her nails traced the lines of his body.

"I hope that Miss Marlene and Miss Cassidy coaxed a lot of dripping from your cock slut, it has been a while since I fed you, hasn't it."

"Yes Mistress, quite a while."

Mistress Katie walked around her slut and stopped in front of him. Michael's eyes widened as he saw the tight leather corset encasing her body. Her breasts, nipples barely hidden by the corset's cups, swelled over it's confining leather. Below it she wore a short leather skirt, hardly long enough to hide anything. It certainly did not hide the eight-inch strap-on cock Mistress Katie wore. Thick, black to match her outfit, and realistically shaped, she smiled as she stroked it and looked up at Michael.

"See anything you like slut?"

"Yes Mistress," Michael moaned as his cock pumped more precum into the condom, "everything."

"Good answer slut, now follow me."

Michael followed his Mistress into the next room. Open and bright with lighting, the room's main feature was a heavy solid bench in the centre. Following Mistress Katie's directions, Michael was soon face down on the bench and strapped in place. As he took his position he realized it placed his ass in a convenient position for anything Mistress Katie might intend to do with it. The end of the bench required him to spread his thighs to place his knees on the padded supports and let his cock cage swing freely between his spread thighs. His head was similarly positioned for ease of access and a padded extension on the bench in front of his head rose another three feet at an upwards angle in front of his face.

"Comfy slut?"

"Yes ma'am," Michael said softly as he relaxed in the secure bondage holding him in place.

"Good boy, now try to be quiet for this next session, I don't want to have to gag you."

As Michael tried to figure out what she meant, the first sharp slaps of Mistress Katie's practiced hand fell on his ass. He moaned as his ass warmed to the flurry of fifty spanks she delivered. Then he inhaled slowly, trying to control his breathing as he felt her hands sliding over his reddened ass.

"Was that ok, slut? Or did it hurt to much?"

"It was ok Mistress," Michael said hoarsely.

"You were a good boy, now try to stay that way," Mistress Katie said as she stepped back.

The paddle she chose was about the size of a ping-pong paddle. Made of a heavy wood and half an inch thick, it added heft to the strokes she started delivering to Michael's ass without ceremony. He tried to relax and accept the punishment, wondering what he had done to deserve such treatment. Soon Michael was moaning steadily and gasping between strikes of the paddle as he tried to to breath regularly. Forty spanks of he paddle, twenty spread out over each asscheek were delivered quickly, though not quite as swiftly as her hand spanking. Again, Mistress Katie's soft hands slid over the warmed flesh of Michael's ass when she was done. She teased the base of the anal beads as she questioned her slut.

"Did you enjoy that slut?"

"It hurts Mistress."

"I know slut, but I enjoyed it very much. Don't you want me to enjoy our time together?"

"Yes ma'am," Michael whispered, "I do."

"You being a very good boy slut. I've been wanting to spank you thoroughly for a long time. We're almost done. Please try to behave. "

"Yes Mistress, I will try."

The many strands of the flogger burst across Michael's asscheeks in alternating downward strokes, first on one cheek, then the other. Each tip seemed to bite and leave a stinging reminder of its passage. Michael moaned deeply, his whole body shuddering in the bondage, his strength revealing its necessity. Ten strokes of Mistress' flogger rained down on each red cheek, leaving a thorough network of criss-crossing thin red stripes to decorate the rosy complexion left by the paddle. As the first tears appeared on Michael's cheeks, Mistress Katie's hands slid over his ass once more, caressing, comforting as she praised her slut for his strength and willingness to submit. Michael gasped for breath, trying to control himself under her gentler touch.

"Are you ok, slut?"

"Yes Mistress, I am," he whispered.

"You are such a good boy. Now we are almost done. There is one more step to this and your introduction to the spanking bench will be complete. Now if you don't think you can take it, we can stop and you can go home now. We can try again another day, but we will have to start again with the spanking. Is that what you want, or will you be strong for me and let me finish?"

Michael weighed his options. if he asked to stop, he would be sent away. He only needed to be strong for Mistress Katie's promised last step. Then he would see what else she had in store for him after a full day of teasing.

"I will be strong Mistress."

"Thank you slut. You are a very good boy, and this will soon be over. There are only five strokes of the cane and we are done."

Michael's mind reeled as she announced the last stage of his spanking. He had always tried to behave so that he would not be punished like this. But he knew that this was what Mistress Katie truly enjoyed, and he has promised to be good and accept her conditions.

The first stroke ran across the cheeks of his ass like a line of fire. Michael moaned deeply and his whole body jerked with the sudden flash of pain. Before he could relax and try to prepare himself a parallel stroke landed. After that, another three in quick succession as soon as Mistress Katie was ready and his ass steadied to receive it.

Michael was moaning steadily as Mistress Katie hands slid over his ass. She smiled as she felt the heat in his flesh, and wondered how much the beads had been moving in his ass while he fought the bondage of the spanking bench. She praised her slut for taking the punishment she knew he needed, and that he would be a much more obedient slut now that he was aware of the potential consequences. But, she told him, regular maintenance spankings are always good to ensure a slut remembers to behave and, she added, a proper punishments spanking would be much more severe than the one he had just experienced.

Mistress Katie slid her hands along Michael's body, keeping contact with him as he drifted in and out of the subspace state her cane had finally managed to place him in. She caressed his nipples and teased his lips, letting him suck on her fingers as he regained control of himself.

"Would you like a treat now slut? You've been so good for Mistress."

"Yes please Mistress," he whispered hoarsely.

She walked around the bench to stand behind him again. Michael felt her handling the cock cage as she slid the condom from around the confining tube, the tip of the condom held a liberal collection of pre-cum drippings. Before returning to the front of the bench, she ensured a fresh condom was in place to continue catching his drippings.

Returning to the front of the spanking bench. Michael watched as she straddled the extension in front of his head, and he realized it's purpose. It was fashioned to comfortably support another person, and place their genitals directly under the mouth of the slut strapped to the bench. Michael watched as Mistress Katie got comfortable, and then held the thick strap-on dildo in front of his mouth.

"I have a treat for you slut, lots of drippings, and I want you to suck them from the head of my cock. Will you do that for me?"

Michael looked past the dildo in front of his face, meeting Mistress Katie's eyes. Her fingertips stroked the side of his head as he answered.

"Yes Mistress, I will if that is what you want."

"You are such a good slut," she said as she started to drizzle the precum on the head of the strap-on cock.

Again and again, Mistress Katie coated the head of her hard cock with Michael's precum and then slid forward to let him suck it from the dildo. She smiled as she watched his lips begin to respond automatically to the advancing phallus, opening to wrap his lips around its head and suck his own juices from it.

"Do you like sucking my cock slut," Mistress Katie asked.

"Yes ma'am," her slut whispered in reply.

Mistress Katie smiled as she fed Michael the last drippings, smearing them over the head of her cock with her fingertips. She let him suck her fingers clean then slid the head of her cock into his mouth again, keeping it there long after he had sucked his juices from it.

As Michael kept sucking, his eyes closed, Mistress Katie slowly pulled back, freeing her cock from her slut's sucking mouth. Quietly, she slid from the bench and went to stand behind him. It was time for the next part of her plan.

Working carefully, she slid her fingers under the flanged base of the anal beads. Michael moaned as he felt his ass open to let the first bead slide out, then again as each one exited in a slow sequence that let his ass close onto the connecting strand before the next ball started to apply pressure as it was pulled from his ass. Mistress Katie smiled as she spread lubricant on her thick cock and lined it up on his empty ass.

Michael groaned as the thick head entered his ass. He moaned as the shaft held his asshole wide open and the head plunged deep inside him. Mistress Katie's hips soon rested against Michael's red and tender ass. She smiled as she gently raked her fingernails across the sensitive flesh and then started stroking her cock in and out of his ass. Soon she has established a comfortable rhythm, fucking her slut steadily as he quivers with submissive lust in her bondage. Soon drifting in and out of subspace, Michael remained one large undifferentiated collection of stimulated sexual nerves. His ass, his caged and denied cock, his hard nipples, his sucking mouth; he wanted to submit completely to his Mistress and let her take his body however she desires.

Mistress Katie saw this change and felt the shift in Michael's body as he relaxed and responded to he fucking. She smiled as she realized how deep in his submission he was. She was glad that she could do that for him. Slowly, she withdrew her cock from his ass. She kept her hands on him, talking to him softly to maintain closeness, letting him know he was not alone as his mind drifted along in his deep submissive state.

As she started to release his bondage, Mistress Katie nodded to a watching guest. Michael barely realized at first that two pairs of hands were caressing him. Mistress Katie's hands supported his head while he drank cool water from a straw, while a second pair of hands explored his red and well-fucked ass, bringing fresh moans of pleasure from his lips. When they decided he was ready, they both helped him slide off the spanking bench.

He slid to his knees on a cushion positioned there for him. Mistress Katie stood close and he touched her legs for balance. She reached down and slid his hands up to her strap-on cock, now cleaned, and watched as he stroked it for her. She slid the tip across his lips and smiled as he opened them for her cock.

But now she guided his hands towards her guest. Michael looked to the side as the women changed places and realized that Domina must have been watching his spanking from the start. Mistress Katie slid his hands to Domina's hips as Domina moved in front to support her slut boy. He felt her long skirt caress his body from his thighs to his chest. Domina's hand slid down to caress Michael's nipples, she smiled as he moaned and leaned into her touch.