Mistress Katie Supervises Ch. 01

Three weeks. It had been a long three weeks for Michael since his last orgasm. Since Domina had strapped him to the bed, teased and milked him to an intense orgasm. She'd eased the thick prostate massager into his tight ass and used it to heighten his arousal. Smiling as his cock throbbed and dripped, while she played with only his nipples and his ass, teasing him just the way she knew he needed. Finally she'd lowered her mouth to his dripping cock and sucked his load into her mouth. But she did not swallow it. She never did. As soon as he came, even while his muscles were still straining against the ropes from the intensity of his orgasm, she kissed him. Her strong tongue pushing his own hot cum into his mouth. Submissively, obediently, he accepted her kiss. Lovingly he sucked her thrusting tongue to clean it, consuming every drop of his fluids.

But that was three weeks ago. As he knew she must, Domina's attentions had returned to her studies. And Michael was permitted to play on line with Mistress Katie. Katie knew all of his secrets and kinky desires. She knew what was in his toy box. And she knew that Domina let him chat, and that he was required to provide his chats to Domina afterwards. Katie also knew that she when she played with Michael, he was to be in locked in chastity cage.

Mistress Katie also enjoyed making Michael ride an anal plug when she teased him in chat. She knew what plugs he had to choose from, and how to guide him to new and larger toys as she took his arousal to new heights. But she had also added one more little detail. A dripping slut's cock can be so messy. So Mistress Katie required Michael to wear a condom inside his chastity cage, capturing every drop of pre-cum during hours of hot chat.

There would be no orgasms in that condom, because those were denied by Domina. But sometimes, after long hot sessions, the combination of desire, arousal and a slut riding his prostate massaging plug, that condom might receive a large helping of fluids when conditions came together to drain him completely of his prostate fluids. Mistress Katie enjoyed taking her slut to that point of submission. Teasing his mind and body until his involuntary riding of the plug took control and drained him dry.

Three long weeks. Not a single orgasm. Evenings spent in chastity and often in hot chat with Mistress Katie. Michael would choose no other way to spend his evenings when Domina's attention needed to be elsewhere without distraction.

Michael found the birthday card on his computer keyboard when he got home that Thursday night. As she often did, Domina had slid into bed before he came home late in the evening from one of his occasional work nights. Domina had celebrated his birthday with him earlier that day with a pleasant much out, so an extra card was a surprise.

He was refreshing his computer screen as he opened the card, and was pleasantly surprised to see the card's front image. A pair of very sexy heels. Open toed pumps, probably 4 or 5 inches in height at the heel. The leather in a bold black and white zebra print, with the edges of the sole edge a bright red, a colour that was matched in the slender heels themselves.

Tearing his eyes from the sexy shoes on the front, Michael opened the card. He quickly read Domina's note: "Happy Birthday Slut, you will find that Mistress Katie has some instructions for you. I expect you to behave for her. Love, Domina."

Michael felt a stirring in his balls. The slightest suggestion could be a trigger for a raging erection after so long without cumming, and he knew he wasn't appropriately prepared. Obediently, he put the card down, and diverted his thoughts as he went to prepare himself for Mistress Katie's message which, undoubtedly, he would find on his computer. A few minutes later he returned to his desk, wearing a Curve chastity cage, with a condom encasing his cock within the cage's confining shape. He also inserted a prostate massaging anal plug because he knew that was normally expected of him when he was chatting on line. Mistress Katie called it having her slut "bagged, caged and plugged."

The weight of the Curve chastity device encasing his cock like a comfortable friend. The feel of the cage was less confinement than it was reassurance that he was following Domina's will. Chatting might be permitted, but only if Domina's terms were met. With her attentions needed for her studies, Michael was not about to risk his privileges by not following orders.

The prostate massager pressed in all the right places, or just the right place, as Michael sat in his desk chair. His legs spread to accommodate the bulk of the chastity cage. His chastity, whether controlled by the cage or, as it was most of the time, by his faithfulness to Domina, was most meaningful when periods of chastity were followed by intense and memorable orgasms under Domina's control. Knowing these sessions were to occur at the mercy of her own busy schedule ensured that other means of arousal only meant that his frustration and need would build slowly until those times she took him in hand for a long slow teasing session.

Michael turned to his computer and, as expected, found an e-mail waiting from his online temptress, Mistress Katie. He rocked slowly on the massager and felt his cock twitch in its confinement as he opened it.

Happy Birthday slut,

By now Domina should have told you to expect this e-mail. There are instructions for you in the attached file, but you are not to read them unless you are bagged, caged and plugged.

Thinking kinky thoughts,

Mistress Katie

Already prepared as his online Mistress desired, Michael turned his attention to the attached file:

Hello my little slut,

Domina has given me permission to play with you in person if I so wish, and I think it may be time to start preparing you for her absence this summer for her studies. Domina and I have decided that a weekly visit for your supervision should be sufficient, subject to change at her preference. There will, however, be a few rules for you to follow. Failure to adhere to these rules will result in losing your periods of supervision.

Firstly, and while this should not need to be said, I will do so for clarity between us. You will not masturbate or do anything to cause an orgasm for yourself while Domina is away. Any orgasms you experience will be at the express permission of, or caused by, Domina or myself.

Secondly, any time that you are home and alone, you will be wearing your cage. You will wear a condom inside your cage to catch any dripping whenever we chat on line, and you will insert a plug for our chats.

Next, I would like you to plan to write a new story for Literotica each week, you will be caged and plugged for any writing sessions.

You may expect that I will be visiting once each week to check on your obedience to Domina's wishes. I will test this by your response to various stimuli, assessing response time and intensity. With Domina's permission I may allow you an orgasm at these sessions if you prove to be sufficiently obedient. If I am not satisfied with your performance, I will be following Domina's expressed wishes to leave you locked up for another week until my following visit.

And one last thing to ponder my little slut, you will be consuming every drop of cum I decide to feed you.

Domina suggested you should have one opportunity to turn down this proposal, which you may do with an e-mail to Her and I within the next few minutes. If we do not see that e-mail (and I truly do not expect to), we shall assume that you accept this proposal, and I shall look forward to our next chat, and my first visit.

Think kinky thoughts slut,

Mistress Katie

Michael squirmed in his chair as his mind raced through the many possibilities the letter suggested to his kinky mind. Focused as he was, he started slightly as Domina's hands landed on his shoulders.

"Well," Domina said, "should I leave you to write a response?"

"No ma'am," he quickly replied, as her hands slid down his chest.

He gasped softly as her fingertips teased his hardening nipples. He squirmed on the plug in his ass and he felt a droplet of precum ooze through the constrained shaft of his cock. Michael groaned softly as his head leaned back against Domina's soft breasts. Her fingers tormented his nipples as the plug rubbed against his prostate, matching the sensual torment of her hands.

"You'll have to behave if you want Katie to visit," she said, "consider her visits a privilege you'll lose if you fail to follow any of the instructions she or I give you."

"Yes ma'am," Michael moaned, "I will behave."

"You'd better," his wife replied, "or I'll have her lock that cock of yours up and keep the keys until I get home at the end of the summer."

At the thought of the fate she mentioned, Michael drew breath sharply between pursed lips. The thought of such a long period of locked chastity as punishment was certainly something to be avoided and he was determined to be on his best behaviour between Mistress Katie's weekly visits.

"Now," Domina said, "I want you naked and on the bed in five minutes. You're going to spend the next little while strapped down while you think about Mistress Katie supervising your behavior while I'm gone."

"Yes ma'am," Michael responded immediately. Obediently he tagged his computer as 'away' and headed for the master bedroom The alternative designation 'Mistress bedroom' ran through his mind again as it did at such times.

In their bedroom, he stripped off his shorts and t-shirt. Wearing his locked cock cage, the prostate massager still in his ass, he quickly put on the soft pet collars they used as manacles. As each closing buckle snapped shut they were each one more small step further into the state of submission he enjoyed when he was under Domina's control. He crawled onto the bed and lay on the towel laid down the centre of the king-size mattress. As he knew he should, he spread his arms and legs to make it easier for Domina to latch the binding straps if she chose to do so.

Domina walked into the room a few minutes later. She smiled as she neared the bed and placed on knee up on the mattress. leaning over, she kissed her submissive husband on the lips, sliding her strong tongue between his parted lips. Michael moaned softly at her kiss, his eyes closing as he focussed on her touch.

Rising, Domina took the blindfold from the bedside table and slid it down over Michael's eyes. Next, she brought each binding strap up from the corners of the bed's platform where they were always ready for use and snapped them onto the d-rings on the wrist and ankle manacles he wore. She smiled as she thought of what the cleaning ladies must think when they swept around those straps every few weeks.

Once Michael was secured to the four corners of the bed, Domina sat beside his chest and let the fingers of one hand caress and tease his sensitive nipples. Michael moaned, his chest rising to meet her touch. Finishing the teasing of his nipples with a sharp pinch of each, eliciting a pair of gasps, Domina moved her attentions down his body.

She caressed his balls, the skin of his scrotum slightly taut from the constriction of the chastity cage's locking rings. She teased the smooth skin of his balls with he fingertips, and then very gently drew her nails over the shaved skin as she measured his reactions. Lastly her fingers slid downwards between his thighs. She grasped the end of the prostate massager and carefully rocked it inside his tight ass. She smiled as the effect of the massager on his sensitive prostate was immediately evident by the reaction of his hips and the straining of his confined cock.

Michael's mind was field with erotic images and thoughts as Domina played with his bound body. Her touch was sensual and soft, but he knew the strength her hands were capable of, and had experienced the spankings to prove it. He was lost in the imagery set off by her touch when she stopped and he felt her get off the bed.

Listening intently, Michael tried to determine what Domina was doing after she got off the bed. Was she choosing a new toy for his bottom? Was she getting the key to open the lock and release his straining cock?

The answer, as the next sounds he heard proved to him, were unexpected. He listened as Domina dialed the phone, the electronic beep of each number being pressed striking him as out of place compared to their past bondage sessions.

Michael felt Domina sit beside his bound body once more as she waited for the phone to be answered. Her hand returned to stroke and tease his hard nipples as she started to speak.

"Hello Katie, how are you tonight."

"Yes, he read the note .... no, you won't be getting any message asking not to play. He's decided he'll accept whatever we have in store for him."

"Oh he's very willing, he's right here beside me ... yes, just as we discussed, locked, plugged and strapped down. Would you like to see him?"

"Twenty minutes, that's fine ..... he's not going anywhere."

"See you soon sweetie."

Michael listened as Domina released the call with a press of a single button. Her fingers closed on one of his nipples and he gasped at the sharpness of her pinching fingertips as she spoke.

"Mistress Katie is coming to visit. If you behave like a good little slut, maybe we'll unlock that little cock and let him out to play. But don't think that opening that lock guarantees an orgasm, you can still end up back in your cage tonight .... and very frustrated besides."

"Yes ma'am," Michael whispered.

"Now," she said as she stood, "you just lie here and relax. Maybe we'll have a cup of tea before we come up."

Michael listened to Domina cross the room and heard the door close softly as she went out to wait for Katie.

Lying in the darkness afforded by his blindfold, Michael's mind reviewed the contents of Mistress Katie's note setting out the rules for his intended visits during Domina's absence over two months of studies away. He also thought of the many late chats he had had with his online Mistress, his straining cock dripping in its cage, and every drop collected by the condoms she instructed him to wear under the cage.

Michael licked his lips as he recalled the nights Mistress Katie had made him suck the collected precum from his condom after she had teased him for hours on line. And his ass clenched the prostate massager, feeling its intimate touch with each flex of his hips. While his mind was fully engaged with such erotic thoughts he occasionally felt a droplet of precum ooze through his constrained cock, adding to the juices already collected there since reading Katie's note.

He was caught be surprise when the door opened. He hadn't heard their approach in the hall and was slightly startled when the ladies entered and he heard Mistress Katie soft gasp as seeing him strapped to the bed.

"Well, doesn't he just look delicious," he heard Katie's soft voice say.

"Yes," replied Domina, "he is a good little slut, and ready to be obedient for his Mistress Katie."

Fingers suddenly stroked his balls, but he didn't know which women was touching him. He could sense them moving around him, and leaning over the bed, but unless they spoke he wouldn't know which lady was where. The fingers kept massaging his balls and another hand gently lifted the his cock in its chastity cage. He heard Mistress Katie's voice from between his legs.

"This is a fiendish little device, isn't it?" she asked.

"It does keep him under control," Domina responded, "and it's an effective reminder that a good slut lets his ladies control his erections, and his orgasms."

"Yes," Katie replied, "it would do that. Can we open it?"

"Certainly we can, all the better for us to monitor the effects of the massager in his bottom."

Michael felt the lock being opened that held the Curve secured on his cock. The cage portion slid off and he felt the locking ring the went behind his balls being opened and slid away. Strong fingers grasped his cock, which was quickly growing erect, and slid the condom from its head.

"I see we've been dripping like a messy little slut," Domina spoke, and then to Katie, "Would you like to feed our slut?"

"Oh yes," Katie responded and Michael felt her rise from the bed between his legs and move around the bed to sit beside him. But he couldn't see as she took the condom from Domina and deftly inverted it around the three middle fingers of her right hand.

"Open wide slut," she instructed.

Michael obediently followed her instruction and immediately felt those fingers, cased in the condom, and dripping with his own precum slide between his lips. She slowly slid her fingers in and out of Michael's mouth, feeling him suck the juices from the condom.

"He is an obedient little slut, isn't he?"

"And ever more so when he's horny and wants to cum," Domina replied.

As Michael continued to suck on Katie's fingers he felt Domina's hand slide between his legs. She grasped the massager and slowly moved its head back and forth over his prostate. The ladies watched the immediate effect it had on his cock as it grew to almost seven hard inches, the precum seeping from its tip and slowly running down the straining shaft.

"Look at the mess you're making," she said as she teased her submissive husband, "I don't know if Mistress Katie will want to supervise such a messy slut."

"Oh, I am sure I'll survive," Katie responded in the same light tone, "after all, he does know that messy sluts are expected to clean up their own messes."

"Yes, he does know that, it's all part of his kinky needs."

"Mmmmm," Katie said, "then we shall have to make sure he's well fed at least once a week if he behaves."

"If he behaves," Domina replied, "that will be the test. Well slut, will you behave for Mistress Katie?"

"Yes ma'am," Michael replied hoarsely as Katie slipped her fingers from his mouth to let him respond to his wife.

"Good answer," Domina said, and for that you might even get to cum today. Would you like that?"

"Yes please, ma'am."

"Then perhaps you should ask Mistress Katie, since I'm letting her control your orgasms once I'm away, you should start asking her whenever she visits us."

"Please Mistress Katie, may your slut cum today?"

Katie chuckled, "Perhaps little slut, perhaps, but first I want to see what toys Domina likes to use on you and after we see what effects they have, maybe we'll see if three weeks has been a good wait for you."

"Thank you Mistress," Michael replied as he felt a weight being placed on the bed beside his leg.

"Let's see what we have in this toybag," Domina said. She took a number of toys from the bag to see Katie's reactions until Katie responded excitedly.

"Oh, that one looks like fun, can we try that."

"Yes we can," Domina replied, "he likes this one."

Unseen through his blindfold, Michael wondered what toy they were discussing. Domina held a flexible anal probe. Molded in a single piece with a handle to offer greater control of the toy, the slender curving shaft ended in a rounded head designed for massaging a submissive's sensitive prostate.

"You'll find it to be quite effective for milking him drop by drop if that how you choose to play with him."

"Mmmmmm," Katie replied, "that does sound like fun, and it could be a long, slow torment for a little slut too."

Katie watched as Domina reached under his ass and slowly drew the prostate massager from his ass. Bright red in colour, she held it up to show Katie.