An Obedient Boy for Katherine Pt. 09

Bess took a seat beside Marcus much as she had earlier, her hip in contact with his. Smiling, she looked down at the young man and place a hand on his chest.

"I told Katherine that I would check up on you," Bess explained, "and make sure you're doing okay after our playtime earlier."

Bess sensed Marcus' slide into an obedient state as soon as she laid her hand on him. She knew they were going to be okay even as their own relationship entered a new stage.

"Uh,... I'm alright," Marcus said, his voice low and barely hiding the moan he felt rising in his throat.

"That's good, sweetie," Bess said calmly, "your Mistress is very concerned that we don't rush things for you and she was thinking it might have been a little too much all at once like that."

"No,... uh,... it's okay," Marcus whispered, 'I,... I liked it."

"Only 'liked' it?"

"No," Marcus groaned, "more than that. I loved it. I wanted it."

His voice lowered, his demeanor suddenly one of shyness.

"I've always wanted it,... Miss Bess."

"I'm glad to hear that," Bess replied as her fingertips started to caress Marcus' nipple, "because I have so many things I want to do with you."

Marcus' eyes widened at that statement.

Bess' hand started to explore Marcus' exposed body, sliding from his hard nipples downwards to caress and cup his balls under the chastity cage.

"Spread your legs, sweetie,' Bess instructed calmly.

Marcus did so and gasped as he felt Bess' finger slide along his perineum and her fingertips tickle his asshole.

"No plug tonight?" she asked.

"No, Miss," Marcus answered, "not for sleeping."

"But you're not sleeping yet, are you," Bess asked with a grin.

Marcus could only shake his head in reply. Bess looked around the room, spotting the row of plugs and dildos that Marcus had arranged on the shelf over his desk. Before Marcus could react, she stood and moved closer to the desk. She let him watch as her hand went along the line of toys, touching them in turn as she considered which one to choose. Reaching the end of the line, her hand came to the Bad Dragon Chance Unflared dildo. Picking it up, she also grabbed a bottle of lube that sat on the shelf before turning back to Marcus.

"I think this will do nicely," she said with a smile.

A low moan escaped Marcus' lips as he watched Bess hold up the dildo, the largest toy on the shelf. Bess paused to grab the bath towel that normally sat folded on Marcus' desk chair and tossed it to land on Marcus' legs.

"You should put that under you to catch any dripping lube," she instructed.

Blinking, his mouth open but wordless, Marcus finally started to comprehend that Bess fully intended to fill his ass with the selected toy.

"Now, Marcus," Bess' tone was firmer.

Jolted into his naturally obedient frame of mind, Marcus lifted his hips and spread the towel under his ass and upper thighs.

"Better," Bess said as she stood over the bed, "now spread those legs and lift your knees toward your chest."

Marcus followed her instructions. A low moan rose in his throat. He'd shared his nakedness with Bess in video chats, and she'd seen him naked throughout the day, but none of that seemed to have the same carnal intimacy as exposing his asshole to her for her to penetrate with the thick dildo.

Bess sat at the end of the bed and turned her body to face Marcus from between his raised legs.

"Good boy," she said as her fingers began to spread the cool lube over his waiting asshole.

Marcus gasped at the slippery touch, and again as one fingertip easily penetrated him to the first knuckle.

"Oh," Bess exclaimed softly, "this good boy's ass is so ready to be fucked."

Bess moved to kneel between Marcus' legs. Working with determined efficiency, she lubricated the first few inches of the dildo and pressed the head tight against Marcus' asshole. And then she paused.

"Ask me to fuck you, slut boy," she said in a tone that filled Marcus with an ever-ready image of his teasing aunt.

"Please," he gasped, "please fuck my ass, Miss Bess."

"Well, since you asked so nicely," Bess smiled and pressed the toy inwards.

They were both slightly surprised at how ready Marcus was for the toy. Half of its length slid into his widening asshole before Bess stopped it to add lube to the rest of the shaft. Before continuing, she adjusted her position, placing the base of the dildo against her own pubic mound and steadying herself by holding Marcus' shins just below the knee. She leaned forward to add pressure to the dildo and pushed slowly, an inch at a time.

"Do you like the feel of my cock, slut boy?" she asked, her voice gravelly from her own arousal, "it's too bad we don't have a harness right here so that I could fuck you properly."

"Yes, Miss," groaned Marcus.

Bess pushed until the toy was fully inside Marcus' ass.

"When I come to take you home for the holidays, I want you to bring all of your toys. I will be keeping you plugged and caged under your clothes at home, and we might find a chance to play."

"I will bring them, Miss," Marcus said as he felt the dildo fill his ass deeply, "but mom will be there."

"Don't worry about her," Bess said with a smile, "she'll take advantage of any chance to be out in the evenings. After all, you don't think all those late shifts she picked up were actually to work at the restaurant, do you"

Marcus' eyes widened as he caught the inference in Bess' comment.

Bess laughed and thrust gently with her hips as she continued.

"She just didn't want you to know, and wouldn't bring her dates home while you were there. But she can now that you're out of the house. I also know she had the hots for some of your friends on the wrestling team, and they didn't all leave town as you have. She's probably fucking one of them right now."

Marcus moaned at the thought of his mom fucking one of his fellow high school wrestlers. All those who were in his classes had graduated and most had remained near home for jobs or further education.

Bess giggled.

"Maybe she's fucking him on your bed," she whispered conspiratorially, "just like this."

With each of her last three words, Bess pressed the dildo deeply into Marcus' ass.

"She... wouldn't... not like this" Marcus gasped.

"Oh, sweet boy," Bess laughed, "you men can be so oblivious. You don't think we're the only kinky people in the family, do you?"

Marcus moaned, his hips rocked and rose to match the thrusting of Bess' hips that kept the dildo buried in his ass.

Bess maintained a steady rhythm with her hips. She'd estimated her own positioning and the placement of the dildo in Marcus' ass just right. With each movement, the dildo slipped back and forth an inch or so, placing the ridge halfway along its shaft against Marcus' prostate and with it, she steadily took him closer and closer to a milking and a prostate orgasm.

Gasping softly at each thrust of Bess' hips, Marcus moaned deeply as he realized that he was experiencing a new level of erotic stimulation.

"Do you like that, slut boy?" Bess huskily asked with a grin.

"Yes... please...," Marcus gasped each word.

"Do you think you can cum for me?" she added.

"I don't know," Marcus whispered even as he realized just how close it suddenly seemed as a possibility.

"I told Katherine you were ready for this, but she wasn't sure. You're going to cum for me and this is how I will milk you for her."

"Oh,... Miss Bess," Marcus' moan was plaintive as he understood that his cage didn't need to come off for him to be milked.

A whole series of internet porn clips suddenly flashed through Marcus' imagination as he saw himself recast in their scenarios.

Bess continued the gentle thrusting of her hips to massage Marcus' prostate with the dildo's shaft. She'd discussed Marcus' milking routines with Katherine when she asked about his chastity cage rituals. Katherine had described how she never kept Marcus caged and unmilked for longer than a couple of days, and that every ejaculation was conducted under her supervision. Katherine had found that longer periods of chastity with other submissives had only served to train their cocks to be locked away, and the body reabsorbing sperm that wasn't ejaculated only meant that their loads did not noticeably increase in volume or intensity when longer terms of confinement were used. Katherine liked the idea that a regularly drained set of balls was always working to replenish the expelled cum. Agreeing with her friend that longer periods in chastity had such effects, Bess still promoted the idea that longer periods could also certainly increase the subject's frustration and anticipation of a need to be released. Katherine had laughed that Bess' intent was the subject's frustration and submission and that her own arousal at the former was the driving impetus. Bess had smiled and nodded in agreement with Katherine's assessment.

As Bess' motions with the dildo drove him closer and closer to an orgasm, Marcus' mouth fell open and he softly grunted and gasped with each thrust. His eyes were nearly closed as his sense of existence closed to center around the feelings of impending orgasm and the frustration of his cock's attempts to become erect.

"Cum for me, sweetie," Bess crooned softly, "Cum for Miss Bess."

Marcus moaned deeply. It was followed by a groan of almost anguish that lodged in his throat. He felt an overwhelming sense of relief from his loins but also the heightened frustration of an orgasmic release that was not attended by either an erection or the direct stimulation of his genitals.

Bess smiled as she watched the cum flow in awkward small spurts and seepings from Marcus' caged cock. She knew from past experience with others that his orgasm would not be attended by any overall sense of completion or satisfaction and that his sexual senses of anticipation and frustration would quickly return. It was exactly what she wanted.

"Good boy," Bess said to Marcus as she moved back to release the pressure of her hips holding the dildo in his ass.

Working quickly but calmly, Bess guided the dildo out of Marcus' bottom, adjusted the towel so that he wasn't laying in a puddle of lube as he lowered his legs, and went to drop the dildo in the bathroom sink. She returned to the bed and lay down beside Marcus with her head on his shoulder. Laying one hand gently on the center of Marcus' chest, Bess spoke softly.

"I hope that what we did today was okay, Marcus, I know that I can come on a little bit strong at times."

"Oh,... Aunt Bess... I mean, Miss Bess," Marcus blurted in a whisper, "it did seem to be so much at the time, but now it seems that it was everything I had been hoping for."

"Mmm," Bess murmured, "I am very glad to hear that, but you will need to talk to Katherine if you have any second thoughts after I am gone tomorrow. We need to know in case we should adjust our plans for the holidays."

"I will..." Marcus agreed, his voice trailing off.

"Relax, sweetie," Bess whispered, "I'll lie here with you for a few minutes, and when you are ready you can go get cleaned up again.

"Yes, Miss Bess, thank you," said Marcus softly.

Bess slipped quietly from the maid's suite as Marcus was having another quick shower. When he came out of the bathroom, he smiled at the way she had folded and set aside the towel and turned back his blanket and top sheet to await him. He woke to his alarm after a night of deep and dreamless sleep.

The following morning Marcus prepared himself for his daily morning meeting with Mrs. Stewart. As he showered, he realized that he didn't know what Bess' planned departure plan was, or even if she might already be gone from the house. Walking up the hallway toward the living room, he was met by the very unfamiliar sounds at that hour of people in the living room talking.

Marcus rounded the end of the stairs beside the hallway to find the Stewarts and Bess sitting in the living room enjoying their morning coffee. Katherine and Bess sat together on one sofa facing Charles on the opposite side of the coffee table.

Charles wore his usual working attire of casual slacks and a polo shirt. Katherine was wearing a pale yellow silk blouse, long-sleeved and with a high closed collar, over a grey calf-length pencil skirt. Her feet were bare. Bess was wearing black slacks and a loose medium-blue blouse. All three looked ready to get on with their day, a sign to Marcus that his usual morning meeting with Katherine wasn't going to include any sexual activity.

"Good morning, Marcus," Katherine greeted him, "as you can see we're all up early. Bess will be leaving shortly to drive to her conference."

"Uh... good morning Ma'am,... Sir,... Aunt Bess," Marcus greeted the group in turn.

Charles silently saluted with a lazy raising of his coffee cup.

"Good morning, Marcus," Bess said brightly, "I guess we're back to 'Aunt Bess,' are we?"

Marcus blushed slightly as the memory of his willing submission to Bess filled his thoughts.

Katherine sighed and patted Bess' knee as she shushed the younger woman.

"Please come over here, Marcus," Katherine said as she patted the empty space beside her.

Marcus sat beside Katherine as she placed her coffee cup on the table in front of her. On the table, a folded lady's scarf covered a low object beside Katherine's coffee cup. She lifted to scarf to reveal a low box, about eight inches square and an inch and a half in height. On the lid, Marcus could see the logo of the local adult toy store, the Playroom.

"Open the box, please, Marcus."

Marcus reached forward and with the fingertips of both hands at the sides of the box lid, he lifted it off and placed it to one side. A layer of tissue paper concealed the contents of the box and Marcus folded back the paper to reveal a smooth collar in deep red leather with a brushed steel buckle of matte grey.

"I was going to make this offer to you last night, but things got a little intense," Katherine said with a glance at Bess. I decided that it was better to wait until we all had clear heads this morning."

Marcus looked at the collar, mesmerized by the feeling of power over him that it represented, and then he looked up at Mrs. Stewart, unsure of the exact terms of the offer she was referring to.

Katherine smiled and stroked Marcus' back.

"What I am offering is that you consider accepting my collar as a step forward in our relationship, your submission to me. It is not a question that needs to be answered immediately. You may choose to accept, you may refuse without other implications and we can keep things as they are for now or negotiate changes, or you may ask that we simply postpone your choice to a later date."

"May I touch it?" Marcus asked quietly.

"Of course, you may," Katherine replied softly, "take a moment to think about your choice, and we don't need to make a decision right now."

"I expected...," Marcus' voice trailed off as he looked at the collar in the open box.

"... more ritual?" Katherine finished his sentence for him, and continued, "I have found that creating rituals may reinforce a sense of the importance of a collaring for some, but it also creates a level of expectation in that moment of decision that can lead to haste and, possibly, later regret. Think of this more of a proposal rather than an expectation of immediate commitment."

Marcus' fingertips stroked the smooth leather of the collar. His eyes were half-closed as he imagined how it might feel around his neck. His breathing paused slightly as he visualized the feeling of submission that might come with surrendering to the collar being buckled in place.

As the others watched Marcus become absorbed in his own thoughts while holding the collar, they chose to remain quiet. They all knew from past experiences that this was a point of delicate balance for Marcus and that any decision he made had to be his own.

Without saying a word, Marcus slid from his seat on the sofa to kneel facing Katherine. He held up the collar on his open hands and looked up at the older woman.

"Please, Mistress," he said, his voice a coarse whisper, "I have thought about this very much. Please, may I wear your collar?"

"Are you sure about this, Marcus," Katherine confirmed, "You don't want to consider this further?"

"I am sure, ma'am, very much."

Katherine smiled and reached out to stroke Marcus' cheek. She then picked up the collar, holding the two ends as she opened the circle of leather.

"Lean forward, slut boy," she said gently.

Marcus leaned toward Katherine and moaned softly as he felt the leather of the collar contact and wrap around his neck. He listened to the soft jangling of the metal buckle as the free end was fed through it and the touch of Katherine's fingers as she ensured that it would not be too tight.

"Up," Katherine whispered.

Marcus straightened up, still kneeling, and looked into Katherine's eyes. He breathed slowly and evenly, holding in a soft moan as he felt a renewed sense of her control over him and his own willing submission. In Katherine's eyes, he found a softness that he knew was a sign of the care she extended to her submissives, as she had to Bess before him, although he was also aware of her strength and readiness to control her sluts.

"Thank you, Mistress," he whispered.

Katherine stroked Marcus' cheek again as she spoke to him with a smile.

"Thank you, Marcus, I suppose this can now be part of your house uniform. The red of the collar will tell our guests that they must still ask me for permission to play with you. One day you may be given a green collar like the one Bess wore yesterday, that color identifies the wearer as a free-use slut for our guests."

Marcus' eyes widened at that information and he glanced over at Bess. Bess, ever the brat, winked and stuck her tongue out at the younger man. Katherine sighed at Bess' impertinence.

"No sense of decorum with your aunt, is there?" Katherine asked rhetorically, and then continued, "In any case, we all have to get on with our respective days. I am sorry we can't explore this further right now. To be honest, I expected a somewhat longer decision-making process, but I do appreciate the efficiency we've achieved. Please tidy things up here, Marcus, while I walk Bess out to her car."

"Yes, ma'am," Marcus replied as he watched all three stand.

Charles kissed his wife, hugged Bess, and headed for the garage. Katherine started for the front door, and Bess stepped toward Marcus.

Hugging Marcus tightly, Bess whispered to him.

"Congratulations, slut boy, and welcome to Lady Katherine's kinky family for real. I'll be back to get you after your exams, and I will be getting more of that sexy tongue and ass, both here and at home."

"Thank you, Miss Bess," Marcus said softly, "I will be waiting for you."