An Obedient Boy for Katherine Pt. 03

"Bess," Katherine cut her off, "What are you supposed to be wearing when you are at home?"

"Uh... nothing, Mistress."

"Then why don't you take a moment and remedy that."

"Yes, ma'am," Bess said quietly, "I will be right back, Mistress."

It took less than a minute, during which Katherine smiled at the thought of Bess' clothes flying in all directions as she obeyed.

"I am back, Mistress, please forgive me."

"You are forgiven my pet," Katherine said, "I hope that you can find time for a visit in the coming months, it's been too long."

"It has been far too long," Bess said, "and can I ask how Marcus is doing? His mom says he's doing alright but she never has details for me."

"He is fine, my dear, keeping on top of his studies, and doing some chores around here to help out."

"Does he have time for all of that with his job?"

"Oh, dear, perhaps you didn't hear, he got laid off soon after he started staying with us. The chores are a way to pay his rent and make a little cash on the side. It's been a beneficial arrangement for all of us."

"That is so good to hear. I was a little nervous about asking you to host him, but that was the only way he could afford to stay anywhere close to campus."

"Charles and I are glad to help. Having Marcus here has been great. There is one little thing I do need to tell you."

"Oh...?" Bess let the unspoken question hang.

"Yes, apparently, Marcus saw photos on your laptop. Photos of you with us, at one or maybe more of our house parties."

"Oh, my, God!" Bess spluttered, "When!? How!?.. Wait! How did you learn this?"

"He told me, dear. Perhaps we can say it was more of a confession. It was while I was doing some aftercare following a small introduction to bondage."

"What?!" Bess exclaimed, "You're training him!?"

"Bess!" Katherine's tone cut through the emotion Bess was projecting.

"Mistress..." Bess said plaintively, "How?"

"It all came about quite naturally my dear. There has been no coercion. He's a lot like you, you know. Submissive, obedient, eager to learn and experience, although he lacks that little explosive streak you keep displaying."

"I stand up for myself," Bess said with a hint of petulance.

"You, my dear," Katherine contradicted, "are a brat. You need constant supervision by a strong dominant and regular spankings to be kept in order. I suspect that you aren't getting the spankings you need."

"I apologize for my reaction, Mistress," Bess said softly.

"Did you meet the Talbots last weekend? I haven't heard back from them, but I suppose I would have if you didn't show up."

"I did," Bess giggled, "they are quite the couple for being old enough to be our parents. I am so glad you warned me to stretch my ass because he's got a huge cock and wanted it all the way up there. He was fucking me so deep in long slow strokes when his wife burst into the room and dragged me out by the ear. She put me over a bench and paddled me until I cried. All the time she was calling me a slut for trying to steal her man. When she finished she plugged my pussy and ass with fat vibrating dildos and took me back to her husband. She strapped him down and made me make him cum three times with my hands and mouth while she tortured me with the remote controls. It was great. I'm seeing them again in a few weeks."

Katherine laughed, "I thought you would like playing with them. You could always ask Mrs. Talbot to give you extra spanking sessions, you know, it's the appropriate therapy for brats. I hear she's quite experienced with floggers and canes, too."

"I may talk to her about that. You know a regular spanking schedule helps me stay on track."

"Oh, I know, dear," Katherine replied, "and thank you for having time to chat this afternoon."

"Thank you, Mistress," Bess said politely, "please tell Marcus I'm thinking about him, and if he really needs to talk to someone about what he's experiencing, I am available. Give him my love."

"That's okay, sweetie, he heard you."

"He's there?" Bess gasped, the rebellious edge immediately back in her voice, "wait, has he been there licking you this entire time?"

Katherine smiled and tapped Marcus' head. When he glanced up to meet her eyes, she held the phone's microphone closer to him.

"Hi, Aunt Bess, love you too. Hope to see you soon."

"God," sighed Bess, "and where is Charles might I ask?"

"Hi Bess," Charles sang out.

"Bess, before you go," Katherine interjected.

"Yes, ma'am," Bess' quieter voice signaled her surrender to the situation.

"Do you remember that dildo I gave you, the replica of Charles' cock that you could ride and practice deep-throating?"

"Yes," said Bess apprehensively.

"Well, yours was blue because it matched your fave nail polish at the time. I wanted your opinion on what color dildo I should have made for Marcus to practice with."

Marcus thanked his hours of practice maintaining a soft steady pace of licking because that exchange was almost enough to throw him off.

"Ohhhh," Bess moaned softly, "I... uh... the team colors for his high school were gold and black, so maybe those?"

"Thank you, Bess," Katherine said with a chuckle, "try not to dwell on that too much. We have to go. Love you. See you soon."

Katherine ended the call after Bess said goodbye to all three of them. She gently pushed Marcus' face back from her pussy.

Smiling down at Marcus, Katherine quipped, "It sounds like Aunt Bess wants you to have a big black cock for a toy to play with."

Laughing at Marcus' consternation, Katherine rose to her feet and stepped past the kneeling teen.

"Boys," Katherine announced, "it's time we retired to the living room. Marcus, don't clean your face. Go and get the wine ready for us. Charles, I intend to ride your cock until you fill me with cum, and then Marcus can lick me to orgasm. Any questions?"

In unison, Marcus and Charles responded, "No questions, ma'am."

Charles rounded the corner from the hallway into the living room and headed for the Stewarts' bedroom. With all the intervening doors open, Marcus could hear a shower start as he went into the kitchen and set out two wine glasses, and checked the fridge for an open wine bottle. He watched across the open living room as Mrs. Stewart followed her husband. Still wearing her thigh-high stockings, she carried her dress over one arm and her shoes dangling from two fingers of her other hand.

Marcus didn't have to wait long before Mrs. Stewart came back out and crossed the room directly in front of him. She motioned for him to pour her wine and hand it across the high counter separating the large kitchen from the living room area. After taking a sip, she stood there watching Marcus carefully.

"Now that Bess knows," she asked, "are you still okay with everything we are doing?"

Marcus paused before answering.

"Yes, ma'am," he said calmly, "I am okay with it. I like the way you make me feel. I want to be here."

"Good boy," Katherine said with a cheerful smile, "I think we have lots more to learn about each other and to explore."

"Thank you, ma'am, for everything you've taught me so far. I have been reviewing some of those links you sent me and reading them."

"Please be specific, Marcus, which links?"

Marcus blushed slightly as he added shyly, "The ones about anal play, Mistress, about cleaning for play, and plugs and things."

"Is that something you think you might want to try?"

Marcus squirmed, he hadn't expected his admitting to looking at the material would lead to being put on the spot like this.

"Yes, ma'am, I think so, with the way you lead me into new things slowly."

Katherine smiled, "I am glad to hear that Marcus. I do have some ideas."

Before they could continue, Mr. Stewart's voice filled the room behind them.

"And where's my wine? Are you two just going to stand there talking and ignore me?"

Marcus scrambled to bring the second glass and the bottle of wine around to Mr. Stewart.

"Sorry, sir...," he began

"It's okay Marcus," Mrs. Stewart interrupted, "he's just being himself. Just pour his wine."

Marcus did so and retreated to the kitchen to watch the Stewarts and to be ready to refill their glasses.

Katherine turned to her husband who wearing a short housecoat. The housecoat hung open and he was slowly stroking his already hard cock.

"Well," she said, "aren't you going to sit down?"

"I was thinking," he said with a grin, "that maybe you should turn around and lean over that sofa."

She laughed, "I know that look."

Charles tried to look innocent but couldn't pull it off.

"You want to take me from behind. I bet it's so you can fuck me while you imagine plowing Bess' tight little ass. Isn't that right?"

"Whatever gave you that idea?"

"Maybe it was the way you kept rearranging your hard cock while listening to her voice on the phone."

"Hmmm," said Charles, "you noticed that?"

"I certainly did. I know which ladies get that naughty cock twitching, and she is definitely one of them."

"Guilty as charged, my dear," Charles chuckled as he tipped his wine glass at Katherine.

"So, what was the rest of that image? Surely not just your cock and her tight ass to fuck? Were you also imagining her riding a cock in her pussy and maybe a third one fucking her mouth at the same time? Or were you imagining her licking me while you fucked her ass?"

"Now those are both delightful arrangements and we shall have to try them, again," said Charles, "but I was thinking about filling her ass with my cock and hot cum just before you slide a fat plug in there and then lock her in a latex maid's uniform to serve our guests."

Kathrine grinned, "I like the way you think. Perhaps two plugs under that uniform, and she'll never know who has the remote controls for the vibrators."

"And I like the way you think," retorted Charles with a matching grin.

"Well, I guess that's worth letting you fuck me from behind. After all, someone is waiting for a creampie to lap up."

Marcus' cock throbbed in its cage as he watched Charles' cock slide deep into Katherine's pussy with long slow strokes, knowing his tongue would be next in her pussy. Katherine encouraged him with descriptions of how she would tie Bess down for him to fuck and how she would have Bess suck his cock clean after they fucked. Giving in to the erotic imagery her words were painting, Charles was soon pumping his cum deep in Katherine's pussy.

Katherine folded herself into the sofa and twisted her body to catch Marcus' attention.

"Marcus, dear," she said with a singsong, "come fill my glass and lick me, please."

Charles stayed on his feet.

"My dear," he said, "I have a few errands to run, so I will leave you with your pet for a few hours."

Katherine lazily waved him away as she positioned herself for Marcus to crawl between her spread thighs.

"Take your time, Marcus," she said softly, "lick me clean and then lick me to orgasm."

"Yes, ma'am," Marcus whispered as he lowered his lips to his task.

A few days later Marcus got back to his room after a full day of classes. Four separate lectures broken up by a couple of free classes that he always used to review notes and study. His full days were tiring and just seemed to make the walk home seem longer. He looked forward to having a shower, a nap, a light dinner chosen from the prepared meals that he received from the Stewarts' meal plan, and if he wasn't still tired, another hour or two hitting the books. Mrs. Stewart had always assured him that these full class days would be dedicated to that purpose and she was very good at keeping her promise.

Coming into his room he dropped his backpack beside his desk and automatically started stripping, both to shower and because he was expected to be nude in the house at all times. Except, that is, when told otherwise or the cleaning ladies were coming. The sheer black booty shorts and matching sleeveless t-shirts may have provided a small bit of decorum, but they also hugged and emphasized his well-toned form, a fact that the cleaning ladies certainly seemed to have noticed with broad smiles each time they saw him. Marcus was unsure if they had realized that his cock was securely locked in its chastity cage each time they checked the cleanliness of his room. Sometimes, he suspected they knew.

They checked his room because Mrs. Stewart had taken the cleaning of the maid's suite where Marcus stayed off their list of chores and given it to him without any decrease in their compensation. They did, however, inspect it for Mrs. Stewart each time they were at the house, which was twice weekly. One day was while he was at classes, the other he was home and Mrs. Stewart expected Marcus to meet them for the walk-through. Sofia and her daughter Isabella, who was about Marcus' age, were a pair of very pretty and curvy Latina ladies. Marcus was never certain which one would appear at his door. Invariably they were dressed in tight black tops and leggings, an attire that was always a challenge for his composure. All too often, as Marcus cleaned his rooms in anticipation of their visit, he imagined one or both ladies closely supervising his cleaning duties, with the dusting brush they often carried changing in his mind to a teacher's ruler.

As Marcus peeled off his shirt and dropped it into his laundry bin, he turned as he grabbed the waistband of his pants to undo them and noticed the box on his bed. About the size of two shoe boxes side by side and of the same general construction, it was made of shiny black cardboard and the lid was held in place by a dark red ribbon around the box. Marcus paused, then decided to finish getting undressed and showered before investigating the box.

Soon after, Marcus exited his tiny bathroom having showered and having run a razor over his chin and genitals, a habit he had developed and maintained with each shower. He was following Mrs. Stewart's directions in doing so, and her comment that a stubbly chin would never be close to her pussy popped into his shower thoughts every time.

With the Holy Trainer chastity cage locked in place, Marcus hung the key up on the small hook beside his bathroom door. Its accessibility was a symbol of trust that he wouldn't use it when he wasn't supposed to. He had Mrs. Stewart's permission to unlock the cage each time he showered and shaved. She had emphasized that trusting him with the key was also a reminder that staying locked up until she decided he could have an erection, or an orgasm, was a symbol of his submission to her. Marcus had soon begun to find a level of comfort in the way the cage held his cock and balls and the slight tugging of its plastic form as he moved while it hung freely between his legs. Some days he found himself smiling softly as he imagined its snug feel was an extension of Mrs. Stewart's hand holding his genitals.

Cleaned and caged, ready in case the Stewarts called for him, Marcus sat on the edge of his bed and tugged at the free end of the ribbon to undo the bow. Under the ribbon was the shop's logo, The Playroom. Marcus ran his finger over the bold letters. The upper part of the "P" was a well-shaped breast in silhouette, the tail of the "y" was a curling whip, and the two "o's" were a pair of handcuffs. Marcus was slightly familiar with the local shop, He knew his chastity cage had been bought there by Mrs. Stewart. She had sent him to their information pages to learn about it when he was asked to make a decision whether or not to accept her control of his cock.

As Marcus lifted the lid off the box and saw the contents, his brief conversation with Mrs. Stewart across the high kitchen counter came rushing back. He noted that there was a large pump bottle of "Thick Water-Based Anal Lube." He picked it up and stood it up in the overturned box lid. Next, he lifted out a trade paperback titled "Anal Sex Basics." There was also an anal douching bulb, a set of three small straight dildos with flared bases, and a slightly thicker bulbous anal plug about four inches in length with the body slightly thicker than the third training dildo. Marcus swallowed nervously as he considered the direction this was taking. He had admitted to Mrs. Stewart that he was intrigued by thoughts of anal play and now he had an introductory toy set to explore. As he flipped through the book, he could feel the beating of his pulse inside the chastity cage.

Reminding himself that he should be studying that evening, Marcus put all the items back in the box for the moment. Popping a meal into the microwave to heat on a low power setting, he opened his laptop on his desk and powered it up. He then waited to see if his screen would be ready before the microwave beeped. The laptop won, but only by seconds. Marcus clicked the icon for his email program and went to grab his dinner.

Wading through the usual daily spam which simply seemed unavoidable in a modern world, Marcus saw that he had two emails of interest, one from Mrs. Stewart and one from Aunt Bess. Taking a bite of his dinner, Marcus mentally flipped a coin to decide which to open first. He chose Mrs. Stewart's because, as he reminded himself, she was his Mistress now.

"Dear Marcus,

"I hope your day of class and your study evening have gone and are going well. By now, I expect, you have discovered and investigated the box I left on the bed for you. Miss Lacey, the shop owner, was quite delighted to help me put together the contents as an intro to anal play box for you.

"Take your time to review the book, I know it will cover much of the same material you have probably seen online. Experiment, if you are ready, with the smaller toys. Work up in size as you get comfortable with them, and as you do, practice inserting them for longer periods.

"We will chat about your progress in a week or two.

"Kinky dreams, I will see you in the morning,

"K.S."

A week or two, Marcus thought. If he was going to do this, he realized that he had better start soon."

The second email was from Aunt Bess. Marcus smiled when he saw that she had given it a pink background, a flowery script typeface, and far too many emoticons.

"Dearest Marcus,

"I really didn't know how to start this email. At first, I was going to apologize and beg your forgiveness for getting you into this. But I do know that Katherine... I guess you now know she is and remains my Mistress from long ago... would never force you into decisions you didn't want to make. She never forced me either, but she sure knows how to ask if I want things that take me right where she wants me... if that makes sense.

"I know you're old enough to make your own decisions... wow, I guess I never thought that little Marcus would ever be 19. I know it's an important formative time for you and your personal development, both psychologically and physically. I do also know that Lady 'K' won't rush things, so don't be afraid to take your time to make decisions on anything that's happening. Please? Okay?

"Anyway, hugs, and I do love you so, so, much. Please don't hate me. If there's anything you want to talk about I am here for you. (And I do mean anything. Really!!!)

"Love and hugs... and kinky little licks too... wanna wrestle like we used to?

"Your fave (and only) aunt, Bess (a.k.a. Mistress Katherine's pet girl)

"P.S. Your mom does not know anything, and I will not be telling her.

"P.P.S. I sent a copy of this to Lady 'K' because I promised her long ago "no secrets."

Marcus smiled. Even with everything they knew now about one another, Bess was still the corny, funny, sweet Aunt Bess he'd always known. And she has a twinge of guilt too, he thought. Marcus wondered if he could turn that into a burger and fries or another guilty pleasure meal when she visited. Saving both emails to read again later, Marcus turned to his dinner and reviewed his evening's study plan for upcoming assignments and tests.