Celebrity Sex Stories

Knightly conduct nears its end. Chapter 30.

Professor's Medieval Literature Humbled Through Infidelity and Feminization.

Spankmasters
May 10, 2024
14 min read
Chivalry is on Life Support Ch. 30chastitysissyhumiliationcuckoldfoot worship
Chivalry is on Life Support Ch. 30
Chivalry is on Life Support Ch. 30

Knightly conduct nears its end. Chapter 30.

At the same time, a new community started forming, which would request much of my time (and self-respect).

On a following Monday evening, I met Paul Betz at O'Riordans once more to confirm the schedule of my impending part-time servitude to him and Anna. Taking into account Luke's and Brooke's schedules (at that point, she was still serving tables at the restaurant three to four days a week), it was agreed that every Thursday afternoon I would show up at their condo with particular cleaning supplies and then clean it thoroughly from top to bottom. Additionally, I was expected to wash and fold their laundry for the week. It was determined that the third Tuesday of each month would be the target date for me to spend at least four hours at their apartment, preparing and serving them dinner and completing any other miscellaneous tasks assigned to me. Paul arrived with some of his and Anna's clothes for me to take to the dry cleaners that very day. I was to collect the clothes and bring them on Thursday when I arrived to clean for the first time.

Although it was unspoken, it was implied that I would be accountable for the costs of the cleaning supplies and dry cleaning (and, later, the food I prepared for them and their friends). This became evident when I first went to their condo. At 2,300 square feet (larger than Brooke's and my house), the condo was located in a luxury high-rise building that had been erected a few years earlier in a town adjacent to the college. This was undeniably the most opulent residential building in the area, featuring a large in-ground pool and gym on the third floor. I found that Paul was a trust fund kid from a well-to-do family in northern New Jersey. Similarly, Anna regarded herself as a princess. Paul's parents had even bought him the condo and his BMW. Thus, they certainly didn't require me to purchase anything for them; in reality, the financial sacrifices I made to fulfill their demands significantly reduced my professor's salary. I was a serf paying taxes to my lord and lady. And as the budding Medieval literature scholars they were, they even referred to me as such (on some occasions).

My servitude to Paul and Anna differed from my servitude to Brooke and Luke in numerous ways. Primarily, this servitude was involuntary. Although I may have been blindly infatuated with Brooke, my servitude to her and Luke was completely voluntary. Failure to comply with my vow to submit myself to her lover would have led to my loss of her, but that was still my decision to make. By contrast, I was being blackmailed by Paul. Not abiding by his directives would've very likely resulted in my losing my job, along with public exposure and mockery. Although these aspects eventually became insignificant (for reasons you will discover), they were extremely potent motivators for my early submission.

Another distinction was that my servitude didn't involve Brooke's direct participation. Anna definitely made her presence felt to me - often in humiliating and painful ways - but it was Paul who actually controlled me. Hence, while Luke was my primary master, he got that position solely due to his control over Brooke. In contrast, Paul's control over me was direct.

Their relationship with me was different for Paul and Anna as well. The other four submissives in their stable (all of whom I'd eventually serve alongside at various times) were their contemporaries. As Paul explained at our initial encounter at the pub, I was old enough to be their father. The fact that they had an older authority figure under their control was a constant source of amusement to them. This was demonstrated in some of their numerous nicknames for me: old man, professor page boy, professor serf, professor panty boy, Dr. Deviant, professor maid, Dr. Cuck, old loser, etc. Another distinction was that their relationships with their other submissives seemed semi-consensual, or at least closer in nature to my relationship with Brooke and Luke. They were driven by sexual desire, masochism, or possibly some warped form of love (or a combination of these) on the part of their supplicants. However, I was somewhat of an anomaly for the young sadists; perhaps they had concluded that some form of coercion was needed to ensnare the older prey they desired.

When the doorman inquired about my name on Thursday afternoon in the third week of November, as I stood outside their condo wearing jeans and an L.L. Bean jacket, mop and bucket in hand, I responded plainly with "Walter."

Who's this Walter?

Just Walter, please.

A Walter wants to see you. He doesn't want to give his last name.

The doorman was a skinny guy, around my age, wearing a traditional doorman's uniform like you'd see in upper-class areas of New York City. This seemed odd in a small city in Ohio but Neil might say it's a sign of my elitism.

He smirked at me. "You're probably the new maid. He said you should announce yourself that way to avoid any confusion. Apartment 11B. The elevator is around the corner." He spoke dismissively, implying the hierarchy of servants in the building.

When I rang Apartment 11B, Paul answered. Dressed in a t-shirt, sweatpants, and sweat socks.

I thought maybe this would be the moment when Paul would say, "Hi Professor Rollins, this is all just an elaborate practical joke. Thanks for being such a good sport about it. Welcome to our home. Let me get you a drink." But I knew that was unlikely.

This hope was quickly shattered when Paul said, "Get on your knees."

I looked at him in disbelief and said, "In here in the hall?"

"Yes, in here. I expect you to be waiting on your knees every time you come here until we open the door. You might consider buying some kneepads, since you'll be spending a lot of time on your knees when you're here."

"But what if one of your neighbors sees me?" I said, glancing around the hallway nervously.

"Who cares? We only have two neighbors on this floor and let me assure you, they've seen crazier things than someone kneeling at our doorway. They're chill with it. And none of them have any connection to the college."

I knelt and looked up at him, feeling a strange desire for entry into the apartment quickly.

"You may enter. Crawl on your knees." I did as he instructed. He then inspected the contents of my bucket: Murphy's Oil Soap, Lysol All Purpose Cleaner, scrubbing brushes, sponges. "What's missing? Our dry-cleaned clothes?"

"In my car, sir. I didn't want to wrinkle them with my hands full. Shall I get them now, sir?"

"No, you can get them later. Stand up and strip."

Bashfully, I took off all my clothes, leaving me in sheer white panties. The metal of my chastity cage was visible through the thin fabric. At that moment, Anna came down the stairs of the duplex condo.

"Fancy meeting you here, Professor Rollins!" she laughed.

I was embarrassed, wearing only my underwear and a chastity device, standing in a position of utmost submission before two of my students. Somehow, that was arousing and humiliating at the same time. My cock throbbed in its cage.

Anna was dressed like Paul but with tight, black yoga pants instead of sweatpants. She was about 5'8" tall and had straight, long blonde hair. Later, I learned she was co-captain of our college's women's volleyball team. In class, I'd noticed she was attractive but had stopped really appreciating her beauty after Brooke entered my life. But now, I couldn't deny that she was a gorgeous, sexy, young woman. I later came to discover that she was skilled at arrogance and spite. Such features were appealing to me, a masochistic individual.

She and Paul made an incredibly attractive and powerful couple, simply because of their ability to torment those who were submissive like me.

Source - Prompt: Write a sadomasochistic interlude. Ambiguously set in some university or college, the prof has been invited over by his students (both a male and a female). The prof brings his bucket of cleaning supplies. When the door is opened by the male student, he is ordered to kneel and stay kneeling until they open the door. When the prof attempts to explain why he's there, he is interrupted by the female student who suggests he is the new maid. The students send him to the elevator and have him take the stairs up. The male student instructs him to announce himself as "the maid" from now on to avoid confusion. The prof enters the apartment and carries out various tasks. The male student starts putting him through humiliating scenarios in front of the female student and the prof becomes sexually aroused by the situation. The female tells the prof how attractive she and the male find him. The prof is amazed by their power and then is told that they both have sadomasochistic tendencies. The prof discovers that the male student has a chastity cage on and is put in charge of maintaining it. The prof bucks, later, and starts to be punished by the couple. The prof then fantasizes about being in a more serious relationship. The prompter ends it saying "One day, Anna and Paul are sharing some tea, discussing their desires to control. Anna's mom thanks me for keeping her daughter out of trouble, unware that what's in the basement is a lot worse than an avid tea drinker, and the prof just chuckles." Based on the response's comments, the prompt was successful. It definitely spurred some emotional investment from the reader - even despite its brevity - as well as fantasy content. The were some creative responses exploring their power dynamic.)

I've been delving into a rather unique fetish gaining significant traction on the web lately. It's a twist or branch of the cuckold fetish, where compliant men are in service to what I call "alpha couples," usually consisting of young, good-looking, sporty, and dominant individuals. Typically, these men were physically weaker and fixated on the female partner of the couple with unmatched affection. They either find out firsthand after a breakup from the woman or simply understand from the very beginning that the woman won't consider them beyond friends (or even servicemen). The role for these submissive males extends beyond serving their beloved; they also cater to their female partners' romantic counterparts. Occasionally, the cuckold's devotion may extend to the dominant male partner, particularly when he is the object of their female partner's affections. This servitude can take the form of various chores, providing financial support, or even offering sexual gratification. The most intense cases, on either end, involve the cuckold being treated as a mere pet or even a servant. Sometimes, their love and adoration can become overpowered with a deep regard for the alpha male too, not just the female. It's an interesting parallel to old-fashioned romantic triangles and certain types of ménage à trois situations.

Case in point - Paul and Anna were textbook examples of this alpha couple scenario. I soon learned that two other submissives in their scrumptious ensemble upheld the mold of slaves to alpha couples. The proposition of Isaiah rather signified this submissive relationship; he was utterly enamored with Anna, but ardently revering towards Paul as well. The second example was a bit more peculiar, Cindy. A rare case of female servitude towards alpha couples, she was "friendzoned" by Paul, essentially embracing her subordinate status. This woman-cuckquean combination was distinct from drawbacks of typical cuckolds and cuckqueans, who have at least experienced a sexual connection with their beloved. Some might even say these ladies, if you could consider them cuckolds, were more pathetic than me. Luckily, Paul and Anna had a number of strategies to bolster their prominence over me.

"Howdy now, you not gonna say 'hi'?" Anna inquired.

"I've no idea how to handle you outside of the lecture hall," I began.

"Go on and address me as 'Princess Anna' or 'Princess' when we're here. Kneel and kiss both of my feet through your socks, professor."

I buckled and obtained back onto my knees, worshipping both of Anna's feet.

"Now Prince Paul's," Anna continued.

"As you wish, Princess," I responded.

I followed through with a kiss to both of Paul's feet, distantly recalling the pricey, spacious bedrooms at home.

"Let's give you a tour then, and you can start your maid duties. You may walk now, sir."

"Thank you, my prince."

They led me through the first floor featuring a large kitchen with upmarket appliances and granite countertops. There was a luxurious living area twice as broad as mine and Brooke's, a decent bedroom, bathroom, and an office room. We ascended the stairs to the second level, slightly less spacious than the first. The upper floor encompassed a large balcony overlooking the first floor, housing Paul and Anna's regal master bedroom and a massive bath connected to it. There was an added surprise, though - a dungeon, which Paul revealed upon unlocking a door to what seemed like a third, unfinished room. It covertly held a St. Andrews Cross, a type of punishment bench, and a sleeping cage. The walls were stacked with numerous riding crops, canes, paddles, and straps. Much like our entranceway at home, but far more expansive. Paul and Anna distributed these equipment sets between them, bolstering their dominance over me.

"Ms. Swisher?" I asked curiously. "Where does Ms. Swisher fit in all of this?"

"I'm not married to the man, stupid! He's my sugar daddy and I'm his sugar baby," Anna told me in a school-girlish tone. "You're just a bodyguard, a handyman, a maid, dealing with me being the princess and him being her King."

I nodded in return. "Got it."

This way, Paul retained control in the situation, ensuring my constant awareness of my place as a submissive in their lives.

Paul then opened a big closet with a tiny washer and dryer inside. I was thankful I wouldn't need to go to the downstairs communal laundry area of the condo to do their laundry. Although, following the tour, my first thought was that cleaning the entire house and doing the laundry in just two hours wasn't possible (and, indeed, it wasn't).

Paul stated, "After you finish cleaning, Anna and I will check your work. Any flaws will be noted in this journal. I'll note your mistakes here. You've already earned two for not referring to me as 'sir' when you arrived. We still need to determine punishment methods that won't be noticeable to Luke and your wife."

"How will he dress while cleaning, honey?", Anna asked Paul. Then to me, "Did you bring a maid's uniform with you today?"

"No, my lady."

"I liked that shorts outfit you wore at the Renaissance fair. You know, with the white tights. Bring that next time," she answered.

"I'll try, my lady. But the jacket belongs to my wife."

"I'm confident you'll come up with something. I doubt she'll miss it," Anna stated.

"With the chastity device, he should wear stockings and heels like Chrissy," said Paul.

Anna replied, "He's already groomed, at least. He's roughly the same height as Chrissy. I think I have a few unopened thigh-high stockings that Chrissy hasn't used yet. They'll look nice with his little white panties. I'll get them."

Anna returned with some sheer black thigh-high stockings. As I pulled them up my legs, the group watched, amused.

"He seems like he's used to wearing stockings many times," Anna remarked.

"He probably has," Paul added.

"Time to see if he fits into Chrissy's heels," she remarked, returning to the room with a pair of black heels. I'd never worn heels before, making me very wobbly. They were also tight and uncomfortable.

"These might be slightly too snug for him," Anna said. "I'll order a larger size for him."

"Well, your maid is free from wearing heels for now," ordered Paul.

"I like the 'professor maid.' I swoon!" Anna giggled.

I began by picking up their dirty laundry from their bedroom and starting a load of laundry. I then cleaned their master bathroom. For the most part, Paul and Anna relaxed on the sofa and watched TV while I cleaned. Occasionally, one of them would oversee my work, being quite critical.

"Make sure you clean behind the toilet. I'll be checking for dust on the back of the toilet, and I'd better not find any," said Anna.

"Yes, my lady."

"The only way to clean that thoroughly is on your knees," she commanded. I knelt and began scrubbing vigorously, mindful of her sharp gaze and my exposed panty-clad behind.

"He's more at ease tidying the floor on his knees than he is teaching at a podium," Anna remarked to Paul.

"He should teach from his knees."

"And take his own tests and quizzes too," Anna laughed.

"Those 64 you earned on your last quiz will somehow have to turn into a 100 by the end of the grading period," said Paul.

"We'll expect you to wear heels in the future," he told me.

"The maid professor. Oh, so clever!", Anna joked.

I began by collecting their dirty clothes from their bedroom and starting a load of laundry. I then cleaned their master bathroom. For the most part, Paul and Anna lazed on the sofa and watched TV as I cleaned. They'd intermittently come over to examine my work closely, often with critical comments.

"Ensure all areas behind the toilet are clean," Anna instructed.

"Yes, my lady."

"The only proper way to clean that space is on your knees," she instructed. And so, I carefully scrubbed, aware of her evaluating stare and my exposed, panty-covered rear.

"He appears to be more at ease cleaning while in a kneeling position than he does lecturing in a classroom," Anna joked to Paul.

"He should teach as a kneeling professor," Paul mused.

"And take his own exams and quizzes," Anna laughed.

"The 64 you've achieved in your last pop quiz must somehow become a 100 by the end of the grading period," Paul commanded.

"Alright, there's less than an hour remaining now, and you've got much more to accomplish. Hurry up." He smacked me hard on my rear. Anna chuckled.

I went about working as quickly as possible, focusing on completing the bathrooms, kitchen, and laundry. I was interrupted on two occasions when I was requested to provide the young prince and princess with glasses of water and snacks.

"I believe he should curtsy to us just like how Chrissy does when she brings us our drinks," remarked Anna.

"I don't know how to," I replied.

"Learn how. You're aware of how to utilize the internet, aren't you, old man?", Paul teased her. Anna chuckled again. "Get back to work. You'll convert into a pumpkin soon, and you have much more to finish."

I made great efforts, but unfortunately, I realized it was impossible to clean an apartment of that size within two hours to meet their precise standards. Although I'd attempted my best, Anna found two hairs in the master bathroom's shower and "unacceptable" residue behind the kitchen faucet. I had noticed it but couldn't eliminate it completely with the cleaning spray they provided.

Paul remarked, "He didn't manage to finish several aspects. The living room is full of dust. He didn't even touch the dungeon. It's improbable to expect it to be completed entirely in two hours."

Anna responded, "No issue. I'll inform Chrissy to join us tomorrow morning. Professor maid should just focus on the bathrooms, kitchen, and our laundry while Chrissy and/or Cindy care for the rest."

Paul then directed me, "Stand in front of us. At attention." I did so, in my underwear and borrowed thigh-high stockings before my seated young rulers. Paul lowered my underwear and held onto my balls, which were poking out from beneath the small chastity cage.

"Squeeze his little old balls, dear. Demonstrate who's the real boss.", he commanded.

Although they were small, they weren't geriatric. I was close to 40, but the age gap between us served as a significant part of their arousal while dominating me. This would remain a subject throughout the upcoming months.

Paul indeed squeezed my balls, making me stand on my feet to avoid pain. He held onto them firmly as he said to me, "That's five demerits. Two times for not addressing us properly. Two hairs found and debris on the counter. Please list them in the notebook, Anna. There's no more time today, so we'll handle them on the Thursday following Thanksgiving. During that time, you'll also cook us dinner for the first time. We won't feel hurried then. When you return, bring your finished writing assignment with you."

"Writing assignment?" I asked.

"Yes, punishment lines. You're required to pen down "I will never mention the trivial topic of academic honesty with Prince Paul or Princess Anna again" exactly 500 times. Ensure proper penmanship. Do you comprehend?"

"Yes, I do."

"Good. Now, dress up and obtain our dry cleaning. Leave immediately."

After retrieving the dry cleaning from the car, Anna told me with her bright smile, "I hope you have a delightful Thanksgiving, Professor Rollins!"

Responding as absurdly, I said, "Thank you, Princess Anna, Prince Paul."

I heard them both giggle behind the closed door as I headed towards the elevator.

I hurried past the doorman with a smirk, who was amused by the situation. Although Luke was away, Brooke would anticipate dinner when she returned from the restaurant.

As I said earlier, that November was incredibly hectic.

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