Chivalry's Survival at a Critical Stage: Chapter 26

Inflicting humiliation and castration upon a Middle Ages literature instructor.

Spankmasters

May 2, 2024

11 min read

humiliation, chastity, cuckold, spanking, Chivalry is on Life Support Ch. 26, sissy, butt plug

Chivalry's Survival at a Critical Stage: Chapter 26

Brooke and I seized Luke's absences, including his Sunday morning football practices, to have frank discussions with each other. We took advantage of these situations, doing various things. The conversation we had after the renaissance fair was particularly challenging.

Shortly after Luke departed, Brooke walked up to me, giving me a long, comforting hug. I'd be less than truthful if I claimed I didn't sob. Both my ego and backside were injured, making me apprehensive about losing my position. Feeling extremely vulnerable, Brooke's display of empathy prompted me to breakdown.

She carefully helped me onto the couch and gently wiped the tears from my face with a tissue, saying, "I'm acutely aware that yesterday was incredibly challenging for you. I'm sorry."

"What should I do? Should I hand in my resignation on Monday to Benkins?"

"Are you mad? Of course not. It's crucial not to panic."

"But you witnessed what transpired. Two of my pupils observed me polishing Neil's boots on my knees, dressed in tights. I cleaned their footwear! Like a subservient fool. I'm confident they took photos, right? Then they saw me in the stocks. Surely at least one of them lashed me with that tawse. My buttocks still ache."

Surprisingly, I had not yet chosen whether to disclose Paul Betz's threat of disclosing me. I wasn't certain if my motivation for secrecy lay in the embarrassing nature of the revelation or because I was unclear on what he sought in return for his discretion. I strongly doubted his jest, however.

"My reputation will be utterly ruined. I'll be the laughing stock of the entire campus," I reiterated.

"Pause a minute. Consider the ramifications. Firstly, we were all at a renaissance fair. It centers around imagination, assuming roles. Remind yourself, you've committed yourself to this belief more deeply than anyone. Therefore, you were merely portraying a subjugated part. It's mainly about 'acting.' And I'm confident that Neil would vouch for that, if it's ever exposed to other teachers or students."

I grumbled, finding it challenging to construct a logical counterargument to her sensible words. Nonetheless, I held steadfast in my conviction that significant harm, potentially permanent harm, had occurred on the previous day, and I was unwilling to let it go so easily.

"But I was down on my knees shining their shoes! And I think I had an erection, which they clearly saw. They were hysterically laughing at me."

"No one cares about your diminutive erection, Walter."

"Thanks a lot."

"Ponder it like a performance in a play. This was merely a component. Do you believe comedians and actors don't endure embarrassing moments in dressing rooms and on stages daily, even visualizing erections? It's truly not a significant matter. If anyone brings it up, which I highly doubt, just remark on it. Humor is an extremely effective diffuser."

"I fear I've misplaced my sense of humor forever. Another taken possession by him."

"Oh, please. I'm confident that isn't correct. You're just upset, rightfully so. Occasionally, the game is more amusing than others. Yesterday certainly wasn't amusing for you, I understand. But I must acknowledge that I had a lot of fun. Neil is a fantastic guy. He and Laura seem to be genuinely enamored. And remarkably, he and Luke have become close friends. I'm pleased he'll be around more. But yes, I must admit that it was quite funny witnessing your reactions yesterday. Oh, and I heard your facial expression when Luke accepted your loan to your students. And when he secured you in the pillory. And your outfit was delightful. I genuinely meant your hips seem firmer. They're marvelously spankable, now." As she said this, she entered my sweatpants with her hands and grazed my buttocks through my mesh panties. I began to drool inside my chastity device.

I was eager to continue discussing my concern regarding the violation of my reputation at the college and in the community. However, Brooke had effectively forgotten our conversation as she found new ways to divert my attention. A significant contributing factor to my current predicament was the fact that I hadn't experienced sexual relief in over two weeks, a condition that can't be attributed to the day of the dinner party when Luke resorted to using a wooden spoon to stimulate me. I paused to wonder how often Neil was sexually active with Laura during this same period, especially since they weren't performing sadistic homoerotic acts involving pain and humiliation. While I wondered if Neil managed to exceed my pathetic count of zero, it was obvious just how low I'd sunk.

I broke the silence by asking for her assistance in unlocking me. "Please, would you undo and spank me? Maybe you took the key by chance?"

Exhibiting his authoritative dominance, Luke had occasionally hidden the key from me by attaching it to his keychain alongside his personal key. The sight was always a subtle reminder that he was the one controlling my virility and that he would decide when I was permitted to release my tension. It was both frustrating and arousing to beg for his permission each time, making me feel entirely owned by him. Oh how Luke appreciated watching me plead to use my own body.

"Kneel before me and remove my socks with your mouth if you want to be unlocked."

I took her advice, proudly admiring the key hanging from Brooke's ankle as I knelt and began to remove her sock. I inquired about the possible whereabouts of the key.

"You're fortunate. I think you've earned an early release from your chastity device this time. No one needs to know about it."

"Thank you, My Lady."

She instructed me to appear as though I were servicing her feet. "However, before you remove it, make sure to kiss every toe on my other foot as well."

While I was slightly apprehensive about this seemingly elaborate request, I quickly followed her order. After handing the key to Brooke, I enquired about a point that had made me uneasy throughout our interactions. "But didn't Luke explicitly specify that we must ask him for permission before we masturbate, or when you...touch me?"

"He has such a kinky side, I just love the way you beg him for permission to masturbate. It's very sexy. But since he doesn't need to be aware, it'll be our little secret."

I hesitated. "But what if Luke returns home before we're finished?"

"How could he discover it? He won't be back for at least two hours."

With the key restraint removed, I felt an impressive sense of relief as I stood before Brooke. My erection immediately became noticeable. Brooke fetched some nipple clamps and a blindfold, encouraging me that it was only a matter of time before we resumed our activities. First, she fastened the blindfold on me before carefully squeezing my nipples to prepare them for the clamps. The pain stung for a brief moment as she attached them, but eventually, I managed to override it.

"Lie across my lap now." She informed me as she lowered the blindfold and proceeded to tug down my panties. The cool, wet object she held up to my anal opening startled me. "What are you planning to do?"

"Calm down and relax," she instructed, "enjoy the sensations as I press this cold, wet swab inside you."

I hesitated, but then proceeded as instructed. The result was an unfamiliar sensation that was jarring given the duration of my chastity. Thereafter, Brooke pulled up my panties while I emitted a slight sound of discomfort. She then brought forth some nipple clamps and a blindfold, encouraging me to move to her lap. The blindfold was selected first, followed by some tender nipple squeezing to ensure they were tightly fastened. "Spread across my knees, my good boy," she said with a seductive smirk. Once I was in place, she held a cold and moist item close to my anal opening. The environment elicited a reaction from me. "What are you intending to do?"

"Relax and soak in the feeling of this cold, moist object, my dear."

Unsure of whether she meant to insert it, I hesitated once again. That didn't last long, though, as, I found myself swayed by a combination of curiosity and fear when she proceeded to move my panties down. Fear overwhelming me, I jittered as I felt the presence of the cold, humid insertion, unaware of what she intended to do with it.

"It's a butt plug and some lube."

She was guiding it inside her carefully.

"Ouch, stop! It hurts!"

"Relax, honey. It's a beginner's size. Even smaller than a baby carrot. Think of how it feels when Luke enters you from behind. His penis is at least five times larger than this toy."

"Yeah, but you like it."

"Yes, but it still makes me wince. I think you'll enjoy it too if you just learn to relax."

"I feel so full."

"Perfect. I might just make you wear one of these around the house when doing chores. Maybe even in public. As we gradually increase the size, your anus will stretch like mine has. Now, you have a tight ass, what they call a 'tight anus'." She slapped my ass softly. "You'll grow to appreciate it. According to what I've heard, men can experience a prostate orgasm while wearing a butt plug. This can open up a lot of new opportunities for you!"

"Do I get any say in this?"

"Nope, not really. Now, do you still want that spanking? Your ass is still quite sensitive."

"Yes, please. But don't hit too hard, please."

"You are quite a masochist, aren't you?"

She pushed my pants up and started spanking me softly, alternating between my two cheeks.

"So how do you feel now, my submissive doll? Your nipples are sensitive, your ass is filled, and I'm warming it up for you. You'd better not ejaculate onto my sweatpants."

"I'll try my best."

"Get up for a moment." After standing, Brooke took off her sweatpants and ordered me to lie across her legs, bare. She resumed spanking me.

"Your buttocks are looking tighter. That daily workout and squats Luke makes you do are showing results. I might just have to buy a strap-on and make you your very own anal angel. What do you think? Would you like that?"

"Hmm, I'm not sure. Maybe."

She smacked me a bit harder. "Consider it. I'll make you wear a corset, thigh-high stockings, and a garter belt. Then I'll take you from behind, like a sex slave. Perhaps even Luke will want to claim you. That will really show you what 'full' truly means."

"No, please. Not that. I'm not gay."

She laughed. "Not gay? You're on all fours in panties and I'm spanking you with a butt plug shoved inside you. What do you call that?"

"It's a humiliating situation. I want to be your slave, not Luke's."

"We'll see about that." She hit me harder. Just then I heard a car door slam.

"Oh my God, is it Luke!?", I exclaimed, scared.

Brooke quickly pushed me off her lap and dashed to the window to peek through the curtains.

"It's Kevin. Quick, put your pants on!"

Kevin, who was Luke's half-brother and a coworker, had dropped by unannounced. They had worked together in the basement and I had experienced him a few times before. I knew he knew about my submissive role as I'd been ordered to serve him and his coworker sweet tea. This man showed disdain towards me.

"Hi, Kevin." Said Brooke. "Luke's not here. He's at football practice."

"Hey, Brooke. Todd." He greeted me. "I'm not here to see Luke. I suspect I left some tools down in the basement."

"Sure, go right ahead. Help yourself to a drink while you're at it."

"Thanks, Brooke. How have you been, Todd?" Kevin sat back in the recliner opposite me on the couch. [

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