Acts of Chivalry: Part V — the Sword and the Scabbard
Library. Study room. 4pm.
That’s her text. That's all. No greeting. No explanation. Just a time and a place.
You’re there at 3:55, your heart hammering against your ribs. You’ve rehearsed what you’ll say.
You’ll be firm. You’ll remind her of the deal. Challenges completed, humiliation endured, lines written, ice bath survived, biscuit frosted and eaten. You’ve done everything. You’ve been a good knight. You deserve your date.
You push open the door to the glass-walled cube.
Lily and April are already there. April is sitting at the table, a textbook open, but she’s not reading. She’s looking at her hands, her cheeks pink.
Lily is standing by the whiteboard, her arms crossed, a small, thoughtful smile on her lips.
She looks up as you enter. “Sweetie,” she says, her voice warm. “Right on time.”
You step inside, let the door click shut behind you. The seal of the room feels absolute.
“I got your text,” you say, your voice too tight.
“I know,” Lily says, nodding. “I sent it.” She gestures to the empty chair. “Sit. Let’s talk.”
You sit. April glances at you, then looks back at her hands. She’s nervous. Excited. You can’t tell which.
Lily stays standing, leaning against the whiteboard. She studies you for a long moment, her gaze calm, appraising.
“You’ve been patient,” she says finally. “I’ll give you that. Most guys would have given up by now. Or gotten angry.”
“I’m not most guys,” you say, the line sounding rehearsed even to you.
Lily smiles. “No,” she agrees. “You’re not. You’re… persistent. And you’ve completed every challenge we’ve set. The waxing. The confession. The lines. The ice bath. The biscuit.”
She ticks them off on her fingers, her tone conversational. “That’s five acts of chivalry. Five demonstrations of your willingness to… understand. To be vulnerable. To obey.”
She pauses. “So I think it’s time.”
Your breath catches. “Time for what?”
Lily’s smile widens. “For your date with April. You’ve earned it.”
Relief floods you, hot and sudden. You did it. You actually did it. You won.
April looks up, her eyes wide. “Really?”
“Really,” Lily says, nodding. “He’s proven he really wants to be with you. He deserves a chance.” She turns her gaze back to you. “But.”
The word hangs in the air, a single, soft period.
“But what?” you ask, your stomach tightening.
“But I’ll be chaperoning,” Lily says, her voice still warm, still reasonable. “April’s never been on a date before. And given your… history… I think it’s only prudent. For her comfort. For her safety.”
Your mind recoils. A chaperone? Lily? Sitting there, watching, while you try to work your magic on April? It’s impossible.
You can’t seduce a virgin with her best friend—her maid in waiting—sitting three feet away, smiling that knowing smile.
“That wasn’t the deal,” you say, the words coming out sharper than you intended. “You said if I completed the challenges, I’d get a date with April. A date. Not a supervised playdate.”
Lily’s expression doesn’t change. “The deal was a date. I’m not changing the deal. I’m just… attending. As her friend. To make sure she’s comfortable.”
“She’ll be comfortable with me,” you say, leaning forward. “I’ve done everything you asked. I’ve been chivalrous. I’ve been… whatever you wanted me to be. I deserve a real date. Alone. Fair’s fair.”
April is watching you, her lips parted. She looks torn—between wanting the fairy tale and wanting Lily’s protection.
Lily considers you for a long moment. Then she sighs, a soft, almost regretful sound.
“You’re right,” she says, her voice gentle. “Fair is fair. You’ve earned the date. And I… I’ve been overprotective. April’s a big girl. She can handle herself.”
She uncrosses her arms, steps away from the whiteboard. “Okay. You win. I won't chaperone. You and April. A real date. Her choice of activity.”
The victory is so sudden, so complete, that it leaves you dizzy. You did it. You stood up to her. You won.
Your mind is already racing—where to take April, what to say, how to get her alone afterward.
The old script kicks in, the player’s calculus: quiet restaurant, soft lighting, a little wine, a lot of compliments, a walk somewhere private, a first kiss that feels like a promise.
You can already feel April’s mouth under yours, her body soft and yielding against you, the final conquest at hand.
You’re so lost in the fantasy that you almost miss Lily reaching into her bag.
She pulls out a small velvet pouch. Red. The color of warning, of stop, of something precious and dangerous.
She sets it on the table between you with a soft thump.
“But,” she says again, her voice dropping to a confidential murmur. “There is the matter of your… condition.”
You stare at the pouch. “What condition?”
Lily tilts her head, her expression one of warm concern. “Your penis, sweetie. It has a mind of its own. We established that in the lab. It listens to me, not to you. It’s greedy. Impulsive. Unfaithful.”
Your face burns. “I can control it.”
“We've been over this haven't we?” Lily asks, not as a challenge, but as a genuine inquiry.
“Remember? He frosted a biscuit on command because I told him to. You humped a vibrator like a dog in heat because I encouraged it. You ate your own cum because I said it was a sign of gratitude.” She pauses. “That’s not control. That’s… surrender.”
You open your mouth to protest, but no words come out. She’s right. She’s always right.
“April deserves a knight who can protect her,” Lily continues, her voice softening further. “Not just from other men, but from himself. From his own… failure. She deserves a man whose body is as faithful as his intentions.”
She picks up the velvet pouch, loosens the drawstring. “So. You can have your date with April. Alone. I won't chaperone. But your penis needs supervision. A little house for him to sleep in while you court April.”
She upends the pouch over the table.
A device slides out, gleaming under the fluorescent lights.
It’s a cage. But not like any cage you’ve seen in porn, not the tubular steel shaft that look like medieval torture devices. This is different.
Sleek. Modern. Almost beautiful in its minimalist design.
Medical-grade stainless steel, mirror-polished to a high shine. The shape is a compressed dome—a pod, really.
Curved bars form a smooth half-sphere, barely an inch and a half long. A solid ring, thick and substantial, sits beside it. Tiny LED indicators dot the ring’s surface, dark now but promising light.
It looks like something from a sci-fi movie. Or a very expensive sex toy.
“This,” Lily says, her voice reverent, “is the Babysitter. Designed by Dr. Clarissa Anderson at the Westwood Wellness Center. It’s not a punishment, sweetie. It’s a… relief.”
You stare at it. Your cock, always listening, gives a soft, interested twitch.
“Relief from what?” you ask, your voice hoarse.
“From the burden of control,” Lily says, picking up the ring. “From the constant, exhausting effort of trying to manage something that doesn’t want to be managed. Your penis wants to misbehave. It wants to chase. It wants to hump and spurt and make messes. And you… you’re tired of fighting it. Aren’t you?”
The question lands in the center of your chest. You are tired. Tired of the constant arousal, the shame, the humiliating cycle of resistance and surrender. Tired of knowing that Lily can make you come with just her words. Tired of feeling like a passenger in your own body.
“This,” Lily says, holding up the pod, “takes that burden off your shoulders. It contains him. It keeps him safe. And it keeps April safe from him.” She smiles. “It’s the perfect babysitter. Silent. Unobtrusive. Always on duty.”
Your mind is screaming. No. No way. Not happening.
But your mouth says, “How does it work?”
Lily’s smile deepens. She knows she has you.
“The ring goes behind your testicles. The pod fits over your penis—when you’re soft, of course. It compresses him into the small space, keeps him snug and contained. The two pieces lock together digitally.” She points to a small, seamless seam on the ring. “The lock is keyless. Code-based. And it has sensors. It monitors… activity. Arousal levels. That sort of thing.”
She sets the pieces down, reaches into her bag again, and pulls out a sleek smartwatch. “This pairs with it. The keyholder watch. I’ll be able to see your… status. In real time. If you’re getting too excited, if your little guy is trying to misbehave, I’ll know. And I can… help.”
“Help how?” you ask, though you already know.
“The Babysitter has a vibration feature,” Lily says, her tone clinical. “Low-frequency pulses at the base of the cock, behind the ring. It’s designed to manage testicular congestion—to keep your balls from getting too full, too achy. But it can also be adjusted. For intensity. For pattern.” She meets your eyes. “Remotely. Via the app on my phone.”
The implication hangs in the air, thick and humid. She can make you aroused whenever she wants. She can make you leak. She can make you come, even while caged. Hands-free. Helpless.
Your cock is fully hard now, straining against your jeans. The thought of it—of being locked, of being monitored, of being stimulated by her command—is the most humiliating, the most arousing thing you’ve ever imagined.
“I’m not wearing that,” you say, but the words lack conviction.
Lily’s expression softens with pity. “Sweetie,” she murmurs. “You just argued with me for ten minutes about how badly you want this date. How much April means to you. How chivalrous you’ve been. How fair it is.”
She leans forward, her eyes holding yours. “Are you telling me now that you’re not willing to do this one last thing to protect her? To prove that your intentions are pure? That you’re not just another guy trying to get into her pants?”
The trap is perfect. You walked right into it. You made a passionate case for your own devotion. Now, to refuse the cage is to admit that your devotion is conditional. That you wanted the date for access, not for April.
You look at April. She’s watching the cage, her eyes wide with fascination and something else—something like hope. She wants this.
She wants you to be the knight who has the sword, even if the sword is in a scabbard. A chastity device. She wants to believe you’re that noble.
If you say no now, you lose your chance to fuck her. If you say yes, your cock will be restrained from trying to fuck her. It's a double bind. You know it. Lily knows it.
Your shoulders slump. “Fine,” you whisper. “I’ll wear it.”
Lily’s smile is radiant. “Good boy,” she says, the endearment flowing from her like honey. “I knew you’d see reason.”
She sets the velvet pouch aside and gestures for you to stand. “Come here. Let’s get you ready.”
You push back your chair and step around the table, your legs unsteady. Lily positions you facing April, who is still seated, her textbook forgotten. You’re standing close enough that your thighs brush the table’s edge.
“Pants and underwear down, sweetie,” Lily says, her voice calm. “To your knees.”
Your hands fumble with your button, your zipper. You push your jeans and boxers down in one awkward motion.
And there it is—your cock, already fully erect, flushed and curving up toward your stomach. A pre-cum glistening at the tip.
Lily steps behind you, her presence a warm pressure at your back. She looks over your shoulder, her cheek almost touching yours, and lets out a soft, knowing chuckle.
“Hello, little guy,” she murmurs, her breath warm on your ear. “Someone’s excited to see us.”
You close your eyes. Shame burns through you, but your cock doesn’t care. It throbs, eager.
“He’s too hard for the dome,” Lily says, her tone conversational. “The Babysitter needs him soft and sleepy. He won’t fit in his new house otherwise.” She pauses. “But he doesn’t want to be soft, does he? He wants to perform. He wants his treat.”
You don’t understand. “Treat?”
From her purse, Lily produces a single shortbread biscuit. She holds it in her open palm, just to the side of your hip.
“His trick, sweetie. Frosting the biscuit. He remembers. He’s been thinking about it ever since the lab. He wants to show off for April again. He wants to prove he’s still a good little fountain.”
Your stomach clenches. “I can’t… not like this.”
“You can,” Lily says, her voice softening with pity. “You just need to help him. He’s all worked up. He needs to finish so he can relax. So we can put him to bed.” She nods toward your erect cock. “Go ahead. Stroke him. Help him do his trick.”
You freeze. Your hand hangs at your side. You can’t move.
Lily sighs, a gentle, patient sound. “Would it be easier if I talked to him? Since I’m the boss of him.”
She doesn’t wait for an answer. Her voice drops to that intimate, coaxing purr you remember from the lab, aimed directly at your groin.
“Hey there, little performer. You see the biscuit? You know what to do, don’t you? You want to paint it. You want to make it all shiny and white for us. You want April to see how pretty you can make it.”
Her words are a physical touch. Your cock jumps in response, a thick droplet of pre-cum welling and falling onto your thigh.
“He’s listening,” Lily coos. “He likes that. He likes being the center of attention. Go on, sweetie. Help him out. Give him a little encouragement.”
Your hand moves as if pulled by strings. You wrap your fingers around your shaft. The skin is smooth, fever-hot. You stroke once, slowly. Pleasure sparks, sharp and shameful.
“That’s it,” Lily murmurs, her lips close to your ear. “He likes your hand. But he likes my voice more, doesn’t he? He’s getting harder. Fuller. Look at him, April. See how he swells when I talk to him? See how he leaks? He’s so eager to please.”
April is motionless in her chair, her eyes wide, locked on the movement of your hand. Her face is flushed, her lips slightly parted. She’s never seen this before. She’s mesmerized.
You stroke faster, your grip tightening. The sound is obscene in the quiet room. Your hips begin to rock in tiny, involuntary thrusts.
“He’s close,” Lily narrates, her tone warm with approval. “His balls are tightening up. He’s getting that needy little pulse. He knows his job. He wants to decorate. Go on, little guy. Show us what you’ve got. Frost that biscuit.”
With a choked gasp, you erupt. Thick, hot pulses of cum shoot through the air, splattering across Lily’s outstretched palm, coating the shortbread biscuit in glistening white streaks.
You keep stroking through the contractions, milking yourself dry, until you’re spent, shuddering, your mind blank.
You slump slightly, catching yourself on the table edge. Your cock, already softening, twitches in your hand, dripping the last few drops onto the floor.
Silence, except for your ragged breathing.
Lily examines her palm, the biscuit now glazed and dripping. “Perfect,” she says, her voice satisfied. “Excellent coverage. He really gave it his all.”
She holds her hand out to you. “Appreciation, sweetie. He performed beautifully. Now you show your gratitude.”
You stare at the mess in her palm. Nausea rises, but beneath it, that familiar dark current stirs. Your spent cock gives a feeble throb.
You lean forward and take the biscuit from her hand with your mouth. It’s damp, warm, salty. You chew. You swallow. The humiliation is absolute.
Lily wipes her hand on a your shirt, her expression serene. “Good boy,” she says, her voice warm. “Now he’s soft. Now he’s ready for his nap.”
She turns to April. “Ready, princess.”
April’s eyes widen. “Ready?”
“To help his little guy get cozy and snug in his new home,” Lily says, as if it’s the most natural thing in the world. “He’s your knight. You should be the one to… show him.”
April blushes furiously, but she nods, her expression a mix of terror and excitement. She’s never touched a penis before. And now she’s going to handle yours, fit it into a steel pod, lock it away.
Lily hands her the ring. “This goes behind his testicles. Gently. Make sure both balls are through.”
April’s hands are trembling as she takes the ring. She kneels in front of you, her face level with your groin. Your cock is soft now, spent, lying limp against your thigh. It looks small. Vulnerable.
“Go ahead,” Lily encourages, her voice gentle. “Take him in your hand. Guide him through.”
April reaches out, her fingers brushing your shaft. The touch is feather-light, hesitant. You suck in a breath. Her skin is cool, soft. She wraps her hand around you, her grip tentative. She’s actually touching you. Holding you.
Her blush deepens, but she doesn’t let go. She lifts your penis, guides the ring behind your balls. The steel is cool against your skin. She pushes gently, until both testicles are through, the ring snug at the base of your shaft.
“Good,” Lily says, nodding. “Now the pod.”
April picks up the pod. It’s small. Shockingly small. She holds it over the tip of your penis, then slowly, carefully, covers it. Your soft cock fills the space, compressed into the curved bars, the head pressing against the rounded end. It’s a tight fit. Snug. Constricting.
April aligns the pod with the ring, presses them together. There’s a soft click, then a faint digital beep. The LED indicators on the ring glow to life—a soft blue pulse.
“It’s locked,” Lily says, her voice pleased. “The Babysitter is on duty.”
You look down at yourself. The steel gleams against your hairless skin. The pod is a smooth, seamless dome, containing your penis completely. You can feel the weight of it, the coolness, the unyielding pressure. You’re locked. Caged. Monitored.
April is still kneeling, staring at the device, her hand hovering near it. She looks… awed. And aroused. Her cheeks are flushed, her lips parted.
“How does it feel?” Lily asks you, her tone conversational.
“Strange,” you whisper.
“It’ll feel normal soon,” Lily says, nodding. “Like a part of you. Your little guy is going to be so comfortable in his new home.”
She taps the watch on her wrist. “I’ll be keeping an eye on you. Making sure your little guy behaves. If he gets too restless, I can… soothe him.”
The threat—or promise—is clear.
She has you pull up your jeans, fasten them over the cage. The bulge is minimal, almost invisible. No one would know. But you know. You feel it with every step, every shift of fabric.
Lily gathers her things, loops her arm through April’s. “Your date is Saturday,” she says, her voice warm.
“April will text you the details. Dress nice. Be chivalrous. And remember…” She taps her watch again. “The chaperone is always watching.”
They leave you there, in the study room, the taste of your own cum still on your tongue, the weight of the cage a constant reminder between your legs.
You came here today thinking you’d won. Thinking you’d argued your way to a victory.
Instead, you’ve been fitted with a digital monitor that reports your arousal to the girl who owns you. You’ve been locked away by the girl you want to fuck. You’ve jerked off on command and eaten your own failure, again.
And you’re harder than you’ve ever been in your life. The cage doesn’t stop arousal. It just contains it. Compresses it. Makes it a silent, humming ache.
You stand up, adjust your jeans. The cage shifts, a cool, foreign presence against your flesh.
You’ve never been more humiliated.
You’ve never been more aroused.
The game is no longer about winning April.
It’s about surviving the Babysitter.
This is the fifth in a series about a knight, a princess, and the best friend who rewrites the rules of chivalry — one digital lock at a time.
Next: What happens when the caged knight takes the princess on her first date — and the chaperone in his pants reports every flutter of interest directly to the girl who holds the key.
Previously: Acts of Chivalry Part I | Acts of Chivalry Part II | Acts of Chivalry Part III | Acts of Chivalry Part IV
Thank you for reading. If you'd like to read more of my writing, please consider subscribing to my Substack: Responsive Male. It's free to join and you'll be notified when I release new content.
