Jester Mask tugged on the chains that bound his arms above his head. It was just as futile as the last time. The raven-haired unicorn wasn't strong enough to break these chains by himself, and his horn had been clamped with an anti-magic shackle at the base. He'd tried to get his hands around the accursed thing, but the guards who had bolted it on weren't stupid. The best Jester could do was brush his fingertips over it, and there was no way he was getting it off like that. He was just left to stew in the darkness of his cell in the middle of the night, with no magic and no one to talk to.
With a frustrated growl, Jester rattled the chains loudly against the wall. This prison uniform was itchy, the air was damp, his arms were tired, and he didn't care to think about how long he'd be stuck like this.
"Hey!" Jester Mask cried out into the darkness of the prison. "I don't know what you pigs think you have on me, but this is cruel and unusual punishment! Let me out of here right now, or I swear, it'll be your heads!"
From out of the darkness, a guard stepped into the view, Illuminated one of the torches on the wall. Wearing the standard blue pelted uniform, a tan pegasus with chocolate hair twirled a key ring around her finger. "You really should calm down," said the guard. "It's not a good sign when a newbie makes too much noise on their first night."
Jester turned his attention to the guard, still sneering with contempt. "Who in Tartarus are you?"
"I'm Openbook Shutcase. Night Guard, Prisoner Division." She opened the cell door with the key, stepping inside and slowly closing it behind her. "But you can just call me 'Book.' Sounds much cuter, don't you think?"
Jester leaned forward, coming as far off the wall that his chains would let him. "Sounds like I don't care, Shutcase. I knew they were gonna send one of you pigs out to make me talk."
Book smiled. "And you're talking."
Jester's eyes went wide for a moment before his sneer came back, turning his head away from the guard. Book took a step closer to him, just outside the reach of Jester's legs. Sure enough, Jester tried to kick at Book but missed wildly, which just made him pout even harder.
"Now, Jester Mask. That is your name, right? If you just cooperate with me, I promise you'll have a much better time here at the prison. I know you work for a group that was planning a big robbery some time soon. So just give me a few details, and then we can have both a pleasant night. How does that sound?"
There was no response from Jester Mask. At least not besides his face trying to pout as much as he possibly could. He even stuck out his bottom lip, which just made him look even more ridiculous. Book smiled again, knowing how much fun this one was going to be. She took one step back into the moonlight streaming from the barred window, letting Jester see Book unbuttoning the first two buttons of her uniform. Jester's eyes fell exactly where Book knew they would: her ample breasts, which were already stretching out the front of her uniform. Jester could pretend he wasn't interested, but his eyes told a different story.
"I don't think you're getting the message," Book said quietly. With Jester's eyes on her, Book slowly slid the third button through its loop, sliding her hand down to show her cleavage in the moonlight. She even leaned forward a bit, smirking with her eyes gently narrowed on her prisoner.
"This could be... a very pleasant night."
Jester stared at Book's boobs. He had been expecting the guards to do all manner of things to him, but this was definitely not one of them. It took a few moments before he snapped out of it, pulling his gaze away from her chest to her face. "Ha. You think a pair of boobs is enough to get me to snitch? In that case, maybe I should call you 'Nutcase' instead, Shutcase!"
It was Book's turn to give no response. She didn't even change her expression. Jester went from smugly confident to terribly confused in the span of three seconds. "What's going on, Nutcase? You think this is funny?"
"No," said Book. "I think it's fun."
Book strutted closer to Jester, giving her hips a gentle sway as she walked, making her large breasts bounce in her uniform. Jester told himself he wasn't going to look, but it was impossible not to. Much as he hated to admit, this guard was drop dead gorgeous. As Book reached him, she slid her hand up to Jester's shoulder, slowly pressing her breasts into his torso. The softness of her boobs caught Jester's full attention, making him lean back against the cold stone wall. Book stood on the tips of her hooves, giving Jester's shoulder a gentle massage and humming as she worked herself against him.
If Jester's will was supposed to be made of iron, Book was eating through it like acid. Jester squirmed against the wall, rattling the chains that held his arms above his head. His horn uselessly sparked as he tried to resist Book's advances, but it was hopeless for him. He could see right through what she was doing. But damn if it didn't feel good. Book's massage of his tired shoulder was helping, and the rubbing of her tits against his chest helped even more. She slowly rocked her hips side to side, working her magic on the prisoner.
Jester took in a slow, deep breath. "This is fun to you?"
"Mm-hm!" Book's hand curled around Jester's shoulder as she fiddled with the rest of the buttons on her coat. Soon enough, all of them were unbuttoned, letting Jester see that Book wasn't wearing a bra. With a gentle grip on both of his shoulders this time, Book slid her boobs up to his collarbone, then back down to his chest.
Jester closed his eyes, panting against the pleasure, his prison-striped pants beginning to tent at the crotch. Seeing the tent starting to form in his pants, Book slowly reached down with her right hand, gently putting her finger against the tented tip and drawing a slow circle. Jester shoved his head against the wall, letting out a lustful grunt as Book's fingertip worked its magic on his cock. He took in sharp, deep breaths as he tried in vain to resist how good it felt. He was almost disgusted with himself about how much he enjoyed it.
"Oh, we can have so much fun together, you and me," Book whispered into Jester's ear. "But if I'm going to have some real fun with you Jester, then you'll have to be... Cooperative."
Jester sharply inhaled through his nose as Book slid her huge boobs off of his chest and took her hand off his crotch, letting him look down her open shirt at her jiggling tits. Book only tilted her head, keeping that same confident smirk on her face the whole time. Jester could feel his body giving way to the growing lust, but his mind kept screaming at him not to fall for it.
"Nnngh... N-No," said Jester, his voice wobbling. "I'm not gonna talk. You're not going to break me, pig."
Book smiled more. Standing on the tips of her hooves again, she leaned forward again, right up against his ear this time.
"Yes, I am."
Moving one of her hands to the back of his neck, Book got a firm grip on Jester, whimpering inches away from his ear. She worked her tits even faster against his chest, causing her jacket to slide open even further, the tan breasts bouncing across his torso. Her hips rocked forwards and backwards, taking Jester from on the wall to a half-inch off of it, and back again, her own crotch pushed up against his leg.
"Oh, fuck!" The last vestiges of Jester's mind that weren't clouded by his rising lust were screaming at him to find some way to get this horny bitch off of him before he let something slip. Too bad that every other synapse was screaming even louder to let Book have what she wanted. As much effort as she was putting in, she hadn't even really started yet. He could practically still feel her hand working over his dick, and she'd only used one finger.
"Jester... Please, Jester, please!" Book whimpered into his ear, panting her warm breath across his face. Her hand reached down as she worked her body against her prisoner, pushing the palm of her hand into his tent. He tried to thrust forward against her hand, but every time, Book's hand quickly slid just out of reach. Jester planted his hooves into the floor, humping almost with desperation, but Book was always too fast.
"Nngh! Oh my fuck! Unh!" Jester's mind fully clouded over. "Cold Hard's Bank! Mh! We're gonna rob Cold Hard's Bank!"
Book suddenly grabbed his tented cock in her hand, her humping coming to a quick stop. She kept her large breasts against his chest for the time being, hearing Jester panting to catch his breath. Jester moaned as she worked her hand across his dick through the fabric, screaming at himself in his own head about how he'd just messed up.
"I knew you'd cooperate with me," said Book in the same soft time she'd had before. "And now, I think you deserve a reward for your honesty." Reaching down to the front of his prison uniform, she unbuttoned it one button at a time, letting his chest be exposed. The incessant annoyance of that uniform finally out of the way, Jester opened one eye, watching Book work her tits over his chest again.
She reached her hand into his pants and started to tug them down. Exposing the large black cock and the mask cutie mark on his flank, she dragged the prisoner's pants down to his hooves, even letting her mane brush past his cock as another tease. Jester panted again as he watched Book take a step back, sliding her coat to the floor, now topless. She brushed her long chocolate hair aside to give him a good look at her full, smooth breasts in the light. After giving him a couple of bounces, she slid herself down towards his crotch, letting the bottom of her tits jiggle around the tip of his meat. Jester bit his bottom lip, pushing his hips upward towards her tits. But as he did, Book raised herself up higher, just so that her underboobs were always resting just against his cock.
Book's hand slid to the base of Jester's dick, working her fingers and thumb up and down from his base to her tits. The whole time, she just looked up at him with that same devilish smile on her face. Jester narrowed his eyes down at Book, recoiling his hips and slamming his cock upwards. It still wasn't fast enough, as Book pulled herself back before his cock penetrated her cleavage.
"Ah, ah, ah!" said Book in a singsong voice. "You're not the one in control here, sweetie. I am. And only I say when you get my tits."
Jester grunted in a mix of frustration and lust, slumping against the wall, his face red with blush. "Unh... come on, I've already talked... What more- nngh! What more do you want?"
"Everything." Book curled her fingers tight around the base of his cock. "You know you want this. You can't resist it. I can see it on your face. Oh, your dick's probably aching, it's so hard. But the only way I let you have it is if you talk. So talk. Tell me everything, Jester."
In spite of how sexy Book was, Jester felt intimidated. His heart was in his throat as he watched Book torture his cock with the promise of her beautiful body. He'd faced criminals with bows and arrows who didn't have him by the balls this much. Certainly none quite this literally.
Book licked her lips. "You know what's going to happen if you don't talk? I do. You'll be sitting in this cell with a raging boner for days. The moment your hands get free, you're going to be rolling your balls in one hand and jerking your gorgeous cock in the other, thinking about me. You're going to hate yourself for not pounding my huge... soft... bouncy tits with all you've got."
"F-Fuck... tomorrow night... Gonna rob it tomorrow night." As he talked, Jester felt Book's hand work his cock once again. Her boobs slid down more onto his cock. Achingly slow. He felt his flared tip surrounded by her warmth. He knew he was losing. He knew she was getting more power over him with every word. He didn't care.
"Gh! Eleven o'clock!" Book's hand slid from Jester's cock as her huge tits enveloped his meat. She rocked her boobs across his shaft, closing her eyes and softly moaning to herself as her hands worked her tits around the stallion's large dick. Jester's hands curled around the chains that held him to the wall, finally allowed to work his hips against Book's chest.
As she worked her breasts over Jester's meat, Book pushed against Jester's hips until he was up against the wall again. This time, Jester stopped moving, as he was told. He'd learned. Book hands worked around his hips to his legs before moving back to her tits, squeezing them together with the top of Jester's dick poking out from her tits.
"See? Isn't that better?" said Book. She let go of her tits, letting them bounce around his cock as she slid her pants completely off, sliding forward and kicking the pants back near her coat. Sitting on her knees, naked, Book licked at the tip of Jester's cock. He yanked on the chains above him, rattling them loud enough for the whole cell block to hear. She parted her lips, wrapping just the tip in her mouth, working her tongue against it.
"NNGH!" Jester's whole body felt tense as Book licked and sucked his cock, panting hard. His horn sparked once more, but it was still useless against his horn's bind. He slid his legs apart to make more room for Book, who was humming around his dick, swirling her tongue and kissing his tip. A beautiful woman was blowing him, and he'd never felt more helpless. He'd also never been more turned on.
Looking down, Jester met Book's eyes as she looked up. Book suddenly glared at Jester, making his jerk his head upward automatically. The sight made Book chuckle, giving his cock another hard lick. It was all she needed to see. Now she could stop pretending that this prisoner had any say here.
Just as Jester felt like he might explode any second, Book let Jester's cock slip free, slowly pulling her mouth away with a thin line of saliva between her lips and his tip. Her magnificent tits slid away from his meat, and she slowly stood, leaving her prisoner looking her square in the eye.
"So..." Book pressed her tits against Jester's chest once again. "Are we clear who's in charge here?"
Jester nodded. "Yes... Yes... You're in charge."
"Good boy. Now, answer this..."
Book took a hold of Jester's cock again, guiding him ever closer to her folds. He could feel how wet she was, even after she'd had her mouth on him. She pushed him against the wall, a little harder than before. "How do you get this?"
Jester didn't even try to move his hips. As much as he wanted to try and pound her right now, he knew it would be useless. "I talk."
"Good boy! Do I have to make you earn it? Because I could leave you blue-balled right now, and there would be nothing you could do."
"No! No, I'll talk!"
Book kept a hold on his cock, but slowly pulled her hips backwards, leaving his tip out of reach of her folds. "Will you? Because you've been holding back before you tell me what I want to hear. Do I have to really make you learn your place? I can get you screaming for me if I want to, pet."
Jester gasped. "I'll talk! I swear, I'll talk!"
Her lower lips slid back against the tip of his cock, making Jester breathe a little easier. "Give me names, pet. You give me names, you get this. You can do that, can't you?"
Jester closed his eyes. He knew he was as good as gone. No use fighting. "Raise Cain. Big earth pony, brown mane... He's the one in charge."
Book began pulling away from him.
"Ah! I mean, he's leading the robbery! You're in charge! You're in charge!"
Book moved forward, letting the tip of her pussy kiss his cock. He felt his tip rubbing between her folds, just barely away from being truly inside her. "Give me more names, pet! More!"
"Fuck! Mmh! Night Hawk, pegasus with a gold mane! He's the inside man who was gonna-- Unnnnhh!" Jester couldn't keep his focus as he felt Book's pussy push down his cock. She was tight. Her hands held onto his hips as she moved downward, inch by inch. She took it slow. She could stop any time she wanted. Jester's mind raced to get back in focus. He had to keep talking.
"Gonna- NGH! Gonna go in... t-through the... The window--UNH!" Book was moaning as she started to work her hips, rocking up and down against his throbbing dick. She was right. His cock ached, he was so hard. He tugged on the chains so hard, he swore they were going to snap in half. He braced himself against the wall.
"Gonna! S-Steal! All the money in the saaaaafe!" His horn sparked. He wasn't trying to escape her. He knew he couldn't. He just couldn't control himself. The way Book rocked her wide hips, the way Book worked her long legs, the way Book grabbed him in her tight grip. He was helpless to resist whatever she wanted to do.
Book moaned, keeping Jester shoved against the stone wall as she worked on his cock. Her tits kept rubbing into his chest as she watched him twist his head and moan for her. With her eyes narrowed, she flashed a grin, widening her stance and working her hips faster. Jester's knuckles turned white as he held the chains, panting and blushing.
"That had better be everything, pet! Mmph!" Book moved her hands to Jester's shoulders, getting a fierce grip on him. Her hips were pounding him into the wall, her tight pussy rubbing across every inch of his thick cock. "You don't lie to me! No one lies to me!"
Jester was so tense, he couldn't even move. "That's all I know! AAH! I swear that's all, mistress!"
Book's fierce glare seem to pierce straight through Jester. Even though he had only one eye open, Jester was panting, clutching the chains for dear life, terrified to move without her approval. Through gritted teeth, Book growled in lust, slamming her hips against Jester's crotch. Both of them could feel him getting close. He could hear his own heart beating in overdrive. She saw the sweat beads rolling down his red flushed face.
"Then give it, pet! Give me my cum!"
"Unh! FUUUCK~!" Jester arched his back, pulling on the chains. He came harder than he ever had in his life. He gushed the biggest load of his seed into the tight pussy of the dominant beauty, his lustful cries echoing in the dungeon. Book's tightness took in every drop of his cum as she buried herself deep on her prisoner's dick, bracing herself against his shoulders.
Finally, Jester released the chains, collapsing against the wall and gasping for air. Even with his arms chained to the wall, Jester's legs felt like jelly. Coming down from the high of Book working his cock, every muscle in Jester's body felt like he'd just run a marathon. Book slowly let go of Jester, sliding her way off of his dick, bracing her hooves into the ground. As much fun as it was working him over, she had an image to maintain.
With a sigh and a few quick moments to catch her breath, Book walked back to her uniform, getting dressed and adjusting her mane.
"Ah... You're fun." Book smiled over her shoulder at Jester. "Maybe I'll have to interrogate you some other time."
Jester opened one of his eyes, still left a naked sweaty mess against the wall. "But... I told you... everything."
"Oh, trust me, pet... There's always more to find out." She gave a gentle shake of her ass at Jester as she walked out of the cell, locking the door behind her and strutting away with a smile on her face.
Left half-naked and humiliated in his cell, Jester managed to wipe his sweaty brow on one of his sleeves, grunting with his cock still gently throbbing. The cool night air helped him calm down. But it couldn't stop him from thoughts of that gorgeous guard racing in his head.
"So that's what you found out?" Captain Doom Star sat behind a long wooden desk, her hands curled up in front of her face as she listened to the interrogator's report. "Eleven o'clock, tomorrow night at Cold Hard's Bank?"
"Yes, ma'am! The prisoner confessed to planning the robbery, and we have names and a location!" Book saluted with a smile.
Doom Star pulled out a quill and behind writing down a few orders for the rest of the Night Guard. She conveniently ignored the smell of sweat coming off of her. Doom Star didn't argue with results. "Good work, Book. Go clean yourself up and report back in an hour. There's this earth pony I've had brought in, and I need to find out what his gang's planning."
Book smiled, popping her hips to one side before giving another salute.
"I always get my information, ma'am."
Author's Note
This is a little outside my wheelhouse in that it's not hyper or macro, but pretty straightforward sex. But I just got the idea in my head, and I couldn't get it out.
So here you go.
