Piper's Price

by D. A. Maddox

  She showed him the picture, held it up for the cameras to see.

  She wanted to cry, and to touch herself.

  Instead, she knelt again, reached for the bottle at her belt. Robbie’s penis bobbed with expectation and desire. It was dribbling a drop of opaque white. “Prelim-jizz,” Officer Jenny had called it.

  She uncapped the bottle, felt the escaping cold from the frosted inside.

  And poured iced water over Robbie’s privates, doing all she could to block out his screams.

  Don’t listen, she said to herself. You have to stay in-character for another hour at least.

  “Back soon,” she said, standing, keeping her voice steady while Robbie hollered over her. She called to her friends. “Your turn,” she said. “First to make him squirt after that wins five bucks.”

  And she stomped off, keeping herself together until she was gone from the room completely.

  Chapter Twenty-One

  Besties

  Heather and Jasmine went to the A-frames in the second circle, but Robbie was in no position to see what toys they picked. All he could do was listen as they ran back and forth between them, gathering gear. He stared through blurred vision at the shadowed ceiling, at the cameras riding the wires. His scrotum, constricted by the cold, was as hard as frozen rubber. His cock, by contrast, was an upside-down capital “J,” deflating fast.

  At first, he’d thought Maddy had poured liquid nitrogen on him, or something similar, and was going to freeze his penis right off. It was a stupid thought—No permanent or lasting injury or scarring, he reminded himself—but it had happened so suddenly, and it had shocked him clear out of his wits.

  You’re going to hate me, she’d said. How much choice did she have over the punishments she would inflict on him? To listen to Heather and Jasmine, selecting their tools from the second circle, he figured quite a lot. But there was no hatred in his heart. He wasn’t even angry.

  That’s one more torture down, he said to himself. That’s how I make it, one at a time.

  They came to him from either side. Robbie kept his eyes on the ceiling until they set their things on the floor. He was afraid to see what they had brought with them, and he winced when something soft and wet was placed over his crotch.

  But then he relaxed. It was an almost-but-not-quite hot washcloth, and it was just what the doctor ordered. Heather had placed it, and now she patted it down so that the state and shape of his organ underneath was clear to behold. “For your pee-pee,” she said. “Better? You can talk. It’s okay.”

  “Yeah,” he said, his voice shaky and tremulous. “Thanks.”

  And, God, why did everything make Jasmine laugh out loud?

  But then Jasmine’s face hardened, a swift and terrible shift, as though she had just remembered something, and it pissed her off mightily. “That’s the last time we get a ‘Yeah’ out of you, little boy. Say ‘Yes, ma’am,’ or ‘Yes, Mistress Heather.’ Got that?”

  “Yes, ma’am,” he quickly said, cursing himself for a fool, for not anticipating the requirement—but his instant correction wasn’t enough to appease Mistress Jasmine. In a flash, she’d taken the washcloth back off of him, twisted it into a flogging tether, and swatted his unguarded penis with it. Robbie yelped, then gritted his teeth, swallowing any further outburst.

  “Good boy,” Jasmine then said, unfurling the washcloth and putting it back over his middle. “Now shut up.”

  He obeyed, squinting with discomfort when Heather patted it over his freshly tenderized unit again. “I want to play with it,” she said. It was almost a pout. “I want to make him make sperm with it.”

  “Let me go first?” Jasmine wheedled sweetly. The quickness of her mood swings was unnerving. “You know, since we’re besties?”

  Any trepidation or regret Heather may have felt seemed to have vanished. “Rock-Paper-Scissors?” she asked. And with a giggle, she added, “Five bucks on the line here.”

  “Deal.”

  They played the game right over his face, pumping their hands in time for a three count. On the first try, both Heather and Jasmine showed Scissors.

  “Bitch,” said Jasmine.

  “Whore,” said Heather, smiling sheepishly. “Go again.”

  Their hands pumped: One, Two, Three…

  Let it be Heather, God. Let it be—

  And they both showed a closed fist: Rock.

  “Goddamn it!” Jasmine yelled.

  Heather let fly an overly dramatic exhalation of exasperation. “Listen, you,” she then said to Robbie. “I think you’ve warmed up enough.”

  Robbie looked down on himself, only to discover his penis had gone half-stiff. It stood straight, the washcloth barely clinging to the tip like a surrender flag that had been shot multiple times. Heather plucked it away and tossed it over her back.

  “Oh!” Jasmine exclaimed. “Here’s our photo opportunity!” She fished out her phone and keyed in her code, swiftly passing it to Heather and repositioning herself between Robbie’s legs. Robbie could only see the back of her head, because she had turned around and gotten on her knees so that her friend could take a picture of her face, triumphant and smug, alongside his exposed private parts.

  Heather held the camera out, considering, tilting it this way and that.

  “What?” Jasmine demanded. “Do I have broccoli in my teeth, or somethin’?”

  “No, no,” Heather said, the corner of her mouth curling with uncharacteristic deviousness. “Dare you to kiss it—for the pic. For a laugh.”

  Yeah, Robbie thought, eyes rolling back as he felt her lips on the side of his shaft. That’s real funny. Oh, the hilarity.

  He went fully hard, helmet to belly again. Jasmine guided his cock back to standing with her pointer finger and resumed the kissing pose. Lips that trembled with a repressed burst of laughter against the taut flesh of Robbie’s genitals.

  The camera flashed, and the girls switched, this time Jasmine taking Heather’s phone. Heather, who perhaps remained yet a smidge more modest than her friend, was content to cup his balls in her right hand, resting her middle finger against the base, unable to keep herself from prodding him every second or two. “So springy,” she muttered in good humor, waiting for Jasmine to take the picture. “So weird.”

  Jasmine dawdled. “You know what?” she said, lowering the phone. “I think his thing is as big as it’s going to get. Let’s get your shot with this.”

  From one of her pockets, she withdrew a tape measure, exactly the same kind as his Matron had used the day before yesterday. She tossed it to Heather, who caught it one-handed and stretched it along Robbie’s unit. “Six and a half inches,” she said after the camera flashed. “You catch that in the pic? Is that … big, or average, or what?”

  “I got it,” Jasmine said, looking it over. “And I don’t know.”

  From the far circle, from Officer Thompson: “It’s above average—not ‘big’. Respectable.”

  Good to be respected for something, Robbie thought as the girls resumed their original positions on either side of him.

  They played a third round of Rock-Paper-Scissors. Jasmine was more predictable—choosing paper, as the one option neither had tried so far—but Heather went back to scissors, and thus won the game.

  “Oh … my … God!” Jasmine exclaimed, arms wide as though complaining to the Deity. She turned on a heel. “Fine. You have three minutes to make him come. After that it’s my turn.”

  “Don’t time me until I get going.”

  “Whatever.”

  Heather peeled off her right glove, dangling it over Robbie’s face before swatting his chest with it over the right nipple. Robbie gasped, more in surprise than actual pain, and made himself ready for the second blow over his left nipple when the second glove came off.

  “Remember,” she said, “you’re being punished. Tell me you understand.”

  “I … understand, Mistress Heather.”

  She reached down to her feet, eyes never leaving him as she
drew on what Robbie guessed must have been a second pair of gloves. He couldn’t be sure. He couldn’t see that far. Then she showed Robbie her hands, wriggling her fingers at him.

  They were hardly gloves at all. Her fingers were sheathed in latex with vibrating silicone spikes, but the palms were bare. There were wires, and a battery fixture just under the wrist. “Teaser gloves,” she said. “Hear them?”

  He did. They hummed like a bumblebee so happy and content it could just shit itself.

  “Yes, Mistress Heather.”

  She then extended her hand over Robbie’s middle, palm-up, without touching him. She spoke to her friend, but she was looking at Robbie when she said, “Little moisturizer, Jas? Since we’re besties.”

  Jasmine huffed. “’Kay,” she said at length, turning back to them and producing a fresh bottle of lubricant from her own supply. She popped the top, squeezed a generous dollop into Heather’s waiting palm. Then she withdrew.

  “Robbie?” Heather said, working the lube over both hands, through the gaps in her fingers. “I’m going to masturbate you now. There’s nothing you can do about it. I’m sorry.”

  “Yes, Mistress,” he said. And he thought, Who hasn’t?

  But this time was different. This time, it felt like a hundred fingers on him at once. It was alien, cyborg, both fleshy and mechanical, organic and electric—and, unlike Nurse Reyes-Garcia’s ministrations, amateur. Hard to predict.

  “Two and a half minutes to go,” Jasmine said, her back to them, watching the walls.

  “I want you to come for me, Robbie,” she said, working his shaft slowly with her right hand, the vibrating index finger of her left exploring him lower, prodding against the inside of his butt cheeks, gently rimming his sphincter. “Will you do that for me, Robbie? Please?”

  Robbie nodded, feeling the heat in his face and his middle and imagining himself beet-red under her touch. “Yes … Mistress,” he managed. “Just … just, please … d-don’t …”

  “Don’t what?” she sweetly asked, switching from index finger to thumb at the ring of his anus, scratching gently at his balls with her other four fingers. Her right hand kept pumping him, pumping him.

  “Two minutes,” Jasmine called.

  “Please don’t…” Robbie started, then lost half of his sentence when he felt her thumb starting to open him, “… my … asshole…”

  “Don’t do what to your asshole?” Heather asked, pressing farther in, up to the first knuckle. “Is this what you don’t want me to do? You don’t get to decide these things, Robbie. Sorry.”

  Robbie drew in breath, felt his stomach involuntarily clench. Her right hand kept working him. The tip of his cock dribbled. Cameras in the third circle went low on the poles, turned to catch the action south of his groin.

  Jasmine swung around, cut in with, “You’re diddling his—”

  And Robbie ejaculated hard, the first jet of seed clearing his chest and spattering his own cheeks.

  Heather stepped back with a squeak, drowning out the pop of Robbie’s hole as her thumb dislodged from him.

  Untended now, all on its own, Robbie’s cock shot a second jet, then—rather drunken and dejectedly—drooled out half of a third before settling back, half-stiff, in the mess it had made on his belly.

  “Woohoo!” Heather cheered, hopping up and down in place as she stripped off the vibrator gloves. “Five bucks for Team Me!” Then, looking at her hands, “Um, little help here?”

  ****

  Nurse Reyes-Garcia supplied the towel, since Heather had abandoned Robbie’s washcloth to the floor. She said nothing. Everything was going, more or less, according to script. Robbie’s vitals were elevated, but not alarmingly so. He was normal. He was dealing.

  He was about to weather a significant shock, though.

  Floor fixtures in the second circle accessed the prison water supply. These hummed to life as the suspension beam again straightened, standing Robbie up, still dribbling spunk from his face, chest, belly, and penis. Officers Kersey and Thompson then came forward with a pair of hoses that might have been commandeered from the set of an old 1970s women-in-prison flick and sprayed him down.

  “Lean him forward, please,” said Jasmine. “Still straight, but face-down. Ass in the air.”

  The stone support strut retreated. The suspension beam leaned back, then forward, then kept going forward, until Robbie was suspended in the same position but in the opposite direction as before, facing the floor. The backrest then re-fixed itself, supporting him at the belly this time. A second, smaller support met him at the chin, holding his head in place, making it impossible to hide his face. Officer Kersey rolled up an extra camera and left it in front of him, to catch his reactions for any of the viewers who decided to go split-screen.

  This is where I may have to jump in, Nurse Reyes-Garcia thought. And I will, if Robbie starts spiking or if she goes too far. I do not like the looks of this one, this “Jasmine Forshay”.

  Jasmine stepped forward, boots clicking, until her hips met the back of Robbie’s balls and the top of her shorts rubbed against the cheeks of his upturned buttocks. She reached forward, massaged his shoulders. Tickled him at the armpits, making him wriggle and whimper. She leaned in toward the back of his head.

  “How you doing, criminal?” she asked. “Feeling anything funny down there?”

  Robbie moaned.

  You will be fine, Nurse Reyes-Garcia thought. Roll with it, Robbie. Do not be afraid. I will protect you, if it comes to it.

  She wished she could tell him.

  ****

  He was erect again.

  What? he thought. How?

  He’d come all over himself less than five minutes ago, and yet his cock was as hard as it had ever been. Hell, even if he hadn’t just blown like the top of Mount Vesuvius at a toga party, he could not imagine why he’d gone stiff for Jasmine—who frankly scared the ever-loving fuck out of him, and was now standing between his legs ready to inflict God-only-knew-what unspeakable act upon his person.

  “I have something for you,” she said, reaching under him, milking his penis with a pre-lubed hand still ensconced in leather. “I want you to guess what it is.”

  Whatever it was, she laid it across the crease of his buttocks. Still stroking him down under.

  Robbie’s heart thudded—partly from the continuing strain at his wrists, shoulders, and ankles; partly from the unaccountable excitement coursing through his loins; partly from fear.

  It was long and thick. It was plastic. It had some kind of elastic cord at the end for a handle.

  Jasmine rubbed her hips forward, dry-humping him without a cock.

  It’s a dildo, Robbie thought, dread escaping his lips in a wordless, drawn-out moan. She’s going to fuck me in the ass with it. This can’t be right. This is going too far.

  It was bigger, wider than the flogger handle had been. He wouldn’t be able to take it. She’d rip him wide open with it.

  “I gave you an order, bitch,” Jasmine said, stopping to squeeze his cock hard without stroking it, making him cry out, forcing fresh tears. “When the bitch gets an order from his mistress, the bitch does as the bitch has been told.”

  Robbie wouldn’t have been so taken off his guard, had this treatment come at the hands of Officer Thompson, or even his Matron. They knew things, those two. They were professionally trained. Years of experience had made them experts in the ways of man-reduction, of turning transitionals like himself into slobbering “bitches”. But, strange and unpredictable as she was, how did Jasmine know these things? How did Heather, of all people—who Robbie had casually surmised to have been the timid one, even compared to Maddy?

  It didn’t matter. He had to answer—and he had to do it right now.

  “It’s … it’s a d-dildo…” Robbie managed, choking on his sobs. “You’re going to … fuck me.”

  Propped up as he was, he couldn’t avoid the video screens. There, people who could see the object nestled over his butt cheeks were laugh
ing at him, having a grand old time at the thought of Jasmine going hilt-deep in him, of looking him in the eyes while she did it.

  Jasmine slapped the back of his head. “I didn’t ask what you thought I would do with it, cocksucker,” she snarled. “I only asked what you thought it was.”

  “I’m sorry, Mistress Jasmine!” he blurted. And couldn’t help himself from continuing. Even though he knew he was being disobedient, even though he’d already had Heather’s thumb up his ass, and his jailor’s finger, and the rawhide handle of a flogger—with a vibrating stud, to boot—he was unable to restrain himself from pleading with her, “Please, please don’t … fuck me, Mistress Jasmine!”

  And allowed himself to dissolve into pure hysteria.

  Flashes. The cameras were taking stills.

  Jasmine let go of his cock, took both of his ears in leather-clad fists, and said, “Robbie, relax. It’s not a dildo, okay?” She gave the back of his neck a quick, conciliatory squeeze. “Jesus Christ, Robbie. Man up. Starting to make me feel guilty, here.”

  ****

  His whole body went limp at that. Well, Jasmine thought, scooping his cock and balls up in her hand again, almost all of it.

  The thing riding the crack of Robbie’s ass was actually a cattle prod, of sorts. It was long enough for a dildo—the ruse had been Officer Jenny’s idea, to be fair—and it was set to a safely low voltage, provided she only used it once every thirty seconds or so. But it would get his attention. It sure had gotten hers.

  Officer Jenny had made her feel it, just once, before allowing her to select it. She’d zapped Jasmine on the thigh with it, on the bare skin just under her butt. The jolt had made her cry out and swear, and then—well, then, the whole idea was just that much more hilarious.

  “Who’s my bitch, Robbie? Tell Mistress Jas who her bitch is.”

  “I-I am,” Robbie gasped, sweat gathering along the length of the prod nestled in his crack. “I am … I’m your bitch, Mistress Jasmine.”