by Trent Evans
“Not for long,” Anna said in a sing-song tone, Quinton shuddering in his bonds. She pet his trembling leg, pinching him gently just behind the knee. “Don’t be afraid, boy. Mistress will take good care of you. All you have to do is obey. That’s not so hard, is it?”
He looked away, clamping hard on his bit.
“Embarrassed. They all are when they surrender their little holes.” Anna smiled at her friend. “Very normal — and it’s not going to spare him a bit. Embarrassed or not, he’s got to learn that tight ass of his is no longer his. It’s the property of his Mistress now.”
“Poor boy,” Darynn mocked, wiping down the glass phallus with the antiseptic before wrapping it in a white towel and setting it back on the cart.
The click-clack sound of heels could be heard down the hall.
“Oh, good timing,” Darynn said, winking at Anna.
A delicate hand knocked on the doorjamb, the curvy, alluring figure of Ivy filling the doorway. She wore a body-hugging sleeveless white top that had her generous breasts practically spilling out of the daringly low bodice. Her faded blue jeans were pleasingly stressed at her wide hips. The fabric was fashionably torn at the front of one thigh, a patch of alabaster flesh could be glimpsed through the ragged hole in the denim.
“Am I late?” Ivy’s eyes glittered, her plump lips painted a pale, glossy pink, her cheeks nicely rouged to complement the striking auburn of her long hair.
“You’re just in time,” Darynn said, rolling back to allow the girl to see the hanging, helpless Quinton, his hard cock standing up between his widespread thighs.
“Oh, my God,” Ivy said, walking toward them, her lower lip caught between her adorable white teeth. “I should have driven faster.”
Chapter 21
“Now, Quinton, you just stay very still for Ivy. For the next few minutes anyway, she’s your Mistress now.” Anna stood at his head, purposely close, knowing he couldn’t help but smell her strong scent of her sex, the gusset of her panties soaked with the proof of her deep arousal.
His eyes stared up at her, the terror there plain, but as before, his cock was still full, pulsing, eagerly standing up even as Ivy took Darynn’s seat on the stool, her avid gaze locked upon his helpless, engorged genitals.
“I love it shaved like this,” the red haired beauty breathed. She looked up at Anna. “Can I?”
“You can do anything you want to him — just don’t let him come.”
The lost sound escaping from behind Quinton’s gag made Anna’s womb clench, a quiet moan of her own just barely swallowed down.
Ivy wasted no time, the novice domme-in-training taking hold of his veined, pulsing cock with one hand, grabbing the bottle of baby oil from the cart. She left his penis to loll and throb between his spread thighs as she coated her palms in a thick layer of glistening oil, drizzling more of it on the broad, swollen meatus, the clear fluid coursing down the thick shaft.
“Oh, he’s in trouble now,” Darynn said, gleefully, her hand wrapping around Quinton’s elevated shin. “He was practically begging after Ivy’s last visit when he was still down there in his hole.”
Anna didn’t reply, unable to even form coherent speech as she watched Ivy’s hands take hold of his cock, fisting it slowly, working the oil into him until every inch of his sex glistened.
“See those marks on his ass and thighs?” Darynn pinched one of the swollen welts to an angry — but muffled — protest from Quinton. “We’ve been beating him within an inch of his life and that nasty cock of his just gets harder and harder. Been a long time since I’ve seen one of them react to pain like that.”
They all watched in silence then as Ivy’s hands worked their magic, stroking slowly, working him unhurriedly, the veins of his cock increasingly constricted, inflamed. Ivy’s big eyes watched him intently as her hands moved up and down the gleaming shaft, pausing now and then to fondle and gently squeeze the scrotum, Quinton groaning softly each time, though she wasn’t sure if it was with pain or need.
She hoped it was both.
Anna couldn’t help adding to his torment, dropping to one knee to whisper in his ear as the girl’s delicate hands pumped his cock ever harder.
“You want to come so badly, don’t you, Quinton? Your seed is dying to be released. You’d like to spray it all over her hands, wouldn’t you? Maybe have her lick it off? Those soft lips kiss your cock for you?”
He jerked in his chains again. “MMMMmmmhhh!”
“No, Quinton, you’re not going to be coming anytime soon, so you’d better get used to this.”
Darynn watched Ivy tormenting him, a wry grin curving her lips. “Show him your tits, Ivy.”
Ivy blushed a little at the suggestion, but at Anna’s slow nod, she let go of Quinton’s penis, to let it pulse and twitch against his belly. The broad head was an angry purple-red, the slit at the tip gleaming with his wetness, a string of it dripping down to mix with the black hair on his belly.
Rather than take off her top entirely, Ivy simply tugged the bodice down, her buoyant, round breasts popping out, the neckline supporting and lifting them. Her pink nipples were very hard, prominent.
Anna watched Quinton slowly, his eyes unerringly following every sway and wobble of those soft breasts.
“You like them, don’t you, hmm?” Anna whispered it to him, her lips teasing the curve of his ear. “Should I tell her to wrap those around your cock? Maybe we could have you suck on those nipples.”
He threw his head back, groaning desperately.
It was a delicious torture. She knew he wanted to come so desperately already.
“You know you’re not permitted to, don’t you? You know your Mistress will be very disappointed in you if you come, isn’t that right? But you’re a good boy; you won’t let yourself spill your seed.” She pinched one of his nipples between her fingernails. “You don’t want your Mistress to have to discipline you again.”
Ivy squeezed him hard, and his hips jerked, her fingers tight just under the swollen purple head of his cock, as if she meant to strangle it. Then she eased her fist down once more to the base, the veins almost pulsing along the length of him.
“MMmmm!! MMmmmm!”
Licking her lips, she gave Anna a tentative smile. “Should I let him?”
“No!” Anna almost snarled it. “Keep going though. Our little Quinton is going to learn control, whether he wants to or not.”
“Sit up closer,” Darynn said. “Let him see your tits. I can tell he loves them.”
“Do you like Ivy’s big breasts, Quinton?” Anna pinched his nipple harder, and he shuddered, grunting. Still, his eyes were wide, desperate, watching the lovely, auburn haired beauty masturbate him, adding more oil to her hands as she stroked him faster and faster. “You want to come on them, don’t you? Spray your come all over those big tits, yes? Oh, it would be so good, such a relief.”
His chest heaved frantically, sweat pouring from his body, his head waving side to side, his eyes rolling back, his voice ragged as he keened almost continuously.
The power of her possessiveness flared within her then. “But you’re not going to come, not one bit. You’re going to keep it inside you, your balls aching, desperate. You’re going to be hurting later on, so sore, wanting so much to come. But you will not, Quinton, you will not — until your Mistress grants you relief. Do you understand?” She twisted his nipple and his head dropped, his eyes wide once again as he yelled into his gag.
Ivy’s hands pumped vigorously now, her fingers continuously fondling his scrotum, his balls now tight against his body.
“Lick him, Ivy,” Darynn said, meeting Anna’s gaze. “Lick that cock. Make him suffer.”
Her pink tongue extended, the tip licking up a long line of Quinton’s precome from the tip of his penis, a string of it laying itself along her chin.
Anna didn’t know why it happened, but the sight of Ivy licking him opened up something deep inside her, a selfish, possessive, jealous lust that took her complete
ly by surprise. She jumped to her feet, waving her hand at Ivy.
“No! That’s enough, Ivy. You can let him go, for now.”
The pale beauty’s eyebrows rose, even as she licked her lips. “I — okay. You all right, Anna?”
“It’s… I’m okay.” She glanced at her trembling, exhausted slave. “Just — it’s enough for now.”
Darynn frowned. “Anna—”
“We need to be alone.” She shot a pointed look at her friend. “You two take a break, okay? I’ll be out in a few.”
“Come on, Ivy,” Darynn said, shaking her head as she walked for the door, her hand on Ivy’s shoulder as the woman tucked her naked breasts back into her top.
Quinton’s eyes narrowed as he watched the two women go.
Taking her seat on the stool, the leather still warm from Ivy’s lush bottom, Anna wrapped a hand around Quinton’s penis.
“Did you want to come from looking at Ivy’s big tits?”
His brow furrowed again, but he didn’t attempt to answer.
“Yes or no, Quinton.” She scratched at the opening to his urethra with her thumbnail, and he bucked.
He shook his head, and for a moment she looked upon him, considering. The next steps could take things in any number of directions, but after what had just happened, she was starting to suspect there was only one true way this could really go. A lot would depend on him, of course.
And on you, idiot.
“Things are going to change, and I want you to know what’s going to happen so that you know what to expect. But first, questions.” She stood, strolling slowly around him. “If I take out your gag, do you promise to follow directions?”
He nodded frantically.
In seconds, she loosened the bit, pulling it away to his gasp of relief. Fortunately for him, he stayed quiet.
Dropping the bit on the cart, she sat before him again, his eyes following every move.
“I want answers, and I want them now.” She took a deep breath, staring at him. “Why didn’t you come if you liked her tits so much?”
His nostrils flared, his tongue testing one of the marks at the corners of his mouth. “Because… you told me not to.”
Triumph filled her at the sweet words. There was hope! Could she dare entertain the idea this man was even… redeemable? It seemed absurd even forty-eight hours ago, but now?
Nothing seemed impossible anymore.
Except convincing a certain Trust founder to go along with it, even a little.
“Are you hurting right now?” She gripped his penis again, giving it a proprietary squeeze that had him grimacing. “Balls aching?”
“Yes, Mistress.”
She liked that the word seemed to be more comfortable for him now. It was yet another good sign.
“Do you think you deserve to come?”
He struggled with the question, his cheeks flushing. She stroked him once, and his body tensed.
“I know you… won’t let me.”
“And why is that?”
“Because it’s what you want.”
She smiled at him. “No, that’s wrong. It’s because it pleases me. It pleases me to see you needy, and desperate, and sore.” She pumped his cock in her fist slowly as she continued, Quinton’s eyes rolling back as his head dropped back. “It pleases me to know that you want so very badly to come — and that we both know you won’t unless I permit it.”
His thighs were trembling again as she continued to masturbate him. “Please…”
“Please, what?”
“Please… stop.”
“You don’t want me to stroke this cock?” She stilled her hand, tapping the sticky head with a fingertip. “I’d have thought you’d be begging for anyone to play with this desperate thing. Maybe one of us would fuck up? Go a little too far, and you spill your seed on accident?”
“Jesus,” he hissed. “Please stop, Mistress.”
She continued, her hand coursing up and down his no doubt sore and inflamed shaft. “If I didn’t know any better, I’d say that sounded like a slave who still didn’t understand his situation. You don’t ever tell me not to do something. Do you understand?”
“Yes, Mistress.” His voice sounded like he was nearing the breaking point, the sound desperate, the tone near to cracking. “It… hurts.”
“I know it does.” Anna said, cooing at him. She took her hand away, tapping her chin with a finger. “I wonder — would you like to play a game?”
“Y-yes, Mistress.” His teeth worried the inside of his cheek, his hips subtly writhing.
“It’s a game of choice.” She beamed at him, affecting her sweetest smile. “Just like I tell you. There is always a choice here.”
She rose to her feet, resting a hand on each of his thighs, using the grip to lean closer, her upper body angling between his spread thighs, the position making the swell of her breasts jut over him as she stared into his now sweetly anxious eyes.
“A choice.” She jerked her head back toward the door. “Your sweet, big-breasted Ivy is here to learn a thing or two about the dirty, dangerous male animal, and what makes him tick when it comes to bending one to your will. She has many lessons to learn — some I’d hoped you’d… help her with.”
His throat worked as he swallowed. “Yes, Mistress.”
“So, you can choose one of the following.” She looked upon him in silence, loving the way the tension ratcheted up by the second.
“Please, Mistress.”
“Such an impatient boy,” she admonished, giving him a sly smile when he paled. “But it’s cute now and then.” His body visibly relaxed in its bonds. “Now the game is, each choice is both good… and bad. But each in a different way. You must choose — or your Mistress will choose for you. Ready?”
“Yes, Mistress.”
“Choice number one: Ivy comes back in here and we get to watch her jack off that disobedient cock until you go off like a fountain. Doesn’t that sound so good? All that pent up tension, and pain, and frustration? Finally?” She tilted her head, delighting in the glimmer of hope she spotted in his eyes. “But with the good… comes the bad. If you choose this, Ivy will also be instructed on the use of the cane — on you. I daresay, with the current state of your poor bruised and welted ass, it won’t be pretty when she gets done with you. She’s never caned a man before, but I think with a little coaching from Darynn and me, she’ll take to it like a duck to water. I wouldn’t want to be in your shoes — if that is, you were wearing any.”
The color had drained from his features as she’d gleefully dropped the figurative boom on him. His expressive face might have been one of his most appealing features, affording a woman like her such a wonderful window inside his thoughts, offering insight into his emotions he couldn’t hide if he tried.
“The other choice — number two: we show Ivy around the male ass — specifically the asshole. And you get to be the test subject. I suspect penetration will be involved, likely uncomfortable penetration at that. Now, I’m guessing you’d consider that the bad part.”
He was breathing hard again, his lips a thin line as he glared at her. She drank in the injustice of it, the unfairness of everything about this arrangement. One of the hardest things for male slaves to adjust to, no matter their previous experience, no matter their general level of innate submissiveness or willingness to serve, was the pervasive unfairness of being a slave, of true submission. There was nothing but obedience… and fairness was never even a consideration. The sweet agony of the submissive’s lot.
“The good part, well, that likely is going to depend upon you. As we give Ivy a tour of your back door, you’re likely — especially considering your condition — to grow rather… stimulated. You might, if you’re very lucky, get to come — though I highly doubt it will come about from touching your penis. That, I’m afraid might feel quite lonely should you choose option number two.” She palmed his testicles, luxuriating in the way they rolled about in the smooth scrotum, so delicate, so swollen, s
o vulnerable. “Which will it be, boy? I’m waiting.”
Eyes flashing, he stared at her for a moment, his jaw clenched tight. Then he looked away with a tiny sound of anxious displeasure. His body had already begun to tremble as his gaze slid up to the ceiling, his long breath one of pure resignation, frustration, and hopelessness.
“Option… two. Mistress.”
* * *
“Now, the first thing you need to remember with these males is that what they say, and what their body does, are often two different things.”
Anna smacked my displayed ass, the sound echoing off the walls. “This one here — he’ll tell you he can’t, that it hurts, that he’s had enough. Sometimes, he may be right — but pay attention to his body’s reactions. Often a male will say those words and yet, his cock is standing up tall and proud. His body is telling you the truth.”
I knew they could still see my erection, even laid over the bench as I was. They’d made me push my hips back enough to give my penis room to stay hard — and probably to allow them free access to it. My legs had been spread so wide when they strapped my ankles to the lower legs of the bench, that my balls and asshole felt like they had a spotlight right on them. I couldn’t have been displayed in a more vulnerable, helpless position. I knew what was coming, I thought, but it didn’t make it any easier.
In a way, it made it even harder. That dread making each second seem to drag on longer and longer.
“Go ahead and spread his cheeks apart.”
“You really marked him,” Ivy said in a soft voice — one filled with more awe than sympathy.
“He deserved it. I like the look of it on him. He doesn’t have one of those flat asses. His is nice and round — more for us to punish.”
I pressed my face to the cushions of the bench beneath me, my cheek hot against the cold leather. I felt my buttocks pulled apart and I willed myself to cooperate, not wanting to earn more welts and wheals to go along with those still decorating my very sore ass.
“Good — now, see how he’s nice and smooth? If that’s what you want in a slave, it’s your prerogative to do with him what pleases you. If you like hair, fine. If you don’t, it’s logical and expected that you’d have him shorn. Again, it’s up to you.” Anna shifted behind me. “Let’s start with the small one, so you get the feel for it. Have you ever had one of these used on you?”