by Trent Evans
“Many times,” Ivy murmured.
The grin was clear in the tone of Anna’s voice. “Yes, I suspect you probably have. But that’s to your advantage then. There’s a reason they say subs make the best Dommes.”
A shudder coursed down my spine at the words. Could I really do this? I was being rendered into something little more than a guinea pig, a test subject, a prop to teach another woman how to hurt, humiliate, and subjugate a man.
But it’s what your Mistress wants.
I actually shook my head at the thought, cursing silently. Was this really who I was becoming? Though it angered me — that I could see my free will draining away, like water through a sieve — I was ever more comfortable — or at least resigned to — this new reality. The inescapable fact was that pleasing Anna was the only way I could possibly make my lot in life better. Even if only a little.
I just wished it wasn’t so easy to surrender to that truth.
“One of the things you’ll probably have to do with the virgins is walk them through things, coax them into cooperating. Some of them have never even considered the possibility of anything entering their asses. I mean never. This is going to be a shock to many of them — and you’ve got to be prepared for the ones that fight it.”
Ivy was silent for a second. “You mean… force them?”
“Most of these slaves want to be forced, dear. They want to be forced to confront these things that are a threat to their perceived control, their masculine construct, their self-image. They’re afraid that what makes their cocks so hard, makes them less than a man. They’re dead wrong on that — but you don’t need to tell them that. You need to use that to your advantage — it’s power. They want to give it up, they want a woman to have all of it — and they want her to use it on them in the ways that most pleases that woman. But inside, many of these men, they’re too scared to explore it, to ask for it, on their own. Which is where you come in.”
“That sounds a little too close to rape, to me.”
“And you’d be wrong about that. With very few exceptions”—Anna patted my hip and I gritted my teeth together until they screamed in pain—“they’re going to be coming to you — and expecting you to take that choice away from them. It’s what they signed up for. I know that seems wrong, or abusive, or contradictory, but trust me, once you understand them, they are really quite simple creatures. They need a very firm hand, painful consequences, and a woman strong enough to conquer them — in every way. Do that, and they’ll do anything for you. There’s nothing else like it in this world, Ivy. Though perhaps you already know the way of it… from the other side, that is.”
“I… I can relate, yes. My Master — he likes to tell me how much he enjoys what I do, how much he enjoys my submission to him. How much it turns him on. It makes me happy to know he’s happy… I can’t even explain how happy it makes me.”
“You don’t need to, dear.” The words were as gentle as a caress. “It’s a very precious thing. I know, Ivy. Believe me, I know.”
I shifted in my bonds as much as the brutal straps cinched down at the small of my back and across my shoulder blades allowed. A harsh smack landed across the lower part of my ass, the pain exploding across my flesh, reawakening the soreness of those welts there.
“You be still, or I’ll be instructing Ivy on how to use that cane after all,” Anna growled.
I froze, the mere thought of that cane biting into the still aching wheals making my stomach do flip-flops.
Ivy’s gentle laughter made my face flame anew. How the hell had I gotten myself into this?
“Here, this is a good one to start with,” Anna said. “When you’re penetrating them, you need to work them up to it. I know it’s fun to think about just jamming a huge cock up their little asses, but this isn’t some twisted fantasy book — this is real life. If you do that to someone not prepared for it, you can tear them. Not fun for anybody, trust me on that.”
“Of course,” Ivy said. “I don’t want to hurt him.”
“Not at first, anyway,” Anna purred.
Oh shit.
“I think a finger works fine to ease them into it. Some people like to use things like thermometers or narrow prods — anything thin that the anus can easily deal with. Up to you, of course.”
“I’d rather use a finger,” Ivy said, her voice quavering ever so slightly.
“I knew I liked you, Ivy.” I heard a box being torn open, then the sound of latex being pulled. “Glove? Either way is fine, but sometimes a glove can make it that much more embarrassing for them if they’re struggling with it.”
“No, thanks.”
“I’m with you,” Anna said. “I think the finger shoved up their ass is plenty embarrassing in its own right.”
The lubricant was shockingly cold as it was spread upon my hole, and I couldn’t help but clench in response. It earned me another bun-burning smack of Anna’s hand.
“Keep it opened, boy. You know better than that.”
Then Ivy’s finger — her nail blessedly cut short — was presented to my anus and I breathed out, knowing it would hurt a whole lot less if I just relaxed for it.
“Let her in, Quinton,” Anna said, the warning plain in her tone. “This is nothing. Let it in.”
Then the finger slipped inside, and I could hear Ivy’s sharp intake of breath, even as she plunged deeper. It wasn’t uncomfortable, but the knowledge that it was someone’s finger other than Anna’s… I wasn’t sure how to feel about it.
It was a sort of violation, in a way, but mostly, I felt it was… right.
Anna wanted it, so it happened. That was it. There was a time I’d have felt the injustice of it. But now? I simply wanted to make her pleased with me.
And I really, really didn’t want my ass beat again. I was ready to take a baseball bat up my back door if it would save me from another round with that goddamned cane.
“He’s so hot in here,” Ivy whispered, her finger wiggling a bit inside me.
“Ease it back and forth inside until he’s not resisting at all.”
I gasped as she pulled it back, the sensation exploding as she pulled it almost all the way out. I didn’t understand why it felt — I swallowed hard as I admitted this to myself — so good coming out. It wasn’t that it was awful as she thrust back inside, but there was something about the withdrawal, some different sort of… stimulation that was happening.
Wonderful. You’re now aroused by things being shoved in your ass. Yeah, real tough guy you are.
Ivy thrusting increasingly fast, my breath was beginning to labor when her finger was pulled free.
“Now, I like to go up to two fingers next,” Anna said gleefully. “That really hits their prostate when the knuckles drag over it — but let’s go with this plug first. It’s about the same width, but it’s probably better to start with this.” A hand gave my buttock a harsh squeeze, the nails digging into my skin. “Plugs embarrass him more too.”
I shivered as the cold glass was pressed to my cringing opening. Thankfully, it pushed inside easily, a sigh drawn from my lips as it seated fully. It was a little uncomfortable, but I could tolerate it if I had to.
“Give him a minute, then you need to start moving it in and out. Slowly, at first, but as he stretches a little more, you can go harder.”
Too soon, the glass began to move within me, making me bite my lip each time the widest part was pulled free of my sphincter. Just as with the finger, it was far, far more intense as it was withdrawn, and as Ivy moved it faster and faster, I couldn’t help the moan at the confusing, intense sensation elicited by the plug as it stimulated, over and over, my increasingly sensitive tissues.
A palm patted my ass. “You like that, don’t you, boy? I know you want more. You’ve got a lot more coming, so you’d better be careful what you wish for.”
My hips were beginning to move of their own volition when the plug was removed entirely. I hated the feeling of emptiness left behind, even as I welcomed the rel
ease of tension at not being probed — if only for a few moments. It confused me hopelessly.
“He’s… it’s gaping open a little,” Ivy said, wonder in her voice.
Anna laughed softly. “That’s nothing. Wait until you see what happens with the bigger ones. Try this.”
More sticky, cold lubricant was applied to my crack, a finger poking more inside my opening. I tensed uncontrollably though as the broad phallus touched my throbbing anus.
“T-that… that’s too big.” I swallowed hard, my heart pounding. “Mistress.”
“I’ll decide what’s too big, boy. And let me assure you, this is no bigger than the plug I made you take when you were still down there in your hole. Perhaps you’ve forgotten it?”
Or blocked it out.
“Now, as you go larger, you’re going to want to go slower, Ivy. Try to get the tip in.”
“Like this?”
I grunted as the plug pushed forward and I canted my hips, trying to open more for it, even as it made my blush explode hot on my cheeks. It was humiliating in a way nothing else was, the helplessness, the degradation of something forcing itself into the most private place in my body. The feeling of a total loss of control was elemental, and shocking.
Still, I beared down, trying to obey, trying to please Anna.
A groan was drawn from my lips as I closed my eyes, the stretching real this time, discomfort just on the edge of becoming real pain.
“As you get to the widest part, ease it back a little,” Anna murmured. “Yes, just like that. Push and pull back, and again.”
The profound relief as she pulled back a little made my whole body shudder, the tension growing within me making every muscle in my body tight. A bead of sweat coursed down my forehead, itching as it trickled down. I took a great breath of air, the smell of the leather padding all around me.
“That’s right. Push.” The hand on my cheek squeezed brutally hard. “Open it. Open it, boy. As far as you can go. Widest part now.”
“Hurts!” I blurted, even though it wasn’t true pain, more supreme discomfort, the humiliation, and tension, and total loss of control threatening to overwhelm me. It seemed too big, my ass feeling like a tree was being forced inside.
“Does it really hurt?” Anna asked. “Or is it just stretching a little?”
I wanted to lie, knowing it would spare me. I didn’t dare.
“Stretching — a lot.”
“I thought so. Back it off a bit. Then he’s going to swallow this plug all the way down.”
Oh, God!
A finger touched my sorely stretched anus. “Look at that,” Ivy breathed. “It’s really opening now.”
“Just takes patience. You won’t believe what these men are capable of enduring, if you go slow enough with them.” Nails dug into my buttock. “Even these scared little virgins.”
I took a deep breath, my anus still pulsing around the remorseless phallus.
“One more push now. He can do this. Just steady pressure.”
I grunted as it pressed forward once more.
“It’s okay,” Ivy said softly. “It’s okay. Just a little more.”
“Ahh!” The stretching was on the knife edge of pain, but still I pushed, not quite believing how much it was spreading me open.
“You’ve got it — one last push,” Anna said.
“Fuck!” I barked, trying to push, visualizing myself opening. Then it slipped through, and I groaned loudly, my body shuddering, my ass clenching tight around the narrow neck of the plug. The bulk, the remorseless, shocking fullness had me breathing fast and shallow. It was only barely tolerable, the plug stirring deeply confusing — and embarrassing — sensation within me.
“How’s it feel, boy?” A hand stroked the stinging skin of my ass, nails tapping against one of my more painful wheals. “Little full?”
“Yes… Jesus Christ!” I said, desperation clear in my words. “I…I don’t know how to describe it.”
Anna’s heels clacked on the floor as she moved up to my end of the bench, crouching down to whisper at my ear. “And that’s only a medium-sized one, boy. Wait until you have to deal with mine.”
Mine?
Then I remembered it, the mention she’d made of something she’d had made special just for me, early in my captivity down in that wretched prison below the house. I hadn’t a clue what she was referring to then, my mind occupied with the overwhelming change in my situation, my newfound imprisonment.
I had a clue now though.
Oh no.
I knew quite well what happened between male submissives and their Dommes. And I knew there was more that I hadn’t yet been introduced to. I didn’t know whether to be terrified, frustrated, or look forward to it.
The one thing I did know was that I feared more pain. It didn’t seem to quench my arousal yet — something I still didn’t understand — but I did fear it. I was terrified of losing total control, of growing desperate.
Of begging. Or worse.
Stay in the moment. You just need to survive, to adapt. She is your path, she is your hope. Please her, and it will be okay.
Though a part of me resented, maybe even hated, those words, I knew they were truth. They were my reality, my new world. I had no choice but to embrace them, to allow myself to flow with the experiences, the sensations, to mold myself into the slave she wanted. I would overcome, persevere. I would endure.
I could do this. I just had to start believing it.
“Quinton? You there?” Anna’s whispered words brought me back to the present. “Did you hear me?”
“N-no, Mistress.” I could barely form the words.
“It might not be easy to take your plug back out. Do you want Ivy to take it out though? Are you starting to hurt?”
“Yes…Yes.” My asshole throbbed now, the stretching inside now quite uncomfortable.
Her breath was hot against my temple as she whispered the words so that only I could hear them. “I wish you could feel how wet your Mistress’ pussy is, Quinton. How much your pain turns me on. Would you like to feel it?”
I didn’t know how I was supposed to answer, so I went on instinct. “Yes.”
“I know you do — but you can’t. Do you know why?”
This answer I knew well, bitter as it was. “Because I haven’t… earned it.”
“No, you haven’t. But it pleases me that you see the truth. That’s the first step.” She sighed softly, nuzzling my hair with the tip of her nose. “If you want that big plug out of your bottom, you’re going to have to do something.”
“Okay, I’ll do… it.” My anus was angrily pulsing now, in perfect time with the pounding of my heart. I was prepared to do a great many things to be relieved of it.
“I want you to ask for it.”
“W-what?”
“Ask nicely, my stubborn boy.”
“Please, Mistr—”
“Not me.” Anna’s lips pressed a soft kiss to my ear. “Her.”
My heart sank, the humiliation flooding through me. At that moment, I felt my lowest, having to ask another woman, the sweet, innocent Ivy, to take the large glass plus out of my ass.
“I can’t do it,” I whispered, squeezing my eyes shut so hard they hurt.
“Oh yes, you can. Things are only going to get harder from here, Quinton. If you can’t do this, you’re going to have a very difficult time coping with what’s coming.”
“Please, Mistress.” I rasped it, vainly hoping she’d spare me this shame, this degradation.
“That ass is mine, boy. Your body is mine. Your only job — do you remember it? I want to hear it.”
Please God, don’t make me do this.
“Obey you.”
“That’s right. Now, your Mistress just gave you an order.” Anna caught my earlobe between her teeth, nipping it hard, bright pain making me wince. “And I expect you to be a good boy and obey it. You know what will happen if you don’t.”
The lump in my throat was painful as the
words tumbled from my lips.
“Ivy, please take out the plug.”
“My plug,” Anna said, almost snarking it.
“Ivy… please take out… my plug.”
Lust and sweetness warred in the tone of Ivy’s soft reply.
“With pleasure, Quinton.”
Chapter 22
Anna watched him closely as he sat at the kitchen table once more, hunched over, his eyes never even leaving the floor. Something had changed in him when they’d unstrapped him from that bench.
She’d seen it before, but she hadn’t expected to see it in him.
Yielding.
He’d given up his silly resistance. Inside, she suspected there was still a holdout, a last redoubt of defiance and anger — even selfishness.
But the battle was over. She knew it then as she’d led him from the room, her hand firmly wrapped around his still hard cock. Knew as he’d wordlessly followed her order to sit down on the hard chair, a perch she knew from his wince was anything but comfortable.
Ivy, wide-eyed, and very aroused, had followed them out, her plump lips crimson, nipples standing out stark beneath the shirt she wore. Now, the red-haired sweetheart stood behind him, a curvy hip leaning against the back of his chair.
“I want to hear you say it.” Anna said, staring him down even though he refused to look at her. “She’s been a big help today. Be polite.”
That adorable blush flushed upon his cheeks. “Thank you, Ivy.”
“You’re welcome, Quinton.” Ivy’s big, tear-bright eyes met Anna’s over his head. “I had fun today. You were a… good boy.”
Quinton’s head sagged down still further, his shame seeming to weigh him down.
Anna relished it, her sex a burning cauldron of lust as she looked upon him.
“Time for me to go, Quinton,” Ivy said, peering down at him. She bent close, glancing at Anna.