Chapter 14
Laura
I moved to the end of the bed on autopilot, my body following his instructions even as my mind screamed in protest. I bent forward, pressing my palms flat against the mattress, and spread my knees apart the way he’d commanded.
The position made me acutely aware of my bottom cheeks—still burning from the spanking, the welts from the orderly’s cane overlaid with Mike’s handprints.
It also made me conscious of how the posture Mike had commanded left those punished cheeks spread. I could feel the air there, moving over the tight little button of my bottom hole.
A wave of dizziness washed through me, making the room tilt.
I gripped the mattress harder, my fingers digging into the comforter as I tried to steady myself.
The position forced my back to arch naturally, my bottom rising higher, and I felt suddenly, acutely aware of how exposed I was.
How naughty the pose looked. How deliberate it seemed, like I was offering myself for exactly what Mike intended to do to me.
The realization sent new heat flooding through my body, centered behind the terrible, tight line that closed the furrow of my labia.
I reached for the tube of lubricant with a trembling hand, fumbling with the cap. It took three tries to get it open, my fingers slippery with nervous sweat. When I finally managed it, I squeezed a generous amount onto my right hand, watching the clear gel pool in my palm.
This was it. This was really happening. I was about to touch myself there, prepare myself there, for ‘training’ by a man I’d met this afternoon.
With a sob that came from somewhere deep in my chest—shame and need twisted together so tightly I couldn’t separate them—I reached my right hand between my legs. My fingers found the tight pucker of my anus, and the moment I made contact, I cried out.
The sensitivity was shocking. Overwhelming. As if the seal on my pussy had somehow redirected all sensation to this forbidden place, making every nerve ending there hyperaware. Even the lightest touch sent sparks of sensation radiating outward, and I felt my whole body shudder.
“Oh, god,” I whimpered, my left hand pressing harder against the bed for support.
I bent further, arched deeper, presenting myself more completely. The motion was instinctive, my body knowing what it needed even as my mind rebelled. My finger circled the tight opening, spreading the lube, and I felt myself clench against the touch.
“No… no… no…” The words fell from my lips in a whispered litany as I pressed my fingertip against the resistance. The muscle fought back, refusing entry, and I had to take a shaky breath and try to relax.
“You look so, so beautiful, Laura, you naughty little slut.”
Mike’s voice came from the doorway, and I froze. I hadn’t heard him approach, hadn’t known he was watching. My face blazed like a bonfire as I realized he’d seen everything—the way I’d arched my back, the desperate sob, my finger working between my legs.
“Keep going,” he said, his voice warm with approval. “Don’t stop on my account.”
My finger pushed past the ring of muscle, and I gasped at the intrusion. The sensation was strange—not quite pain, but an intense pressure that made my sealed pussy throb with renewed need. I worked my finger deeper, the lube making the glide easier, and felt my hips rock forward involuntarily.
“That’s it,” Mike murmured. “In and out now. Just get used to how nice it feels to have something there because your sponsor wants it that way.”
I turned my head over my shoulder, needing to see his expression, needing some anchor in the storm of sensation overwhelming me.
“Eyes forward,” Mike commanded, his voice sharp.
I snapped my gaze back to the wall in front of me, my heart hammering.
The loss of visual contact made everything worse—or better, I couldn’t tell which.
I could hear him behind me, could sense his presence watching as I worked my lubed finger in and out of my bottom hole, but I couldn’t see him.
Couldn’t gauge his reaction. Couldn’t prepare for what he might do next.
The power dynamic crashed over me with devastating clarity. He was standing there fully clothed, completely in control, watching me perform this obscene act because he’d told me to. Because he owned me. Because I’d accepted his money and given him the right to make me do whatever he wanted.
And to my absolute horror, I felt fresh wetness gathering at the tiny opening at the bottom of my seal as I thought it through.
The arousal was unmistakable, trickling out in response to my own degradation.
My pussy clenched hard, trying desperately to find sensation that the seal prevented, and I realized with dawning shame that this—being made to finger my own bottom while my sponsor watched—was turning me on more than anything I’d ever experienced.
Because he told me to, I thought, the realization hitting me so hard I felt dizzy. I’m doing this because my sponsor commanded it, and that’s what makes it so intense.
Having him make me do it somehow amplified everything.
The need in my sealed pussy, the desperate aching throb, the way my whole body trembled with frustrated arousal—all of it was more urgent because I wasn’t choosing this.
Because he’d decided it was time for me to learn, and I had no choice but to obey.
“Add another finger,” Mike said from behind me.
I whimpered but obeyed, squeezing more lube onto my hand and working a second finger in alongside the first. The stretch was immediate and uncomfortable, my body resisting the intrusion.
I had to go slowly, breathing through the discomfort, my left hand gripping the mattress so hard my knuckles went white.
“Focus on how it feels,” Mike instructed, his voice taking on the patient, teaching quality. “The stretching. How despite the discomfort, it’s adding to your arousal.”
He was right. God help me, he was right.
The fullness, the slight burning sensation as my body accommodated both fingers—it sent sparks of pleasure mixed with discomfort straight to my sealed pussy.
I felt myself clench rhythmically, my hips rocking forward in that involuntary seeking motion I’d learned earlier.
“When I fuck your ass,” Mike continued, and the crude words made me clench around my fingers, “that stretching will help you feel proud, even when I’m using you hard, going deep. Proud that you can serve a man’s darkest desires that way. That you can take what he needs to give you.”
The thought sent a new wave of need coursing through my nervous system. I worked both fingers deeper, my breath coming in ragged gasps as the discomfort slowly transformed into something else. Something that made my sealed pussy throb with desperate need.
“Now take the plug,” Mike said, and his voice was suddenly much closer. Right behind me. “Put it in your bottom.”
I glanced at the small silicone plug sitting on the bed in front of me, then reached for it with trembling fingers. My other hand withdrew from my anus, leaving me feeling oddly empty. I positioned the tapered tip against my lubed opening and began to push.
To my surprise, it slid in easily—much easier than I’d expected after working my fingers there.
The plug was designed for this, I realized, the gradual taper allowing my body to adjust and accommodate.
I felt the widest part stretch me briefly, and then the plug seated itself fully, my muscles closing around the narrow neck.
“Oh,” I gasped, because it felt… good. Shamefully, intensely good. The fullness, the constant pressure, the way it made me hyperaware of that forbidden place—it all sent sparks of sensation radiating through my core.
Then I felt Mike’s hand cover mine where it still rested on the base of the plug. His fingers intertwined with mine, and he began to move the plug—not removing it, but shifting it, angling it, creating new sensations that made my knees nearly buckle.
“Come for me,” he commanded, his voice low and dark.
The words hit me like lightning. I was going to come. I knew it with absolute certainty—this was going to be even bigger than the orgasm over his lap, even more overwhelming than anything I’d ever felt.
Mike pushed firmly against the base of the plug, driving it deeper, and then his lips were at my ear, his breath hot against my skin. “I can’t wait to have my cock here,” he whispered. “Can’t wait to feel you squeeze around me while you take it.”
The orgasm crashed through me like a tidal wave.
I screamed—an actual scream torn from my throat—as every muscle in my body convulsed.
My sealed pussy clenched so violently I thought I might pass out, my anus gripping the plug with rhythmic pulses I couldn’t control.
The sensation radiated outward from my core in waves that seemed to go on forever, each one more intense than the last.
My arms gave out and I collapsed forward onto the mattress, my whole body shaking uncontrollably. I couldn’t breathe, couldn’t think, couldn’t do anything but feel as the orgasm continued to roll through me in aftershocks that left me gasping and sobbing into the comforter.
Through the haze, I heard a beep from Mike’s phone.
“What…” I managed weakly, my voice muffled against the bed. “What was that?”
“Your sensor,” Mike said, and I could hear the satisfaction in his voice. His hand stroked my back in small soothing movements. “It just confirmed that you’ve had a breakthrough in the amount of sexual arousal your body can feel.”
I couldn’t process the words. My mind felt like it was floating somewhere outside my body, disconnected from the trembling mess of sensation that was my physical form. The plug in my bottom sent constant sparks of awareness through my core, and my sealed pussy still clenched with aftershocks.
Mike’s hands moved to my hips, gently guiding me onto my side on the mattress. He climbed onto the bed beside me and gathered me against his chest, his arms wrapping around me with surprising tenderness. One hand stroked my hair while the other rubbed slow circles on my back.
“Breathe, sweetheart,” he murmured against the top of my head. “Just breathe. You’re safe. I’ve got you.”
I found myself curling into him, my face pressed against his chest, my body still trembling uncontrollably.
His warmth surrounded me, grounding me, pulling me back from wherever I’d gone during that devastating orgasm.
The hand in my hair continued its gentle stroking, and I felt tears streaming down my face for reasons I couldn’t quite name.
“That’s it,” Mike said softly. “Let it out. You did so well, Laura. I’m so proud of you.”
The praise made something warm bloom in my chest even as I continued to cry. I didn’t know why I was crying—from relief, from shame, from the overwhelming intensity of what had just happened. Maybe all of it at once. But Mike just held me, patient and steady, letting me come apart in his arms.
Gradually, my breathing steadied. My trembling subsided to occasional shivers. The fog in my mind began to clear, and I became aware of where I was—naked in Mike’s arms, the plug still seated in my bottom, my face wet with tears pressed against his expensive sweater.
“Better?” he asked, the warmth in his tone seeming to warm my body, too.
I nodded against his chest, not quite trusting my voice yet.
“Good.” His hand moved from my hair to cup my chin, tilting my face up to look at him. His eyes held mine with an intensity that made my breath catch. “I want to talk to you about something.”
My stomach flipped. What now? What else could he possibly want after everything that had already happened tonight?
“You mentioned earlier that you were interested in philanthropy software,” Mike said, and the shift in topic was so unexpected that I blinked in confusion. “Like I told you, I’ve been thinking about that. About ways to use my resources more meaningfully.”
I stared at him, trying to make my brain function properly. He wanted to talk about software? Now?
“I want you to come up with a proposal,” he continued, his thumb stroking my jaw. “For developing a philanthropy app.”