Chapter 21
Laura
My face blazed with heat. My hands trembled as I obeyed, folding them behind my back and gripping my own sore bottom, feeling the base of the plug shift between my cheeks as I knelt at his feet.
My knees pressed into the plush carpet, my thighs squeezed together, and every inch of my skin was electric with shame and anticipation.
Mike wrapped his big hand around the shaft, stroking slowly, deliberately, bringing the broad head right up to my lips.
“Just the tip,” he said, guiding me. “Eyes up. Look at me.”
I made my mouth into a little o, barely touching the warm, vibrating flesh of my sponsor’s cock head.
I felt it pulse against my lips. My gaze met his, and I tried to hold it, even as tears stung my eyes and my whole body shook.
I gripped my punished bottom cheeks more firmly, a thrill of degradation passing through my whole body at the obscenity of the mere idea.
Mike began to stroke himself faster, holding the tip of his manhood right at my mouth. I realized with a strange, sudden jolt that this felt like the most exposed, the most vulnerable, the most seen I had ever been in my life.
“Kiss it now,” he growled, his thumb brushing my chin. “Your treat is almost here. You want to show me how grateful you are for this reward, don’t you?”
I nodded, unable to speak, pursing my lips to put a tiny kiss on the little hole, then opening my lips a bit more again, waiting, braced, desperate and mortified and so, so hungry for the approval in his gaze.
He let the tension build, his breathing getting ragged, his muscles bunching under his crisp shirt.
Then, with a guttural noise, he put his other hand on my head to keep me where he wanted me, with the tip of his cock right between my lips.
I felt the hot, salty flood hit my tongue.
It took all my self-control not to flinch, not to pull away.
Instead, I let it fill my mouth, pooling on my tongue, and swallowed it as best I could, just the way he’d taught me.
“That’s it,” he murmured, his hand gentle on my cheek now, guiding me to take another spurt, and another, until my mouth was coated with his seed. “Drink your treat, little girl. That’s a good girl.”
I swallowed, the taste strange but already familiar, the heat of it making me shiver.
He pulled back, still holding me by the chin, and wiped a thumb over my lips, collecting a stray bead of semen and smearing it across my cheek.
The gesture was so casual, so possessive, that I nearly whimpered with the shock of how much I liked it.
“Clean me up,” he said softly, and I licked him clean, careful to catch every drop, my face burning with the knowledge that this was what I was for now. When I finished, he tucked himself away and helped me to my feet, wiping my mouth with a napkin before kissing me softly on the lips.
“That felt lovely,” he murmured. “You’re learning very fast.”
He led me to the back of the jet, through a door and into a bedroom with an enormous bed, bigger than the one in my apartment, dressed in white sheets and pale gray pillows.
The windows were shaded, but the room was full of the sunset light as we soared westward, and the walls were hung with abstract art that looked impossibly expensive.
“Take off your dress,” he said, and I did, lifting it over my head. When my vision was clear again, I let out a little cry, because Elena the flight attendant was standing there, her hands extended.
“Elena will put your dress away,” Mike explained.
I saw nothing but professionalism in the other woman’s eyes, but the idea that she could see everything—my bare, sealed pussy, my spanked bottom, the base of the plug peeking out between the little cheeks—it nearly made me faint with mortification.
The tiny, knowing smile Elena gave, as if to say, You’re a billionaire’s fuck toy—I knew that the moment I laid eyes on you, so there’s no reason to be more ashamed because I can see you got spanked with a butt plug in your bottom… only made me blush hotter.
“Thank you,” I whispered, my reflexive manners taking over in the absence of my brain coming up with anything else.
“Of course,” she replied, taking the dress and moving to the closet to hang it up.
“You can go ahead and put the riding cushion on the bed, too, Elena,” Mike said. “Laura’s going to go for a little ride before dinner because she was a good girl.”
My face blazed. I held my hands at my side in little fists, working desperately not to cover myself because I felt that would only embarrass me further.
The fact that I had no idea what Mike meant about the riding cushion only made it all worse.
But the next exchange between the flight attendant and my sponsor brought it all to a new level of humiliation.
“Shall I put the dildo in place on the cushion?” Elena asked, as if it were the most natural question in the world.
“No,” Mike replied. “Laura’s a virgin, and she’s sealed down there until I decide to open her. It’s a new Selecta thing, I guess, to help her learn and to make her tighter. It’s super hot, I have to admit. Anyway, we’ll save the dildo for the trip home, when she can enjoy it.”
I stared at Elena as she nodded and disappeared into a closet I hadn’t even noticed, emerging a moment later with what looked like a firm leather cushion, maybe two feet long and a foot wide, curved in a way that made my stomach drop even though I still didn’t fully understand what it was for.
She set it carefully on the bed, adjusting it so it sat in the center of the white sheets.
“Will that be all, Mr. Gallagher?” she asked.
“That’s perfect, Elena. Thank you. We’ll ring when we’re ready for dinner.”
She left without another glance at me, closing the door behind her with a soft click that seemed to echo in my ears.
I stood there naked except for the plug in my bottom, my arms wrapped around myself, trying not to think about what had just happened—about the casual way Mike had discussed my sealed pussy with his employee, about the fact that she’d seen me completely bare and spanked and marked as his.
Mike sat on the edge of the bed and patted the cushion. “Come here, sweetheart. Straddle it.”
I approached on shaking legs, my face still burning. Up close, I could see the cushion was designed with a ridge down the middle, positioned exactly where—oh, god. My sealed pussy would press right against it if I sat on it the way he wanted.
“Mike, I—”
“Sir,” he corrected gently.
“Sir,” I whispered. “What is this?”
“It’s a riding cushion,” he said, as if that explained everything. “You’re going to ride it for me. Show me how desperate you are. Show me how much you need to come.”
The humiliation washed over me in waves, but I climbed onto the bed anyway, my body obeying even as my mind reeled. He would spank me—whip me even. Wouldn’t he? If I didn’t do the obscene things he wanted?
I swung one leg over the cushion and lowered myself down, gasping as the ridge pressed directly against my seal. The pressure was immediate and intense, and the plug in my bottom shifted, making me acutely aware of both sensations at once.
“That’s it,” Mike murmured, his hand stroking my thigh. “Now rock your hips. Hump it like the desperate little slut you are.”
I whimpered but started to move, my hips rolling forward and back, the ridge of the cushion creating pressure on my clit, through the seal, and sending sparks of sensation through my core.
The plug shifted with each movement, and I found myself squeezing my muscles the way he’d taught me, creating even more pressure, more fullness.
“Good girl,” he said, his voice thick with satisfaction. “Keep going. I want to watch you work for it.”
I moved faster, one hand moving to my breasts to play with my nipples, my whole body focused on the building sensation. The combination of the cushion against my sealed pussy and the plug in my bottom was overwhelming, and I could feel myself getting close, so close—
“Stop,” Mike commanded.
I froze, my breath coming in ragged gasps.
My whole body trembled, suspended on the edge of release.
Mike’s hand moved to my hip, steadying me, and then I felt his other hand slide around behind me.
His fingers found the base of the plug, and he began to work it slowly, twisting it, pulling it partway out before pushing it back in.
The sensation was overwhelming—the fullness, the stretch, the constant awareness of being opened there.
“Please,” I whimpered, my hips trying to rock forward again on instinct.
“Not yet,” he said, his voice maddeningly calm. “I want to see how ready you are for the big one.”
My eyes flew open. I watched over my shoulder as he withdrew the medium plug completely, leaving me feeling suddenly, achingly empty. He set it aside on the nightstand and reached for something else—the large plug. The huge, terrifying one that I’d been dreading since the first night.
“Mike—sir—I don’t think I can—”
“Shh,” he soothed, his hand stroking my lower back. “I’m just going to play with your adorable little hole. Get you used to the idea.”
He squeezed more lube onto his fingers and began massaging the little ring of my anus, circling and pressing, making me gasp. Then I felt the tapered tip of the large plug press against me, and my whole body went rigid.
“Relax,” he murmured. “Just feel it. I’m not going to push it all the way in yet.”
He pressed the tip inside, just barely breaching the circle of muscle, and I cried out. It was so much bigger than the medium one. The stretch was immediate and intense, bordering on pain. He held it there for a moment, letting me adjust, then withdrew it completely.
“Ride the cushion again,” he commanded. “Nice and slow.”
I obeyed, my hips rolling forward, the ridge pressing against my sealed pussy. The emptiness in my bottom felt strange now, after being filled for so long. Then I felt the plug again, pressing, stretching, making me whimper as he worked just the tip in and out.
“Squeeze for me,” he said. “Show me how you can clench around it.”
I did, my core muscles flexing, and the sensation of squeezing around even just the tip of the huge plug while grinding against the cushion nearly sent me over the edge. I gasped, my movements becoming more desperate.
“Stop,” Mike said again, and I froze, tears of frustration streaming down my face.
He withdrew the plug and set it aside, then his fingers were there again, massaging, teasing.
This pattern continued for what felt like hours—he’d let me ride the cushion until I was close, then stop me and play with my bottom, sometimes with his fingers, sometimes pressing the large plug partway in, never quite filling me but keeping me constantly aware, constantly aching.
I had almost forgotten that the taboo scene was unfolding on board a private jet over the Pacific Ocean, and then a little bump and the unmistakable feeling of dropping fifty or a hundred feet added the exhilaration of momentary weightlessness to the helpless pleasure.
I cried out, coming terribly close to climax, hearing the rushing sound from the jet engines, remembering that I had become the property of a billionaire who was taking me somewhere amazing to enjoy me, deflower me, fuck all my holes with his huge, rigid manhood.
Finally, I was allowed to dismount. The cushion was slick with my need and the thought of Elena having to clean it—oh, my god, would she clean the plugs, too?—and put it away again brought a new wave of heat to my cheeks.
Mike gathered me into his arms, settled me onto his lap where he sat at the edge of the bed.
I collapsed against his chest and he held me even tighter.
I could feel his hardness through his pants, and it brought a tiny whimper up from my chest as I thought about what it meant: my billionaire sponsor wanted me that way, but he also had decided to take his time…
to savor the shameful, degrading claiming of my innocence.
And, at the same time, he wanted to cuddle, to hold me, to comfort me. He kissed the top of my head gently. He put his right hand on my head, his touch soft but also possessive… yet also affectionate and kind.
“It’s a lot,” he murmured into my ear. “But you need it, Laura. I hope you can start to accept that. You need all of it—the punishment and the pleasure and the training to please a man like me. I don’t need the data in the app to tell me that, as clear as that data is.”
My head moved back and forth in an automatic no, and I tried to say it, too. But a very different word came out of my mouth in a whisper.
“Yes,” I breathed. “Yes, sir. But…” I swallowed hard, burying my face in his shirt as frightening, terribly moving images of the future filled my mind. “But… please don’t whip me?”
“Oh, sweetheart,” Mike said, turning my face up and kissing me gently before he continued with his dark eyes gazing straight into mine. “I’m definitely going to whip you. Because you’re definitely going to deserve it.”
I closed my eyes, swallowing hard. I let out a little sob as again my head tried to shake in denial.
“I know you can’t admit it yet,” Mike said, his voice soft despite the dominance of his words. “But I know you know it’s true. You’re going to be naughty sooner or later, and that adorable butt of yours is going to get whipped, and I’m going to enjoy doing it.”