Page 72 of Chasing After You

I pushed forward the machine, lining up the head of the large, bumpy dildo at the end of the pole into his opening. Flicking the switch on, I watched in sadistic delight as the ten-inch fake cock disappeared into him, knowing that those bumps would press on all the best spots, just like my piercings had. I adjusted one of the control knobs on the machine, making the thrusts vary in speed and power.

Before leaving the room to shower, I knelt down in front of him and sloppily licked his lips, greedily tasting my own cum from when he’d blown me.

* * *

I knew Josh would panic if he woke up without me beside him, so I tried to stay as close as possible to him while he was out. Depending on how his body had reacted to the drug, he could stay unconscious for anywhere between six and twelve hours.

I was anticipating somewhere between six and nine hours, just based on his body composition.

After a long shower, I returned to the playroom, checked that he was still asleep, and poured a generous amount of lube onto the dildo that was still fucking into him.

I then slept for two hours on the freshly cleaned dungeon bed, setting an alarm on my phone. When it sounded, I groggily got up, checked on him again, added more lube, and jacked off onto his toned back.

I went back to sleep for another three hours, waking up to the sound of soft moaning. He was definitely not awake, but neither was he entirely unconscious. I poured the rest of the lube onto his swollen rim, emptying the bottle.

And then, I waited.

His lips parted slightly as he stirred. I watched the very beginning of movement as his body awakened—the flutter of lashes against flushed cheeks, the twitch of one of his fingers.

I leaned forward from the chair where I’d been sitting against one of the walls, elbows on my knees, heart tripping in my chest. I wasn’t scared. Not really. Just… aware.

Aware that if he woke up and realized what I’d done, he might not look at me the same way that he had last night. And I’d worked so hard for that.

But also, maybe he wouldn’t be mad. Maybe he’d feel how warm and safe he still was. Maybe he’d understand that I only ever did things that were best for him.

His brow twitched.

“Josh…” I whispered, soft as a thread unspooling. “It’s okay. You’re safe. Open your eyes, angel.”

A low hum answered me. His eyes cracked open, unfocused and hazy.

He looked at me. Not sharply—no suspicion, no anger—just dazed, like waking up in a strange place you don’t quite recognize.

“There you are,” I said, forcing calm into my voice. “Hey, you with me?”

He blinked slowly. “…Dori? W-what…hngh—” A ragged moan forced its way out of his chest as the dildo fucked into him.

“It’s okay, just give in to the pleasure. I’m just making you feel good, that’s all,” I coaxed.

He struggled weakly against his restraints, a look of confusion on his face. His body was flushed, droplets of sweat appearing sporadically across the expanse of his skin.

“I d-don’t—”

I turned the small knob on the machine, upping the speed to the highest level, and activated the vibration.

“What… what’s—ah—happening? F-feels so… so—”

“It feels good, doesn’t it?”

Josh mewled brokenly as the toy punched into him, his body trembling.He was too distracted to answer me, apparently.I grabbed a leather paddle from the wall and approached him. I rubbed his cheeks with my hands first, appreciating the bouncing motion from the machine fucking him.

Raising the paddle, I struck, landing a heavy blow to his ass.

“Ah,fuck!” Josh yelped at the sting.

I gave him another hit before leaning down close to his ear and saying, “I asked you a question.”

Tears cascaded down his face, confusion, worry, and arousal all swirling around in his gaze. “Dori, p-please,” he cried, struggling harder against the restraints of the bench.