“Put the bottom of your shoes on the floor and keep them there. No kicking and squirming around.”
To my relief, he was bending the bobby pin a little, so it wouldn’t be on me “full strength.”
“Part your pussy lips,” he said when he was done. “I’m going to need two hands for this delicate maneuver.”
He used two hands and his mouth, sucking at the folds of my sex, revealing my rapidly swelling clit. I threw my head back when he dragged his tongue across the sensitive button.
“That feels good, doesn’t it?”
“Yes, Sir.”
“You taste delicious, wicked and sweet. What’s pleasure, though, without pain?”
He positioned the hairpin over my clit and slid it carefully onto the engorged, throbbing nub. The pain was immediate, and nearly unbearable in my heightened state of arousal.
“Oh… Oww…” I bucked my hips, taking care to keep my shoes flat on the floor as he’d told me. He stood above me, watching me suffer for a moment, pure delight on his face. I squeezed out a few more tears, blinking through the pain.
“I won’t leave it on forever,” he said, helping me up. “Although we might look into some intimate piercings in the near future. That might be fun.”
“Yes, Sir,” I breathed, tottering on my heels.
He backed me up to the rack with a stare that had me shivering. My legs were bound first, spread apart. My poor clit ached as the air caressed it. “How… How long…?” I began in a quivery voice.
“As long as I think you need. Arms up, please.”
I swallowed. He bound my wrists to the top of the rack, spread as wide as my legs. My breasts were exposed, along with my pussy, by The Gallery uniform. I stretched my body, trying to get comfortable since I couldn’t get away. Honestly, I didn’t want to get away, even when he picked up the hated clover clamps. But as he turned and saw the suffering on my face, he paused.
“If I’m going to clamp your clit with a hairpin, I might as well use them for your nipples too. It’ll provide a nice circle of continuity.”
Continuity? More like agony. Ugh, why had I used so many pins in my hair? I should have known my crown of braids wouldn’t survive this night intact. He took two of the pins he’d collected earlier and bent them open, just a little, as he’d done with the one he put on my clit. Like that one, these pins hurt like hell when he applied them. They gripped my nipples like little shark mouths, and no way were they coming off unless he bent them off.
“Ow, it really hurts, Sir.” I squirmed to try to soothe the pain, but it only turned him on more. He shed the rest of his clothes and kicked off his boxers. Tall, beautiful, strong Milo, ready to hurt and fuck me. He stood in front of me and lifted my chin, gazing into my teary eyes.
“Do you remember the safe word, baby?”
“I don’t need a safe word,” I said. “This is our Gallery. Let’s not depend on safe words, because I know you’ll keep me safe.”
I could tell my request touched him. I could also tell he wasn’t sure about the idea. “I’m going to use a cane on you, Alice. Canes really hurt. Then I’m going to fuck your ass without plugging you first. You sure you don’t want that safe word?”
I shook my head, excited and terrified. “No, Sir.”
He studied me a moment, then turned away, picking up his tie from the chair where he’d laid it. At first I thought he’d blindfold me, but then I remembered him saying that blindfolds weren’t allowed when safe words weren’t used, like in The Gallery. The eyes say more than safe words ever could, he’d told me, if the Dom’s paying attention.
No, he used his tie as a gag instead, shoving it between my lips and tying it tightly behind my head. I could breathe, but talking was out. When he finished tying it off, he gave it a little shake, and my whole body trembled. I was bound and speechless, utterly helpless in his hands.
“These little pins hurt, I bet,” he said, flicking my nipples. When I nodded, he offered dubious comfort: “I won’t leave them on too long. It doesn’t take that many strokes to break someone down with a cane. But after, when I fuck you…” His lips curved in a sadistic smile. “I’ll make that last a long, long time before I let you come.”
I moaned. It sounded strange and muffled behind the gag, and so erotic. I’d never been gagged before, so I moaned again to get used to the sound. Milo walked behind me and I felt the cane tap against my ass. He’d never used one on me before, so I wasn’t sure what to expect, but I knew it wouldn’t be pleasant.
Not. Pleasant. At. All. Owww. When the first stroke came, I yowled at the shocking, blistering sting. Now my muffled voice sounded strangled. He waited a moment, steadying me with a hand on my waist. How many? I wanted to beg. How many of these do I have to take? This really hurts!
Instead I could only groan as another blow fell. It was just a small flick of his wrist. I could see the movement if I turned my head, but then everything went fuzzy when the thin, whippy implement connected. Three strokes. Four. A sob escaped my throat, and drool started soaking through my improvised gag. If I didn’t ruin his tie with saliva, I’d ruin it with tears.
“Take a breath,” he said, slapping my face to catch my attention. When I crooned behind the gag, he did it again, a little smile curving the edges of his lips. “Everything’s okay. You can’t get away, right? Just take the pain, let it empty you out so there’s more room for my cock.” As he gazed at me, he spanked the four sore welts that throbbed in the center of my ass cheeks. I danced on my toes, mewling in protest, but I kept my eyes on his, because his expression was so warm, so beautiful and challenging.
“You’re my brave girl, aren’t you?”
I nodded, hoping he wouldn’t slap my face again, but kind of wanting him to slap me again. He spanked my ass instead, several hard smacks in succession as I wailed against the gag. The spanking was a different kind of pain from the caning, but still hot and cruel on my sore butt. He kissed my face, my nose and eyes, his lips coming away wet with tears. “You’re a beautiful crier,” he said, making me look at him. “We’re almost done, baby. Can you take four more?”
I didn’t think I could. I had no answer to give him, just the frantic tensing of my muscles.
“Okay,” he murmured. “We’ll see.”
The next stroke landed near the curve of my ass. I grasped the cuffs holding my hands and squealed behind the gag. It hurt so badly. Pure sadism, no pleasure. I understood that he needed that kind of sadism to get off, so I let my tears flow as the last three strokes came. I wailed and struggled, forgetting the biting pain at my clit and nipples because my ass hurt so, so bad.
He put down the cane after the last stroke and held me around the waist, kissing me, poking his cock against the hairpin on my clit, making it throb in concert with my wrecked ass. My butt cheeks felt like they were exploding, the heat and pain was so agonizing. He spanked each one again, hard and fast, to make things worse, or maybe to help diffuse the pain over a greater surface. Everything hurt. Everything felt squeezed and stung and punished by him.
After he watched me cry another moment, he eased the hairpin off my clit. I was so wet, it slid off easily, but it left plenty of sen
sitivity behind. “Poor baby,” Milo said, stroking the swollen button. “That was so mean. We’ll leave your clit alone the next few days, yes? So it can get better?” He laughed at my whine of protest. “And I’ll only fuck your ass, since your clit’s out of commission. Maybe we’ll go anal-only for a whole month.”
I gave him my most forlorn look, but my pussy pulsed at the picture his crass words painted. Anal-only would hurt. It would be dirty and naughty, the perfect way for a sadist Dom to torment his submissive.
“Don’t worry,” he said. “I’ll still let you come, if you can learn to do it from assfucking alone.”
As I moaned, he took the hairpins off my nipples. He squeezed and licked my breasts where they jutted from my bra, blowing hot air across them. My nipples were still hard, still ready for more abuse. He pinched them as he teased my clit some more, sliding his cock between my legs. I was still in pain, yes, but I was getting hot as hell at the same time. I moved my hips forward and whined behind the gag.
He reached above me to release my arms. “I told you, Alice, I’m not fucking your pussy tonight. Your ass is so red and striped. It makes your asshole a much more inviting target.”
The first thing I did when my hands were free was reach behind me to rub my sore butt, even though it was forbidden. Milo pushed them away from the throbbing welts. “No. If you want to do something with those hands, hold your ass cheeks open so I can lube you up. Or would you rather forgo lubrication?”
I made a frantic sound of denial, and he grabbed the bottle, liberally greasing my asshole. I could feel just from the pressure of his fingertips how tight I was, probably from the pain of my caning. He shoved a couple fingers in anyway, pushing the lube deep, making me squirm and moan behind the gag as he stretched me open.
When he was done, he guided me down onto my hands and knees, with my ankles still braced wide by the bar. It was an incredibly exposing position, especially knowing that Milo was behind me, preparing to invade my ass. He didn’t make me wait for it to happen. Holding my hip with one hand, and his cock with the other, he probed my tight hole.