Page 66 of Paid to the Pirate

I gave Charlotte an indulgent look. “Only because you begged so sweetly. Now help me punish you by spreading those legs real wide this time. That’s my girl, my good girl.”

I tapped her clit a few times. She was so wet I could smell her without bending down. I’d never punished a girl in such a manner before, and didn’t know how much Charlotte could take, so I erred on the side of caution and only struck her with medium force. Her cry was loud enough that I knew any man nearby would have heard it. But it tapered off into a deep, throaty moan, the sound of which went straight to my cock.

I couldn’t wait any longer.

Freeing my erection, I bent down and slid gently into her pussy. I was unsure whether Charlotte saw as it as a reward -- quenching some of her throbbing desire -- or as a punishment, the rough scratch of my hair chafing her sore and swollen cunt.

“Tell me you like it,” I coaxed, driving in and out of her slowly. “Tell me you like it when I punish you.”

“It - it hurts,” she moaned.

“But you like the pain, don’t you?”

When she didn’t answer, I rammed her hard.

“Don’t you?”

“Yes! I do,” she cried, tapering off in another moan.

“The first part of your punishment is over,” I said, reluctantly withdrawing from her cunt.

“F - first?” she echoed, eyes wide as a doe’s.

Ignoring her, I retrieved what was necessary from the small set of drawers built into the ship’s walls and serving to hold my wardrobe. I made quick work of tying Charlotte’s wrists together and securing them to the hook behind the bed. I let her see the handkerchief and long sash.

“What are you doing?” she asked in a timid, suspicious voice.

Not replying, I watched her face color with surprise and confusion as I began pumping my cock. It took a minute, but I spilled my seed into the handkerchief, filling and soaking it.

Poor Charlotte had no idea what was coming.

“Don’t worry,” I said, grinning. “I’ll be hard again in a few minutes. In the meantime…”

I grabbed Charlotte by the hair, shoved the soiled handkerchief into her mouth, and tied the sash around her head, securing the wad of cum within. Charlotte scrunched up her face in displeasure.

“I should be offended,” I mocked. “But we’ll have plenty of time to train you to like my taste. And I don’t think you’ll be thinking about it soon enough…”

Her eyes widened when I withdrew my dagger, but she relaxed when she saw I only meant to pare the ginger.

“This is going in your arse,” I explained as I peeled. “You’ve never had anything in there before. It’s going to feel uncomfortable. But that alone isn’t punishment enough.”

Charlotte’s eyes bulged as I used her juices to lubricate her anus, sliding my own finger in to prepare it for the ginger. She squealed and tried to move away, but I grabbed her hips to keep her in place. With purposeful slowness, I slid the ginger inside and stood above her.

I looked down at Charlotte, trussed up upon my bed. Her mouth was filled with my seed and her heavy breasts swelled, begging for attention. Her face reddened with embarrassment and desire as ginger root stuck lewdly out of her arse.

I’d never seen her more beautiful.

When her eyes rounded, I knew it had started to work.

“It burns, doesn’t it?” I grinned.

I took her moaning and head-thrashing as a reply.

“I’m going to really fuck you now. It might hurt your sore cunt and I imagine the pain in your rectum is even worse. But I have a reward for you too, Charlotte,” I said, grinning. I wasn’t sure if she’d see it as a reward in the moment. In fact, it would be further punishment, for now. But later… later, she’d come to look back on it and thank me.

I hoped.

“I’m not going to stop fucking you until you come.” Her eyes snapped to mine. “You’re going to have to find a way to relax, to enjoy the pain and to enjoy what I’m doing to you. Because the longer you take to come, the more it’s going to hurt. And if you take too long, I’ll simply replace this ginger with a fresh one.”

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