Olivia and the Pirate Captain

The fighting was over quickly. The survivors from the merchantman were on their knees on my deck.

"Well, now," I said. "What have we here?"

"A sorry lot, Captain," my first mate said, shoving a young woman forward. "Just a hold full of cotton, some slaves, and this one. The governor's daughter."

"You will ransom me!" she said, her voice full of pride. "My father is a wealthy man!"

"Is that so?" I circled her, my hands clasped behind my back. "Strip her." My men needed no second order.

"Please, help me!" she cried out, looking from man to man, and then started screaming and clawing my men. Her dress, soaked from when we'd fished her from the sea, was ripped from her body. My first mate, a brute of a man with a nasty scar down his cheek, tore off a piece and formed a gag which he wedged into her mouth.

She stood there, trembling, her screams muffled by the gag, her arms cruelly pinned behind her, which made her firm breasts jut out in front of her.

I flicked a nipple and smiled at her. "So your father is rich, is he? Well, let's see if he'll still be inclined to pay for you when we're through with you."

To this my men laughed, and she screamed and the little hellion tried to kick me in the balls.

"Take her to my cabin and string her up." I turned to the others on their knees. "As for the rest of you, a simple choice. Join my crew, or take a walk off the plank." I heard them begging as I turned around to my first mate.

"What about the slaves?"

"We'll select the good ones that have resale value in Port Dorado."

"Good. Give some of them to the men to enjoy. Make sure they don't damage them too much. And pick a couple that are suitable to join our crew. Not too many, though, we don't want trouble."

"Aye, Captain."

"Good, then join me when you're ready, we have a hell cat to break."

I went into my cabin. My men had strung her up, her arms pulled tight above her head. A spreader bar held her legs apart. "There'll be no kicking from you now, my dear." I circled her slowly, examining her. I prodded her flesh, squeezed her nipples. She kept making noises into the gag, trying to pull away from my hand.

"Now, now," I said. "Tell me, girl. How many men have had you here?" I pushed a finger into her asshole.

She muffled a squeal against the gag and shook her head, twisting her hips away from me.

"Nobody, you say? Well, we will have to remedy that soon, won't we."

I moved in front of her. She looked terrified.

"And how many lovers have sampled this pussy, I wonder... Oh, dear. Is this why you've been so quiet?" I removed the gag from her mouth.

"You monster... How dare you lay hands on me, you brute. My father will have..."

I slapped her, hard. When she opened her mouth to speak again, I slapped her several more times.

"Now, we can go on like this for a long time. I don't mind. And when I'm finished, I'll gag you, fuck you, and then give you to the men. So you decide."

"I—" Another slap.

This time she kept quiet. Her cheeks were red on both sides; it actually looked good on her. I'd have to remember that.

"Good. Now answer my question. How many lovers have you had?"

"None. I am untouched. My father would never allow—"

"You lie," I said, putting my hand on her cunt and squeezing until she squealed.

"You are no virgin, at least not here." I squeezed her again. "That ass of yours is tight, so I'll give you that. Now answer me."

"No, please!"

"Tell me how many lovers you've had."

She looked at the floor. "None. Only my brother..."

I chuckled. "Well, I cannot blame him with a beauty like yourself. Does your father know?"

Her voice was a whisper. "Yes. That is why I am being sent to England to be wed."

“I see.” I ran my hands over her body again, enjoying the way she shivered under my touch. “How old are you? Twenty?”

"Nineteen," she gasped as my fingers pinched her thigh.

"Did he rape you, or did you entice him?" I leaned down to take one of those pale nipples into my mouth. "Answer me."

She moaned and turned her head. I bit down, hard, on her nipple, then looked up to see tears welling in her eyes.

"He, he watched me sometimes," she stammered. "While I bathed. Or he would touch me while I slept. He wanted more, but my mother..."

"So you enticed him." I pushed a finger into her tight passage, making her gasp. "Tell me how."

Her blush deepened. "No... I cannot... I... I couldn't resist it anymore and I, I made him fuck me..."

"You what?" I said, working my finger deeper. "How did you make him?"

"Oh," she gasped, her head falling back as my finger moved inside her. "He was in the bath... and... I went to him, undressed, and joined him in the tub. I, I kissed him, and... he grabbed me... and we did it, there."

"Well, nothing wrong with that, at least where I come from, sweetling. A sin would have been failing to do what you really wanted. And since you are on my ship now, my rules apply. Fucking your brother out of lust... that's no sin." I circled her little clit, teasing it, feeling her twitch.

"Please..."

"Ah, Sam," I said as my first mate entered my cabin. "See for me. How many fingers fit inside this girl's pussy?"

She shook her head. “No, no, please not him.” Her legs strained against the spreader bar.

"Sweetie, when I fingered you just now you were moaning in pleasure, so make up your mind. It's going to happen regardless."

My mate's big fingers rubbed her entrance. She tried to stifle her cries. Sam slid one finger in.

"Tight, but she can take more."

"Put two fingers in her. Stretch her." I moved behind her and gripped her ass, massaging it, digging my nails into her soft skin as I watched her writhe. My mate put in a second finger and pumped it in and out of her cunt.

"She likes that," I said. "Do you want more, sweet thing?"

"Please don't, I'm a good girl..."

"No, you're not. If you were, your pussy wouldn't be getting so wet, now would it? I can see you dripping around his fingers." I slapped her ass and she jerked. Sam took his fingers out and held them to her mouth.

"Lick them, you dirty little slut." She hesitated for a moment, then stuck her tongue out. I grabbed her hair and pushed her mouth onto Sam's wet fingers.

"Taste yourself. All that sticky sweet nectar." She moaned as she lapped at the two fingers.

"Now, this passage," I said, pushing my finger against her little rosebud. "Ever put anything up your ass?"

"No! No please!" She began struggling in earnest, her body pulling at the restraints. "Not there, I beg you, that is dirty, only the slaves get penetrated there." I was starting to like this girl more and more. I hated it when they stopped resisting too fast, so I pushed in my thumb and wiggled it around. Her whimpers grew more frantic as Sam spread her asscheeks apart.

"She is so tight here, Captain," he grunted.

"Well, we'll just have to loosen it up then, won't we? Get some oil and fuck her with your fingers."

I walked around to stand in front of her and presented her with my soiled finger. She looked horrified, her mouth firmly closed.

"Now, my darling, we'll have none of that." I pinched her nipple with my other hand, forcing her to open her mouth, and I shoved my fingers inside.

"If you dare bite me, I will smash your teeth. Do you hear me?" I pinched her other nipple even harder as she gagged on my hand. "I am going to remove my hand, and you will suck my fingers clean. Have you understood?" I gave her pussy a hard squeeze. She nodded quickly, grunting an assent. I pulled my hand out slowly and let her lick my fingers clean. Then I drew my hand back as if to slap her. She flinched. Instead, I cupped her face and gave her a kiss.

"I think you and I are going to get along fine, aren't we?"

"No... you, you won't... Ahhh!" she screamed when Sam started fucking her ass with two big fingers.

"Don't worry," I said. "Open wide. Let me have a look at your teeth. Just to see what my cock is going to encounter when it makes its acquaintance with your throat." I ran my finger over her teeth. "Perfect." I slipped a finger inside her mouth, moving over her tongue, pushing in as far as it would go. She was panting around my fingers. Then I added a second, moving in deeper. Her eyes were wide.

"Resist the urge to bite, my dear. I swear if you bite my hand or my cock, you're going to regret it for the rest of your very painful long life." She started struggling, choking, trying to speak.

"Oh yes, we will teach you to suck a cock and to swallow. We will use your throat, and we will fill you to the brim with cum, so you had better get used to it." I slipped a third finger in her mouth, fucking her mouth until drool ran down her face.

Sam chuckled. "Her ass is loosening up nicely, Captain."

I removed my hand, undid my breeches and took out my cock, already hard as a rock.

"See this, my dear? This is what's going up your cunt soon. While Sam is going to take care of your ass, this big fellow is going up your pussy."

“No, please no!” She shook her head, her face red and tears streaming down her cheeks. I slapped her, hard, while Sam finger-fucked her ass, two fingers deep in her tight little hole.

"Show some enthusiasm, girl. It’s not every day you get to fuck Captain Gray and my mate Sam. A little gratitude won’t hurt. Now, take a look at this beautiful big cock and imagine how it will feel, ripping you apart.” She stared as my cock bounced in front of her.

I took a step closer and pointed it at her cunt. Behind her, Sam had started undoing his breeches, and now his huge member was sliding in the crack of her ass.

"Sam's gonna take your ass, while you scream on my cock. Don't worry. We'll make you like it, girl. Even beg for more." Sam pressed the head of his cock against her asshole while I did the same to her pussy. With one shove, he was in. Her eyes widened and she screamed. Her ass must have been on fire, stretched by his huge cock. Slowly he slid out again and back in. Then I thrust into her cunt.

"Oh God, it hurts!" She arched her back, but Sam held her tight, her head falling on my shoulder. She whimpered as I pounded into her.

"So tight," I said through gritted teeth, "your cunt is gripping me like a fist."

Sam kept a slow rhythm. He didn't need to go faster. Soon she was moaning with each of our thrusts. Her ass was filled to the hilt with his thick, long cock, while I enjoyed the sweet suction of her tight pussy.

We went on like that for some time. Her breathing quickened. Then, as I felt my balls tightening, her body went rigid and I came, hard and deep, as she convulsed in orgasm, Sam roaring behind her. We both stayed inside her for a while, and I stroked her hair. "Well done, sweet girl. Your first fucking is over." She sniffled in response.

When Sam pulled out of her, his come leaking out of her asshole, she whimpered again.

“Look at the mess you've made of the Captain,” he said, grabbing her chin and turning her towards me.

“Untie her, Sam. So she can clean our cocks.”

I nodded to Sam, and he untied her. The ropes fell away, and the spreader bar was removed. Her legs gave out and she collapsed to the floorboards.

I took a handful of her hair. "Come here. Time to lick us clean." Her mouth opened, and I guided my softening dick past her lips. She cleaned our combined spend from me, her face still flushed from the fucking.

Sam pushed his dirty cock toward her. She took it into her mouth, her movements hesitant.

"Suck it, girl. Get it all."

She gagged, her cheeks hollowing around his girth.

“Don’t you dare…” Sam threatened, raising his hand, and she tried harder, letting the filthy cock slide deeper into her throat. When we were satisfied, I pulled her to her feet.

Sam wiped his cock on her thigh. "Shall I pass her to the men, Captain?" He looked her over, her body slick with sweat and our seed.

"No, Sam. She is mine for now. She may yet have other uses."

He laughed at that. "Aye, sir. Other uses indeed…”

"Yes. Now go, and make sure the men aren't damaging those slaves too much. They need to be fit for selling."

"Aye, Captain."

He winked and shut the door behind him. I lifted the girl; she was exhausted, shivering in my arms. I carried her to the bed and laid her down. "You can sleep for now, sweetling," I whispered, tucking the covers around her. Then I took her wrists and bound them to the bedpost. "Just in case. Sleep." Her eyes closed and she fell asleep. I returned to my charts.

***

When she woke the next morning, I was already inside her.

"I am... where..." Her voice was thick with confusion as I slammed my hips into hers. She gasped.

"On my ship, of course, in my bed." She looked down, saw my cock inside her, and tried to pull away. The ropes held her fast. She let out a cry of despair. I stopped moving.

"What a lovely sight, you waking up full of my cock. Your body seems to have adjusted quickly." I bent to kiss her, biting her lip when she tried to turn away. I pinched her nipple, hard. "I want to hear you beg."

"Please, don't..." Her voice trembled.

"Don't?" I began moving again, pulling almost all the way out, then plunging in deep. Her cries filled the cabin. "Now wrap your legs around me. Come on, don't be shy. Give in to your body." I took her ankles and pulled her legs up, then placed them around my waist.

"Oh please... please..."

I went even faster, her pussy squeezing around me. "That's it, my girl. Show me how much you love this. Beg me for more. Beg me for my come deep inside you." I slammed harder.

“You were not a virgin. But I bet this is the best fucking you ever had.” I slapped her breast and she cried out. “Say it.”

"I, I love your cock. It's so big, I, ohhh..."

"Say it."

"Please... please fuck me harder." She threw her head back, her body clenching around mine. I came shortly after, shooting my seed deep into her.

She panted. I stayed on top of her for a moment, then pulled out.

"Have something to eat. And you will serve me, naked, as befits your new position." I untied her wrists, then watched her slide out of bed and stretch her arms.

She winced. I could see the red marks where I had gripped her hips and ass cheeks. "What is my new position, Captain?" she asked quietly, rubbing her wrists.

"Why, my fucktoy, of course. And you may call me Dafydd when we are alone, Captain when my men are around. And what shall I call you?"

"Olivia," she said.

"A beautiful name for a beautiful girl. Come. Eat, and tell me about yourself. You said something about a rich father?"

I pushed a plate toward her and watched her hesitate, then sit down opposite me. Her eyes were fixed on the eggs, but she made no move to take them. She was rigid, in her chair, and did not answer my question.

"Have I not been clear? You may eat," I repeated. I had already eaten, and the sight of her hungry stare made me impatient.

"I'm not hungry."

“Right, in that case,” I said, and rose, catching her arm in one movement and bending her over the desk, sweeping it clear in the process.

“When I tell you to do something, you do it, even if you don’t want to.” I took the crop hanging on the wall and struck her with it.

“Ahhhhhh!” she cried out and struggled. I held her arm in an iron grip and swatted her ass twice more, watching it redden. Her breathing became more erratic as I smacked the tender insides of her thighs, and finally her pussy.

“I...I’m sorry! I'll do it, please, stop.”

“Too late for that. Now stay there. I am going to cane you. You’re getting a baker’s dozen. If you move, I double it.”

She began crying and whimpering, her legs shaking as I went to fetch the thin cane.

"Dafydd...please..." she pleaded. "I've been a good girl, I will eat the food, please don't..."

"Stay down," I said, nudging the cane against her ass. "Look at it. Have you ever been caned before?"

"No..." she stammered against the desk.

I ran a hand over her flank, feeling her tremble. "You are about to learn. It's a most effective training tool." I drew the cane back.

"You will count every stroke, thank me, and ask for the next one. Understood? One mistake and we start again."

I struck her, hard, across the cheeks of her ass.

She screamed, a fresh wave of tears running down her face.

"One!" she gasped. "Thank you. May I have the next one?"

A deep red line rose on her skin. The next two followed in quick succession.

"Three, thank you... four, thank you." She sobbed with each strike, her bottom turning a mottled red and blue.

After the sixth, I stopped.

"Do you think I should stop here?"

"Oh please, Dafydd, yes. Please don't..."

I slapped her cunt, sharp and stinging. "You do not decide that, do you?"

"Five more," she gasped, trying to regain her composure. I stroked the inside of her thigh, enjoying how her leg twitched. "Five more. I'll take them. I can do it. Please just give them to me and be done with it."

"That was seven," I said. "So with another for the mistake. That makes eight. Now ask for the next."

She looked over her shoulder at me, her face a mess of tears. "Please… give me the next one, Dafydd."

"Good. You will get two more as normal, and you will show your gratitude by coming to give me a kiss. I will tell you where each time. Understood?"

"Yes, sir."

I gave her the seventh. She said thank you and got up, looking at me for directions.

"I said every other stroke, so we’ll have to repeat the seventh one again."

"No, I'll be good," she said. "Let me kiss you, please."

"Eager now, are we? But first, the mistakes. Bend over."

I delivered the seventh again, swift and hard. She shrieked, the red lines on her skin brightening.

"Seven. Oh...!" she moaned. "Can I please have the next one, sir?"

The next one came hard, a thin red stripe just above the others.

“Get up.”

She rose, wincing, her hands going to her striped ass.

“No hands,” I said, and she let them fall to her sides. I pointed to the floor. “Kneel. Kiss my feet.”

She sank to her knees, pressing her lips to my boots, her body shaking. I nudged her with the toe of my boot.

“Back over the desk.”

She complied, her reddened bottom presented to me again. Her pussy was slick now. I drew the cane back.

“Nine! Thank you! May I have the next?” she cried as the thin line blossomed on her skin.

“Ten!” she sobbed.

I paused. “Kiss me.”

She stumbled to her feet and pressed her mouth to mine. I held her, one hand on the small of her back, the cane tapping against her bruised ass.

“Again,” I ordered when she pulled away. I pointed her back to the desk. She bent over it without a word.

I delivered the eleventh stroke, nicely parallel to the others. I had a reputation to keep up with my men

“Eleven! Thank you… may I have another? Twelve...Thank you, thank you,” she babbled. Then she hobbled back to me and pressed her lips to mine.

I spread her legs, pushing two fingers inside her cunt.

"You're soaking, Olivia."

"I, ohh... please, I'm close, oh please... can I, can I have more?"

“Are you enjoying this? Your caning? Do you like how it feels?"

“Yes. It's hot, I feel so hot, please don't stop... can I, please... more?"

I took out my fingers, and licked them slowly before I gently pushed her away. She whimpered and stumbled to the desk, where she bent over and thrust her bottom up.