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The Captain loved her panicked clenching, but he wanted to teach her a lesson. Plus he had felt it when a girl beneath him had the cockroach inside her, her body jerking in pleasure, her muscles uncontrollably gripping his cock better then she could willingly provide. He would enjoy the Princess’s terror. “Put it inside her. Make her pleasure me.”

“AAAAAGGHH.” She screamed as loud as she could when she felt the pirate crouch down between her legs. She felt the cold glass tube pressed against her warm pussy lips, his hands slowly forcing it in. It felt as if a large cock was entering her, her insides split terribly by the twin shafts between her legs. She felt is spread inside her until it stopped.

“Get ready Princess. It doesn’t like me tapping on the glass. It will try to escape and the only way out is deep inside your hot tight pussy.”

She felt the tapping on the glass inside her pussy as she waited in terror, her eyes open wide in fear. “EEEEEHHH.” It hurt when it moved inside her, the pirate quickly removing the glass tube from her pussy, her lips clenched tightly together. She held her body still as she felt the large lump inside her. “EEEEEHHH,” she screamed in pain as it felt like her insides were being cut by tiny knifes. She felt it moving inside her, her body jerking around, anything to escape. She was breathing heavily now, panic setting in as it began to nibble on her insides, sharp pains from deep inside her.

The Captain purposely left only her legs tied tightly, her arms allowed her body to jerk around, the cockroach inside her making her body shake and jerk uncontrollably. He could almost feel it inside her, his hard cock only separated by a thin layer of skin between them. Her uncontrollable spasms and clenching of her muscles began, finding it hard to pull his cock in and out her slick asshole. He began to fuck her, taking long, deep strokes inside her, knowing that it was only driving the cockroach into a frenzy, the Princess dancing beneath him. He made her asshole take the full measure of his cock, her anal ring clinging to his shaft as he began to pick up speed.

Her insides felt as they were being torn to pieces, the cockroach’s legs piercing her most delicate lining, his bites excruciating, the thought of the ugly creature inside her almost driving her insane. Her body thrashed about, her asshole clenching on the thick cock that pierced her so deep she thought it would come out the other end, his pounding inside her driving the cockroach to move about. “STOP! Please take it out! I’ll do anything you want!” She begged, tears running down her face as she suffered the terrible onslaught.

“Next time you will think differently about defying my pleasure. Make me cum in your asshole and I will pull the cockroach from your pussy. Squeeze me and make me cum.” He felt the rhythmic clenching of the muscles in her tight ass. He continue to plunder her with his cock, driving his cock in and out and as he sought the pleasure that her virgin asshole would give him. It almost felt she would tear the skin off of his cock, her asshole so tight. He pulled her ass up higher, driving his cock deeper into her, burying his cockhead into the hot depths of her bowels.

She thought it would never end, her pussy clawed and chewed raw by the cockroach, her body shaking uncontrollably as the Captain reamed her out, Stefani forced to clench on and off of his cock with her asshole. “Hurry, please hurry,” she begged him. Anything to stop it!

He pulled his cock out until only her rectum gripped it in an almost death grip, shoving hard with his hips to bury his cock deep inside her, fighting her strong muscles that clenched on his thick shaft. He heard her squeal, his cock buried deep inside her. He began to cum, his balls finally releasing a hot load of cum deep inside her.

She felt him cum, feeling the hot cum bath her insides, the salty fluids making her abraded insides burn. It felt as though he was dumping gallons of semen inside her, another load shooting out his jerking head, her muscles tightly grasping the thick cock inside her, doing anything to end the painful sodomy. He dragged his cock half way out, then plunged back in again, another load of cum inside her, her stomach feeling as if it were swelling from the abundant crème that bathed her insides. Five times he came inside her, Stefani working hard to please him, to end this misery. Finally he pulled his cock out of her asshole, her anus burning as it began to close. “Take it out of me! Hurry!”

The pirate placed the glass tube inside her pussy again, this time a tiny bit of raw meat placed in the end of the tube, meat coated with a special ingredient that would draw the cockroach out of his moist nest and back into the tube.

“Thank you!” She felt the tube pulling out of her pussy, both of her holes now empty for the first time. They released her from the railing, Stefani barely able to stand.

“Let her bathe and take her to me room. I will see how cooperative she is now.”

She had managed to bathe her body, the warm water a welcome relief, especially for her pussy and asshole, both of them abused by the Captain. She was led back to his cabin, the Captain waiting patiently for her.

“Take off your clothes.” She didn’t hesitate, quickly stripping naked, spreading her legs slightly, her dark bush still wet from the shower. “Turn around and spread your cheeks for me. Show me that lovely asshole.”

Stefani moved quickly, turning her back to him, spreading her legs wider, two hands moving back to part her cheeks, feeling her anus stretch as she obeyed him submissively.

Her asshole was red and swollen from the sodomy. “On the bed Princess. I want to fuck you again.”

She didn’t hesitate, laying down on her back, bringing her legs up, parting her legs, anything to accommodate him.

“No. On your stomach. Legs spread wide. Put a pillow under your hips to raise your ass up.”

“Please not there again. I’m too sore. Take me in my pussy.”

“No. I want your hot, tight asshole again. You will either give me the pleasure I want or I will get the cockroach again. Maybe this time up your asshole. Can you imagine it crawling deep inside your bowels? So deep we might not be able to get him out. He would live at least a month inside you, nibbling at your insides, driving you insane.”

She flipped over, a pillow thrown under her hips, her ass arching up submissively, her legs thrown wide apart. “Take me in my ass Captain. I will give your cock great pleasure.”

He climbed on her, hearing her grunt as he took his greased cock and pushed it unceremoniously up her asshole. As soon as the head of his cock was in her rectum, he felt it. Her insides massaged his cock, the Princess tightening her asshole as he began to sodomize her, her grunts of pain only increasing his pleasure.

She didn’t even mind when he came inside her, another load of cum added to the previous one.

The final days of the voyage saw the pirates and the Captain taking the girls almost non-stop, the slave market would force them apart. Even the girls seemed to relish their roles, many of them having orgasms as they were taking. Even the Princess found herself cumming on the end of the Captains hard cock, humiliated when he came inside her asshole, his fingers finding her clit and driving her to an orgasm that shook her body.

10

The Slave Auction

The crowds had gathered on the dock before the boat had even landed, the word spread quickly through the town. Captain James had taken a Spanish vessel and part of his bounty was nine girls from Spain and one of them was said to be a Princess. The slave auction was already preparing for tomorrow, the auctioneer already counting his money in expectation of a lucrative day. It wasn’t often that royalty was offered for sale. The bidding would be intense, many men wanting such unusual beauties. Some would have them for their own, while others would sell the girls bodies to those that would handsomely for a few hours of pleasure with them. And then there was some that wanted them for perverse pleasures, the joy of whipping a Spanish Princess, their cocks hardened by her screams of pain, tortured for their pleasure.