A Privateer's Good Fortune

by realoldbill

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Ma/ft, Rape, Historical, Rough, Orgy, .

Desc: Sex Story: During the Civil War, some unfortunate females fall into despicable hands

It was like a curtain going up in a dark theater when the squall rumbled on southward and revealed a two-masted side-wheeler flying the stars and stripes. We closed quickly, hailed her after a shot across her prow, and she luffed her sails and stopped her engine. We lay alongside and I boarded her with a couple of my foulest-looking men. I met the startled captain, told him I was making his fine bark a prize and asked him to get his people off. He said he had some passengers and they soon were on deck looking unhappy. I sent the men to the boats and smiled at the six women, obviously two pairs with their maids. I gave the black girls to the captain and told him he could free them when he got ashore. He smiled and shook my hand.

That left me with two very unhappy women and their lovely young daughters, all four dressed as if for party, crinoline and lace, rich and haughty and very nearly bare-chested. My men got them to over my ship as my prize crew boarded. My boys were anxious and nearly drooling with anticipation as they rowed hard and ignored the show of tears. We had enjoyed a few female captives before, worn them out and, I fear, fed them to the fishes.

An hour later, with my handsome prize almost out of sight, one that would make me a good bit richer, I met with the four women on the quarterdeck. They were still unhappy that I had sent their maids away. Most unseemly I was told.

They were Amanda Fortune, a handsome matron of perhaps thirty-five years, and her snooty daughter Jane, who was sixteen and, we were told, engaged to be wed, and Mrs. Robert Thompson, a lovely who would not tell me her name, and her young daughter, Ramona, a budding beauty of with a fine body and a haughty attitude. I silently planned to be her first, second and third lover and to make her scream for more. Virgins were my absolute favorite as well as a kind of specialty.

The women had been visiting relatives in Cuba, sugar cane relatives they said, and were on their way back home, to Wilmington, N.C., despite the ongoing blockade. They demanded to be let go at once since they were southerners and knew we were as much rebels as they were even though they had been traveling on a Yankee ship. They could not believe we would take advantage of their situation. One even used the word “chivalry.” I choked back a laugh as I scratched my balls, deciding what order I would take them in and thinking about positions and restraints.

I ignored their entreaties and introduced Buck as my first mate and gave him his choice. He licked his lips and took the ripening Jane, bent her arm in her back, tore open her frilly shirtwaist and thanked me as he pawed an upright bubbie and pinched her dark nipple. “When you’re done, bring her up her and tie her to the rail so the men can use her. Make sure you get that damned corset off her.” Her mother screamed as he took her away, a plump young breast in his hand, and I thought she might faint.

Buck dragged 16-year-old Jane off to her terrible fate, kicking her feet and bawling, his big hand grasping her butt. I could see he was already aroused. The girl was in for a most-instructive hour. Old Buck was tireless as well as really big in the male tool department, long and hard as a belaying pin. He was also merciless, unfortunately for the youngster. I don’t think he really hated women, but he seemed to believe they only had one use.

My other two officers were on the prize and headed for a friendly port so I gave my quartermaster his choice, and he took young Mrs. Thompson, and I charged him to learn her name and free her from her stays. I always hated corsets although I must admit that I have horsed a few whores who wore them. Jim was a big man, and I knew he was rough on women. She was in for a busy time and her tears had already begun flowing as her hurried her along with his big hand tangled in her long hair.

I let my two midshipmen, randy boys of fifteen or so, have the other woman, Amanda, and told them to enjoy her and then put her on the rail in just her shift. They smiled and promised, saying it might take a while.

“No hurry,” I told them. “I will be quite busy.”

That left me with the luscious, young Ramona who stood before me quite bravely, chin raised, eyes wet, lower lip trembling. She was, I am sure, as luscious a nubile female as I had ever seen and my male member was getting longer and harder by the second.

“You a virgin?” I asked her as I unlaced her low-cut and lace-filled bodice, spreading it slowly open to reveal her hidden treasures in their silken embrace. Her fine young breasts were no bigger than my fist but lovely and rose-bud tipped.

She just blinked at me.

“You always wear a corset?” I asked as I stripped her to the waist and stuffed her fancy dress-top into the rigging. She was maturing nicely and soon would be full-grown I was sure although her pair of globes were now only apple sized. I bobbled them and grinned at her as she writhed and sniffed, on the verge of tears.

She nodded and I turned her about, took out my gigging blade and cut her strings. I peeled off her little waist-cincher and tossed it to the waves. “Doesn’t that feel better?” I whispered to her as I palmed a plump breast and pawed at her groin. She whimpered and wriggled.

A scream from below told me that bride-to-be Jane had lost her maidenhead if she still had one and was well on her way to useful womanhood. Old Buck was well-hung and very patient. I was sure he would use and abuse every hole she had and probably more than once. He often left them bleeding and begging. Most New Orleans whores refused to serve him.

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Story tagged with:
Ma/Fa / Ma/ft / Rape / Historical / Rough / Orgy /