Mary O’donnell and the Pirates
Copyright© 2025 by Techman1952
Chapter 1
Historical Sex Story: Chapter 1 - This is the story of Mary O’Donnell, a story of survival against terrible odds. Using her wits and her ability to adapt, to do whatever it takes to survive, she overcomes obstacles and triumphs over adversity.
Caution: This Historical Sex Story contains strong sexual content, including Ma/Fa Fa/Fa ft/ft Fa/ft Mult Consensual Lesbian BiSexual Heterosexual Fiction Historical School Incest Mother Sister Daughter Cousins Niece Aunt Group Sex Anal Sex Analingus Fisting Oral Sex Squirting Nudism
Mary O’Donnell was not born into great wealth, her father had been an Irish rebel who had been one of the men in the Irish Army that had captured Kilkenny in 1647. They had been led by Owen Roe O’Neill, her father Fergal, was a Captain in the Confederate Army, after their defeat in 1649, he took his family and fled Ireland and went to Spain. There he served in the Spanish Army, also as a Captain. And it was there that Mary was born in Torrent, Spain in 1655. She was the youngest of four girls and two boys.
Mary grew up as all young girls and boys do. She grew into a tall, willowy girl with “A” cup breasts, slim hips, red hair and green eyes. She was very smart and had mastered her lessons by the time she was sixteen. She had a gift for languages and knew Spanish, French, English, Latin, Yiddish, and Romani. At that time women weren’t allowed to advance into higher learning, she couldn’t go to a University. So she was given a job teaching the children of the governor of Cuba. The children, three girls and four boys were between the ages of five and fifteen.
Arrangements were made for her to travel to Cuba with a twenty year old HandMaiden to act as a Chaperone, companion, and she would help to dress Mary, help apply makeup and do her hair. Her name is Gillian Fitzpatrick standing at five feet three inches tall, slim build, “B” cup breasts, red hair and green eyes. The two women got along very well. Unknown to Mary’s mother and father, Gillian would supply a portion of Mary’s education that was lacking due to her cloistered life in the care of priests and Nuns. It was her sexual education. Other than her brothers, she had never been around boys much at all. Gillian was a lesbian and had previously had experience with girls. Experiences she was more than willing to pass on to Mary.
The ship her parents had booked passage on the Spanish flagged ship the Midnight Princess. A Merchant vessel, lightly armed and Captained by a portly gentleman Ernesto Cavella. They left Valencia on the morning tide of January 5,1672 for Havana, Cuba, a voyage scheduled to take two months. The women were the only passengers and the only women on board the vessel. The Captain limited their exposure to the crew by only letting them on deck in the early evening for one hour between 4:00 and 5:00 just before sunset. The rest of the time they were to stay in his cabin, which of course he had given them while he took the first officer’s cabin for the voyage.
The girls spent most days in quiet conversations, reading, and studying together. At night they were forced by the fact there was only one bed, to sleep together. It was there that they began to have their most interesting conversations.
Gillian was more worldly, she had been born in Ireland, her first job had been as a tutor of a precocious fourteen year old girl who had already figured out that sex was fun with other girls. Gillian had been an easy target, seduced over several weeks. A touch here or there, a kiss for thanks that lingered longer and longer, eventually her tongue penetrating Gillian’s lips into her mouth. Gillian didn’t understand the feelings that she felt, a tingling sensation began between her legs, a place her mother and the Nuns had told her to never touch except to clean. Then the girl began to touch as well as kissing, her ears, behind her ears, then down her neck. Taking several days, but seeing signs that the brick wall around Gillian sexuality was beginning to erode. The fingers traveled down her neck, onto her chest, stopping short of touching any part of her breasts. Then after three weeks the girl touched Gillian’s inner portion of an ankle, still while kissing. The hand gradually moved further up the inside of her dress, along both legs. Gillian discovered that there was a connection between her thigh, just inside and above her knee, directly to her nipples and her secret place between her legs. A slippery wetness was developing between the lips of her secret place! For the very first time in her life, she fought the urge to disobey her mother and touch the forbidden place, to willingly commit a sin. But still she resisted!
The next day, the girl upped the ante by moving her hand up “Gillian’s inner thigh almost to her final goal. The kiss intensified, fingernails
lightly raked from her crotch down almost to her knees and back. Gillian moaned deeply and her legs spread invitingly. Her hips raised in an attempt to get the girl’s hand to touch her forbidden spot. But still the girl did not pursue things further.
The next opportunity came the next night, once again starting with kissing, then caressing, moaning encouraging the explorations, Gillian’s fingers for the very first time drifted into her loose fitting bodice and brushed the erect and hardened nipple sitting on the top of her small breast. Then the fingers moved back toward the nipple again, only this time they stopped. The nipple was caught between the girl’s thumb and first finger! They pinched and pulled on her nipple, the little bit of pain was sending pulses of energy straight to her forbidden spot, moisture collected as her nether lips engorged as excitement in the feelings generated by the pinching fingers caused them to extend from their normally hidden existence to highly visible manifestations of the excitement she was feeling. A feeling she realized that she had lived without for a long time. Longing for more, Gillian sought to continue this rapturous feeling by returning those feelings to her student. She moved her hand to the girl’s breast finding an already turgid nipple on her slightly smaller breast. She mimicked the girls pinching and received much the same response.
The girl’s fingers left her breasts, moving to her knee then lifting the yards of cloth out of the way, delved down between her legs straight to her juicy center gathering up the wetness and spreading it over the nubin at the very top of the now swampy slit. Rubbing down and gathering more juice then spreading it around and over the erected clit sending even more and stronger impulses of absolute pleasure to her real pleasure center! Her brain!
Gillia had tried to follow the example being set by the girl, but suddenly her soul, and she was very certain it was her soul, exploded sending her body into convulsive gyrations as her vocal cords released an unbidden scream only just squelched by the mouth of the girl.
The girl’s mother, who had waited outside the door for two weeks waiting for such an occurrence, burst into the room to bear witness of the fornicator’s perverse attack on her innocent daughter. The same daughter she had been satisfying the enflambed desires of, for several years. Proud of her daughter’s work at getting her beautiful tutor into this compromising moment, not to blackmail or enslave, but to entice into a love triangle with the incestuous mother and daughter.
Embarrassed and aghast the tutor started to explain, when the mothers lust got the better of her and plunged her face into the source of the intoxicating and titillating smells emanating from the swamp between the girl’s legs. The mother licked and sucked the beautiful kitty displayed before her. The daughter, recognizing that their plan had fallen apart, promptly sat on the tutor’s face. Not only muffling the sounds but blocking the airway of her victim. Rubbing her quim across the tutor’s mouth and nose allowed the girl to gasp in brief pockets of desperately needed air. Finally having enough air she began to enjoy the ministrations of the mother and the sweet taste of the daughter, deciding more of the taste was warranted, she stuck her tongue deep into the love hole of the younger girl. The depravity of that act coupled with the mothers use of her tongue caused Gillian to once again explode in ecstasy! The younger girl also experienced the “la petite mort”, the little death. But she just quietly passed out from the exquisite feeling brought to her by her beautiful teacher.
Now given this opportunity to teach Mary, Gillian began the same program to conquer the same ingrained Catholic teachings she herself had held. Slowly, patiently, Gillian brought Mary ever closer to having an orgasm. It actually took less time than it had taken her first student to convert her to the Sapphic arts! In just six days and nights Mary was spreading her thighs open so Gillian’s head could fit between them down all the way to their junction, fingers parting Mary’s generous pussy lips while Gillian’s tongue took liberties never granted to anyone else in Mary’s seventeen years of life, soon Mary had yearned for Gillian taste on her own tongue and had shifted around so both of them could enjoy the nectar of the other at the same time. Gillian had no idea that this was not the first time Mary had been sexually involved with a woman, she was quite experienced in fact. Gillian did wonder about the small rose tattoo, but assuming it was a birthmark didn’t really look at it closely.
From that moment on, the two women made love with abandon, stopping only to consume food to give them the energy to consume each other. Often they didn’t dress for days at a time.
In the middle of the eighth week from the port of Valencia, the routine changed in a terrible way. Shouts of alarm penetrated the thick wooden timbers of their chamber. Pirates were approaching from the southeast under full sail and would overtake the Midnight Princess within the hour! The crew of the Princess hoisted more sail and made ready the paltry ten eight pounder cannon five per side of the carrack designed ship that was almost seventy five years old. The first Mate had used the spyglass to see what they were up against, it was a former Spanish Galleon with twenty eighteen pounders per side and almost twice the sail area.
There was little hope that they wouldn’t be caught, even less hope that they could successfully manage to sink or damage the pirate ship enough to get away. As far as defending the ship from a boarding party, they could expect forty or more men swarming over the gunnels against the twenty men of the Princess. The best they could hope for was that the pirate Captain would take the cargo and leave the crew and officers alive with the ship. The odds of that outcome would be better if they didn’t fight at all and just surrendered. But if the pirate Captain wanted, they would all be executed by being put to the sword, hanging, or walking the plank and there would be no way at that point to defend themselves.
Captain Cavella thought about the options, that they would be caught was certain barring a Miracle. They would die if they fought them, the only possible chance was to beg for mercy after surrendering the ship. At the moment of his decision he wasn’t thinking of his human cargo, he was only thinking about his own life. It wasn’t until after he ordered the sails brought in, all the cannon fired, and a white flag flown in place of the Spanish flag, that he remembered the two beautiful girls in his cabin.
Rumors of pirate treatment of captured women varied from them being raped by the entire crew, to being sold as slaves to brothels or rich plantation owners. Virgins brought a much higher price so they were left alone until they were sold. But every Captain, especially Pirate Captains, ruled at the whim of the officers and crew of the ship that they Captained. If the Captain did something to destroy their trust, or make a decision that was contrary to the wishes of their crew he could be replaced, often permanently! So what would ultimately happen to the two girls would probably come down to just how horney the pirate crew was!
The Captain went down to his stateroom and knocked on the door. He heard the key turn in the lock after he announced himself. Stepping into the room he addressed the two women,
“Ladies, I fear we are about to be boarded by pirates! I have already surrendered the ship to them and hope for them to show mercy to me and my crew! The two of you are basically cargo, and as such you will be subject to whatever indignities they wish to inflict on your persons. At best they will sell you as slaves at Port Royal, Jamaica. Pardon my saying so but circumstances demand I speak plainly and honestly, if you are virgins the price would be much higher for you. If they choose to sell you, they would leave you alone sexually. If not, I think you can imagine better than I, at what might happen! I’m leaving you two pistols, and two knives. If I were you I would place the pistol against the chest of your partner and then at the same time pull both triggers. This will prevent eternal damnation by not taking your own lives, but by the expediency of taking each other’s lives. I caution you not to wait too long, they will be boarding us very soon! Good luck and goodbye”
Mary and Gillian looked at each other, then at the weapons the Captain had placed on a table. Their eyes were wide at the realization of the finality of the choice they were about to make! They loved one another, but could they kill each other? Mary was a virgin, but Gillian was not, though she had never been with a man, she had lost her maidenhead to an ivory phallus inserted in the heat of passion by her student’s mother when she was eighteen years old. No man had ever had her and she would rather die than have one, much less let the entire crew of pirate galleon fuck her to death. Mary wanted to take her chances, maybe God would provide a way out! She certainly understood Gillian’s fears! Did she love her enough to pull the trigger?
The boat rocked as the pirate ship was made fast against the port side of the Midnight Princess, the sounds of many feet jumping onto her deck punctuated the need to do whatever must be done now. Waiting was not an option!
They kissed one last time, both professed their love to each other, then Mary placed the end of the barrel against her lover’s chest directly over her heart, Gillian smiled and nodded. Doing the act was undoubtedly the hardest thing Mary had ever done in her short life, but she pulled the trigger! The explosion and flash of the gunpowder in the pan, along with the smoke, shielded Mary from the momentary look of pain that crossed Gillian’s face, by the time the smoke had cleared she had a look of serenity there instead.
Mary quickly locked the door and pushed the table against it. Then she gathered several of the bricks under the brazier that was in the room, placing them along with Gillian’s body in a bedsheet, then wrapping a rope around it. Mary dragged the body to the open window in the stern of the ship. Mary said a prayer and let the body fall into the sea below with the certain faith that Gillian’s soul was in the hands of God already!
Now Mary had only to face her own fate.
The door latch rattled, a muffled voice was heard,
“Open this door or it will go worse for you!”
“How can something be worse than being violently raped by pirates, perhaps repeatedly?” Mary replied.
“I am Captain Jack Hood of the privateer Sprite, I guarantee that you will not be raped! Will you come out now?”
“To what end Captain Hood? I come out and I am not raped but I am sold to a brothel or my virginity is sold to a plantation owner. Perhaps I should have joined my friend in choosing death!”
“No one wants you dead my Lady! You must have choosen life in spite of the likelihood of being raped so you have already made your decision! Now you just have to face the results of that decision. Unlock the door and let us in. If not, we will come in anyway, and like I said earlier it will go worse for you!”
In answer Mary aimed the musket at the center of the door and fired! The ball penetrated the thick door and the now flattened lead ball hit Captain Hood in the middle of his forehead. The lead was hot but almost all of the energy had been expended on the door. Not to say that it didn’t hurt him, it burned him more than anything. It also enraged him!
He was through talking to the bitch, now she would submit or die! And at the moment he was leaning more towards the latter! He and his First Mate Evan Fuller hit the door together breaking the lock and pushing the table back over a foot. They hit it again and pushed the table completely out of the way, allowing them to charge into the room. But they were both brought to a stop by the vision in front of them.
Mary stood before them with both hands on her hips and green fire in her eyes! Her red hair splayed out from her head like a halo giving her the appearance of an avenging angel, a very beautiful avenging angel!
Mary was surprised by the dramatic entry by the two big and handsome men. Captain Jack was a big man, six feet three inches tall, two hundred pounds, black hair, and almost black eyes. Mr. Fuller was five feet ten inches, blonde hair, dark blue eyes, one hundred eighty five pounds. She had never seen such handsome men! The fight left her as she processed the dichotomy represented by two beautiful men as savage pirates!
The two men slowly approached the beautiful woman, and saw the fire in her eyes fade to acceptance of her fate. They stopped three feet in front of her. Captain Jack, using his formidable command voice told Mary,
“Strip! Take off all of your clothes now! If you do not begin immediately Mr. Fuller and myself will do it for you, and we won’t spare your clothing! We will rip them from your body and you will not have anything to wear if we decide to let you dress again at some point. Which is it going to be?”
Recognizing the resolve in the man’s voice and knowing she had no alternative, Mary began to undo what she could reach, but she couldn’t undo the eyelets that held the back of her dress together. She turned around, presenting her problem to the two men. They both reached out to help her but ended up taking turns.
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