Captain Rodolfo’s Cabin-Boy

Captain Rodolfo’s Cabin-Boy

By Jessica C

A boy in the new world, becomes a pirate, but one with new makings...
The cabin boy will not be an ordinary pirate...
but one who can please women more with his gentle ways...
Roberto is in danger of becoming Roberta

“Roberto” my mother is calling me. “This is Captain Rodolfo. You are going to serve him on his magnificent ship. You'll do whatever he says; do not disgrace our family by being disobedient. This is why I taught you to be more like your sisters. You and Luis are twins, but he seems to have both his and your portion of strength and size.” It is true, Luis is taller and already rugged, the size of a man. I am small but feisty.

Mama met Rodolfo last year and promised that I would learn to cook, sew, clean and be obedient. She has done a very good job, and it is now time for me to go with the Captain. His ship is not in the harbor at St. Augustine like most ships, but farther south in an inlet near where we live. Nor is his ship a grand Spanish galleon.

Rodolfo talks to me as we go to his ship, "Roberto, you are young and delicate for a boy. You will need to be careful around the men. You will need to get used to how we speak and that we are rough and crude. I want you to be my cabin boy and I do not want you becoming like them."

Rodolfo's ship is an old and battered ship, with a crew of cut-throats. Half of the crew were drunk when they were brought into Captain Rodolfo’s service. But soon they had taken part as pirates in boarding several ships, robbing modest treasures, and the sinking of both British and Spanish ships. They have become wanted pirates, too.

I am on-board when we trick another ship, The Maverick, to thinking we’re dead the water with troubles and slowly sinking.

Their captain makes the mistake of coming on board to personally inspect our problems down below. That is before taking over our ship. What awaited him below were swords and leg-irons. His crew gave up with few shots and three of their men dead.

The British had sent the Maverick to attack Spanish ships bringing back gold from the new world. Their captain had hoped to take our ship to help carry out his orders. The Maverick had all the tell-tale signs of being a merchant ship to deceive ships and ports where it might land. It had a cargo of clothing, cloth, spices, rum and trinkets that they could sell or trade. They would even make port and trade their goods to gain valuable information.

It was humbling for me on a pirate’s ship doing the sewing clothes; taking blouses and making them shirts befitting pirates. Men who did not know the difference between satin and wool. Nor that torn pants showing their manhood were not decent.


We were nine days sailing the Maverick when Rodolfo finds maps showing the Spanish sea lanes for ships to and from Spain. It even has drawings and information on many of its ships. The Captain laughs when he reads of a smaller galleon called The Primrose captained by the Baronesa Marietta Diego. Her loads of gold were sizable yet not as great as others. But in three journeys she had never been boarded or lost her cargo. Her small galleon is still better than the Maverick.

Rodolfo set his course for the sea lanes, sitting his ships off the coast of the Caribbean islands. He buried gold from two ships he was able to sink. They were both overloaded and slow in the water. They carried not only gold and silver but turquoise and other precious gems. I have since taken to fashioning jewelry as well.

By now my shirts button differently from the others, and the men think I smell like a woman. The biggest difference is that I do not stink like them. I wash my whole body two times a week as the captain has requested. He has even had me make pants for myself from brightly colored skirts, from the Maverick's cargo. I have in truth become fond of wearing them. I find myself sometimes uncomfortable around Rodolfo and the men.

I have developed one problem and that is taking a fancy to jewelry and women’s fashions. The truth is I am now welcomed into more women’s boudoirs than any of the crew when we make port, even Captain Rodolfo. From barmaids to the lonely wives of sailors, soldiers and merchants often left alone and neglected on these Caribbean islands. I get to fashion and personally fit them in their finer clothing.

One thing that is included with serving these women is an additional bath. They do not like me to smell like a sailor of a ship especially a fishing ship. A bonus is to learn how to please women without putting them in danger of bearing a child. Between using my fingers and lips I can bring many smiles to their faces and fun living in hard places for women.

I enjoy learning to please them, which on occasions has them being affectionate with me. They tend to treat me more like another woman than a cabin boy. My hair has grown longer and they have taught me to keep it clean and well combed.


It is funny to me that Rodolfo had started as a fishing captain and had taught his sailors to fish, even on the Maverick. It has kept our ships with fresh food while at sea, but it also added to the stench of our new pirate ship.

Due to my small stature, some women have taken to having me wear some of their clothing as I sew and fit new dresses for them. It has helped with Rodolfo being seen in a better light in some ports. Some prestigious women have hidden me as another woman among them. We now have three ports where we are openly welcome. The cost to Rodolfo is giving me up days at a time to help unattended women like the Alcalde’s wife, the wife or woman of a ship's captain and other women of society.

I have taken to wearing bloomers even on the ship and have learned the finer ways of women in making themselves more beautiful. If need be I can help them dress, choose jewelry and do their makeup. Time has passed and whether I’m with other women or not such things please me more.

The Primrose was spotted a month before coming back to the new world. We even made port, where she took on fresh water and food for the last part of her voyage. I had seen her and I was even introduced to the Baronesa Diego. I was serving the Lady Rodriquez the day she prepared luncheon for the Baronesa Diego. I had helped serve. After the servants dressed me as another girl and I’m introduced as Roberta.

Rodolfo had tried to catch her ship the year before but she had passed by too quickly, and once sailing by and we could not catch her.

The Maverick has since added sails as well as cannons on both sides of the ship.

This time, we hide on the eastern side of an island that is near an anticipated route of the Primrose. It is part of the information I had secured while serving the previous luncheon. I learned other information that would serve me well.


It is a sunny day in early September when the flag of the Primrose is seen on the western horizon. There we are among the smallest of islands with the largest of boulders protruding into the sea. It hides the Maverick until the Primrose draws closer. Rodolfo is pleased with himself. He even has visions of capturing the Primrose and taking her as his own ship. A pirate captain with two good ships would be a feather in his hat and bring respect among pirates.

I have taken to wearing a satin top that could become a dress if and when I lose my pants. Though that fact is not known among the other pirates. I'm hoping that Baronesa Diego will recognize my shoes given to me by Lady Rodriquez when I served her. I had even altered a blouse of hers with which she looked most beautiful.

I had warned Captain Rodolfo that "The Baronesa had said, she would have a surprise of her own on the return voyage, but he laughed at me as he did much too often.

The Maverick now has a reward price for anyone who captures or sinks the ship. Since Baronesa Marietta Diego has already seen her in port; she will know our ship on sight.

I did not know all of what her surprises might be. She is to be bringing an attachment of soldiers and sailors who are returning to Spain. Captain Marietta is hoping to capture Rodolfo and the Maverick if she is attacked. She even secured cannons that could fire the cannon balls a farther distance than normal cannons.

When the Maverick sails out to intercept the Primrose, Captain Rodolfo is surprised that the Primrose keeps sailing our way. It makes the intercepting point come sooner then he’s prepared for. Captain Rodolfo laughs at the first of her cannons being fired by the Primrose at a distance that appears to be too far away. The Primrose's Captain has a plan that Rodolfo has not yet figured out. While the first shots do miss, they now have the range and a better measure for their next shots. The third and fourth cannonballs hit the ship. One hits the starboard side of our ship and the next cannonball hits the front deck sending the deck crew scurrying for cover.

Our sailors begin to panic, firing our first round too early. It will take valuable time to reload. The Maverick is already taking more hits from the Primrose. With three cannons blown out commission on the broadside toward the Primrose, we are vulnerable. The Primrose now shoots its lesser guns and one mast is greatly damaged and in danger of falling.

Their soldiers are marksmen and their extra sailors become visible only as they approach to come alongside and board us. Captain Rodolfo has scared his crew, “You better fight to the finish, lest we all hang from Spanish gallows!”

I have handed six sailors fancy dresses to change into. Their pretending to be women will fool no one, but it lessens the fighting force by their number and then three more sailors come seeking to copy them.

I have since taken to hiding under stairs until the ship is seized. Once boarded, I am found in my dress with my hair pinned up in curls, by one of their officers and sailors. This is a time when having no manly whiskers is very helpful. He asks, "Young woman, it is strange to find a woman aboard such a ship. Hurry and explain yourself."

Taken aboard the Primrose to the Baronesa Marietta, the Baronesa laughs under her breath as she sees me. “O Roberta, I am pleased to see you unharmed. Is it true you outfitted some of the Maverick's sailors with dresses?”

“It is saving you from the judgment that the others are facing, at least for now. But you will need to cooperate as well as to continue as Roberta. Instead of death or prison, you will only lose your extra leg and its baggage.”

I seek to bargain instead, “You know there is another island your ship could port and you can claim the island for Spain.” The Island she later names Lucia so claimed and named for Marietta’s mother. Only later does it carry the name of Saint Lucia for whom both her mother and a sister are named. The Maverick under Marietta is renamed the Lucianna.


The first night I stay aboard the Primrose is with the Baronesa in shackles. I have a new purpose. The Diegos have not had a boy born to their family, and Prince Miguel of their region in Spain is believed to shoot blanks. Marietta believes if she could conceive a son and claim Miguel to be the father. She could win his heart and become a princess.

While she likes sailing; being royalty and living as such would entice her to leave her present calling.

My manhood increases in strength as it gets exercise every other day. We have made the coast of Africa, and are sailing north as I begin more earnestly to sleep with her at night. I walk the decks of the ship as Roberta by day. I am taken as being the Baroness's lady in waiting. Her close servant Maria knows my identity and claims my roles are her idea.

I enjoy being seen as a woman as well as making love with Baronesa Marietta. Though we have intercourse, Captain Marietta has schooled me in making love as another woman.

Captain Marietta greets seeing the Rock of Gibraltar by being sick and heaving over the side rails with morning sickness. Though sailors do not recognize it as such. Upon landing days later with another bountiful treasure, and the former Maverick; it brings great honor to the Baronesa. Getting to the family homestead, one role for me is done.

The Baronesa is rewarded with an extra chest of silver coins for bringing back the Maverick. Sisters Luciana and Valeria joyously receive their sister back. And word had already been sent to have Prince Miguel quickly come courting her at their home.


Maria did a quick study on the procedure I needed. It is on the eve of a harvest festival that I lose myself to womanhood. It will be nearer the end of the year before I am dancing. I am schooled by Luciana as a woman. It includes not only learning feminine ways, but I am schooled in the arts and literature. Truly Roberto is gone and Roberta is alive and well.

A week later I am fashioning a silk wedding gown for Marietta. Morning sickness has passed but it will serve Marietta well as she fakes morning sickness after her marriage to the Prince.

After Marietta's wedding, Maria has gone to live with Miguel and Marietta. I stay at the Diego’s for when Marietta comes back to visit.

It is May that Princess Marietta comes to her family's old but grande hacienda and waits for the birth of her child. I am eager to see her and help the birth of our child. I have taken instruction in midwifery. Yes, there is a court doctor, but he insists that Marietta give birth to her child during the day. No, he is not ignorant, but egotistical and lazy.

I am given to sleeping in the corner of Marietta’s room. Each night I heap her with praise, massage sore muscles and pamper her as much as I can. I rejoice in the glow that has come over her. She delights that I have sewn two gowns for the baby, one smaller and one larger. Miguel is hoping for a boy to be his son and an heir.

Marietta says, “Remember when I first saw you Roberta and you were sewing fancy dresses for the Alcalde’s wife. I began to fall in love with you even then. I loved the thought of a man as a woman. The sailors aboard my ship respected me, but that was out of fear. You, Roberta, loved me for being an accomplished woman.”

I begin to speak, but pause as I haven’t been given permission. Marietta says, “Please speak.”

I say, “You became an image that I longed to see. The woman who was known to captain the Primrose. When Rodolfo dreamed of attacking your ship. I was afraid he would hurt you. When I saw you and listened as I served you and Lady Rodriquez. I feared for us and our ship.”

“I knew Rodolfo seeing your beauty dismissed you like a sailor. ... It was then I began earnestly to dream of being a woman in your court and no longer be a cabin boy. I did not believe that it could come true.”

Princess Marietta says, “I fear you being in my court. If someone would find out you were a man and the father of this child. Worse than I love Roberta more than Miguel.”

“Miguel is a good man and I do love him, but he is weak and cannot finish what he starts.”


It is early June when Miguel comes to stay near Marietta and near the birth of their child. His mother the Queen is now living here, but she has given her a special room at the other end of the hacienda.

It is now Miguel, we are giving special instruction to. He had begun to weep having been given to drinking too much wine. He cries about his manhood and agrees to learn how to please his wife as the woman he loves.

Maria with the blessing of Marietta uses her body to teach Miguel how to please Marietta. Gaining his new skills, he relaxes and his manhood begins to strengthen as well. Maria stops giving him attention, less she becomes pregnant. Marietta orders me to begin pleasing him. We are afraid that he might lose his new powers if they are not exercised.


Thankfully the time for Marietta to give birth is upon us. It is near midnight and the doctor is away; not to be found until morning. Maria and I are called to help Marietta birth her son. It takes three hours and it is indeed the male child that is wanted. The bells of the hacienda as well as nearby church ring loud and clear.

Marietta wants to sit up and nurse her baby but I listen to her body, as she still has pains. New contractions have begun. I indeed had heard the beating of another heart. Maria had delivered the newborn prince and carefully watches over him.

I am to deliver a second child. I have Marietta clean and ready. I coach the Queen Mother to massage the pained shoulders of Marietta and to wipe her head and face. Others glare at me for using the Queen in such a way as a common servant. But she is delighted to help, for her it is a joy. The contractions grow in size and closer together; Maria seeks to hand the first baby to the Queen.

Marietta and her mother-in-law are bonding. It is her mother Lucia who takes to holding the first baby. The second baby crowns at the opening of the womb. “Push Marietta,” and she does as I ask her. The head appears but I see the cord around the baby’s neck. I have heard of it and know it is not good. We are thankful for my small but strong hands. One hand slips between the cord and the neck; Marietta cannot help but push and it causes her great pain. The shoulders are out when I tie both parts of the tube and snip in between. A baby girl slips out with the next push. Little Marietta appears to be petite next to the baby boy.

It is a while before the afterbirth of babies exit her body and I massage her to help stop the flow of bleeding. Marietta is able to get both babies to nurse and receive the first nutrients from her breasts.

The Queen had brought a wet nurse from Madrid, but she and Marietta are taken with the beauty of the mother nursing her babies. Queen Camilla is the first to proclaim: "Miss Roberta will be in charge of watching both children in the nursery!"

She says, “We could have lost the second baby and the mother from complications. You will come back with us to the castle." She whispers to Marietta and me, "I know you have helped to strengthen Miguel’s strength. We are pleased he was able to father this child. Another child will take away any talk.”

Marietta gains her strength back beginning the next day and is amused as there are no twins on the side of either family. Twins in my family usually skip a generation or two. Fortunately, Marietta’s image is strongly upon each child.

I think back to when I was a scrawny boy in a peasant's house and given to a pirate to become a cabin boy. I am now heading to Madrid as a woman to care for two babies in a castle.


Miguel names the boy on the eighth day, Joseph Miguel for his father and himself. He names the girl Marietta Camille Luciana for his wife and their two mothers. He is a joyous and a good father. Miguel never did ask Marietta and anyone how he fathered his first two children. He and Marietta have since become good lovers and she has taught him many ways to please her.

I get to raise their three children for ten years before I am given in marriage to a scholar of the court named Hosea Mateo. The scholar now serves in King Miguel’s court.

I am twenty-five before I bleed like a woman, but even then Marietta says, "It is a safe marriage for you since Hosea is more interested in his studies and research. He is thankful for you being a lady who knows the arts and society." Marietta requests as I am yet her servant, to sew a wedding gown of satin and lace. This is done with the Mother Queen's blessing.

Mateo says, "You will help me in serving within the King’s court. I am very thankful for this, but I do not know my way with women."

All that is true enough, until we are in our marriage chambers and he discovers the joy of making love with a woman. I relax over time to my being a wife. Queen Marietta and I are friends that enjoy seeing each other when I am able to attend court.

It is a year into my marriage that Queen Marietta and Queen Mother Camille come to our cottage within the castle walls. They have heard I get sick in the morning and might be with child. Marietta says, “I do not know if you have pleased or angered the angels but I have seen the light of angels hovering here during the night. It has become my prayer that you be blessed and your womb is whole. ”

I laugh, “Could you not have blessed me to sail in the Primrose once gain instead?”

She says, “You were not yet whom you are when you sailed that ship. I could have Hosea Mateo Francisco be recognized as a Barone and you as Baronesa Roberta Marietta, so they know you served your Queen with honor.”

I am pregnant four months when the swelling of my breasts begin. I cry, I have become a woman in many ways and now I will be able to nurse my child as well. I have seen the pain and anguish of childbirth. That I do worry about. Where is my mommy when I need one.


My Spanish when I was growing up in the new world was crude and I was very ignorant. The things my mother taught me the last year I was with my family, serve me well as a wife and soon as a mother. It has been Marietta who has seen to my finer education. She has raised me to be a woman of strength as well as one who is feminine and refined as a lady of her majesty's court.

The two fancy gowns that I wore to the Spanish court, now wait for a day I can wear them again. I have altered dresses to fit this expectant mother. Strange enough even this time in my life feels like a blessing. Though come my seventh month, I am waddling around and my steps take time.

Mateo and I have been invited to a private dinner given by the Queen Mother. Miguel, Marietta and their three children Joseph, young Marietta and Candelaria (Candice) Camilla Isabel. We arrive before the King and his family.

Queen Mother Camilla tells Mateo, "Tonight I am formally requesting of the King to name you Barone Mateo and Baronesa Carmela Francisco. You are already known as Mateo a scholar in science and mathematics of the King's Court. There is a new Order of Carmelites forming in Spain and among other things, I would like you, Carmela to become an emissary from the King's Court to them."

I am more impressed when Joseph, Mary, and Candice come running over to me as they enter the Queen Mother's residence. "Berta, Berta, you are huge! Momma says she hopes you are having twins!"

I stagger on my feet as the idea has not crossed my mind. I want to sit, but I need to bow to the King and Queen. Mateo and I, even as friends never dare to forget protocol. I alone with Marietta or Queen Camilla am allowed to relax as a friend.

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