Even Pirates get Spankings

I wrote this for a friend, who I sometimes affectionately refer to as the Dread Pirate Kay (or something close to that). There is a part of Kay that dreams of sailing fast, tacking against the wind, her chestnut hair blowing behind her, the sea spray in the air. Kay does not like authority much (but then, neither do I) and dreams of storming the beach for treasure. She wants to have adventures that make her late for tea. She also does not like mathematics. Like the girl in this story, my friend Kay has, on occasion, gotten a spanking for not doing her mathematics assignments.

In my imagination this story is set in the New Orleans area of a bit over two hundred years in the past. The New Orleans area was a center of piracy and smuggling in the late 1700s and early 1800. Some of these pirates and smugglers were originally from France or were refugees from the French Caribbean. Gian is one of these. In writing this story, I've thrown in a few french phrases. I took French in college. I liked French about as much as Kay like Geometry (I had a beautiful teacher's assistant for my French section, but unfortunately I never got spanked for not doing my french assignments). To those who do actually speak french, my apologies for any linguistic offenses against la langue français.

The day was warm, with a clear blue sky, but the heat and humidity of summer had not yet arrived. This was, Kay thought to herself, a day when no one should be forced to sit and study geometry. There Kay was, trying to work through the boring proofs about angles, triangles and squares. She felt like she was trying to push through warm wax. Kay was sure that it was geometry that was responsible for the fall of classical Athens. Their children had all died of boredom. The Spartans, who never had to study geometry, had just come along after geometry had done its dirty work.

Kay heard Gian's footsteps behind her. She could always tell that it was him. His step sounded like that of someone much smaller and the first time she had noticed it, she was surprised that such a large man could move with so little sound. She thought sometimes that he had cat feet.

Gian looked over Kay's shoulder at the book that she was trying to read, all line drawings and Greek letters.

"If you finish up the work that Maître Pascal has assigned, we can go out sailing if you like", Gian told Kay.

She was saved, Kay thought to herself. There would be some escape from geometry which was so boring that she felt like her brains were running out her ears.

"I'm almost done", Kay said.

"Bon. Come find me in the office when you're done."

It was not exactly true that Kay had finished most of her geometry problems. She had only done about a quarter of the problems that her tutor Monsieur Pascal had assigned. However, Kay assured herself, piling up her papers and closing her book, she could finish after they went sailing. Kay changed out of her dress into a pair of canvas breeches and a white blouse. She put her long brown hair in a braid and then went to find Gian

Gian was sitting at an old scarred oak desk, going over the accounts for his shipping business. She noticed that he had two account books out. One was the official account book, the other book recorded some of his "unofficial imports", goods that his ship smuggled had into New Orleans.

When ever Kay looked at the broad expanse of the oak desktop, she could not help thinking about the occasions when she had seen its surface up close. Kay looked over to the corner of the room. There was an old brass umbrella stand, which had a couple of walking stocks and two rattan canes in it. Kay's opportunity to examine the surface of the desk closely came when she had been bent over it, the skirt of her dress flipped up over her back as she waited to feel one of those rattan canes burn across her bare bottom.

Gian had been a childhood friend of Kay's father. When they grew up, they had become business partners in a privateer, an armed merchant ship. Kay's father had died saving his friend Gian's life. Kay had never known her mother, who had died in childbirth. Gian had raised Kay from the time she was three. Gian was utterly devoted to Kay and many people who knew them felt that he spoiled her shamelessly. What they did not know what that he could also be strict and did not hesitate to spank her when he felt that she needed it.

Kay was so happy to be freed from the cruel bonds of her geometry studies that she almost skipped as she walked beside Gian down to the docks at the port. Her boat Allure and its mast sat on wood supports at the end of the dock where Gian's ship, L'Egalite was moored.

Kay and Gian put the Allure in the water next to the dock, stepped the mast and rigged the sail with smooth familiarity. The Allure was Gian's birthday present to Kay two years ago, when she turned fourteen.

Gian boasted that in the last two years Kay had learned to sail the fast sixteen foot sailboat as well as he could. As they sailed across the bay, Kay found it a heady feeling calling out the tacks and jibs as she worked the rudder and the captain of the L'Egalite, her "crew", worked the sail.

After spending a couple of hours sailing across the bay and back Kay and Gian had unrigged the boat and put it back on the dock. Gian took Kay to one of the dock side seafood restaurants. The gaze of some of the men in the restaurant followed Kay as they walked to their table, but no one dared to make a comment about Kay's figure where the Capitan of the L'Egalite could hear it. Kay ordered scallops and tea. Gian had Redfish, with a large mug of the house brewed ale.

The next day Gian was gone down to the docks and the L'Egalite before Kay got up. After lunch Monsieur Pascal came to the house to tutor Kay in geometry. He scolded her for not finishing the problems he assigned and scolded her again when her attention wandered off.

Anne, their house keeper, made a boneless coc au vin that night for dinner. Anne served the chicken with a freshly baked baguette that had been delivered from the bakery that afternoon and steamed green beans. When Gian had adopted Kay, he had hired Anne to take care of her when he was away at sea. Anne was like family and they all ate together. After dinner Kay helped Anne clear the table and wash the dishes. As they were finishing, Gian came into the kitchen and told Kay that he wanted to talk to her when she was done.

"I wonder what that's about", Kay said.

"Monsieur Pascal left a note for Capitaine Gian, Mademoiselle. Perhaps it is about that."

Kay's heart sank. "Well, I better go find out"

She dried her hands and went to Gian's office. She was glad to see that there was a coastal map spread across its surface, not a rattan cane.

Gian looked up from the map. "Monsieur Pascal wrote me a note about your progress with your geometry studies. He says that you have not been finishing the problems he assigns. And in fact, demoiselle, I believe that some of that work was not done when we went sailing yesterday. Would that be true?"

Kay looked down at feet. "Yes, Sir", she said, softly.

Gian gestured at the account books and the map on the desk. "Someday this will be yours, Kay. If you don't want to rely on some man to sail L'Egalite, then you must be better than most men. You must know how to navigate and you must understand the structure of a ships hull. For those things, you must understand geometry."

"Yes, Sir. I meant to finish the geometry problems..."

"And you did not tell me the truth when we went sailing, did you demoiselle?"

"No, Sir"

"I am disappointed in you, Kay. You have earned yourself a whipping, demoiselle. Now get ready for bed."

"Yes, Sir", Kay said, turning to go. Now she wished that Gian had made her bend over the desk and had caned her in his office. She hated having to wait, dreading her coming spanking. Kay walked upstairs to her bedroom, shuffling her feet as if it would somehow slow down the the arrival of her punishment. A few minutes later Anne came up to help Kay out of her dress. Kay put on a white cotton chemise that was embroidered around the neckline with little blue flowers. She sat at her dresser while Anne brushed her hair. The brush was a large flat backed ebony brush that had belonged to Anne's mother. Kay loved it when Anne brushed her hair and she tried for a moment to avoid thinking about the other uses that the hair brush might be put to that evening.

When Kay's hair was shining like a sheet of silk, Anne put her hair in a braid. "Soyez bravent le chéri", Anne said as she kissed Kay and went down stairs.

Kay thought about Anne's parting words, "be brave". That was easy for Anne to say, she was not the one who was going to get a whipping. "Why did geometry have to be so horrible?", Kay asked herself. "Why couldn't it be easy, like reading a novel, or sailing a boat?"

After what seemed like an eternity, Kay heard Gian's footsteps on the stairs. Gian walked into the bedroom and shut the door. He looked down at Kay, who was still sitting her dresser.

"Do I need to lecture you more about the importance of your studies and telling the truth?", Gian asked.

"No Sir. I'm sorry, Sir. I'll do better in the future. Really I will."

"I'm sure that's true mon chéri."

Gian sat down on the edge of the bed. "Come here mon petit", he ordered.

Kay reluctantly walked over to Gian's right side and lay over his lap. Kay felt the cool air on her bare skin as Gian pulled up her chemise. She pressed her legs together, trying to preserve some modesty. The slap of Gian's hand on her right buttock surprised her with its sting. A second later his had landed across her left cheek. Somehow Kay could never quite remember how much Gian's hand spankings hurt. Soon the slaps of Gian's hand on Kay's buttocks was matched by her cries. Even if she was being spanked like a naughty little girl, Kay promised herself that at least she would not cry like one. When Gian finally stopped spanking her, Kay's whole bottom stung from the slaps of Gian's hand.

"You can get up now, mon chéri", Gian says.

Kay stood up and rubbed her bottom. She could feel her skin, warm from the spanking, through the thin cotton of the chemise.

Gian stood up and let Kay try to rub the sting away from her punished bottom for a minute. Kay's hope that Gian might miraculously forget about the whipping he had promised her and let her off with just a hand spanking was dashed when he ordered her to bend over the bed.

Kay bent over the bed, her palms flat on coverlet. Gian pulled up her chemise, baring her bottom. She heard the leather of his belt slide through the loops of his canvas trousers.

Gian moved to Kay's left side and wrapped the first third of the buckle end of the belt around his hand. He swung the leather strap down hard across the middle of Kay's bare bottom. The strap left a pink line across her cheeks in its wake. Kay cried out. The strap hurt much more than Gian's hand. She knew better than to move her hands from the bed as Gian whipped her, but she could not help squirming, clenching her bottom and scissoring her legs as the leather smacked hard across her buttocks. Kay's resolution to be brave and not cry did not last long. Tears were streaming down her face as she promised to be a good girl as the strap burned across her bottom. All Kay could think of was how much the strap hurt and it took a moment to realize that the painful strokes of the strap had stopped. Kay remained bent over the bed, crying as Gian put his belt back on.

When Kay stood, Gian took the crying girl into his arms, petting her hair as she cried against his chest. After a few minutes Kay stopped crying and Gian let her go. He went over to Kay's dresser and picked up the ebony hair brush.

"No, please, Gian, I've learned my lesson", Kay said, seeing the brush in Gian's hand. "I've already been spanked hard"

"Chut, mon chéri", Gian said as he sat down on the bed. "Over my knee, mon petit"

"Please, not too hard. I'll be a good girl", Kay said as Gian pulled up her chemise as she lay over his lap.

She felt the heavy brush smack across her right buttock and she cried out. Her bottom was already tender from the whipping Gian had given her. As Gian spanked her with the brush, first on one cheek, then the other, Kay kicked her legs and squirmed, but Gian held her tightly. Soon her promises to be good turned into sobs, until finally she lay limply across Gian's lap, her body shivering as the brush came down on her bottom.

When the spanking was over Gian held her until she stopped crying and then tucked her into bed. After kissing her on the forehead and turning out the lamp, he left the room.


Although it took a few more spankings, Kay eventually did learn geometry and even came to grudgingly admit that geometry had its uses. She learned to navigate by the stars, to fire a canon and to inspect ships as they were being built. As Gian hoped, eventually Kay became a captain in her own right. Those who saw her standing on deck next to the towering figure of her First Mate would never have believed that Kay had once cried like a little girl as she was spanked over Gian's knee.

Wintermute, February 2006

Case Wintermute