The Wailing Maiden (Halloween Story Part One)

As promised, a brand new free Halloween story for my readers! This is a decent sized short story so I’m breaking it into two parts, but I won’t make you wait long. Part two will be up tomorrow just in time for Halloween.

I’m really happy with how this came out and I’m going to be honest I was tempted to hold it back and turn it into something bigger for publishing, because it all pulled together so nicely. But I promised my loyal readers a story and that was that! I hope you enjoy, as always I’d love to know what you think about it!

The Wailing Maiden

Chapter One

Gwen tossed the paperback to the floor with a dramatic sigh. She’d blown through the story so fast and part of her kind of wanted to start over at the beginning and read it again. It had kept her captivated until the very last page. Which, she had to admit, was probably less because of the author’s skill and more due to her extreme interest in hot pirates. Not that the writing was bad, it was just that she’d been on a real kick for pirate stories lately.

It was clear to her that she’d been born in the wrong time. Instead of wild adventures on the high seas, all she got was a minimum wage job and a crappy apartment that was falling apart around her. She wanted to be a fierce pirate captain, or at least the captain’s woman. Either one would suit and telling herself that the reality wouldn’t be nearly as exciting didn’t shut off the fantasies.

Settling back in her pillows she thought about Strict Tom, the hero, or maybe anti-hero, of the book she’d just finished reading. Nothing was better than a sexy pirate for taking her mind off the fact that the landlord still hadn’t fixed the heater, or that the kitchen sink wouldn’t stop dripping all night long.

The best part was that Tom had actually existed, at least in some less dramatic form. Fiction based on real people was her favorite kind of story, though she really was dying to know which parts of the book were true, and which were entirely made up. She was betting most of it was the latter, but still it would be fun to research.

Strict Tom and his ship, the Wailing Maiden, had sailed up and down the coast for years, and he’d never been caught. Of course, she doubted he’d romanced a dozen upper-class women and then been cursed to walk the Earth forever by a jealous husband. The book’s plot was a little bit ridiculous, even for romance. But it was still fun to think about.

It wasn’t entirely clear where his pirate nickname had come from, or what he’d been so strict about. She’d expected it to be mentioned in the book, but it wasn’t. The foreword assured the readers that Strict Tom was what they’d commonly called Captain Thomas Bedlam though, so there had to be some story out there.

She supposed he was probably just one of those stern captains that would keelhaul you if you didn’t follow his orders, but part of her liked to think it had a different meaning. The ship’s name had led her to think that maybe, just maybe, Tom had been a kinky dude. And that, more than anything, got her fantasies going.

She liked a stern dominant book boyfriend to think about when she slid into her empty bed. Modern guys just weren’t…well, they weren’t what she fantasized about. She was all for feminism, absolutely, but sometimes it would be nice to get a little touch of that old neanderthal in the bedroom.

Equality in the world, but dominance in the bed was what would work for her. So far, she hadn’t found that. She liked to think that she’d have been happier a few hundred years ago, but she knew that wasn’t really true. She wasn’t great at following orders unless there was some kind of sexy edge to them, and she’d have hated men being in charge of her all the time.

But there was no harm in a little fantasy now and then.

That night Strict Tom made an appearance in her dreams and he did things to her that certainly hadn’t been in the book. Her ship had been attacked. The men had done their best to fight off the pirates but, in the end, they were all sprawled across the deck dead or dying. Tom took her as a prize and brought her back to his ship.

Tying her to the mast and cutting off her long gowns had just been the start of it. The dream had turned into a montage of raunchy sex scenes that had them screwing all over the ship. It was so steamy that she actually came in her sleep, something that rarely happened no matter how hot the dream was. She woke up to soaked panties and a throbbing pulse between her thighs that made it impossible to go back to sleep until she went to take a cold shower.

After that she couldn’t get him out of her head. She reread the book and then went looking to see if the author had written anything else with him in it. She hadn’t; in fact she hadn’t written anything else at all. Apparently, The Wailing Maiden, named for his ship, was the only book she’d written and since the copyright date said it was almost ten years old, Gwen had a feeling no more would be forthcoming.

Damn it.

Knowing that there wasn’t any more fiction about him available didn’t help to get him out of her mind. She found herself at the library researching local pirate legends for the real man behind the story. It wouldn’t be nearly as captivating, she was sure, but maybe knowing more would… well, she wasn’t sure what she hoped it would do. Either she’d get over him, or it would make the fantasies spicier. Either would probably be okay.

She did find him mentioned under his real name, Thomas Bedlam, and there were a few mentions of his nickname, Strict Tom too. But it was always in passing, or just a list of facts. She knew where he was born, and when. She knew the general time period he’d sailed the seas nearby, and that he’d briefly worked for the English crown as a privateer.

Of course, then she had to look up what a privateer was and discovered it was basically just a legally authorized pirate. Interesting but not exactly enthralling info to add to the small amount she knew about him. Nowhere could she find a reference as to how he got his name, or why his ship was called the Wailing Maiden.

But her deep sighs and the growing pile of discarded books attracted the attention of the librarian.

“Can I help you find something?” she asked, with a cheerful smile.

Gwen replied automatically, “No thanks,” but then a second later her brain caught up with the question and her head snapped up. “Wait. Maybe? Um… I’m doing some research on a pirate who sailed the coasts around here. I’ve found a few mentions of him, but it’s not what I need.”

“Well, tell me what you know, and we’ll see what we can dig up.”

“Okay, well his name was Thomas Bedlam, only they called him Strict Tom, I guess. His ship was called the Wailing Maiden.”

The librarian frowned in thought. “Hmm. That name sounds vaguely familiar, but I can’t think why.” She tapped her bottom lip with one finger and stared off into space. “I’m sure I’ve heard the name before… Where did you come across him?”

“Well, I read a romance novel called The Wailing Maiden, and it was pretty good, but it said the main character was based on a real man. So basically, I just wanted to see how much of it was true.” She cleared her throat. “Um, just out of curiosity.” She tried to pretend her face wasn’t glowing with a warm blush of embarrassment.

She wasn’t even sure why she was embarrassed except it felt weird that a romance novel would make her want to research a character. She was pretty sure people were just supposed to read those for quick entertainment and then move on.

“Oh! That’s where I recognized it from. I read that book years ago. I’m not usually a big romance fan, but it was really good actually. I didn’t realize it was based on a true story.”

“Well, loosely based. I’m pretty sure most of it was made up, but he was real. And I found a few mentions of him in the books here, but nothing very detailed,” Gwen explained, sighing as she gestured to the pile of books she’d already flipped through.


When nothing followed, Gwen started to wonder if it had been a judgmental sound. A ‘hmm you must be crazy’ sound. She wasn’t sure how to ask so she just waited as the awkward silence spread.

The woman snapped her fingers suddenly. “Oh, I have an idea. Have you checked the museum?”

“The… what?”

“It’s actually called The Pirate Museum. It’s a little place downtown. It’s mostly for tourists, but they do have a pretty decent archive of historical documents. I think if there are any records of the man you’re looking for, they’ll have them.”

Well, a few minutes ago she hadn’t even known there was a pirate museum in town, so Gwen was grateful for the information. And even aside from finding out about Strict Tom, she was curious about the museum. Given her current pirate fetish it sounded like a great place to visit.

She thanked the librarian for her time, apologized for the large stack of books that needed to be re-shelved and went home to do a search for the museum. She was glad she’d checked first before heading over, because apparently their hours were limited during the off-season.

It was frustrating but she was just going to have to wait until the weekend to make a visit.

Gwen really struggled over the next couple of days. Her obsession with a pirate who had been dead long before she was born was becoming an issue. He was on her mind all the time and even when she slept, he tended to appear in her dreams.

She was tired, restless, not because the dreams were bad but because they were way too good. When she woke, she felt like she hadn’t slept at all. Her body was in a constant state of arousal, and she had already gone through two sets of batteries in her vibrator without even taking the edge off.

And the dreams had changed too. They no longer started as swashbuckling adventures where she held a sword and fought off enemies before falling in bed with her sexy pirate. Everything had taken a much more seductive turn. It was like the story trappings were no longer necessary and they’d skipped straight to the erotic scenes.

While she was a fan of a good smutty romp now and then, she’d always preferred something with plot, detail, and emotionally charged relationships. This was nothing but non-stop sex action. Frankly, it was exhausting.

On the fifth night her sleeping storyline took a dramatic curve and she didn’t know how to account for it. Maybe it had been her curiosity about his sobriquet and the connection to his ship’s name. She’d wondered if he might be kinky and her dream seemed to confirm that.

This one didn’t leap right to sex and it seemed like it had gone back to having an actual adventure. She’d gone from being just a prize to one of his crew by then. His second-in-command, she thought, but that part was hazy. They were sailing under orders of the king and had attacked an enemy ship.

At some point things went sideways and the enemy rousted them, as they fled Strict Tom turned on her and began to blame her for the defeat. That part was confusing since she had no idea what she’d done wrong, or what had caused them to lose. It didn’t matter, he blamed her for it, and he was determined to punish her.

In front of the entire crew he stripped her naked and then he tied her face down over one of the cannons. The rest of the crew watched, and the men at least all cheered and laughed. They chanted something about kissing the gunner’s daughter, but Gwen had no clue what that meant.

She didn’t remember fighting him as he bared and tied her with coarse ropes. And that’s how she was certain it was a dream, because if anyone had tried to do that to her in real life, she would have thrown a full-on fit! But dream her seemed more complacent about the public punishment. Maybe she knew it wouldn’t do any good to fight.

The humiliation was high. He’d placed her straddling the barrel and it was wide enough that it was impossible to hide any secrets from the watching crowd. It was then that she became aware of how turned on she was, because she knew they could see it all.

It became the least of her worries when a sudden flash of fire crossed both cheeks and wrapped around to the outside of her thigh. She cried out and then realized she was sitting up in her bad.

She’d never felt pain in a dream so vividly before and she could almost swear her ass still throbbed with a fierce line across her butt. She actually had to go in look in the bathroom mirror before she was sure she wouldn’t find a welt there. The anxiety kept her up the rest of the night, until she finally dropped into an exhausted sleep around sunrise.

Chapter Two

The next day was Saturday and the museum was open. After waiting all week, she was anxious to get there and find out if they had any information on Strict Tom. The all-too-realistic dreaming had definitely dampened her pirate fascination. She was no longer excited to see the museum itself, but once she arrived, she did take a tour through the small building.

As the librarian had said, the focus was on tourists so most of the displays were cheesy and overdone. The gift shop was filled with cheap plastic pirate memorabilia that matched, though she did notice quite a lot of local legends appeared on the merchandise. She looked closely but didn’t see anything with Strict Tom’s name on it.

There was a small family of three ahead of her on the tour and she tagged along listening as the guide told them exciting stories of the local pirate captains. He was an older man, grizzled and grey. He might have looked scary, but his piercing blue eyes sparkled with good humor, and he always seemed to have a smile on his face.

He was apparently guide and gift shop cashier too because after the tour ended in the shop, he rang up the family’s purchases and saw them out. He’d gone back to fixing up a display when she worked up the nerve to approach him.

“What can I do for you?” he asked when he saw her lurking nearby. The ready smile invited questions and she could tell he enjoyed his work.

“Well I—that is…I’m looking for some information about a specific pirate. I did some research in the library and they suggested I come here. Is there, um, someone I can talk to?”

He settled the last piece into place and closed the case and then he turned to give her his attention. “Well, I’m the owner so I s’pose if anyone knows it’d be me. I’m Smitty, what do you want to know?”

She hesitated, trying to think of how to explain her very weird request. “So, I read this book. It was fiction but the pirate in it was based on a real guy. I guess I was just curious to find out the real story.”

A shadow crossed over his face and his smile dimmed significantly. “This pirate have a name?” The question sounded cautious.

“It’s Thomas Bedlam, but they called him—”

“Strict Tom. Yeah.” No sign of the friendly smile at all now. The blue eyes had turned colder. “You don’t want to mess around with that one.”

She tilted her head, squinting. That wasn’t the answer she’d expected. “I don’t understand…he’s dead. It was like two hundred years back so I can’t exactly mess with him.”

“Yeah, you’d think, but every year a new girl comes around asking about him. And then sometime by early November I read that same girl’s gone missing so I’m telling you… don’t.”

She stared at him in shock for a second and then a laugh burst out of her. “What?”

He sighed and crossed his arms over his chest. “I know it sounds crazy, but I’m telling you something happens with girls that go looking into that story. I don’t know how. Don’t know why. Just know it happens.”

She didn’t know how to deal with this. Clearly, he did know about Tom, but it was equally clear he didn’t want to tell her anything. “Look, I promise you I’m not going to disappear. It’s just some basic research. Please, you’re apparently the best archive for pirate lore in town. Please? You’d be doing me such a huge favor.” She tried to put an extra dollop of pleading in her voice, really pouring it on.

He looked hesitant.

It wasn’t time to back down, she doubled up and threw in some compliments too. “That’s why you built this place right? To teach people about the small name pirates no one ever hears about? It’s such an amazing little museum; I’m sure you must have something on him.”

He heaved a long sigh, but she could hear the resignation in it. He gave her a look that said he knew exactly what she was doing, but in the end…he couldn’t refuse her request. “Alright, I’ll show you what I’ve got, but if you end up in trouble…” He trailed off and she had to guess at what he would have said.

They went into a room that hadn’t been on the tour. It was filled with cases suitable for archiving, like you saw in the huge museums, not the cheap glass ones out front. The level of respect she had for him went way up.

He must have noticed because he grinned. “Thought I was just a dabbler?” He snorted. “I have more history degrees than you can shake a stick at, young lady. I probably wrote half of the books on pirates they have in the library.”

She had a feeling he enjoyed people underestimating him, but she was impressed. Writing books seemed like some weird alchemy to her. Magic. She knew how to write words; she had a great vocabulary too, but the process of putting them together into an actual book was beyond her.

He carefully removed an old book from a drawer and set it down on the table. It looked like it had been bound by hand and might fall apart at any moment. “This is a journal which claims to be a copy of an older story. It’s handwritten and old, but not nearly as old as the original would have been. Maybe about eighty years. I can’t vouch for the information because it’s a copy and I’ve never seen the original, but it has quite a lot about your pirate in here.”

She looked at him for permission first and then opened the leather cover to peer at the scrawled words. She could make some of it out, but it wasn’t easy. “Who wrote it?

“Not sure. But it’s about a woman, close to your age, who was a member of his crew. At least according to the entries. She calls herself Emerald in there,” he said pointing at the journal. “But I doubt that was her real name. A lot of the ones who went for that kind of life left their past behind and never looked back. Sometimes if they had a public record, arrests and such, they couldn’t escape it. Other times there’s no way of knowing who they were before.” He shrugged.

“How do you know this isn’t just a story? I mean anyone can write up a fake journal.” She didn’t look up and concentrated on the pages as she slowly flipped through.

“Well, there’s no way to be absolutely sure, of course. But there are a lot of little-known facts in there, things only a researcher would know, that match up to facts we have on him. On pirate life in general. Your Tom fella, you might not have found much on him in the library, but he’s been written of here and there. He’s interesting because he was one of the few who allowed mixed crews.”

That got her attention and she paused to look up at him. “Mixed crews?”

“Men and women, both. Not just a doxy below decks, but women who actually served as crew. It’s said he even had female Second for a while.”

Her mouth dropped open. That was in her dream, all of it, and it took her a second to recover enough to ask, “And that was rare?”

“Almost unheard of. Oh, there were a few women pirates. You might have heard of Cheng I Sao, or Anne Bonny?” He waited and then sighed when she shook her head. “Well, they made names for themselves, ended up captaining their own ships. But that didn’t happen much. Most of the time women who went for the pirate life did so disguised as men, like Anne Bonny. She only came out as a woman after she’d made a name, and then still dressed and acted like one.”

 “Why? I mean if they all knew anyway?”

“To put the men at ease most likely, and even if they trusted their own crew, that didn’t mean they wanted people off the ship to know they were women. Women were seen as weak. It might lead to other pirates attacking to take the ship. Anyway, sailors are a superstitious lot. Women at sea were considered bad luck, so presenting as male probably made them less nervous.” He scratched his head, looking thoughtful. “On Tom’s ship the women didn’t have to hide anything so that made it stand out.”

It was a struggle to get her mind back on track. She knew there were important questions to ask but she kept flashing back to her dream. There was nothing about a mixed crew in the book she’d read and yet… somehow, she’d dreamed it. She shook her head, at a loss.

“If you’re interested in women pirates, I have books on a few of them. Actually, somewhere around here I even had a copy of a painting of Anne Bonny,” he said as he looked around.

“I am, but another time. I’m really just trying to work this out in my head. So why do you think Tom was so different? Sounds um, ahead of his time? Equal rights for women and all?”

Smitty laughed and shook his head. “I wouldn’t say he was enlightened. I think he had his own reason for wanting women on board. There’s not much about it written down but that journal there makes a few hints about his character.”

She frowned. For some reason she didn’t like the idea of Strict Tom being a bad guy. Whether the real man was anything like the fictional one, she’d gotten attached to him. But that did pull her attention back to the journal and she flipped through a few more pages looking.

An odd statement jumped out at her. “I have no desire to copy his story, even in my own words. Perhaps it would be better to let it be lost in time, and yet… he insists it must be told always and without end. Emerald was the first, now it is my turn and I must obey.”

Gwen looked up, confused. “This is weird. Who is she saying she has to obey? Who made her write the story?”

Smitty shrugged. “Far as I can tell she’s talking about the pirate. There’s a few mentions in there about him demanding the story be shared. He seemed to think that as long as his story stayed alive, he would too.” He paused and gave her a look she couldn’t decipher. There was a long hesitation.

When he didn’t continue, she squirmed in her seat impatiently. Finally, she just blurted out, “What aren’t you telling me?”

He leaned in and pulled the book away from her. He opened the book to the end, flipped a couple of pages back and then pushed it over so she could read. “This part here.” He tapped a stubby finger on the page.

She straightened the book and then leaned in to read. It took her a while and once she was done, she went back and reread to be sure she had it right. She was frowning when she sat back. “I… don’t get it. Is this some kind of ghost story?”

She was feeling queasy but tried not to show it. What she’d just read was eerily familiar. The writer had first read about him in a story, then the nightly dreams and fantasies began, and finally it had culminated with… but that was ridiculous.

“Well, you know as much as I do. Obviously, it sounds insane.” He didn’t sound like he entirely believed that though. And after a minute of silence he explained why. “The thing is, I looked her up out of curiosity. She wasn’t anyone famous so there wasn’t a ton of records but these days with all of the ancestry researching tools it was pretty easy to find a death certificate.

“Except… it was presumed dead. She vanished after writing this. Not sure what happened to the journal but eventually I bought it in an estate auction with an entire collection of old ledgers and books.”

Gwen frowned, forehead wrinkling as she looked at the book and then back at him. “You don’t actually think there’s anything to this, do you?” She sounded skeptical but she had to force it, because she was actually beginning to wonder. The coincidences were strange.

He held up both hands as if warding off an accusation. “Not saying that. I’m just telling you what I know. Which isn’t much.” He reached down and plucked the book from the desk with gentle hands.

In seconds it had vanished back into its drawer before she could even protest that she wasn’t done looking yet. “But I—”

“Look, you seem like a nice girl. And if you want to know about any other pirate, I’d be happy to bend your ear all day, but not this one. I don’t know what I believe. But I do know that her disappearance was the first of many. There is a string of missing girls attached to the legend and I don’t know why, but I’d rather not read about another one.”


“Forget about Tom. Just forget about the story and go home, Miss. Trust me, it’s for the best.” His face had taken on a hard look of determination.

After that, no matter what she said to him, she couldn’t get him to change his mind. He was firm on the issue and eventually she gave up and went home to think. She had a lot to mull over and for the first time in days she didn’t pick up the book the second she walked in the door.

She made lunch and then sat down to eat while she thought. She wished she’d thought to take out her camera and get some photos before he’d taken the book away, but oddly what she read seemed almost to be burned into her mind. It was so crazy that this woman had experienced the same dreams. Even the mention of punishment, vague as it was, was right on target.

It couldn’t possibly be true. But what if it was? For a moment she allowed herself to entertain the thought that maybe Tom still existed in some supernatural form. There were thousands of movies out there about ghosts, even a few about ghost pirates… what if?

Would it really be so terrible to have her fantasies fulfilled by a sexy pirate with a penchant for punishment? It sounded kind of hot, all things considered, and her body seemed to agree. She shifted in her chair as things started to tighten and a shock like electricity rolled through her.

She pulled herself out of it with a snort. Ridiculous. Ghosts weren’t real and besides that… the personal notes scattered throughout the journal didn’t sound like they came from a woman who was having an exciting sex life with a sexy spirit. They sounded scared.

She bit down on her bottom lip and pushed her plate away. Suddenly she wasn’t hungry anymore. She decided Smitty was right. It didn’t matter if the story was true or not. Something weird was going on and she’d be better off leaving it alone. With a new resolve she snatched up the book and tossed it in the trashcan.

“There. Now it won’t be a problem.”

But getting rid of the book didn’t stop the dreams and later that night she was swept away by the most vivid one yet.

To be continued tomorrow!

3 Replies to “The Wailing Maiden (Halloween Story Part One)”

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