Fiction Fantastic 2025 Winning Story: “Sir Gwendolyn the Anxious” by Brianna Bird

The story below is a winner from our Fiction Fantastic Young Writers Contest, open to all youth in Lane County. For more information on this contest, including how to enter, visit here. Support this program with a donation.

You can purchase this story in the 2025 Winners Anthology, Echoes of the Future.

“Sir Gwendolyn the Anxious” by Brianna Bird, Springfield High School

First Place, High School Level, 2025

Sir Gwendolyn the Anxious

by Brianna Bird

Springfield High School

Daved Dargarious, more commonly known as Dave the darklord, was a very strange person. Dave had spent his five long grueling years as a darklord atop Mt. Tenebrae and had realized it was incredibly detrimental to his mental well-being. For one thing, it was extremely lonely, with only the occasional raven drifting by his window for company. For another, the distant cries of prisoners from his dungeon was very alarming and he was unable to relax at any time. It was also very dark and, although the rain was soothing, the lack of plant life had extremely lessened his overall happiness.

That all changed one day when Sir Gwendolyn embarked on her only quest. Shoved out the door of her father’s manor with only a sword after a debilitating bout of anxiousness had yet again kept her from doing her farm chores, Gwendolyn decided to attempt to apprentice herself to some other lord who could appreciate her skilled swordsmanship. Combat training was the only thing that calmed her; methodically improving her skills was all she could do after surviving a day in fear of being rebuked for her less than excellent sewing and cooking skills.

But this plan had also fallen short when Gwendolyn realized that she would actually have to use those skills in relation to other people. Gwendolyn had run from Lord Farley’s estate after a miserable day of attempting to joust ten loud and very rude knights with no table manners or respect for the silence of libraries. She had not left, however, without hearing of the possibility of taming a dragon on an island on the edge of the kingdom. So, equipped this time with a full suit of armor, Gwendolyn decided that she would succeed in her quest or abandon all knightly pursuits and become a hermit.

After rowing for about fifteen minutes to a very sad-looking island in the middle of the sea, Gwendolyn ran aground on a rocky alcove in the side of the cliff. Coming from within the cave was the most mournful wailing she had ever heard, worse than that of disheartened kitchen girls upon burning her father’s roast boar. She stood for a moment staring at the cliff side, and then promptly fell to her knees hyperventilating.

Gwendolyn realized two things: the sounds of wailing were giving her a very bad headache, and she would be in no fit mood to adequately regain herself until the voices had stopped. The second thing was that the boulder she had been staring at was actually the head of a sleeping dragon. Attempting to control her hectic breathing beneath her incredibly creaky armor, Gwendolyn sadly concluded that her anxious meltdowns were brought on by more than rebukes from menacing older people; she was afraid of quests, too.

But then Gwendolyn thought about why she had left her father’s estate in the first place. She had derived no enjoyment from being yelled at by her mother over disgraceful needlework, and even when she did accomplish her goal in her chores or projects, she herself felt no joy or satisfaction. She thought about how terrified she had been of wielding a blade when her brother first taught her to hold a sword, but how overjoyed she had been at learning to control its weight in order to keep herself safe.

Quests, Gwendolyn decided, were worth the terror. Quests would bring her true excitement and satisfaction. And what could possibly bring her more joy than rescuing a dungeon full of prisoners?

Then the dragon woke up, and Gwendolyn was sick all over her shiny, pointy-toed boots in absolute terror.

The dragon looked at Gwendolyn in surprise, and blew a breath of steam at her that fogged up her helm.

“I haven’t seen one of you humans since this rock was triple in size. Oh my, you don’t seem to be a normal warrior. You’re a maiden.” It huffed at her in disdain. “Usually your type are rescued from towers, not doing the rescuing.”

Gwendolyn glared at the creature for a split second. What a pathetic dragon, she thought. It was quite small, and didn’t have the decency to acknowledge her dangerous presence. Without thinking, Gwendolyn sprung forward and smacked the tiresome thing on the nose with the flat of her sword.

“That’s Sir Gwendolyn to you,” she said, as the surprised beast dropped onto its haunches and snorted bewilderedly. “Now,” Sir Gwendolyn began, aiming the tip of her weapon between the dragon’s two scaly eyes, “you are going to help me rescue these prisoners, or I am going to teach you just how bothersome a girl-knight can be without a tower to contain her.”

The dragon nodded, staring at her in shock. Sir Gwendolyn realized she was shaking, and quickly sheathed her sword in order to keep herself from accidentally taking out one of the dragon’s eyes. She wasn’t exactly sure what to do now that she had a dragon trailing her, but she proceeded towards the sound of the screams.

Upon entering the chamber, Sir Gwendolyn found five three souls shackled to the walls by their wrists. On seeing Sir Gwendolyn, they began to cry pitifully for help, until they saw the dragon. Then they went back to screaming.

Sir Gwendolyn looked at the dragon. She decided it would not be prudent to ask it to exhale on the shackles of the prisoners, for fear of mildly roasting the prisoners themselves in the process. She surveyed the group; the prisoners seemed to be three old women chained to the wall of the cave and wearing tattered rags. They were gazing at her with . . . what? Gwendolyn could not tell. A wave of anxious bewilderment swept through her. How could she possibly free them? What if she let them down? What if–

No. The knight turned to face the dragon. It shrank back slightly, apprehension glittering in its golden eyes.

“Tell me, serpent, is there a key within these halls?” she inquired, attempting to sound fiercer than she felt.

The dragon shrank back even further.

“Well, if there were, I don’t think–”

“Stop!” Sir Gwendolyn brandished her blade at the beast. “That doesn’t answer my question.”

“All right, all right!” The dragon eyed the prisoners almost apologetically, as though it were breaking some unspoken agreement. “This really isn’t how this is supposed to work, you know. But if you must be told, the key is in the top chamber of the tower. But you’ll have to ask the darklord himself for the key.” The dragon smiled smugly at the knight, lashing its legs with its tail like a cat.

At these words, Sir Gwendolyn felt her stomach (or maybe it was her pancreas, she wasn’t sure) sink into her toes. The entire point of a daring thing like a quest was the stunning lack of interpersonal conflict. She should not have to argue, be rebuked, or make requests towards anyone. Up until this moment, however, where it seemed she would have to have a conversation upon which someone’s life depended.

Gwendolyn turned to see the prisoners gazing at her imploringly. She looked at the dragon and sighed. It seemed that more than her social anxiety hung in the balance.

“So be it!” declared Sir Gwendolyn, her pulse racing. “Then ask him I shall!”

The dragon arched one forest-green eyebrow at her, before proceeding up the stairs in the corner of the room. Gwendolyn, somewhat reluctantly, followed it.

The passage was dark, cold, and had something that looked like sea-sick moss clinging to its dank walls. Gwendolyn’s sword scraped the stairs like a giant’s mortar and pestle as she slowly wound her way up the rocky corridor to a somewhat rotted trapdoor.

The dragon looked on in mild amusement as Sir Gwendolyn clanged and clambered her way through the trapdoor. It let out a puff of steam that sounded suspiciously like a snicker, until Sir Gwendolyn shot it a venomous look and glanced pointedly at her sword. The dragon fell silent, looking like a chided schoolboy.

Upon emerging, Sir Gwendolyn found herself in a circular room, with a door leading out to, well, somewhere, certainly; and, to her disappointment, even more stairs. Seeing no better approach, Sir Gwendolyn proceeded up the stairs.

The tower was tall, narrow, and felt as though it were closing in on her. The occasional window let in enough daylight for her to see where the steps were and enough rain for her to slide back down a step after she had taken it. Her armor complained creakily and noisily as she trudged, exhausted, up the spiral staircase. Hours seemed to pass in the biting cold. At long last, her feet throbbing, Sir Gwendolyn emerged onto a landing with a large, ornately-carved door.

Sir Gwendolyn lifted one metal-clad fist, and knocked on the door. The knock thudded heavily on the black wood. Her heart was in her throat. And then, seemingly of its own accord, the door swung swiftly open. Sir Gwendolyn lifted one pointy-toed foot, and stepped inside.

Gwendolyn appeared to be in some sort of poorly lit library. The torches on the walls and the curtained window did little to illuminate the looming bookcases that lined the room. A formidable-looking spike-covered chair stood on one side, with an incredibly paper-cluttered desk next to it. A large tapestry hung on the wall opposite the window.

And there, lying on the carpet in the middle of the floor, was an incredibly morose-looking boy. He flipped forlornly through the pictures of a book, his eyes staring half-heartedly at the open page. At first, it had seemed to Gwendolyn that he possessed the air of one who has been incredibly bored for a very long time. But looking at his sad eyes even more closely, she realized it was something more . . . chilling. It was the look of one who no longer cared what happened.

The boy looked around fifteen. He wore a black cloak, which seemed two sizes too large for his slight figure. A purple signet ring glittered on his finger, and shoulder length brown hair fell across his face.

Sir Gwendolyn could feel her limbs going numb, her legs shaking. She firmly grasped the hilt of her sword, and strode across the room before stopping in front of the boy, who looked up at her, shocked.

“I am Sir Gwendolyn the . . .” she trailed off, grasping for anything at all to say. “Sir Gwendolyn the Anxious!” She resisted the urge to cringe at her own lack of imagination and pressed fiercely on. “And I have traveled here by my own power, defeated your dragon, and I now demand in the name of every good thing on this green earth that you allow me to free the prisoners in your dungeon!” The boy stared at her. “Or I shall slay you most fearfully and terribly!” Gwendolyn finished.

The boy sat up, with great effort, and looked forlornly at the floor.

“I suppose. But I can’t find the key.”

Gwendolyn, surprised, did not quite know how to respond. The boy stood up, walked to the chair, and flopped down upon it in despair, his legs dangling limply over the armrest.

“I keep meaning to look for it, I just. . . .” He sighed. “Oh, I don’t know. Every morning, I wake up and I hear them wailing down there, and I think to myself, ‘Those poor souls.’ But I simply haven’t the motivation to look for the key.” He groaned, and went limp in the chair. “I am so entirely sick of this godforsaken tower. And its dark, creepy, soul-sucking chambers and its, oh, I don’t know, its solitude and its lifelessness.” The boy tucked his knees into his chest. “And I want to leave, but I’m so . . . so afraid,” he moaned in irritation, clutching his head.

Sir Gwendolyn had stood silently in bewilderment through his speech, and now, she took two small steps, before kneeling (with a great deal of squeaking from her armor) in front of the dais upon which the boy sat.

“My good sir,” she began hesitantly, “who are you? And however did you find yourself here?”

Sitting up and tucking his hands under his knees, the boy answered.

“I am Dave. Dave the darklord, I suppose, although I never wanted to be. I never wanted to be here, but I don’t want to leave, either. My father was the darklord before me, and he lived in this tower with me, until he died, and I became the next darklord. And I hate it here.”

Gwendolyn looked at Dave the darklord with a mix of pity and concern. Dave the darklord looked back at her in misery.

“Dave,” she faltered, unsure how to voice her question. “I really need, well, anything. A friend. Would you . . .” she trailed off, unsure how to state her inquiry. “Would you like to leave with me?”

Dave looked at her, shocked, but curious.

“And go where?”

“Anywhere,” the knight responded. “Anywhere you like.”

The darklord’s eyes lit up, before falling back to his knees.

“But . . . I cannot. I just simply can’t, it’s just too . . .” he trailed off.

Gently, the knight’s hand came to rest on the shoulder of the darklord.

“Too daunting? Too frighteningly permanent? Too painful? I know, my friend. But so is the destructive way you exist right now. We cannot keep forsaking the warmth of the sun only because we were burned once before. Wounds left in the dark under bandages fester and decay. We can’t just let our life fall away for fear of living it wrongly.” She stopped, mildly amazed at her own pronouncement. “This very morning, I was afraid of my own reflection. But now, I realize that fears unfaced are more dangerous than the fears themselves.” Gwendolyn took a breath. “And that is why I want you to come with me. Please. For my sake as much as yours.”

Dave the darklord tucked his knees to his chest, closed his eyes, and tilted back into his overgrown chair.

“The key,” he murmured, his eyes still closed. “I think it’s in the box on that bookshelf, in the corner.”

Gwendolyn, astonished, raced across the stone floor to the small, carved box on the top shelf of the bookcase in the corner of the room. Opening it, she found a large silver-handled key. She scooped it up, and returned to stand beside Dave, who was still tightly coiled in his seat.

“All right, Dave,” she announced firmly, “it’s time to be brave.”

Dave the darklord looked up at Sir Gwendolyn.

“You aren’t going to let me stay here, are you?”

She smiled at him, and shook her head.

“No, of course not.”

The darklord sighed, slid out of his chair, and stood up.

“Then I guess . . . I guess I had better go with you.”

Gwendolyn felt a wave of anxiety course through her gut, and then felt her turmoil overridden by a glow of something joyful. She grinned, and to her own surprise, jumped into the air with one fist raised.

“That’s the spirit, my liege!”

Anxious but resolved, Sir Gwendolyn and Dave the darklord trundled down the many, many stairs, all the way to the rotting trapdoor in the bottom of the tower.

“Is it my imagination,” panted an exhausted Sir Gwendolyn as she lowered herself through the trap door, “or does the tower get narrower the higher it goes up?”

“No, it does, actually,” explained Dave as he scrambled down after her (though much more quietly than Gwendolyn). “Father built it that way so it looked taller and more frightening than it actually is, since that’s how all those jagged towers look in pictures.”

Slipping and sliding down the last rocky staircase into the dungeon cavern, Sir Gwendolyn hastened towards a sleeping dragon and the shackles of the three prisoners, who now sat in awe staring up at the two unexpected individuals.

Gwendolyn knelt beside the padlock, and looked at each woman in turn, then announced, “My friends, be free.”

Gwendolyn fit the key into the lock, turning it until she heard a click, and watched in relief as the ex-prisoners slid the chains from their wrists, happy shouts echoing throughout the cavern. The women joined hands, and turned to see an extremely sheepish looking darklord edging across the rocky shoal towards them.

“I think I owe you an apology,” he began, looking quite ashamed of himself.

“You think?!” exclaimed the first woman, but the other shushed her.

“He is only a boy carrying on in his father’s footsteps. You cannot be too hard on him,” she said, gently.

Dave the darklord looked at his toes as though hoping for wisdom from them.

“I’m really, really sorry about that,” he said again, and Sir Gwendolyn could see a tear fall down and land on the edge of his cloak.

The last woman turned to Gwendolyn. “How can we ever thank you?” she exclaimed, grasping one of Gwendolyn’s hands in her own.

Gwendolyn nodded towards the boat.

“No need, my lady. Please, let me escort you to shore.”

The woman looked towards Dave.

“Is he . . . coming too?”

Sir Gwendolyn beamed and nodded happily, taking Dave’s hand in her other one, and led the party towards the boat. Dave stopped, and turned towards the dragon, reaching out to gently stroke the ridges on its back. It lifted its head and looked adoringly at the darklord.

“You’re coming too, right?” Dave asked the dragon.

The dragon looked surprised, before leaping to its feet.

“I suppose. I haven’t had a decent meal in ages,” it said and launched itself into the sky.

Gwendolyn and Dave helped the women into the boat and, in the gathering dusk, sailed out from the tower that had once been a prison. The first adventure of Sir Gwendolyn the Anxious and Dave the darklord was complete, but the next had only just begun.