Well you all asked for it, so here is one of them. A little backstory first.

Deavon "Lucky" Everclear is my Arcane Trickster Rogue. He is a pickpocket who lost his twin brother Teavon after a botched robbery attempt. The noble who caught them had Teavon killed and left Deavon to live with the guilt that it was his decision to rob the noble and him that got caught that caused his brother's death.

Unable to live with himself at first Deavon went back to the noble's home and attempted to assassinate him, but failed. Upon remembering the halfling thief; the noble who is a fan of theater relished in the drama unfolding before him. He challenged Deavon to try to get revenge on him again. The noble killed his twin brother last time, and delighted in the idea that a fitting themed punishment would be to reduce to one something there was once two of. He had his guards remove Deavon's left eye and told him that every time he tries and fails, that something else would be taken from him that he has two of currently.

Deavon has not attempted to get revenge again yet. But it's always in the back of his mind. He carries his brother's lucky coin at all times, and has learned a few magic tricks from a book his brother had and was planning to learn from. One of the magic spells he learned was "Find Familiar" which allowed him to summon a fey creature into his service. It took the form of a weasel, and has been Deavon's constant companion for years. Deavon named it Teavon in honor of his brother.

He earned the nickname "Lucky" as word spread that he'd survived not one, but two negative encounters with the sadistic noble. He was known in the criminal underworld for meting out the ultimate punishment on those who got on his bad side.

The halfling has teamed up with a few adventurers since then; A dragonborn paladin named Saralak, and an eel like creature named Valaach that claims to be a wizard. When I wrote this story Lucky was level 6, and on the cusp of Level 7. I wrote it as a treat to my DM to flesh out my character more and explain why decisions are being made for him as to what spells and skills he has or develops. Since this was going to be a personal thing and not role played with the group. I hope you enjoy it.

Art by:  xizana

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The sound of loud snoring echoed off of the walls of the small room. The bronze dragonborn on his back on the almost too small bed below the pictures shaking on their nails from the sound he made in slumber. On the other side of the room on another bed sat a Halfling. An eye patch adorned his left eye. He had given up on sleeping and his right eye roved over the words in the tome in his hands. The book was worn and old. Something he was quite familiar with given how careful he was with the pages as he turned them. Slowly and deliberately carefully he flipped the next page and held out his right hand. A current of electricity arced around it slowly idly before it stopped. A motion next to him caught his eye as he turned to see a small creature with a long noodle-like body jump onto the bed with him. It was a weasel.

“Deavon…” came a small voice in the halfling’s head. It was light, but unmistakable. There were few who used his real name. Most just called him ‘Lucky’, his nickname.

“What’s up Teavon?” he asked back in thought. His eye moved from the page he was reading over to the weasel next to him, before going back to the book.

“I need to speak to you about something. Something important. Mind if we go for a walk?” came the light voice again as the weasel scratched itself.

“Important? Is everything okay?” asked the Halfling next.

“Huh? Oh. Yes. I just want to talk about something that’s been on my mind recently.” replied the voice.

“Oh. Well alright.” replied Lucky as he closed his book and moved to stand. As he did so the weasel climbed up his clothes and perched on his shoulder.

“Something going on?” asked a new voice from the other side of the room. An eel like humanoid figure sat on his own bed eyeing the Halfling with interest.

“Nothing in particular Valaach. Teavon wants to chat a bit.” replied Lucky.

“Don’t you communicate with him telepathically? He is a familiar after all.” said Valaach in response.

“Yeah, but I don’t think I can stand another minute of Saralak’s snoring without a break. So I’m going to stretch my legs as well.” explained the Halfling half truthfully. Valaach nodded at this and watched with unblinking eyes as Lucky moved to exit the room.

***

The inn was quiet. All of the patrons were asleep at this hour. A lone set of quiet footsteps could be heard as Lucky moved through the upper floor to a window. Before he reached it he waved a hand through the air. The latch holding it closed unlocked and the window began to open. He bent and stepped through it onto the lower part of the roof of the inn. The light of the full moon shone around him as he took in the sight of the town bathed in pale light. He turned and climbed the roof tiles to the highest part of the roof of the inn and tavern before the weasel jumped off of his shoulder to the roof. Lucky stretched his arms above his head before he sat down next to the small creature. “So what did you want to talk to me about Teavon?” he asked in thought as he looked at the weasel.

“You summoned me a few years ago now. It’s been no secret that you closed yourself off from being invested in others or letting others close to you after the death of your brother and the loss of your left eye. You’ve never explicitly stated so, but I know. I’ve been filling that hole left in your heart. The fact that you gave me your brother’s name only proves this.” said the weasel in response. Lucky said nothing as Teavon spoke.

“You like that I can’t die; at least not by normal means. Because of this you don’t have to worry about having to deal with losing me; not permanently. Admittedly I worried at first about you cutting yourself off from others. I’ve seen what happens when mortals close themselves off. They become bitter, and resentful, and sometimes turn to evil. But you didn’t. You managed to hang on to who you are. And I’ve watched you slowly open back up again. It’s not anything anyone would notice at a casual glance. Only someone who’s known you for as long as I have would notice this change.” continued Teavon. Lucky’s gaze was more curious now. Where was his familiar going with this?

“But it’s not just that. You’ve grown in strength as well. You’ve mastered the spells in that book you got from Teavon. I’m sure he’d be proud of what you’ve become.” the weasel made a happy chittering noise.

“I’m not even the one who wanted to learn magic. It was Teavon’s idea to learn it.” said Lucky idly as thoughts of his twin brother passed through his mind.

“That may be true, but none can say that you haven’t been made stronger by adding those spells to your repertoire. They certainly came in handy in finding that long lost stolen treasure back in Waterdeep. You have a fair bit of wealth now, and you are partial owner of a manor and tavern to boot. You’ve come a long way from the pickpocket living on the streets.” replied Teavon.

“So did you invite me out here to wax poetic about how far I’ve come?” asked Lucky next.

“No. I’ve watched you grow, and I think it’s time I taught you how to use a powerful spell.” said Teavon to Lucky’s surprise.

“A new spell? What’s it called?” he asked curiously.

“Flock of Familiars. It’s a special summoning spell that would bring a few fey familiars to your aid. The forms they would take would be up to you and the range of your telepathy and sense sharing with them would be increased a quite a bit.” explained Teavon.

“Flock of Familiars…Sounds like a good spell, but I only have aptitude with illusion and enchantment spells. I’m not sure I can learn a conjuration spell so easily.” said Lucky after a moment.

“I know. Which is why learning this spell would come at a cost. You would have to sacrifice something to learn it.” said Teavon a little ominously.

“What would I have to sacrifice?” asked Lucky raising his eyebrow. He wasn’t sure he liked where this conversation was going now.

“Me. You would have to forget Find Familiar as a spell.” said Teavon. A look of horror crossed the halfling’s face at the thought.

“But…I…I couldn’t lose you. I don’t know what I’d…” he started. His thoughts a jumbled mess at the idea.

“Calm down Deavon. You’re a lot stronger than you give yourself credit for. I want you to be stronger, and this will do that for you.” said Teavon; his light voice sounding demanding for a moment.

“Still…” thought Lucky.

“Listen. You may not have noticed it yourself, but you’ve already built new alliances without really noticing it. Seralak. He’s become a good friend over the course of your adventure together. Someone you can trust. Valaach…I would say is an acquaintance at best, but he’s there too; though I still don’t trust him. Then there’s Gary, and even those back at the Trollskull. My point is that it’s not just you anymore. If you watch each other’s backs I’m sure you’ll be fine to face whatever comes your way.” explained Teavon.

Lucky sighed at these words. He knew the weasel spoke the truth. He had said long ago that he wouldn’t let anyone get close enough to him that they’d be able to be used against him. Or plague his conscience with guilt should he have to bail on them and save his own skin. But things have changed; at the very least in the case of Saralak. The dragonborn paladin had grown on him quickly and now was his closest friend besides Teavon. “This was why you wanted me to come outside. You didn’t want me to have a panic attack in the inn.” he reasoned. The weasel nodded his response. “What would happen to you if I was to go through with this?” he asked.

“I would simply return to the feywild. My home. You don’t have to worry about me.” replied Teavon.

“You really think this would be for the best?” he asked next.

“I do. You can only get stronger by learning this spell. I know it’s asking a lot to give up your constant companion. I’ve been by your side watching your back for many years. But I’ll make you a promise.” said Teavon next. “If you go through with learning this spell I promise that I will always be one of the familiars that come to your aid when you use it.” he announced.

Lucky was silent as he went over all that’s happened in the past few minutes. He didn’t like the idea of losing Teavon, but he couldn’t deny that a stronger spell would be more beneficial to him. And then there was that promise that the fey creature had just made. “Alright.” said the Halfling a moment later. Teavon chittered happily as he jumped and ran up Lucky’s arm. Lucky moved his arm so that the weasel was horizontal and moved him close to his face. The familiar stopped and hugged the Halfling’s face with its tiny arms and pressed its forehead against his.

“Don’t worry. You’ll be fine. And I’ll only be a summon away.” Teavon said in thought. A tear trailed down Lucky’s face from his right eye and from beneath his eye patch.

***

A few minutes later the sound of a key turning in a lock could be heard before the door to the small room opened again. It was a little quieter now. Lucky looked around. Saralak was in a different position now on the bed still straining to hold him. He wasn’t snoring quite as loud anymore. Lucky looked over to Valaach who lay on his side on his bed. The eel like creature’s unblinking eyes made it impossible to tell if he was actually asleep or not. But it mattered little. The Halfling lay on his own bed on his back and could feel the light pressure of Teavon curled up next to his head on the pillow. A familiar presence he now knew would be gone before too long. Teavon’s words pricked the back of his mind as he knew they would for some time. “We will practice this spell in the coming days, and you’ll know you have mastered it when I fade away. But I know you’ll be ready to let me go when I do.” he’d said. With this thought in mind Lucky closed his eye, and drifted off into his own slumber.