SIDE NOTE - Some characters will not be in this scenario. Because I am lazy and I just want to update without putting so much thought into how these characters react. So only this on will only have Bryjolf and Cicero. I will add in other characters later.
Also to Carmen_Frost, I saw that you wanted a Brynjolf x Reader or Brynjolf x Reader x Cicero.I hope this will do for now. Thanks for requesting.
Brynjolf
He stayed up all night waiting for you. You told him after you were done with this Heist you could go get some drinks together. He expected that I would take you awhile to get back to Riften.He was waiting inside of your home, sitting by the fire with a drink in his hand. Ever so often he would go walk around Riften, by the main gate mostly to see if you had arrived yet.
After the third time he went out he finally returns to your house and just gave up for the night. He laid down on top of the Greensheet, still with the drink in his hand.Brynjolf leads on his elbow looking at the empty side that you would usually be sleeping at. He took a deep breath before laying down on his back looking up at the ceiling. "Good Night Lass/lad/ (name)."Even when you aren't around it was a good night.
The redhead man slowly opened his eyes, the sun of the morning filled his ears. he turned to a side reaching for his lover. He suddenly jumped up forward saying that you were still not there. "She/he/they probably taking their time again." He sighs while getting up, the drink he had in his hand had fallen off the bed. He knew you were going to get on him about that later.
It was around noon when he left your house to the guild, while he walked out a Carrier came his way. " Are you Brynjolf?" The wood elf asked.
"Depends on who's asking..."Brynjolf said Crossing his arms over his chest.
" I have a letter for you." he handed the redhead the letter. It looked pretty warned and the writing looks like shit really.
"From who?"
"A man dressed in heavy armor, I was just on my way here and you pulled me aside and gave me this.... I wasn't going to mess with him. well, that's all." the wood elf said before walking away. Brynjolf slowly opens the letter wondering what this is about. He first thought it would be some Bandits getting on his ass about something or maybe even a mercenary sent by someone who got robbed. He opened the letter and saw that it was written pretty well.
" Thieves Guild
You have stolen from the wrong family and if you wish to have this (race) return to you, I expect you to pay up what you have stolen.If not, you can expect this (race) being returned on your doorstep dead.
and if you think this is all but a jest, they're in the letter is a ( item that you carry on you like a ring or a necklace).
From The Cloud District "
Brynjolf quickly looks for the ( item of yours) and there it was in the bottom of the letter. he held the (item) in his hand. He quickly made his way to the Thieves Guild, knowing that he will be needing help with this.
"Hey Bryn." Vex said while he walked into the guild. " what's with you?" she asks not understanding what he looked pissed off. Delvin soon came into the guild with a few letters and hand.
" Has (name) return yet? a few jobs for her/ him/ them." the Delvin while taking the seat.Brynjolf quickly explains the situation that we were in. He shows the letter and the (item) of yours.
"How to get Mercer in here he's not going to like this..." Said Vex, Dirge listens to his order running off to the Guild to get Mercer
"The Cloud District.... That sounds very familiar." Delvin said, looking over the letter again."Any idea?" He asked the to other members of The Guild.
"No clue..." Vex said. " I remember (name) was talking about something like that one time... like the owner was an ass."
" Cloud District..... Cloud District."Brynjolf was trying to figure out where he had heard that name before. Thinking about the times when you have complained about someone. "Aye, I've heard her/him/them complain about it once before... But I'm just not sure where.." This is driving him insane. He wanted to know if you are alright, to know that you were safe.
Cicero
Today marked a full a half year of you being with the dark brotherhood. Cicero had gone all out to make everything perfect today. Sadly you hadn't come home this morning, you had a contract all the way out in Markarth. So out through the day, he had decorated your room with flowers. He wanted to make it special.
"Ohh, Cicero knows that the Listener will just adore this," he said well laying the flowers near your bed. He sat up drinks for the two of you for later tonight. Cicero sat at the table looking at the drinks. He had taken his hat off letting his red hair fell down to his face. Leading back in the chair he thought about all the times he was with you. "The dairy Listener spared poor Cicero." A smile came to his face. The day went by, still no Listener.
Cicero was now sitting upside down in his chair with a drink in his hand. "(Name) will come, don't worried." He couldn't if this day was more Important to him or you. He waited and waited, after a few hours past midnight, he started to drink. He started to talk to himself.
"Why did (name) pick Cicero as her\his\ their lover Hummmmm? Was it out of petty? no, no, no, no, no, that's not true. (name) would never do anything like that...." Cicero sigh while drinking the whole bottle. After he had drunk all his thoughts away, he went over to your bed just throwing himself. Cicero fell asleep immediately.
"Cicero!" It was Babette, she was beating Cicero over the head with the empty bottle of mead he was drinking. "There's a letter! The Listener has been kidnap!" Cicero's eyes spring open, he sat up immediately before running down the hallway to Nazir.
"WHAATT???!" Cicero yelled at Nazir who was reading the letter.
"Keep your voice down..." Nazir told him, he finished the letter before letting Cicero see it.Is Cicero quickly grabbed the letter reading as fast as possible.
"To the Dark Brotherhood who killed my wife.
I have one of your assassins that were there when my wife was murdered, but I am missing her\ his\their accomplice. Where is the Jester? bring me him and then we could settle a deal.
The Miner"
"So we're giving up Cicero right?" Babette asked.
"Do you want to oil-" Nazir was cut off by Cicero slapping onto the table.
"Give me every contract that we had had the last year." Cicero demand it, Nazir nodded before going to the archives. Cicero's really worried now, new that is was a dangerous life of course. Though now his worst nightmare was coming true.
Nazir Came back was a couple of old contracts. "Here are some female contracts." The three quickly went through them searching for who this could have been. Cicero was muttering random things to himself. The two others though, couldn't really understand what he was saying. Cicero suddenly pulled contract up holding it high up in the air for a moment.
"Cicero found it!" He exclaimed. "Now let's see." Cicero started to read the contract out loud. " 2000 for the death of the Silver-Blood mine leader. She is married to one of the sons of the Silver- Blood family. Make sure they don't know those leads back to me."
"Cicero will be heading to Markarth..." Cicero said while walking away.
"Alone?" Asked the vampire.
"He wants Cicero so that's what He'll get.." Cicero growled the last part. He continued walking to the entrance of the sanctuary. As he opened the door he found Shadowmere waiting for him. "Don't worry my Listener Cicero will be there."

YOU ARE READING
Skyrim Lovers: Boyfriend Scenarios
Fanfictionscenarios smuts and lemons one shorts male x male and female x female gender neutral crossover spin off stories/ stories side Anything you could thank of I can write.