A/N: Since the story doesn't mention this; the female Dragonborn is named Katie and she is a Khajiit. :)
"Damn bandits. . ." I mumbled as I jumped on Shadowmere. I gave him a kick to the side and he ran me in the opposite direction of the bandit camp. I had to run, I was outnumbered; by a lot. After riding for a little while I realized something;
"Brynjolf!" I yelled out loud as I remembered, pulling back on Shadowmere's reins. I had left him at the camp! I swiftly turned Shadowmere back around and ran him back to the camp. I felt horrible. What kind of Guild Master am I? Leaving my colleagues to be killed.
As I arrived back at the camp I saw all of the bandits dead on the ground, but no sign of Brynjolf. I called for him at least a dozen times, but no answer. Where could he of gone? I decided to check back at the Flagon.
"Have you seen Brynjolf anywhere today?" I asked everyone that I passed. They all just nodded a 'No' in response. My heart sunk with every nod. As I reached Delvin he offered more than just a no.
"Didn't he go with you this morning?" he pointed out.
"Yes. But I, uh. . . Kind of. . . Lost him," I said quietly.
"Lost him? How do you lose a grown man?" he questioned.
"I left him at a bandit camp. . . We were outnumbered, and I just got on Shadowmere and ran out of instinct," I explained.
"Remind me again why we rely on you?" he retorted.
"Shut up. I just need to find him. I'm going to look in Whiterun; the bandit camp is near there," I said as I walked towards the exit.
I walked into Whiterun and asked around. I had to give every guard a description of Brynjolf, it became almost tedious. Just like at the Flagon, I was given a nod every time. But, as I reached Dragonsreach, a guard stopped me.
"Hey! You been looking for someone?" he asked.
"Yes. Long, red hair, green eyes, same armor as me," I described yet again.
"Check the prisons," he replied simply. The prisons? Had he gotten arrested? I ran immediately down to the prison barracks.
"Stop. What business do you have here?" a guard questioned as I reached the bottom of the stairs.
"I'm. . . Visiting someone," I explained.
"Fine. Go ahead, but go fiddling with any locks around here, and we're going to have a real problem," he asserted. I nodded quickly and ran into the room with the cells. I began looking in each of them. I started losing hope as I approached the last few cells. I looked in the second to last one and saw what (or who) I had been searching for.
"Brynjolf!" I yelled. He was lying down on the cells bed. He looked at me and smiled.
"Lass! Glad to see you're okay," he replied sarcastically.
"I'll apologize later. We have to get you out of here," I whispered. He got up and stood at the cage door.
"What if I want my apology now?" he asked as he grabbed the cell bars and leaned in, getting extremely close to my face. I sighed and gave in to his request.
"I'm sorry. I'm a horrible Guild Master and I will grovel to you on my hands and knees whenever you wish, high and all-mighty Brynjolf,"
"That can be arranged," he said in that low, seductive tone of his. I hit his shoulder playfully through the cell bars.
"Okay, enough play, let's get you out," I whispered.
"The cell is already unlocked, lass," he replied with a smile.
"What? Why haven't you left then?" I questioned, surprised.
"I wanted to see how long it would take you to find me," he explained.
"You're a jerk! I was worried sick! I was ready to send the Guild to look for you! I was-" he silenced me with a kiss. It was gentle and pure, but also in a way forceful and rough. Just like Brynjolf. He pulled away and just smiled at me.
"Ready to go?" he asked. I nodded a yes in response, still dazed from the kiss. I moved out of the way and crouched down, ready to sneak. He did the same and slowly pushed the cell door open. He led the way and we slowly made our way to the exit. As we came to the guard that stopped me before, we found him to be asleep.
"Gotta love Whiterun security," I joked. Brynjolf chuckled in reply. We got out of the jails and walked as casually as possible through Whiterun and to Shadowmere, who I had left at the stables. I mounted Shadowmere and he did the same, sitting behind me.
"I really am sorry. I don't know why I left you. I just instinctively run when outnumbered, I guess," I told him sincerely.
"It's okay," he assured, wrapping his arms around my waist and putting his head on my shoulder.
"Take us home, Shadowmere," I mumbled as I leaned back into Brynjolf. Shadowmere understood and began heading towards Riften.
A/N: Fun fact! This is based on something that actually happened to me in Skyrim. I was heading towards a quest destination (While riding on Shadowmere) with Brynjolf following me, and I passed by a bandit camp. I expected Brynjolf to take care of them then catch up like he normally does, but instead he disappeared. I waited a couple days to see if he'd pop up, but he didn't. I ended up using the console command to teleport to him, and I found him in a jail cell. I didn't even know it was possible for followers to get arrested. It gave me a good laugh :)