My favorite quest line in Skyrim was the Thieves Guild and I was sad to see not that many stories about its members. This story is centered around an OC but will feature all Thieves' guild and Nightingale members. So you know my stories are rated M for violence, language and sexual content. Hope you enjoy it and let me know what you think. I love reviews.


Windhelm, the city in which I was born, stretches out before me. Standing outside the door of the house I live in, I stretch allowing my muscles to flex along with the leather armor that protects them. I turn back locking the door thinking about all the other mouths still sleeping inside counting on me to bring them something to eat tonight. Fourteen mouths in all, most of them younger than my own seventeen winters expecting me to feed them. Most Nord children would have been sent to the orphanage in Riften, but nobody cares about Dunmer children, at least not in Skyrim.

Being half Nord at least allows me to pass through the other parts of the city mostly uncontested, which is why its fallen on me to look after the others. Tying my bow across my back and strapping my belt knives on each hip, I start out toward the city gates. The elven bow was the one thing my mother left me before she died, and it's my one prized possession.

I check my gear one more time before heading out. I carry my leather helmet with me for once I get outside of Windhelm. My leather boots are worn but in good shape and most importantly are silent when I walk in them. After making sure everything is where it should be, I slip on my gloves as I approach the main gate. The guards pay little attention as they open the gate allowing me to slip outside.

The wind smacks me across the face as soon as I get on the other side of those big city walls, and I hurriedly put on my helmet to keep the wind off my head and ears. Starting into a light jog, I work my way across the white river bridge down toward the hot springs. Hunting is always good in that area, especially during the winter months. The journey takes about an hour on foot, and I find myself ready to start my hunt as the sun starts to rise in the east. I set up in a tree on a hill facing west toward Whiterun just south of the hot springs. Pulling my bow off, I settle down and wait.

After a couple hours, I am treated to my first sign of life on this cold windy morning. Hoping to see a nice plump deer, my heart sinks at the site of the big saber cat. Weighing my options, I realize I only have one choice. The cat means the chances of seeing a deer anywhere around here today are slim to none, and I don't have time to set up another tree stand this late in the morning. On top of that, if I don't get the deer to the butcher by three it won't be ready for supper tonight.

Drawing my bow, I level my sight down on the saber cat. I need a heart kill, or I won't be able to take it down within bow range. Slowing my breath I settle the arrow onto my target. My heart starts to beat in my ears as my breath slows down to almost nothing. I start to hear everything around me while my eyes are locked onto that small patch right behind the cats front leg. I have to miss the ribs, or this is all for nothing, I mutter to myself. The cat stops and looks around, and I decide I won't have a better opportunity. So, I wait for that natural pause between breaths, and I release my arrow. Watching it travel through the air, I see as it makes contact right where I aimed it. The cat drops instantly, and I finally allow myself a nice long breath. I wait and watch for another few minutes just to make sure there aren't anymore big predators in the area before re-hooking my bow and sliding down the tree. I draw my knife and slowly make my way toward the downed cat. It doesn't move at my approach, but I see it's still breathing. I move quietly around toward its hind end. Sneaking behind it, I level my knife and in one smooth motion bring it across the animal's neck ending its life in a spray of blood on the ground. Once I am sure it's dead, I set about the horrible task of field dressing it.

After the messy work is done, I pull out the leather sling that I brought with me and hook it under the animals front legs and around its neck. Bracing my legs, I stand up bringing the animal up along with me. Even gutted, the thing weighs a good 200 pounds at least, and I start to struggle straight toward the road heading toward Windhelm. The less time I spend with an animal carcass on my back the better. Making my way through the trees, I stop once the road is in sight.

This is the tricky part since technically I'm poaching, bringing the animal through the front gate is out of the question, and if a soldier happens to see me chances are I will be spending the foreseeable future in Windhelm prison. I spend a few minutes at the edge of the trees looking up and down the road in both directions. Seeing a traveler coming up the road toward the city, I crouch down and watch as they approach toward where I am. As they get closer I notice that the traveler is actually a female. Her hips have that natural sway that only women can do, and her leather armor is fitted across her chest and legs. Once she gets a little closer, I notice her silver hair as it blows around her neck under her hood. That's when it hits me. The black leather armor is famous all over Skyrim now. Ever since the dragons returned a couple years ago, news of the return of the Thieves Guild came with it. And now right in front of me walks someone who is not only a member but is wearing the armor of one of the guild leaders.

Plans immediately start running through my head as I think of ways I can impress this woman and get her to invite me to join her guild. I stole my first loaf of bread when I was 6 years old and have lived off what I could take ever since. There isn't much else to do as an orphan kid in Skyrim if you didn't feel the Stormcloaks or Empire were worth dying for. As far as I was concerned they could both go fuck themselves. The Stormcloaks would much rather I leave Skyrim anyway, and the Empire sure hasn't done anything for me or mine. Of course, even the war is over now that the Dragonborn has killed Ulfric, and all that's left to do is finalize things with the Moot.

I watch her walk away along the road toward the city as my mind continues to run through idea after idea. Grabbing the sling I laid on the ground, I pull my prize back onto my shoulders and start to quickly cross the road. Renewed determination makes me walk faster as I make my way toward the river. The people who make their homes in the gray quarter know ways of getting things into the city untaxed, and that's what I plan on using to get the meat to Ambarys Rendar at the corner club. I made a deal with him a couple years ago when I realized I was a talented bowman and hunter. I would provide meat for him untaxed if he would feed the orphan kids, and so far it has worked out well. I would go hunting a few times a week and sneak my kills back into the city, and he would make sure the kids got at least 2 good meals a day. Realizing that I was planning on leaving the city tonight after that guild master, I would have to rearrange my agreement with him to make sure the other kids would be OK without me.

I make my way through the hills on the east side of the road as its less traveled and home to fewer animals. Once the bridge is within view, I start to make my way down toward the icy river below. This is by far my least favorite part of this, but I always do what I must. I walk along the river until the docks are past me on the other side, and I start to slip out of my boots and pants. Swimming in boots and pants is hard enough, but when you add a couple hundred pounds to that you can quickly find yourself drowning. I learned that the hard way. Once I secured my pants along with the rest of my equipment I jumped into the river, gasping at the coldness of it. Dragging the animal into the river with me, I start the slow journey across. I can feel my legs start to go numb within minutes and my breath becomes ragged. I block it out as well as I can and continue my crossing. Thinking I will be so glad if this is the last time I have to do this.

Once I finally get across, I pull the cat carcass out of the river behind me and drop it along the rocky shoreline. Shivering in the winter cold I quickly put my pants and boots back on and strap my food back onto my back. I now have an hour at most to get back indoors, or I could die of frostbite. I quickly pick up my pace as I start to walk back toward the docks. My legs are heavy and numb, and I can't feel my feet at all inside the waterlogged boots. Stopping at the docks I wait for a certain Argonian to see me and make his way over. Stands in Shadows makes his way over and helps me with my kill. Once were settled he leads me into the Argonian Assemblage toward the back. I help him move the dresser away from the wall revealing the small tunnel that goes under the city up into the gray quarter. He helps me carry the dead animal up the tunnel stairs until we reach the sewer grate that leads me into the gray quarter. These back alleys and sewers are never used by guards or anyone who would care we are smuggling things into the city, but just to be safe, I climb up first and look around before I signal for Stands to help me with the cat. Using the sling again, I pull as he pushes the animal up through the crate. Between the two of us, we make short work of it. Once we're done, I nod at the reptile and he nods back at me before turning around and heading back toward his small piece of hell that all non-nords get if you happen to live in Skyrim.

I only spare him a glance before I pick the animal back up and make the last leg of my trip to the back door of the Corner Club. Knowing I am coming, Ambarys always leaves the back door unlocked on the days I make my deliveries. Once I set it down on the prepping table like he showed me, I walk through the door toward the bar. Too early in the day for any of the workers to be here, it's just Ambarys and some of the most unfortunate inside the bar. Ambarys looks up when he hears me walk in, and he nods at me before returning to wiping down the mug in his hand. I get his attention again by banging on the wall, and when he turns back to look at me, I signal for him to follow me into the back.

"What's up, Shift?" He asks me when he comes through the door into the room I put the saber cat.

"I need to rearrange the deal we have." I tell him.

His eyebrows raise at that, and he sits himself down in a chair and replies, "What sort of rearrangement?"

"I'm going to be leaving here within the next day or so, but I want to make sure the kids still have a place to eat. So, I was wondering what you would need from me to make sure that happens." I tell him.

He knows better than to ask where I was going or what I was doing since often with our lives the less we know the better. I watch as he works things out in his head. He takes a couple seconds, and I wait patiently for his answer. When he finally does give it, I sigh in relief as it's as reasonable as I had hoped.

"I would need at least 50 gold a week along with some meat every couple weeks. That's for all of them. I will also make sure they get any clothing or other needs along with two meals a day."

"I nod and ask him, "Sounds good. Will the cat be enough to feed them for this week?"

"Yeah. You've been a good asset to me these last couple years. I will make sure they get fed with it this week. But understand I won't have the means to feed them if you can't hold up your end of the bargain. The first time you don't pay me, they will be going hungry. Is that understood?"

I nod at him again thankful it wasn't a hard deal to strike. Still freezing from my trip, I realize I need to get out of these clothes and let them dry before tonight. Telling him thanks, I turn around and rush over to the house we all live in. I pull the door open and am greeted by the sight of an empty house.

"Anyone home?" I shout out as I start to remove my boots.

"Back here." a female voice answers me.

I smile thinking about the girl the voice belongs to. Breynna is a winter older than myself and has been my closest friend since I came to live in this house. A full Dunmer, she stands a couple inches shorter than me, and her skin is the most flawless gray you will see. I always admired her glowing red eyes since my own ended up being a mottled gray because of my mixed Nord and Dunmer background.

The house we live in is a simple two story building left forgotten in the back of the gray quarter. We have scraped together anything we can to turn the run down building into a home. A wood stove fire pit sits in the middle of the front of the first floor. Random kitchen and house supplies are scattered around the makeshift cabinets and cupboards that make up our kitchen. In the middle is our dinner table, while we have the back blocked off to give ourselves as much privacy as we can for the restroom and bathing area.

I walk back there and notice Breynna leaning over the tub we use as a bath. Her hand resting inches above the water and flames calmly cascading from her fingers heating the water. She looks up at me as I pass by the wall and smiles at me. I can't help smiling back as I step all the way into the room and start to take off the rest of my armor.

"It was really cold this morning when I went out after breakfast. I knew you would need a warm bath when you got back. Hurry up and get out of those wet things before you catch your death."

Looking down at her while I strip, I can't help but notice the way her underclothes cling to her body. Her perky breasts and cleavage show wonderfully from my vantage point. I strip off everything since all modesty was lost between us months ago under a full moon on an unusually warm summer night.

She makes no notice of my nudity as she tests to make sure the water is hot enough. Once she's sure, she says to me, "OK. It's all set. Go ahead and get in."

I slowly slip my first leg into the tub. Once I am sure she's right, I sink the rest of the way into the water. I sigh as I get settled. The tub is big enough to stretch my legs out, and I use the opportunity to stretch and let my body relax from its stressful morning.

"How did the hunt go this morning?" I open my eyes as she asks me.

She watches my eyes as I look up at her. Leaning over the tub with our faces so very close, I can't help but notice her scent. She smells of fresh fruit and lavender, and I allow myself a strong whiff before answering her.

"No deer this morning, but I did get lucky and heart killed a saber cat. There will be food enough for all of you for this week at least." I cringed as soon as I said it since I knew she would pick up on my mistake.

"What do you mean 'all of you'?" I watch her frown as she asks this.

I take a deep breath, using the opportunity to think how I'm going to answer this. Realizing there is no easy way to say it, I decide to just do it.

"I noticed a traveler on the road from Riften. Someone wearing the armor of a Thief Guild Master. I watched her come into the city." I watch for her reaction and when I see her puzzled face my excitement and worry sends the words crashing out of my mouth.

"Don't you see? This is finally a chance for me to get out of here. All I have to do is find her in the city and make her see what an asset I can be to the guild."

Her anger rises quickly and she answers me, "And what of the rest of us? Are you so quick to forget the mouths depending on you for food and shelter?"

"Of course not, Breynna. You know I would never leave if I knew I wouldn't be able to take care of everyone. But think of it. This is the finally a chance for me to make things better for all of us. I already talked it over at the corner club and for a modest fee he will allow you all to continue to eat 2 meals a day there. Don't you see? We can finally improve our situation here." I can't help the desperation in my voice as I plead with her to understand.

"And what of me, Drake? Is it so easy to leave me?" The accusation hurts, and I show it openly.

"Is this what you want, Breynna? All of us struggling week after week to just put food on the table, or hoping guards don't show up to throw us all into the street. Tell me a better way, and I will do it. Don't you see? I'm not just doing this for me. I'm doing it for all of us." I answer her.

"I don't want you to leave." She says simply looking down at the floor.

I sit up, turning toward her and taking her face in my hands. "There was a time not long ago where you dreamed of wearing the robes of a mage of Winterhold. Have those dreams died so easily? Do you still not dream of exploring all those wonders you tell me about?" I tell her as gently as I can.

"I'm just a useless orphan girl. The only options open to me are begging or opening my legs. Those are the only things a poor Dunmer girl can do in Skyrim. What a foolish thing to even think that. I'm not a child anymore, and I won't dream childish dreams. I have responsibilities, and I won't abandon them to follow foolish pursuits. Tell me this, How can you?" Her eyes bore holes into my soul, and I look away as I answer.

"Because I won't let my life be judged or controlled by anyone. Who are these Nords to tell me what I can and can't do based solely on what race or races we are? Being on the street taught me only one skill, and by the nine I will use it to get out of this dead end of a life." I answer her my own anger lacing my words with venom.

"So, you will cheat and steal and the rest of the world be damned?" She accuses me.

I look right back into her soul as I answer her accusation. "Yes, I will."

I watch her face turn desperate, and she reaches into the tub taking hold of my manhood. "I can take care of you. You know I can." She pleads with me while stroking me up and down.

My body answers no matter what I think, and I know she can feel me get hard in her hand. It feels so good my whole body begs for me to let her take care of me. Screaming my frustration, I push her hand off of me, and she falls onto her backside at the side of the tub. Turning to face her, I answer her shocked face the only way I can.

"Three months Breynna. That's all I ask. If you still want to stay here with me when I have the money to send you to the college then we will go right back to the temple in Riften and get married. I'm not running from you I swear, but I cannot stay here. It has nothing to do with you, but I know we are both meant for more. If that includes us being together, I will be so happy, but I won't let fear keep us both here wondering if this is really what we are meant to be."

She stares at me as the tears fall freely down her face. She breaks down completely, and I watch helplessly as she rushes off up the stairs into our bedrooms. My heart breaks with her, but I know if I go up after her we will both be stuck here for the rest of our lives. I do not want that for either of us. I fall back into the tub and slide down under the water hoping that I wasn't making a mistake. Exhaustion comes quickly, and I feel myself falling asleep in the water. Not having the energy to fight it, I let darkness come for me, and I embrace it like a lover.

I'm awoken suddenly by the rushing of the younger children running up the stairs toward their rooms. Their laughter just reminds me more of the misery awaiting for me up those same steps. Getting out of the now cold bath, I dry myself off and put on the clean underclothes Breynna left for me. Noticing for the first time that someone had taken my leather armor and hung it by the wood stove for it to dry.

I look over to the candle burning on the top of our cabinet and see its well past five stripes. Night is already claiming Skyrim, and I need to find the woman before she starts with her business if I am to be successful in my plan.

Quickly putting my armor back on, I realize that my hood is upstairs in my dresser. Not ready to face Breynna yet, I decide my light gray skin should be fine for the amount of skulking I plan on doing. Sliding my feet back into my boots, I attach one of my belt knives onto my side and slip out.

Shadows claim every wall and corner in this city as soon as the sun sets over the large stone walls. Moving unseen in Windhelm after dark isn't hard if you know what your doing, and I know exactly what I'm doing.

I nod at Silda as she huddles against one of the light fires that light up the main gate. She sees me easily in my hiding place even if the guards have no idea I'm here. She was the one who taught me how to sneak and pickpocket, and I owe the old beggar woman more than anyone still alive. I wait for the guard to turn their attention away before I slip inside Candlehearth Hall.

Knowing better than to ask anything of Elda since she would rather I die than exist, I slip back into the kitchen to see if Nils is there. Sure enough, the old man is working over the stove, and I approach him silently.

"Hey Nils. Can I ask you something?" I ask him.

"Oh, it's you. Damn it child. You know I hate it when you sneak up on me." The old man replies at me a smile creeping around the corners of his mouth. "What is it that you need?"

"I was wondering if you noticed if an Imperial woman checked into the inn today? I need to find her." I asked him.

"Aye child, that I did. She ate dinner just a few minutes ago and slipped back out into the night. She hasn't rented a room that I know of, but you would have to ask Elda to know for sure." He answers me.

"I doubt she will be back tonight, but thanks. That's what I needed to know. Have a good night Nils." I tell him, turning away walking back toward the door. He just nods at me and turns back to his work.

So that means she's already started casing the houses. I need to get over to the residential area and see if I can spot her. Deciding on the path I will take, I fade back away into the shadows. A quick trip around the inside of the outer walls and I find myself at the beginning of the richest part of Windhelm.

Crouching down in a corner, I try to think of the best vantage point to look out for my target. Deciding on a roof of one of the bigger houses, I choose Hjerim as being best suited for my purposes. The owner, whoever she is, is hardly ever home, and the house is situated where I should be able to see most of the comings and goings in the area.

Cautiously I move around this area, avoiding guards altogether since its very well lit. When I reach my destination, I start climbing the wall up unto the roof. The old stones make climbing it a breeze, and I sneak all the way up without making so much as a scratch. Settling down on the roof, I lower myself laying prone down on my stomach. I wait patiently for signs of a thief. Looking house to house, waiting for that telltale shifting of shadow that only a fellow thief will know. It takes me an hour or so, but I finally spot her on a rooftop herself watching the Stormclaw house. Distant cousins to Ulfric himself, they have fallen on hard times since the Stormcloaks lost the war. Wondering what she could be interested in with a family that has fallen on hard times, I slip down off my roof to get a closer look.

I sneak around the houses until I find a spot where I can watch her on the rooftop as well as the entrance to the Stormclaw house. I end up waiting and watching all the way until well past one before the woman thief finally leaves her perch. I watch as she slips down the house herself. Impressed with the way she moves, I realize she's the best sneak I've ever seen, well besides myself that is. She moves confidently and silently from shadow to shadow. I watch in awe as she works her lock-pick flawlessly and slips into the house. I need to have her teach me how to do that. That's the one thing I haven't been able to learn, making me stick to pickpocketing to make any money.

I carefully follow her, and when I make sure nobody has seen me and that I can't hear her by the door, I open the door she picked and slip inside myself. I immediately slip from the front door into the darkest corner in the room while I get familiar with the house I'm in. Expensive looking furnishings line every wall and part of the house. I feel a ping of envy in the pit of my stomach, and I swallow hard to bury it down there. Promising myself that all this and more will be mine. I hear her footsteps upstairs, and I wonder how it is she hasn't awoken every creature within a hundred miles. Of course that is just my expert opinion and I realize that there probably isn't anyone in Skyrim who can move as quietly as I can.

While she makes her way from bedroom to bedroom, I sneak back to the sitting area. Checking every desk and table for things of value I realize that everything in this house is valuable. Not wanting to carry out a bunch of stuff, I look around for something that catches my eye. Finding it right out in the open in a display case, my breath catches when I see the jewel siting there ready for the taking. A sapphire as flawless as I have ever seen. My eyes get lost in the depth of the jewel and my hands shake as I take it from its spot. I've never taken anything this valuable before, and I can't help but feel the exhilaration of the theft. Realizing how addicted to this I will get, I smile knowing deep down in my soul that this is what I was made for.

Pocketing my prize, I slip back into my shadow and wait for the thief to come back down. It takes her about 20 minutes total to clean out the house, and I see her face up close for the first time. Her beauty is striking. Her features are strong for a woman, and her eyes tell tales of strength and cunning. I find myself wanting this woman, but that really isn't that hard to believe since it happens around most good looking women. I watch as she slips back out into the night, and I wait a minute or so before I slip out myself.

I move quickly away from the front of the house since its where I'm most visible. Once I'm safely along the side, I take a moment to scan around for my thief friend. Right when I find her the unthinkable happens. Three torch bugs light up around me, and she turns toward the changing in light and looks right into my eyes. I freeze feeling my stomach trying to work its way up my throat. As quickly as they are there, they disappear, and as soon as I'm cloaked in darkness again I move quickly in the opposite direction of the thief. Walking as quickly as I dare I move through the city away from that woman. I change direction at every intersection hoping it will make me impossible to follow. I do this for a good five minutes before I decide to stop and kneel in a corner. Scanning the darkness around me, I look for anything that looks out of place. After a couple minutes, I finally allow myself to relax and take a few deep breaths to settle myself.

Once my heart rate is back to normal, I leave my corner and start to work my way back toward the city entrance. Thinking of ways I can get the woman's approval now that she has seen me, I feel despair threaten to overwhelm me when I realize I probably ruined my only chance at getting out of here. As frustration clouds my judgement I slip around the corner and stop instantly when I feel the blade of a dagger against my throat.

"Who are you, and why were you following me?" A woman's voice accuses me. It's dripping with anger and distrust, and I feel the knife start to cut into my flesh.

I stutter and stammer my answer. My fear choking my words in my mouth. "I, I, I was trying to impress you."

I feel the dagger relax against me for a second, and I finally allow myself to breath. "What do you mean impress me?" She asks.

"I know who you are, and I know I can be an asset to the guild. I thought of this plan where I would sneak into the same house as you and lift something and sneak back out without you ever knowing I was there." I tell her my voice cracking under the stress. I cringe realizing how I must sound like a child.

"What did you lift?" She asks me calming down. The dagger still at my throat, her other arm pressing into my back.

"A sapphire." I answer her. "The most beautiful gem I have ever seen."

"Show me." She commands me.

I dug into my pocket and pulled out the stone, offering it to her. She presses herself against my back keeping the dagger pressed against my throat. Reaching around me she grabs the jewel out of my hand. I wait a couple minutes while she thinks what to do with me. Life and death don't have much meaning to a child of the streets, but for the first time in my life I realize I don't want to die. What she says next surprises me.

"I'm going to lower my knife. When I do, I want you to turn around and look at me. Understand?"

I nod at her, telling her I understand. I feel her lower her knife, and once its gone, I slowly turn around to face this woman. She looks me up and down for a second.

"How old are you?" She asks.

"Old enough to have nothing to lose." I tell her holding her eye contact.

"So, what is it you hope to gain then?" She looks right into my eyes as she asks back.

"Everything I have lost plus so much more." I tell her.

"And what are you willing to do to get it?" We continue the conversation.

I almost blurted out anything but thinking better of it I decide to draw a line I won't cross.

"I will take what hasn't been offered, but I won't kill anyone." I tell her.

I watch her reach into her pocket and pull out a small bag of coins. She extends the coins toward me and says, "My name is Vex. What's yours?"

I keep my hands at my sides when I answer her. "Shift."

"Well Shift, if you can find me in Riften by sunset the day after tomorrow then you are welcome to join the Thieves Guild. This is your cut of the sapphire. Oh and here are a few lock-picks in case you need them." She tells me this and then turns around and disappears back into the shadows.

I don't try to watch or follow her. I just stand there dumbfounded until it finally hits me. I'm going to be a member of the Thieves Guild. I laugh out loud myself before disappearing into the shadows heading back toward the orphanage. Get to Riften in a day and a half. I can do this.