Tirdas 18th of Last Seed
Today started like any other day. I woke up, ate an apple, and went to spend my father's money. This was my first time in Riften though, i've heard all sorts of dreadful rumors about it, Reportedly they have Thieves living in there sewers, and if you're not watching the Dark Brotherhood will come and snatch you away for a small profit. My father dragged me here in hope that i would learn something about merchantism or life or whatever it was he was going on about this morning. I didn't really care as long as i got the money to spend on the other thing Riften is infamous for, the women! And with this coin purse i was sure to grab a couple beautiful ones for tonights retreat at the inn.

Middas 19th of Last Seed
They stole Everything! I awoke this morning to find everything had been stolen my father's money, my clothes, they even made off with my family ring! I am ruined...no... no i'm not my father will bail me out, yes just like he did in Dawnstar!
Later that day
I told father what had happened, he did not take it as well as i hoped. He told me that this was the last straw, and that I was no longer to call him father. He was so mad he didn't even leave me a pair of clothes.
Breakfast...sort of
I was approached by a stranger, says his name is Byrnolf. He said he could tell i was "light on gold" I could only assume this was some sort of joke about my current lack of clothing, and sent him on his way laughing. but he told me on my way out that when i was ready to make some money to contact him...i need to get out of this town.
That night
today was indeed a busy day. After the events of this morning i left town with nothing but a rag to cover myself. i didn't make it past the third watch tower before a sable cat attacked me! I was able to run back to safety however and let the town guards handle the cat. after which they just walked off so i took it upon myself to skin the animal making off with it's pelt. then i saw a couple of hunters heading towards a small town to the north, and i decided to follow them. perhaps they could protect me from the beasts in the area, after they missed there third elk with me in tow they offered to let me keep the pelts i was carrying for them if i left.
After the hunters i saw a band of kajiit traders heading north toward Windhelm, i decided that there was safety in numbers and they didn't seem to mind having me along. I was able to trade the pelts from earlier and some mountain flowers for a robe to wear to keep me warm as we headed further north. though as we went on i couldn't help but think how sore my feet were getting after all we had been walking all day and Skyrim's terrain can be less then pleasant on the bare foot. Which is why i was happy when we saw the wagon broken down on the side of the road, when i saw the only body belonged to a Kajiit i grew worried that the caravan i was with would stop for a day to mourn but instead they got to work stripping the caravan of it's cargo, i was barely able to grab the boots before they were done, they did however split the gold with me. As i walked off feet now warm and safe inside my hide boots and the sound of coins in rythm to my steps things seemed to be looking up. i spent the rest of the day picking flowers and creeper root we even found some nightshade and dragon's tongue along the way, on top of this the warriors in the caravan happily slayed a dozen more wolves who in turn slayed a dozen other animals, which i made certain to collect all the pelts i could. once i saw Windhelm in the distance i broke apart from the group and ran if not sprinted the rest of the way.
Once in Windhelm i sought out a smith who agreed to let me borrow is forge. i used his forge to make me some leather armor then bought two iron ores with the extra gold from the extra leathers, and made me a couple iron daggers. Next time a Saber tries to bite into me i'm going to bite into him least that's what i'm telling myself now. once i'm done with the smith i head to a place called "The White Phial," there i find an alchemy table and make 8 minor restore magicka potions and 5 resist fire potions, which i then sold to the alchemist in one day i managed to go from nothing, to owning a set of armor weapons and having 193 gold at my side after inn expenses. Tonight i will eat venison steaks, and a potato and i will sleep all night knowing that the Stormcloacks and a sturdy lock are protecting me.