When you begin the game you are crossing the border. I'm not sure if they ever specify which way. If you generate stories and personalities for you characters, whats your origin story? use an alternate start mod? Tell me that story instead.

My khajiit was trying to sneak across the border (crossing the border out of skyrim) smuggling contraband.

My altmer was sneaking into skyrim to avoid bureaucracy and connections with the thalmor.

All of my characters start of with amnesia, I then assume the new character. So I have no idea as to why they are crossing the border or anything else. I try to adapt to each character like a good method actor would and then see where the road takes me. I find this helps greatly with my immersion and thoroughly enjoy every play through.

I use Alternate Start, live another life.

My current character, a khajiit was well known in Cyrodiil as a very decent thief and assassin. If you wanted something done, her name was on the list of qualified people. But there is a problem with becoming a famous criminal and that is eventually someone, if not a lot of people want you dead. So she fled Cyrodiil for Skyrim. Figured a fresh start in a new area would be good for her. Unfortunately for her, she was recognized by an imperial commander who placed her under arrest shortly after crossing into Skyrim. The commander took her to an imperial jail along the borders of Eastmarch and the Rift. But one fateful day a storm set in. It rained heavily for days and eventually the fort began to collapse. The commander ordered his men to kill or let the prisoners drown before escaping the flood that was coming.

Kha'tryna was the only prisoner to survive. But she does not remember a thing up to the point of her waking up in jail. You see the imperial commander had her so heavily drugged to keep her from escaping, it had an unfortunate side effect. Imagine her shock to find herself in Skyrim with no idea who she is or how/why she is even in Skyrim. All she knows is the jail was held by the imperials. And lockpicking, stealing and handling weapons seem to come naturally to her. So she is setting out in Skyrim, hoping to unravel the mystery and just because her memory is gone, her desires are not. It won't take her long to get back into trouble.

Most of the time I come up with some backstory for my character. My last guy was a man who was born to a group of nomadic sea merchants, but as he turned into a advlt a schism occured in a group towards using the combat skills taught to every member to become a effective force of pirates. He decided to sneak out of the harbour when the group was docked in Anvil, and journeyed North to Skyrim hoping find some sort of kinship with his nordic brothes. The group he was part of was extremely multicultural and utilitarian, and he found the culture of Skyrim to be quite a shock ,but he was atleast able to put his skill in blade and bow to good use as a mercenary.

Thats the gist of it anyway, I had quite a bit written up about Gunnar

I stopped counting the number of characters I have created for Skyrim at 50. Each one is created with a different personality profile. Some are created with elaborate backstories that are nothing short of being a short story. Others may only be a paragraph in length and still some may not have a clue who they are, where they are or how they got there.

My characters stopped crossing the border about a year ago. Now, I use the Live Another Life mod by Arthmoor.

Some characters are created after the backstory while others begin as I simply start playing with the creator and look into their face and ask.. "Who are you."

If I see something in them or they inspire a story as to who they are... it goes form there.

I have so many, but most of them are over several pages long. So in a extreme nutshell since I'm getting a migraine ><, my most recent characters.

Keeping in mind all these characters, except for Grig, take places 20 years after the events of Skyrim.

Grig's is rather simple: He was adopted by a Redoran guard in Raven's Rock, while odd considering Grig was an Orc he was taught sword play and the like since he was a child, he followed his (still living) father's foot steps and joined the guard. That's the gist of it.

Urso: The Half-Orc grew up rather spoiled but a well mannered man as well, much like one of his father's, Gilliam, he learned multiple fighting styles growing up, he however got comfortable using magic. Being the son of the general a lot of weight is put on his shoulders ever since a young age, which resulted in several escapades with his friend, Machk. Now both of them travel Skyrim with a simple goal, to explore.

Wuvlar, A Half-Orc agent, the young man has gotten a reputation within the Legion due to his skill with the bow, he is the oldest of his three brothers. The man specializes in tactical espionage and is a lone wolf in his missions. He now concentrates on smaller missions within Skyrim since he got married to a Nord by the name of Lod.

Gregor: Another Half-Orc, this man is, to put it bluntly a drunk, a jolly drunk, he the charisma allowing him to make friends with almost anyone he comes across with, he's also known for...making crazy decisions, climbing on top of a Giant for a piggy back ride, wrestling a werewolf, playing cards with a Draugr...

Like Senor I stopped counting how many characters and backstories I made after 50 and like Berret thinking about it gives me a migraine.

Most of the time I use a variety of alternate start mods. One of my favorite starts was as a tavern wench in the Frostfruit Inn in Rorikstead. Her parents died in a bandit attack not far from Rorikstead when she was very young. Mralki took her in. She has been doing odd jobs around the place for years. At the time the game begins she is dissatisfied with tending bar and waiting tables. So she takes her father's sword (which she has kept wrapped up in a cloth under her bed) and, with Hralki's blessing, sets out to find her own way in life. I converted the tavern wench outfit into Light Armor and added a custom sword for her.