Jewelry should follow through right after the taper goes in, tapers should not be worn as jewelry. If the jewelry isn't fitting you either are trying to put in improper jewelry or it's because you skipped a size...the tapers should go right through with no problem, there should be no pain or pressure.
The Elder Scrolls IV: Oblivion takes place in Cyrodiil, the province in the center of Tamriel. The player is able to choose from 10 races at the beginning of the game. The player can customize them in many ways, including age, appearance, complexion, and even eye color (for certain races).
That's the biggest time jump in the Elder Scrolls series so far. For instance, Oblivion took place a mere 34 years after the first Elder Scrolls game, 1994's Arena. (Conveniently, Tamriel's fourth age started when the Oblivion Crisis ended, so years in Skyrim are counted from the end of the Oblivion. If a history book says something happened in 4E33, that's about 167 years before Skyrim's present day.) Above: Here, you're going to need this.