Tolelajara is home to a diverse and varied populace, though the Tiefling populace that founded the settlement still form a significant portion of the population. The twin cities, split by the river that flows between the two islands, called the High Town and the Bright Town. The High Town, located on the smaller of the two islands, is home to merchants, traders, and shipwrights, offering a seemingly legal face behind which the Bright Town carries out the true dealings of Tolelajara. Brothels, bars, and all manner of illegal establishments dot the larger of the two islands, and the while many lie some distance from the actual Bright Town, all consider themselves vital to its existence. While a council of merchants and politicians leads High Town and claims to be the rulers of Tolelajara, the true power lies within the duumvirate that rules Bright Town. Called the two Princes or Princesses, one leads the coalition of pirates and criminals that rule the nearby waters and provides military might while the second runs the pleasure houses of Tolelajara and if rumors are to be believed also leads a network of spies that both keeps them in power and keeps the High Town in check. The current Pirate Prince is an aged Tiefling named Marak, a former pirate of some renown. But he is now old and the true power lies with the other princess, a former courtesan known as the Nightingale.

Tolelajara is a pleasure town, a criminal haven with a thinly veiled face of legitimacy. Due to its pivotal location it is also a hub of travel and communication across the Allirian Strait.

Much like its citizenry, the architecture of Tolelajara is a mishmash of different cultures and influences. Palatial mansions might stand next to ramshackle cottages, and a turn down an alley can suddenly take you from a brightly lit part of town with well paved streets to a muddy hovel. The two cities are also much similar in construction, showing a similar disparity in wealth which is reflected in the buildings.

High Town - Located on a small hill, High Town seemed a logical name, but over time it also came to be associated with the denizens of Bright Town thinking of them as high strung fools walking about with their heads high in the clouds. High Town's richer districts are bigger than those found in Bright Town, with better streets and some semblance of order to its construction. The inns and secret pleasure houses found here are often bright, beautiful structures. High Town's bath houses are also a well known attraction, combining traditional services with the more Tolelajarian ones.

Bright Town - Named so because it was never dark, its pleasures houses, inns, and bars stay open through the night. While it is definitely the seedier of the two twins, there are more than a few areas that can put even the Bright Town to shame. The homes of the two princes for instance are some of the most elaborate and awe-inspiring structures in all of Tolelajara. The Bright Town also houses the biggest docks in Tolelajara, serving more ships than half the remaining docks on Tolelajara combined.

In centuries past, a traveling group of Tiefling entertainers made their name as one of the best troupes in the land. Over time they grew so big that they had to settle down and establish a more permanent base of operation. That was Tolelajara was born, a small Tiefling settlement built to be a place of pleasure and entertainment. Over time the small settlement grew, attracting not just Tieflings but creatures of many a race. The founders of the settlement, having faced discrimination all their life, had but down but one tenet for all to follow. Tolelajara would keep its doors open for one and all, a haven where none were discriminated against in the way they had been.

As time passed Tolelajara's reputation as a pleasure town grew, and as the town grew more legitimate businesses started cropping up to support its population. Merchants, traders, craftsmen, many who had been forced to flee their homes for whatever reason found a new home in Tolelajara and another opportunity to use their crafts. For one reason or another, these "legitimate" businesses started settling down in the island across the tiny strait formed by the river flowing between them. So the twin cities were born, the High Town which housed the merchants, and the Bright Town that still grew around the original settlement. Both considered themselves to be the real Tolelajara, and existed in a state of tension to this day.

Tolelajara is the seat of hedonism, debauchery, and catering to the more basic desires. Be it the High Town or the Bright Town, you will never be more than a stone's throw away from a pleasure house. Even the high strung denizens of High Town still live by their baser desires, and many own side businesses catering to more esteemed clientele.

While the two cities have had their differences, any threat to Tolelajara has always proved to unite them. For though they might not like the other, the love for Tolelajara overpowers all. The same applies to those that visit Tolelajara. Though Tolelajara has no military strength of its own, the pirates, smugglers, and various criminals that form the bulk of its clientele are not loth to taking up arms to defend what some consider to be the closest thing they have to a home.