Since starting at the Shino Academy, Shunsui Kyoraku has made significant strides; despite his abject laziness and complete disinterest in anything lacking long perfumed hair, delicate hands or generous curves. He's even made some real friends.
Growing up in a noble family, he always had plenty of playmates; but the older he got, the more complicated those relationships became. He'd learned early on that most people only befriended him to benefit themselves. Eventually, he came to view even family and trusted servants with an air of suspicion.
That changed at the Academy. Here, while his family connections could get him the occasional luxury, everyone from the kitchen staff to the senior teachers treated him like any other student. He had to start relying on his intelligence, strength and charm to get by - and he loved it.
One of the first people he met at the Academy was a white-haired cadet, from a lesser noble family - Jushiro Ukitake. Though their personalities differed greatly, they became fast friends. Like Shunsui, Jushiro grew up surrounded by people working for their own ends, and didn't trust easily. A situation complicated by a strange lung condition he didn't like to discuss in detail. However, this meant he had a servant/nurse living at the Academy to monitor his condition. Initially Shunsui resented this, and worried that the woman would be an overprotective hag, trying to keep Jushiro from harm and enfeebling him further. When he met Nashi, his fears were immediately allayed. She was young, smart, strong-willed and largely let Jushiro do as he pleased, though not without the occasional sharp taunt.
After Shunsui and Jushiro became roommates, the three of them would spend much of their downtime together. Though Nashi played the quiet dedicated servant in public, when allowed to speak her mind, she could hold her own with the two men. This, combined with her endearingly odd accent, and affinity for revealing-yet-not-quite-inappropriate clothing earned her a permanent place in Shunsui's heart. They would often flirt playfully, and for a time, he considered pursuing her. He wanted to know firsthand what sort of sounds Western girls make at their peak. However, it quickly became apparent that she had little interest in helping him find out. Her devotion to Jushiro went far past that of a servant, and his affection for her exceeded that of a noble for a favorite underling. Shunsui had to settle for friendship, though he told himself that if they reached graduation before Jushiro made a move, all bets were off.
It turned out that friendship had its' perks. On cold nights, when the risk of Jushiro having a bad fit rose exponentially, Nashi would have the three of them pile into Jushiro's bed, under as many blankets as they could find. Apparently, keeping him warm and well-rested made a big difference. Shunsui would work this to his advantage, insisting Nashi sleep between the two men. She would protest each time, saying that Jushiro would benefit most in the center. Each time she would ultimately concede and Shunsui would snuggle up next to her back, while she did the same to Jushiro. In the morning, Nashi would wake to something hard poking her back, and Shunsui would have to awkwardly excuse himself to take care of it.
Still, he would think, something's better than nothing.
Shunsui continued to admire her quietly, and indulge in his cheap thrills whenever opportunities presented themselves. At the same time, he saw no point in pining hopelessly, and made an effort to keep his social calendar filled with many of the Academy's loveliest cadets...and servants...and sometimes a teacher...or two teachers. These liaisons could occupy him for weeks or months at a time, but during any particularly dry spell, his lust for Nashi would re-ignite. He worried that this made him a weak man, or a bad friend. Ultimately, he reasoned that his libidinous heart was just as lazy as the rest of him and simply fixated on the nearest attractive woman. At least until something more likely came along.