[collar list. some musings on sexuality.]
Italics designate someone no longer on the island.
Johnny Sfondi
Sunstreaker [male]
Tsuzuki Asato (previous)
Claire Redfield
Himura Tomoe
Sancia d'Aragon
Katakura Kojuurou
Chang Wufei
Thom Reston
Hijikata Toshizo (PMK)
Hijikata Toshizo (Hakuoki Shinsengumi Kitan)
Parsee Mizuhashi
Okita is not a very sexual person - first, because he keeps most of his own feelings very carefully under wraps, often far enough that he himself is only tangentially aware of them. Second, because he is passionately emotional, and feels that human contact, affection, vulnerability, honesty, etc. etc. threaten the rigid emotional control that's never quite enough to keep his passions properly restrained.
[Note that passions here mean anger, fear, need, misery, and so on. He's pretty much okay with affection, loyalty, happiness, and the positive emotions, except when they are too strong - that threatens his control over the negative side.]
His comfort level is therefore key to his ability to be okay with sexual situations, because the threat posed by physical affection means, to him, that he is likely to show unacceptable things that he does not like revealing to anyone he ends up sleeping with. This is why he's stuck with people he isn't close to so far. With Johnny and Sunstreaker he was the one in need of help, and so he has continued approaching them because he feels indebted; however, this lessens the likelihood that he'll be willing to accept or offer collar help from either of them in the future (particularly unlikely to accept, since it would increase the debt and be more threatening). With Tsuzuki, Okita offered help, but he believes himself to have inadvertently insulted Tsuzuki in the act, and also showed a painfully vulnerable side. He's going to attempt to avoid Tsuzuki from now on, and will be extremely formal and awkward if he has to communicate with the man. With Claire, he offered help, and while it was no doubt quite awkward, the dynamic was not one of her trying to control/protect/care for/own him; this would have made it much easier for him to be polite, affectionate, and careful without compromising his own need for self-control.
He may be more likely to choose women for collar partners in the future, despite the fact that he finds himself more attracted to/able to be himself around older, fairly experienced men. The dynamic of control and both the unspoken and spoken demands for him to open up, acquiesce, be responsive without making requests or demands of his own (Johnny ignored Souji's request not to kiss him, Tsuzuki reacted badly to Souji's attempt to tease/demand to be treated less carefully) have almost convinced him that sex with a man who does not already know him well enough to know what not to ask and what to respond to is going to be an emotionally grueling experience.
Sex with someone who does know him that well would be frankly terrifying, because if Souji has allowed someone to know that much about him, he's probably close enough to really not want them to see his unworthy and undesirable emotions - partly because he would find the humiliation unbearable, partly because he's afraid they would be disgusted or, worse, pity him.
If he finds a man he's not socially close to who's willing to allow him his distance and autonomy, he would consider this ideal. However, for the moment, non-aggressive female strangers are to be preferred to unthreatening male strangers, because the latter cannot be trusted not to think Souji should be cajoled and cuddled and gentled out of his prickly distance - or, worse, to be offended when he resists their attempts to do so.
tl;dr WOULD LIKE GUYS BUT THEY THINK THEY HAVE TO BE NICE TO HIM LIKE HE'S A DELICATE FLOWER OF HIDDEN PASSION OR SOMETHING.
HE IS ACTUALLY A CHESTNUT. TRY TO GET TO THE DELICIOUS SQUISHY CENTER AND HE WILL CUT YOU.
