As for finding sex. There are women who find men in drag very attractive. I have known bisexual women who find the both genders aspect of it very enticing. I used to date a girl who always wanted to go to drag shows. As a guy who is not comfortable with filling a female role, being with her made me feel oddly insecure about my lack of feminity, which was a new one. But it is unlikely someone is going to be sexually attracted to Chris. But people don't always hook up with people they are particularly sexually attracted to. Sometimes they just have sex with someone because they want sex and that is the sex that is available. I don't think it is particularly likely, but I also don't think it is impossible that if Chris starts putting time and effort into being at the right place at the right time, he could stumble into a night of drunk, instantly regretted sex.