DISCLAIMER: I love Critical Role and have nothing but respect and admiration for the producers and performers. Any analysis or opinions here are stated with love, and understanding that a show which is largely improvised cannot and should not be held to the same expectations as a show which is rehearsed and written with certain representations in mind.
In the first season of Critical Role, queerness and sex work were present, but mostly in the ways it is usually present in pseudo-medieval fantasy media. The mighty warrior and carousing minstrel visit a brothel to blow off steam or comfort themselves after a hard day. The wealthy show-off gains a sympathetic facet when it's revealed he is pressured to be closeted by his family and the ideals he wishes to live up to as a hero. The bisexual pretty boy is flirtatious with men, but ultimately ends up in an epic true love story with a woman. These are not negative representations, but they are certainly things we've seen before. The sex workers were never shamed, but they were also never really seen or named. The queer relationships were never ridiculed, but they were also never really in the spotlight the way the mixed pairs were. In season 2, though, this appears to be changing.
Sex Worker and Loving Parent
Jester, the tiefling cleric and daughter of a famous courtesan, has finally heard back from her mother. She had written to the Ruby of the Sea a few episodes back asking for more money, which is typical behavior for kids who have left the nest for the first time. It turns out Jester has not been very successful at managing her money since she was given and lost the princely sum of 5,000 gold when she left home. Jester's mother has sent her an absolutely lovely letter, telling her how proud she is of her and how much she misses her.
"While I will always miss that little girl, I am equally eager to see the woman you will become."
The care package is filled with thoughtful gifts showing how deeply she knows Jester’s interests: some of her own perfume, an ink set with her favorite colors to paint with, and 200 gold. The party dubbed it "Mom's Emergency Fund." Bless. From her name and Jester’s heritage, we assume that the Ruby of the Sea is a red tiefling, but her race and appearance has not been explicitly stated yet. Her letter did say she hoped one day Jester could come back to visit, so hopefully we will all get to meet mom on screen when that happens.
The Best Hands, the Best Conversation
We learned recently that Molly, the party’s other tiefling, has no memory of his life beyond two years ago, which is the reason he is always on the hunt for new experiences. So it is no surprise that when the party stayed their first night in a luxurious hotel, he was interested in the companions who were on offer to guests. The concierge said that they have companions "across the spectrum" who can lend an ear, or other services. Molly asked for two companions to give him a massage and company, and specified when asked that the gender identity didn’t matter so much as the skill set.
"Preference? Male, female, inbetween?"
"Best hands, best conversationalist. Surprise me."
Molly gets a visit from a young man and woman, and the player specifies that "ridiculous conversation" goes on throughout. The very fact that both sex workers and a variety of genders were offered without slyness or secrecy normalizes the service and sexuality, even if the embarrassed giggles from the players didn't. Even the language of "companions to lend an ear" is not necessarily a euphemism: in Amsterdam, the overwhelming majority of services provided by sex workers (according to the city’s Museum of Prostitution) are nonsexual. The service Molly received on stream was described as "massage, conversation, and otherwise" which leaves the door open to interpretation, but I think it's safe to assume that this character has been confirmed as bisexual or pansexual. In any case, he seemed very pleased by the results, declaring afterwords as he marched into the party's room:
"I am your god, long may I reign, eat of my fruits."